"Driver picks the music..."

John's famous barbecue pit spins the mouthwatering smells of smoked meats. The tables are lined up and filled with buttery cornbread, potatoes done three different ways (mashed, roasted, and casseroled), salads, slaw, carrots and corn, wild rice, homemade dinner rolls and garlic bread, and no less than five different flavors of pie. You spy Dean tucking into his third slice of cherry. Evidently, it’s still his favorite. A piece of pastry crust flecks from his lower lip as he jumps in with an old story.

“So I’m maybe…twelve, thirteen. Bobby’s trying to show me how to fix this patch of barbed wire fence. Because I’m young and stupid, I get it in my head to jump over it while the wire’s slack,” Dean starts.

Sam and couple of the cowboys, Benny and Cas, are already smirking, chuckling a little, shaking their heads. They’ve definitely heard this one before, and this time, you have too. A smile curves your lips behind the rim of your glass of whiskey and Coke.

“I make it over, but my leg gets caught in the slack, and I just go down hard, eating the damn dirt,” Dean says. He mimes the impact of his body hitting the ground, complete with admittedly impressive sound effects. “But now the wire’s tight. Rips through my jeans, my ankle, blood soaking through. But, uh, Bobby calms me down, you know. He takes out his tool belt, and he says, ‘It’s all right, son. That’s why God made pliers, for idjits like you.’”

Laughter ripples across the table. Even John smiles, shaking his head.

“Well, he cleaned me up best he could and helped me back up on my horse,” Dean says. His grin is warm, and his gaze spans far beyond his beer. “Dad didn’t even have to lecture me. You remember what you said?”

John nods in amusement. “‘Your own body’s gonna do the punishing for me, son.’”

“Right. My ankle was busted for three weeks. Couldn’t ride, couldn’t do shit,” Dean says with a chuckle. “And it was summer too.”

At least he didn’t have to go to school, but for a boy like Dean, being cooped up in the house was three weeks of misery. All he could do was watch from his bedroom window while you and Sam ran off to ride your bikes in town or go swimming in the river.

He looks down toward the end of the table, wanting to see if you remember those days like he does. What he finds is your empty seat. His eyes run a search—and eventually catch you making your way over to the barn. His brows furrow in confusion, but as the conversation spins and Benny takes over the reminiscing, Dean gets up from the table, ignoring the little warning tug in his gut.

“Gonna get another beer,” he says.

But Sam’s perceptive gaze follows him. While you venture into the barn, Sam sees his brother’s projected path all too clearly.

The smell of horse makes you gag a little, but after you enter the barn and switch on the light, yet another wave of nostalgia blasts you in the face. You recognize that tack and tool shelf on the right-hand corner, and the rack of shotguns and rifles on the far left. You know these stalls, and you greet each of the horses like old friends, even though most of them are new ones.

You stop at one of the middle stalls on the right, clicking your tongue at an older horse. His coat is a deep coffee brown, dappled with white on his hindquarters.

“Dakota! Look at you, handsome.” You smile brightly. “Remember me?”

He blinks at you with those dark eyes, and he meanders a bit closer to the half door. You offer a loosely closed fist for him to inspect. When he does, you think it’s with some familiarity as he sniffs your hand all over. Or maybe he’s just smelling the apple pie glaze you licked off your finger earlier.

You laugh lightly and take a chance on petting the side of his neck. He lets you do it, a kind older statesman. Before you left, you had helped your dad break this horse in.

“He remembers you.”

You turn your head toward the door, flinching slightly in surprise. You didn’t even hear Dean come into the barn. His scuffed boots cross the distance leading him to you. Dark wash jeans and a black buttoned-down shirt are probably the extent of his cleaning up for the occasion, but the ensemble does suit him better than a proper suit would.

“It all looks the same,” you say quietly.

“That’s because it is,” Dean replies. His lips pull at a smirk as he points to the tool shed. “Like that dusty back room where we used to make out.”

You roll your eyes, but you can’t help the way your gaze draws to his calloused hands and long fingers. Your cheeks begin to prickle with warmth, but you refocus on his face, and unfortunately, that familiar grin. You’re sure that face has gotten him plenty of action since then.

“You do remember I have a fiancé,” you say.

Dean nods, holding up a placating hand. It slips into his pocket as he leans against a support beam. “Yeah, you never said where that guy was today.”

“Working,” you reply defensively. “We’re in the middle of a big project, and we can’t afford to drop the ball.”

“You two work together?”

“Yeah, for his father’s company.”

“Doing what?”

You hesitate. It seems like Sam hasn’t spoken to Dean yet about the offer either, but in this case, you’re grateful for it.

“Land development. His father is co-CEO and head of the Legal team. I help scope out properties and propose new projects,” you say.

Dean quirks a brow. “Land development, huh? Not what I would’ve imagined.”

His tone annoys you, making you slightly more tense, but you’ve already had this argument with Sam. You don’t have to explain yourself to this man.

“It’s not what I thought I’d end up in either, but if you think it’s hard to be a rancher, try being able to pay rent in California. We’re all just trying to survive, Dean,” you say.

At that, he actually nods more sincerely.

“Guess that’s fair. But it looks like you’re more than surviving now. You’ve got a friggin’ golf ball on your finger,” he says, gesturing at you, and more specifically your engagement ring.

You roll your eyes. “It’s not that big.”

The way he snorts earns a reluctant smile from you.

“How long you known the guy?” Dean asks.

You give him a shrewd look. He’s very curious about your personal life, but you can’t deny that you’ve been wondering what the past 12 years have made of him.

“About eight months,” you reply.

His brows raise almost as high as his hairline. “Eight months? When did he pop the question?”

“…A few weeks ago,” you say, albeit with some hesitation. “What?”

Dean shakes his head. “Nothing, I guess. Whirlwind romance.”

“And what about you?” you counter, fighting a blush. “No girlfriend?”

Dean chuckles. “Oh, I have plenty of friends. Just no time for the whirlwind.”

“I’m sure,” you say wryly. “Things really don’t change much around here.”

It’s a touch snider than you mean it to be. You don’t actually want to pick another fight. Frankly, you don’t have the emotional energy.

But even though Dean gives you a certain look, to your surprise, he doesn’t want to snipe anymore either. He just sighs.

“All right, come on. There’s some of Bobby’s stuff that you might want to look through,” he says, ushering you to follow him.

You do so reluctantly, over to the Foreman’s cabin.

The Foreman wrangles the other ranch hands, and he’s the Ranch Manager’s second-in-command. Bobby held that position for 23 years, starting from back when John was managing all operations himself. You used to live in this cabin with your mom and dad, back when they were together. 

Dean would later take your virginity when you turned 18—in the glorified closet that used to be your bedroom.

At least he doesn’t bring up that little anecdote as he leads you to the small, four-seater dining table. It has a few boxes stacked on top of it, probably what’s left of your father’s belongings. The rest has been cleared out except for a couch, an old wood coffee table, a TV on a stand, and some supplies in the kitchen. There are some signs of life here though, like a half-drunk beer on the coffee table, an empty box of pizza on the kitchen counter, and some crumpled napkins. Dean notices your observing gaze.

“I’ve been hanging out here the past few days. Cleaning the place up took a while, but uh, sometimes it’s nice to get away from the main house,” he says.

“I could see why. Thirty-two and still living with your daddy,” you teasingly remark.

Dean shoots you an amused brow raise, but he brings the first box to the living room coffee table and slides it toward you.

“Take whatever you want. He doesn’t have any other family, so I’m not sure what to do with the rest,” he says, rubbing a hand at the back of his neck.

Throwing it away feels wrong, or so his tone says. You nod in agreement and start looking through the box. The first thing you find is a large bottle of gold label scotch.

“Wow,” you say.

“That’s on brand,” Dean says, with a smirk. He eyes you. “We should probably crack it open, in Bobby’s honor, of course.”

Your lips tug at a smile. You hand it over, and Dean twists off the cap to take a swig. He offers it back to you, and you accept it dubiously after sitting beside him on the couch.

“You know we’re not teenagers anymore, right?” you say, but you still sip straight from the bottle just like he did, grimacing at the burn down your throat.

“We gotta lubricate this trip down memory lane somehow,” he replies. 

You snort in response and dig back into the box for something else.

Dean’s phone buzzes in his pocket. He checks and sees a text from Sam, asking if he’s with you.

Yeah, we’re going through Bobby’s stuff. I can come help. No need. It’s not that much. …Dude. What’re you doing? What? We’re good. Just catching up. All of a sudden you two are civil? I guess. It’s no big deal. We’ll be back in a few minutes. Ok. Just…be smart about this.

Dean frowns, resenting what his brother is insinuating. He glances up at you.

You haven’t noticed his silent conflict. You’re just looking through old baseball cards and faded trucker hats, rusty tools and piles of weathered flannel.

By the time you get to the third box, over an hour has passed, the bottle of scotch is almost empty, and you’re laughing harder and freer at the stories about Bobby that Dean’s pulling out easier than the next object. You haven’t even noticed that his knee rests against your thigh, or that you occasionally grab his forearm when something he says makes you particularly giggly.

It’s kind of cute that you still do that, but he keeps that thought locked in deep. His smile starts to hurt the corners of his cheeks, though.

Eventually, what you find at the bottom of the last box hits you so hard behind the ribs that it steals your breath. It’s a picture of you and your mom when you were around seven years old: your first year in this cabin, on this ranch.

To you it had seemed like a fun adventure, and so much cooler than your little boring apartment in Salida. Here, there were horses and cows and Sunday barbecues hosted by John Winchester himself.

It was on one of those Sundays that you met Dean, with all those freckles dotted across the bridge of his nose and cheeks, and the purest kind of happiness in his green eyes while he ate a slice of peach cobbler with a scoop of melting homemade ice cream. You remember him setting his own plate aside for a while though, just to comfort his six-year-old brother when his ice cream rolled off the side of his bowl into the dirt. Dean ended up slotting his own ice cream into Sammy’s bowl.

Bobby clocked what happened out of the corner of his eye. In the end, he was the one to slip you and Dean an extra scoop.

Your dad didn’t miss much, at least back then.

“I don’t get it, you know,” you say, somewhat shakily. “When we were kids, Dad was my safe place. Sure, he was gruff and curmudgeonly sometimes, but he was gentle too. He always looked out for me. I understand that shit didn’t work out between him and Mom, but I did try calling him. Years of five-minute conversations that never went anywhere, because he had to get back to the ranch.”

Your lips tremble and you try to blink past the sting, but the dam is already full to bursting, and your walls are failing all over again.

Dean watches you, and he actually listens as his heart grows heavier.

“I was a student. For a long time, I couldn’t afford to fly back to Salida,” you admit. “But he never once came out to visit. He didn’t even go to my college graduation. He showed up to Mom’s funeral. That’s it. I had to call the cemetery, the church, arrange the burial. I had to figure it all out by myself. And I get it, she left him. But he didn’t have to leave me too.”

You press your fingers over your mouth, as if that can stop the hurt from spilling out. You find sympathy in Dean’s eyes, but he doesn’t do what you expect. He rifles through the same collection of memories and pulls out a thin, white box.

Inside is a thin silver chain necklace with a small rose pendant. He lets the chain fall into your hand.

“He was going to give you this at your graduation,” Dean says. “I only know because he was hella fucking drunk one night, and he told me.” 

You laugh a little through unshed tears. You marvel at the necklace; it’s simple, dainty even, but beautiful. 

“Your mom told him not to go,” Dean says, earning your soft shock. “He hadn’t helped you pay for college, so in her mind, he didn’t have a right to see you. At least, that’s what he said happened.” 

“What?” you frown, rubbing the small pendant between your fingers. “I…can’t believe she said that.”

You had a partial scholarship and a work study job, but you wouldn’t have gotten through college without your mom. Living in San Diego hadn’t been easy at first, financially, and your mother was a nurse. You still don’t know how she managed it, but she always came through for you when it was time to pay for the next semester, and even for your textbooks.

You understood that even a Foreman didn’t make a hefty salary. It was part of the reason your mom gave you for leaving your dad. She didn’t come from a ranching family, and she had never wanted to spend her life on a ranch either, let alone one that your parents didn’t own.

In her words, “It’s hard to build a life on someone else’s land.”

She told you that she wanted more for you, and more for herself. Bobby hadn’t been willing to leave Winchester Ranch.

“He was dedicated to it. In some ways it was admirable, but in others…” she’d said, with an edge of bitterness.

You never really understood it. You realize now that you hadn’t tried hard enough. 

“I didn’t care about the fucking money or who paid for what. I just wanted him to be there,” you quietly confess. “But I know that’s a two-way street. I wasn’t there for him either.”

You look up at Dean, meeting his gaze.

“You were right,” you say, as emotion begins to choke you. “He had a goddamn heart attack, and I would’ve never known.”

Your shoulders shake as the first sob wracks through your body, but you soon find warmth and a familiar comfort in Dean’s arms.

“Okay, sweetheart. Come ‘ere,” he says, as he holds you close. There’s something different in his voice. Deep and a little coarse, but gentler. It’s the anchor you need right now, and you cling to it. You cling to him.

“It’s not your fault, okay? Seems like Bobby made his choices too,” Dean says. 

He tucks your head under his chin and briefly closes his eyes as he strokes your back. He feels every hiccup and unsteady breath in you, feels your tears dampening his shirt. His lips press to the crown of your head. Your fingers tangle in the green flannel at his back.

As you begin to relax after crying yourself out, your curled fingers smooth out into warm hands that release his shirt, but ultimately don’t move far, laid flat against his chest. He brushes frizzy strands of hair away from your face and behind your ear. You slowly look up to meet his eyes, with tears clinging to your lashes. Your lipstick is smudged, but you’re still a wonder to him.

It may just be the booze, but he remembers exactly how this used to feel. It cracks open something he’s been paving over, brick by brick. Year after year. He didn’t think this was what it would take to see you again.  

“Jesus,” he murmurs, brushing your cheek with his thumb. “You’re still so fucking beautiful. More, even.”

Your mouth parts with a hint of surprise, and a telling intake of breath. Your lashes lower as your gaze falls—to his lips.

What the hell is this?

You pull away from him, gently guiding his hand down.

He feels the sting of rejection, but also, his shame.

“’M sorry,” he says, looking away.

“…Yeah,” you say eloquently. You feel a prickle of guilt yourself as you wipe your cheeks.

You push yourself off the couch, but your body doesn’t cooperate well. Hard liquor hasn’t been your poison for a hot minute, whiskey least of all. Clearly, it’s remained a favorite of Dean’s.

But he’s far more than a memory you can shove to the back of your mind, especially when he gets up with you—to hold you and stop you from falling. He looks into your eyes, and the conflict in his makes you morbidly curious. What you would give to know what he’s thinking. 

“Just tell me one thing,” he says. “Does he treat you right?”

You frown. “Excuse me?”

His brows raise in challenge. “Come on. Work is work, but how’s he not gonna at least show up here for you?”

It probably makes him some kind of hypocrite, and he fights the voice inside that tells him he’s an idiot. An asshole.

But all you give him is the soft bite of your words.

“Not that it’s any of your business, but like I told you, our jobs are demanding,” you reply, crossing your arms. “He can be very considerate.”

Dean quirks a wry smile. He glances down at that ring, oval-shaped and vintage, putting it mildly. It would look real nice on his Great Aunt Matilda.

“Yeah, with this, huh?” he says, grasping your left hand. “Tell me this is some kind of kooky family heirloom.”

You slip your hand out of his. “He found it at an estate sale.”

“Oh, I believe you,” Dean chuckles. He taps the humble pendant that now has a place above your heart, after he helped you figure out how to put on the necklace it belongs to. “That’s more your speed.”

“How would you know?” you retort, batting his finger off. “It’s been all this time, and you think you still know me?”

You really do walk away from him now, beelining toward the door…

Well, you would have. You will. But his audacity truly is monumental, and after how he treated you this morning, this really is too much for you to wrap your head around. It derails what would’ve been a highly justified storm-out, and compels you back to face him in frustration.

“What’re you trying to do, Dean, spin my head around?” you snap. “You’re the one who broke my heart first. You don’t even know how much you messed me up.”

The confession escapes you before you can cram it back in, shocking you as well as him.

But it’s true.

Years. It had taken you years to get over him, your best friend. Your first real love.

Dean’s amusement faded the more you spoke.

“I know,” he says. And the admission costs him. Under the layers of bravado, bitterness and hurt, there’s the truth. “I was a stupid kid back then, who didn’t know how to let you go.”

You shake your head in denial. Your heart hurts, probably because it never healed right the first time.

“That’s bullshit,” you say. “You didn’t have to let me go. That was your choice.”

“Yeah, I did,” Dean says, with a newfound certainty that dims the light from his eyes. “You had a life ahead of you, sweetheart. Mine was always gonna be on this ranch.”

For a moment, you’re stunned where you stand.

Until reason and doubt start to compete for new ground in your mind.

He’s still making excuses, you think. He could’ve come with you to college. You told him that then, and even if his father tried to nail his boots to the ground, Dean never even called you once after you left. Where was this apology when it would’ve mattered?

“Jesus Christ, Dean…”

You rub your forehead at the headache you already feel coming on. You’re probably drunk, in fairness.

“Why are you telling me all this now?” you ask.

He sighs and rakes a hand through his hair, then rubs his eyes as well.

“Good question,” he chuckles slightly. He sobers when he meets your eyes again. “You told the truth today at the funeral. It’s only fair I give you the same courtesy.”

“Courtesy. Is that what this is?” you challenge.

“It’s an apology,” he says. “And uh, it’s goodbye, stranger, I guess.”

“Goodbye,” you echo. Though you’re unable to stop yourself from glancing down at his lips again. Then back to his eyes, despite the glassiness in yours. A hitch in your breath. “I guess it is.”

Dean sees it, another spark of your tears. He still hates it, both selfishly and unselfishly.

He can’t help but try to give you the stability you need. First, by his slow attempt to hold you, brushing his thumbs against your arms. Your mouth parts, but you don’t pull away.

He bows his head and follows the deep-seated need in his gut, urging him to press his lips to yours.

You breathe in sharply through your nose, but your fingers clench in his shirt again, near his collar. Your body melts willingly against his, like a muscle memory you thought you lost.

Then, the brush of his tongue short-circuits your brain. His hand moves down to the small of your back and presses you into him, eliciting tingles down your spine, and a blooming, pulsing heat between your legs.

You whimper into his mouth, and his hold tightens a fraction.

You pull back for a moment, panting for air. Your eyes meet his incredulously.

He steels himself, waiting for a slap, or at least a push.

You don’t have it in yourself to give him either one. Your heart clenches painfully, because despite the guilt and shame you already feel, something inside you, deeply vulnerable and frayed, needs this.

You tell yourself it’s just one more kiss.

He meets you halfway when you lean up to claim his lips. He claims you back, his hands once again molding to your waist, his arms caging you in, his hand sinking into your hair.

One more turns into him backing you up against the wall. You grab onto his shoulders for leverage, then his hair as his lips veer away from yours to blaze a hot, wet trail down your neck. Your moan is perfect in his ear, rattling down his spine and right to his cock.

You feel him heavy and thick through his jeans, pressing against you. His hand slips up your thigh, squeezing plush flesh as he goes. He bunches the skirt of your dress up to your hips.

“Unzip me,” you tell him, through hushed tones and heated breaths.

Dean nods, turning you around and brushing your hair out of the way so he can drag the zipper down in a slow, torturous tease. His eyes drink in every inch of your skin, but there’s nothing sexier to him than the way you brush down the sleeves and slip out of the dress the rest of the way. The fabric falls around your ankles, and you step out of them in your tall heels. Dean gets the full view of your lace panties, then the matching bra when you turn back around.

He catches your little intake of breath, like you’re guarding yourself before he sees you. He smiles and pulls you back in by your waist.

“Like I said, fucking beautiful,” he says, his gaze roaming your face.

Your lips tug at a smile as you meet his stare, but he finally renders you without a snappy word to say. He takes that win and revels in it as he kisses you.

You touch him more confidently than he remembers, dragging your nails down the back of his neck, sucking his tongue into your mouth, down to grabbing onto his belt and popping the buckle open. He follows your lead and helps you loosen his belt and jeans, but his boots and your heels are the first to form a haphazard pile on the way into the bigger bedroom, where his spare sheets and an old comforter line the bed.

He wasn’t lying to you when he said he’s been staying over here for the past few days. Not only so that he could clean up, but because he needed to clear his own head. Bobby’s death shook everyone, but it hit Dean in a way he hadn’t expected. He hasn’t told anyone this, but it was like losing a second father.

It reminded Dean of his regrets—his biggest one of all being you.

Despite how it looks, he knows it’s wrong to touch you. He knows it’s selfish to want you. But he hasn’t allowed himself to want anything in such a long time, and he thinks he might be able to right some old wrongs while he’s busy committing new ones.

After he lays you on the bed underneath him, Dean kisses his way along the column of your throat, down between your breasts. He slips a hand underneath you to unhook the pretty lace bra, and your back arches, giving him room. 

You really have grown up beautifully, even your boobs. Good for you, and good for him. Dean recommits them to memory as his tongue lavishes one of your nipples, while his right hand rolls the other between his thumb and forefinger. You sigh his name and slip your fingers through his hair, scratching his scalp with your nails. But your fingers hook on his flannel next.

“Take this off,” you breathe. “Want to see you too.”

Dean hesitates, but concedes to taking off his outer flannel. His undershirt stays on, even though you tug on it next. He aims to distract you by moving further down your body, laying open-mouthed kisses down your ribs and stomach, and over your mound, after he slips off your panties. He glances up between your legs and shoots you a mischievous grin.

“I used to love the way you tasted,” he says. “Those little sounds you made, the way you’d buck against my chin and scream my name… Let’s see if we can rock another sequel, huh, sweetheart?” 

“Dean,” you gasp, as his fingers slip between the folds of your pussy. They find slick arousal and heat.

“Jesus,” he murmurs. “You’re soaking wet.”

He bites his lower lip as his thumb searches, then finds your clit. Your hips start to writhe as you moan, grinding against his hand. He smirks in satisfaction before he lowers down. He moves your left thigh over his shoulder, and he feasts.

Your mouth falls open in a near silent cry, and your hips nearly come off the bed as you feel his tongue replace his fingers on your clit. Those long digits slip inside your hot channel. Hunger pools in your lower belly as your inner walls clench on him, desperately needing friction. Your breaths deepen as your free hand goes to your breast, toying with a hard nipple while you savor the sensations Dean’s giving you with his mouth and skilled fingers.

He curls his fingers and strokes you deeply, searching, exploring, until he finds that most sensitive place within your inner walls that has your body shuddering like an accordion. You grab a fistful of his hair as you buck hard against his mouth, a choked scream falling from your lips.

After withdrawing his fingers and wiping his mouth and nose, he presses a kiss into your inner thigh as you still tremble with the aftershocks of your orgasm.

He moves back up your body, and you take his face in your hands to kiss him deeply.

“What’s the verdict?” he teases afterward.

“You’ve gotten better,” you admit.

You sit up, intending to return the favor as your hands roam down his chest and underneath his shirt. He feels toned from long hours of hard labor and horse riding, but he stills your hands from grasping at the edge of his shirt. You’re confused, but he quickly guides you into turning over in the bed.

He kneels behind you as his steady hands continue to map every inch of your body. He caresses your sides, across your middle, and back up to your breasts while he kisses along your neck, then down your shoulder. There’s more calm confidence in his touch than he had at 20 years old, certainly more strength and more callouses, but it’s a delicious friction. And it’s a feeling that he absolutely has you enveloped in his arms, within his broad frame. You hang onto him on reflex.

Two of his fingers dip back into your pussy, circling your clit. You hang onto his arm as your body gives way to a moan. Arousal begins to pulse deep inside you again, but this time, you need his cock. You want to know if he’s improved there too. He seems to remember your body well enough.

“Dean…just fuck me,” you whisper coarsely. “Please…”

Before I lose my nerve.

“I gotcha, sweetheart,” he says, in a voice like old scotch and honey. Its depths make prickles of heat flash across your skin as fabric rustles. You assume he’s finally stripping off the rest of his clothes. You catch a glimpse over your shoulder of him tossing his shirt and boxers to the floor, but soon, the heat of his presence returns as he lines himself up at your entrance. His cock finally pushing inside you from behind makes your thighs tremble. Your nails dig into the mattress sheets.

“Dean,” you gasp. He stretches you so fucking good.

“You’ve got it, baby. Every damn inch, doing so good,” he says, breathing hard into your neck. His teeth graze your shoulder, making you shudder and push into him on reflex, sheathing him nice and snug inside. Already the walls of your cunt tremble around his cock.

Dean keeps his promise; it’s dewy skin against skin as holds you to him while he fucks you, slow, deep, and powerful, but never painful. Never too much.

He asks you what you want—faster or slower, rougher, or easier rhythm. You tell him you want him exactly how he is: fucking perfect.

And that night, it is fucking perfect.

Almost.

Both of you have left your cell phones on the kitchen table. They’ve buzzed almost half a dozen times, each with text messages and a handful of calls.

Your little black dress collects dust on the floor along with his jeans and flannel.

In the morning, long after he should, Dean wakes up nice and easy.

He just ends up waking alone.

AN: 🫣 Sorry loll. If you think those twists were fun, then get ready for a whole messy love triangle when Brady re-enters from Stage Left. 😬 (And are you curious about Dean and reader's past?)

Next Time:

What have I done?

Okay, you were drunk, but not that drunk.

You were in pain. Reckless. Selfish.

Shame invades your body and settles into your heart. All you can do is slowly, silently slip out of the bed without disturbing Dean. After reclaiming your clothes from the dusty floor and getting dressed, you hold back tears as you try to leave the tangle of desire and old memories, both beautiful and painful, behind you in that room. All you take with you is your phone and the silver necklace you already wear.

Although you wait to put on your heels until you get outside the cabin, that big stretch of hill up ahead to the main house is daunting.

“Mornin’.”

Your head turns sharply at the voice. You shouldn’t be surprised that someone’s already up this early, let alone one of the ranch hands. Benny. He’s tall and broad, like Dean, though with reddish brown hair and a thicker beard. He’s already dressed for the day in jeans and a long-sleeved shirt, drinking his coffee as he leans against the bunkhouse wall. You nod back at him with an awkward smile. 

“How you plan to get up the hill in those pumps?” he asks.

You sigh. “I don’t.”

You’re about to execute the worst walk of shame you’ve ever done, but at least it’s only for an audience of one. You slip off the heels and let the ankle straps dangle from your fingers as you walk barefoot on wet, dewy earth, all the way back up to the house. 

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ᯓ✍🏽 Part 3 coming to Tumblr: August 16

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Dean Winchester Series List

Dean Winchester AU Stories

Dean Winchester Masterlist

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Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

Yeah, it can be unpleasant, especially when you're not used to it. I had some experience:) I mean it was more or less fine when I was a child, but I haven't been in a stable for years, so it'd probably made me gag too 😀

Oh really? That's cool! I've only seen horses a handful of times too since I've always lived in the city lol

The fact that Dean was her first love makes their story even more sentimental and hard to forget, I guess.

Absolutely. She and Dean have known each other since they were 7 and 9 years old, respectively, and he was her first love and first real boyfriend (you'll see more about that soon), so their breakup and the way it happened really affected her.

"A few minutes", my ass😂 Sam, won't you check on them?

lmfao exactly 😂 he's assuming reader and Dean will be mature adults about this, but he's proved wrong lol

I bet he was unbelievably cute back then:)

Can you imagine? With his little freckles 🥰

I just realised he's not afraid of women's tears. A good quality.

No, not when it comes to her 😉 but he certainly doesn't like to see them ❤️‍🩹

Our man, I love him. Obviously it's not his business but I love him for wanting to know. Maybe it's his jealousy, but I also want to believe he just cares.

It's a bit of both in this case loll. He would never admit to being jealous, especially because he doesn't really have a right to be, but he also obviously still cares 💕

Is he hiding something? 🤔

Love them:D you know, you always write some phrases that makes me fall in love even at the very beginning:)

Aww haha I love that, thank you!! Despite what they're doing is technically wrong, I hoped to create parts that made you swoon regardless 😝

🙁 Predictable, though. Now she's full of guilt. And the most difficult part of the story starts here 😂 Of course I'm curious about Dean's and reader past? Is there a person who can say "no" to this? Btw, I agree - technically it's cheating, but since they love each other and I'm not sure Brady loves her, don't know him enough, so it doesn't feel like betrayal to me. But the fact she feels ashamed is... human? It'd probably be worse if she didn't.

Yeeep, she's feeling mighty guilty, and all the complicated drama spins from here in this fun little triangle. 😂

hahaa fair enough! There's a lot of juicy parts of their past that will be unraveled as we go along. And you'll learn more about her and Brady's relationship along the way, of course, and what cracks might be lying in wait there. It's natural that she feels guilty, because she does care about Brady. She and Dean were caught up in a very vulnerable moment and feelings (with some alcohol to rid them of some inhibitions lol)

I like that she's barefoot:) Probably it's uncomfortable, but sounds good as an idea.

hahaaa it paints quite a visual!

Thank you! I feel like they're my second favourite to Subtext (at least if we talk about your recent stories, and I hope it won't offend. I love the ones I've read, all of them, but each story feels different).

1: Sweet Home, Colorado

2: Too Close to the Heat

3: Nature, Nurture, Heaven & Home ℧ Read now on Patreon! || Tumblr: August 16

4: My Diamond is Too Rough 🌹 Read now on Patreon! || Tumblr: August 23

5: Time Bent Like an Hourglass ℧ Read on Patreon: August 14 || Tumblr: August 30

6: Loose Ends & Torn Pages 🌹 Read on Patreon: August 21 || Tumblr: September 6

7: Word Gets Out When You Get Around ℧ Read on Patreon: August 28 || Tumblr: September 20

8: Every Moment's a Crime

9: What We Said and What We Meant

10: Hear Your Heart Beat Next to Mine

11: Wait for the River to Roll

12: Pay No Mind to the Battles You've Won

13: It'll Take a Lot More Than Words & Guns

l4: It's a High Price, Paid in Blood

15: The Roots Through Southern Ground

16: Brave the Forests, Brave the Stone

17: Sunshine on the Water

ᯓ✍🏽 Series in progress...

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Dean Winchester Series List

Dean Winchester AU Stories

Dean Winchester Masterlist

Main Masterlist

Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

John's famous barbecue pit spins the mouthwatering smells of smoked meats. The tables are lined up and filled with buttery cornbread, potatoes done three different ways (mashed, roasted, and casseroled), salads, slaw, carrots and corn, wild rice, homemade dinner rolls and garlic bread, and no less than five different flavors of pie. You spy Dean tucking into his third slice of cherry. Evidently, it’s still his favorite. A piece of pastry crust flecks from his lower lip as he jumps in with an old story.

“So I’m maybe…twelve, thirteen. Bobby’s trying to show me how to fix this patch of barbed wire fence. Because I’m young and stupid, I get it in my head to jump over it while the wire’s slack,” Dean starts.

Sam and couple of the cowboys, Benny and Cas, are already smirking, chuckling a little, shaking their heads. They’ve definitely heard this one before, and this time, you have too. A smile curves your lips behind the rim of your glass of whiskey and Coke.

“I make it over, but my leg gets caught in the slack, and I just go down hard, eating the damn dirt,” Dean says. He mimes the impact of his body hitting the ground, complete with admittedly impressive sound effects. “But now the wire’s tight. Rips through my jeans, my ankle, blood soaking through. But, uh, Bobby calms me down, you know. He takes out his tool belt, and he says, ‘It’s all right, son. That’s why God made pliers, for idjits like you.’”

Laughter ripples across the table. Even John smiles, shaking his head.

“Well, he cleaned me up best he could and helped me back up on my horse,” Dean says. His grin is warm, and his gaze spans far beyond his beer. “Dad didn’t even have to lecture me. You remember what you said?”

John nods in amusement. “‘Your own body’s gonna do the punishing for me, son.’”

“Right. My ankle was busted for three weeks. Couldn’t ride, couldn’t do shit,” Dean says with a chuckle. “And it was summer too.”

At least he didn’t have to go to school, but for a boy like Dean, being cooped up in the house was three weeks of misery. All he could do was watch from his bedroom window while you and Sam ran off to ride your bikes in town or go swimming in the river.

He looks down toward the end of the table, wanting to see if you remember those days like he does. What he finds is your empty seat. His eyes run a search—and eventually catch you making your way over to the barn. His brows furrow in confusion, but as the conversation spins and Benny takes over the reminiscing, Dean gets up from the table, ignoring the little warning tug in his gut.

“Gonna get another beer,” he says.

But Sam’s perceptive gaze follows him. While you venture into the barn, Sam sees his brother’s projected path all too clearly.

The smell of horse makes you gag a little, but after you enter the barn and switch on the light, yet another wave of nostalgia blasts you in the face. You recognize that tack and tool shelf on the right-hand corner, and the rack of shotguns and rifles on the far left. You know these stalls, and you greet each of the horses like old friends, even though most of them are new ones.

You stop at one of the middle stalls on the right, clicking your tongue at an older horse. His coat is a deep coffee brown, dappled with white on his hindquarters.

“Dakota! Look at you, handsome.” You smile brightly. “Remember me?”

He blinks at you with those dark eyes, and he meanders a bit closer to the half door. You offer a loosely closed fist for him to inspect. When he does, you think it’s with some familiarity as he sniffs your hand all over. Or maybe he’s just smelling the apple pie glaze you licked off your finger earlier.

You laugh lightly and take a chance on petting the side of his neck. He lets you do it, a kind older statesman. Before you left, you had helped your dad break this horse in.

“He remembers you.”

You turn your head toward the door, flinching slightly in surprise. You didn’t even hear Dean come into the barn. His scuffed boots cross the distance leading him to you. Dark wash jeans and a black buttoned-down shirt are probably the extent of his cleaning up for the occasion, but the ensemble does suit him better than a proper suit would.

“It all looks the same,” you say quietly.

“That’s because it is,” Dean replies. His lips pull at a smirk as he points to the tool shed. “Like that dusty back room where we used to make out.”

You roll your eyes, but you can’t help the way your gaze draws to his calloused hands and long fingers. Your cheeks begin to prickle with warmth, but you refocus on his face, and unfortunately, that familiar grin. You’re sure that face has gotten him plenty of action since then.

“You do remember I have a fiancé,” you say.

Dean nods, holding up a placating hand. It slips into his pocket as he leans against a support beam. “Yeah, you never said where that guy was today.”

“Working,” you reply defensively. “We’re in the middle of a big project, and we can’t afford to drop the ball.”

“You two work together?”

“Yeah, for his father’s company.”

“Doing what?”

You hesitate. It seems like Sam hasn’t spoken to Dean yet about the offer either, but in this case, you’re grateful for it.

“Land development. His father is co-CEO and head of the Legal team. I help scope out properties and propose new projects,” you say.

Dean quirks a brow. “Land development, huh? Not what I would’ve imagined.”

His tone annoys you, making you slightly more tense, but you’ve already had this argument with Sam. You don’t have to explain yourself to this man.

“It’s not what I thought I’d end up in either, but if you think it’s hard to be a rancher, try being able to pay rent in California. We’re all just trying to survive, Dean,” you say.

At that, he actually nods more sincerely.

“Guess that’s fair. But it looks like you’re more than surviving now. You’ve got a friggin’ golf ball on your finger,” he says, gesturing at you, and more specifically your engagement ring.

You roll your eyes. “It’s not that big.”

The way he snorts earns a reluctant smile from you.

“How long you known the guy?” Dean asks.

You give him a shrewd look. He’s very curious about your personal life, but you can’t deny that you’ve been wondering what the past 12 years have made of him.

“About eight months,” you reply.

