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You’re making dinner when Dean comes home. The TV is still on, and so is the smoke alarm.

“Son of a– Move!” His eyes widen at the sight of you fanning the fire on the counter. He quickly steps behind you and steers you aside with his hands on your waist. With practiced ease, he snuffs out the fire, though smoke still lingers in the air.

You don’t even know how it happened. One minute, you’re flipping through your magazine, waiting for the pasta to cook. And the next, you find your fluffball dragging the burning dishcloth across the countertop, a trail of fire following her like she was straight out of hell.

Dean already told you not to leave your magazines near the stove to avoid a fire hazard. But what are you supposed to do while waiting for the food besides reading? Your phone is too distracting. You’d forget about whatever you’re making the moment you start scrolling.

Welp. You should’ve just listened to the expert. Lesson learned.

Dean turns off the alarm and dumps all of the newest issues, or what’s left of them, into the trash, then turns to you.

“Damn it, sweetheart. How many times do I have to tell you to put these away? It’s dangerous. What if–” He tilts his head, and his voice softens instantly when he notices your tremble. His hands find your shoulders. “You okay? I’m sorry, baby. C’mere.”

He tucks you into his chest, arms around your smaller frame. You can hear the frantic heartbeat through his uniform shirt, which tells you the fireman is more concerned than angry.

“I’m okay.” You murmur, though your hands are shaking. “Sorry, baby. I didn’t think it would be that bad.”

“‘Course you didn’t.” His arms tighten around you for a second too long, like he needs to feel you, all warm and breathing, before he can relax.

“One of these days, I’m gonna come home and find you roastin’ marshmallows while my clothes are burning. Don’t get me wrong, sweetheart. I like surprises, but I prefer having a roof over my head.”

You huff a small laugh. “Hey!”

“What? Like you didn’t set our kitchen on fire ten seconds ‘fore I even stepped through the door.”

“It was the cat.” You mumble, and a playful scoff escapes Dean.

“Riiiight,” he drawls, his voice vibrating pleasantly in your ears. “And you were aidin’ it.”

“Did not!”

“Then how are you gonna explain that?” He jerks his chin to the trash, and your lips pull into a small pout as you wriggle in his arms. “It was herrrr!”

Dean barks out a laugh, shaking his head at your stubbornness. “Alright then, maybe we should do somethin’ ‘bout it. Teach the little felon a lesson. Maybe no treats tonight?”

Your cat chooses this moment to strut into the kitchen and mewl in protest like she’s been eavesdropping all along.

“You got a problem with that?” Dean turns his head to talk to her.

She answers with another meow. Then she rolls onto her back, wriggling on the kitchen island like someone else just did. Dean bites back another laugh, his eyes crinkling as he looks down at you.

“You realize your cat just committed at least three felonies, right? I swear, baby, she’d had it out for me since the day she got me called out to rescue your ass.”

“Pffft. Now you’re being dramatic.”

“Attempted murder, destruction of property, conspiracy–”

“That’s it.” You rise onto your toes and press a kiss to his lips. A small triumphant grin spreads across your face. You wanted to shut him up, and you did.

But the victory lasts about two seconds.

Before you can pull away, Dean’s hand is already in your hair, soft lips brushing against yours. “Not so fast,” he murmurs, settling his other hand at the small of your back to draw you closer.

He kisses you slowly this time, and you melt right into him. A soft hum escapes you when his thumb slips under the hem of your shirt and strokes your skin. Your fingers curl into the back of his uniform, holding on a little tighter.

The fuzzball purrs once but quickly pads out of the kitchen after realizing she’s no longer the center of attention. Probably off plotting her next crime.

Eventually, you come up for air because breathing is still a thing around here. Dean brushes his nose against yours, his breath warm against your skin. “Cheating.”

You let out a small, breathless laugh and return the nose kiss. “I’m sorry. You must have been fighting tooth and nail against it. Poor you.”

Dean snorts, thumb rubbing gently behind your ear. “Now, don’t get smart on me, trouble. You’re the one harborin’ a fugitive.”

“Really, Dean? We’re still on that?”

Another laugh rumbles in his chest as he hooks an arm around your waist and turns you back toward the stove.

It takes all of Dean’s strength not to smile bright at your text and reply to it with something sappy and sweet. He knows he could, knows you’d love it, knows he probably should; but the idea of letting himself show it scares him half to death. When you grow up being told the hand that feeds is feeding you poison, you learn not to trust the hand when it feeds you love. All he can do is hope you’ll wait the years it will take him to unlearn everything bad he’s been taught about love. Instead, he turns his phone back over and sets it back on the table. He’ll tell you he loves you when you come back to the room; because he’ll know it’s you, but also because saying it in person is more meaningful than saying it over text.

Dean must fall back asleep, because when he next opens his eyes, his arm is numb from hanging off the bed, and you’re seated beside him, legs crossed, nibbling on a muffin.

“Hi,” you chirp happily, brushing crumbs from your lip. “I was gonna wake you up soon, so your coffee didn’t get cold.”

He hums a low sound back, fumbling to press a soft kiss to your knuckles. You laugh as he chapped lips tickle your skin.

“Did you see my message?” you ask.

Dean blinks, nodding. “Yeah.”

“What’d you think?”

“’S cute, sweetheart.”

He can see your expression dip and immediately regrets it. Just as quickly as your grin crumbles, it replaces itself when you smile again and point in the general direction of his muffin.

“Eat it so it’s not lonely.”

Dean smiles softly at you; of course you’d worry about the muffins getting lonely.

“Alright,” he mumbles around a yawn, taking a bite.

“Is it good?”

Dean nods, swallowing. “Mhm.”

“Is it really, or are you just saying that?”

Dean grumbles an indignant complaint, pressing a messy kiss to your forehead that you try to duck away from to avoid getting muffin crumbs in your hair.

“It’s good! Promise,” Dean says, gesturing.

“Did you see my other picture?”

Dean frowns, staring at you, the corners of his mouth tipped down in that precious way that would make you cave if you weren’t on a mission to learn something important right now.

“What other picture?”

“The one I sent you last night. From the gift shop.”

His frown deepens as he scrolls through your texts to each other. He goes past the messages from yesterday, then back through every single one, hoping something will jump out at him. He finds the picture right where you said it would be, nestled between a text about dinner and another one about when you were coming back to the motel. There’s a photo of two rocks sat together on the windowsill, lacey white curtains tinted cream with age framing them like curtains of seafoam. The tall black one is heavyset in the top half and thinner in the second half, and the shorter rock matches the colour of your eyes almost too perfectly for Dean to believe it’s true. But the picture is right there in front of him, with an ever-present message accompanying it;

Us !!

Ice-cold guilt floods him when he realizes he saw that message and never said anything about it. Usually, he sends back anything as simple as a thumbs-up, or just a ‘yeah’, or even just mentions it to you in person when you come back from wherever you were. But not this time. This time, he saw the picture and fully intended to mention it, but the moment you were back it slipped his mind. Not because he forgets easily, or because the picture was nothing memorable to him. But because to him, it was so much more than just a picture of two rocks on a windowsill.

To Dean, it was a declaration that even in the smallest, most unsuspecting places, you will find your way back to him. And you will find him in every lifetime, in every variant of your love that exists in the world, and you will show him each time you find it. All those versions of the two of you existing at once, and he gets to love you in each and every one of them; and he loves you strongly enough that you find them in the world and send him those pictures. To Dean, it’s the most important thing in his life, because it means you love him as much as he loves you. To Dean, it’s terrifying to know that he loves you like that, because in his life, love gets rewarded with tragedy.

“Sweetheart, I-.”

Your face crumples, shoulders folding inward like you can put a shield up between them and pretend nothing is wrong.

“Dean, if you want me to stop sending them, just say that.”

“It’s not-.”

“You don’t have to play along with it,” you say, rambling now, your voice breathless and airy with poorly concealed disappointment. “You can just say it’s stupid and I’ll stop. You can just say you don’t want to be with someone who sends childish stuff like that. You can tell me it’s immature, I just need you to say it to my face.”

“I-.”

You take a sharp breath in, letting it out slow and wavy like the tides to the ocean. “Just don’t keep me around because it’s convenient, okay? Don’t…don’t make yourself deal with things you don’t want to deal with.”

Dean’s about to explain himself, but he’s stopped by Sam coming into the motel room, hair drenched by the rain and carrying a stack of books under his jacket. He shakes his head, looking something like an oversized dog when the water falls out of his hair, toeing off his boots and handing you the books with the kind of grim look that says you’re in for a rough one.

“What’s up, Sam?” you say, clearing your throat.

“For once, I have no idea. I got us some stuff that might help but…” He trails off, gesturing uselessly around the room once he’s freed his arms from the jacket. “It could be nothing. Or it could be something we haven’t heard of yet. Whatever it is, we gotta figure it out now.”

That week is the longest week of Dean’s life. Half because the monster you’ve been tailing is scary good at adapting its patterns to conceal its identity. It’s been almost impossible to track it, and the only reason you got to it in the end was because you helped Sam go through traffic camera footage and found a shape in one frame that wasn’t meant to be there. It was caught between two fenceposts with barbed wire strung between them, knotted together in the middle like the posts were holding hands. That right there was the other half of why the week felt so long; normally, you’d see those posts and send Dean a picture with a caption for him. The only picture you sent him this week was a page from a lore book with information you thought he could use working his part of the case.

He doesn’t get a chance to mention it for another week after that, because all that time is spent with Sam uncomfortably close, and a conversation this important doesn’t need prying ears, whether they mean to listen or not. He waits for the perfect time, which happens to be in the Impala while Sam’s back at the motel waiting on you and Dean to bring back dinner, and Dean’s waiting in the car with you for the food to be ready. He’s expecting to start the conversation with something meaningful and important about how he values all the pictures you send to him and how he remembers every single one with shocking clarity.

“I’m scared,” is what he says instead, surprising both you and him.

“You’re- Why?”

Dean’s beet red by now, embarrassed to have the conversation but embarrassed to spill this most precious part of him, the part that he keeps locked tightly away in case anyone dares to question it.

“Dean is this about the pictures?” you press, gentle as ever.

“Yeah.”

You stutter a laugh into the palm of your hand. “What’s so scary about the pictures?”

“It’s not the pictures, sweetheart. The pictures are great, I promise.”

You narrow your eyes, staring at him through your lashes. “Then what is it?”

He takes a deep inhale. “I’m scared that…” A deep exhales, followed by another inhale. “I’m scared of how much I love you.”

He rushes the last part of the sentence so much you barely even catch what he’s trying to say. But you’ve spent years getting close to Dean, you know how to interpret every mumbled word of his uttered into your skin. And this whispered sentence makes your heart drop to your feet and cry tears of something bittersweet.

“Dean, baby…” you murmur, holding one of his hands in yours.