His brows raise almost as high as his hairline. “Eight months? When did he pop the question?”

“…A few weeks ago,” you say, albeit with some hesitation. “What?”

Dean shakes his head. “Nothing, I guess. Whirlwind romance.”

“And what about you?” you counter, fighting a blush. “No girlfriend?”

Dean chuckles. “Oh, I have plenty of friends. Just no time for the whirlwind.”

“I’m sure,” you say wryly. “Things really don’t change much around here.”

It’s a touch snider than you mean it to be. You don’t actually want to pick another fight. Frankly, you don’t have the emotional energy.

But even though Dean gives you a certain look, to your surprise, he doesn’t want to snipe anymore either. He just sighs.

“All right, come on. There’s some of Bobby’s stuff that you might want to look through,” he says, ushering you to follow him.

You do so reluctantly, over to the Foreman’s cabin.

The Foreman wrangles the other ranch hands, and he’s the Ranch Manager’s second-in-command. Bobby held that position for 23 years, starting from back when John was managing all operations himself. You used to live in this cabin with your mom and dad, back when they were together. 

Dean would later take your virginity when you turned 18—in the glorified closet that used to be your bedroom.

At least he doesn’t bring up that little anecdote as he leads you to the small, four-seater dining table. It has a few boxes stacked on top of it, probably what’s left of your father’s belongings. The rest has been cleared out except for a couch, an old wood coffee table, a TV on a stand, and some supplies in the kitchen. There are some signs of life here though, like a half-drunk beer on the coffee table, an empty box of pizza on the kitchen counter, and some crumpled napkins. Dean notices your observing gaze.

“I’ve been hanging out here the past few days. Cleaning the place up took a while, but uh, sometimes it’s nice to get away from the main house,” he says.

“I could see why. Thirty-two and still living with your daddy,” you teasingly remark.

Dean shoots you an amused brow raise, but he brings the first box to the living room coffee table and slides it toward you.

“Take whatever you want. He doesn’t have any other family, so I’m not sure what to do with the rest,” he says, rubbing a hand at the back of his neck.

Throwing it away feels wrong, or so his tone says. You nod in agreement and start looking through the box. The first thing you find is a large bottle of gold label scotch.

“Wow,” you say.

“That’s on brand,” Dean says, with a smirk. He eyes you. “We should probably crack it open, in Bobby’s honor, of course.”

Your lips tug at a smile. You hand it over, and Dean twists off the cap to take a swig. He offers it back to you, and you accept it dubiously after sitting beside him on the couch.

“You know we’re not teenagers anymore, right?” you say, but you still sip straight from the bottle just like he did, grimacing at the burn down your throat.

“We gotta lubricate this trip down memory lane somehow,” he replies. 

You snort in response and dig back into the box for something else.

Dean’s phone buzzes in his pocket. He checks and sees a text from Sam, asking if he’s with you.

Yeah, we’re going through Bobby’s stuff. I can come help. No need. It’s not that much. …Dude. What’re you doing? What? We’re good. Just catching up. All of a sudden you two are civil? I guess. It’s no big deal. We’ll be back in a few minutes. Ok. Just…be smart about this.

Dean frowns, resenting what his brother is insinuating. He glances up at you.

You haven’t noticed his silent conflict. You’re just looking through old baseball cards and faded trucker hats, rusty tools and piles of weathered flannel.

By the time you get to the third box, over an hour has passed, the bottle of scotch is almost empty, and you’re laughing harder and freer at the stories about Bobby that Dean’s pulling out easier than the next object. You haven’t even noticed that his knee rests against your thigh, or that you occasionally grab his forearm when something he says makes you particularly giggly.

It’s kind of cute that you still do that, but he keeps that thought locked in deep. His smile starts to hurt the corners of his cheeks, though.

Eventually, what you find at the bottom of the last box hits you so hard behind the ribs that it steals your breath. It’s a picture of you and your mom when you were around seven years old: your first year in this cabin, on this ranch.

To you it had seemed like a fun adventure, and so much cooler than your little boring apartment in Salida. Here, there were horses and cows and Sunday barbecues hosted by John Winchester himself.

It was on one of those Sundays that you met Dean, with all those freckles dotted across the bridge of his nose and cheeks, and the purest kind of happiness in his green eyes while he ate a slice of peach cobbler with a scoop of melting homemade ice cream. You remember him setting his own plate aside for a while though, just to comfort his six-year-old brother when his ice cream rolled off the side of his bowl into the dirt. Dean ended up slotting his own ice cream into Sammy’s bowl.

Bobby clocked what happened out of the corner of his eye. In the end, he was the one to slip you and Dean an extra scoop.

Your dad didn’t miss much, at least back then.

“I don’t get it, you know,” you say, somewhat shakily. “When we were kids, Dad was my safe place. Sure, he was gruff and curmudgeonly sometimes, but he was gentle too. He always looked out for me. I understand that shit didn’t work out between him and Mom, but I did try calling him. Years of five-minute conversations that never went anywhere, because he had to get back to the ranch.”

Your lips tremble and you try to blink past the sting, but the dam is already full to bursting, and your walls are failing all over again.

Dean watches you, and he actually listens as his heart grows heavier.

“I was a student. For a long time, I couldn’t afford to fly back to Salida,” you admit. “But he never once came out to visit. He didn’t even go to my college graduation. He showed up to Mom’s funeral. That’s it. I had to call the cemetery, the church, arrange the burial. I had to figure it all out by myself. And I get it, she left him. But he didn’t have to leave me too.”

You press your fingers over your mouth, as if that can stop the hurt from spilling out. You find sympathy in Dean’s eyes, but he doesn’t do what you expect. He rifles through the same collection of memories and pulls out a thin, white box.

Inside is a thin silver chain necklace with a small rose pendant. He lets the chain fall into your hand.

“He was going to give you this at your graduation,” Dean says. “I only know because he was hella fucking drunk one night, and he told me.” 

You laugh a little through unshed tears. You marvel at the necklace; it’s simple, dainty even, but beautiful. 

“Your mom told him not to go,” Dean says, earning your soft shock. “He hadn’t helped you pay for college, so in her mind, he didn’t have a right to see you. At least, that’s what he said happened.” 

“What?” you frown, rubbing the small pendant between your fingers. “I…can’t believe she said that.”

You had a partial scholarship and a work study job, but you wouldn’t have gotten through college without your mom. Living in San Diego hadn’t been easy at first, financially, and your mother was a nurse. You still don’t know how she managed it, but she always came through for you when it was time to pay for the next semester, and even for your textbooks.

You understood that even a Foreman didn’t make a hefty salary. It was part of the reason your mom gave you for leaving your dad. She didn’t come from a ranching family, and she had never wanted to spend her life on a ranch either, let alone one that your parents didn’t own.

In her words, “It’s hard to build a life on someone else’s land.”

She told you that she wanted more for you, and more for herself. Bobby hadn’t been willing to leave Winchester Ranch.

“He was dedicated to it. In some ways it was admirable, but in others…” she’d said, with an edge of bitterness.

You never really understood it. You realize now that you hadn’t tried hard enough. 

“I didn’t care about the fucking money or who paid for what. I just wanted him to be there,” you quietly confess. “But I know that’s a two-way street. I wasn’t there for him either.”

You look up at Dean, meeting his gaze.

“You were right,” you say, as emotion begins to choke you. “He had a goddamn heart attack, and I would’ve never known.”

Your shoulders shake as the first sob wracks through your body, but you soon find warmth and a familiar comfort in Dean’s arms.

“Okay, sweetheart. Come ‘ere,” he says, as he holds you close. There’s something different in his voice. Deep and a little coarse, but gentler. It’s the anchor you need right now, and you cling to it. You cling to him.

“It’s not your fault, okay? Seems like Bobby made his choices too,” Dean says. 

He tucks your head under his chin and briefly closes his eyes as he strokes your back. He feels every hiccup and unsteady breath in you, feels your tears dampening his shirt. His lips press to the crown of your head. Your fingers tangle in the green flannel at his back.

As you begin to relax after crying yourself out, your curled fingers smooth out into warm hands that release his shirt, but ultimately don’t move far, laid flat against his chest. He brushes frizzy strands of hair away from your face and behind your ear. You slowly look up to meet his eyes, with tears clinging to your lashes. Your lipstick is smudged, but you’re still a wonder to him.

It may just be the booze, but he remembers exactly how this used to feel. It cracks open something he’s been paving over, brick by brick. Year after year. He didn’t think this was what it would take to see you again.  

“Jesus,” he murmurs, brushing your cheek with his thumb. “You’re still so fucking beautiful. More, even.”

Your mouth parts with a hint of surprise, and a telling intake of breath. Your lashes lower as your gaze falls—to his lips.

What the hell is this?

You pull away from him, gently guiding his hand down.

He feels the sting of rejection, but also, his shame.

“’M sorry,” he says, looking away.

“…Yeah,” you say eloquently. You feel a prickle of guilt yourself as you wipe your cheeks.

You push yourself off the couch, but your body doesn’t cooperate well. Hard liquor hasn’t been your poison for a hot minute, whiskey least of all. Clearly, it’s remained a favorite of Dean’s.

But he’s far more than a memory you can shove to the back of your mind, especially when he gets up with you—to hold you and stop you from falling. He looks into your eyes, and the conflict in his makes you morbidly curious. What you would give to know what he’s thinking. 

“Just tell me one thing,” he says. “Does he treat you right?”

You frown. “Excuse me?”

His brows raise in challenge. “Come on. Work is work, but how’s he not gonna at least show up here for you?”

It probably makes him some kind of hypocrite, and he fights the voice inside that tells him he’s an idiot. An asshole.

But all you give him is the soft bite of your words.

“Not that it’s any of your business, but like I told you, our jobs are demanding,” you reply, crossing your arms. “He can be very considerate.”

Dean quirks a wry smile. He glances down at that ring, oval-shaped and vintage, putting it mildly. It would look real nice on his Great Aunt Matilda.

“Yeah, with this, huh?” he says, grasping your left hand. “Tell me this is some kind of kooky family heirloom.”

You slip your hand out of his. “He found it at an estate sale.”

“Oh, I believe you,” Dean chuckles. He taps the humble pendant that now has a place above your heart, after he helped you figure out how to put on the necklace it belongs to. “That’s more your speed.”

“How would you know?” you retort, batting his finger off. “It’s been all this time, and you think you still know me?”

You really do walk away from him now, beelining toward the door…

Well, you would have. You will. But his audacity truly is monumental, and after how he treated you this morning, this really is too much for you to wrap your head around. It derails what would’ve been a highly justified storm-out, and compels you back to face him in frustration.

“What’re you trying to do, Dean, spin my head around?” you snap. “You’re the one who broke my heart first. You don’t even know how much you messed me up.”

The confession escapes you before you can cram it back in, shocking you as well as him.

But it’s true.

Years. It had taken you years to get over him, your best friend. Your first real love.

Dean’s amusement faded the more you spoke.

“I know,” he says. And the admission costs him. Under the layers of bravado, bitterness and hurt, there’s the truth. “I was a stupid kid back then, who didn’t know how to let you go.”

You shake your head in denial. Your heart hurts, probably because it never healed right the first time.

“That’s bullshit,” you say. “You didn’t have to let me go. That was your choice.”

“Yeah, I did,” Dean says, with a newfound certainty that dims the light from his eyes. “You had a life ahead of you, sweetheart. Mine was always gonna be on this ranch.”

For a moment, you’re stunned where you stand.

Until reason and doubt start to compete for new ground in your mind.

He’s still making excuses, you think. He could’ve come with you to college. You told him that then, and even if his father tried to nail his boots to the ground, Dean never even called you once after you left. Where was this apology when it would’ve mattered?

“Jesus Christ, Dean…”

You rub your forehead at the headache you already feel coming on. You’re probably drunk, in fairness.

“Why are you telling me all this now?” you ask.

He sighs and rakes a hand through his hair, then rubs his eyes as well.

“Good question,” he chuckles slightly. He sobers when he meets your eyes again. “You told the truth today at the funeral. It’s only fair I give you the same courtesy.”

“Courtesy. Is that what this is?” you challenge.

“It’s an apology,” he says. “And uh, it’s goodbye, stranger, I guess.”

“Goodbye,” you echo. Though you’re unable to stop yourself from glancing down at his lips again. Then back to his eyes, despite the glassiness in yours. A hitch in your breath. “I guess it is.”

Dean sees it, another spark of your tears. He still hates it, both selfishly and unselfishly.

He can’t help but try to give you the stability you need. First, by his slow attempt to hold you, brushing his thumbs against your arms. Your mouth parts, but you don’t pull away.

He bows his head and follows the deep-seated need in his gut, urging him to press his lips to yours.

You breathe in sharply through your nose, but your fingers clench in his shirt again, near his collar. Your body melts willingly against his, like a muscle memory you thought you lost.

Then, the brush of his tongue short-circuits your brain. His hand moves down to the small of your back and presses you into him, eliciting tingles down your spine, and a blooming, pulsing heat between your legs.

You whimper into his mouth, and his hold tightens a fraction.

You pull back for a moment, panting for air. Your eyes meet his incredulously.

He steels himself, waiting for a slap, or at least a push.

You don’t have it in yourself to give him either one. Your heart clenches painfully, because despite the guilt and shame you already feel, something inside you, deeply vulnerable and frayed, needs this.

You tell yourself it’s just one more kiss.

He meets you halfway when you lean up to claim his lips. He claims you back, his hands once again molding to your waist, his arms caging you in, his hand sinking into your hair.

One more turns into him backing you up against the wall. You grab onto his shoulders for leverage, then his hair as his lips veer away from yours to blaze a hot, wet trail down your neck. Your moan is perfect in his ear, rattling down his spine and right to his cock.

You feel him heavy and thick through his jeans, pressing against you. His hand slips up your thigh, squeezing plush flesh as he goes. He bunches the skirt of your dress up to your hips.

“Unzip me,” you tell him, through hushed tones and heated breaths.

Dean nods, turning you around and brushing your hair out of the way so he can drag the zipper down in a slow, torturous tease. His eyes drink in every inch of your skin, but there’s nothing sexier to him than the way you brush down the sleeves and slip out of the dress the rest of the way. The fabric falls around your ankles, and you step out of them in your tall heels. Dean gets the full view of your lace panties, then the matching bra when you turn back around.

He catches your little intake of breath, like you’re guarding yourself before he sees you. He smiles and pulls you back in by your waist.

“Like I said, fucking beautiful,” he says, his gaze roaming your face.

Your lips tug at a smile as you meet his stare, but he finally renders you without a snappy word to say. He takes that win and revels in it as he kisses you.

You touch him more confidently than he remembers, dragging your nails down the back of his neck, sucking his tongue into your mouth, down to grabbing onto his belt and popping the buckle open. He follows your lead and helps you loosen his belt and jeans, but his boots and your heels are the first to form a haphazard pile on the way into the bigger bedroom, where his spare sheets and an old comforter line the bed.

He wasn’t lying to you when he said he’s been staying over here for the past few days. Not only so that he could clean up, but because he needed to clear his own head. Bobby’s death shook everyone, but it hit Dean in a way he hadn’t expected. He hasn’t told anyone this, but it was like losing a second father.

It reminded Dean of his regrets—his biggest one of all being you.

Despite how it looks, he knows it’s wrong to touch you. He knows it’s selfish to want you. But he hasn’t allowed himself to want anything in such a long time, and he thinks he might be able to right some old wrongs while he’s busy committing new ones.

After he lays you on the bed underneath him, Dean kisses his way along the column of your throat, down between your breasts. He slips a hand underneath you to unhook the pretty lace bra, and your back arches, giving him room. 

You really have grown up beautifully, even your boobs. Good for you, and good for him. Dean recommits them to memory as his tongue lavishes one of your nipples, while his right hand rolls the other between his thumb and forefinger. You sigh his name and slip your fingers through his hair, scratching his scalp with your nails. But your fingers hook on his flannel next.

“Take this off,” you breathe. “Want to see you too.”

Dean hesitates, but concedes to taking off his outer flannel. His undershirt stays on, even though you tug on it next. He aims to distract you by moving further down your body, laying open-mouthed kisses down your ribs and stomach, and over your mound, after he slips off your panties. He glances up between your legs and shoots you a mischievous grin.

“I used to love the way you tasted,” he says. “Those little sounds you made, the way you’d buck against my chin and scream my name… Let’s see if we can rock another sequel, huh, sweetheart?” 

“Dean,” you gasp, as his fingers slip between the folds of your pussy. They find slick arousal and heat.

“Jesus,” he murmurs. “You’re soaking wet.”

He bites his lower lip as his thumb searches, then finds your clit. Your hips start to writhe as you moan, grinding against his hand. He smirks in satisfaction before he lowers down. He moves your left thigh over his shoulder, and he feasts.

Your mouth falls open in a near silent cry, and your hips nearly come off the bed as you feel his tongue replace his fingers on your clit. Those long digits slip inside your hot channel. Hunger pools in your lower belly as your inner walls clench on him, desperately needing friction. Your breaths deepen as your free hand goes to your breast, toying with a hard nipple while you savor the sensations Dean’s giving you with his mouth and skilled fingers.

He curls his fingers and strokes you deeply, searching, exploring, until he finds that most sensitive place within your inner walls that has your body shuddering like an accordion. You grab a fistful of his hair as you buck hard against his mouth, a choked scream falling from your lips.

After withdrawing his fingers and wiping his mouth and nose, he presses a kiss into your inner thigh as you still tremble with the aftershocks of your orgasm.

He moves back up your body, and you take his face in your hands to kiss him deeply.

“What’s the verdict?” he teases afterward.

“You’ve gotten better,” you admit.

You sit up, intending to return the favor as your hands roam down his chest and underneath his shirt. He feels toned from long hours of hard labor and horse riding, but he stills your hands from grasping at the edge of his shirt. You’re confused, but he quickly guides you into turning over in the bed.

He kneels behind you as his steady hands continue to map every inch of your body. He caresses your sides, across your middle, and back up to your breasts while he kisses along your neck, then down your shoulder. There’s more calm confidence in his touch than he had at 20 years old, certainly more strength and more callouses, but it’s a delicious friction. And it’s a feeling that he absolutely has you enveloped in his arms, within his broad frame. You hang onto him on reflex.

Two of his fingers dip back into your pussy, circling your clit. You hang onto his arm as your body gives way to a moan. Arousal begins to pulse deep inside you again, but this time, you need his cock. You want to know if he’s improved there too. He seems to remember your body well enough.

“Dean…just fuck me,” you whisper coarsely. “Please…”

Before I lose my nerve.

“I gotcha, sweetheart,” he says, in a voice like old scotch and honey. Its depths make prickles of heat flash across your skin as fabric rustles. You assume he’s finally stripping off the rest of his clothes. You catch a glimpse over your shoulder of him tossing his shirt and boxers to the floor, but soon, the heat of his presence returns as he lines himself up at your entrance. His cock finally pushing inside you from behind makes your thighs tremble. Your nails dig into the mattress sheets.

“Dean,” you gasp. He stretches you so fucking good.

“You’ve got it, baby. Every damn inch, doing so good,” he says, breathing hard into your neck. His teeth graze your shoulder, making you shudder and push into him on reflex, sheathing him nice and snug inside. Already the walls of your cunt tremble around his cock.

Dean keeps his promise; it’s dewy skin against skin as holds you to him while he fucks you, slow, deep, and powerful, but never painful. Never too much.

He asks you what you want—faster or slower, rougher, or easier rhythm. You tell him you want him exactly how he is: fucking perfect.

And that night, it is fucking perfect.

Almost.

Both of you have left your cell phones on the kitchen table. They’ve buzzed almost half a dozen times, each with text messages and a handful of calls.

Your little black dress collects dust on the floor along with his jeans and flannel.

In the morning, long after he should, Dean wakes up nice and easy.

He just ends up waking alone.

AN: 🫣 Sorry loll. If you think those twists were fun, then get ready for a whole messy love triangle when Brady re-enters from Stage Left. 😬 (And are you curious about Dean and reader's past?)

Next Time:

What have I done?

Okay, you were drunk, but not that drunk.

You were in pain. Reckless. Selfish.

Shame invades your body and settles into your heart. All you can do is slowly, silently slip out of the bed without disturbing Dean. After reclaiming your clothes from the dusty floor and getting dressed, you hold back tears as you try to leave the tangle of desire and old memories, both beautiful and painful, behind you in that room. All you take with you is your phone and the silver necklace you already wear.

Although you wait to put on your heels until you get outside the cabin, that big stretch of hill up ahead to the main house is daunting.

“Mornin’.”

Your head turns sharply at the voice. You shouldn’t be surprised that someone’s already up this early, let alone one of the ranch hands. Benny. He’s tall and broad, like Dean, though with reddish brown hair and a thicker beard. He’s already dressed for the day in jeans and a long-sleeved shirt, drinking his coffee as he leans against the bunkhouse wall. You nod back at him with an awkward smile. 

“How you plan to get up the hill in those pumps?” he asks.

You sigh. “I don’t.”

You’re about to execute the worst walk of shame you’ve ever done, but at least it’s only for an audience of one. You slip off the heels and let the ankle straps dangle from your fingers as you walk barefoot on wet, dewy earth, all the way back up to the house. 

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John's famous barbecue pit spins the mouthwatering smells of smoked meats. The tables are lined up and filled with buttery cornbread, potatoes done three different ways (mashed, roasted, and casseroled), salads, slaw, carrots and corn, wild rice, homemade dinner rolls and garlic bread, and no less than five different flavors of pie. You spy Dean tucking into his third slice of cherry. Evidently, it’s still his favorite. A piece of pastry crust flecks from his lower lip as he jumps in with an old story.

“So I’m maybe…twelve, thirteen. Bobby’s trying to show me how to fix this patch of barbed wire fence. Because I’m young and stupid, I get it in my head to jump over it while the wire’s slack,” Dean starts.

Sam and couple of the cowboys, Benny and Cas, are already smirking, chuckling a little, shaking their heads. They’ve definitely heard this one before, and this time, you have too. A smile curves your lips behind the rim of your glass of whiskey and Coke.

“I make it over, but my leg gets caught in the slack, and I just go down hard, eating the damn dirt,” Dean says. He mimes the impact of his body hitting the ground, complete with admittedly impressive sound effects. “But now the wire’s tight. Rips through my jeans, my ankle, blood soaking through. But, uh, Bobby calms me down, you know. He takes out his tool belt, and he says, ‘It’s all right, son. That’s why God made pliers, for idjits like you.’”

Laughter ripples across the table. Even John smiles, shaking his head.

“Well, he cleaned me up best he could and helped me back up on my horse,” Dean says. His grin is warm, and his gaze spans far beyond his beer. “Dad didn’t even have to lecture me. You remember what you said?”

John nods in amusement. “‘Your own body’s gonna do the punishing for me, son.’”

“Right. My ankle was busted for three weeks. Couldn’t ride, couldn’t do shit,” Dean says with a chuckle. “And it was summer too.”

At least he didn’t have to go to school, but for a boy like Dean, being cooped up in the house was three weeks of misery. All he could do was watch from his bedroom window while you and Sam ran off to ride your bikes in town or go swimming in the river.

He looks down toward the end of the table, wanting to see if you remember those days like he does. What he finds is your empty seat. His eyes run a search—and eventually catch you making your way over to the barn. His brows furrow in confusion, but as the conversation spins and Benny takes over the reminiscing, Dean gets up from the table, ignoring the little warning tug in his gut.

“Gonna get another beer,” he says.

But Sam’s perceptive gaze follows him. While you venture into the barn, Sam sees his brother’s projected path all too clearly.

The smell of horse makes you gag a little, but after you enter the barn and switch on the light, yet another wave of nostalgia blasts you in the face. You recognize that tack and tool shelf on the right-hand corner, and the rack of shotguns and rifles on the far left. You know these stalls, and you greet each of the horses like old friends, even though most of them are new ones.

You stop at one of the middle stalls on the right, clicking your tongue at an older horse. His coat is a deep coffee brown, dappled with white on his hindquarters.

“Dakota! Look at you, handsome.” You smile brightly. “Remember me?”

He blinks at you with those dark eyes, and he meanders a bit closer to the half door. You offer a loosely closed fist for him to inspect. When he does, you think it’s with some familiarity as he sniffs your hand all over. Or maybe he’s just smelling the apple pie glaze you licked off your finger earlier.

You laugh lightly and take a chance on petting the side of his neck. He lets you do it, a kind older statesman. Before you left, you had helped your dad break this horse in.

“He remembers you.”

You turn your head toward the door, flinching slightly in surprise. You didn’t even hear Dean come into the barn. His scuffed boots cross the distance leading him to you. Dark wash jeans and a black buttoned-down shirt are probably the extent of his cleaning up for the occasion, but the ensemble does suit him better than a proper suit would.

“It all looks the same,” you say quietly.

“That’s because it is,” Dean replies. His lips pull at a smirk as he points to the tool shed. “Like that dusty back room where we used to make out.”

You roll your eyes, but you can’t help the way your gaze draws to his calloused hands and long fingers. Your cheeks begin to prickle with warmth, but you refocus on his face, and unfortunately, that familiar grin. You’re sure that face has gotten him plenty of action since then.

“You do remember I have a fiancé,” you say.

Dean nods, holding up a placating hand. It slips into his pocket as he leans against a support beam. “Yeah, you never said where that guy was today.”

“Working,” you reply defensively. “We’re in the middle of a big project, and we can’t afford to drop the ball.”

“You two work together?”

“Yeah, for his father’s company.”

“Doing what?”

You hesitate. It seems like Sam hasn’t spoken to Dean yet about the offer either, but in this case, you’re grateful for it.

“Land development. His father is co-CEO and head of the Legal team. I help scope out properties and propose new projects,” you say.

Dean quirks a brow. “Land development, huh? Not what I would’ve imagined.”

His tone annoys you, making you slightly more tense, but you’ve already had this argument with Sam. You don’t have to explain yourself to this man.

“It’s not what I thought I’d end up in either, but if you think it’s hard to be a rancher, try being able to pay rent in California. We’re all just trying to survive, Dean,” you say.

At that, he actually nods more sincerely.

“Guess that’s fair. But it looks like you’re more than surviving now. You’ve got a friggin’ golf ball on your finger,” he says, gesturing at you, and more specifically your engagement ring.

You roll your eyes. “It’s not that big.”

The way he snorts earns a reluctant smile from you.

“How long you known the guy?” Dean asks.

You give him a shrewd look. He’s very curious about your personal life, but you can’t deny that you’ve been wondering what the past 12 years have made of him.

“About eight months,” you reply.

His brows raise almost as high as his hairline. “Eight months? When did he pop the question?”

“…A few weeks ago,” you say, albeit with some hesitation. “What?”

Dean shakes his head. “Nothing, I guess. Whirlwind romance.”

“And what about you?” you counter, fighting a blush. “No girlfriend?”

Dean chuckles. “Oh, I have plenty of friends. Just no time for the whirlwind.”

“I’m sure,” you say wryly. “Things really don’t change much around here.”

It’s a touch snider than you mean it to be. You don’t actually want to pick another fight. Frankly, you don’t have the emotional energy.

But even though Dean gives you a certain look, to your surprise, he doesn’t want to snipe anymore either. He just sighs.

“All right, come on. There’s some of Bobby’s stuff that you might want to look through,” he says, ushering you to follow him.

You do so reluctantly, over to the Foreman’s cabin.

The Foreman wrangles the other ranch hands, and he’s the Ranch Manager’s second-in-command. Bobby held that position for 23 years, starting from back when John was managing all operations himself. You used to live in this cabin with your mom and dad, back when they were together. 

Dean would later take your virginity when you turned 18—in the glorified closet that used to be your bedroom.

At least he doesn’t bring up that little anecdote as he leads you to the small, four-seater dining table. It has a few boxes stacked on top of it, probably what’s left of your father’s belongings. The rest has been cleared out except for a couch, an old wood coffee table, a TV on a stand, and some supplies in the kitchen. There are some signs of life here though, like a half-drunk beer on the coffee table, an empty box of pizza on the kitchen counter, and some crumpled napkins. Dean notices your observing gaze.

“I’ve been hanging out here the past few days. Cleaning the place up took a while, but uh, sometimes it’s nice to get away from the main house,” he says.

“I could see why. Thirty-two and still living with your daddy,” you teasingly remark.

Dean shoots you an amused brow raise, but he brings the first box to the living room coffee table and slides it toward you.

“Take whatever you want. He doesn’t have any other family, so I’m not sure what to do with the rest,” he says, rubbing a hand at the back of his neck.

Throwing it away feels wrong, or so his tone says. You nod in agreement and start looking through the box. The first thing you find is a large bottle of gold label scotch.

“Wow,” you say.

“That’s on brand,” Dean says, with a smirk. He eyes you. “We should probably crack it open, in Bobby’s honor, of course.”

Your lips tug at a smile. You hand it over, and Dean twists off the cap to take a swig. He offers it back to you, and you accept it dubiously after sitting beside him on the couch.

“You know we’re not teenagers anymore, right?” you say, but you still sip straight from the bottle just like he did, grimacing at the burn down your throat.

“We gotta lubricate this trip down memory lane somehow,” he replies. 

You snort in response and dig back into the box for something else.

Dean’s phone buzzes in his pocket. He checks and sees a text from Sam, asking if he’s with you.

Yeah, we’re going through Bobby’s stuff. I can come help. No need. It’s not that much. …Dude. What’re you doing? What? We’re good. Just catching up. All of a sudden you two are civil? I guess. It’s no big deal. We’ll be back in a few minutes. Ok. Just…be smart about this.

Dean frowns, resenting what his brother is insinuating. He glances up at you.

You haven’t noticed his silent conflict. You’re just looking through old baseball cards and faded trucker hats, rusty tools and piles of weathered flannel.

By the time you get to the third box, over an hour has passed, the bottle of scotch is almost empty, and you’re laughing harder and freer at the stories about Bobby that Dean’s pulling out easier than the next object. You haven’t even noticed that his knee rests against your thigh, or that you occasionally grab his forearm when something he says makes you particularly giggly.

It’s kind of cute that you still do that, but he keeps that thought locked in deep. His smile starts to hurt the corners of his cheeks, though.

Eventually, what you find at the bottom of the last box hits you so hard behind the ribs that it steals your breath. It’s a picture of you and your mom when you were around seven years old: your first year in this cabin, on this ranch.

To you it had seemed like a fun adventure, and so much cooler than your little boring apartment in Salida. Here, there were horses and cows and Sunday barbecues hosted by John Winchester himself.

It was on one of those Sundays that you met Dean, with all those freckles dotted across the bridge of his nose and cheeks, and the purest kind of happiness in his green eyes while he ate a slice of peach cobbler with a scoop of melting homemade ice cream. You remember him setting his own plate aside for a while though, just to comfort his six-year-old brother when his ice cream rolled off the side of his bowl into the dirt. Dean ended up slotting his own ice cream into Sammy’s bowl.

Bobby clocked what happened out of the corner of his eye. In the end, he was the one to slip you and Dean an extra scoop.

Your dad didn’t miss much, at least back then.

“I don’t get it, you know,” you say, somewhat shakily. “When we were kids, Dad was my safe place. Sure, he was gruff and curmudgeonly sometimes, but he was gentle too. He always looked out for me. I understand that shit didn’t work out between him and Mom, but I did try calling him. Years of five-minute conversations that never went anywhere, because he had to get back to the ranch.”

Your lips tremble and you try to blink past the sting, but the dam is already full to bursting, and your walls are failing all over again.

Dean watches you, and he actually listens as his heart grows heavier.

“I was a student. For a long time, I couldn’t afford to fly back to Salida,” you admit. “But he never once came out to visit. He didn’t even go to my college graduation. He showed up to Mom’s funeral. That’s it. I had to call the cemetery, the church, arrange the burial. I had to figure it all out by myself. And I get it, she left him. But he didn’t have to leave me too.”

You press your fingers over your mouth, as if that can stop the hurt from spilling out. You find sympathy in Dean’s eyes, but he doesn’t do what you expect. He rifles through the same collection of memories and pulls out a thin, white box.

Inside is a thin silver chain necklace with a small rose pendant. He lets the chain fall into your hand.

“He was going to give you this at your graduation,” Dean says. “I only know because he was hella fucking drunk one night, and he told me.” 

You laugh a little through unshed tears. You marvel at the necklace; it’s simple, dainty even, but beautiful. 

“Your mom told him not to go,” Dean says, earning your soft shock. “He hadn’t helped you pay for college, so in her mind, he didn’t have a right to see you. At least, that’s what he said happened.” 

“What?” you frown, rubbing the small pendant between your fingers. “I…can’t believe she said that.”

You had a partial scholarship and a work study job, but you wouldn’t have gotten through college without your mom. Living in San Diego hadn’t been easy at first, financially, and your mother was a nurse. You still don’t know how she managed it, but she always came through for you when it was time to pay for the next semester, and even for your textbooks.

You understood that even a Foreman didn’t make a hefty salary. It was part of the reason your mom gave you for leaving your dad. She didn’t come from a ranching family, and she had never wanted to spend her life on a ranch either, let alone one that your parents didn’t own.

In her words, “It’s hard to build a life on someone else’s land.”

She told you that she wanted more for you, and more for herself. Bobby hadn’t been willing to leave Winchester Ranch.

“He was dedicated to it. In some ways it was admirable, but in others…” she’d said, with an edge of bitterness.

You never really understood it. You realize now that you hadn’t tried hard enough. 

“I didn’t care about the fucking money or who paid for what. I just wanted him to be there,” you quietly confess. “But I know that’s a two-way street. I wasn’t there for him either.”

You look up at Dean, meeting his gaze.

“You were right,” you say, as emotion begins to choke you. “He had a goddamn heart attack, and I would’ve never known.”

Your shoulders shake as the first sob wracks through your body, but you soon find warmth and a familiar comfort in Dean’s arms.

“Okay, sweetheart. Come ‘ere,” he says, as he holds you close. There’s something different in his voice. Deep and a little coarse, but gentler. It’s the anchor you need right now, and you cling to it. You cling to him.

“It’s not your fault, okay? Seems like Bobby made his choices too,” Dean says. 

He tucks your head under his chin and briefly closes his eyes as he strokes your back. He feels every hiccup and unsteady breath in you, feels your tears dampening his shirt. His lips press to the crown of your head. Your fingers tangle in the green flannel at his back.

As you begin to relax after crying yourself out, your curled fingers smooth out into warm hands that release his shirt, but ultimately don’t move far, laid flat against his chest. He brushes frizzy strands of hair away from your face and behind your ear. You slowly look up to meet his eyes, with tears clinging to your lashes. Your lipstick is smudged, but you’re still a wonder to him.

It may just be the booze, but he remembers exactly how this used to feel. It cracks open something he’s been paving over, brick by brick. Year after year. He didn’t think this was what it would take to see you again.  

“Jesus,” he murmurs, brushing your cheek with his thumb. “You’re still so fucking beautiful. More, even.”

Your mouth parts with a hint of surprise, and a telling intake of breath. Your lashes lower as your gaze falls—to his lips.

What the hell is this?

You pull away from him, gently guiding his hand down.

He feels the sting of rejection, but also, his shame.

“’M sorry,” he says, looking away.

“…Yeah,” you say eloquently. You feel a prickle of guilt yourself as you wipe your cheeks.

You push yourself off the couch, but your body doesn’t cooperate well. Hard liquor hasn’t been your poison for a hot minute, whiskey least of all. Clearly, it’s remained a favorite of Dean’s.

But he’s far more than a memory you can shove to the back of your mind, especially when he gets up with you—to hold you and stop you from falling. He looks into your eyes, and the conflict in his makes you morbidly curious. What you would give to know what he’s thinking. 

“Just tell me one thing,” he says. “Does he treat you right?”