Dean braces himself for rejection, for what inevitably happens when he opens up to anyone that matters to him. It happened to him with his dad, with Sam, with Cassie all those years ago. And now it’s about to happen again.

Except you don’t insult him or throw him out of the car like he’s nothing more than an empty plastic bag. You take his hand in yours and you stretch out his fingers, and you press them to your lips, kissing the callouses that live on their pads.

“Why didn’t you just say that?” you whisper against his skin.

And Dean, darling emotional Dean, feels his cheeks dampen under tears he didn’t know were falling.

“’Cause that made it real. ‘N ‘cause I don’t want ‘em to take you away.”

“From you?” you murmur.

Dean nods, wiping at his cheeks.

“They can’t take me away from you.”

“You don’t know that.”

You smile, pressing a soft kiss to his temple. “Yes, I do. D’you know how?”

Dean shakes his head, sniffling.

Another kiss to his temple, and you continue.

“’Cause I see us together all the time. We’re always gonna be together somehow, even if it’s just in stupid little pictures. They can take my body if they want, but they can’t take away what we have.”

Dean’s head falls to the crook of your neck, and you tuck it there, hand cradling his head, murmuring reassurances into his sandy hair that pokes your cheek. You rock him slowly back and forth, one hand playing with his hair and the other one rubbing circles over the cotton of his dark t-shirt. You sit there until Dean has to go in to get the food, and when you’ve brought it all back to the motel and are settling in for the night, you hold Dean against your chest the exact same way as he sleeps.

When Dean wakes up the next morning with sand in his eyes and a headache from crying, he turns on his phone to ask where you are. And the first thing he sees is a picture of two bunnies sitting side by side near the parking lot, a huge dandelion stem sat between them. And a caption, with your signature

Look, it’s us !

"Stop moving- let me take care of you."

He says it firm, a short breath pushed out his nose. He's trying to sound patient, but with your blood still seeping out of the cut in your leg, he knows he needs to get you bandaged up quick.

You'd do the same to him, frustrated as you both try to sort through each others injuries. But that frustration never lasts. It always ends with him kissing your forehead, an affirmation that he's not actually angry- and that you're okay.

"Stop moving, baby, I'm takin' care of you."

It's not like you have a choice- wrists bound to the headboard, stretching your arms above your head as you lay against the mattress. Your hips are still lifting off the bed, thighs twitching as Dean dives his head back between them.

His tongue presses against your clit again- you tug at your restraints, another loud moan pushed out of you. You feel him grin, looking back up, "Thought I told y' to stay still."

"You want me to teach you?"

He raises an eyebrow, a genuine question. He likes being able to show you things, likes being useful. It's difficult with you- when you already know so much, when you have hunters instincts and skills he sometimes feels envious of. He secretly relishes those small moments where he can actually teach you something new.

You nod, looking down at the gun in his hand, the object of question in the first place- "Yeah- yeah show me how you did that-"

"You need me to teach you a lesson?"

You've been teasing him all day- the makeout in the police station that left his cock swollen in his pants, the way you flirted with the witness while keeping your glances on Dean the whole time, your outrageously short skirt. You knew he was gonna get you back for it- but maybe that's part of the fun.

He's got you pulled over his lap, that same skirt bunched up to your hips, his handprint already etched red against your skin.

"This what you've been asking for all fuckin' day?"

"Dean-" you whine, cheek pressed against the sheets.

"Asked you a question, sweetheart- you better start answering-"

"You just need to relax."

He's got the bath running, your candles are lit in the corner. Your body's still aching from the hunt, your mind more exhausted than you realized. He helps you pull your T-shirt off over your head, you manage to get your own pants down.

"You want some ice-cream? I've got some in the freezer- get in the bath and I'll grab you a bowl."

"Relax, darling."

His body envelops you, touching every part- lips on your neck, one hand on your chest, the other wrapped around your hip. He's going slow- torturously slow. He knows it's making you frustrated, whiny and bratty as you try to lift your hips for friction.

But he likes you like this- that's why he's gonna keep you on the edge, smiling against your body like he's just trying to be sweet. "You gotta take it easy, sweetheart, let me take my time."

"Jesus- that tastes good."

Dean doesn't trust Internet reviews- why should he believe strangers online, who gives a shit about their opinions?

Which is why you've started working strategically. You've got a list of the top burger spots in each state- you leave little hints during cases, "maybe we should head north after this, see if there's any more leads?", "let's come off the highway, I wanna go the scenic route.", "hey I'm getting hungry, why don't we stop here?".

This time it's paid off, Dean thinks he's found a hidden gem- the grease from the bacon coats his lips, fries scattered across the plate. He grins at you, still chewing the bite- "How'd you always find such good places?"

"Jesus- you taste good."

He looks up at you from between your thighs, eyes glosses with admiration, trying to hold himself back from rutting against the mattress like a fuckin' dog in heat.

He always gets like this when he goes down on you- you've actually had to stop him during cases coz you know it makes him so dumb he'll be useless for the next 3 hours. His tongue circles your clit again, fingers pushed into you to the hilt. He's gonna make you cum at least 4 more times before he even thinks about getting his cock inside you.

"So good- fuck sweetheart- fuck-"

///

Dean glances down at each packet. He snorts and tosses the first one into the metal garbage bin beside his desk. Sam frowns.

“What was wrong with that one?”

“He’s a dude. Don’t you think we’ve got enough of a sausage fest going on around here?” Dean says, gesturing wide at the multi-floor building that makes up HunterCorp. His father’s enterprise, distilled down to two sons who, on their best day, have very different opinions on what makes for a good executive assistant.

Sam utters a longsuffering sigh.

“Man or woman, you need a real assistant, Dean. Someone competent enough to deal with your demanding schedule and…personality.”

“What’s wrong with my personality?”

“And I need you to have an assistant so I can focus on my real job. You know, running the entire Legal department.”

Dean rolls his eyes. “I know how to do my job, okay? I think I’ve picked up the slack pretty damn well since Dad died.”

Sam pauses, acknowledging that with a nod, and a heavier note.

“Yeah. You have.”

“So while I’m throwing money away hiring for a wholly unnecessary assistant, who I’m gonna have to tolerate looking at every day, I might as well be looking at somebody hot,” Dean says.

Another exhale leaves Sam’s body, along with the brief buoyant feeling of admiration for his brother.

And now we’re back where the neanderthals live. 

Sam gets a text from Reception that has his pocket buzzing. After he checks the message, he nods to himself. Here we go.

“All right. The first one is on her way up now, so do me a favor and get yourself together,” he says. “For example, it’s a little early for the booze, don’t you think? It’s 10:00 a.m.”

Dean pauses. The crystal decanter in his hand is halfway to pouring his first fifth of whiskey.

Second breakfast, if you will.

He gives his brother a flat look, one that’s accusing him of being an eternal wet blanket. But he begrudgingly concedes the point and puts both the decanter and the tumbler in a cabinet under his desk.

Classy. Sam rolls his eyes.

A knock at the door stops him from commenting out loud.

Clearing his throat, he walks over to let you in.

“Hi, Sam…and Mr. Winchester,” you say, shaking hands with the slightly taller brother. Then you turn to Dean Winchester, CEO of HunterCorp. He stands and leaves his desk to greet you.

In the time it takes him to cross the room, he takes you in within the breadth of a few seconds. More than the professional pantsuit and your pretty face, he notices your bright smile, the slight bout of nerves in the way you shake his hand. He finds himself smiling back.

“Uh, hi,” he says eloquently. “Call me Dean. Can we get ya some water, coffee, iced tea…”

He doesn’t even think they have iced tea, but he’s willing to make Sam go and find some.

“No, thank you. I’m fine,” you reply.

“Okay, then. Just, uh, take a seat.” He gestures to the open seat in front of his desk before he returns to his own plush leather chair. It squeaks as he swivels back in place. He shares a nod with Sam, who heads out of the office. The door closes behind him.

Dean glances down at the list of questions Sam prepared for him to ask each candidate, a sheet of paper that lies over your resume. He brushes the questions aside and focuses on the information printed under your name.

His brows raise in interest. “You graduated from Stanford University like my brainiac brother?”

The sound of your light laugh draws his gaze from the page, up to your face.

“Yeah, we were actually friends. It’s just been…a while,” you say, clearing your throat a little.

Dean inclines his head. His understanding grows along with his suspicion as he reads.

“Look at that, a Marketing major. Looks like you had a couple of promising internships too.”

“In college, yes.”

“And you were a Communications Specialist at Ashland for…eight months in 2021?”

“Yes, that’s right.” Again, you nod, smoothing a non-existent wrinkle in your pants. Your gaze falls away from his.

This time, Dean thinks you know full well what he’s getting at when he sets down your resume.

“That was five years ago,” he says. “You haven’t worked in five years since getting out of college?”

“It’s a bit complicated,” you admit, though you sit a little straighter. “I gave birth to my daughter, Emma, in November of 2021. My ex…was not supportive. My mother was also having some heath issues, so I moved back home to help my father take care of her. They took care of me too.”

Your fingers flex and interlace together in your lap. Dean notices the subtle fidget, but otherwise you’re calm and professional as you admit to something so personal. He can respect that you didn’t try to bullshit him.

“Hmm. Complicated,” he nods, then hesitates. “How’s your mom doing now?”

Your lips tug, but not at a smile. “She passed away a few weeks ago.”

Dean dims further as he inhales deeply. “I’m sorry.”

You give a tight nod, your throat swallowing.

“Look, since you’ve been honest with me, I’m gonna be real with you,” he says. “I run a company of 300 employees, 20 departments, 10 floors. I work 60-hour weeks minimum. I meet with department heads, shareholders, business partners and prospective clients on the daily—the kind of schedule that would make your head spin. I know you’ve done what you had to do, but I’m not sure you’re ready for a job like this. And that’s besides the fact that I’m not convinced I even need an assistant who’s probably just going to slow me down by sticking her nose into my process and asking questions I don’t have the damn time to answer.”

You tighten up at that, understandably taken aback. Your lips purse, but instead of tossing him a fuck you then and walking out, like he half expects, you sit with his words. You think it through, and you give him exactly what he doesn’t expect. 

“I may not have been clocking into an office for the past few years, but I haven’t been a stranger to hard work, Mr. Winchester. I’ve done nothing but fulfill the role of an assistant,” you say, and your gaze never leaves his when you say it. “Appointments, calls, messages, emails, paperwork, finances, data reports, coffee, power lunches, drycleaning—whatever you need, however quickly you need it, I can get it and I can make it happen. If there’s someone you can rely on, it’s a single mother who knows how to get shit done.”

Dean understands now. He understands the pain hidden in your eyes, and the too-tight set of your shoulders that hold the weight of responsibility. Urgency. A hint of desperation.

You need this job, maybe a little too much.

He should let you down gently. You’re not the kind of girl he’s looking for.