You frown. “Excuse me?”

His brows raise in challenge. “Come on. Work is work, but how’s he not gonna at least show up here for you?”

It probably makes him some kind of hypocrite, and he fights the voice inside that tells him he’s an idiot. An asshole.

But all you give him is the soft bite of your words.

“Not that it’s any of your business, but like I told you, our jobs are demanding,” you reply, crossing your arms. “He can be very considerate.”

Dean quirks a wry smile. He glances down at that ring, oval-shaped and vintage, putting it mildly. It would look real nice on his Great Aunt Matilda.

“Yeah, with this, huh?” he says, grasping your left hand. “Tell me this is some kind of kooky family heirloom.”

You slip your hand out of his. “He found it at an estate sale.”

“Oh, I believe you,” Dean chuckles. He taps the humble pendant that now has a place above your heart, after he helped you figure out how to put on the necklace it belongs to. “That’s more your speed.”

“How would you know?” you retort, batting his finger off. “It’s been all this time, and you think you still know me?”

You really do walk away from him now, beelining toward the door…

Well, you would have. You will. But his audacity truly is monumental, and after how he treated you this morning, this really is too much for you to wrap your head around. It derails what would’ve been a highly justified storm-out, and compels you back to face him in frustration.

“What’re you trying to do, Dean, spin my head around?” you snap. “You’re the one who broke my heart first. You don’t even know how much you messed me up.”

The confession escapes you before you can cram it back in, shocking you as well as him.

But it’s true.

Years. It had taken you years to get over him, your best friend. Your first real love.

Dean’s amusement faded the more you spoke.

“I know,” he says. And the admission costs him. Under the layers of bravado, bitterness and hurt, there’s the truth. “I was a stupid kid back then, who didn’t know how to let you go.”

You shake your head in denial. Your heart hurts, probably because it never healed right the first time.

“That’s bullshit,” you say. “You didn’t have to let me go. That was your choice.”

“Yeah, I did,” Dean says, with a newfound certainty that dims the light from his eyes. “You had a life ahead of you, sweetheart. Mine was always gonna be on this ranch.”

For a moment, you’re stunned where you stand.

Until reason and doubt start to compete for new ground in your mind.

He’s still making excuses, you think. He could’ve come with you to college. You told him that then, and even if his father tried to nail his boots to the ground, Dean never even called you once after you left. Where was this apology when it would’ve mattered?

“Jesus Christ, Dean…”

You rub your forehead at the headache you already feel coming on. You’re probably drunk, in fairness.

“Why are you telling me all this now?” you ask.

He sighs and rakes a hand through his hair, then rubs his eyes as well.

“Good question,” he chuckles slightly. He sobers when he meets your eyes again. “You told the truth today at the funeral. It’s only fair I give you the same courtesy.”

“Courtesy. Is that what this is?” you challenge.

“It’s an apology,” he says. “And uh, it’s goodbye, stranger, I guess.”

“Goodbye,” you echo. Though you’re unable to stop yourself from glancing down at his lips again. Then back to his eyes, despite the glassiness in yours. A hitch in your breath. “I guess it is.”

Dean sees it, another spark of your tears. He still hates it, both selfishly and unselfishly.

He can’t help but try to give you the stability you need. First, by his slow attempt to hold you, brushing his thumbs against your arms. Your mouth parts, but you don’t pull away.

He bows his head and follows the deep-seated need in his gut, urging him to press his lips to yours.

You breathe in sharply through your nose, but your fingers clench in his shirt again, near his collar. Your body melts willingly against his, like a muscle memory you thought you lost.

Then, the brush of his tongue short-circuits your brain. His hand moves down to the small of your back and presses you into him, eliciting tingles down your spine, and a blooming, pulsing heat between your legs.

You whimper into his mouth, and his hold tightens a fraction.

You pull back for a moment, panting for air. Your eyes meet his incredulously.

He steels himself, waiting for a slap, or at least a push.

You don’t have it in yourself to give him either one. Your heart clenches painfully, because despite the guilt and shame you already feel, something inside you, deeply vulnerable and frayed, needs this.

You tell yourself it’s just one more kiss.

He meets you halfway when you lean up to claim his lips. He claims you back, his hands once again molding to your waist, his arms caging you in, his hand sinking into your hair.

One more turns into him backing you up against the wall. You grab onto his shoulders for leverage, then his hair as his lips veer away from yours to blaze a hot, wet trail down your neck. Your moan is perfect in his ear, rattling down his spine and right to his cock.

You feel him heavy and thick through his jeans, pressing against you. His hand slips up your thigh, squeezing plush flesh as he goes. He bunches the skirt of your dress up to your hips.

“Unzip me,” you tell him, through hushed tones and heated breaths.

Dean nods, turning you around and brushing your hair out of the way so he can drag the zipper down in a slow, torturous tease. His eyes drink in every inch of your skin, but there’s nothing sexier to him than the way you brush down the sleeves and slip out of the dress the rest of the way. The fabric falls around your ankles, and you step out of them in your tall heels. Dean gets the full view of your lace panties, then the matching bra when you turn back around.

He catches your little intake of breath, like you’re guarding yourself before he sees you. He smiles and pulls you back in by your waist.

“Like I said, fucking beautiful,” he says, his gaze roaming your face.

Your lips tug at a smile as you meet his stare, but he finally renders you without a snappy word to say. He takes that win and revels in it as he kisses you.

You touch him more confidently than he remembers, dragging your nails down the back of his neck, sucking his tongue into your mouth, down to grabbing onto his belt and popping the buckle open. He follows your lead and helps you loosen his belt and jeans, but his boots and your heels are the first to form a haphazard pile on the way into the bigger bedroom, where his spare sheets and an old comforter line the bed.

He wasn’t lying to you when he said he’s been staying over here for the past few days. Not only so that he could clean up, but because he needed to clear his own head. Bobby’s death shook everyone, but it hit Dean in a way he hadn’t expected. He hasn’t told anyone this, but it was like losing a second father.

It reminded Dean of his regrets—his biggest one of all being you.

Despite how it looks, he knows it’s wrong to touch you. He knows it’s selfish to want you. But he hasn’t allowed himself to want anything in such a long time, and he thinks he might be able to right some old wrongs while he’s busy committing new ones.

After he lays you on the bed underneath him, Dean kisses his way along the column of your throat, down between your breasts. He slips a hand underneath you to unhook the pretty lace bra, and your back arches, giving him room. 

You really have grown up beautifully, even your boobs. Good for you, and good for him. Dean recommits them to memory as his tongue lavishes one of your nipples, while his right hand rolls the other between his thumb and forefinger. You sigh his name and slip your fingers through his hair, scratching his scalp with your nails. But your fingers hook on his flannel next.

“Take this off,” you breathe. “Want to see you too.”

Dean hesitates, but concedes to taking off his outer flannel. His undershirt stays on, even though you tug on it next. He aims to distract you by moving further down your body, laying open-mouthed kisses down your ribs and stomach, and over your mound, after he slips off your panties. He glances up between your legs and shoots you a mischievous grin.

“I used to love the way you tasted,” he says. “Those little sounds you made, the way you’d buck against my chin and scream my name… Let’s see if we can rock another sequel, huh, sweetheart?” 

“Dean,” you gasp, as his fingers slip between the folds of your pussy. They find slick arousal and heat.

“Jesus,” he murmurs. “You’re soaking wet.”

He bites his lower lip as his thumb searches, then finds your clit. Your hips start to writhe as you moan, grinding against his hand. He smirks in satisfaction before he lowers down. He moves your left thigh over his shoulder, and he feasts.

Your mouth falls open in a near silent cry, and your hips nearly come off the bed as you feel his tongue replace his fingers on your clit. Those long digits slip inside your hot channel. Hunger pools in your lower belly as your inner walls clench on him, desperately needing friction. Your breaths deepen as your free hand goes to your breast, toying with a hard nipple while you savor the sensations Dean’s giving you with his mouth and skilled fingers.

He curls his fingers and strokes you deeply, searching, exploring, until he finds that most sensitive place within your inner walls that has your body shuddering like an accordion. You grab a fistful of his hair as you buck hard against his mouth, a choked scream falling from your lips.

After withdrawing his fingers and wiping his mouth and nose, he presses a kiss into your inner thigh as you still tremble with the aftershocks of your orgasm.

He moves back up your body, and you take his face in your hands to kiss him deeply.

“What’s the verdict?” he teases afterward.

“You’ve gotten better,” you admit.

You sit up, intending to return the favor as your hands roam down his chest and underneath his shirt. He feels toned from long hours of hard labor and horse riding, but he stills your hands from grasping at the edge of his shirt. You’re confused, but he quickly guides you into turning over in the bed.

He kneels behind you as his steady hands continue to map every inch of your body. He caresses your sides, across your middle, and back up to your breasts while he kisses along your neck, then down your shoulder. There’s more calm confidence in his touch than he had at 20 years old, certainly more strength and more callouses, but it’s a delicious friction. And it’s a feeling that he absolutely has you enveloped in his arms, within his broad frame. You hang onto him on reflex.

Two of his fingers dip back into your pussy, circling your clit. You hang onto his arm as your body gives way to a moan. Arousal begins to pulse deep inside you again, but this time, you need his cock. You want to know if he’s improved there too. He seems to remember your body well enough.

“Dean…just fuck me,” you whisper coarsely. “Please…”

Before I lose my nerve.

“I gotcha, sweetheart,” he says, in a voice like old scotch and honey. Its depths make prickles of heat flash across your skin as fabric rustles. You assume he’s finally stripping off the rest of his clothes. You catch a glimpse over your shoulder of him tossing his shirt and boxers to the floor, but soon, the heat of his presence returns as he lines himself up at your entrance. His cock finally pushing inside you from behind makes your thighs tremble. Your nails dig into the mattress sheets.

“Dean,” you gasp. He stretches you so fucking good.

“You’ve got it, baby. Every damn inch, doing so good,” he says, breathing hard into your neck. His teeth graze your shoulder, making you shudder and push into him on reflex, sheathing him nice and snug inside. Already the walls of your cunt tremble around his cock.

Dean keeps his promise; it’s dewy skin against skin as holds you to him while he fucks you, slow, deep, and powerful, but never painful. Never too much.

He asks you what you want—faster or slower, rougher, or easier rhythm. You tell him you want him exactly how he is: fucking perfect.

And that night, it is fucking perfect.

Almost.

Both of you have left your cell phones on the kitchen table. They’ve buzzed almost half a dozen times, each with text messages and a handful of calls.

Your little black dress collects dust on the floor along with his jeans and flannel.

In the morning, long after he should, Dean wakes up nice and easy.

He just ends up waking alone.

AN: 🫣 Sorry loll. If you think those twists were fun, then get ready for a whole messy love triangle when Brady re-enters from Stage Left. 😬 (And are you curious about Dean and reader's past?)

Next Time:

What have I done?

Okay, you were drunk, but not that drunk.

You were in pain. Reckless. Selfish.

Shame invades your body and settles into your heart. All you can do is slowly, silently slip out of the bed without disturbing Dean. After reclaiming your clothes from the dusty floor and getting dressed, you hold back tears as you try to leave the tangle of desire and old memories, both beautiful and painful, behind you in that room. All you take with you is your phone and the silver necklace you already wear.

Although you wait to put on your heels until you get outside the cabin, that big stretch of hill up ahead to the main house is daunting.

“Mornin’.”

Your head turns sharply at the voice. You shouldn’t be surprised that someone’s already up this early, let alone one of the ranch hands. Benny. He’s tall and broad, like Dean, though with reddish brown hair and a thicker beard. He’s already dressed for the day in jeans and a long-sleeved shirt, drinking his coffee as he leans against the bunkhouse wall. You nod back at him with an awkward smile. 

“How you plan to get up the hill in those pumps?” he asks.

You sigh. “I don’t.”

You’re about to execute the worst walk of shame you’ve ever done, but at least it’s only for an audience of one. You slip off the heels and let the ankle straps dangle from your fingers as you walk barefoot on wet, dewy earth, all the way back up to the house. 

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John's famous barbecue pit spins the mouthwatering smells of smoked meats. The tables are lined up and filled with buttery cornbread, potatoes done three different ways (mashed, roasted, and casseroled), salads, slaw, carrots and corn, wild rice, homemade dinner rolls and garlic bread, and no less than five different flavors of pie. You spy Dean tucking into his third slice of cherry. Evidently, it’s still his favorite. A piece of pastry crust flecks from his lower lip as he jumps in with an old story.

“So I’m maybe…twelve, thirteen. Bobby’s trying to show me how to fix this patch of barbed wire fence. Because I’m young and stupid, I get it in my head to jump over it while the wire’s slack,” Dean starts.

Sam and couple of the cowboys, Benny and Cas, are already smirking, chuckling a little, shaking their heads. They’ve definitely heard this one before, and this time, you have too. A smile curves your lips behind the rim of your glass of whiskey and Coke.

“I make it over, but my leg gets caught in the slack, and I just go down hard, eating the damn dirt,” Dean says. He mimes the impact of his body hitting the ground, complete with admittedly impressive sound effects. “But now the wire’s tight. Rips through my jeans, my ankle, blood soaking through. But, uh, Bobby calms me down, you know. He takes out his tool belt, and he says, ‘It’s all right, son. That’s why God made pliers, for idjits like you.’”

Laughter ripples across the table. Even John smiles, shaking his head.

“Well, he cleaned me up best he could and helped me back up on my horse,” Dean says. His grin is warm, and his gaze spans far beyond his beer. “Dad didn’t even have to lecture me. You remember what you said?”

John nods in amusement. “‘Your own body’s gonna do the punishing for me, son.’”

“Right. My ankle was busted for three weeks. Couldn’t ride, couldn’t do shit,” Dean says with a chuckle. “And it was summer too.”

At least he didn’t have to go to school, but for a boy like Dean, being cooped up in the house was three weeks of misery. All he could do was watch from his bedroom window while you and Sam ran off to ride your bikes in town or go swimming in the river.

He looks down toward the end of the table, wanting to see if you remember those days like he does. What he finds is your empty seat. His eyes run a search—and eventually catch you making your way over to the barn. His brows furrow in confusion, but as the conversation spins and Benny takes over the reminiscing, Dean gets up from the table, ignoring the little warning tug in his gut.

“Gonna get another beer,” he says.

But Sam’s perceptive gaze follows him. While you venture into the barn, Sam sees his brother’s projected path all too clearly.

The smell of horse makes you gag a little, but after you enter the barn and switch on the light, yet another wave of nostalgia blasts you in the face. You recognize that tack and tool shelf on the right-hand corner, and the rack of shotguns and rifles on the far left. You know these stalls, and you greet each of the horses like old friends, even though most of them are new ones.

You stop at one of the middle stalls on the right, clicking your tongue at an older horse. His coat is a deep coffee brown, dappled with white on his hindquarters.

“Dakota! Look at you, handsome.” You smile brightly. “Remember me?”

He blinks at you with those dark eyes, and he meanders a bit closer to the half door. You offer a loosely closed fist for him to inspect. When he does, you think it’s with some familiarity as he sniffs your hand all over. Or maybe he’s just smelling the apple pie glaze you licked off your finger earlier.

You laugh lightly and take a chance on petting the side of his neck. He lets you do it, a kind older statesman. Before you left, you had helped your dad break this horse in.

“He remembers you.”

You turn your head toward the door, flinching slightly in surprise. You didn’t even hear Dean come into the barn. His scuffed boots cross the distance leading him to you. Dark wash jeans and a black buttoned-down shirt are probably the extent of his cleaning up for the occasion, but the ensemble does suit him better than a proper suit would.

“It all looks the same,” you say quietly.

“That’s because it is,” Dean replies. His lips pull at a smirk as he points to the tool shed. “Like that dusty back room where we used to make out.”

You roll your eyes, but you can’t help the way your gaze draws to his calloused hands and long fingers. Your cheeks begin to prickle with warmth, but you refocus on his face, and unfortunately, that familiar grin. You’re sure that face has gotten him plenty of action since then.

“You do remember I have a fiancé,” you say.

Dean nods, holding up a placating hand. It slips into his pocket as he leans against a support beam. “Yeah, you never said where that guy was today.”

“Working,” you reply defensively. “We’re in the middle of a big project, and we can’t afford to drop the ball.”

“You two work together?”

“Yeah, for his father’s company.”

“Doing what?”

You hesitate. It seems like Sam hasn’t spoken to Dean yet about the offer either, but in this case, you’re grateful for it.

“Land development. His father is co-CEO and head of the Legal team. I help scope out properties and propose new projects,” you say.

Dean quirks a brow. “Land development, huh? Not what I would’ve imagined.”

His tone annoys you, making you slightly more tense, but you’ve already had this argument with Sam. You don’t have to explain yourself to this man.

“It’s not what I thought I’d end up in either, but if you think it’s hard to be a rancher, try being able to pay rent in California. We’re all just trying to survive, Dean,” you say.

At that, he actually nods more sincerely.

“Guess that’s fair. But it looks like you’re more than surviving now. You’ve got a friggin’ golf ball on your finger,” he says, gesturing at you, and more specifically your engagement ring.

You roll your eyes. “It’s not that big.”

The way he snorts earns a reluctant smile from you.

“How long you known the guy?” Dean asks.

You give him a shrewd look. He’s very curious about your personal life, but you can’t deny that you’ve been wondering what the past 12 years have made of him.

“About eight months,” you reply.

His brows raise almost as high as his hairline. “Eight months? When did he pop the question?”

“…A few weeks ago,” you say, albeit with some hesitation. “What?”

Dean shakes his head. “Nothing, I guess. Whirlwind romance.”

“And what about you?” you counter, fighting a blush. “No girlfriend?”

Dean chuckles. “Oh, I have plenty of friends. Just no time for the whirlwind.”

“I’m sure,” you say wryly. “Things really don’t change much around here.”

It’s a touch snider than you mean it to be. You don’t actually want to pick another fight. Frankly, you don’t have the emotional energy.

But even though Dean gives you a certain look, to your surprise, he doesn’t want to snipe anymore either. He just sighs.

“All right, come on. There’s some of Bobby’s stuff that you might want to look through,” he says, ushering you to follow him.

You do so reluctantly, over to the Foreman’s cabin.

The Foreman wrangles the other ranch hands, and he’s the Ranch Manager’s second-in-command. Bobby held that position for 23 years, starting from back when John was managing all operations himself. You used to live in this cabin with your mom and dad, back when they were together. 

Dean would later take your virginity when you turned 18—in the glorified closet that used to be your bedroom.

At least he doesn’t bring up that little anecdote as he leads you to the small, four-seater dining table. It has a few boxes stacked on top of it, probably what’s left of your father’s belongings. The rest has been cleared out except for a couch, an old wood coffee table, a TV on a stand, and some supplies in the kitchen. There are some signs of life here though, like a half-drunk beer on the coffee table, an empty box of pizza on the kitchen counter, and some crumpled napkins. Dean notices your observing gaze.

“I’ve been hanging out here the past few days. Cleaning the place up took a while, but uh, sometimes it’s nice to get away from the main house,” he says.

“I could see why. Thirty-two and still living with your daddy,” you teasingly remark.

Dean shoots you an amused brow raise, but he brings the first box to the living room coffee table and slides it toward you.

“Take whatever you want. He doesn’t have any other family, so I’m not sure what to do with the rest,” he says, rubbing a hand at the back of his neck.

Throwing it away feels wrong, or so his tone says. You nod in agreement and start looking through the box. The first thing you find is a large bottle of gold label scotch.

“Wow,” you say.

“That’s on brand,” Dean says, with a smirk. He eyes you. “We should probably crack it open, in Bobby’s honor, of course.”

Your lips tug at a smile. You hand it over, and Dean twists off the cap to take a swig. He offers it back to you, and you accept it dubiously after sitting beside him on the couch.

“You know we’re not teenagers anymore, right?” you say, but you still sip straight from the bottle just like he did, grimacing at the burn down your throat.

“We gotta lubricate this trip down memory lane somehow,” he replies. 

You snort in response and dig back into the box for something else.

Dean’s phone buzzes in his pocket. He checks and sees a text from Sam, asking if he’s with you.

Yeah, we’re going through Bobby’s stuff. I can come help. No need. It’s not that much. …Dude. What’re you doing? What? We’re good. Just catching up. All of a sudden you two are civil? I guess. It’s no big deal. We’ll be back in a few minutes. Ok. Just…be smart about this.

Dean frowns, resenting what his brother is insinuating. He glances up at you.

You haven’t noticed his silent conflict. You’re just looking through old baseball cards and faded trucker hats, rusty tools and piles of weathered flannel.

By the time you get to the third box, over an hour has passed, the bottle of scotch is almost empty, and you’re laughing harder and freer at the stories about Bobby that Dean’s pulling out easier than the next object. You haven’t even noticed that his knee rests against your thigh, or that you occasionally grab his forearm when something he says makes you particularly giggly.

It’s kind of cute that you still do that, but he keeps that thought locked in deep. His smile starts to hurt the corners of his cheeks, though.

Eventually, what you find at the bottom of the last box hits you so hard behind the ribs that it steals your breath. It’s a picture of you and your mom when you were around seven years old: your first year in this cabin, on this ranch.

To you it had seemed like a fun adventure, and so much cooler than your little boring apartment in Salida. Here, there were horses and cows and Sunday barbecues hosted by John Winchester himself.

It was on one of those Sundays that you met Dean, with all those freckles dotted across the bridge of his nose and cheeks, and the purest kind of happiness in his green eyes while he ate a slice of peach cobbler with a scoop of melting homemade ice cream. You remember him setting his own plate aside for a while though, just to comfort his six-year-old brother when his ice cream rolled off the side of his bowl into the dirt. Dean ended up slotting his own ice cream into Sammy’s bowl.

Bobby clocked what happened out of the corner of his eye. In the end, he was the one to slip you and Dean an extra scoop.

Your dad didn’t miss much, at least back then.

“I don’t get it, you know,” you say, somewhat shakily. “When we were kids, Dad was my safe place. Sure, he was gruff and curmudgeonly sometimes, but he was gentle too. He always looked out for me. I understand that shit didn’t work out between him and Mom, but I did try calling him. Years of five-minute conversations that never went anywhere, because he had to get back to the ranch.”

Your lips tremble and you try to blink past the sting, but the dam is already full to bursting, and your walls are failing all over again.

Dean watches you, and he actually listens as his heart grows heavier.

“I was a student. For a long time, I couldn’t afford to fly back to Salida,” you admit. “But he never once came out to visit. He didn’t even go to my college graduation. He showed up to Mom’s funeral. That’s it. I had to call the cemetery, the church, arrange the burial. I had to figure it all out by myself. And I get it, she left him. But he didn’t have to leave me too.”

You press your fingers over your mouth, as if that can stop the hurt from spilling out. You find sympathy in Dean’s eyes, but he doesn’t do what you expect. He rifles through the same collection of memories and pulls out a thin, white box.

Inside is a thin silver chain necklace with a small rose pendant. He lets the chain fall into your hand.

“He was going to give you this at your graduation,” Dean says. “I only know because he was hella fucking drunk one night, and he told me.” 

You laugh a little through unshed tears. You marvel at the necklace; it’s simple, dainty even, but beautiful. 

“Your mom told him not to go,” Dean says, earning your soft shock. “He hadn’t helped you pay for college, so in her mind, he didn’t have a right to see you. At least, that’s what he said happened.” 

“What?” you frown, rubbing the small pendant between your fingers. “I…can’t believe she said that.”

You had a partial scholarship and a work study job, but you wouldn’t have gotten through college without your mom. Living in San Diego hadn’t been easy at first, financially, and your mother was a nurse. You still don’t know how she managed it, but she always came through for you when it was time to pay for the next semester, and even for your textbooks.

You understood that even a Foreman didn’t make a hefty salary. It was part of the reason your mom gave you for leaving your dad. She didn’t come from a ranching family, and she had never wanted to spend her life on a ranch either, let alone one that your parents didn’t own.

In her words, “It’s hard to build a life on someone else’s land.”

She told you that she wanted more for you, and more for herself. Bobby hadn’t been willing to leave Winchester Ranch.

“He was dedicated to it. In some ways it was admirable, but in others…” she’d said, with an edge of bitterness.

You never really understood it. You realize now that you hadn’t tried hard enough. 

“I didn’t care about the fucking money or who paid for what. I just wanted him to be there,” you quietly confess. “But I know that’s a two-way street. I wasn’t there for him either.”

You look up at Dean, meeting his gaze.

“You were right,” you say, as emotion begins to choke you. “He had a goddamn heart attack, and I would’ve never known.”

Your shoulders shake as the first sob wracks through your body, but you soon find warmth and a familiar comfort in Dean’s arms.

“Okay, sweetheart. Come ‘ere,” he says, as he holds you close. There’s something different in his voice. Deep and a little coarse, but gentler. It’s the anchor you need right now, and you cling to it. You cling to him.

“It’s not your fault, okay? Seems like Bobby made his choices too,” Dean says. 

He tucks your head under his chin and briefly closes his eyes as he strokes your back. He feels every hiccup and unsteady breath in you, feels your tears dampening his shirt. His lips press to the crown of your head. Your fingers tangle in the green flannel at his back.

As you begin to relax after crying yourself out, your curled fingers smooth out into warm hands that release his shirt, but ultimately don’t move far, laid flat against his chest. He brushes frizzy strands of hair away from your face and behind your ear. You slowly look up to meet his eyes, with tears clinging to your lashes. Your lipstick is smudged, but you’re still a wonder to him.

It may just be the booze, but he remembers exactly how this used to feel. It cracks open something he’s been paving over, brick by brick. Year after year. He didn’t think this was what it would take to see you again.  

“Jesus,” he murmurs, brushing your cheek with his thumb. “You’re still so fucking beautiful. More, even.”

Your mouth parts with a hint of surprise, and a telling intake of breath. Your lashes lower as your gaze falls—to his lips.

What the hell is this?

You pull away from him, gently guiding his hand down.

He feels the sting of rejection, but also, his shame.

“’M sorry,” he says, looking away.

“…Yeah,” you say eloquently. You feel a prickle of guilt yourself as you wipe your cheeks.

You push yourself off the couch, but your body doesn’t cooperate well. Hard liquor hasn’t been your poison for a hot minute, whiskey least of all. Clearly, it’s remained a favorite of Dean’s.

But he’s far more than a memory you can shove to the back of your mind, especially when he gets up with you—to hold you and stop you from falling. He looks into your eyes, and the conflict in his makes you morbidly curious. What you would give to know what he’s thinking. 

“Just tell me one thing,” he says. “Does he treat you right?”

You frown. “Excuse me?”

His brows raise in challenge. “Come on. Work is work, but how’s he not gonna at least show up here for you?”

It probably makes him some kind of hypocrite, and he fights the voice inside that tells him he’s an idiot. An asshole.

But all you give him is the soft bite of your words.

“Not that it’s any of your business, but like I told you, our jobs are demanding,” you reply, crossing your arms. “He can be very considerate.”

Dean quirks a wry smile. He glances down at that ring, oval-shaped and vintage, putting it mildly. It would look real nice on his Great Aunt Matilda.

“Yeah, with this, huh?” he says, grasping your left hand. “Tell me this is some kind of kooky family heirloom.”

You slip your hand out of his. “He found it at an estate sale.”

“Oh, I believe you,” Dean chuckles. He taps the humble pendant that now has a place above your heart, after he helped you figure out how to put on the necklace it belongs to. “That’s more your speed.”

“How would you know?” you retort, batting his finger off. “It’s been all this time, and you think you still know me?”

You really do walk away from him now, beelining toward the door…

Well, you would have. You will. But his audacity truly is monumental, and after how he treated you this morning, this really is too much for you to wrap your head around. It derails what would’ve been a highly justified storm-out, and compels you back to face him in frustration.

“What’re you trying to do, Dean, spin my head around?” you snap. “You’re the one who broke my heart first. You don’t even know how much you messed me up.”

The confession escapes you before you can cram it back in, shocking you as well as him.

But it’s true.

Years. It had taken you years to get over him, your best friend. Your first real love.

Dean’s amusement faded the more you spoke.

“I know,” he says. And the admission costs him. Under the layers of bravado, bitterness and hurt, there’s the truth. “I was a stupid kid back then, who didn’t know how to let you go.”

You shake your head in denial. Your heart hurts, probably because it never healed right the first time.

“That’s bullshit,” you say. “You didn’t have to let me go. That was your choice.”

“Yeah, I did,” Dean says, with a newfound certainty that dims the light from his eyes. “You had a life ahead of you, sweetheart. Mine was always gonna be on this ranch.”

For a moment, you’re stunned where you stand.

Until reason and doubt start to compete for new ground in your mind.

He’s still making excuses, you think. He could’ve come with you to college. You told him that then, and even if his father tried to nail his boots to the ground, Dean never even called you once after you left. Where was this apology when it would’ve mattered?

“Jesus Christ, Dean…”

You rub your forehead at the headache you already feel coming on. You’re probably drunk, in fairness.

“Why are you telling me all this now?” you ask.

He sighs and rakes a hand through his hair, then rubs his eyes as well.

“Good question,” he chuckles slightly. He sobers when he meets your eyes again. “You told the truth today at the funeral. It’s only fair I give you the same courtesy.”

“Courtesy. Is that what this is?” you challenge.

“It’s an apology,” he says. “And uh, it’s goodbye, stranger, I guess.”

“Goodbye,” you echo. Though you’re unable to stop yourself from glancing down at his lips again. Then back to his eyes, despite the glassiness in yours. A hitch in your breath. “I guess it is.”

Dean sees it, another spark of your tears. He still hates it, both selfishly and unselfishly.

He can’t help but try to give you the stability you need. First, by his slow attempt to hold you, brushing his thumbs against your arms. Your mouth parts, but you don’t pull away.

He bows his head and follows the deep-seated need in his gut, urging him to press his lips to yours.

You breathe in sharply through your nose, but your fingers clench in his shirt again, near his collar. Your body melts willingly against his, like a muscle memory you thought you lost.

Then, the brush of his tongue short-circuits your brain. His hand moves down to the small of your back and presses you into him, eliciting tingles down your spine, and a blooming, pulsing heat between your legs.

You whimper into his mouth, and his hold tightens a fraction.

You pull back for a moment, panting for air. Your eyes meet his incredulously.

He steels himself, waiting for a slap, or at least a push.

You don’t have it in yourself to give him either one. Your heart clenches painfully, because despite the guilt and shame you already feel, something inside you, deeply vulnerable and frayed, needs this.

You tell yourself it’s just one more kiss.

He meets you halfway when you lean up to claim his lips. He claims you back, his hands once again molding to your waist, his arms caging you in, his hand sinking into your hair.

One more turns into him backing you up against the wall. You grab onto his shoulders for leverage, then his hair as his lips veer away from yours to blaze a hot, wet trail down your neck. Your moan is perfect in his ear, rattling down his spine and right to his cock.

You feel him heavy and thick through his jeans, pressing against you. His hand slips up your thigh, squeezing plush flesh as he goes. He bunches the skirt of your dress up to your hips.

“Unzip me,” you tell him, through hushed tones and heated breaths.

Dean nods, turning you around and brushing your hair out of the way so he can drag the zipper down in a slow, torturous tease. His eyes drink in every inch of your skin, but there’s nothing sexier to him than the way you brush down the sleeves and slip out of the dress the rest of the way. The fabric falls around your ankles, and you step out of them in your tall heels. Dean gets the full view of your lace panties, then the matching bra when you turn back around.

He catches your little intake of breath, like you’re guarding yourself before he sees you. He smiles and pulls you back in by your waist.

“Like I said, fucking beautiful,” he says, his gaze roaming your face.

Your lips tug at a smile as you meet his stare, but he finally renders you without a snappy word to say. He takes that win and revels in it as he kisses you.

You touch him more confidently than he remembers, dragging your nails down the back of his neck, sucking his tongue into your mouth, down to grabbing onto his belt and popping the buckle open. He follows your lead and helps you loosen his belt and jeans, but his boots and your heels are the first to form a haphazard pile on the way into the bigger bedroom, where his spare sheets and an old comforter line the bed.

He wasn’t lying to you when he said he’s been staying over here for the past few days. Not only so that he could clean up, but because he needed to clear his own head. Bobby’s death shook everyone, but it hit Dean in a way he hadn’t expected. He hasn’t told anyone this, but it was like losing a second father.

It reminded Dean of his regrets—his biggest one of all being you.

Despite how it looks, he knows it’s wrong to touch you. He knows it’s selfish to want you. But he hasn’t allowed himself to want anything in such a long time, and he thinks he might be able to right some old wrongs while he’s busy committing new ones.

After he lays you on the bed underneath him, Dean kisses his way along the column of your throat, down between your breasts. He slips a hand underneath you to unhook the pretty lace bra, and your back arches, giving him room. 

You really have grown up beautifully, even your boobs. Good for you, and good for him. Dean recommits them to memory as his tongue lavishes one of your nipples, while his right hand rolls the other between his thumb and forefinger. You sigh his name and slip your fingers through his hair, scratching his scalp with your nails. But your fingers hook on his flannel next.

“Take this off,” you breathe. “Want to see you too.”

Dean hesitates, but concedes to taking off his outer flannel. His undershirt stays on, even though you tug on it next. He aims to distract you by moving further down your body, laying open-mouthed kisses down your ribs and stomach, and over your mound, after he slips off your panties. He glances up between your legs and shoots you a mischievous grin.

“I used to love the way you tasted,” he says. “Those little sounds you made, the way you’d buck against my chin and scream my name… Let’s see if we can rock another sequel, huh, sweetheart?” 

“Dean,” you gasp, as his fingers slip between the folds of your pussy. They find slick arousal and heat.

“Jesus,” he murmurs. “You’re soaking wet.”

He bites his lower lip as his thumb searches, then finds your clit. Your hips start to writhe as you moan, grinding against his hand. He smirks in satisfaction before he lowers down. He moves your left thigh over his shoulder, and he feasts.

Your mouth falls open in a near silent cry, and your hips nearly come off the bed as you feel his tongue replace his fingers on your clit. Those long digits slip inside your hot channel. Hunger pools in your lower belly as your inner walls clench on him, desperately needing friction. Your breaths deepen as your free hand goes to your breast, toying with a hard nipple while you savor the sensations Dean’s giving you with his mouth and skilled fingers.

He curls his fingers and strokes you deeply, searching, exploring, until he finds that most sensitive place within your inner walls that has your body shuddering like an accordion. You grab a fistful of his hair as you buck hard against his mouth, a choked scream falling from your lips.

After withdrawing his fingers and wiping his mouth and nose, he presses a kiss into your inner thigh as you still tremble with the aftershocks of your orgasm.

He moves back up your body, and you take his face in your hands to kiss him deeply.

“What’s the verdict?” he teases afterward.

“You’ve gotten better,” you admit.

You sit up, intending to return the favor as your hands roam down his chest and underneath his shirt. He feels toned from long hours of hard labor and horse riding, but he stills your hands from grasping at the edge of his shirt. You’re confused, but he quickly guides you into turning over in the bed.

He kneels behind you as his steady hands continue to map every inch of your body. He caresses your sides, across your middle, and back up to your breasts while he kisses along your neck, then down your shoulder. There’s more calm confidence in his touch than he had at 20 years old, certainly more strength and more callouses, but it’s a delicious friction. And it’s a feeling that he absolutely has you enveloped in his arms, within his broad frame. You hang onto him on reflex.

Two of his fingers dip back into your pussy, circling your clit. You hang onto his arm as your body gives way to a moan. Arousal begins to pulse deep inside you again, but this time, you need his cock. You want to know if he’s improved there too. He seems to remember your body well enough.

“Dean…just fuck me,” you whisper coarsely. “Please…”

Before I lose my nerve.