But whenever his mind and his gut are in conflict, he usually heeds his gut. That’s worked out well for him so far.

So he shrugs, and he stands up, holding out his hand to you across the desk.

“Like I said, call me Dean.”

Two Weeks

He groans into the ceramic mug at the first sip. Jesus Christ, you make a good fucking cup of coffee. That’s not even in the top five of the talents you possess, as it pertains to his business and your ability to learn quickly, talk minimally, and begin to anticipate his needs.

You dress nice, you’re always on time, and hell, you smell good too. Like body lotion and just the right amount of perfume. Obviously he can’t comment on any of these things, unless he wants a visit from Meg in HR. But it doesn’t stop him from noticing you, his heart thumping whenever you come in close to show him a document or ask him a question about a report.

Instead of rolling his eyes or snapping that you should have someone who’s not running this entire company explain it to you—like he did the last assistant who didn’t even survive three days—Dean finds an ounce of patience to spare for you.

He sits there and explains the difference between an M1911 handgun and a shotgun, and why the background checks take two months for one model and a few weeks for the other one is just a difference of state law, not HunterCorp’s manufacturing techniques.

Sam is rather fucking gloaty about it too—mainly at the fact that his top candidate made it through Dean’s initial hiring plans.

“Admit it, she’s good,” Sam says later in the day, while the two of them eat lunch together in his office. You just had it delivered ten minutes ago, still piping hot.

“She’s all right, for being your little college friend.” Dean slurps his lo mien and casts his brother some side-eye. “Is that all she was, or did you two occasionally sneak off for a little rec room break on the side?”

Sam gives him a flat look. “No, I was with Jess by then.”

“Just asking.” Dean shrugs. Secretly, he’s pleased. “You know anything about the ex-boyfriend, Father of the Year?”

Sam snorts in derision. “Some asshole in Sales while she was at Ashland. From what I heard, they were dating for six months or so, and she got pregnant. He, uh, tried to get her to end it.”

Dean frowns, and actually pauses eating to raise his head.

“She told you that?” he asks.

Sam holds back on answering for a suspicious moment, his eyes shifting down at his food.

“Made a couple calls to some contacts I have over there,” he says.

Spies, in other words. Dean nods in understanding. His brother’s always been the smart one. That’s what everyone used to say, including their father.

Two Months

You’re not sure if you should do it.

You have a sensitive report in your hand, fresh off the printer. You really think Dean should see it before he gets any deeper into his negotiations with Roman Enterprises, but he’s meeting with them right now in the big conference room, with Dick Roman himself, as well as the rest of his sales and legal representatives.

This isn’t the first meeting Sam and Dean have undergone with the company; Roman Enterprises been courting HunterCorp into a partnership on a new product, but this could be the day that makes the big swinging dicks in the room shake hands (even if that little visual almost makes you snort).

Dean’s never expressly warned you about entering a meeting uninvited, but it’s still nerve wracking as you stand outside the door. You can hear familiar voices, including the nasally tone of Alastair, the one who gives you the creeps whenever he slithers through the office and gives you a “charming” once-over.

But you also hear Dean. His voice is deep and smooth and confident. It gives you the little confidence boost you need to twist the knob and push the door open.

Just as you predicted, with a sinking feeling, all eyes turn to you when you enter the conference room. Sam and Dean and their lead sales manager, Cas, look over at you in varying degrees of surprise (Cas with disapproval). Dick Roman remains impassive, if slightly amused when you squeak out an, “I’m sorry.”

It’s Alastair’s gaze you feel on your profile when you quickly make your way around the large conference room table and over to Dean. You lean over to hand him the paperwork.

His lips purse when he notices the line of Alistair’s gaze—on your ass.

Dean then frowns at you, and your express delivery.

“What’s this? You think it could’ve waited?” he asks in a low whisper.

“Look,” you whisper back, pointing to the section you starred. It’s a report that Roman Enterprises failed to disclose about their product, a double-chambered gun that can store silver rounds and witch-killing bullets as well as salt rounds: the perfect gun for a hunter.

The problem is the safety and performance report. The one Dean has up on his laptop doesn’t match the one now physically in his hands—the one that says two out of three units of this gun fail to chamber correctly on reloading, resulting in a backfire on the user.

Dean’s brows furrow. “Where did you get this?”

“Is something wrong?” Dick asks. He straightens in his seat, his demeanor a fraction sharper.

Dean glances up at him, then at Sam and Cas, who wear similar looks of confusion. Sam raises his brows expectantly.

“Sorry, one moment,” Dean says to the room, before redirecting his attention to you.

You’re all too aware of being the rabbit caught in the proverbial trap in this room of nearly all men, but you rest a hand on the table and lean in near his ear.

“Their weapons analyst sent this to me,” you explain. “He almost got his hand blown off. Said they didn’t want to go back to the drawing board and waste time when they had us as a prospective distributor.”

Dean blinks in surprise. A fucking whistleblower just outed his own company, but he supposes he can’t blame the guy. If he had half a hand, he’d sue everybody.

“Okay, thank you,” Dean tells you.

It sounds like a dismissal, and truth be told, you’re ready to get the hell of this room. You make a quick escape and shut the door carefully behind you.

Dean watches you leave, but then he collects the report you gave him and passes it along to Sam, with a pointed look that says read it now. Sam doesn’t need the prompting. He shares it with Cas, and they both eventually come to the same frowning conclusions as Dean.

“You gonna fill us in on what that little skirt just gave you that has all of you so fucking sour?” Alastair remarks.

It makes Dean bristle. “That’s my assistant. Have some fucking respect.”

Dick shoots his associate a warning look, as well as a placating hand before he folds both of his on the table.

“Apologies. I’d like to move forward here. How about we discuss oversees shipping—”

“No, I don’t think that’s necessary,” Dean says. He shares a look with Sam. He’s disappointed, but he nods in agreement all the same.

Dick’s head tilts. His fake-ass smile twitches at the corners. “Excuse me?” 

Dean closes his laptop and slides your report across the table.

“We deal with all kinds, but there’s nothing I hate more than a liar,” he says. “Cas will see you guys out to your line of Teslas out front.”

You’re sitting at your desk, stress-eating with a snack bag of popcorn while you answer emails, even though your mind is racing as you imagine what might be going on in that conference room.

You perk up in your seat when the door swings open, and the entire team of Roman Enterprises files out with steam practically coming out of Dick’s ears. You’re more than happy to see the back of Alastair. Cas follows them closely, while Sam and Dean are the last ones lingering outside the door.

They speak for a moment there in the hall, though you’re too far to hear what they’re saying. Dean eventually rubs a hand over his stubble-covered cheeks and jawline as he heads toward his office, and toward you. He gives you a wry look when he steps through the glass doors of the reception area, squeezing your shoulder as he passes by.

“Good job, sweetheart.”

That’s all he says as he disappears back into his office. You can’t help the warm blush blooming across your cheeks, but you do get up to follow him.

“Um, Dean…”

He turns to you as the door of his office closes behind you. You fold your hands in front of you, an almost contrite expression across your face.

“I’m sorry. That just cost you a lot of money, didn’t it?” you ask.

Dean shakes his head. “Don’t be sorry. What you saved me is one bitch of a headache, and probably millions in legal fees. So thank you.”

You smile, making him smile in return.

“Okay, um, would you mind if I leave just a few minutes early today?” you ask. “My father usually picks up my daughter after school, but he has a doctor’s appointment. I can come back after she’s settled.”

Dean frowns. “What time does she usually get out of school?”

“Three. She’s in kindergarten.”

He considers it for a moment. “You know, we have a daycare. Cas brings his kids here too.”

You do know that, all too well. Cas is married to Meg in HR, and they have two, very odd twin daughters. You think they’re stealing ink from the printer and using it for “ink blot tests.” You didn’t know that eight-year-olds knew what those were.

“We do. But I, uh…I can’t afford it,” you admit, with some embarrassment. You’re still helping your dad pay off your mom’s medical bills, and even her funeral. It’s not easy to afford to live and provide for a child, but it seems like it’s almost as expensive to die.

Dean taps his fingers on his desk. He shrugs and rounds his desk to sit down in his comfortable chair.

“How much does it cost?” he asks.

“$500 a month. I’m already trying to get her into a private school…”

Dean does the math in his head, easy. Then he sends a quick text to Meg in HR.

“Well, now you can afford it. I’m gonna raise your annual salary by $10K,” he says. “That should cover the tax deductions and extra gas mileage.”

Your mouth falls open in shock. It closes, then opens again before you’re able to make words pass through them.

“Um, w…what?” you ask.

Dean leans back in his chair and smiles. It isn’t often he gets you flustered.

“Consider it an early Christmas bonus,” he says.

You laugh, slightly breathless still in wonder. “It’s the middle of July.”

Again, Dean shrugs. “Just say thank you.”

You bite your lip in amusement, but you nod. Your gaze on him is sincere, and a little shiny with emotion. Your daughter’s definitely getting into private school now.

“Thank you,” you say.

Dean watches you walk out of his office, along with that brief look over your shoulder before you close the door. His smile fades.

“Fuck,” he mutters.

He sits up in his chair and goes for that stash of whiskey under his desk. If he wasn’t already an alcoholic, you sure were on your way to making him one.

Three Months

Dean blows out a sigh, then rubs his eyes at the strain of just how long he’s stared at a screen and tried to make these goddamn numbers work.

The building is probably empty by now. Even his brother left two hours ago to go home and have dinner with Jess. Dean’s reluctant to go home to his empty apartment. So here he sits, the workaholic that he is, as the sun fades behind other buildings and casts his apartment into darker shades. He switches on the desk lamp.

A knock on the door kicks his thoughts out of alignment, like an old engine sparking out, into crispy defeat.

“Yeah,” he calls out without looking up. He does though, when you come into view.

“Hey, I’m heading out,” you say.

He can see you’re ready to go, packed up and on your way downstairs to pick Emma up from daycare. He still hasn’t met the kid. He’s surprised himself with the idea that he wants to, though he’s never asked. Never wanted to intrude on your life outside of work. Never wanted to get too close to it.

You’re a single mother living with your father, and that’s complicated enough. You don’t need a man like Dean upsetting the delicate balance. And he doesn’t think he can give a woman like you what you need…besides the fact that you’re his employee.

“All right. Make sure Benny keeps an eye on you heading to your car. It’s getting late,” he says.

“Not that late,” you say with a smile. Though you’re a bit concerned when you step further into his office. “When do you typically head home?”

“Uh, around eight or nine, usually.”

“That’s pretty late. You don’t have anyone waiting on you?”

“Not unless you count the beers in the fridge,” he remarks, sending off another email to a sales rep to get his ass in gear if they’re going to make quota for Quarter 3.

By the time Dean looks up, he sees your small frown. Concern.

It rubs him the wrong way (or maybe the right one), so he clears his throat and waves you over to his computer, opening up a tab he was looking at earlier.

“Hey, do me a favor. Tell me what you think of these. I have to go to some tech expo this weekend with Sam,” he says.

You look over his shoulder at the rows of ties on the screen.

“Well, first of all, don’t get them off Amazon. Go to a men’s store,” you say with a short laugh. “Second, what color is the suit?”

“Uh, just black,” he says in amusement.

You hum in contemplation. The man does look good in his usual slacks and nice buttoned-down shirts, but picturing him in a full suit and tie is an enticing image.

“This burgundy one looks nice. Or the blue one with the pattern,” you suggest.

“You don’t think it’s too loud?”

“No, I think it would look nice with a black dress shirt. Or hey, a black vest with a white dress shirt underneath.” 

“A vest?” Dean intones.

“Yeah, with your shoulders, you’ll look really sharp when you pair it with the suit jacket,” you say.

“My shoulders, huh? What about ‘em?” he asks in amusement, verging on the edge of flirtatious, before he realizes what he’s doing.

You both pause then.

You eventually find something approaching a respectable response, if not really a professional one.

“Just…you have a strong frame for a suit. I’m sure whatever you pick will look good,” you say. Though you turn away to grab your purse from where you left it leaning against his desk on the floor. Your face is blushing hot all the while. “Um, have a good night. I’ll see you tomorrow.”

“Yeah, you too,” he nods, clearing his throat. He tries not to watch you leave, but he can’t help himself. The natural sway of your hips is too hard to ignore, as is the way you walk away from him on those heels.

Once the door is firmly shut, he tips his head back against his chair and groans. He hates himself for hoping, even fantasizing, that one day you’ll come back and straddle him on this goddamn chair and fuck him with those heels still on.

He bangs the back of his head repeatedly against the chair, as if that could rid him of his pig-like thoughts.

Fuck. Me.

Four Months

Dean steps into his office after four hours of solid back-to-back meetings. If he had to sit through even five more minutes of Crowley’s condescending ass explain 15 subsections of a contract, as if Dean didn’t know how to fucking read, then he was going to throw his laptop into the nearest window.

He expects to find the quiet refuge of his office, and very quickly his stash of Angel’s Envy. What he gets is a kid sitting in his chair, eating his Doritos. She doesn’t look older than five or six, swinging her little legs as she swivels in his nice leather chair.

The sight is so dumbfounding that Dean stops not two steps through the doorway, his hand still lingering on the doorknob. He frowns.

“Hey,” he says. Not in a nice way. In a who the hell are you way.

“Hi!” The kid smiles and waves at him with fingers coated in Cool Ranch Dorito dust.

Dean’s head tilts. “Uh, hi.”

“You said that,” she says.

His lips twitch upward. He points at her, and the chair she’s sitting in.

“That’s my seat,” he says, with some censure in his voice. “You wanna get down?”

She blinks and pauses, realizing she might be in trouble.

“Sorry.” She slides down carefully without letting go of her snack. She wears a private school uniform: a plaid skirt, navy polo, and a matching headband. Her pink Peppa Pig sneakers give away her personality though. It matches her backpack, which boasts a Minnie Mouse keychain and a princess sticker of Belle in her yellow ballgown.

“What’s your name?” he asks.

“Emma,” she replies.

Dean’s brows raise high in recognition, then they furrow.

“Interesting. Where’s your mom?”

“She had to talk to Miss Nancy, so she told me to stay here.”

Miss Nancy. Gotta be the daycare lady, Dean thinks.

“Here? As in, my office?” he asks in suspicion. “Or did your mom tell you to hang out at her desk?”

Emma guiltily glances down at her feet instead of at him, like Sammy did when he was four, and didn’t want to admit he broke their dad’s watch.

Here, it looks like Emma got bored and wanted to go into the big mysterious room. She continues eating her Doritos.

Dean can’t help but smile. “Did you find those in my desk drawer?”

She blinks up at him with the face. Like when Sam got caught looking through their dad’s old collection of baseball cards with peanut butter and jelly stains on his hands. That puppy dog look had Dean taking the fall—and the week-long grounding.

Emma tentatively offers him her snack. “Want one?”

The look on her face tells him that she’d rather not share, but it’s a clever little manipulation with those big doe eyes. Girls learn quick, don’t they?

Dean shakes his head and pulls out a nearby guest chair after setting down his laptop on the desk.

“It’s okay. You can sit here if you want,” he says.

The chair is a little high, so she reaches for the edge of his desk to help her. Dean offers her his hand instead. She’s happy to settle her little Dorito grime-covered hand in his and have him help her into the chair.

“Thank you,” she says, with that cute little voice. He almost laughs.

“You’re welcome,” he says. You’re definitely going to owe him for this one.

Dean sits at his desk and contemplates just what the hell he’s going to do with this kid for the next few minutes. At least, he hopes it’s just a few minutes. Does he need reinforcements? Should he call Sam up here? Cas?

“Are you and Mommy friends?” Emma asks.

Dean considers her question with a quirk of his head.

“Yeah, I guess you could say that. I work with your mom.”

“She said you’re her boss.”

“You know who I am?”

“Yeah. Your face is on her phone when you call,” Emma says. When she finishes the chips, he can tell she’s looking for a garbage can. He takes the empty bag from her and tosses it in the small bin under his desk. He wishes he could pour himself a much needed adult drink, but he thinks you’d have something to say about that later.

He settles on the bottles of water you keep putting in his other drawer. He grabs one for the kid, and even opens the cap for her, like he used to do for Sam when they were little.

“Uh, how was school?” Dean asks. Because what else do you ask a kindergartner?

She shrugs. “Okay.”

Fair enough, he thinks. He never liked school much, but he has to keep this conversation going somehow.

“Just okay?” he asks.

“Yeah. I don’t like math, but Music was fun. We’re learning how to play the recorder. Oh! And I drew Peppa after school. Wanna see?” she says, pointing at her backpack.

Dean raises a brow, but he grabs her backpack off the floor and hands it to her. She unzips it and rifles through her notebooks and her modest collection of crayons. She then pulls out her prized drawing to show him. It looks more like a ball of pink squiggles to him. But he looks harder, and he can see the eyes and the mouth and the nose are close enough to the character on her sneakers.

“Hey, that’s pretty good,” he indulges her, earning her shy smile.

“Thank you,” she says. But her face soon falls. “I wanted to draw her yellow crown, but a boy took my crayon and broke it.”

“Aw, that sucks,” Dean says. Though a smile threatens his lips at the little angry pout on her face. “What did you do when he wouldn’t give it back?”

“I just pushed his arm and he fell and cried,” she says.

Dean blinks in surprise. “Oh.”

Yikes. No wonder you had to go back and talk to Miss Nancy.

“But I didn’t mean to! He was mean to me first,” Emma argues.

Dean shakes his head in amusement, once again tempted to laugh.

“Well, you know, you should never put your hands on somebody. You wouldn’t want him to hit you, right?” he reasons.

The girl considers it, still with that little pout, but she nods begrudgingly.

“See? But if that kid messes with you again, you come tell me, okay? I’ll set him straight, man to man,” Dean says.

She starts to smile again. “Promise?”

“I promise. Let’s shake on it,” he says, giving her his hand. She puts her much smaller one in his, and they shake on it like adults.

“Emma?” your voice calls from outside the office in worry. The door is still open, so you catch sight of your daughter just as Dean tells you to come over. Your eyes grow wide with embarrassment as you realize where Emma ended up. You hasten inside his office.

“What are you doing in here?” you ask her sternly, taking her hand and leading her off the chair. “You were supposed to be doing your homework at my desk. Dean, I’m so sorry. I didn’t think it would take so long.”

“It’s all right,” he says.

You still look a bit mortified and apologetic.

“Seriously, it’s okay. She’s a good kid,” Dean says. You smile, if a bit wryly as you caress her head.

“Well, she wasn’t on her best behavior today, so we’re going to sort that out tonight. But thank you for watching her.”

Dean sends you off with a raised hand, though it turns into a small wave when Emma looks back at him with a sneaking smile.

He chuckles and shakes his head. Kids. Jesus.

She looks just like you.

Five Months

The insistent ring and vibration of your cell phone disturbs your deeply rooted slumber. You slap at the device charging on your nightstand and nearly yank out the cord in attempt to bring the screen to your eyeballs.

Once your bleary vision adjusts to the brightness, you growl in annoyance.

Still, you answer the call.

“Dean. Jesus Christ, it’s three in the morning.”

“I just need your opinion on the new crossbow flame throwers.”

Your sigh can probably be heard across the Atlantic Ocean.

“It’s fine, but it would make more sense on a gun, right? Half gun, half flame thrower.”

“That’s what I said! But Cas says we need to diversify—”

“Dean. Three. In the morning. Go to sleep and let me get back to dreaming about Pedro Pascal as a gladiator, feeding me grapes as his queen.”

“…You like Latin guys, huh?”

You groan and turn your face fully into your pillow.

“Sleeping now. I’ll see you in five hours.”

Six Months

“Look! Emma got first place in the Spelling Bee.”

You pass Dean your phone while he scrapes the pickled onions off his burger and onto your plate. In turn, you give him the pickle wedge off your plate. By now you know that he’s a veritable bottomless pit when it comes to food in general, except for the fact that he doesn’t like pickled onions, and doesn’t trust sushi.

He smiles as he scrolls through the pictures of your daughter’s kindergarten class.

“Clearly taking after her mom in the smarts department. Though you didn’t have to do her like that with those Pippi Longstocking braids,” he remarks.

You scoff in amusement. “Oh, come on, they’re not that bad. It’s not like she’s got a wire hanger in there. She’s just going through a frizzy phase. No matter what products I use, I can’t seem to tame that hair.”

Dean chomps his burger. You’ve reminded him at least 30 times, but he still talks with his mouth full.

“Looks like she’s trying to land a plane,” he says.

You snort, shaking your head. You shove his arm lightly and go back to eating, while Dean takes another look at the pictures.

He sees a lot of you in that little girl. She’s got your eyes, your smile, but she probably has her dad’s hair, his chin. Dean hopes that’s all the girl’s going to get from that fucking deadbeat, biologically speaking. From what you’ve told Dean, all that guy is good for is sending monthly wire payments. After you got your raise, he even tried taking you to court to get his child support reduced.

“Did you want kids—you know, before? Was that even on your radar?” Dean asks.

He doesn’t know what possesses him, but he asks.

You hum in contemplation. “Honestly, it wasn’t. I was focused on my career.”

You wipe your mouth as the thought settles in.

“I thought I’d do it right, you know? Work hard, achieve my goals, find a husband who wanted the same things I did, then build a life, and a family. I always thought I was smarter than a broken condom in the back of his goddamn Lexus,” you say, your tone bordering on disgust at the end. You shake your head and sip your iced tea.