“I gotcha, sweetheart,” he says, in a voice like old scotch and honey. Its depths make prickles of heat flash across your skin as fabric rustles. You assume he’s finally stripping off the rest of his clothes. You catch a glimpse over your shoulder of him tossing his shirt and boxers to the floor, but soon, the heat of his presence returns as he lines himself up at your entrance. His cock finally pushing inside you from behind makes your thighs tremble. Your nails dig into the mattress sheets.

“Dean,” you gasp. He stretches you so fucking good.

“You’ve got it, baby. Every damn inch, doing so good,” he says, breathing hard into your neck. His teeth graze your shoulder, making you shudder and push into him on reflex, sheathing him nice and snug inside. Already the walls of your cunt tremble around his cock.

Dean keeps his promise; it’s dewy skin against skin as holds you to him while he fucks you, slow, deep, and powerful, but never painful. Never too much.

He asks you what you want—faster or slower, rougher, or easier rhythm. You tell him you want him exactly how he is: fucking perfect.

And that night, it is fucking perfect.

Almost.

Both of you have left your cell phones on the kitchen table. They’ve buzzed almost half a dozen times, each with text messages and a handful of calls.

Your little black dress collects dust on the floor along with his jeans and flannel.

In the morning, long after he should, Dean wakes up nice and easy.

He just ends up waking alone.

AN: 🫣 Sorry loll. If you think those twists were fun, then get ready for a whole messy love triangle when Brady re-enters from Stage Left. 😬 (And are you curious about Dean and reader's past?)

Next Time:

What have I done?

Okay, you were drunk, but not that drunk.

You were in pain. Reckless. Selfish.

Shame invades your body and settles into your heart. All you can do is slowly, silently slip out of the bed without disturbing Dean. After reclaiming your clothes from the dusty floor and getting dressed, you hold back tears as you try to leave the tangle of desire and old memories, both beautiful and painful, behind you in that room. All you take with you is your phone and the silver necklace you already wear.

Although you wait to put on your heels until you get outside the cabin, that big stretch of hill up ahead to the main house is daunting.

“Mornin’.”

Your head turns sharply at the voice. You shouldn’t be surprised that someone’s already up this early, let alone one of the ranch hands. Benny. He’s tall and broad, like Dean, though with reddish brown hair and a thicker beard. He’s already dressed for the day in jeans and a long-sleeved shirt, drinking his coffee as he leans against the bunkhouse wall. You nod back at him with an awkward smile. 

“How you plan to get up the hill in those pumps?” he asks.

You sigh. “I don’t.”

You’re about to execute the worst walk of shame you’ve ever done, but at least it’s only for an audience of one. You slip off the heels and let the ankle straps dangle from your fingers as you walk barefoot on wet, dewy earth, all the way back up to the house. 

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John's famous barbecue pit spins the mouthwatering smells of smoked meats. The tables are lined up and filled with buttery cornbread, potatoes done three different ways (mashed, roasted, and casseroled), salads, slaw, carrots and corn, wild rice, homemade dinner rolls and garlic bread, and no less than five different flavors of pie. You spy Dean tucking into his third slice of cherry. Evidently, it’s still his favorite. A piece of pastry crust flecks from his lower lip as he jumps in with an old story.

“So I’m maybe…twelve, thirteen. Bobby’s trying to show me how to fix this patch of barbed wire fence. Because I’m young and stupid, I get it in my head to jump over it while the wire’s slack,” Dean starts.

Sam and couple of the cowboys, Benny and Cas, are already smirking, chuckling a little, shaking their heads. They’ve definitely heard this one before, and this time, you have too. A smile curves your lips behind the rim of your glass of whiskey and Coke.

“I make it over, but my leg gets caught in the slack, and I just go down hard, eating the damn dirt,” Dean says. He mimes the impact of his body hitting the ground, complete with admittedly impressive sound effects. “But now the wire’s tight. Rips through my jeans, my ankle, blood soaking through. But, uh, Bobby calms me down, you know. He takes out his tool belt, and he says, ‘It’s all right, son. That’s why God made pliers, for idjits like you.’”

Laughter ripples across the table. Even John smiles, shaking his head.

“Well, he cleaned me up best he could and helped me back up on my horse,” Dean says. His grin is warm, and his gaze spans far beyond his beer. “Dad didn’t even have to lecture me. You remember what you said?”

John nods in amusement. “‘Your own body’s gonna do the punishing for me, son.’”

“Right. My ankle was busted for three weeks. Couldn’t ride, couldn’t do shit,” Dean says with a chuckle. “And it was summer too.”

At least he didn’t have to go to school, but for a boy like Dean, being cooped up in the house was three weeks of misery. All he could do was watch from his bedroom window while you and Sam ran off to ride your bikes in town or go swimming in the river.

He looks down toward the end of the table, wanting to see if you remember those days like he does. What he finds is your empty seat. His eyes run a search—and eventually catch you making your way over to the barn. His brows furrow in confusion, but as the conversation spins and Benny takes over the reminiscing, Dean gets up from the table, ignoring the little warning tug in his gut.

“Gonna get another beer,” he says.

But Sam’s perceptive gaze follows him. While you venture into the barn, Sam sees his brother’s projected path all too clearly.

The smell of horse makes you gag a little, but after you enter the barn and switch on the light, yet another wave of nostalgia blasts you in the face. You recognize that tack and tool shelf on the right-hand corner, and the rack of shotguns and rifles on the far left. You know these stalls, and you greet each of the horses like old friends, even though most of them are new ones.

You stop at one of the middle stalls on the right, clicking your tongue at an older horse. His coat is a deep coffee brown, dappled with white on his hindquarters.

“Dakota! Look at you, handsome.” You smile brightly. “Remember me?”

He blinks at you with those dark eyes, and he meanders a bit closer to the half door. You offer a loosely closed fist for him to inspect. When he does, you think it’s with some familiarity as he sniffs your hand all over. Or maybe he’s just smelling the apple pie glaze you licked off your finger earlier.

You laugh lightly and take a chance on petting the side of his neck. He lets you do it, a kind older statesman. Before you left, you had helped your dad break this horse in.

“He remembers you.”

You turn your head toward the door, flinching slightly in surprise. You didn’t even hear Dean come into the barn. His scuffed boots cross the distance leading him to you. Dark wash jeans and a black buttoned-down shirt are probably the extent of his cleaning up for the occasion, but the ensemble does suit him better than a proper suit would.

“It all looks the same,” you say quietly.

“That’s because it is,” Dean replies. His lips pull at a smirk as he points to the tool shed. “Like that dusty back room where we used to make out.”

You roll your eyes, but you can’t help the way your gaze draws to his calloused hands and long fingers. Your cheeks begin to prickle with warmth, but you refocus on his face, and unfortunately, that familiar grin. You’re sure that face has gotten him plenty of action since then.

“You do remember I have a fiancé,” you say.

Dean nods, holding up a placating hand. It slips into his pocket as he leans against a support beam. “Yeah, you never said where that guy was today.”

“Working,” you reply defensively. “We’re in the middle of a big project, and we can’t afford to drop the ball.”

“You two work together?”

“Yeah, for his father’s company.”

“Doing what?”

You hesitate. It seems like Sam hasn’t spoken to Dean yet about the offer either, but in this case, you’re grateful for it.

“Land development. His father is co-CEO and head of the Legal team. I help scope out properties and propose new projects,” you say.

Dean quirks a brow. “Land development, huh? Not what I would’ve imagined.”

His tone annoys you, making you slightly more tense, but you’ve already had this argument with Sam. You don’t have to explain yourself to this man.

“It’s not what I thought I’d end up in either, but if you think it’s hard to be a rancher, try being able to pay rent in California. We’re all just trying to survive, Dean,” you say.

At that, he actually nods more sincerely.

“Guess that’s fair. But it looks like you’re more than surviving now. You’ve got a friggin’ golf ball on your finger,” he says, gesturing at you, and more specifically your engagement ring.

You roll your eyes. “It’s not that big.”

The way he snorts earns a reluctant smile from you.

“How long you known the guy?” Dean asks.

You give him a shrewd look. He’s very curious about your personal life, but you can’t deny that you’ve been wondering what the past 12 years have made of him.

“About eight months,” you reply.

His brows raise almost as high as his hairline. “Eight months? When did he pop the question?”

“…A few weeks ago,” you say, albeit with some hesitation. “What?”

Dean shakes his head. “Nothing, I guess. Whirlwind romance.”

“And what about you?” you counter, fighting a blush. “No girlfriend?”

Dean chuckles. “Oh, I have plenty of friends. Just no time for the whirlwind.”

“I’m sure,” you say wryly. “Things really don’t change much around here.”

It’s a touch snider than you mean it to be. You don’t actually want to pick another fight. Frankly, you don’t have the emotional energy.

But even though Dean gives you a certain look, to your surprise, he doesn’t want to snipe anymore either. He just sighs.

“All right, come on. There’s some of Bobby’s stuff that you might want to look through,” he says, ushering you to follow him.

You do so reluctantly, over to the Foreman’s cabin.

The Foreman wrangles the other ranch hands, and he’s the Ranch Manager’s second-in-command. Bobby held that position for 23 years, starting from back when John was managing all operations himself. You used to live in this cabin with your mom and dad, back when they were together. 

Dean would later take your virginity when you turned 18—in the glorified closet that used to be your bedroom.

At least he doesn’t bring up that little anecdote as he leads you to the small, four-seater dining table. It has a few boxes stacked on top of it, probably what’s left of your father’s belongings. The rest has been cleared out except for a couch, an old wood coffee table, a TV on a stand, and some supplies in the kitchen. There are some signs of life here though, like a half-drunk beer on the coffee table, an empty box of pizza on the kitchen counter, and some crumpled napkins. Dean notices your observing gaze.

“I’ve been hanging out here the past few days. Cleaning the place up took a while, but uh, sometimes it’s nice to get away from the main house,” he says.

“I could see why. Thirty-two and still living with your daddy,” you teasingly remark.

Dean shoots you an amused brow raise, but he brings the first box to the living room coffee table and slides it toward you.

“Take whatever you want. He doesn’t have any other family, so I’m not sure what to do with the rest,” he says, rubbing a hand at the back of his neck.

Throwing it away feels wrong, or so his tone says. You nod in agreement and start looking through the box. The first thing you find is a large bottle of gold label scotch.

“Wow,” you say.

“That’s on brand,” Dean says, with a smirk. He eyes you. “We should probably crack it open, in Bobby’s honor, of course.”

Your lips tug at a smile. You hand it over, and Dean twists off the cap to take a swig. He offers it back to you, and you accept it dubiously after sitting beside him on the couch.

“You know we’re not teenagers anymore, right?” you say, but you still sip straight from the bottle just like he did, grimacing at the burn down your throat.

“We gotta lubricate this trip down memory lane somehow,” he replies. 

You snort in response and dig back into the box for something else.

Dean’s phone buzzes in his pocket. He checks and sees a text from Sam, asking if he’s with you.

Yeah, we’re going through Bobby’s stuff. I can come help. No need. It’s not that much. …Dude. What’re you doing? What? We’re good. Just catching up. All of a sudden you two are civil? I guess. It’s no big deal. We’ll be back in a few minutes. Ok. Just…be smart about this.

Dean frowns, resenting what his brother is insinuating. He glances up at you.

You haven’t noticed his silent conflict. You’re just looking through old baseball cards and faded trucker hats, rusty tools and piles of weathered flannel.

By the time you get to the third box, over an hour has passed, the bottle of scotch is almost empty, and you’re laughing harder and freer at the stories about Bobby that Dean’s pulling out easier than the next object. You haven’t even noticed that his knee rests against your thigh, or that you occasionally grab his forearm when something he says makes you particularly giggly.

It’s kind of cute that you still do that, but he keeps that thought locked in deep. His smile starts to hurt the corners of his cheeks, though.

Eventually, what you find at the bottom of the last box hits you so hard behind the ribs that it steals your breath. It’s a picture of you and your mom when you were around seven years old: your first year in this cabin, on this ranch.

To you it had seemed like a fun adventure, and so much cooler than your little boring apartment in Salida. Here, there were horses and cows and Sunday barbecues hosted by John Winchester himself.

It was on one of those Sundays that you met Dean, with all those freckles dotted across the bridge of his nose and cheeks, and the purest kind of happiness in his green eyes while he ate a slice of peach cobbler with a scoop of melting homemade ice cream. You remember him setting his own plate aside for a while though, just to comfort his six-year-old brother when his ice cream rolled off the side of his bowl into the dirt. Dean ended up slotting his own ice cream into Sammy’s bowl.

Bobby clocked what happened out of the corner of his eye. In the end, he was the one to slip you and Dean an extra scoop.

Your dad didn’t miss much, at least back then.

“I don’t get it, you know,” you say, somewhat shakily. “When we were kids, Dad was my safe place. Sure, he was gruff and curmudgeonly sometimes, but he was gentle too. He always looked out for me. I understand that shit didn’t work out between him and Mom, but I did try calling him. Years of five-minute conversations that never went anywhere, because he had to get back to the ranch.”

Your lips tremble and you try to blink past the sting, but the dam is already full to bursting, and your walls are failing all over again.

Dean watches you, and he actually listens as his heart grows heavier.

“I was a student. For a long time, I couldn’t afford to fly back to Salida,” you admit. “But he never once came out to visit. He didn’t even go to my college graduation. He showed up to Mom’s funeral. That’s it. I had to call the cemetery, the church, arrange the burial. I had to figure it all out by myself. And I get it, she left him. But he didn’t have to leave me too.”

You press your fingers over your mouth, as if that can stop the hurt from spilling out. You find sympathy in Dean’s eyes, but he doesn’t do what you expect. He rifles through the same collection of memories and pulls out a thin, white box.

Inside is a thin silver chain necklace with a small rose pendant. He lets the chain fall into your hand.

“He was going to give you this at your graduation,” Dean says. “I only know because he was hella fucking drunk one night, and he told me.” 

You laugh a little through unshed tears. You marvel at the necklace; it’s simple, dainty even, but beautiful. 

“Your mom told him not to go,” Dean says, earning your soft shock. “He hadn’t helped you pay for college, so in her mind, he didn’t have a right to see you. At least, that’s what he said happened.” 

“What?” you frown, rubbing the small pendant between your fingers. “I…can’t believe she said that.”

You had a partial scholarship and a work study job, but you wouldn’t have gotten through college without your mom. Living in San Diego hadn’t been easy at first, financially, and your mother was a nurse. You still don’t know how she managed it, but she always came through for you when it was time to pay for the next semester, and even for your textbooks.

You understood that even a Foreman didn’t make a hefty salary. It was part of the reason your mom gave you for leaving your dad. She didn’t come from a ranching family, and she had never wanted to spend her life on a ranch either, let alone one that your parents didn’t own.

In her words, “It’s hard to build a life on someone else’s land.”

She told you that she wanted more for you, and more for herself. Bobby hadn’t been willing to leave Winchester Ranch.

“He was dedicated to it. In some ways it was admirable, but in others…” she’d said, with an edge of bitterness.

You never really understood it. You realize now that you hadn’t tried hard enough. 

“I didn’t care about the fucking money or who paid for what. I just wanted him to be there,” you quietly confess. “But I know that’s a two-way street. I wasn’t there for him either.”

You look up at Dean, meeting his gaze.

“You were right,” you say, as emotion begins to choke you. “He had a goddamn heart attack, and I would’ve never known.”

Your shoulders shake as the first sob wracks through your body, but you soon find warmth and a familiar comfort in Dean’s arms.

“Okay, sweetheart. Come ‘ere,” he says, as he holds you close. There’s something different in his voice. Deep and a little coarse, but gentler. It’s the anchor you need right now, and you cling to it. You cling to him.

“It’s not your fault, okay? Seems like Bobby made his choices too,” Dean says. 

He tucks your head under his chin and briefly closes his eyes as he strokes your back. He feels every hiccup and unsteady breath in you, feels your tears dampening his shirt. His lips press to the crown of your head. Your fingers tangle in the green flannel at his back.

As you begin to relax after crying yourself out, your curled fingers smooth out into warm hands that release his shirt, but ultimately don’t move far, laid flat against his chest. He brushes frizzy strands of hair away from your face and behind your ear. You slowly look up to meet his eyes, with tears clinging to your lashes. Your lipstick is smudged, but you’re still a wonder to him.

It may just be the booze, but he remembers exactly how this used to feel. It cracks open something he’s been paving over, brick by brick. Year after year. He didn’t think this was what it would take to see you again.  

“Jesus,” he murmurs, brushing your cheek with his thumb. “You’re still so fucking beautiful. More, even.”

Your mouth parts with a hint of surprise, and a telling intake of breath. Your lashes lower as your gaze falls—to his lips.

What the hell is this?

You pull away from him, gently guiding his hand down.

He feels the sting of rejection, but also, his shame.

“’M sorry,” he says, looking away.

“…Yeah,” you say eloquently. You feel a prickle of guilt yourself as you wipe your cheeks.

You push yourself off the couch, but your body doesn’t cooperate well. Hard liquor hasn’t been your poison for a hot minute, whiskey least of all. Clearly, it’s remained a favorite of Dean’s.

But he’s far more than a memory you can shove to the back of your mind, especially when he gets up with you—to hold you and stop you from falling. He looks into your eyes, and the conflict in his makes you morbidly curious. What you would give to know what he’s thinking. 

“Just tell me one thing,” he says. “Does he treat you right?”

You frown. “Excuse me?”

His brows raise in challenge. “Come on. Work is work, but how’s he not gonna at least show up here for you?”

It probably makes him some kind of hypocrite, and he fights the voice inside that tells him he’s an idiot. An asshole.

But all you give him is the soft bite of your words.

“Not that it’s any of your business, but like I told you, our jobs are demanding,” you reply, crossing your arms. “He can be very considerate.”

Dean quirks a wry smile. He glances down at that ring, oval-shaped and vintage, putting it mildly. It would look real nice on his Great Aunt Matilda.

“Yeah, with this, huh?” he says, grasping your left hand. “Tell me this is some kind of kooky family heirloom.”

You slip your hand out of his. “He found it at an estate sale.”

“Oh, I believe you,” Dean chuckles. He taps the humble pendant that now has a place above your heart, after he helped you figure out how to put on the necklace it belongs to. “That’s more your speed.”

“How would you know?” you retort, batting his finger off. “It’s been all this time, and you think you still know me?”

You really do walk away from him now, beelining toward the door…

Well, you would have. You will. But his audacity truly is monumental, and after how he treated you this morning, this really is too much for you to wrap your head around. It derails what would’ve been a highly justified storm-out, and compels you back to face him in frustration.

“What’re you trying to do, Dean, spin my head around?” you snap. “You’re the one who broke my heart first. You don’t even know how much you messed me up.”

The confession escapes you before you can cram it back in, shocking you as well as him.

But it’s true.

Years. It had taken you years to get over him, your best friend. Your first real love.

Dean’s amusement faded the more you spoke.

“I know,” he says. And the admission costs him. Under the layers of bravado, bitterness and hurt, there’s the truth. “I was a stupid kid back then, who didn’t know how to let you go.”

You shake your head in denial. Your heart hurts, probably because it never healed right the first time.

“That’s bullshit,” you say. “You didn’t have to let me go. That was your choice.”

“Yeah, I did,” Dean says, with a newfound certainty that dims the light from his eyes. “You had a life ahead of you, sweetheart. Mine was always gonna be on this ranch.”

For a moment, you’re stunned where you stand.

Until reason and doubt start to compete for new ground in your mind.

He’s still making excuses, you think. He could’ve come with you to college. You told him that then, and even if his father tried to nail his boots to the ground, Dean never even called you once after you left. Where was this apology when it would’ve mattered?

“Jesus Christ, Dean…”

You rub your forehead at the headache you already feel coming on. You’re probably drunk, in fairness.

“Why are you telling me all this now?” you ask.

He sighs and rakes a hand through his hair, then rubs his eyes as well.

“Good question,” he chuckles slightly. He sobers when he meets your eyes again. “You told the truth today at the funeral. It’s only fair I give you the same courtesy.”

“Courtesy. Is that what this is?” you challenge.

“It’s an apology,” he says. “And uh, it’s goodbye, stranger, I guess.”

“Goodbye,” you echo. Though you’re unable to stop yourself from glancing down at his lips again. Then back to his eyes, despite the glassiness in yours. A hitch in your breath. “I guess it is.”

Dean sees it, another spark of your tears. He still hates it, both selfishly and unselfishly.

He can’t help but try to give you the stability you need. First, by his slow attempt to hold you, brushing his thumbs against your arms. Your mouth parts, but you don’t pull away.

He bows his head and follows the deep-seated need in his gut, urging him to press his lips to yours.

You breathe in sharply through your nose, but your fingers clench in his shirt again, near his collar. Your body melts willingly against his, like a muscle memory you thought you lost.

Then, the brush of his tongue short-circuits your brain. His hand moves down to the small of your back and presses you into him, eliciting tingles down your spine, and a blooming, pulsing heat between your legs.

You whimper into his mouth, and his hold tightens a fraction.

You pull back for a moment, panting for air. Your eyes meet his incredulously.

He steels himself, waiting for a slap, or at least a push.

You don’t have it in yourself to give him either one. Your heart clenches painfully, because despite the guilt and shame you already feel, something inside you, deeply vulnerable and frayed, needs this.

You tell yourself it’s just one more kiss.

He meets you halfway when you lean up to claim his lips. He claims you back, his hands once again molding to your waist, his arms caging you in, his hand sinking into your hair.

One more turns into him backing you up against the wall. You grab onto his shoulders for leverage, then his hair as his lips veer away from yours to blaze a hot, wet trail down your neck. Your moan is perfect in his ear, rattling down his spine and right to his cock.

You feel him heavy and thick through his jeans, pressing against you. His hand slips up your thigh, squeezing plush flesh as he goes. He bunches the skirt of your dress up to your hips.

“Unzip me,” you tell him, through hushed tones and heated breaths.

Dean nods, turning you around and brushing your hair out of the way so he can drag the zipper down in a slow, torturous tease. His eyes drink in every inch of your skin, but there’s nothing sexier to him than the way you brush down the sleeves and slip out of the dress the rest of the way. The fabric falls around your ankles, and you step out of them in your tall heels. Dean gets the full view of your lace panties, then the matching bra when you turn back around.

He catches your little intake of breath, like you’re guarding yourself before he sees you. He smiles and pulls you back in by your waist.

“Like I said, fucking beautiful,” he says, his gaze roaming your face.

Your lips tug at a smile as you meet his stare, but he finally renders you without a snappy word to say. He takes that win and revels in it as he kisses you.

You touch him more confidently than he remembers, dragging your nails down the back of his neck, sucking his tongue into your mouth, down to grabbing onto his belt and popping the buckle open. He follows your lead and helps you loosen his belt and jeans, but his boots and your heels are the first to form a haphazard pile on the way into the bigger bedroom, where his spare sheets and an old comforter line the bed.

He wasn’t lying to you when he said he’s been staying over here for the past few days. Not only so that he could clean up, but because he needed to clear his own head. Bobby’s death shook everyone, but it hit Dean in a way he hadn’t expected. He hasn’t told anyone this, but it was like losing a second father.

It reminded Dean of his regrets—his biggest one of all being you.

Despite how it looks, he knows it’s wrong to touch you. He knows it’s selfish to want you. But he hasn’t allowed himself to want anything in such a long time, and he thinks he might be able to right some old wrongs while he’s busy committing new ones.

After he lays you on the bed underneath him, Dean kisses his way along the column of your throat, down between your breasts. He slips a hand underneath you to unhook the pretty lace bra, and your back arches, giving him room. 

You really have grown up beautifully, even your boobs. Good for you, and good for him. Dean recommits them to memory as his tongue lavishes one of your nipples, while his right hand rolls the other between his thumb and forefinger. You sigh his name and slip your fingers through his hair, scratching his scalp with your nails. But your fingers hook on his flannel next.

“Take this off,” you breathe. “Want to see you too.”

Dean hesitates, but concedes to taking off his outer flannel. His undershirt stays on, even though you tug on it next. He aims to distract you by moving further down your body, laying open-mouthed kisses down your ribs and stomach, and over your mound, after he slips off your panties. He glances up between your legs and shoots you a mischievous grin.

“I used to love the way you tasted,” he says. “Those little sounds you made, the way you’d buck against my chin and scream my name… Let’s see if we can rock another sequel, huh, sweetheart?” 

“Dean,” you gasp, as his fingers slip between the folds of your pussy. They find slick arousal and heat.

“Jesus,” he murmurs. “You’re soaking wet.”

He bites his lower lip as his thumb searches, then finds your clit. Your hips start to writhe as you moan, grinding against his hand. He smirks in satisfaction before he lowers down. He moves your left thigh over his shoulder, and he feasts.

Your mouth falls open in a near silent cry, and your hips nearly come off the bed as you feel his tongue replace his fingers on your clit. Those long digits slip inside your hot channel. Hunger pools in your lower belly as your inner walls clench on him, desperately needing friction. Your breaths deepen as your free hand goes to your breast, toying with a hard nipple while you savor the sensations Dean’s giving you with his mouth and skilled fingers.

He curls his fingers and strokes you deeply, searching, exploring, until he finds that most sensitive place within your inner walls that has your body shuddering like an accordion. You grab a fistful of his hair as you buck hard against his mouth, a choked scream falling from your lips.

After withdrawing his fingers and wiping his mouth and nose, he presses a kiss into your inner thigh as you still tremble with the aftershocks of your orgasm.

He moves back up your body, and you take his face in your hands to kiss him deeply.

“What’s the verdict?” he teases afterward.

“You’ve gotten better,” you admit.

You sit up, intending to return the favor as your hands roam down his chest and underneath his shirt. He feels toned from long hours of hard labor and horse riding, but he stills your hands from grasping at the edge of his shirt. You’re confused, but he quickly guides you into turning over in the bed.

He kneels behind you as his steady hands continue to map every inch of your body. He caresses your sides, across your middle, and back up to your breasts while he kisses along your neck, then down your shoulder. There’s more calm confidence in his touch than he had at 20 years old, certainly more strength and more callouses, but it’s a delicious friction. And it’s a feeling that he absolutely has you enveloped in his arms, within his broad frame. You hang onto him on reflex.

Two of his fingers dip back into your pussy, circling your clit. You hang onto his arm as your body gives way to a moan. Arousal begins to pulse deep inside you again, but this time, you need his cock. You want to know if he’s improved there too. He seems to remember your body well enough.

“Dean…just fuck me,” you whisper coarsely. “Please…”

Before I lose my nerve.

“I gotcha, sweetheart,” he says, in a voice like old scotch and honey. Its depths make prickles of heat flash across your skin as fabric rustles. You assume he’s finally stripping off the rest of his clothes. You catch a glimpse over your shoulder of him tossing his shirt and boxers to the floor, but soon, the heat of his presence returns as he lines himself up at your entrance. His cock finally pushing inside you from behind makes your thighs tremble. Your nails dig into the mattress sheets.

“Dean,” you gasp. He stretches you so fucking good.

“You’ve got it, baby. Every damn inch, doing so good,” he says, breathing hard into your neck. His teeth graze your shoulder, making you shudder and push into him on reflex, sheathing him nice and snug inside. Already the walls of your cunt tremble around his cock.

Dean keeps his promise; it’s dewy skin against skin as holds you to him while he fucks you, slow, deep, and powerful, but never painful. Never too much.

He asks you what you want—faster or slower, rougher, or easier rhythm. You tell him you want him exactly how he is: fucking perfect.

And that night, it is fucking perfect.

Almost.

Both of you have left your cell phones on the kitchen table. They’ve buzzed almost half a dozen times, each with text messages and a handful of calls.

Your little black dress collects dust on the floor along with his jeans and flannel.

In the morning, long after he should, Dean wakes up nice and easy.

He just ends up waking alone.

AN: 🫣 Sorry loll. If you think those twists were fun, then get ready for a whole messy love triangle when Brady re-enters from Stage Left. 😬 (And are you curious about Dean and reader's past?)

Next Time:

What have I done?

Okay, you were drunk, but not that drunk.

You were in pain. Reckless. Selfish.

Shame invades your body and settles into your heart. All you can do is slowly, silently slip out of the bed without disturbing Dean. After reclaiming your clothes from the dusty floor and getting dressed, you hold back tears as you try to leave the tangle of desire and old memories, both beautiful and painful, behind you in that room. All you take with you is your phone and the silver necklace you already wear.

Although you wait to put on your heels until you get outside the cabin, that big stretch of hill up ahead to the main house is daunting.

“Mornin’.”

Your head turns sharply at the voice. You shouldn’t be surprised that someone’s already up this early, let alone one of the ranch hands. Benny. He’s tall and broad, like Dean, though with reddish brown hair and a thicker beard. He’s already dressed for the day in jeans and a long-sleeved shirt, drinking his coffee as he leans against the bunkhouse wall. You nod back at him with an awkward smile. 

“How you plan to get up the hill in those pumps?” he asks.

You sigh. “I don’t.”

You’re about to execute the worst walk of shame you’ve ever done, but at least it’s only for an audience of one. You slip off the heels and let the ankle straps dangle from your fingers as you walk barefoot on wet, dewy earth, all the way back up to the house. 

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John's famous barbecue pit spins the mouthwatering smells of smoked meats. The tables are lined up and filled with buttery cornbread, potatoes done three different ways (mashed, roasted, and casseroled), salads, slaw, carrots and corn, wild rice, homemade dinner rolls and garlic bread, and no less than five different flavors of pie. You spy Dean tucking into his third slice of cherry. Evidently, it’s still his favorite. A piece of pastry crust flecks from his lower lip as he jumps in with an old story.

“So I’m maybe…twelve, thirteen. Bobby’s trying to show me how to fix this patch of barbed wire fence. Because I’m young and stupid, I get it in my head to jump over it while the wire’s slack,” Dean starts.

Sam and couple of the cowboys, Benny and Cas, are already smirking, chuckling a little, shaking their heads. They’ve definitely heard this one before, and this time, you have too. A smile curves your lips behind the rim of your glass of whiskey and Coke.

“I make it over, but my leg gets caught in the slack, and I just go down hard, eating the damn dirt,” Dean says. He mimes the impact of his body hitting the ground, complete with admittedly impressive sound effects. “But now the wire’s tight. Rips through my jeans, my ankle, blood soaking through. But, uh, Bobby calms me down, you know. He takes out his tool belt, and he says, ‘It’s all right, son. That’s why God made pliers, for idjits like you.’”

Laughter ripples across the table. Even John smiles, shaking his head.

“Well, he cleaned me up best he could and helped me back up on my horse,” Dean says. His grin is warm, and his gaze spans far beyond his beer. “Dad didn’t even have to lecture me. You remember what you said?”

John nods in amusement. “‘Your own body’s gonna do the punishing for me, son.’”

“Right. My ankle was busted for three weeks. Couldn’t ride, couldn’t do shit,” Dean says with a chuckle. “And it was summer too.”

At least he didn’t have to go to school, but for a boy like Dean, being cooped up in the house was three weeks of misery. All he could do was watch from his bedroom window while you and Sam ran off to ride your bikes in town or go swimming in the river.

He looks down toward the end of the table, wanting to see if you remember those days like he does. What he finds is your empty seat. His eyes run a search—and eventually catch you making your way over to the barn. His brows furrow in confusion, but as the conversation spins and Benny takes over the reminiscing, Dean gets up from the table, ignoring the little warning tug in his gut.

“Gonna get another beer,” he says.

But Sam’s perceptive gaze follows him. While you venture into the barn, Sam sees his brother’s projected path all too clearly.

The smell of horse makes you gag a little, but after you enter the barn and switch on the light, yet another wave of nostalgia blasts you in the face. You recognize that tack and tool shelf on the right-hand corner, and the rack of shotguns and rifles on the far left. You know these stalls, and you greet each of the horses like old friends, even though most of them are new ones.

You stop at one of the middle stalls on the right, clicking your tongue at an older horse. His coat is a deep coffee brown, dappled with white on his hindquarters.

“Dakota! Look at you, handsome.” You smile brightly. “Remember me?”

He blinks at you with those dark eyes, and he meanders a bit closer to the half door. You offer a loosely closed fist for him to inspect. When he does, you think it’s with some familiarity as he sniffs your hand all over. Or maybe he’s just smelling the apple pie glaze you licked off your finger earlier.

You laugh lightly and take a chance on petting the side of his neck. He lets you do it, a kind older statesman. Before you left, you had helped your dad break this horse in.

“He remembers you.”

You turn your head toward the door, flinching slightly in surprise. You didn’t even hear Dean come into the barn. His scuffed boots cross the distance leading him to you. Dark wash jeans and a black buttoned-down shirt are probably the extent of his cleaning up for the occasion, but the ensemble does suit him better than a proper suit would.

“It all looks the same,” you say quietly.

“That’s because it is,” Dean replies. His lips pull at a smirk as he points to the tool shed. “Like that dusty back room where we used to make out.”

You roll your eyes, but you can’t help the way your gaze draws to his calloused hands and long fingers. Your cheeks begin to prickle with warmth, but you refocus on his face, and unfortunately, that familiar grin. You’re sure that face has gotten him plenty of action since then.

“You do remember I have a fiancé,” you say.

Dean nods, holding up a placating hand. It slips into his pocket as he leans against a support beam. “Yeah, you never said where that guy was today.”

“Working,” you reply defensively. “We’re in the middle of a big project, and we can’t afford to drop the ball.”

“You two work together?”

“Yeah, for his father’s company.”

“Doing what?”

You hesitate. It seems like Sam hasn’t spoken to Dean yet about the offer either, but in this case, you’re grateful for it.

“Land development. His father is co-CEO and head of the Legal team. I help scope out properties and propose new projects,” you say.

Dean quirks a brow. “Land development, huh? Not what I would’ve imagined.”

His tone annoys you, making you slightly more tense, but you’ve already had this argument with Sam. You don’t have to explain yourself to this man.

“It’s not what I thought I’d end up in either, but if you think it’s hard to be a rancher, try being able to pay rent in California. We’re all just trying to survive, Dean,” you say.

At that, he actually nods more sincerely.

“Guess that’s fair. But it looks like you’re more than surviving now. You’ve got a friggin’ golf ball on your finger,” he says, gesturing at you, and more specifically your engagement ring.

You roll your eyes. “It’s not that big.”

The way he snorts earns a reluctant smile from you.

“How long you known the guy?” Dean asks.

You give him a shrewd look. He’s very curious about your personal life, but you can’t deny that you’ve been wondering what the past 12 years have made of him.

“About eight months,” you reply.

His brows raise almost as high as his hairline. “Eight months? When did he pop the question?”

“…A few weeks ago,” you say, albeit with some hesitation. “What?”

Dean shakes his head. “Nothing, I guess. Whirlwind romance.”

“And what about you?” you counter, fighting a blush. “No girlfriend?”

Dean chuckles. “Oh, I have plenty of friends. Just no time for the whirlwind.”

“I’m sure,” you say wryly. “Things really don’t change much around here.”

It’s a touch snider than you mean it to be. You don’t actually want to pick another fight. Frankly, you don’t have the emotional energy.

But even though Dean gives you a certain look, to your surprise, he doesn’t want to snipe anymore either. He just sighs.

“All right, come on. There’s some of Bobby’s stuff that you might want to look through,” he says, ushering you to follow him.

You do so reluctantly, over to the Foreman’s cabin.

The Foreman wrangles the other ranch hands, and he’s the Ranch Manager’s second-in-command. Bobby held that position for 23 years, starting from back when John was managing all operations himself. You used to live in this cabin with your mom and dad, back when they were together. 

Dean would later take your virginity when you turned 18—in the glorified closet that used to be your bedroom.

At least he doesn’t bring up that little anecdote as he leads you to the small, four-seater dining table. It has a few boxes stacked on top of it, probably what’s left of your father’s belongings. The rest has been cleared out except for a couch, an old wood coffee table, a TV on a stand, and some supplies in the kitchen. There are some signs of life here though, like a half-drunk beer on the coffee table, an empty box of pizza on the kitchen counter, and some crumpled napkins. Dean notices your observing gaze.

“I’ve been hanging out here the past few days. Cleaning the place up took a while, but uh, sometimes it’s nice to get away from the main house,” he says.

“I could see why. Thirty-two and still living with your daddy,” you teasingly remark.

Dean shoots you an amused brow raise, but he brings the first box to the living room coffee table and slides it toward you.

“Take whatever you want. He doesn’t have any other family, so I’m not sure what to do with the rest,” he says, rubbing a hand at the back of his neck.

Throwing it away feels wrong, or so his tone says. You nod in agreement and start looking through the box. The first thing you find is a large bottle of gold label scotch.

“Wow,” you say.

“That’s on brand,” Dean says, with a smirk. He eyes you. “We should probably crack it open, in Bobby’s honor, of course.”

Your lips tug at a smile. You hand it over, and Dean twists off the cap to take a swig. He offers it back to you, and you accept it dubiously after sitting beside him on the couch.

“You know we’re not teenagers anymore, right?” you say, but you still sip straight from the bottle just like he did, grimacing at the burn down your throat.

“We gotta lubricate this trip down memory lane somehow,” he replies. 

You snort in response and dig back into the box for something else.

Dean’s phone buzzes in his pocket. He checks and sees a text from Sam, asking if he’s with you.

Yeah, we’re going through Bobby’s stuff. I can come help. No need. It’s not that much. …Dude. What’re you doing? What? We’re good. Just catching up. All of a sudden you two are civil? I guess. It’s no big deal. We’ll be back in a few minutes. Ok. Just…be smart about this.

Dean frowns, resenting what his brother is insinuating. He glances up at you.

You haven’t noticed his silent conflict. You’re just looking through old baseball cards and faded trucker hats, rusty tools and piles of weathered flannel.

By the time you get to the third box, over an hour has passed, the bottle of scotch is almost empty, and you’re laughing harder and freer at the stories about Bobby that Dean’s pulling out easier than the next object. You haven’t even noticed that his knee rests against your thigh, or that you occasionally grab his forearm when something he says makes you particularly giggly.

It’s kind of cute that you still do that, but he keeps that thought locked in deep. His smile starts to hurt the corners of his cheeks, though.

Eventually, what you find at the bottom of the last box hits you so hard behind the ribs that it steals your breath. It’s a picture of you and your mom when you were around seven years old: your first year in this cabin, on this ranch.

To you it had seemed like a fun adventure, and so much cooler than your little boring apartment in Salida. Here, there were horses and cows and Sunday barbecues hosted by John Winchester himself.

It was on one of those Sundays that you met Dean, with all those freckles dotted across the bridge of his nose and cheeks, and the purest kind of happiness in his green eyes while he ate a slice of peach cobbler with a scoop of melting homemade ice cream. You remember him setting his own plate aside for a while though, just to comfort his six-year-old brother when his ice cream rolled off the side of his bowl into the dirt. Dean ended up slotting his own ice cream into Sammy’s bowl.

Bobby clocked what happened out of the corner of his eye. In the end, he was the one to slip you and Dean an extra scoop.

Your dad didn’t miss much, at least back then.

“I don’t get it, you know,” you say, somewhat shakily. “When we were kids, Dad was my safe place. Sure, he was gruff and curmudgeonly sometimes, but he was gentle too. He always looked out for me. I understand that shit didn’t work out between him and Mom, but I did try calling him. Years of five-minute conversations that never went anywhere, because he had to get back to the ranch.”

Your lips tremble and you try to blink past the sting, but the dam is already full to bursting, and your walls are failing all over again.

Dean watches you, and he actually listens as his heart grows heavier.

“I was a student. For a long time, I couldn’t afford to fly back to Salida,” you admit. “But he never once came out to visit. He didn’t even go to my college graduation. He showed up to Mom’s funeral. That’s it. I had to call the cemetery, the church, arrange the burial. I had to figure it all out by myself. And I get it, she left him. But he didn’t have to leave me too.”

You press your fingers over your mouth, as if that can stop the hurt from spilling out. You find sympathy in Dean’s eyes, but he doesn’t do what you expect. He rifles through the same collection of memories and pulls out a thin, white box.

Inside is a thin silver chain necklace with a small rose pendant. He lets the chain fall into your hand.

“He was going to give you this at your graduation,” Dean says. “I only know because he was hella fucking drunk one night, and he told me.” 

You laugh a little through unshed tears. You marvel at the necklace; it’s simple, dainty even, but beautiful. 

“Your mom told him not to go,” Dean says, earning your soft shock. “He hadn’t helped you pay for college, so in her mind, he didn’t have a right to see you. At least, that’s what he said happened.” 

“What?” you frown, rubbing the small pendant between your fingers. “I…can’t believe she said that.”

You had a partial scholarship and a work study job, but you wouldn’t have gotten through college without your mom. Living in San Diego hadn’t been easy at first, financially, and your mother was a nurse. You still don’t know how she managed it, but she always came through for you when it was time to pay for the next semester, and even for your textbooks.

You understood that even a Foreman didn’t make a hefty salary. It was part of the reason your mom gave you for leaving your dad. She didn’t come from a ranching family, and she had never wanted to spend her life on a ranch either, let alone one that your parents didn’t own.

In her words, “It’s hard to build a life on someone else’s land.”

She told you that she wanted more for you, and more for herself. Bobby hadn’t been willing to leave Winchester Ranch.

“He was dedicated to it. In some ways it was admirable, but in others…” she’d said, with an edge of bitterness.

You never really understood it. You realize now that you hadn’t tried hard enough. 

“I didn’t care about the fucking money or who paid for what. I just wanted him to be there,” you quietly confess. “But I know that’s a two-way street. I wasn’t there for him either.”

You look up at Dean, meeting his gaze.

“You were right,” you say, as emotion begins to choke you. “He had a goddamn heart attack, and I would’ve never known.”

Your shoulders shake as the first sob wracks through your body, but you soon find warmth and a familiar comfort in Dean’s arms.

“Okay, sweetheart. Come ‘ere,” he says, as he holds you close. There’s something different in his voice. Deep and a little coarse, but gentler. It’s the anchor you need right now, and you cling to it. You cling to him.

“It’s not your fault, okay? Seems like Bobby made his choices too,” Dean says. 

He tucks your head under his chin and briefly closes his eyes as he strokes your back. He feels every hiccup and unsteady breath in you, feels your tears dampening his shirt. His lips press to the crown of your head. Your fingers tangle in the green flannel at his back.

As you begin to relax after crying yourself out, your curled fingers smooth out into warm hands that release his shirt, but ultimately don’t move far, laid flat against his chest. He brushes frizzy strands of hair away from your face and behind your ear. You slowly look up to meet his eyes, with tears clinging to your lashes. Your lipstick is smudged, but you’re still a wonder to him.

It may just be the booze, but he remembers exactly how this used to feel. It cracks open something he’s been paving over, brick by brick. Year after year. He didn’t think this was what it would take to see you again.  

“Jesus,” he murmurs, brushing your cheek with his thumb. “You’re still so fucking beautiful. More, even.”

Your mouth parts with a hint of surprise, and a telling intake of breath. Your lashes lower as your gaze falls—to his lips.

What the hell is this?

You pull away from him, gently guiding his hand down.

He feels the sting of rejection, but also, his shame.

“’M sorry,” he says, looking away.

“…Yeah,” you say eloquently. You feel a prickle of guilt yourself as you wipe your cheeks.

You push yourself off the couch, but your body doesn’t cooperate well. Hard liquor hasn’t been your poison for a hot minute, whiskey least of all. Clearly, it’s remained a favorite of Dean’s.

But he’s far more than a memory you can shove to the back of your mind, especially when he gets up with you—to hold you and stop you from falling. He looks into your eyes, and the conflict in his makes you morbidly curious. What you would give to know what he’s thinking. 

“Just tell me one thing,” he says. “Does he treat you right?”

You frown. “Excuse me?”

His brows raise in challenge. “Come on. Work is work, but how’s he not gonna at least show up here for you?”

It probably makes him some kind of hypocrite, and he fights the voice inside that tells him he’s an idiot. An asshole.

But all you give him is the soft bite of your words.

“Not that it’s any of your business, but like I told you, our jobs are demanding,” you reply, crossing your arms. “He can be very considerate.”

Dean quirks a wry smile. He glances down at that ring, oval-shaped and vintage, putting it mildly. It would look real nice on his Great Aunt Matilda.

“Yeah, with this, huh?” he says, grasping your left hand. “Tell me this is some kind of kooky family heirloom.”

You slip your hand out of his. “He found it at an estate sale.”

“Oh, I believe you,” Dean chuckles. He taps the humble pendant that now has a place above your heart, after he helped you figure out how to put on the necklace it belongs to. “That’s more your speed.”

“How would you know?” you retort, batting his finger off. “It’s been all this time, and you think you still know me?”

You really do walk away from him now, beelining toward the door…

Well, you would have. You will. But his audacity truly is monumental, and after how he treated you this morning, this really is too much for you to wrap your head around. It derails what would’ve been a highly justified storm-out, and compels you back to face him in frustration.

“What’re you trying to do, Dean, spin my head around?” you snap. “You’re the one who broke my heart first. You don’t even know how much you messed me up.”

The confession escapes you before you can cram it back in, shocking you as well as him.

But it’s true.

Years. It had taken you years to get over him, your best friend. Your first real love.

Dean’s amusement faded the more you spoke.

“I know,” he says. And the admission costs him. Under the layers of bravado, bitterness and hurt, there’s the truth. “I was a stupid kid back then, who didn’t know how to let you go.”

You shake your head in denial. Your heart hurts, probably because it never healed right the first time.

“That’s bullshit,” you say. “You didn’t have to let me go. That was your choice.”

“Yeah, I did,” Dean says, with a newfound certainty that dims the light from his eyes. “You had a life ahead of you, sweetheart. Mine was always gonna be on this ranch.”

For a moment, you’re stunned where you stand.

Until reason and doubt start to compete for new ground in your mind.

He’s still making excuses, you think. He could’ve come with you to college. You told him that then, and even if his father tried to nail his boots to the ground, Dean never even called you once after you left. Where was this apology when it would’ve mattered?

“Jesus Christ, Dean…”

You rub your forehead at the headache you already feel coming on. You’re probably drunk, in fairness.

“Why are you telling me all this now?” you ask.

He sighs and rakes a hand through his hair, then rubs his eyes as well.

“Good question,” he chuckles slightly. He sobers when he meets your eyes again. “You told the truth today at the funeral. It’s only fair I give you the same courtesy.”

“Courtesy. Is that what this is?” you challenge.

“It’s an apology,” he says. “And uh, it’s goodbye, stranger, I guess.”

“Goodbye,” you echo. Though you’re unable to stop yourself from glancing down at his lips again. Then back to his eyes, despite the glassiness in yours. A hitch in your breath. “I guess it is.”

Dean sees it, another spark of your tears. He still hates it, both selfishly and unselfishly.

He can’t help but try to give you the stability you need. First, by his slow attempt to hold you, brushing his thumbs against your arms. Your mouth parts, but you don’t pull away.

He bows his head and follows the deep-seated need in his gut, urging him to press his lips to yours.

You breathe in sharply through your nose, but your fingers clench in his shirt again, near his collar. Your body melts willingly against his, like a muscle memory you thought you lost.

Then, the brush of his tongue short-circuits your brain. His hand moves down to the small of your back and presses you into him, eliciting tingles down your spine, and a blooming, pulsing heat between your legs.

You whimper into his mouth, and his hold tightens a fraction.

You pull back for a moment, panting for air. Your eyes meet his incredulously.

He steels himself, waiting for a slap, or at least a push.

You don’t have it in yourself to give him either one. Your heart clenches painfully, because despite the guilt and shame you already feel, something inside you, deeply vulnerable and frayed, needs this.

You tell yourself it’s just one more kiss.

He meets you halfway when you lean up to claim his lips. He claims you back, his hands once again molding to your waist, his arms caging you in, his hand sinking into your hair.

One more turns into him backing you up against the wall. You grab onto his shoulders for leverage, then his hair as his lips veer away from yours to blaze a hot, wet trail down your neck. Your moan is perfect in his ear, rattling down his spine and right to his cock.

You feel him heavy and thick through his jeans, pressing against you. His hand slips up your thigh, squeezing plush flesh as he goes. He bunches the skirt of your dress up to your hips.

“Unzip me,” you tell him, through hushed tones and heated breaths.

Dean nods, turning you around and brushing your hair out of the way so he can drag the zipper down in a slow, torturous tease. His eyes drink in every inch of your skin, but there’s nothing sexier to him than the way you brush down the sleeves and slip out of the dress the rest of the way. The fabric falls around your ankles, and you step out of them in your tall heels. Dean gets the full view of your lace panties, then the matching bra when you turn back around.

He catches your little intake of breath, like you’re guarding yourself before he sees you. He smiles and pulls you back in by your waist.

“Like I said, fucking beautiful,” he says, his gaze roaming your face.

Your lips tug at a smile as you meet his stare, but he finally renders you without a snappy word to say. He takes that win and revels in it as he kisses you.

You touch him more confidently than he remembers, dragging your nails down the back of his neck, sucking his tongue into your mouth, down to grabbing onto his belt and popping the buckle open. He follows your lead and helps you loosen his belt and jeans, but his boots and your heels are the first to form a haphazard pile on the way into the bigger bedroom, where his spare sheets and an old comforter line the bed.

He wasn’t lying to you when he said he’s been staying over here for the past few days. Not only so that he could clean up, but because he needed to clear his own head. Bobby’s death shook everyone, but it hit Dean in a way he hadn’t expected. He hasn’t told anyone this, but it was like losing a second father.

It reminded Dean of his regrets—his biggest one of all being you.

Despite how it looks, he knows it’s wrong to touch you. He knows it’s selfish to want you. But he hasn’t allowed himself to want anything in such a long time, and he thinks he might be able to right some old wrongs while he’s busy committing new ones.

After he lays you on the bed underneath him, Dean kisses his way along the column of your throat, down between your breasts. He slips a hand underneath you to unhook the pretty lace bra, and your back arches, giving him room. 

You really have grown up beautifully, even your boobs. Good for you, and good for him. Dean recommits them to memory as his tongue lavishes one of your nipples, while his right hand rolls the other between his thumb and forefinger. You sigh his name and slip your fingers through his hair, scratching his scalp with your nails. But your fingers hook on his flannel next.

“Take this off,” you breathe. “Want to see you too.”

Dean hesitates, but concedes to taking off his outer flannel. His undershirt stays on, even though you tug on it next. He aims to distract you by moving further down your body, laying open-mouthed kisses down your ribs and stomach, and over your mound, after he slips off your panties. He glances up between your legs and shoots you a mischievous grin.

“I used to love the way you tasted,” he says. “Those little sounds you made, the way you’d buck against my chin and scream my name… Let’s see if we can rock another sequel, huh, sweetheart?” 

“Dean,” you gasp, as his fingers slip between the folds of your pussy. They find slick arousal and heat.

“Jesus,” he murmurs. “You’re soaking wet.”

He bites his lower lip as his thumb searches, then finds your clit. Your hips start to writhe as you moan, grinding against his hand. He smirks in satisfaction before he lowers down. He moves your left thigh over his shoulder, and he feasts.

Your mouth falls open in a near silent cry, and your hips nearly come off the bed as you feel his tongue replace his fingers on your clit. Those long digits slip inside your hot channel. Hunger pools in your lower belly as your inner walls clench on him, desperately needing friction. Your breaths deepen as your free hand goes to your breast, toying with a hard nipple while you savor the sensations Dean’s giving you with his mouth and skilled fingers.

He curls his fingers and strokes you deeply, searching, exploring, until he finds that most sensitive place within your inner walls that has your body shuddering like an accordion. You grab a fistful of his hair as you buck hard against his mouth, a choked scream falling from your lips.

After withdrawing his fingers and wiping his mouth and nose, he presses a kiss into your inner thigh as you still tremble with the aftershocks of your orgasm.

He moves back up your body, and you take his face in your hands to kiss him deeply.

“What’s the verdict?” he teases afterward.

“You’ve gotten better,” you admit.

You sit up, intending to return the favor as your hands roam down his chest and underneath his shirt. He feels toned from long hours of hard labor and horse riding, but he stills your hands from grasping at the edge of his shirt. You’re confused, but he quickly guides you into turning over in the bed.

He kneels behind you as his steady hands continue to map every inch of your body. He caresses your sides, across your middle, and back up to your breasts while he kisses along your neck, then down your shoulder. There’s more calm confidence in his touch than he had at 20 years old, certainly more strength and more callouses, but it’s a delicious friction. And it’s a feeling that he absolutely has you enveloped in his arms, within his broad frame. You hang onto him on reflex.

Two of his fingers dip back into your pussy, circling your clit. You hang onto his arm as your body gives way to a moan. Arousal begins to pulse deep inside you again, but this time, you need his cock. You want to know if he’s improved there too. He seems to remember your body well enough.

“Dean…just fuck me,” you whisper coarsely. “Please…”

Before I lose my nerve.

“I gotcha, sweetheart,” he says, in a voice like old scotch and honey. Its depths make prickles of heat flash across your skin as fabric rustles. You assume he’s finally stripping off the rest of his clothes. You catch a glimpse over your shoulder of him tossing his shirt and boxers to the floor, but soon, the heat of his presence returns as he lines himself up at your entrance. His cock finally pushing inside you from behind makes your thighs tremble. Your nails dig into the mattress sheets.

“Dean,” you gasp. He stretches you so fucking good.

“You’ve got it, baby. Every damn inch, doing so good,” he says, breathing hard into your neck. His teeth graze your shoulder, making you shudder and push into him on reflex, sheathing him nice and snug inside. Already the walls of your cunt tremble around his cock.

Dean keeps his promise; it’s dewy skin against skin as holds you to him while he fucks you, slow, deep, and powerful, but never painful. Never too much.

He asks you what you want—faster or slower, rougher, or easier rhythm. You tell him you want him exactly how he is: fucking perfect.

And that night, it is fucking perfect.

Almost.

Both of you have left your cell phones on the kitchen table. They’ve buzzed almost half a dozen times, each with text messages and a handful of calls.

Your little black dress collects dust on the floor along with his jeans and flannel.

In the morning, long after he should, Dean wakes up nice and easy.

He just ends up waking alone.

AN: 🫣 Sorry loll. If you think those twists were fun, then get ready for a whole messy love triangle when Brady re-enters from Stage Left. 😬 (And are you curious about Dean and reader's past?)

Next Time:

What have I done?

Okay, you were drunk, but not that drunk.

You were in pain. Reckless. Selfish.

Shame invades your body and settles into your heart. All you can do is slowly, silently slip out of the bed without disturbing Dean. After reclaiming your clothes from the dusty floor and getting dressed, you hold back tears as you try to leave the tangle of desire and old memories, both beautiful and painful, behind you in that room. All you take with you is your phone and the silver necklace you already wear.

Although you wait to put on your heels until you get outside the cabin, that big stretch of hill up ahead to the main house is daunting.

“Mornin’.”

Your head turns sharply at the voice. You shouldn’t be surprised that someone’s already up this early, let alone one of the ranch hands. Benny. He’s tall and broad, like Dean, though with reddish brown hair and a thicker beard. He’s already dressed for the day in jeans and a long-sleeved shirt, drinking his coffee as he leans against the bunkhouse wall. You nod back at him with an awkward smile. 

“How you plan to get up the hill in those pumps?” he asks.

You sigh. “I don’t.”

You’re about to execute the worst walk of shame you’ve ever done, but at least it’s only for an audience of one. You slip off the heels and let the ankle straps dangle from your fingers as you walk barefoot on wet, dewy earth, all the way back up to the house. 

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I just knew the second these two went off alone (just like Sam pegged it), the kissing and all that comes after would start. Like they shouldn't have but...there's still history there and on a day like that, a parent's funeral, who does and doesn't show up reveals a lot about a person. They really are kindred spirits and surprisingly forgiving in some moments but there's so much history there too, too much shared pain.

John's famous barbecue pit spins the mouthwatering smells of smoked meats. The tables are lined up and filled with buttery cornbread, potatoes done three different ways (mashed, roasted, and casseroled), salads, slaw, carrots and corn, wild rice, homemade dinner rolls and garlic bread, and no less than five different flavors of pie. You spy Dean tucking into his third slice of cherry. Evidently, it’s still his favorite. A piece of pastry crust flecks from his lower lip as he jumps in with an old story.

“So I’m maybe…twelve, thirteen. Bobby’s trying to show me how to fix this patch of barbed wire fence. Because I’m young and stupid, I get it in my head to jump over it while the wire’s slack,” Dean starts.

Sam and couple of the cowboys, Benny and Cas, are already smirking, chuckling a little, shaking their heads. They’ve definitely heard this one before, and this time, you have too. A smile curves your lips behind the rim of your glass of whiskey and Coke.

“I make it over, but my leg gets caught in the slack, and I just go down hard, eating the damn dirt,” Dean says. He mimes the impact of his body hitting the ground, complete with admittedly impressive sound effects. “But now the wire’s tight. Rips through my jeans, my ankle, blood soaking through. But, uh, Bobby calms me down, you know. He takes out his tool belt, and he says, ‘It’s all right, son. That’s why God made pliers, for idjits like you.’”

Laughter ripples across the table. Even John smiles, shaking his head.

“Well, he cleaned me up best he could and helped me back up on my horse,” Dean says. His grin is warm, and his gaze spans far beyond his beer. “Dad didn’t even have to lecture me. You remember what you said?”

John nods in amusement. “‘Your own body’s gonna do the punishing for me, son.’”

“Right. My ankle was busted for three weeks. Couldn’t ride, couldn’t do shit,” Dean says with a chuckle. “And it was summer too.”

At least he didn’t have to go to school, but for a boy like Dean, being cooped up in the house was three weeks of misery. All he could do was watch from his bedroom window while you and Sam ran off to ride your bikes in town or go swimming in the river.

He looks down toward the end of the table, wanting to see if you remember those days like he does. What he finds is your empty seat. His eyes run a search—and eventually catch you making your way over to the barn. His brows furrow in confusion, but as the conversation spins and Benny takes over the reminiscing, Dean gets up from the table, ignoring the little warning tug in his gut.

“Gonna get another beer,” he says.

But Sam’s perceptive gaze follows him. While you venture into the barn, Sam sees his brother’s projected path all too clearly.

The smell of horse makes you gag a little, but after you enter the barn and switch on the light, yet another wave of nostalgia blasts you in the face. You recognize that tack and tool shelf on the right-hand corner, and the rack of shotguns and rifles on the far left. You know these stalls, and you greet each of the horses like old friends, even though most of them are new ones.

You stop at one of the middle stalls on the right, clicking your tongue at an older horse. His coat is a deep coffee brown, dappled with white on his hindquarters.

“Dakota! Look at you, handsome.” You smile brightly. “Remember me?”

He blinks at you with those dark eyes, and he meanders a bit closer to the half door. You offer a loosely closed fist for him to inspect. When he does, you think it’s with some familiarity as he sniffs your hand all over. Or maybe he’s just smelling the apple pie glaze you licked off your finger earlier.

You laugh lightly and take a chance on petting the side of his neck. He lets you do it, a kind older statesman. Before you left, you had helped your dad break this horse in.

“He remembers you.”

You turn your head toward the door, flinching slightly in surprise. You didn’t even hear Dean come into the barn. His scuffed boots cross the distance leading him to you. Dark wash jeans and a black buttoned-down shirt are probably the extent of his cleaning up for the occasion, but the ensemble does suit him better than a proper suit would.

“It all looks the same,” you say quietly.

“That’s because it is,” Dean replies. His lips pull at a smirk as he points to the tool shed. “Like that dusty back room where we used to make out.”

You roll your eyes, but you can’t help the way your gaze draws to his calloused hands and long fingers. Your cheeks begin to prickle with warmth, but you refocus on his face, and unfortunately, that familiar grin. You’re sure that face has gotten him plenty of action since then.

“You do remember I have a fiancé,” you say.

Dean nods, holding up a placating hand. It slips into his pocket as he leans against a support beam. “Yeah, you never said where that guy was today.”

“Working,” you reply defensively. “We’re in the middle of a big project, and we can’t afford to drop the ball.”

“You two work together?”

“Yeah, for his father’s company.”

“Doing what?”

You hesitate. It seems like Sam hasn’t spoken to Dean yet about the offer either, but in this case, you’re grateful for it.

“Land development. His father is co-CEO and head of the Legal team. I help scope out properties and propose new projects,” you say.

Dean quirks a brow. “Land development, huh? Not what I would’ve imagined.”

His tone annoys you, making you slightly more tense, but you’ve already had this argument with Sam. You don’t have to explain yourself to this man.

“It’s not what I thought I’d end up in either, but if you think it’s hard to be a rancher, try being able to pay rent in California. We’re all just trying to survive, Dean,” you say.

At that, he actually nods more sincerely.

“Guess that’s fair. But it looks like you’re more than surviving now. You’ve got a friggin’ golf ball on your finger,” he says, gesturing at you, and more specifically your engagement ring.

You roll your eyes. “It’s not that big.”

The way he snorts earns a reluctant smile from you.

“How long you known the guy?” Dean asks.

You give him a shrewd look. He’s very curious about your personal life, but you can’t deny that you’ve been wondering what the past 12 years have made of him.

“About eight months,” you reply.

His brows raise almost as high as his hairline. “Eight months? When did he pop the question?”

“…A few weeks ago,” you say, albeit with some hesitation. “What?”

Dean shakes his head. “Nothing, I guess. Whirlwind romance.”

“And what about you?” you counter, fighting a blush. “No girlfriend?”

Dean chuckles. “Oh, I have plenty of friends. Just no time for the whirlwind.”

“I’m sure,” you say wryly. “Things really don’t change much around here.”

It’s a touch snider than you mean it to be. You don’t actually want to pick another fight. Frankly, you don’t have the emotional energy.

But even though Dean gives you a certain look, to your surprise, he doesn’t want to snipe anymore either. He just sighs.

“All right, come on. There’s some of Bobby’s stuff that you might want to look through,” he says, ushering you to follow him.

You do so reluctantly, over to the Foreman’s cabin.

The Foreman wrangles the other ranch hands, and he’s the Ranch Manager’s second-in-command. Bobby held that position for 23 years, starting from back when John was managing all operations himself. You used to live in this cabin with your mom and dad, back when they were together. 

Dean would later take your virginity when you turned 18—in the glorified closet that used to be your bedroom.

At least he doesn’t bring up that little anecdote as he leads you to the small, four-seater dining table. It has a few boxes stacked on top of it, probably what’s left of your father’s belongings. The rest has been cleared out except for a couch, an old wood coffee table, a TV on a stand, and some supplies in the kitchen. There are some signs of life here though, like a half-drunk beer on the coffee table, an empty box of pizza on the kitchen counter, and some crumpled napkins. Dean notices your observing gaze.

“I’ve been hanging out here the past few days. Cleaning the place up took a while, but uh, sometimes it’s nice to get away from the main house,” he says.

“I could see why. Thirty-two and still living with your daddy,” you teasingly remark.

Dean shoots you an amused brow raise, but he brings the first box to the living room coffee table and slides it toward you.

“Take whatever you want. He doesn’t have any other family, so I’m not sure what to do with the rest,” he says, rubbing a hand at the back of his neck.

Throwing it away feels wrong, or so his tone says. You nod in agreement and start looking through the box. The first thing you find is a large bottle of gold label scotch.

“Wow,” you say.

“That’s on brand,” Dean says, with a smirk. He eyes you. “We should probably crack it open, in Bobby’s honor, of course.”

Your lips tug at a smile. You hand it over, and Dean twists off the cap to take a swig. He offers it back to you, and you accept it dubiously after sitting beside him on the couch.

“You know we’re not teenagers anymore, right?” you say, but you still sip straight from the bottle just like he did, grimacing at the burn down your throat.

“We gotta lubricate this trip down memory lane somehow,” he replies. 

You snort in response and dig back into the box for something else.

Dean’s phone buzzes in his pocket. He checks and sees a text from Sam, asking if he’s with you.

Yeah, we’re going through Bobby’s stuff. I can come help. No need. It’s not that much. …Dude. What’re you doing? What? We’re good. Just catching up. All of a sudden you two are civil? I guess. It’s no big deal. We’ll be back in a few minutes. Ok. Just…be smart about this.

Dean frowns, resenting what his brother is insinuating. He glances up at you.

You haven’t noticed his silent conflict. You’re just looking through old baseball cards and faded trucker hats, rusty tools and piles of weathered flannel.

By the time you get to the third box, over an hour has passed, the bottle of scotch is almost empty, and you’re laughing harder and freer at the stories about Bobby that Dean’s pulling out easier than the next object. You haven’t even noticed that his knee rests against your thigh, or that you occasionally grab his forearm when something he says makes you particularly giggly.

It’s kind of cute that you still do that, but he keeps that thought locked in deep. His smile starts to hurt the corners of his cheeks, though.

Eventually, what you find at the bottom of the last box hits you so hard behind the ribs that it steals your breath. It’s a picture of you and your mom when you were around seven years old: your first year in this cabin, on this ranch.

To you it had seemed like a fun adventure, and so much cooler than your little boring apartment in Salida. Here, there were horses and cows and Sunday barbecues hosted by John Winchester himself.

It was on one of those Sundays that you met Dean, with all those freckles dotted across the bridge of his nose and cheeks, and the purest kind of happiness in his green eyes while he ate a slice of peach cobbler with a scoop of melting homemade ice cream. You remember him setting his own plate aside for a while though, just to comfort his six-year-old brother when his ice cream rolled off the side of his bowl into the dirt. Dean ended up slotting his own ice cream into Sammy’s bowl.

Bobby clocked what happened out of the corner of his eye. In the end, he was the one to slip you and Dean an extra scoop.

Your dad didn’t miss much, at least back then.

“I don’t get it, you know,” you say, somewhat shakily. “When we were kids, Dad was my safe place. Sure, he was gruff and curmudgeonly sometimes, but he was gentle too. He always looked out for me. I understand that shit didn’t work out between him and Mom, but I did try calling him. Years of five-minute conversations that never went anywhere, because he had to get back to the ranch.”

Your lips tremble and you try to blink past the sting, but the dam is already full to bursting, and your walls are failing all over again.

Dean watches you, and he actually listens as his heart grows heavier.

“I was a student. For a long time, I couldn’t afford to fly back to Salida,” you admit. “But he never once came out to visit. He didn’t even go to my college graduation. He showed up to Mom’s funeral. That’s it. I had to call the cemetery, the church, arrange the burial. I had to figure it all out by myself. And I get it, she left him. But he didn’t have to leave me too.”

You press your fingers over your mouth, as if that can stop the hurt from spilling out. You find sympathy in Dean’s eyes, but he doesn’t do what you expect. He rifles through the same collection of memories and pulls out a thin, white box.

Inside is a thin silver chain necklace with a small rose pendant. He lets the chain fall into your hand.

“He was going to give you this at your graduation,” Dean says. “I only know because he was hella fucking drunk one night, and he told me.” 

You laugh a little through unshed tears. You marvel at the necklace; it’s simple, dainty even, but beautiful. 

“Your mom told him not to go,” Dean says, earning your soft shock. “He hadn’t helped you pay for college, so in her mind, he didn’t have a right to see you. At least, that’s what he said happened.” 

“What?” you frown, rubbing the small pendant between your fingers. “I…can’t believe she said that.”

You had a partial scholarship and a work study job, but you wouldn’t have gotten through college without your mom. Living in San Diego hadn’t been easy at first, financially, and your mother was a nurse. You still don’t know how she managed it, but she always came through for you when it was time to pay for the next semester, and even for your textbooks.

You understood that even a Foreman didn’t make a hefty salary. It was part of the reason your mom gave you for leaving your dad. She didn’t come from a ranching family, and she had never wanted to spend her life on a ranch either, let alone one that your parents didn’t own.

In her words, “It’s hard to build a life on someone else’s land.”

She told you that she wanted more for you, and more for herself. Bobby hadn’t been willing to leave Winchester Ranch.

“He was dedicated to it. In some ways it was admirable, but in others…” she’d said, with an edge of bitterness.

You never really understood it. You realize now that you hadn’t tried hard enough. 

“I didn’t care about the fucking money or who paid for what. I just wanted him to be there,” you quietly confess. “But I know that’s a two-way street. I wasn’t there for him either.”

You look up at Dean, meeting his gaze.

“You were right,” you say, as emotion begins to choke you. “He had a goddamn heart attack, and I would’ve never known.”

Your shoulders shake as the first sob wracks through your body, but you soon find warmth and a familiar comfort in Dean’s arms.

“Okay, sweetheart. Come ‘ere,” he says, as he holds you close. There’s something different in his voice. Deep and a little coarse, but gentler. It’s the anchor you need right now, and you cling to it. You cling to him.

“It’s not your fault, okay? Seems like Bobby made his choices too,” Dean says. 

He tucks your head under his chin and briefly closes his eyes as he strokes your back. He feels every hiccup and unsteady breath in you, feels your tears dampening his shirt. His lips press to the crown of your head. Your fingers tangle in the green flannel at his back.

As you begin to relax after crying yourself out, your curled fingers smooth out into warm hands that release his shirt, but ultimately don’t move far, laid flat against his chest. He brushes frizzy strands of hair away from your face and behind your ear. You slowly look up to meet his eyes, with tears clinging to your lashes. Your lipstick is smudged, but you’re still a wonder to him.

It may just be the booze, but he remembers exactly how this used to feel. It cracks open something he’s been paving over, brick by brick. Year after year. He didn’t think this was what it would take to see you again.  

“Jesus,” he murmurs, brushing your cheek with his thumb. “You’re still so fucking beautiful. More, even.”

Your mouth parts with a hint of surprise, and a telling intake of breath. Your lashes lower as your gaze falls—to his lips.

What the hell is this?

You pull away from him, gently guiding his hand down.

He feels the sting of rejection, but also, his shame.

“’M sorry,” he says, looking away.

“…Yeah,” you say eloquently. You feel a prickle of guilt yourself as you wipe your cheeks.

You push yourself off the couch, but your body doesn’t cooperate well. Hard liquor hasn’t been your poison for a hot minute, whiskey least of all. Clearly, it’s remained a favorite of Dean’s.

But he’s far more than a memory you can shove to the back of your mind, especially when he gets up with you—to hold you and stop you from falling. He looks into your eyes, and the conflict in his makes you morbidly curious. What you would give to know what he’s thinking. 

“Just tell me one thing,” he says. “Does he treat you right?”

You frown. “Excuse me?”

His brows raise in challenge. “Come on. Work is work, but how’s he not gonna at least show up here for you?”

It probably makes him some kind of hypocrite, and he fights the voice inside that tells him he’s an idiot. An asshole.

But all you give him is the soft bite of your words.

“Not that it’s any of your business, but like I told you, our jobs are demanding,” you reply, crossing your arms. “He can be very considerate.”

Dean quirks a wry smile. He glances down at that ring, oval-shaped and vintage, putting it mildly. It would look real nice on his Great Aunt Matilda.

“Yeah, with this, huh?” he says, grasping your left hand. “Tell me this is some kind of kooky family heirloom.”

You slip your hand out of his. “He found it at an estate sale.”

“Oh, I believe you,” Dean chuckles. He taps the humble pendant that now has a place above your heart, after he helped you figure out how to put on the necklace it belongs to. “That’s more your speed.”