Dean quirks his head. “Well, we’ve all been thrown a few curveballs in life. What matters is how you take it. And I’d say you’ve got the better end of the deal. You get Emma, a good job, the best boss in the world…”

You shoot him a knowing smile.

Dean smirks, but he’s still serious.

“And that guy, all he gets is a life without his kid, and without the woman who could’ve given him a family,” he says. “Sounds like a fucking chump to me.”

He continues eating, but you’re not sure if he realizes how that just tilted your entire axis. It makes you look at him differently, the warmth of admiration in your chest, and something deeper coiling in your belly, stirring up something unexpected.

You stare at him long enough that his brows furrow.

“What? Got something in my teeth?” he asks. 

Your face relaxes, your lips tugging at a smile.

“Yeah, ground beef. Can you please swallow before you talk?”

“This is how I am, sweetheart. Don’t try to change me,” Dean says, taking another massive bite. Oily ketchup dangles from the bun and threatens to stain one of his nicer buttoned-down shirts.

You roll your eyes. “Wouldn’t dream of it.”

You stick a napkin in his collar, just in time for the ketchup drip.

Seven Months

You and Sam have lunch together every Wednesday. It started out as a way to reconnect with your old friend, but it’s often devolved into an hourly venting session about his brother’s many idiosyncrasies, how he’s driving you both fucking crazy, and how to best manage the man’s schedule, as well as steer him away from any half-cocked decisions that could cause a PR disaster.

Like the time he accidentally asked a reporter at a charity benefit why albacore tuna was becoming an endangered species.

“I mean, come on. They’ve literally got fish on the menu tonight. Maybe if you people stopped eating so much damn sushi with your avocado toast, we wouldn’t need this bougie dinner party. $5,000 a plate? Give me a fucking break.”

The fact that he slept with her that night still didn’t save him from the article she published later that week, complete with direct quotes. She had a good goddamn memory.

Today though, your weekly lunch with Sam is less about quasi-therapy, and more about celebrating the fact that Jess is pregnant. You’re even helping her and her sister plan the baby shower.

“Any advice? Just, you know, about parenting in general,” Sam asks. For once, he seems less his normal confident self, and a little more sheepish. It’s sweet, even endearing.

You smile. “God, I don’t know. I’ve been winging it from the beginning. Just…be present, as much as you can. Jess is going to need you to show the hell up, without being asked, without being nagged. You’re the rock she’ll need to lean on, even when she thinks she can do it all while you’re here trying to show up for the job. Especially when the baby’s born. If you’re not covered in three layers of bodily fluids, then you’re not doing it right.”

He laughs a little. “Noted.”

Your mind veers into other directions as you finish up your sandwich and crumple up the foil wrapper. Most predictably, along the road that leads back to Dean.

“Dean doesn’t seem to be the family man type,” you remark. “More married to his work, but…he’s been really good with Emma every time I’ve brought her up to visit the office.”

“Doesn’t surprise me. He basically half raised me after Mom died. More than half, actually. Dad was always working,” Sam says.

“What about relationships?” you ask.

It earns you a certain look from Sam. You’ve come to learn that both Winchester brothers are incredibly sharp, just in different ways. Dean knows how to read people. He’s a good judge of character, and it makes him a shark in the board room, the kind of man that can take in the information his department heads serve him and make swift decisions that often pan out well for HunterCorp.

Sam is perceptive in an almost clinical way, analytical and methodical. He’s the one who can read the data and find the one thing that’s missing. He can anticipate problems before they start, and when it comes to people, Sam often catches the little things, tells and underlying motivations. It gives you away before you’ve even realized it.

“Well, Dean’s been pretty predictable when it comes to women, even before Dad passed,” Sam says.

And it’s true. Dean’s never seen the same woman more than a week at a time. You know this, because you’ve seen the “consolation gifts” he sends them. A Tiffany bracelet. An Apple Watch. Gucci sunglasses. The perfect gift that tells a girl she won’t need to stick around for breakfast.

“But to his credit, he’s up front with them,” Sam says, drawing your gaze. “They know what not to expect.”

Your lips quirk. “Sounds so transactional…and lonely.”

“Yeah,” Sam nods, “but I get it. He took a lot onto his shoulders when Dad died. Right now, Dean’s more focused on making sure we survive than on what he might want. To be honest, I doubt he’s even thought about what that is.”

For some reason, that hits you behind the ribs in a quiet, sharp strike. In your mind, you can’t help but see the familiar tense set of Dean’s shoulders hunched at his desk, eyes glued to his computer while an evening sun sets behind his head.

Even in that big office overlooking the entire city scape, he never has time to admire the view.

Eight Months

It’s your mistake.

Your fingers brush Dean’s for half a second too long when you give him a stack of purchase orders to sign. His eyes meet yours. You point out the new way you’ve color-coded the departments for each PO.

Your heel wobbles on your pivot, an uneven floorboard. Suddenly it’s his hand closing around your wrist and the other wrapping around your waist, giving you stability. Your eyes meet his, heated breaths in between.

A thank you falls from your lips, drawing Dean’s attention there.

But he lets you go.

You walk away, pretending you don’t know his eyes are following you.

You bite your lip against a smile.

One Year

“Seriously, which one?”

“Jesus, Dean. Green! I already told you.”

“No need to get snippy. I just want your opinion.”

“You always want my opinion. That’s why I already laid out the green one for you.”

“But I like the black one.”

“You always wear the black one. The black one says politician. The green one says you’re the boss, but you’re approachable.”

“I don’t want to be approachable. That’s how I get stuck in a 45-minute fucking conversation in the break room with Garth about his side hustle YouTube sock puppet show. That shit was deeply uncomfortable. I just wanted my damn coffee.”

“You know, you could also cut back on the caffeine and the booze while we’re on the subject.”

“Oh, what are you, my mother?”

“You tell me. I’m the one dressing you right now.”

You work the collar dark green suit jacket over his shoulder and smooth down the wrinkles. You firmly ignore how his gaze roams your face, and lower still. You want to pretend you haven’t noticed these signs, all while you try to stop yourself from giving any yourself.

“There, looks good,” you say. Though you make the mistake of meeting his eyes.

He grins. One of those grins that makes you want to grab his face, either mushing it into his seventeen mugs of coffee, or kissing him fucking stupid. You’ve been restraining the latter urge by a tenuous thread for several months now, mostly because you sicken yourself.

He’s your fucking boss. It’s unprofessional. You’ve already been down this road once in your life, and—

“You okay?” he asks.

Suddenly you realize how close he is. You can feel the warmth of his body, you can smell his cologne, and he sounds so sincere in his concern, briefly touching your arm.

You nod, knowing you should create some distance between you and him. Somehow you can’t force yourself to take that one small step back.

Instead, you reach for his tie. “Remember, you’re meeting Frank Devereau and his wife tonight, and Charlie Bradbury. She’s the brains behind the project, so you’ll want to talk to her about the details, how the program works, and how we can incorporate it into our existing tech.”

Dean hums in agreement, but in truth, his attention is on your nimble hands as you work on his tie. You slide the knot up to settle snugly, but not too tight against his throat. You allow your hands to slide down his chest while you admire your handiwork with satisfaction, but your small smile fades. Your mouth goes dry as your gaze travels back up to his, lingering on his parted mouth.

His hands slowly come to hold you by your arms, making your heart tap a syncopated beat.

“Does that look mean you want me to kiss you, or am I just seeing things?” he says at last.

Your eyes widen. You bite the inside of your lip, nervous energy fluttering through you, even as everything within you would like to scream a resounding yes.

“We can’t…shouldn’t,” you say, in a quieter voice. His office door is closed, but it’s not locked. There are far better reasons than that though, and you struggle to remind yourself of each and every one of them.

Dean steals your focus, however. His eyes seem greener than usual, probably because of the jacket. You picked it with that in mind.

“In this case, shouldn’t isn’t a moral argument,” he says. “It’s society’s rules. I don’t know about you, sweetheart, but I’ve never much cared about what people who don’t matter think about me.”

Your brows begin to knit together. “Who matters to you? Because my daughter and my father. They matter to me.”

“Being with me doesn’t hurt them,” he argues, a little peeved at the implication that it would; that he would hurt them, or you.

“Being with you?” you ask in shock.

Dean’s mouth opens, but he hesitates, like what he just said surprises even himself. His lips quirk at a smile.

“I know you, uh, probably think I’m not capable of something like that,” he asks.

“I mean, it is surprising,” you admit airily. Your cheeks warm in a blush. “You could have anyone, Dean…and you have.”

He chuckles dryly. “All right, fair enough. But other than Sam, who gets me better than you? Who else is gonna handle this, the pressure of my life and everything that goes with it…better than you?”

Your eyes widen. A softer smile threatens your lips, because you realize then that he’s actually serious.

About you?

Of course, that’s when your very real, rational doubt creeps in.

“People are going to talk,” you point out. “That’s why shouldn’t always matters. And you and me? Jesus, Dean, this is the oldest cliché in the fucking book.”

His hands move down to your waist, squeezing gently. Enticingly.

“Then we’ll be discreet,” he says, with one of his crooked grins. You shake your head, but you start to smile too. You allow him to pull you back in, figuratively and literally as he bows his head closer to yours.

“You really think you can pull that off?” you ask.

“Sweetheart, with the right motivation, we can pull off anything,” he says, half whispering them on your lips as he captures them with his own.

It’s slow and laced with a curling heat that licks tingles down your spine, just like his hand moving to the small of your back, pressing you into him. Your body betrays you then, with a moan in your throat and your own hands traveling up his arms, over his shoulders, cupping the back of his neck.

The graze of your nails at his nape makes him shiver and groan as he licks into your mouth, holds you tighter. You feel the press of his growing arousal against your belly.

Your good sense knocks at the door of lust and yearning, reminding you that you’re making all the same mistakes again. This isn’t a man you can trust—not with this. But Dean’s lips are hard to ignore, covered in the remnants of your lipstick as he kisses his way along your jaw and down your neck, where he sucks and nips just hard enough to make you gasp his name and writhe against him. He squeezes your ass and smiles against your skin.

“So fucking beautiful, you know that? Even the little sounds you make when I touch you. I wanna find out what that pretty voice sounds like when you come,” he says, in a voice dripped in whiskey and wicked promises.

Jesus. Your heart flutters. You haven’t been touched like this in so very long. You haven’t felt desired like this in…

“How long have you been thinking about that?” you ask, a little breathlessly. He continues his exploration, his lips blazing a sensuous trail down the column of your throat, along the line of your collar bone, and between the rise and fall your breasts. He slides open the buttons of your blouse with a practiced hand, his eyes drinking in the sight of your lace bra.

“Since the day you started wearing these sexy fucking heels,” he says, dragging his hand up your thigh, over your skirt, in a way that raises goosebumps on your arms. But he hesitates. His eyes ask a question as they meet yours.

“You need to tell me what you want though,” Dean says, more seriously than you expected. “You want me to touch you?”

Your heart feels like it’s beating in your throat, but you nod, biting your lip.

“Kiss me, touch me, make me fucking come,” you say. “But first, you need to lock that door.”

A crooked grin spreads across Dean’s face. He steals another kiss before he does exactly that—he crosses the room and locks that fucking door. You lean against his desk for a breather, but you realize that half this shit needs to go. You move stacks of files to the side, the coasters you put for his mugs of coffee along with the empty cups themselves. You push his double-screen monitors forward, giving Dean just the angle he needs to hold you from behind and start laying more tantalizing kisses along your neck.

You sigh and help him with the zipper of your skirt while he works on the bra clasp. The straps loosen down your arms, and he flings the bra away so he can get a handful each of your breasts. You moan and rest your head against his as he begins to squeeze and tease, gently twisting your nipples between his fingers. He leaves open-mouthed kisses against your jaw, sucking at your pulse point.

When his hand moves further down and slips behind the waistband of your skirt and panties, he feels your pulse flutter and trip along with your gasp. His fingers dip between your folds and find the slick mess of your arousal.

“Goddamn, baby. Soaked for me already,” he teases.

You don’t need to see his face to know that smug smirk is plastered across it. You reach back and tug sharply on his hair.

“You can gloat, or you can fuck me,” you retort.

He chuckles and kisses your temple. “Don’t you worry. You’re gonna have to bite down on my belt to keep from screaming in a minute.”

His hand that never left your breast begins to strum the hardened, sensitive nub, at the same time his other hand finds your clit. You shudder against him at that first touch, that perfect moment when you realize he knows exactly what he’s doing as he learns your body. He circles your clit slowly, but with a delicious pressure until it swells under his fingertips.

Then his long fingers dip down into your needy channel, making you whimper as you hold onto him and the desk for stability. His fingers pump smooth strokes inside you, almost as deep as he plans to fuck you with his cock.

He knows he has you when his fingers curl and brush deliberately against that perfect spot inside your inner walls. Your thighs begin to shake, your breaths labored, your hips bucking against his hand in a quiet plea.

Your orgasm rolls swift and steady against his fingers. Your pussy flutters around his hand, and he groans along with you.

“Good girl. Can’t wait to feel that squeeze around my cock,” he says, a filthy whisper in your ear.

You laugh a little, nodding in agreement. You turn around to help him with his belt.

“Yeah, right now. Want you inside me before we run out of time. You have to meet Sam downstairs soon.”

It’s another work event Dean can’t get himself out of, even if the networking opportunities are good for the company.

“You should come with me,” he says, grinning at the way you slide his jacket off his shoulders, but you toss it as carefully as you can across the nearest chair. You just had it drycleaned this morning.

“What?” you laugh. “Dean, you don’t need me there. I’m just an assistant—”

“No,” Dean says, stilling your movements when his hand cups your cheek. Your lashes raise as you look up at him, finding him serious again. His gaze roams your face, his thumb brushing your lower lip. “If it ain’t fucking obvious, you’re more.”

Your mouth falls open, but you’re not sure what’s going to spill out. Dean doesn’t give you time to figure it out, or even let himself settle into his own admission.

He just kisses you, hard and thorough, knocking any more doubts out of your mind, and any deeper thoughts out of his.

He grabs you up by your hips and seats you on his desk, rattling the surface. Your arms wrap around his shoulders on reflex. You feel the muscles flexing under his dress shirt—a crisp black. You help him yank up your skirt and kick off your panties, though they get tangled around your ankle. His slacks and boxer briefs end up coiled around his knees, just far enough to give him room and leverage to slide into your heat.

You both moan at the feeling of him settling snug inside, bottoming out, his almost bruising grip on your ass. Your thighs are wrapped almost as tightly around his waist as he lays you out more fully on the desk. It’s probably harder to do it this way, instead of him just bending you over the hard mahogany. But you’re glad you get to see his face, get to run your fingers through his hair and share his breaths while he fucks you in a slow-rolling rhythm.

It’s more intimate. It feels like it means something, especially when he once again cradles your cheek and brushes wild strands of hair away from your face. Especially when he kisses you deep enough to taste the Almond Joy you snacked on earlier.

You kiss him back just as fervently, as if this will be the first and the last time. You have no idea what happens after today, and you know that probably makes you a fucking idiot. It could lead to the end of your second chance at a career, but you want to trust this. You want to trust the steadiness in Dean’s hands and the look in his eyes.

So you give into what you want, sitting up to lay nipping kissing along his prickly cheek and neck, sucking your own marks against his skin. The way he groans and shudders and fucks you harder—it makes you feel powerful.

“Lean back, sweetheart,” he grits out. “Touch yourself for me.”

You manage to follow his lead, shakily laying back down and letting your hand drift back down your body, finding your clit. Dean watches you play with yourself, his fingers flexing against your hip. You feel him so deep, so good, that the coil of pleasure in your lower belly begins to tighten in earnest.

He’s only satisfied when you have to smother your own mouth against a cry, your hips snapping up to meet his as your release finally hits. Another few ragged strokes, and he spills into you as well.

“Fuck,” he groans into your neck, catching his breath. That was awesome.

But then, his eyes widen. “Christ, forgot a condom.”

“I’m on birth control.” You breathe out a laugh as you soothe him, caressing his shoulders.

He blinks, then he relaxes, chuckling faintly.

“Guess you just make me lose my head,” he says.

“It’s okay. I’ve gotten used to doing the thinking for you,” you tease, biting your lip.

Dean stares down at you, brows raised, yet amused at your cheek.

“Hmm, I’m gonna remember that one. Might have to punish you tomorrow,” he remarks.

You smirk, though a blush burns down your neck at the idea, and the depths of his voice.

He withdraws from you with a quiet moan, then helps you up with a steading grip on your arms when he feels that you’re still a bit shaky. After pulling up his pants, he finds the paper towels you keep handy in one of his desk drawers for the cleanup.

“Seriously, come with me tonight. I’m sure you’ve got a nice dress. If not, I’ll buy you one on the way,” he says, as you two start to pull your clothes back on. And in your case, find your bra.

“Dean, I need to take Emma home,” you say.

You pause with your fingers poised on his dark green jacket, ready to smooth down any wrinkles. The color matches his slacks perfectly. His hair is a bit messy, but overall, he looks edible and professional at the same time. He’s ready to shmooze with the heads of conglomerates and Silicon Valley tycoons and the politicians they own.

But you know you’re not a part of that world.

“Maybe next time,” you say, though you don’t really mean it. Your hand falls.

Dean nods, but he catches your hand before you walk away from him. He slowly winds you back in and kisses you thoroughly enough to make your knees buckle, just a little.

You’re still not sure if he meant what he said about wanting to be with you, or if this is just something he’ll change his mind about in the morning after a few glasses of whiskey.

You definitely think about more than just the road ahead while on your way home, Emma’s chatter filling the car. For once, you can’t say you’re fully paying attention.

Your fingers keep touching the memory lingering on your lips.

AN: 😘❤️‍🔥 How'd you like the slow build? lol Did Dean's earnest appeal surprise you there at the end? He's been a pretty successful play boy up until now, but he's really going to prove himself in Part 3 of our adventure, set shortly after Pratt Fall.

Next Time in Nothing by Halves:

Dean finds a guest spot in front of the school. The old Impala rumbles to a stop there, and he climbs out, grabbing the bouquet resting in his passenger seat.

His keys jangle in his other hand as he makes his way to the front office to check in, just like you told him to in your texted instructions. The nice ladies there give him a guest badge that he slaps on his chest, over his dress shirt, and they tell him how to get to the theater. He feels awkward and out of place walking down the halls of this school alone, but you had to take Emma over there early before the show. 

The hell am I doing here?

He has to fucking wonder.

But he promised you. He promised the kid. So he’s here.

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You really crafted the beginnings of their relationship so well to go from Dean being a (slight) bit of douche to respecting her, becoming friends, to letting those feelings manifest and then fester.

“Have sex with me-“

“Yeah, I- I heard you the first time, that’s not-“ Dean shakes his head, running a hand over his face. “It’s eight in the fuckin’ morning-“

“It’s eight fifteen.”

That earns you a flat look, and you smile innocently.

“That’s fifteen extra minutes, it matters-“

“Not for this. And- I ain’t even showered yet-“

Your nose wrinkles. “Why haven’t you showered?”

“I shower after coffee,” Dean mutters, turning his mug in his hands. “If I don’t, Sammy’s stinkin’ up the kitchen from his run.”

“Oh- Okay.” You clasp your hands behind your back, peering at his tight jaw, his mussed, soft-looking hair. “Is that… A yes?”

Dean’s eyes widen on yours. You’re worried he’s going to choke on the air this time. “Yes?”

“Are you going to have sex with me,” you clarify, and his mouth falls open.

“I- I’m- You’re-“ His throat bobs, and he starts to look around the room with a worried squint. “Are you fuckin’ with me?”

You frown. “Why would I be fucking with you?”

“’Cause, sweetheart, you can’t just-“ He lets out a sharp breath. “Is it Sam? Did he put you up to this? ‘Cause I told him- That kinda prank, it’s off the table-“

“What kind of prank?” You’re a little lost, and there’s shame starting to burn up your neck.

A prank. He thinks it’s a prank.

It’s not. You’re so serious it’s almost embarrassing. You wouldn’t have asked him if you weren’t. You’d almost talked yourself out of it, after spending too much time convincing yourself into it. Nights of tossing and turning in bed, an insatiable and aching heat between your legs and the sheets bunched around you in a mockery of a body. Weeks of watching the boys slip out of bars with women that seemed to fall into them like magnets while you spun around, alone on a barstool without any prospects.

Months, of watching Dean with a flush he never saw. An adoration written all over your face he didn’t seem capable of noticing. You’d tried to stomp it out. Your stupid, useless little crush. Dean was older. Seasoned and desirable in the way that made you wonder if he was even real sometimes. Out of your reach, tantalizing, and impossible to just forget about. 

You’d neglect your feelings in the hope they’d die, but he’d water them until they were in full bloom and overtaking your heart and mouth and head. He’d buy the snacks you like and let you chose the movie. He’d open doors and let his hand linger on your lower back, he’d smile at you in the dim light of the Impala and make you feel like the only person in the world, he’d call you when he was away on a separate hunt every single night, just to update you. He’d play wrestle you for the remote, and somehow never manage to wonder why he always won when he’d see you take down men closer to Sam’s size with barely a grunt of effort.

“Nice try, sweetheart,” he’d whisper in your ear, when he had you pinned on the floor beneath him, and you’d have to swallow down your moan.

He’d get up, turn on the TV, and leave you on the couch while he went to the bathroom. You’d sit with your knees to your chest and your breathing uneven, unable to focus on anything but the ghost of his body over yours. The heat of him, the way his arms had caged you in, his knee pressed far too close to your neglected core.