“How would you know?” you retort, batting his finger off. “It’s been all this time, and you think you still know me?”

You really do walk away from him now, beelining toward the door…

Well, you would have. You will. But his audacity truly is monumental, and after how he treated you this morning, this really is too much for you to wrap your head around. It derails what would’ve been a highly justified storm-out, and compels you back to face him in frustration.

“What’re you trying to do, Dean, spin my head around?” you snap. “You’re the one who broke my heart first. You don’t even know how much you messed me up.”

The confession escapes you before you can cram it back in, shocking you as well as him.

But it’s true.

Years. It had taken you years to get over him, your best friend. Your first real love.

Dean’s amusement faded the more you spoke.

“I know,” he says. And the admission costs him. Under the layers of bravado, bitterness and hurt, there’s the truth. “I was a stupid kid back then, who didn’t know how to let you go.”

You shake your head in denial. Your heart hurts, probably because it never healed right the first time.

“That’s bullshit,” you say. “You didn’t have to let me go. That was your choice.”

“Yeah, I did,” Dean says, with a newfound certainty that dims the light from his eyes. “You had a life ahead of you, sweetheart. Mine was always gonna be on this ranch.”

For a moment, you’re stunned where you stand.

Until reason and doubt start to compete for new ground in your mind.

He’s still making excuses, you think. He could’ve come with you to college. You told him that then, and even if his father tried to nail his boots to the ground, Dean never even called you once after you left. Where was this apology when it would’ve mattered?

“Jesus Christ, Dean…”

You rub your forehead at the headache you already feel coming on. You’re probably drunk, in fairness.

“Why are you telling me all this now?” you ask.

He sighs and rakes a hand through his hair, then rubs his eyes as well.

“Good question,” he chuckles slightly. He sobers when he meets your eyes again. “You told the truth today at the funeral. It’s only fair I give you the same courtesy.”

“Courtesy. Is that what this is?” you challenge.

“It’s an apology,” he says. “And uh, it’s goodbye, stranger, I guess.”

“Goodbye,” you echo. Though you’re unable to stop yourself from glancing down at his lips again. Then back to his eyes, despite the glassiness in yours. A hitch in your breath. “I guess it is.”

Dean sees it, another spark of your tears. He still hates it, both selfishly and unselfishly.

He can’t help but try to give you the stability you need. First, by his slow attempt to hold you, brushing his thumbs against your arms. Your mouth parts, but you don’t pull away.

He bows his head and follows the deep-seated need in his gut, urging him to press his lips to yours.

You breathe in sharply through your nose, but your fingers clench in his shirt again, near his collar. Your body melts willingly against his, like a muscle memory you thought you lost.

Then, the brush of his tongue short-circuits your brain. His hand moves down to the small of your back and presses you into him, eliciting tingles down your spine, and a blooming, pulsing heat between your legs.

You whimper into his mouth, and his hold tightens a fraction.

You pull back for a moment, panting for air. Your eyes meet his incredulously.

He steels himself, waiting for a slap, or at least a push.

You don’t have it in yourself to give him either one. Your heart clenches painfully, because despite the guilt and shame you already feel, something inside you, deeply vulnerable and frayed, needs this.

You tell yourself it’s just one more kiss.

He meets you halfway when you lean up to claim his lips. He claims you back, his hands once again molding to your waist, his arms caging you in, his hand sinking into your hair.

One more turns into him backing you up against the wall. You grab onto his shoulders for leverage, then his hair as his lips veer away from yours to blaze a hot, wet trail down your neck. Your moan is perfect in his ear, rattling down his spine and right to his cock.

You feel him heavy and thick through his jeans, pressing against you. His hand slips up your thigh, squeezing plush flesh as he goes. He bunches the skirt of your dress up to your hips.

“Unzip me,” you tell him, through hushed tones and heated breaths.

Dean nods, turning you around and brushing your hair out of the way so he can drag the zipper down in a slow, torturous tease. His eyes drink in every inch of your skin, but there’s nothing sexier to him than the way you brush down the sleeves and slip out of the dress the rest of the way. The fabric falls around your ankles, and you step out of them in your tall heels. Dean gets the full view of your lace panties, then the matching bra when you turn back around.

He catches your little intake of breath, like you’re guarding yourself before he sees you. He smiles and pulls you back in by your waist.

“Like I said, fucking beautiful,” he says, his gaze roaming your face.

Your lips tug at a smile as you meet his stare, but he finally renders you without a snappy word to say. He takes that win and revels in it as he kisses you.

You touch him more confidently than he remembers, dragging your nails down the back of his neck, sucking his tongue into your mouth, down to grabbing onto his belt and popping the buckle open. He follows your lead and helps you loosen his belt and jeans, but his boots and your heels are the first to form a haphazard pile on the way into the bigger bedroom, where his spare sheets and an old comforter line the bed.

He wasn’t lying to you when he said he’s been staying over here for the past few days. Not only so that he could clean up, but because he needed to clear his own head. Bobby’s death shook everyone, but it hit Dean in a way he hadn’t expected. He hasn’t told anyone this, but it was like losing a second father.

It reminded Dean of his regrets—his biggest one of all being you.

Despite how it looks, he knows it’s wrong to touch you. He knows it’s selfish to want you. But he hasn’t allowed himself to want anything in such a long time, and he thinks he might be able to right some old wrongs while he’s busy committing new ones.

After he lays you on the bed underneath him, Dean kisses his way along the column of your throat, down between your breasts. He slips a hand underneath you to unhook the pretty lace bra, and your back arches, giving him room. 

You really have grown up beautifully, even your boobs. Good for you, and good for him. Dean recommits them to memory as his tongue lavishes one of your nipples, while his right hand rolls the other between his thumb and forefinger. You sigh his name and slip your fingers through his hair, scratching his scalp with your nails. But your fingers hook on his flannel next.

“Take this off,” you breathe. “Want to see you too.”

Dean hesitates, but concedes to taking off his outer flannel. His undershirt stays on, even though you tug on it next. He aims to distract you by moving further down your body, laying open-mouthed kisses down your ribs and stomach, and over your mound, after he slips off your panties. He glances up between your legs and shoots you a mischievous grin.

“I used to love the way you tasted,” he says. “Those little sounds you made, the way you’d buck against my chin and scream my name… Let’s see if we can rock another sequel, huh, sweetheart?” 

“Dean,” you gasp, as his fingers slip between the folds of your pussy. They find slick arousal and heat.

“Jesus,” he murmurs. “You’re soaking wet.”

He bites his lower lip as his thumb searches, then finds your clit. Your hips start to writhe as you moan, grinding against his hand. He smirks in satisfaction before he lowers down. He moves your left thigh over his shoulder, and he feasts.

Your mouth falls open in a near silent cry, and your hips nearly come off the bed as you feel his tongue replace his fingers on your clit. Those long digits slip inside your hot channel. Hunger pools in your lower belly as your inner walls clench on him, desperately needing friction. Your breaths deepen as your free hand goes to your breast, toying with a hard nipple while you savor the sensations Dean’s giving you with his mouth and skilled fingers.

He curls his fingers and strokes you deeply, searching, exploring, until he finds that most sensitive place within your inner walls that has your body shuddering like an accordion. You grab a fistful of his hair as you buck hard against his mouth, a choked scream falling from your lips.

After withdrawing his fingers and wiping his mouth and nose, he presses a kiss into your inner thigh as you still tremble with the aftershocks of your orgasm.

He moves back up your body, and you take his face in your hands to kiss him deeply.

“What’s the verdict?” he teases afterward.

“You’ve gotten better,” you admit.

You sit up, intending to return the favor as your hands roam down his chest and underneath his shirt. He feels toned from long hours of hard labor and horse riding, but he stills your hands from grasping at the edge of his shirt. You’re confused, but he quickly guides you into turning over in the bed.

He kneels behind you as his steady hands continue to map every inch of your body. He caresses your sides, across your middle, and back up to your breasts while he kisses along your neck, then down your shoulder. There’s more calm confidence in his touch than he had at 20 years old, certainly more strength and more callouses, but it’s a delicious friction. And it’s a feeling that he absolutely has you enveloped in his arms, within his broad frame. You hang onto him on reflex.

Two of his fingers dip back into your pussy, circling your clit. You hang onto his arm as your body gives way to a moan. Arousal begins to pulse deep inside you again, but this time, you need his cock. You want to know if he’s improved there too. He seems to remember your body well enough.

“Dean…just fuck me,” you whisper coarsely. “Please…”

Before I lose my nerve.

“I gotcha, sweetheart,” he says, in a voice like old scotch and honey. Its depths make prickles of heat flash across your skin as fabric rustles. You assume he’s finally stripping off the rest of his clothes. You catch a glimpse over your shoulder of him tossing his shirt and boxers to the floor, but soon, the heat of his presence returns as he lines himself up at your entrance. His cock finally pushing inside you from behind makes your thighs tremble. Your nails dig into the mattress sheets.

“Dean,” you gasp. He stretches you so fucking good.

“You’ve got it, baby. Every damn inch, doing so good,” he says, breathing hard into your neck. His teeth graze your shoulder, making you shudder and push into him on reflex, sheathing him nice and snug inside. Already the walls of your cunt tremble around his cock.

Dean keeps his promise; it’s dewy skin against skin as holds you to him while he fucks you, slow, deep, and powerful, but never painful. Never too much.

He asks you what you want—faster or slower, rougher, or easier rhythm. You tell him you want him exactly how he is: fucking perfect.

And that night, it is fucking perfect.

Almost.

Both of you have left your cell phones on the kitchen table. They’ve buzzed almost half a dozen times, each with text messages and a handful of calls.

Your little black dress collects dust on the floor along with his jeans and flannel.

In the morning, long after he should, Dean wakes up nice and easy.

He just ends up waking alone.

AN: 🫣 Sorry loll. If you think those twists were fun, then get ready for a whole messy love triangle when Brady re-enters from Stage Left. 😬 (And are you curious about Dean and reader's past?)

Next Time:

What have I done?

Okay, you were drunk, but not that drunk.

You were in pain. Reckless. Selfish.

Shame invades your body and settles into your heart. All you can do is slowly, silently slip out of the bed without disturbing Dean. After reclaiming your clothes from the dusty floor and getting dressed, you hold back tears as you try to leave the tangle of desire and old memories, both beautiful and painful, behind you in that room. All you take with you is your phone and the silver necklace you already wear.

Although you wait to put on your heels until you get outside the cabin, that big stretch of hill up ahead to the main house is daunting.

“Mornin’.”

Your head turns sharply at the voice. You shouldn’t be surprised that someone’s already up this early, let alone one of the ranch hands. Benny. He’s tall and broad, like Dean, though with reddish brown hair and a thicker beard. He’s already dressed for the day in jeans and a long-sleeved shirt, drinking his coffee as he leans against the bunkhouse wall. You nod back at him with an awkward smile. 

“How you plan to get up the hill in those pumps?” he asks.

You sigh. “I don’t.”

You’re about to execute the worst walk of shame you’ve ever done, but at least it’s only for an audience of one. You slip off the heels and let the ankle straps dangle from your fingers as you walk barefoot on wet, dewy earth, all the way back up to the house. 

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I just knew the second these two went off alone (just like Sam pegged it), the kissing and all that comes after would start. Like they shouldn't have but...there's still history there and on a day like that, a parent's funeral, who does and doesn't show up reveals a lot about a person. They really are kindred spirits and surprisingly forgiving in some moments but there's so much history there too, too much shared pain.

Sam definitely clocked where this was going the second he saw Dean following her to the barn. There's just too much "unfinished business" here, and like you said, emotional tensions running high, alcohol, memories, grief, and the fact that Dean and reader have known each other basically their whole lives. Even with the 12 years in between, there's no erasing that history (of which you'll learn more about as we go along).

John's famous barbecue pit spins the mouthwatering smells of smoked meats. The tables are lined up and filled with buttery cornbread, potatoes done three different ways (mashed, roasted, and casseroled), salads, slaw, carrots and corn, wild rice, homemade dinner rolls and garlic bread, and no less than five different flavors of pie. You spy Dean tucking into his third slice of cherry. Evidently, it’s still his favorite. A piece of pastry crust flecks from his lower lip as he jumps in with an old story.

“So I’m maybe…twelve, thirteen. Bobby’s trying to show me how to fix this patch of barbed wire fence. Because I’m young and stupid, I get it in my head to jump over it while the wire’s slack,” Dean starts.

Sam and couple of the cowboys, Benny and Cas, are already smirking, chuckling a little, shaking their heads. They’ve definitely heard this one before, and this time, you have too. A smile curves your lips behind the rim of your glass of whiskey and Coke.

“I make it over, but my leg gets caught in the slack, and I just go down hard, eating the damn dirt,” Dean says. He mimes the impact of his body hitting the ground, complete with admittedly impressive sound effects. “But now the wire’s tight. Rips through my jeans, my ankle, blood soaking through. But, uh, Bobby calms me down, you know. He takes out his tool belt, and he says, ‘It’s all right, son. That’s why God made pliers, for idjits like you.’”

Laughter ripples across the table. Even John smiles, shaking his head.

“Well, he cleaned me up best he could and helped me back up on my horse,” Dean says. His grin is warm, and his gaze spans far beyond his beer. “Dad didn’t even have to lecture me. You remember what you said?”

John nods in amusement. “‘Your own body’s gonna do the punishing for me, son.’”

“Right. My ankle was busted for three weeks. Couldn’t ride, couldn’t do shit,” Dean says with a chuckle. “And it was summer too.”

At least he didn’t have to go to school, but for a boy like Dean, being cooped up in the house was three weeks of misery. All he could do was watch from his bedroom window while you and Sam ran off to ride your bikes in town or go swimming in the river.

He looks down toward the end of the table, wanting to see if you remember those days like he does. What he finds is your empty seat. His eyes run a search—and eventually catch you making your way over to the barn. His brows furrow in confusion, but as the conversation spins and Benny takes over the reminiscing, Dean gets up from the table, ignoring the little warning tug in his gut.

“Gonna get another beer,” he says.

But Sam’s perceptive gaze follows him. While you venture into the barn, Sam sees his brother’s projected path all too clearly.

The smell of horse makes you gag a little, but after you enter the barn and switch on the light, yet another wave of nostalgia blasts you in the face. You recognize that tack and tool shelf on the right-hand corner, and the rack of shotguns and rifles on the far left. You know these stalls, and you greet each of the horses like old friends, even though most of them are new ones.

You stop at one of the middle stalls on the right, clicking your tongue at an older horse. His coat is a deep coffee brown, dappled with white on his hindquarters.

“Dakota! Look at you, handsome.” You smile brightly. “Remember me?”

He blinks at you with those dark eyes, and he meanders a bit closer to the half door. You offer a loosely closed fist for him to inspect. When he does, you think it’s with some familiarity as he sniffs your hand all over. Or maybe he’s just smelling the apple pie glaze you licked off your finger earlier.

You laugh lightly and take a chance on petting the side of his neck. He lets you do it, a kind older statesman. Before you left, you had helped your dad break this horse in.

“He remembers you.”

You turn your head toward the door, flinching slightly in surprise. You didn’t even hear Dean come into the barn. His scuffed boots cross the distance leading him to you. Dark wash jeans and a black buttoned-down shirt are probably the extent of his cleaning up for the occasion, but the ensemble does suit him better than a proper suit would.

“It all looks the same,” you say quietly.

“That’s because it is,” Dean replies. His lips pull at a smirk as he points to the tool shed. “Like that dusty back room where we used to make out.”

You roll your eyes, but you can’t help the way your gaze draws to his calloused hands and long fingers. Your cheeks begin to prickle with warmth, but you refocus on his face, and unfortunately, that familiar grin. You’re sure that face has gotten him plenty of action since then.

“You do remember I have a fiancé,” you say.

Dean nods, holding up a placating hand. It slips into his pocket as he leans against a support beam. “Yeah, you never said where that guy was today.”

“Working,” you reply defensively. “We’re in the middle of a big project, and we can’t afford to drop the ball.”

“You two work together?”

“Yeah, for his father’s company.”

“Doing what?”

You hesitate. It seems like Sam hasn’t spoken to Dean yet about the offer either, but in this case, you’re grateful for it.

“Land development. His father is co-CEO and head of the Legal team. I help scope out properties and propose new projects,” you say.

Dean quirks a brow. “Land development, huh? Not what I would’ve imagined.”

His tone annoys you, making you slightly more tense, but you’ve already had this argument with Sam. You don’t have to explain yourself to this man.

“It’s not what I thought I’d end up in either, but if you think it’s hard to be a rancher, try being able to pay rent in California. We’re all just trying to survive, Dean,” you say.

At that, he actually nods more sincerely.

“Guess that’s fair. But it looks like you’re more than surviving now. You’ve got a friggin’ golf ball on your finger,” he says, gesturing at you, and more specifically your engagement ring.

You roll your eyes. “It’s not that big.”

The way he snorts earns a reluctant smile from you.

“How long you known the guy?” Dean asks.

You give him a shrewd look. He’s very curious about your personal life, but you can’t deny that you’ve been wondering what the past 12 years have made of him.

“About eight months,” you reply.

His brows raise almost as high as his hairline. “Eight months? When did he pop the question?”

“…A few weeks ago,” you say, albeit with some hesitation. “What?”

Dean shakes his head. “Nothing, I guess. Whirlwind romance.”

“And what about you?” you counter, fighting a blush. “No girlfriend?”

Dean chuckles. “Oh, I have plenty of friends. Just no time for the whirlwind.”

“I’m sure,” you say wryly. “Things really don’t change much around here.”

It’s a touch snider than you mean it to be. You don’t actually want to pick another fight. Frankly, you don’t have the emotional energy.

But even though Dean gives you a certain look, to your surprise, he doesn’t want to snipe anymore either. He just sighs.

“All right, come on. There’s some of Bobby’s stuff that you might want to look through,” he says, ushering you to follow him.

You do so reluctantly, over to the Foreman’s cabin.

The Foreman wrangles the other ranch hands, and he’s the Ranch Manager’s second-in-command. Bobby held that position for 23 years, starting from back when John was managing all operations himself. You used to live in this cabin with your mom and dad, back when they were together. 

Dean would later take your virginity when you turned 18—in the glorified closet that used to be your bedroom.

At least he doesn’t bring up that little anecdote as he leads you to the small, four-seater dining table. It has a few boxes stacked on top of it, probably what’s left of your father’s belongings. The rest has been cleared out except for a couch, an old wood coffee table, a TV on a stand, and some supplies in the kitchen. There are some signs of life here though, like a half-drunk beer on the coffee table, an empty box of pizza on the kitchen counter, and some crumpled napkins. Dean notices your observing gaze.

“I’ve been hanging out here the past few days. Cleaning the place up took a while, but uh, sometimes it’s nice to get away from the main house,” he says.

“I could see why. Thirty-two and still living with your daddy,” you teasingly remark.

Dean shoots you an amused brow raise, but he brings the first box to the living room coffee table and slides it toward you.

“Take whatever you want. He doesn’t have any other family, so I’m not sure what to do with the rest,” he says, rubbing a hand at the back of his neck.

Throwing it away feels wrong, or so his tone says. You nod in agreement and start looking through the box. The first thing you find is a large bottle of gold label scotch.

“Wow,” you say.

“That’s on brand,” Dean says, with a smirk. He eyes you. “We should probably crack it open, in Bobby’s honor, of course.”

Your lips tug at a smile. You hand it over, and Dean twists off the cap to take a swig. He offers it back to you, and you accept it dubiously after sitting beside him on the couch.

“You know we’re not teenagers anymore, right?” you say, but you still sip straight from the bottle just like he did, grimacing at the burn down your throat.

“We gotta lubricate this trip down memory lane somehow,” he replies. 

You snort in response and dig back into the box for something else.

Dean’s phone buzzes in his pocket. He checks and sees a text from Sam, asking if he’s with you.

Yeah, we’re going through Bobby’s stuff. I can come help. No need. It’s not that much. …Dude. What’re you doing? What? We’re good. Just catching up. All of a sudden you two are civil? I guess. It’s no big deal. We’ll be back in a few minutes. Ok. Just…be smart about this.

Dean frowns, resenting what his brother is insinuating. He glances up at you.

You haven’t noticed his silent conflict. You’re just looking through old baseball cards and faded trucker hats, rusty tools and piles of weathered flannel.

By the time you get to the third box, over an hour has passed, the bottle of scotch is almost empty, and you’re laughing harder and freer at the stories about Bobby that Dean’s pulling out easier than the next object. You haven’t even noticed that his knee rests against your thigh, or that you occasionally grab his forearm when something he says makes you particularly giggly.

It’s kind of cute that you still do that, but he keeps that thought locked in deep. His smile starts to hurt the corners of his cheeks, though.

Eventually, what you find at the bottom of the last box hits you so hard behind the ribs that it steals your breath. It’s a picture of you and your mom when you were around seven years old: your first year in this cabin, on this ranch.

To you it had seemed like a fun adventure, and so much cooler than your little boring apartment in Salida. Here, there were horses and cows and Sunday barbecues hosted by John Winchester himself.

It was on one of those Sundays that you met Dean, with all those freckles dotted across the bridge of his nose and cheeks, and the purest kind of happiness in his green eyes while he ate a slice of peach cobbler with a scoop of melting homemade ice cream. You remember him setting his own plate aside for a while though, just to comfort his six-year-old brother when his ice cream rolled off the side of his bowl into the dirt. Dean ended up slotting his own ice cream into Sammy’s bowl.

Bobby clocked what happened out of the corner of his eye. In the end, he was the one to slip you and Dean an extra scoop.

Your dad didn’t miss much, at least back then.

“I don’t get it, you know,” you say, somewhat shakily. “When we were kids, Dad was my safe place. Sure, he was gruff and curmudgeonly sometimes, but he was gentle too. He always looked out for me. I understand that shit didn’t work out between him and Mom, but I did try calling him. Years of five-minute conversations that never went anywhere, because he had to get back to the ranch.”

Your lips tremble and you try to blink past the sting, but the dam is already full to bursting, and your walls are failing all over again.

Dean watches you, and he actually listens as his heart grows heavier.

“I was a student. For a long time, I couldn’t afford to fly back to Salida,” you admit. “But he never once came out to visit. He didn’t even go to my college graduation. He showed up to Mom’s funeral. That’s it. I had to call the cemetery, the church, arrange the burial. I had to figure it all out by myself. And I get it, she left him. But he didn’t have to leave me too.”

You press your fingers over your mouth, as if that can stop the hurt from spilling out. You find sympathy in Dean’s eyes, but he doesn’t do what you expect. He rifles through the same collection of memories and pulls out a thin, white box.

Inside is a thin silver chain necklace with a small rose pendant. He lets the chain fall into your hand.

“He was going to give you this at your graduation,” Dean says. “I only know because he was hella fucking drunk one night, and he told me.” 

You laugh a little through unshed tears. You marvel at the necklace; it’s simple, dainty even, but beautiful. 

“Your mom told him not to go,” Dean says, earning your soft shock. “He hadn’t helped you pay for college, so in her mind, he didn’t have a right to see you. At least, that’s what he said happened.” 

“What?” you frown, rubbing the small pendant between your fingers. “I…can’t believe she said that.”

You had a partial scholarship and a work study job, but you wouldn’t have gotten through college without your mom. Living in San Diego hadn’t been easy at first, financially, and your mother was a nurse. You still don’t know how she managed it, but she always came through for you when it was time to pay for the next semester, and even for your textbooks.

You understood that even a Foreman didn’t make a hefty salary. It was part of the reason your mom gave you for leaving your dad. She didn’t come from a ranching family, and she had never wanted to spend her life on a ranch either, let alone one that your parents didn’t own.

In her words, “It’s hard to build a life on someone else’s land.”

She told you that she wanted more for you, and more for herself. Bobby hadn’t been willing to leave Winchester Ranch.

“He was dedicated to it. In some ways it was admirable, but in others…” she’d said, with an edge of bitterness.

You never really understood it. You realize now that you hadn’t tried hard enough. 

“I didn’t care about the fucking money or who paid for what. I just wanted him to be there,” you quietly confess. “But I know that’s a two-way street. I wasn’t there for him either.”

You look up at Dean, meeting his gaze.

“You were right,” you say, as emotion begins to choke you. “He had a goddamn heart attack, and I would’ve never known.”

Your shoulders shake as the first sob wracks through your body, but you soon find warmth and a familiar comfort in Dean’s arms.

“Okay, sweetheart. Come ‘ere,” he says, as he holds you close. There’s something different in his voice. Deep and a little coarse, but gentler. It’s the anchor you need right now, and you cling to it. You cling to him.

“It’s not your fault, okay? Seems like Bobby made his choices too,” Dean says. 

He tucks your head under his chin and briefly closes his eyes as he strokes your back. He feels every hiccup and unsteady breath in you, feels your tears dampening his shirt. His lips press to the crown of your head. Your fingers tangle in the green flannel at his back.

As you begin to relax after crying yourself out, your curled fingers smooth out into warm hands that release his shirt, but ultimately don’t move far, laid flat against his chest. He brushes frizzy strands of hair away from your face and behind your ear. You slowly look up to meet his eyes, with tears clinging to your lashes. Your lipstick is smudged, but you’re still a wonder to him.

It may just be the booze, but he remembers exactly how this used to feel. It cracks open something he’s been paving over, brick by brick. Year after year. He didn’t think this was what it would take to see you again.  

“Jesus,” he murmurs, brushing your cheek with his thumb. “You’re still so fucking beautiful. More, even.”

Your mouth parts with a hint of surprise, and a telling intake of breath. Your lashes lower as your gaze falls—to his lips.

What the hell is this?

You pull away from him, gently guiding his hand down.

He feels the sting of rejection, but also, his shame.

“’M sorry,” he says, looking away.

“…Yeah,” you say eloquently. You feel a prickle of guilt yourself as you wipe your cheeks.

You push yourself off the couch, but your body doesn’t cooperate well. Hard liquor hasn’t been your poison for a hot minute, whiskey least of all. Clearly, it’s remained a favorite of Dean’s.

But he’s far more than a memory you can shove to the back of your mind, especially when he gets up with you—to hold you and stop you from falling. He looks into your eyes, and the conflict in his makes you morbidly curious. What you would give to know what he’s thinking. 

“Just tell me one thing,” he says. “Does he treat you right?”

You frown. “Excuse me?”

His brows raise in challenge. “Come on. Work is work, but how’s he not gonna at least show up here for you?”

It probably makes him some kind of hypocrite, and he fights the voice inside that tells him he’s an idiot. An asshole.

But all you give him is the soft bite of your words.

“Not that it’s any of your business, but like I told you, our jobs are demanding,” you reply, crossing your arms. “He can be very considerate.”

Dean quirks a wry smile. He glances down at that ring, oval-shaped and vintage, putting it mildly. It would look real nice on his Great Aunt Matilda.

“Yeah, with this, huh?” he says, grasping your left hand. “Tell me this is some kind of kooky family heirloom.”

You slip your hand out of his. “He found it at an estate sale.”

“Oh, I believe you,” Dean chuckles. He taps the humble pendant that now has a place above your heart, after he helped you figure out how to put on the necklace it belongs to. “That’s more your speed.”

“How would you know?” you retort, batting his finger off. “It’s been all this time, and you think you still know me?”

You really do walk away from him now, beelining toward the door…

Well, you would have. You will. But his audacity truly is monumental, and after how he treated you this morning, this really is too much for you to wrap your head around. It derails what would’ve been a highly justified storm-out, and compels you back to face him in frustration.

“What’re you trying to do, Dean, spin my head around?” you snap. “You’re the one who broke my heart first. You don’t even know how much you messed me up.”

The confession escapes you before you can cram it back in, shocking you as well as him.

But it’s true.

Years. It had taken you years to get over him, your best friend. Your first real love.

Dean’s amusement faded the more you spoke.

“I know,” he says. And the admission costs him. Under the layers of bravado, bitterness and hurt, there’s the truth. “I was a stupid kid back then, who didn’t know how to let you go.”

You shake your head in denial. Your heart hurts, probably because it never healed right the first time.

“That’s bullshit,” you say. “You didn’t have to let me go. That was your choice.”

“Yeah, I did,” Dean says, with a newfound certainty that dims the light from his eyes. “You had a life ahead of you, sweetheart. Mine was always gonna be on this ranch.”

For a moment, you’re stunned where you stand.

Until reason and doubt start to compete for new ground in your mind.

He’s still making excuses, you think. He could’ve come with you to college. You told him that then, and even if his father tried to nail his boots to the ground, Dean never even called you once after you left. Where was this apology when it would’ve mattered?

“Jesus Christ, Dean…”

You rub your forehead at the headache you already feel coming on. You’re probably drunk, in fairness.

“Why are you telling me all this now?” you ask.

He sighs and rakes a hand through his hair, then rubs his eyes as well.

“Good question,” he chuckles slightly. He sobers when he meets your eyes again. “You told the truth today at the funeral. It’s only fair I give you the same courtesy.”

“Courtesy. Is that what this is?” you challenge.

“It’s an apology,” he says. “And uh, it’s goodbye, stranger, I guess.”

“Goodbye,” you echo. Though you’re unable to stop yourself from glancing down at his lips again. Then back to his eyes, despite the glassiness in yours. A hitch in your breath. “I guess it is.”

Dean sees it, another spark of your tears. He still hates it, both selfishly and unselfishly.

He can’t help but try to give you the stability you need. First, by his slow attempt to hold you, brushing his thumbs against your arms. Your mouth parts, but you don’t pull away.

He bows his head and follows the deep-seated need in his gut, urging him to press his lips to yours.

You breathe in sharply through your nose, but your fingers clench in his shirt again, near his collar. Your body melts willingly against his, like a muscle memory you thought you lost.

Then, the brush of his tongue short-circuits your brain. His hand moves down to the small of your back and presses you into him, eliciting tingles down your spine, and a blooming, pulsing heat between your legs.

You whimper into his mouth, and his hold tightens a fraction.

You pull back for a moment, panting for air. Your eyes meet his incredulously.

He steels himself, waiting for a slap, or at least a push.

You don’t have it in yourself to give him either one. Your heart clenches painfully, because despite the guilt and shame you already feel, something inside you, deeply vulnerable and frayed, needs this.

You tell yourself it’s just one more kiss.

He meets you halfway when you lean up to claim his lips. He claims you back, his hands once again molding to your waist, his arms caging you in, his hand sinking into your hair.

One more turns into him backing you up against the wall. You grab onto his shoulders for leverage, then his hair as his lips veer away from yours to blaze a hot, wet trail down your neck. Your moan is perfect in his ear, rattling down his spine and right to his cock.

You feel him heavy and thick through his jeans, pressing against you. His hand slips up your thigh, squeezing plush flesh as he goes. He bunches the skirt of your dress up to your hips.

“Unzip me,” you tell him, through hushed tones and heated breaths.

Dean nods, turning you around and brushing your hair out of the way so he can drag the zipper down in a slow, torturous tease. His eyes drink in every inch of your skin, but there’s nothing sexier to him than the way you brush down the sleeves and slip out of the dress the rest of the way. The fabric falls around your ankles, and you step out of them in your tall heels. Dean gets the full view of your lace panties, then the matching bra when you turn back around.

He catches your little intake of breath, like you’re guarding yourself before he sees you. He smiles and pulls you back in by your waist.

“Like I said, fucking beautiful,” he says, his gaze roaming your face.

Your lips tug at a smile as you meet his stare, but he finally renders you without a snappy word to say. He takes that win and revels in it as he kisses you.

You touch him more confidently than he remembers, dragging your nails down the back of his neck, sucking his tongue into your mouth, down to grabbing onto his belt and popping the buckle open. He follows your lead and helps you loosen his belt and jeans, but his boots and your heels are the first to form a haphazard pile on the way into the bigger bedroom, where his spare sheets and an old comforter line the bed.

He wasn’t lying to you when he said he’s been staying over here for the past few days. Not only so that he could clean up, but because he needed to clear his own head. Bobby’s death shook everyone, but it hit Dean in a way he hadn’t expected. He hasn’t told anyone this, but it was like losing a second father.

It reminded Dean of his regrets—his biggest one of all being you.

Despite how it looks, he knows it’s wrong to touch you. He knows it’s selfish to want you. But he hasn’t allowed himself to want anything in such a long time, and he thinks he might be able to right some old wrongs while he’s busy committing new ones.

After he lays you on the bed underneath him, Dean kisses his way along the column of your throat, down between your breasts. He slips a hand underneath you to unhook the pretty lace bra, and your back arches, giving him room. 

You really have grown up beautifully, even your boobs. Good for you, and good for him. Dean recommits them to memory as his tongue lavishes one of your nipples, while his right hand rolls the other between his thumb and forefinger. You sigh his name and slip your fingers through his hair, scratching his scalp with your nails. But your fingers hook on his flannel next.

“Take this off,” you breathe. “Want to see you too.”

Dean hesitates, but concedes to taking off his outer flannel. His undershirt stays on, even though you tug on it next. He aims to distract you by moving further down your body, laying open-mouthed kisses down your ribs and stomach, and over your mound, after he slips off your panties. He glances up between your legs and shoots you a mischievous grin.

“I used to love the way you tasted,” he says. “Those little sounds you made, the way you’d buck against my chin and scream my name… Let’s see if we can rock another sequel, huh, sweetheart?” 

“Dean,” you gasp, as his fingers slip between the folds of your pussy. They find slick arousal and heat.

“Jesus,” he murmurs. “You’re soaking wet.”

He bites his lower lip as his thumb searches, then finds your clit. Your hips start to writhe as you moan, grinding against his hand. He smirks in satisfaction before he lowers down. He moves your left thigh over his shoulder, and he feasts.

Your mouth falls open in a near silent cry, and your hips nearly come off the bed as you feel his tongue replace his fingers on your clit. Those long digits slip inside your hot channel. Hunger pools in your lower belly as your inner walls clench on him, desperately needing friction. Your breaths deepen as your free hand goes to your breast, toying with a hard nipple while you savor the sensations Dean’s giving you with his mouth and skilled fingers.

He curls his fingers and strokes you deeply, searching, exploring, until he finds that most sensitive place within your inner walls that has your body shuddering like an accordion. You grab a fistful of his hair as you buck hard against his mouth, a choked scream falling from your lips.

After withdrawing his fingers and wiping his mouth and nose, he presses a kiss into your inner thigh as you still tremble with the aftershocks of your orgasm.

He moves back up your body, and you take his face in your hands to kiss him deeply.

“What’s the verdict?” he teases afterward.

“You’ve gotten better,” you admit.

You sit up, intending to return the favor as your hands roam down his chest and underneath his shirt. He feels toned from long hours of hard labor and horse riding, but he stills your hands from grasping at the edge of his shirt. You’re confused, but he quickly guides you into turning over in the bed.

He kneels behind you as his steady hands continue to map every inch of your body. He caresses your sides, across your middle, and back up to your breasts while he kisses along your neck, then down your shoulder. There’s more calm confidence in his touch than he had at 20 years old, certainly more strength and more callouses, but it’s a delicious friction. And it’s a feeling that he absolutely has you enveloped in his arms, within his broad frame. You hang onto him on reflex.

Two of his fingers dip back into your pussy, circling your clit. You hang onto his arm as your body gives way to a moan. Arousal begins to pulse deep inside you again, but this time, you need his cock. You want to know if he’s improved there too. He seems to remember your body well enough.

“Dean…just fuck me,” you whisper coarsely. “Please…”

Before I lose my nerve.

“I gotcha, sweetheart,” he says, in a voice like old scotch and honey. Its depths make prickles of heat flash across your skin as fabric rustles. You assume he’s finally stripping off the rest of his clothes. You catch a glimpse over your shoulder of him tossing his shirt and boxers to the floor, but soon, the heat of his presence returns as he lines himself up at your entrance. His cock finally pushing inside you from behind makes your thighs tremble. Your nails dig into the mattress sheets.