If Dean knew how you dreamed about him—how those moments followed you into bed, every single night—you’re so sure he’d never look at you again. He doesn’t see you like that, you’re sure. You’re the kid they took in, the annoying girl who’s got too much mouth on her and not enough experience, in every possible way.

You’ve never done sex. You sort of just missed the window, where it’s supposed to happen, and then it became too big a deal, then you met Dean and you were lost. What was the point of being with anyone else, when you had his shoulder bumping yours in the hallway. When you were so hopelessly in love with him, you think your heart might beat out of your chest like a cartoon every time you see him.

So you made a choice, a few weeks ago. A choice it took a lot of courage to work yourself up to following through on

You just need to have sex. With someone. Anyone. Preferably Dean. It just needs to be done and over with—one time, where he doesn’t know he’s taking your virginity, where he’s peacefully oblivious of your worship of his very existence—and then you can try to move on. Once you’ve had sex, it won’t be this big monster you shy away from anymore. It’ll just be another thing.

So you’re asking Dean. Outside of your alternate motivations, it’s a sound strategic call. You know about his prowess. He’s bragged to you about all his five-star reviews. And maybe that always made you gag over a toilet bowl after, but if it did, that’s none of his fucking business.

Maybe you’re not up to par with his usual partners, but you can do your makeup, or he can turn off the lights, or whatever else makes it easier for him. Anything that makes him touch you. You won’t even cry about it in front of him.

But he thinks it’s a prank. Why would he think it’s a prank.

“You know,” he says, watching you wearily. “Sammy gives you a tenner, you come and ask me for sex, everyone gets a good laugh at Dean. Good joke. Classy.”

You wrap your arms around your stomach, shrinking slightly into yourself. “It’s not a joke,” you mumble. “I- I was serious.”

“You were serious?”

He says it like it’s insane. You shrug, fixing your gaze on the floor. A joke. He thinks fucking you would be a joke.

“Sweetheart-“

“You don’t have to,” you take a step back, trying to sound casual. Like your heart isn’t being torn to ribbons.

You really hadn’t expected him to leap at the opportunity, but this is so close to cruel it hurts. Tears are threatening your eyes, and a lump is forming in your throat. Pathetic, a voice spits in your head. Why the fuck would he ever want to fuck you.

“Wait, just- Hold on-“

You look up, faster than you want to admit. Dean staring at you with pale face and slack jaw, throat working like he’s swallowing his own words every second. You wait, because you’re a fucking useless idiot. Bouncing nervously on your feet—they’re smarter than the rest of you, they want to run—and trying not to melt under his gaze.

“You’re actually askin’ me to fuck you?” He rasps, and you nod.

It’s the tiniest motion of your head. Dean shifts in his seat, staring at you with wide, dark eyes.

“Why?”

“Why?” You frown, saying the first, easiest, least embarrassing reason that pops into your head. “Because- You- You’re good at it?”

“I’m good at it,” Dean repeats. “You wanna fuck me ‘cause you think I’d be good at it?”

You wish he’d stop saying fuck like that. With a harsh ending and low drawl. “I don’t think,” you offer. “You’re the one who said you would be.”

Dean’s lips twitch, but he doesn’t look amused. “I could be lying, sweetheart.”

“I don’t think you are.”

He stares at you. His eyes flick up to the ceiling—maybe he still thinks he’s on a prank show—and he lets out a sharp, slow breath from his nose.

Then he shakes his head, and you feel the echo of your heart as it howls in pain.

“No,” he mutters. “I ain’t- Doin’ that. Not just ‘cause you- No.”

You blink at him, the world blurring a little. You stumble back, and Dean says your name, moving to his feet. You shake your head, moving back another step. Your eyes are stinging with tears, but that’s not his problem. He’s allowed to reject you. You’re also allowed to cry about it.

“Sweetheart-“

“It’s fine.” Your voice is too high. Too wobbly. “It’s- That’s okay.”

“No, just- Fuck-“ He rubs his jaw. “Listen to me, alright-“

“You don’t have to explain,” you shrug weakly. “It’s okay.”

Dean gives you a disbelieving look, but you move further back before he can try to make you feel better about the rejection. It’s not going to help.

“I’ll just-“ You look over your shoulder. To the door, just one more step back.

Dean says your name again. When you look back, he’s reaching to you, trying to beckon you back into the kitchen. You smile, tight and watery.

“Thank you for your consideration.” You say, because you’re a fucking idiot. Dean certainly looks at you like you’re one.

You flee the kitchen. He calls your name again, but this time you don’t look back.

Rejection is fine. You’re fine. You’re so fine, you lock yourself in your room for the rest of the day and eat so much ice cream your stomach hurts. Because it’s fun. It’s fun to cry over something you never even had.

At least you anticipated this. You have a very solid plan B.

If Dean won’t sleep with you, you’re going to find someone who will. You’re going to get it over with. This week.

You’re learning something about yourself.

You are not good at flirting.

The first thing you try is the bars. Sam and Dean slide into a booth, and you go to get the drinks. A guy makes eyes at you, and you smile sweetly in return. When you bring the drinks back, you set the beers down in front of the boys and turn back on your heels to give the bar-guy a shot.

Dean says your name, and you freeze. You always do that for him. It’s a habit you don’t think you’re able to break.

“Where’re you going?” He frowns at you, one arm slung around the back of the seat. Around where you’d usually sit.

“Bar,” you say lamely, and the lines on his face deepen.

“Why, you forget something?”

“No.”

“Then what-“

Dean cuts himself off, his gaze flicking over your shoulder. To the bar. To the man, waiting for you with a smirk, because you promised you’d be back.

Dean grunts your name, low and rough, and if he asked you to stay, you don’t think you’d be able to tell him no.

Things have been strange, since the kitchen. Neither of you have brought it up, and Dean hasn’t stopped treating you the way he always has, but there’s something charged beneath it. A live wire that frays and crackles, every time your fingers brush or your eyes meet. You’ve caught him staring at you with an open mouth a few times. Last week he tried to talk to you, alone in the Impala while Sam got snacks from a gas station. You announced that you had to shit, and scrambled out of the car.

You don’t want to talk about it, and Dean has no right to make you. He’s not the one who got his heart broken. He’s not the one who sort of wants to cry, whenever your eyes meet.

He certainly has no right to glare at you, when he puts together what you’re doing. He said he wasn’t going to sleep with you, and you’re a grown woman. You can, if you so please, have casual sex with a stranger. It is your right.

“You can’t be for real, sweetheart-“

“Dean.” Sam stares at his own beer, looking like he wants to vanish into the floor, and Dean scowls.

“C’mon, Sammy- Tell her she’s being crazy-“

“Crazy?” You snap, and Dean leans back in surprise. “You fuck around all the time, how is it crazy that I’d do the same thing?”

“It’s not- You just- You don’t-“ He swallows. “You don’t do this-“

“I do now.”

“Sweetheart, just- Sit down-“

You flip him off, and march back to the bar before he can ask with a little more conviction. You just need to break out of his orbit. To force yourself to realize that there are plenty of other men, and not having Dean isn’t the end of the universe.

Unfortunately, you sort of just keep proving the opposite.

“What’s a pretty little thing doin’ in a place like this?” The first guy at the bar asks, and you fumble.

You have no idea. You giggle nervously and spin in your chair, speaking words you can’t really hear. He seems into it—no matter how pathetic you must be coming off—until his fingers brush your arm, and you flinch back because his skin is cold. It sends a shiver up your spine that’s not the hot rush of Dean’s touch, but the sliver of a snake.

You go home alone that night, and you don’t look Dean in the eyes. He tries to talk to you, before you retreat to your room. You ignore him, because that’s the only way this is going to work. 

But you try again and again and again, and you never get anywhere. They always touch you, and it all falls apart. You look at them too long, and you can’t manage to squeeze them into a Dean shaped hole in your heart, and there’s no way forward. You try dating apps. That goes worse. Every dick pic you get sent just makes you wonder if sex is even something you want. They’re all worm-shaped and ugly. At least dildos come in nice colors. Maybe you should just buy a dildo.

No. You’ll just pretend it’s Dean all the time, and that’s the opposite of what you’re supposed to be doing here.

So you keep trying. And you keep failing. And Dean’s been looking at you weird—brow pinched and jaw set, every single night—and you’re getting desperate and fuck it.

“Sam.”

Sam hums, not looking up from his book. You clear your throat, leaning further over the table.

“Sam.”

“I’m listening, what’s-“

“Have sex with me.”

Sam, to his credit, doesn’t choke. He just goes very, very still, and looks up at you with an expression close to horror. He says your name slowly, and you shake your head, holding up a single hand.

“Just- Listen-“

“No?” Sam gapes at you. “I’m not- I’m not going to listen to that- Jesus Christ-“

“Come on, we could turn off the lights, and- I wouldn’t make it weird-“

“It’s already weird-“

“You’d be doing me a favor-“

“I’d be making a death wish!” Sam’s voice drops to a hiss. “Dean would fucking kill me.”

 You roll your eyes. “Then don’t tell him, dumbass.”

“No, I- I’m not doing that.” Sam shakes his head, like he’s trying to jolt the image free. “To you. Or him.”

“To him?” You narrow your eyes. “I- What the fuck would this do to Dean?”

Sam gives you a puppy-eyed, hopeless look. “I… Can’t say.”

“Sam Winchester-“

“Why are you asking me?” Sam whines. “I’m not- You’re not even into me-“

“Exactly, there would be no strings attached-“

“That’s not healthy-“

“Fuck off, like you don’t have casual sex-“

“I mean, I do, but I’m not-“ Sam cuts himself off, sighing dramatically. “Just- Why would you even want to have sex with me?”

You flush, but shrug. It’s just Sam. It’s easier to tell him than Dean. “I want to get it over with.”

“Get it over with?” Sam echoes. “It- You mean sex?”

You nod, and Sam blinks.

“Are you a virgin?”

“Maybe.”

“You- You’re-“

“Don’t be an asshole-“

“No, I’m not- I mean- It’s fine. It doesn’t matter. It actually-“ Sam frowns at the air. “It makes sense, I guess.”

That makes you scowl. “It makes sense?”

Sam shrugs, giving you an apologetic smile, and you can’t even think of an argument. You sigh, your shoulders slumping, and Sam clears his throat.

“You know I’m not going to sleep with you, right?”

“Yeah.” You sigh, and he nods slowly.

“Does Dean-“

“No.” You point a stern finger at him, and Sam raises his hands in surrender.

“I think you should-“

“Sam. I’ll cut your balls off.”

“I- Okay.”

You give him one last glare, and go to leave. But before you can go, the question scratches up your throat. You turn around, hands tucked behind your back, and speak softly. “Would you?”