“Dean,” you gasp. He stretches you so fucking good.

“You’ve got it, baby. Every damn inch, doing so good,” he says, breathing hard into your neck. His teeth graze your shoulder, making you shudder and push into him on reflex, sheathing him nice and snug inside. Already the walls of your cunt tremble around his cock.

Dean keeps his promise; it’s dewy skin against skin as holds you to him while he fucks you, slow, deep, and powerful, but never painful. Never too much.

He asks you what you want—faster or slower, rougher, or easier rhythm. You tell him you want him exactly how he is: fucking perfect.

And that night, it is fucking perfect.

Almost.

Both of you have left your cell phones on the kitchen table. They’ve buzzed almost half a dozen times, each with text messages and a handful of calls.

Your little black dress collects dust on the floor along with his jeans and flannel.

In the morning, long after he should, Dean wakes up nice and easy.

He just ends up waking alone.

AN: 🫣 Sorry loll. If you think those twists were fun, then get ready for a whole messy love triangle when Brady re-enters from Stage Left. 😬 (And are you curious about Dean and reader's past?)

Next Time:

What have I done?

Okay, you were drunk, but not that drunk.

You were in pain. Reckless. Selfish.

Shame invades your body and settles into your heart. All you can do is slowly, silently slip out of the bed without disturbing Dean. After reclaiming your clothes from the dusty floor and getting dressed, you hold back tears as you try to leave the tangle of desire and old memories, both beautiful and painful, behind you in that room. All you take with you is your phone and the silver necklace you already wear.

Although you wait to put on your heels until you get outside the cabin, that big stretch of hill up ahead to the main house is daunting.

“Mornin’.”

Your head turns sharply at the voice. You shouldn’t be surprised that someone’s already up this early, let alone one of the ranch hands. Benny. He’s tall and broad, like Dean, though with reddish brown hair and a thicker beard. He’s already dressed for the day in jeans and a long-sleeved shirt, drinking his coffee as he leans against the bunkhouse wall. You nod back at him with an awkward smile. 

“How you plan to get up the hill in those pumps?” he asks.

You sigh. “I don’t.”

You’re about to execute the worst walk of shame you’ve ever done, but at least it’s only for an audience of one. You slip off the heels and let the ankle straps dangle from your fingers as you walk barefoot on wet, dewy earth, all the way back up to the house. 

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John's famous barbecue pit spins the mouthwatering smells of smoked meats. The tables are lined up and filled with buttery cornbread, potatoes done three different ways (mashed, roasted, and casseroled), salads, slaw, carrots and corn, wild rice, homemade dinner rolls and garlic bread, and no less than five different flavors of pie. You spy Dean tucking into his third slice of cherry. Evidently, it’s still his favorite. A piece of pastry crust flecks from his lower lip as he jumps in with an old story.

“So I’m maybe…twelve, thirteen. Bobby’s trying to show me how to fix this patch of barbed wire fence. Because I’m young and stupid, I get it in my head to jump over it while the wire’s slack,” Dean starts.

Sam and couple of the cowboys, Benny and Cas, are already smirking, chuckling a little, shaking their heads. They’ve definitely heard this one before, and this time, you have too. A smile curves your lips behind the rim of your glass of whiskey and Coke.

“I make it over, but my leg gets caught in the slack, and I just go down hard, eating the damn dirt,” Dean says. He mimes the impact of his body hitting the ground, complete with admittedly impressive sound effects. “But now the wire’s tight. Rips through my jeans, my ankle, blood soaking through. But, uh, Bobby calms me down, you know. He takes out his tool belt, and he says, ‘It’s all right, son. That’s why God made pliers, for idjits like you.’”

Laughter ripples across the table. Even John smiles, shaking his head.

“Well, he cleaned me up best he could and helped me back up on my horse,” Dean says. His grin is warm, and his gaze spans far beyond his beer. “Dad didn’t even have to lecture me. You remember what you said?”

John nods in amusement. “‘Your own body’s gonna do the punishing for me, son.’”

“Right. My ankle was busted for three weeks. Couldn’t ride, couldn’t do shit,” Dean says with a chuckle. “And it was summer too.”

At least he didn’t have to go to school, but for a boy like Dean, being cooped up in the house was three weeks of misery. All he could do was watch from his bedroom window while you and Sam ran off to ride your bikes in town or go swimming in the river.

He looks down toward the end of the table, wanting to see if you remember those days like he does. What he finds is your empty seat. His eyes run a search—and eventually catch you making your way over to the barn. His brows furrow in confusion, but as the conversation spins and Benny takes over the reminiscing, Dean gets up from the table, ignoring the little warning tug in his gut.

“Gonna get another beer,” he says.

But Sam’s perceptive gaze follows him. While you venture into the barn, Sam sees his brother’s projected path all too clearly.

The smell of horse makes you gag a little, but after you enter the barn and switch on the light, yet another wave of nostalgia blasts you in the face. You recognize that tack and tool shelf on the right-hand corner, and the rack of shotguns and rifles on the far left. You know these stalls, and you greet each of the horses like old friends, even though most of them are new ones.

You stop at one of the middle stalls on the right, clicking your tongue at an older horse. His coat is a deep coffee brown, dappled with white on his hindquarters.

“Dakota! Look at you, handsome.” You smile brightly. “Remember me?”

He blinks at you with those dark eyes, and he meanders a bit closer to the half door. You offer a loosely closed fist for him to inspect. When he does, you think it’s with some familiarity as he sniffs your hand all over. Or maybe he’s just smelling the apple pie glaze you licked off your finger earlier.

You laugh lightly and take a chance on petting the side of his neck. He lets you do it, a kind older statesman. Before you left, you had helped your dad break this horse in.

“He remembers you.”

You turn your head toward the door, flinching slightly in surprise. You didn’t even hear Dean come into the barn. His scuffed boots cross the distance leading him to you. Dark wash jeans and a black buttoned-down shirt are probably the extent of his cleaning up for the occasion, but the ensemble does suit him better than a proper suit would.

“It all looks the same,” you say quietly.

“That’s because it is,” Dean replies. His lips pull at a smirk as he points to the tool shed. “Like that dusty back room where we used to make out.”

You roll your eyes, but you can’t help the way your gaze draws to his calloused hands and long fingers. Your cheeks begin to prickle with warmth, but you refocus on his face, and unfortunately, that familiar grin. You’re sure that face has gotten him plenty of action since then.

“You do remember I have a fiancé,” you say.

Dean nods, holding up a placating hand. It slips into his pocket as he leans against a support beam. “Yeah, you never said where that guy was today.”

“Working,” you reply defensively. “We’re in the middle of a big project, and we can’t afford to drop the ball.”

“You two work together?”

“Yeah, for his father’s company.”

“Doing what?”

You hesitate. It seems like Sam hasn’t spoken to Dean yet about the offer either, but in this case, you’re grateful for it.

“Land development. His father is co-CEO and head of the Legal team. I help scope out properties and propose new projects,” you say.

Dean quirks a brow. “Land development, huh? Not what I would’ve imagined.”

His tone annoys you, making you slightly more tense, but you’ve already had this argument with Sam. You don’t have to explain yourself to this man.

“It’s not what I thought I’d end up in either, but if you think it’s hard to be a rancher, try being able to pay rent in California. We’re all just trying to survive, Dean,” you say.

At that, he actually nods more sincerely.

“Guess that’s fair. But it looks like you’re more than surviving now. You’ve got a friggin’ golf ball on your finger,” he says, gesturing at you, and more specifically your engagement ring.

You roll your eyes. “It’s not that big.”

The way he snorts earns a reluctant smile from you.

“How long you known the guy?” Dean asks.

You give him a shrewd look. He’s very curious about your personal life, but you can’t deny that you’ve been wondering what the past 12 years have made of him.

“About eight months,” you reply.

His brows raise almost as high as his hairline. “Eight months? When did he pop the question?”

“…A few weeks ago,” you say, albeit with some hesitation. “What?”

Dean shakes his head. “Nothing, I guess. Whirlwind romance.”

“And what about you?” you counter, fighting a blush. “No girlfriend?”

Dean chuckles. “Oh, I have plenty of friends. Just no time for the whirlwind.”

“I’m sure,” you say wryly. “Things really don’t change much around here.”

It’s a touch snider than you mean it to be. You don’t actually want to pick another fight. Frankly, you don’t have the emotional energy.

But even though Dean gives you a certain look, to your surprise, he doesn’t want to snipe anymore either. He just sighs.

“All right, come on. There’s some of Bobby’s stuff that you might want to look through,” he says, ushering you to follow him.

You do so reluctantly, over to the Foreman’s cabin.

The Foreman wrangles the other ranch hands, and he’s the Ranch Manager’s second-in-command. Bobby held that position for 23 years, starting from back when John was managing all operations himself. You used to live in this cabin with your mom and dad, back when they were together. 

Dean would later take your virginity when you turned 18—in the glorified closet that used to be your bedroom.

At least he doesn’t bring up that little anecdote as he leads you to the small, four-seater dining table. It has a few boxes stacked on top of it, probably what’s left of your father’s belongings. The rest has been cleared out except for a couch, an old wood coffee table, a TV on a stand, and some supplies in the kitchen. There are some signs of life here though, like a half-drunk beer on the coffee table, an empty box of pizza on the kitchen counter, and some crumpled napkins. Dean notices your observing gaze.

“I’ve been hanging out here the past few days. Cleaning the place up took a while, but uh, sometimes it’s nice to get away from the main house,” he says.

“I could see why. Thirty-two and still living with your daddy,” you teasingly remark.

Dean shoots you an amused brow raise, but he brings the first box to the living room coffee table and slides it toward you.

“Take whatever you want. He doesn’t have any other family, so I’m not sure what to do with the rest,” he says, rubbing a hand at the back of his neck.

Throwing it away feels wrong, or so his tone says. You nod in agreement and start looking through the box. The first thing you find is a large bottle of gold label scotch.

“Wow,” you say.

“That’s on brand,” Dean says, with a smirk. He eyes you. “We should probably crack it open, in Bobby’s honor, of course.”

Your lips tug at a smile. You hand it over, and Dean twists off the cap to take a swig. He offers it back to you, and you accept it dubiously after sitting beside him on the couch.

“You know we’re not teenagers anymore, right?” you say, but you still sip straight from the bottle just like he did, grimacing at the burn down your throat.

“We gotta lubricate this trip down memory lane somehow,” he replies. 

You snort in response and dig back into the box for something else.

Dean’s phone buzzes in his pocket. He checks and sees a text from Sam, asking if he’s with you.

Yeah, we’re going through Bobby’s stuff. I can come help. No need. It’s not that much. …Dude. What’re you doing? What? We’re good. Just catching up. All of a sudden you two are civil? I guess. It’s no big deal. We’ll be back in a few minutes. Ok. Just…be smart about this.

Dean frowns, resenting what his brother is insinuating. He glances up at you.

You haven’t noticed his silent conflict. You’re just looking through old baseball cards and faded trucker hats, rusty tools and piles of weathered flannel.

By the time you get to the third box, over an hour has passed, the bottle of scotch is almost empty, and you’re laughing harder and freer at the stories about Bobby that Dean’s pulling out easier than the next object. You haven’t even noticed that his knee rests against your thigh, or that you occasionally grab his forearm when something he says makes you particularly giggly.

It’s kind of cute that you still do that, but he keeps that thought locked in deep. His smile starts to hurt the corners of his cheeks, though.

Eventually, what you find at the bottom of the last box hits you so hard behind the ribs that it steals your breath. It’s a picture of you and your mom when you were around seven years old: your first year in this cabin, on this ranch.

To you it had seemed like a fun adventure, and so much cooler than your little boring apartment in Salida. Here, there were horses and cows and Sunday barbecues hosted by John Winchester himself.

It was on one of those Sundays that you met Dean, with all those freckles dotted across the bridge of his nose and cheeks, and the purest kind of happiness in his green eyes while he ate a slice of peach cobbler with a scoop of melting homemade ice cream. You remember him setting his own plate aside for a while though, just to comfort his six-year-old brother when his ice cream rolled off the side of his bowl into the dirt. Dean ended up slotting his own ice cream into Sammy’s bowl.

Bobby clocked what happened out of the corner of his eye. In the end, he was the one to slip you and Dean an extra scoop.

Your dad didn’t miss much, at least back then.

“I don’t get it, you know,” you say, somewhat shakily. “When we were kids, Dad was my safe place. Sure, he was gruff and curmudgeonly sometimes, but he was gentle too. He always looked out for me. I understand that shit didn’t work out between him and Mom, but I did try calling him. Years of five-minute conversations that never went anywhere, because he had to get back to the ranch.”

Your lips tremble and you try to blink past the sting, but the dam is already full to bursting, and your walls are failing all over again.

Dean watches you, and he actually listens as his heart grows heavier.

“I was a student. For a long time, I couldn’t afford to fly back to Salida,” you admit. “But he never once came out to visit. He didn’t even go to my college graduation. He showed up to Mom’s funeral. That’s it. I had to call the cemetery, the church, arrange the burial. I had to figure it all out by myself. And I get it, she left him. But he didn’t have to leave me too.”

You press your fingers over your mouth, as if that can stop the hurt from spilling out. You find sympathy in Dean’s eyes, but he doesn’t do what you expect. He rifles through the same collection of memories and pulls out a thin, white box.

Inside is a thin silver chain necklace with a small rose pendant. He lets the chain fall into your hand.

“He was going to give you this at your graduation,” Dean says. “I only know because he was hella fucking drunk one night, and he told me.” 

You laugh a little through unshed tears. You marvel at the necklace; it’s simple, dainty even, but beautiful. 

“Your mom told him not to go,” Dean says, earning your soft shock. “He hadn’t helped you pay for college, so in her mind, he didn’t have a right to see you. At least, that’s what he said happened.” 

“What?” you frown, rubbing the small pendant between your fingers. “I…can’t believe she said that.”

You had a partial scholarship and a work study job, but you wouldn’t have gotten through college without your mom. Living in San Diego hadn’t been easy at first, financially, and your mother was a nurse. You still don’t know how she managed it, but she always came through for you when it was time to pay for the next semester, and even for your textbooks.

You understood that even a Foreman didn’t make a hefty salary. It was part of the reason your mom gave you for leaving your dad. She didn’t come from a ranching family, and she had never wanted to spend her life on a ranch either, let alone one that your parents didn’t own.

In her words, “It’s hard to build a life on someone else’s land.”

She told you that she wanted more for you, and more for herself. Bobby hadn’t been willing to leave Winchester Ranch.

“He was dedicated to it. In some ways it was admirable, but in others…” she’d said, with an edge of bitterness.

You never really understood it. You realize now that you hadn’t tried hard enough. 

“I didn’t care about the fucking money or who paid for what. I just wanted him to be there,” you quietly confess. “But I know that’s a two-way street. I wasn’t there for him either.”

You look up at Dean, meeting his gaze.

“You were right,” you say, as emotion begins to choke you. “He had a goddamn heart attack, and I would’ve never known.”

Your shoulders shake as the first sob wracks through your body, but you soon find warmth and a familiar comfort in Dean’s arms.

“Okay, sweetheart. Come ‘ere,” he says, as he holds you close. There’s something different in his voice. Deep and a little coarse, but gentler. It’s the anchor you need right now, and you cling to it. You cling to him.

“It’s not your fault, okay? Seems like Bobby made his choices too,” Dean says. 

He tucks your head under his chin and briefly closes his eyes as he strokes your back. He feels every hiccup and unsteady breath in you, feels your tears dampening his shirt. His lips press to the crown of your head. Your fingers tangle in the green flannel at his back.

As you begin to relax after crying yourself out, your curled fingers smooth out into warm hands that release his shirt, but ultimately don’t move far, laid flat against his chest. He brushes frizzy strands of hair away from your face and behind your ear. You slowly look up to meet his eyes, with tears clinging to your lashes. Your lipstick is smudged, but you’re still a wonder to him.

It may just be the booze, but he remembers exactly how this used to feel. It cracks open something he’s been paving over, brick by brick. Year after year. He didn’t think this was what it would take to see you again.  

“Jesus,” he murmurs, brushing your cheek with his thumb. “You’re still so fucking beautiful. More, even.”

Your mouth parts with a hint of surprise, and a telling intake of breath. Your lashes lower as your gaze falls—to his lips.

What the hell is this?

You pull away from him, gently guiding his hand down.

He feels the sting of rejection, but also, his shame.

“’M sorry,” he says, looking away.

“…Yeah,” you say eloquently. You feel a prickle of guilt yourself as you wipe your cheeks.

You push yourself off the couch, but your body doesn’t cooperate well. Hard liquor hasn’t been your poison for a hot minute, whiskey least of all. Clearly, it’s remained a favorite of Dean’s.

But he’s far more than a memory you can shove to the back of your mind, especially when he gets up with you—to hold you and stop you from falling. He looks into your eyes, and the conflict in his makes you morbidly curious. What you would give to know what he’s thinking. 

“Just tell me one thing,” he says. “Does he treat you right?”

You frown. “Excuse me?”

His brows raise in challenge. “Come on. Work is work, but how’s he not gonna at least show up here for you?”

It probably makes him some kind of hypocrite, and he fights the voice inside that tells him he’s an idiot. An asshole.

But all you give him is the soft bite of your words.

“Not that it’s any of your business, but like I told you, our jobs are demanding,” you reply, crossing your arms. “He can be very considerate.”

Dean quirks a wry smile. He glances down at that ring, oval-shaped and vintage, putting it mildly. It would look real nice on his Great Aunt Matilda.

“Yeah, with this, huh?” he says, grasping your left hand. “Tell me this is some kind of kooky family heirloom.”

You slip your hand out of his. “He found it at an estate sale.”

“Oh, I believe you,” Dean chuckles. He taps the humble pendant that now has a place above your heart, after he helped you figure out how to put on the necklace it belongs to. “That’s more your speed.”

“How would you know?” you retort, batting his finger off. “It’s been all this time, and you think you still know me?”

You really do walk away from him now, beelining toward the door…

Well, you would have. You will. But his audacity truly is monumental, and after how he treated you this morning, this really is too much for you to wrap your head around. It derails what would’ve been a highly justified storm-out, and compels you back to face him in frustration.

“What’re you trying to do, Dean, spin my head around?” you snap. “You’re the one who broke my heart first. You don’t even know how much you messed me up.”

The confession escapes you before you can cram it back in, shocking you as well as him.

But it’s true.

Years. It had taken you years to get over him, your best friend. Your first real love.

Dean’s amusement faded the more you spoke.

“I know,” he says. And the admission costs him. Under the layers of bravado, bitterness and hurt, there’s the truth. “I was a stupid kid back then, who didn’t know how to let you go.”

You shake your head in denial. Your heart hurts, probably because it never healed right the first time.

“That’s bullshit,” you say. “You didn’t have to let me go. That was your choice.”

“Yeah, I did,” Dean says, with a newfound certainty that dims the light from his eyes. “You had a life ahead of you, sweetheart. Mine was always gonna be on this ranch.”

For a moment, you’re stunned where you stand.

Until reason and doubt start to compete for new ground in your mind.

He’s still making excuses, you think. He could’ve come with you to college. You told him that then, and even if his father tried to nail his boots to the ground, Dean never even called you once after you left. Where was this apology when it would’ve mattered?

“Jesus Christ, Dean…”

You rub your forehead at the headache you already feel coming on. You’re probably drunk, in fairness.

“Why are you telling me all this now?” you ask.

He sighs and rakes a hand through his hair, then rubs his eyes as well.

“Good question,” he chuckles slightly. He sobers when he meets your eyes again. “You told the truth today at the funeral. It’s only fair I give you the same courtesy.”

“Courtesy. Is that what this is?” you challenge.

“It’s an apology,” he says. “And uh, it’s goodbye, stranger, I guess.”

“Goodbye,” you echo. Though you’re unable to stop yourself from glancing down at his lips again. Then back to his eyes, despite the glassiness in yours. A hitch in your breath. “I guess it is.”

Dean sees it, another spark of your tears. He still hates it, both selfishly and unselfishly.

He can’t help but try to give you the stability you need. First, by his slow attempt to hold you, brushing his thumbs against your arms. Your mouth parts, but you don’t pull away.

He bows his head and follows the deep-seated need in his gut, urging him to press his lips to yours.

You breathe in sharply through your nose, but your fingers clench in his shirt again, near his collar. Your body melts willingly against his, like a muscle memory you thought you lost.

Then, the brush of his tongue short-circuits your brain. His hand moves down to the small of your back and presses you into him, eliciting tingles down your spine, and a blooming, pulsing heat between your legs.

You whimper into his mouth, and his hold tightens a fraction.

You pull back for a moment, panting for air. Your eyes meet his incredulously.

He steels himself, waiting for a slap, or at least a push.

You don’t have it in yourself to give him either one. Your heart clenches painfully, because despite the guilt and shame you already feel, something inside you, deeply vulnerable and frayed, needs this.

You tell yourself it’s just one more kiss.

He meets you halfway when you lean up to claim his lips. He claims you back, his hands once again molding to your waist, his arms caging you in, his hand sinking into your hair.

One more turns into him backing you up against the wall. You grab onto his shoulders for leverage, then his hair as his lips veer away from yours to blaze a hot, wet trail down your neck. Your moan is perfect in his ear, rattling down his spine and right to his cock.

You feel him heavy and thick through his jeans, pressing against you. His hand slips up your thigh, squeezing plush flesh as he goes. He bunches the skirt of your dress up to your hips.

“Unzip me,” you tell him, through hushed tones and heated breaths.

Dean nods, turning you around and brushing your hair out of the way so he can drag the zipper down in a slow, torturous tease. His eyes drink in every inch of your skin, but there’s nothing sexier to him than the way you brush down the sleeves and slip out of the dress the rest of the way. The fabric falls around your ankles, and you step out of them in your tall heels. Dean gets the full view of your lace panties, then the matching bra when you turn back around.

He catches your little intake of breath, like you’re guarding yourself before he sees you. He smiles and pulls you back in by your waist.

“Like I said, fucking beautiful,” he says, his gaze roaming your face.

Your lips tug at a smile as you meet his stare, but he finally renders you without a snappy word to say. He takes that win and revels in it as he kisses you.

You touch him more confidently than he remembers, dragging your nails down the back of his neck, sucking his tongue into your mouth, down to grabbing onto his belt and popping the buckle open. He follows your lead and helps you loosen his belt and jeans, but his boots and your heels are the first to form a haphazard pile on the way into the bigger bedroom, where his spare sheets and an old comforter line the bed.

He wasn’t lying to you when he said he’s been staying over here for the past few days. Not only so that he could clean up, but because he needed to clear his own head. Bobby’s death shook everyone, but it hit Dean in a way he hadn’t expected. He hasn’t told anyone this, but it was like losing a second father.

It reminded Dean of his regrets—his biggest one of all being you.

Despite how it looks, he knows it’s wrong to touch you. He knows it’s selfish to want you. But he hasn’t allowed himself to want anything in such a long time, and he thinks he might be able to right some old wrongs while he’s busy committing new ones.

After he lays you on the bed underneath him, Dean kisses his way along the column of your throat, down between your breasts. He slips a hand underneath you to unhook the pretty lace bra, and your back arches, giving him room. 

You really have grown up beautifully, even your boobs. Good for you, and good for him. Dean recommits them to memory as his tongue lavishes one of your nipples, while his right hand rolls the other between his thumb and forefinger. You sigh his name and slip your fingers through his hair, scratching his scalp with your nails. But your fingers hook on his flannel next.

“Take this off,” you breathe. “Want to see you too.”

Dean hesitates, but concedes to taking off his outer flannel. His undershirt stays on, even though you tug on it next. He aims to distract you by moving further down your body, laying open-mouthed kisses down your ribs and stomach, and over your mound, after he slips off your panties. He glances up between your legs and shoots you a mischievous grin.

“I used to love the way you tasted,” he says. “Those little sounds you made, the way you’d buck against my chin and scream my name… Let’s see if we can rock another sequel, huh, sweetheart?” 

“Dean,” you gasp, as his fingers slip between the folds of your pussy. They find slick arousal and heat.

“Jesus,” he murmurs. “You’re soaking wet.”

He bites his lower lip as his thumb searches, then finds your clit. Your hips start to writhe as you moan, grinding against his hand. He smirks in satisfaction before he lowers down. He moves your left thigh over his shoulder, and he feasts.

Your mouth falls open in a near silent cry, and your hips nearly come off the bed as you feel his tongue replace his fingers on your clit. Those long digits slip inside your hot channel. Hunger pools in your lower belly as your inner walls clench on him, desperately needing friction. Your breaths deepen as your free hand goes to your breast, toying with a hard nipple while you savor the sensations Dean’s giving you with his mouth and skilled fingers.

He curls his fingers and strokes you deeply, searching, exploring, until he finds that most sensitive place within your inner walls that has your body shuddering like an accordion. You grab a fistful of his hair as you buck hard against his mouth, a choked scream falling from your lips.

After withdrawing his fingers and wiping his mouth and nose, he presses a kiss into your inner thigh as you still tremble with the aftershocks of your orgasm.

He moves back up your body, and you take his face in your hands to kiss him deeply.

“What’s the verdict?” he teases afterward.

“You’ve gotten better,” you admit.

You sit up, intending to return the favor as your hands roam down his chest and underneath his shirt. He feels toned from long hours of hard labor and horse riding, but he stills your hands from grasping at the edge of his shirt. You’re confused, but he quickly guides you into turning over in the bed.

He kneels behind you as his steady hands continue to map every inch of your body. He caresses your sides, across your middle, and back up to your breasts while he kisses along your neck, then down your shoulder. There’s more calm confidence in his touch than he had at 20 years old, certainly more strength and more callouses, but it’s a delicious friction. And it’s a feeling that he absolutely has you enveloped in his arms, within his broad frame. You hang onto him on reflex.

Two of his fingers dip back into your pussy, circling your clit. You hang onto his arm as your body gives way to a moan. Arousal begins to pulse deep inside you again, but this time, you need his cock. You want to know if he’s improved there too. He seems to remember your body well enough.

“Dean…just fuck me,” you whisper coarsely. “Please…”

Before I lose my nerve.

“I gotcha, sweetheart,” he says, in a voice like old scotch and honey. Its depths make prickles of heat flash across your skin as fabric rustles. You assume he’s finally stripping off the rest of his clothes. You catch a glimpse over your shoulder of him tossing his shirt and boxers to the floor, but soon, the heat of his presence returns as he lines himself up at your entrance. His cock finally pushing inside you from behind makes your thighs tremble. Your nails dig into the mattress sheets.

“Dean,” you gasp. He stretches you so fucking good.

“You’ve got it, baby. Every damn inch, doing so good,” he says, breathing hard into your neck. His teeth graze your shoulder, making you shudder and push into him on reflex, sheathing him nice and snug inside. Already the walls of your cunt tremble around his cock.

Dean keeps his promise; it’s dewy skin against skin as holds you to him while he fucks you, slow, deep, and powerful, but never painful. Never too much.

He asks you what you want—faster or slower, rougher, or easier rhythm. You tell him you want him exactly how he is: fucking perfect.

And that night, it is fucking perfect.

Almost.

Both of you have left your cell phones on the kitchen table. They’ve buzzed almost half a dozen times, each with text messages and a handful of calls.

Your little black dress collects dust on the floor along with his jeans and flannel.

In the morning, long after he should, Dean wakes up nice and easy.

He just ends up waking alone.

AN: 🫣 Sorry loll. If you think those twists were fun, then get ready for a whole messy love triangle when Brady re-enters from Stage Left. 😬 (And are you curious about Dean and reader's past?)

Next Time:

What have I done?

Okay, you were drunk, but not that drunk.

You were in pain. Reckless. Selfish.

Shame invades your body and settles into your heart. All you can do is slowly, silently slip out of the bed without disturbing Dean. After reclaiming your clothes from the dusty floor and getting dressed, you hold back tears as you try to leave the tangle of desire and old memories, both beautiful and painful, behind you in that room. All you take with you is your phone and the silver necklace you already wear.

Although you wait to put on your heels until you get outside the cabin, that big stretch of hill up ahead to the main house is daunting.

“Mornin’.”

Your head turns sharply at the voice. You shouldn’t be surprised that someone’s already up this early, let alone one of the ranch hands. Benny. He’s tall and broad, like Dean, though with reddish brown hair and a thicker beard. He’s already dressed for the day in jeans and a long-sleeved shirt, drinking his coffee as he leans against the bunkhouse wall. You nod back at him with an awkward smile. 

“How you plan to get up the hill in those pumps?” he asks.

You sigh. “I don’t.”

You’re about to execute the worst walk of shame you’ve ever done, but at least it’s only for an audience of one. You slip off the heels and let the ankle straps dangle from your fingers as you walk barefoot on wet, dewy earth, all the way back up to the house. 

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John's famous barbecue pit spins the mouthwatering smells of smoked meats. The tables are lined up and filled with buttery cornbread, potatoes done three different ways (mashed, roasted, and casseroled), salads, slaw, carrots and corn, wild rice, homemade dinner rolls and garlic bread, and no less than five different flavors of pie. You spy Dean tucking into his third slice of cherry. Evidently, it’s still his favorite. A piece of pastry crust flecks from his lower lip as he jumps in with an old story.

“So I’m maybe…twelve, thirteen. Bobby’s trying to show me how to fix this patch of barbed wire fence. Because I’m young and stupid, I get it in my head to jump over it while the wire’s slack,” Dean starts.

Sam and couple of the cowboys, Benny and Cas, are already smirking, chuckling a little, shaking their heads. They’ve definitely heard this one before, and this time, you have too. A smile curves your lips behind the rim of your glass of whiskey and Coke.

“I make it over, but my leg gets caught in the slack, and I just go down hard, eating the damn dirt,” Dean says. He mimes the impact of his body hitting the ground, complete with admittedly impressive sound effects. “But now the wire’s tight. Rips through my jeans, my ankle, blood soaking through. But, uh, Bobby calms me down, you know. He takes out his tool belt, and he says, ‘It’s all right, son. That’s why God made pliers, for idjits like you.’”

Laughter ripples across the table. Even John smiles, shaking his head.

“Well, he cleaned me up best he could and helped me back up on my horse,” Dean says. His grin is warm, and his gaze spans far beyond his beer. “Dad didn’t even have to lecture me. You remember what you said?”

John nods in amusement. “‘Your own body’s gonna do the punishing for me, son.’”

“Right. My ankle was busted for three weeks. Couldn’t ride, couldn’t do shit,” Dean says with a chuckle. “And it was summer too.”

At least he didn’t have to go to school, but for a boy like Dean, being cooped up in the house was three weeks of misery. All he could do was watch from his bedroom window while you and Sam ran off to ride your bikes in town or go swimming in the river.

He looks down toward the end of the table, wanting to see if you remember those days like he does. What he finds is your empty seat. His eyes run a search—and eventually catch you making your way over to the barn. His brows furrow in confusion, but as the conversation spins and Benny takes over the reminiscing, Dean gets up from the table, ignoring the little warning tug in his gut.

“Gonna get another beer,” he says.

But Sam’s perceptive gaze follows him. While you venture into the barn, Sam sees his brother’s projected path all too clearly.

The smell of horse makes you gag a little, but after you enter the barn and switch on the light, yet another wave of nostalgia blasts you in the face. You recognize that tack and tool shelf on the right-hand corner, and the rack of shotguns and rifles on the far left. You know these stalls, and you greet each of the horses like old friends, even though most of them are new ones.

You stop at one of the middle stalls on the right, clicking your tongue at an older horse. His coat is a deep coffee brown, dappled with white on his hindquarters.

“Dakota! Look at you, handsome.” You smile brightly. “Remember me?”

He blinks at you with those dark eyes, and he meanders a bit closer to the half door. You offer a loosely closed fist for him to inspect. When he does, you think it’s with some familiarity as he sniffs your hand all over. Or maybe he’s just smelling the apple pie glaze you licked off your finger earlier.

You laugh lightly and take a chance on petting the side of his neck. He lets you do it, a kind older statesman. Before you left, you had helped your dad break this horse in.

“He remembers you.”

You turn your head toward the door, flinching slightly in surprise. You didn’t even hear Dean come into the barn. His scuffed boots cross the distance leading him to you. Dark wash jeans and a black buttoned-down shirt are probably the extent of his cleaning up for the occasion, but the ensemble does suit him better than a proper suit would.

“It all looks the same,” you say quietly.

“That’s because it is,” Dean replies. His lips pull at a smirk as he points to the tool shed. “Like that dusty back room where we used to make out.”

You roll your eyes, but you can’t help the way your gaze draws to his calloused hands and long fingers. Your cheeks begin to prickle with warmth, but you refocus on his face, and unfortunately, that familiar grin. You’re sure that face has gotten him plenty of action since then.

“You do remember I have a fiancé,” you say.

Dean nods, holding up a placating hand. It slips into his pocket as he leans against a support beam. “Yeah, you never said where that guy was today.”

“Working,” you reply defensively. “We’re in the middle of a big project, and we can’t afford to drop the ball.”

“You two work together?”

“Yeah, for his father’s company.”

“Doing what?”

You hesitate. It seems like Sam hasn’t spoken to Dean yet about the offer either, but in this case, you’re grateful for it.

“Land development. His father is co-CEO and head of the Legal team. I help scope out properties and propose new projects,” you say.

Dean quirks a brow. “Land development, huh? Not what I would’ve imagined.”

His tone annoys you, making you slightly more tense, but you’ve already had this argument with Sam. You don’t have to explain yourself to this man.

“It’s not what I thought I’d end up in either, but if you think it’s hard to be a rancher, try being able to pay rent in California. We’re all just trying to survive, Dean,” you say.

At that, he actually nods more sincerely.

“Guess that’s fair. But it looks like you’re more than surviving now. You’ve got a friggin’ golf ball on your finger,” he says, gesturing at you, and more specifically your engagement ring.

You roll your eyes. “It’s not that big.”

The way he snorts earns a reluctant smile from you.

“How long you known the guy?” Dean asks.

You give him a shrewd look. He’s very curious about your personal life, but you can’t deny that you’ve been wondering what the past 12 years have made of him.

“About eight months,” you reply.

His brows raise almost as high as his hairline. “Eight months? When did he pop the question?”

“…A few weeks ago,” you say, albeit with some hesitation. “What?”

Dean shakes his head. “Nothing, I guess. Whirlwind romance.”

“And what about you?” you counter, fighting a blush. “No girlfriend?”

Dean chuckles. “Oh, I have plenty of friends. Just no time for the whirlwind.”

“I’m sure,” you say wryly. “Things really don’t change much around here.”

It’s a touch snider than you mean it to be. You don’t actually want to pick another fight. Frankly, you don’t have the emotional energy.

But even though Dean gives you a certain look, to your surprise, he doesn’t want to snipe anymore either. He just sighs.

“All right, come on. There’s some of Bobby’s stuff that you might want to look through,” he says, ushering you to follow him.

You do so reluctantly, over to the Foreman’s cabin.

The Foreman wrangles the other ranch hands, and he’s the Ranch Manager’s second-in-command. Bobby held that position for 23 years, starting from back when John was managing all operations himself. You used to live in this cabin with your mom and dad, back when they were together. 

Dean would later take your virginity when you turned 18—in the glorified closet that used to be your bedroom.

At least he doesn’t bring up that little anecdote as he leads you to the small, four-seater dining table. It has a few boxes stacked on top of it, probably what’s left of your father’s belongings. The rest has been cleared out except for a couch, an old wood coffee table, a TV on a stand, and some supplies in the kitchen. There are some signs of life here though, like a half-drunk beer on the coffee table, an empty box of pizza on the kitchen counter, and some crumpled napkins. Dean notices your observing gaze.

“I’ve been hanging out here the past few days. Cleaning the place up took a while, but uh, sometimes it’s nice to get away from the main house,” he says.

“I could see why. Thirty-two and still living with your daddy,” you teasingly remark.

Dean shoots you an amused brow raise, but he brings the first box to the living room coffee table and slides it toward you.

“Take whatever you want. He doesn’t have any other family, so I’m not sure what to do with the rest,” he says, rubbing a hand at the back of his neck.

Throwing it away feels wrong, or so his tone says. You nod in agreement and start looking through the box. The first thing you find is a large bottle of gold label scotch.

“Wow,” you say.

“That’s on brand,” Dean says, with a smirk. He eyes you. “We should probably crack it open, in Bobby’s honor, of course.”

Your lips tug at a smile. You hand it over, and Dean twists off the cap to take a swig. He offers it back to you, and you accept it dubiously after sitting beside him on the couch.

“You know we’re not teenagers anymore, right?” you say, but you still sip straight from the bottle just like he did, grimacing at the burn down your throat.

“We gotta lubricate this trip down memory lane somehow,” he replies. 

You snort in response and dig back into the box for something else.

Dean’s phone buzzes in his pocket. He checks and sees a text from Sam, asking if he’s with you.

Yeah, we’re going through Bobby’s stuff. I can come help. No need. It’s not that much. …Dude. What’re you doing? What? We’re good. Just catching up. All of a sudden you two are civil? I guess. It’s no big deal. We’ll be back in a few minutes. Ok. Just…be smart about this.

Dean frowns, resenting what his brother is insinuating. He glances up at you.

You haven’t noticed his silent conflict. You’re just looking through old baseball cards and faded trucker hats, rusty tools and piles of weathered flannel.

By the time you get to the third box, over an hour has passed, the bottle of scotch is almost empty, and you’re laughing harder and freer at the stories about Bobby that Dean’s pulling out easier than the next object. You haven’t even noticed that his knee rests against your thigh, or that you occasionally grab his forearm when something he says makes you particularly giggly.

It’s kind of cute that you still do that, but he keeps that thought locked in deep. His smile starts to hurt the corners of his cheeks, though.

Eventually, what you find at the bottom of the last box hits you so hard behind the ribs that it steals your breath. It’s a picture of you and your mom when you were around seven years old: your first year in this cabin, on this ranch.

To you it had seemed like a fun adventure, and so much cooler than your little boring apartment in Salida. Here, there were horses and cows and Sunday barbecues hosted by John Winchester himself.

It was on one of those Sundays that you met Dean, with all those freckles dotted across the bridge of his nose and cheeks, and the purest kind of happiness in his green eyes while he ate a slice of peach cobbler with a scoop of melting homemade ice cream. You remember him setting his own plate aside for a while though, just to comfort his six-year-old brother when his ice cream rolled off the side of his bowl into the dirt. Dean ended up slotting his own ice cream into Sammy’s bowl.

Bobby clocked what happened out of the corner of his eye. In the end, he was the one to slip you and Dean an extra scoop.

Your dad didn’t miss much, at least back then.

“I don’t get it, you know,” you say, somewhat shakily. “When we were kids, Dad was my safe place. Sure, he was gruff and curmudgeonly sometimes, but he was gentle too. He always looked out for me. I understand that shit didn’t work out between him and Mom, but I did try calling him. Years of five-minute conversations that never went anywhere, because he had to get back to the ranch.”

Your lips tremble and you try to blink past the sting, but the dam is already full to bursting, and your walls are failing all over again.

Dean watches you, and he actually listens as his heart grows heavier.

“I was a student. For a long time, I couldn’t afford to fly back to Salida,” you admit. “But he never once came out to visit. He didn’t even go to my college graduation. He showed up to Mom’s funeral. That’s it. I had to call the cemetery, the church, arrange the burial. I had to figure it all out by myself. And I get it, she left him. But he didn’t have to leave me too.”

You press your fingers over your mouth, as if that can stop the hurt from spilling out. You find sympathy in Dean’s eyes, but he doesn’t do what you expect. He rifles through the same collection of memories and pulls out a thin, white box.

Inside is a thin silver chain necklace with a small rose pendant. He lets the chain fall into your hand.

“He was going to give you this at your graduation,” Dean says. “I only know because he was hella fucking drunk one night, and he told me.” 

You laugh a little through unshed tears. You marvel at the necklace; it’s simple, dainty even, but beautiful. 

“Your mom told him not to go,” Dean says, earning your soft shock. “He hadn’t helped you pay for college, so in her mind, he didn’t have a right to see you. At least, that’s what he said happened.” 

“What?” you frown, rubbing the small pendant between your fingers. “I…can’t believe she said that.”

You had a partial scholarship and a work study job, but you wouldn’t have gotten through college without your mom. Living in San Diego hadn’t been easy at first, financially, and your mother was a nurse. You still don’t know how she managed it, but she always came through for you when it was time to pay for the next semester, and even for your textbooks.

You understood that even a Foreman didn’t make a hefty salary. It was part of the reason your mom gave you for leaving your dad. She didn’t come from a ranching family, and she had never wanted to spend her life on a ranch either, let alone one that your parents didn’t own.

In her words, “It’s hard to build a life on someone else’s land.”

She told you that she wanted more for you, and more for herself. Bobby hadn’t been willing to leave Winchester Ranch.

“He was dedicated to it. In some ways it was admirable, but in others…” she’d said, with an edge of bitterness.

You never really understood it. You realize now that you hadn’t tried hard enough. 

“I didn’t care about the fucking money or who paid for what. I just wanted him to be there,” you quietly confess. “But I know that’s a two-way street. I wasn’t there for him either.”

You look up at Dean, meeting his gaze.

“You were right,” you say, as emotion begins to choke you. “He had a goddamn heart attack, and I would’ve never known.”

Your shoulders shake as the first sob wracks through your body, but you soon find warmth and a familiar comfort in Dean’s arms.

“Okay, sweetheart. Come ‘ere,” he says, as he holds you close. There’s something different in his voice. Deep and a little coarse, but gentler. It’s the anchor you need right now, and you cling to it. You cling to him.

“It’s not your fault, okay? Seems like Bobby made his choices too,” Dean says. 

He tucks your head under his chin and briefly closes his eyes as he strokes your back. He feels every hiccup and unsteady breath in you, feels your tears dampening his shirt. His lips press to the crown of your head. Your fingers tangle in the green flannel at his back.

As you begin to relax after crying yourself out, your curled fingers smooth out into warm hands that release his shirt, but ultimately don’t move far, laid flat against his chest. He brushes frizzy strands of hair away from your face and behind your ear. You slowly look up to meet his eyes, with tears clinging to your lashes. Your lipstick is smudged, but you’re still a wonder to him.

It may just be the booze, but he remembers exactly how this used to feel. It cracks open something he’s been paving over, brick by brick. Year after year. He didn’t think this was what it would take to see you again.  

“Jesus,” he murmurs, brushing your cheek with his thumb. “You’re still so fucking beautiful. More, even.”

Your mouth parts with a hint of surprise, and a telling intake of breath. Your lashes lower as your gaze falls—to his lips.

What the hell is this?

You pull away from him, gently guiding his hand down.

He feels the sting of rejection, but also, his shame.

“’M sorry,” he says, looking away.

“…Yeah,” you say eloquently. You feel a prickle of guilt yourself as you wipe your cheeks.

You push yourself off the couch, but your body doesn’t cooperate well. Hard liquor hasn’t been your poison for a hot minute, whiskey least of all. Clearly, it’s remained a favorite of Dean’s.

But he’s far more than a memory you can shove to the back of your mind, especially when he gets up with you—to hold you and stop you from falling. He looks into your eyes, and the conflict in his makes you morbidly curious. What you would give to know what he’s thinking. 

“Just tell me one thing,” he says. “Does he treat you right?”

You frown. “Excuse me?”

His brows raise in challenge. “Come on. Work is work, but how’s he not gonna at least show up here for you?”

It probably makes him some kind of hypocrite, and he fights the voice inside that tells him he’s an idiot. An asshole.

But all you give him is the soft bite of your words.

“Not that it’s any of your business, but like I told you, our jobs are demanding,” you reply, crossing your arms. “He can be very considerate.”

Dean quirks a wry smile. He glances down at that ring, oval-shaped and vintage, putting it mildly. It would look real nice on his Great Aunt Matilda.

“Yeah, with this, huh?” he says, grasping your left hand. “Tell me this is some kind of kooky family heirloom.”

You slip your hand out of his. “He found it at an estate sale.”

“Oh, I believe you,” Dean chuckles. He taps the humble pendant that now has a place above your heart, after he helped you figure out how to put on the necklace it belongs to. “That’s more your speed.”

“How would you know?” you retort, batting his finger off. “It’s been all this time, and you think you still know me?”

You really do walk away from him now, beelining toward the door…

Well, you would have. You will. But his audacity truly is monumental, and after how he treated you this morning, this really is too much for you to wrap your head around. It derails what would’ve been a highly justified storm-out, and compels you back to face him in frustration.

“What’re you trying to do, Dean, spin my head around?” you snap. “You’re the one who broke my heart first. You don’t even know how much you messed me up.”

The confession escapes you before you can cram it back in, shocking you as well as him.

But it’s true.

Years. It had taken you years to get over him, your best friend. Your first real love.

Dean’s amusement faded the more you spoke.

“I know,” he says. And the admission costs him. Under the layers of bravado, bitterness and hurt, there’s the truth. “I was a stupid kid back then, who didn’t know how to let you go.”

You shake your head in denial. Your heart hurts, probably because it never healed right the first time.

“That’s bullshit,” you say. “You didn’t have to let me go. That was your choice.”

“Yeah, I did,” Dean says, with a newfound certainty that dims the light from his eyes. “You had a life ahead of you, sweetheart. Mine was always gonna be on this ranch.”

For a moment, you’re stunned where you stand.

Until reason and doubt start to compete for new ground in your mind.

He’s still making excuses, you think. He could’ve come with you to college. You told him that then, and even if his father tried to nail his boots to the ground, Dean never even called you once after you left. Where was this apology when it would’ve mattered?

“Jesus Christ, Dean…”

You rub your forehead at the headache you already feel coming on. You’re probably drunk, in fairness.

“Why are you telling me all this now?” you ask.

He sighs and rakes a hand through his hair, then rubs his eyes as well.

“Good question,” he chuckles slightly. He sobers when he meets your eyes again. “You told the truth today at the funeral. It’s only fair I give you the same courtesy.”

“Courtesy. Is that what this is?” you challenge.

“It’s an apology,” he says. “And uh, it’s goodbye, stranger, I guess.”

“Goodbye,” you echo. Though you’re unable to stop yourself from glancing down at his lips again. Then back to his eyes, despite the glassiness in yours. A hitch in your breath. “I guess it is.”

Dean sees it, another spark of your tears. He still hates it, both selfishly and unselfishly.

He can’t help but try to give you the stability you need. First, by his slow attempt to hold you, brushing his thumbs against your arms. Your mouth parts, but you don’t pull away.

He bows his head and follows the deep-seated need in his gut, urging him to press his lips to yours.

You breathe in sharply through your nose, but your fingers clench in his shirt again, near his collar. Your body melts willingly against his, like a muscle memory you thought you lost.

Then, the brush of his tongue short-circuits your brain. His hand moves down to the small of your back and presses you into him, eliciting tingles down your spine, and a blooming, pulsing heat between your legs.

You whimper into his mouth, and his hold tightens a fraction.

You pull back for a moment, panting for air. Your eyes meet his incredulously.

He steels himself, waiting for a slap, or at least a push.

You don’t have it in yourself to give him either one. Your heart clenches painfully, because despite the guilt and shame you already feel, something inside you, deeply vulnerable and frayed, needs this.

You tell yourself it’s just one more kiss.

He meets you halfway when you lean up to claim his lips. He claims you back, his hands once again molding to your waist, his arms caging you in, his hand sinking into your hair.

One more turns into him backing you up against the wall. You grab onto his shoulders for leverage, then his hair as his lips veer away from yours to blaze a hot, wet trail down your neck. Your moan is perfect in his ear, rattling down his spine and right to his cock.

You feel him heavy and thick through his jeans, pressing against you. His hand slips up your thigh, squeezing plush flesh as he goes. He bunches the skirt of your dress up to your hips.

“Unzip me,” you tell him, through hushed tones and heated breaths.

Dean nods, turning you around and brushing your hair out of the way so he can drag the zipper down in a slow, torturous tease. His eyes drink in every inch of your skin, but there’s nothing sexier to him than the way you brush down the sleeves and slip out of the dress the rest of the way. The fabric falls around your ankles, and you step out of them in your tall heels. Dean gets the full view of your lace panties, then the matching bra when you turn back around.

He catches your little intake of breath, like you’re guarding yourself before he sees you. He smiles and pulls you back in by your waist.

“Like I said, fucking beautiful,” he says, his gaze roaming your face.

Your lips tug at a smile as you meet his stare, but he finally renders you without a snappy word to say. He takes that win and revels in it as he kisses you.

You touch him more confidently than he remembers, dragging your nails down the back of his neck, sucking his tongue into your mouth, down to grabbing onto his belt and popping the buckle open. He follows your lead and helps you loosen his belt and jeans, but his boots and your heels are the first to form a haphazard pile on the way into the bigger bedroom, where his spare sheets and an old comforter line the bed.

He wasn’t lying to you when he said he’s been staying over here for the past few days. Not only so that he could clean up, but because he needed to clear his own head. Bobby’s death shook everyone, but it hit Dean in a way he hadn’t expected. He hasn’t told anyone this, but it was like losing a second father.

It reminded Dean of his regrets—his biggest one of all being you.

Despite how it looks, he knows it’s wrong to touch you. He knows it’s selfish to want you. But he hasn’t allowed himself to want anything in such a long time, and he thinks he might be able to right some old wrongs while he’s busy committing new ones.

After he lays you on the bed underneath him, Dean kisses his way along the column of your throat, down between your breasts. He slips a hand underneath you to unhook the pretty lace bra, and your back arches, giving him room. 

You really have grown up beautifully, even your boobs. Good for you, and good for him. Dean recommits them to memory as his tongue lavishes one of your nipples, while his right hand rolls the other between his thumb and forefinger. You sigh his name and slip your fingers through his hair, scratching his scalp with your nails. But your fingers hook on his flannel next.

“Take this off,” you breathe. “Want to see you too.”

Dean hesitates, but concedes to taking off his outer flannel. His undershirt stays on, even though you tug on it next. He aims to distract you by moving further down your body, laying open-mouthed kisses down your ribs and stomach, and over your mound, after he slips off your panties. He glances up between your legs and shoots you a mischievous grin.

“I used to love the way you tasted,” he says. “Those little sounds you made, the way you’d buck against my chin and scream my name… Let’s see if we can rock another sequel, huh, sweetheart?” 

“Dean,” you gasp, as his fingers slip between the folds of your pussy. They find slick arousal and heat.

“Jesus,” he murmurs. “You’re soaking wet.”

He bites his lower lip as his thumb searches, then finds your clit. Your hips start to writhe as you moan, grinding against his hand. He smirks in satisfaction before he lowers down. He moves your left thigh over his shoulder, and he feasts.

Your mouth falls open in a near silent cry, and your hips nearly come off the bed as you feel his tongue replace his fingers on your clit. Those long digits slip inside your hot channel. Hunger pools in your lower belly as your inner walls clench on him, desperately needing friction. Your breaths deepen as your free hand goes to your breast, toying with a hard nipple while you savor the sensations Dean’s giving you with his mouth and skilled fingers.

He curls his fingers and strokes you deeply, searching, exploring, until he finds that most sensitive place within your inner walls that has your body shuddering like an accordion. You grab a fistful of his hair as you buck hard against his mouth, a choked scream falling from your lips.

After withdrawing his fingers and wiping his mouth and nose, he presses a kiss into your inner thigh as you still tremble with the aftershocks of your orgasm.

He moves back up your body, and you take his face in your hands to kiss him deeply.

“What’s the verdict?” he teases afterward.

“You’ve gotten better,” you admit.

You sit up, intending to return the favor as your hands roam down his chest and underneath his shirt. He feels toned from long hours of hard labor and horse riding, but he stills your hands from grasping at the edge of his shirt. You’re confused, but he quickly guides you into turning over in the bed.

He kneels behind you as his steady hands continue to map every inch of your body. He caresses your sides, across your middle, and back up to your breasts while he kisses along your neck, then down your shoulder. There’s more calm confidence in his touch than he had at 20 years old, certainly more strength and more callouses, but it’s a delicious friction. And it’s a feeling that he absolutely has you enveloped in his arms, within his broad frame. You hang onto him on reflex.

Two of his fingers dip back into your pussy, circling your clit. You hang onto his arm as your body gives way to a moan. Arousal begins to pulse deep inside you again, but this time, you need his cock. You want to know if he’s improved there too. He seems to remember your body well enough.

“Dean…just fuck me,” you whisper coarsely. “Please…”

Before I lose my nerve.

“I gotcha, sweetheart,” he says, in a voice like old scotch and honey. Its depths make prickles of heat flash across your skin as fabric rustles. You assume he’s finally stripping off the rest of his clothes. You catch a glimpse over your shoulder of him tossing his shirt and boxers to the floor, but soon, the heat of his presence returns as he lines himself up at your entrance. His cock finally pushing inside you from behind makes your thighs tremble. Your nails dig into the mattress sheets.

“Dean,” you gasp. He stretches you so fucking good.

“You’ve got it, baby. Every damn inch, doing so good,” he says, breathing hard into your neck. His teeth graze your shoulder, making you shudder and push into him on reflex, sheathing him nice and snug inside. Already the walls of your cunt tremble around his cock.

Dean keeps his promise; it’s dewy skin against skin as holds you to him while he fucks you, slow, deep, and powerful, but never painful. Never too much.

He asks you what you want—faster or slower, rougher, or easier rhythm. You tell him you want him exactly how he is: fucking perfect.

And that night, it is fucking perfect.

Almost.

Both of you have left your cell phones on the kitchen table. They’ve buzzed almost half a dozen times, each with text messages and a handful of calls.

Your little black dress collects dust on the floor along with his jeans and flannel.

In the morning, long after he should, Dean wakes up nice and easy.

He just ends up waking alone.

AN: 🫣 Sorry loll. If you think those twists were fun, then get ready for a whole messy love triangle when Brady re-enters from Stage Left. 😬 (And are you curious about Dean and reader's past?)

Next Time:

What have I done?

Okay, you were drunk, but not that drunk.

You were in pain. Reckless. Selfish.

Shame invades your body and settles into your heart. All you can do is slowly, silently slip out of the bed without disturbing Dean. After reclaiming your clothes from the dusty floor and getting dressed, you hold back tears as you try to leave the tangle of desire and old memories, both beautiful and painful, behind you in that room. All you take with you is your phone and the silver necklace you already wear.

Although you wait to put on your heels until you get outside the cabin, that big stretch of hill up ahead to the main house is daunting.

“Mornin’.”

Your head turns sharply at the voice. You shouldn’t be surprised that someone’s already up this early, let alone one of the ranch hands. Benny. He’s tall and broad, like Dean, though with reddish brown hair and a thicker beard. He’s already dressed for the day in jeans and a long-sleeved shirt, drinking his coffee as he leans against the bunkhouse wall. You nod back at him with an awkward smile. 

“How you plan to get up the hill in those pumps?” he asks.

You sigh. “I don’t.”

You’re about to execute the worst walk of shame you’ve ever done, but at least it’s only for an audience of one. You slip off the heels and let the ankle straps dangle from your fingers as you walk barefoot on wet, dewy earth, all the way back up to the house. 

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John's famous barbecue pit spins the mouthwatering smells of smoked meats. The tables are lined up and filled with buttery cornbread, potatoes done three different ways (mashed, roasted, and casseroled), salads, slaw, carrots and corn, wild rice, homemade dinner rolls and garlic bread, and no less than five different flavors of pie. You spy Dean tucking into his third slice of cherry. Evidently, it’s still his favorite. A piece of pastry crust flecks from his lower lip as he jumps in with an old story.

“So I’m maybe…twelve, thirteen. Bobby’s trying to show me how to fix this patch of barbed wire fence. Because I’m young and stupid, I get it in my head to jump over it while the wire’s slack,” Dean starts.

Sam and couple of the cowboys, Benny and Cas, are already smirking, chuckling a little, shaking their heads. They’ve definitely heard this one before, and this time, you have too. A smile curves your lips behind the rim of your glass of whiskey and Coke.

“I make it over, but my leg gets caught in the slack, and I just go down hard, eating the damn dirt,” Dean says. He mimes the impact of his body hitting the ground, complete with admittedly impressive sound effects. “But now the wire’s tight. Rips through my jeans, my ankle, blood soaking through. But, uh, Bobby calms me down, you know. He takes out his tool belt, and he says, ‘It’s all right, son. That’s why God made pliers, for idjits like you.’”

Laughter ripples across the table. Even John smiles, shaking his head.

“Well, he cleaned me up best he could and helped me back up on my horse,” Dean says. His grin is warm, and his gaze spans far beyond his beer. “Dad didn’t even have to lecture me. You remember what you said?”

John nods in amusement. “‘Your own body’s gonna do the punishing for me, son.’”

“Right. My ankle was busted for three weeks. Couldn’t ride, couldn’t do shit,” Dean says with a chuckle. “And it was summer too.”

At least he didn’t have to go to school, but for a boy like Dean, being cooped up in the house was three weeks of misery. All he could do was watch from his bedroom window while you and Sam ran off to ride your bikes in town or go swimming in the river.

He looks down toward the end of the table, wanting to see if you remember those days like he does. What he finds is your empty seat. His eyes run a search—and eventually catch you making your way over to the barn. His brows furrow in confusion, but as the conversation spins and Benny takes over the reminiscing, Dean gets up from the table, ignoring the little warning tug in his gut.

“Gonna get another beer,” he says.

But Sam’s perceptive gaze follows him. While you venture into the barn, Sam sees his brother’s projected path all too clearly.

The smell of horse makes you gag a little, but after you enter the barn and switch on the light, yet another wave of nostalgia blasts you in the face. You recognize that tack and tool shelf on the right-hand corner, and the rack of shotguns and rifles on the far left. You know these stalls, and you greet each of the horses like old friends, even though most of them are new ones.

You stop at one of the middle stalls on the right, clicking your tongue at an older horse. His coat is a deep coffee brown, dappled with white on his hindquarters.

“Dakota! Look at you, handsome.” You smile brightly. “Remember me?”

He blinks at you with those dark eyes, and he meanders a bit closer to the half door. You offer a loosely closed fist for him to inspect. When he does, you think it’s with some familiarity as he sniffs your hand all over. Or maybe he’s just smelling the apple pie glaze you licked off your finger earlier.

You laugh lightly and take a chance on petting the side of his neck. He lets you do it, a kind older statesman. Before you left, you had helped your dad break this horse in.

“He remembers you.”

You turn your head toward the door, flinching slightly in surprise. You didn’t even hear Dean come into the barn. His scuffed boots cross the distance leading him to you. Dark wash jeans and a black buttoned-down shirt are probably the extent of his cleaning up for the occasion, but the ensemble does suit him better than a proper suit would.

“It all looks the same,” you say quietly.

“That’s because it is,” Dean replies. His lips pull at a smirk as he points to the tool shed. “Like that dusty back room where we used to make out.”

You roll your eyes, but you can’t help the way your gaze draws to his calloused hands and long fingers. Your cheeks begin to prickle with warmth, but you refocus on his face, and unfortunately, that familiar grin. You’re sure that face has gotten him plenty of action since then.

“You do remember I have a fiancé,” you say.

Dean nods, holding up a placating hand. It slips into his pocket as he leans against a support beam. “Yeah, you never said where that guy was today.”

“Working,” you reply defensively. “We’re in the middle of a big project, and we can’t afford to drop the ball.”

“You two work together?”

“Yeah, for his father’s company.”

“Doing what?”

You hesitate. It seems like Sam hasn’t spoken to Dean yet about the offer either, but in this case, you’re grateful for it.

“Land development. His father is co-CEO and head of the Legal team. I help scope out properties and propose new projects,” you say.

Dean quirks a brow. “Land development, huh? Not what I would’ve imagined.”

His tone annoys you, making you slightly more tense, but you’ve already had this argument with Sam. You don’t have to explain yourself to this man.

“It’s not what I thought I’d end up in either, but if you think it’s hard to be a rancher, try being able to pay rent in California. We’re all just trying to survive, Dean,” you say.

At that, he actually nods more sincerely.

“Guess that’s fair. But it looks like you’re more than surviving now. You’ve got a friggin’ golf ball on your finger,” he says, gesturing at you, and more specifically your engagement ring.

You roll your eyes. “It’s not that big.”

The way he snorts earns a reluctant smile from you.

“How long you known the guy?” Dean asks.

You give him a shrewd look. He’s very curious about your personal life, but you can’t deny that you’ve been wondering what the past 12 years have made of him.

“About eight months,” you reply.

His brows raise almost as high as his hairline. “Eight months? When did he pop the question?”

“…A few weeks ago,” you say, albeit with some hesitation. “What?”

Dean shakes his head. “Nothing, I guess. Whirlwind romance.”

“And what about you?” you counter, fighting a blush. “No girlfriend?”

Dean chuckles. “Oh, I have plenty of friends. Just no time for the whirlwind.”

“I’m sure,” you say wryly. “Things really don’t change much around here.”

It’s a touch snider than you mean it to be. You don’t actually want to pick another fight. Frankly, you don’t have the emotional energy.

But even though Dean gives you a certain look, to your surprise, he doesn’t want to snipe anymore either. He just sighs.

“All right, come on. There’s some of Bobby’s stuff that you might want to look through,” he says, ushering you to follow him.

You do so reluctantly, over to the Foreman’s cabin.

The Foreman wrangles the other ranch hands, and he’s the Ranch Manager’s second-in-command. Bobby held that position for 23 years, starting from back when John was managing all operations himself. You used to live in this cabin with your mom and dad, back when they were together. 

Dean would later take your virginity when you turned 18—in the glorified closet that used to be your bedroom.

At least he doesn’t bring up that little anecdote as he leads you to the small, four-seater dining table. It has a few boxes stacked on top of it, probably what’s left of your father’s belongings. The rest has been cleared out except for a couch, an old wood coffee table, a TV on a stand, and some supplies in the kitchen. There are some signs of life here though, like a half-drunk beer on the coffee table, an empty box of pizza on the kitchen counter, and some crumpled napkins. Dean notices your observing gaze.

“I’ve been hanging out here the past few days. Cleaning the place up took a while, but uh, sometimes it’s nice to get away from the main house,” he says.

“I could see why. Thirty-two and still living with your daddy,” you teasingly remark.

Dean shoots you an amused brow raise, but he brings the first box to the living room coffee table and slides it toward you.

“Take whatever you want. He doesn’t have any other family, so I’m not sure what to do with the rest,” he says, rubbing a hand at the back of his neck.

Throwing it away feels wrong, or so his tone says. You nod in agreement and start looking through the box. The first thing you find is a large bottle of gold label scotch.

“Wow,” you say.

“That’s on brand,” Dean says, with a smirk. He eyes you. “We should probably crack it open, in Bobby’s honor, of course.”

Your lips tug at a smile. You hand it over, and Dean twists off the cap to take a swig. He offers it back to you, and you accept it dubiously after sitting beside him on the couch.

“You know we’re not teenagers anymore, right?” you say, but you still sip straight from the bottle just like he did, grimacing at the burn down your throat.

“We gotta lubricate this trip down memory lane somehow,” he replies. 

You snort in response and dig back into the box for something else.

Dean’s phone buzzes in his pocket. He checks and sees a text from Sam, asking if he’s with you.

Yeah, we’re going through Bobby’s stuff. I can come help. No need. It’s not that much. …Dude. What’re you doing? What? We’re good. Just catching up. All of a sudden you two are civil? I guess. It’s no big deal. We’ll be back in a few minutes. Ok. Just…be smart about this.

Dean frowns, resenting what his brother is insinuating. He glances up at you.

You haven’t noticed his silent conflict. You’re just looking through old baseball cards and faded trucker hats, rusty tools and piles of weathered flannel.

By the time you get to the third box, over an hour has passed, the bottle of scotch is almost empty, and you’re laughing harder and freer at the stories about Bobby that Dean’s pulling out easier than the next object. You haven’t even noticed that his knee rests against your thigh, or that you occasionally grab his forearm when something he says makes you particularly giggly.

It’s kind of cute that you still do that, but he keeps that thought locked in deep. His smile starts to hurt the corners of his cheeks, though.

Eventually, what you find at the bottom of the last box hits you so hard behind the ribs that it steals your breath. It’s a picture of you and your mom when you were around seven years old: your first year in this cabin, on this ranch.

To you it had seemed like a fun adventure, and so much cooler than your little boring apartment in Salida. Here, there were horses and cows and Sunday barbecues hosted by John Winchester himself.

It was on one of those Sundays that you met Dean, with all those freckles dotted across the bridge of his nose and cheeks, and the purest kind of happiness in his green eyes while he ate a slice of peach cobbler with a scoop of melting homemade ice cream. You remember him setting his own plate aside for a while though, just to comfort his six-year-old brother when his ice cream rolled off the side of his bowl into the dirt. Dean ended up slotting his own ice cream into Sammy’s bowl.

Bobby clocked what happened out of the corner of his eye. In the end, he was the one to slip you and Dean an extra scoop.

Your dad didn’t miss much, at least back then.

“I don’t get it, you know,” you say, somewhat shakily. “When we were kids, Dad was my safe place. Sure, he was gruff and curmudgeonly sometimes, but he was gentle too. He always looked out for me. I understand that shit didn’t work out between him and Mom, but I did try calling him. Years of five-minute conversations that never went anywhere, because he had to get back to the ranch.”

Your lips tremble and you try to blink past the sting, but the dam is already full to bursting, and your walls are failing all over again.

Dean watches you, and he actually listens as his heart grows heavier.

“I was a student. For a long time, I couldn’t afford to fly back to Salida,” you admit. “But he never once came out to visit. He didn’t even go to my college graduation. He showed up to Mom’s funeral. That’s it. I had to call the cemetery, the church, arrange the burial. I had to figure it all out by myself. And I get it, she left him. But he didn’t have to leave me too.”

You press your fingers over your mouth, as if that can stop the hurt from spilling out. You find sympathy in Dean’s eyes, but he doesn’t do what you expect. He rifles through the same collection of memories and pulls out a thin, white box.

Inside is a thin silver chain necklace with a small rose pendant. He lets the chain fall into your hand.

“He was going to give you this at your graduation,” Dean says. “I only know because he was hella fucking drunk one night, and he told me.” 

You laugh a little through unshed tears. You marvel at the necklace; it’s simple, dainty even, but beautiful. 

“Your mom told him not to go,” Dean says, earning your soft shock. “He hadn’t helped you pay for college, so in her mind, he didn’t have a right to see you. At least, that’s what he said happened.” 

“What?” you frown, rubbing the small pendant between your fingers. “I…can’t believe she said that.”

You had a partial scholarship and a work study job, but you wouldn’t have gotten through college without your mom. Living in San Diego hadn’t been easy at first, financially, and your mother was a nurse. You still don’t know how she managed it, but she always came through for you when it was time to pay for the next semester, and even for your textbooks.

You understood that even a Foreman didn’t make a hefty salary. It was part of the reason your mom gave you for leaving your dad. She didn’t come from a ranching family, and she had never wanted to spend her life on a ranch either, let alone one that your parents didn’t own.

In her words, “It’s hard to build a life on someone else’s land.”

She told you that she wanted more for you, and more for herself. Bobby hadn’t been willing to leave Winchester Ranch.

“He was dedicated to it. In some ways it was admirable, but in others…” she’d said, with an edge of bitterness.

You never really understood it. You realize now that you hadn’t tried hard enough. 

“I didn’t care about the fucking money or who paid for what. I just wanted him to be there,” you quietly confess. “But I know that’s a two-way street. I wasn’t there for him either.”

You look up at Dean, meeting his gaze.

“You were right,” you say, as emotion begins to choke you. “He had a goddamn heart attack, and I would’ve never known.”

Your shoulders shake as the first sob wracks through your body, but you soon find warmth and a familiar comfort in Dean’s arms.

“Okay, sweetheart. Come ‘ere,” he says, as he holds you close. There’s something different in his voice. Deep and a little coarse, but gentler. It’s the anchor you need right now, and you cling to it. You cling to him.

“It’s not your fault, okay? Seems like Bobby made his choices too,” Dean says. 

He tucks your head under his chin and briefly closes his eyes as he strokes your back. He feels every hiccup and unsteady breath in you, feels your tears dampening his shirt. His lips press to the crown of your head. Your fingers tangle in the green flannel at his back.

As you begin to relax after crying yourself out, your curled fingers smooth out into warm hands that release his shirt, but ultimately don’t move far, laid flat against his chest. He brushes frizzy strands of hair away from your face and behind your ear. You slowly look up to meet his eyes, with tears clinging to your lashes. Your lipstick is smudged, but you’re still a wonder to him.

It may just be the booze, but he remembers exactly how this used to feel. It cracks open something he’s been paving over, brick by brick. Year after year. He didn’t think this was what it would take to see you again.  

“Jesus,” he murmurs, brushing your cheek with his thumb. “You’re still so fucking beautiful. More, even.”

Your mouth parts with a hint of surprise, and a telling intake of breath. Your lashes lower as your gaze falls—to his lips.

What the hell is this?

You pull away from him, gently guiding his hand down.

He feels the sting of rejection, but also, his shame.

“’M sorry,” he says, looking away.

“…Yeah,” you say eloquently. You feel a prickle of guilt yourself as you wipe your cheeks.

You push yourself off the couch, but your body doesn’t cooperate well. Hard liquor hasn’t been your poison for a hot minute, whiskey least of all. Clearly, it’s remained a favorite of Dean’s.

But he’s far more than a memory you can shove to the back of your mind, especially when he gets up with you—to hold you and stop you from falling. He looks into your eyes, and the conflict in his makes you morbidly curious. What you would give to know what he’s thinking. 

“Just tell me one thing,” he says. “Does he treat you right?”

You frown. “Excuse me?”

His brows raise in challenge. “Come on. Work is work, but how’s he not gonna at least show up here for you?”

It probably makes him some kind of hypocrite, and he fights the voice inside that tells him he’s an idiot. An asshole.

But all you give him is the soft bite of your words.

“Not that it’s any of your business, but like I told you, our jobs are demanding,” you reply, crossing your arms. “He can be very considerate.”

Dean quirks a wry smile. He glances down at that ring, oval-shaped and vintage, putting it mildly. It would look real nice on his Great Aunt Matilda.

“Yeah, with this, huh?” he says, grasping your left hand. “Tell me this is some kind of kooky family heirloom.”

You slip your hand out of his. “He found it at an estate sale.”

“Oh, I believe you,” Dean chuckles. He taps the humble pendant that now has a place above your heart, after he helped you figure out how to put on the necklace it belongs to. “That’s more your speed.”

“How would you know?” you retort, batting his finger off. “It’s been all this time, and you think you still know me?”

You really do walk away from him now, beelining toward the door…

Well, you would have. You will. But his audacity truly is monumental, and after how he treated you this morning, this really is too much for you to wrap your head around. It derails what would’ve been a highly justified storm-out, and compels you back to face him in frustration.

“What’re you trying to do, Dean, spin my head around?” you snap. “You’re the one who broke my heart first. You don’t even know how much you messed me up.”

The confession escapes you before you can cram it back in, shocking you as well as him.

But it’s true.