Sam blinks. “What?”

“If you didn’t- Know me,” you mumble. “If we weren’t like- Friends. And you just met me, and I asked you- Would you?”

Sam snorts, and you scowl.

“I’m serious-“

“Yeah, I know you are.” Sam’s lips twitch. “It’s just- Yeah. I would. Of course I would.”

You stand a little taller. “Really?”

“Yeah, I mean- You know you’re attractive, right? If you just didn’t, like, annoy me. I’d be in.”

“I do not annoy you-“

“You’re annoying me right now.”

You laugh despite yourself. Sam smiles, his voice dropping to something gentler.

“Anyone would be lucky to have you,” he says your name slowly. “I just- Don’t want to be lucky.”

You huff in amusement—if Sam isn’t lying, aversion to luck is a family trait—but dip your head. “Thanks. I think.”

“You’re welcome. And-“ Sam pauses, looking you up and down with a strange expression. “I’m sure the whole- Thing will work out for you. There are… People. I think you’re going to figure it out.”

“You need to sleep with her.”

Dean needed to stop drinking coffee when people walked into the kitchen. This was the second shirt he’d ruined in as many months, and it was because everyone kept saying crazy fucking shit.

“Sammy, what the fuck-“

Sam said your name, and Dean’s hands fisted on the table.

Again. Son of a bitch, he was about to go through this again. The first time had been bad enough. You’d looked at him with glossy, hopeful eyes, practically begged for him to fuck you, and Dean had wondered if he’d died in his sleep last night and been dragged back to hell. Forced to experience some new kind of torture Crowley was developing, where everything he’d ever wanted was just a stretch away from his fingertips, and he wasn’t allowed to take it.

He had to be the noble one here. The wise, old asshole who didn’t take advantage of you. Taking you up on that offer would be one of the worst things he’d ever done. It would be selfish, and cruel, and a worse fate than anything else. To get what he wanted, for one night, then never fucking have it again. To get hooked—because he would, he fucking knew he’d never be able to kiss and touch you once then go back to just living—and turn into an addict willing to do anything to get another hit.

Dean would’ve turned into a bigger creep than he already was. Instead of stares and long, shameful showers with his cock in his hand and your name on his lips, he’d stuff your panties in his pocket and press them to his nose while he fucked himself raw. He’d get possessive, he’d snarl at anyone else who got to close, he’d fall to his knees and beg you to stay if you ever decided you had enough of him.

And he knew that last thing was going to happen eventually. You had a whole life ahead of you, and he was stuck here. In this dim bunker with blood on his hands and under his feet and staining his past and future all at once. He swam in a river of it. In front of him, behind him, washing over him all the time, there was just fucking blood. You deserved better than that. Better than Dean. You deserved the fucking world.

So he’d told you no, and you’d looked at him like a wet fucking kitten he’d kicked into the rain, but it had been for your own good. You’d get over it. Dean was the one who had to watch you flirt with douchebags at the bar. Who couldn’t get in another bed anymore, because he kept getting kicked out for moaning your name.

He was the one who was rooted here forever. You’d find something softer. Something good.  He’d accepted that, with a lot of beer pushing it down. You’d find something better, and that was what he wanted.

Sammy knew all that. Dean had gotten drunk once and confessed his stupid, undying feelings, then sworn Sam to secrecy in the morning. He’d kept his word, only shooting Dean sad looks whenever you went off to flirt and smirking whenever Dean called you on a hunt.

But now he was asking Dean to sleep with you. Like he’d lost his damn mind.

“No,” he grunted, and Sam rolled his eyes.

“Look, Dean, I get that you’re being cool and righteous and whatever-“

“I’m not fuckin’ her, Sammy- I shouldn’t.” He shot Sam a glare. “You know why I shouldn’t.“

“Yeah, well, I think your why is pretty stupid.” Sam said flatly. “You’ve never even asked her if she’d be- You know. Open to it-“

“I know she’d be open to it,” Dean scowled at his coffee. “But that’s- I ain’t doing it, Sammy. Never.” Not like that.

Sam was silent for a moment. When Dean looked up, he was staring at him with wide eyes. “She asked you first, didn’t she.”

Dean frowned. “What’d you mean, asked me first-“

“To take her virginity.”

He hadn’t taken a sip of coffee again. This time, he managed to choke on nothing at all. “To- What?”

Sam leaned back slightly. “Did she not ask you to sleep with her?”

“No, she did, I just didn’t fuckin’- She’s a virgin?”

“I guess,” Sam shrugged. “You know that’s not a big deal, right?”

Dean grunted. His head was spinning. Of course it wasn’t a big deal, he didn’t care. He’d wanted you before, he wanted you now, that wasn’t the fucking issue.

But you’d asked him.

You’d asked him to fuck you. You’d wanted him to- Do it. Take it. Pop it, whatever. You’d chosen Dean, to be the guy, and he’d told you no, and then you’d started flirting around with other people, and you could’ve ended up with someone dangerous, someone who took advantage of you, who thought your inexperience was hot for all the wrong reasons and hurt you and-

Dean paused. He looked at Sam. Sam blinked, and Dean’s eyes narrowed.

“How the fuck do you know that.”

Sam swallowed, taking a small step back. “Uh…”

“Sam-“

“She might’ve… Asked me.”

“She what-“

“I said no!” Sam said quickly. “I told her I wouldn’t. But- You know.” Sam cleared his throat. “If you’d said yes to her the first time…”

Sam gave him a pointed look. He was asking to get punched in the fucking face.

“No.”

“Dean, just-“

“No. I’m not takin’ advantage of her, Sammy, I’m not-“

 “It’s not taking advantage of her if she wants it!”

“She doesn’t want it-“

Sam snorted. “Oh, fuck off.”

Dean blinked, leaning back in his chair. Sam turned a little red, wincing at himself, but didn’t back down.

“Wow, Sammy. Big claws, huh.”

Sam sighed, running a hand over his face. “Dean… Just- Think about her, okay?”

Dean almost laughed. “All I fuckin’ do is think about her-“

“Then think a little harder.” Sam said flatly. “Before both of you get actually hurt.”

Dean didn’t have an answer to that. Sam didn’t seem to be asking for one. He turned and walked out of the room, leaving Dean alone. With only his coffee mug and thoughts for company. A dangerous thing to do. Dean could talk himself into and out of almost anything, if the logic police weren’t there to stop him.

He was going to do something really fucking stupid and selfish, and it was all Sam’s fault.

“Come in!” You call to the knock on your door, glancing up from your laptop as the door creaks open.

Dean shuffles into your room with his head bowed. Your face heats, and you slam the laptop closed. He doesn’t need to see you scrolling through hookup websites and think any lower of you. You’re already losing sleep over the worry you’ve fractured something between you beyond repair.

“Hi,” you whisper, and he swallows.

“Uh- Hey.”

“Hi.” What the fuck is wrong with you.

Dean’s lips twitch. “Hey.”

You start to pull the sheets between your fingers, trying not to ogle him too obviously. He’s wearing sweats and a t-shirt, and it’s sexier than all the profile pics you’ve spent hours staring at. His hair is a mess, and there are bags under his eyes, and you don’t think you’ve ever wanted to climb over him more.

“You, uh-“ He glances at your computer. “You busy?”

“No- No.” Never for him. You shove your computer onto your bedstand, moving to sit on your knees. “What’s up?”

Dean’s throat bobs. He runs a hand through his hair, huffing something close to a laugh, and shakes his head. “Jesus.”

“What-“

“Nothin’.” He clears his throat, giving you a strange look. “Did you ask Sam to sleep with you?”

Your mouth falls open. You almost trip sitting down. “I- I didn’t-“

“You didn’t?”

“No, I mean- I- He wasn’t supposed to tell you,” you whine, avoiding Dean’s stare. “I didn’t- Fuck-“

“Hey- It’s- Woah-“

Dean crosses the room in a few strides, grabbing your wrists with firm, warm hands. You’d started to pick at your nails with the anxiety. You hadn’t even realized it.

“Don’t hurt yourself, sweetheart,” he mutters, his thumb dragging a circle on your wrist.

You nod, your voice only a breath. “Okay.”

He’s so close. You can count all his crow’s feet, map his stubble, trace his lips with just your eyes. He’s still frowning at your wrist, so you allow yourself to stare.

Then he looks up. And you freeze in panic, but don’t manage to look away.

Dean’s tongue flicks over his lips. Your breath catches. Neither of you move, and you let yourself have it. For a single second, you imagine that Dean is here, in your room, on your bed, and that means something. You get lost in the warmth of his proximity, the calloused but soft feeling of his touch.

“Sammy told me something else,” Dean mutters, scanning over your slack, flushed features.

“Yeah?” You whisper, and he nods tightly.

“Yeah. Said you’re, uh-“ He clears his throat. “Said you’ve never- You know.” He cringes. “Been fucked.”

Your mouth falls open. You think you’d like to die now. “Dean-“

“Is that why you asked me?” His grip tightens on your wrist. Not allowing you to pull away. “’Cause you just wanted someone to take it?”

You drop your gaze to his crotch. There’s a soft bulge there. You’d drool over it, if you didn’t think you were going to explode any second now. 

Dean says your name, and you shake your head.

“Don’t,” you mumble. “Don’t just- Feel bad for me- You said no, that’s- It’s fine-“

“What if it’s not.”

Your eyes shoot up. You’d think he was joking, if he didn’t look so fucking serious. His jaw is set. His eyes are blown out and fixed on yours. Your mouth hangs stupidly open, and Dean smiles softly.

“Huh?” You manage to choke out, and he almost chuckles.

“What if I wanted to. Help you.”

“But-“ You blink. “You don’t.”

Dean shakes his head. “Wrong, sweetheart. I do-“

“You said you didn’t-“

“I lied.”

You stare at him. He doesn’t back down.

“Would it mean something?” He muttered, reaching up to trace the curve of your cheek. “If I did it?”

You nod weakly, leaning into his touch. It sends violent, hot shivers through your whole body. Almost like a fever. You don’t want the cure. “Would it matter to you?” You ask, and Dean’s eyes flash. His fingers curl on your cheek. He leans an inch forward, then another inch. Your lips brush, the lightest possible touch, and you let out a soft, uncertain whine.

Dean pushes forward, his lips fully crashing into yours, his kiss demanding but certain. He presses over you, pulling you a little further up on your knees. You grab the collar of his shirt for balance, squeezing your eyes shut and trying to kiss him back with as much fervor as he’s offering you.

“De- Dean-“ You gasp against his lips. “Dean-“

He groans, his arm sliding around your back so he can pull you tight to his chest. You melt into his arms, and his kisses turn messy. Open mouthed and rough, his tongue dragging over your teeth as his fingers dig into your hips. You run out of air fast, but don’t try and pull away. You don’t want this to ever end, and you’re afraid that if you dare to break the moment, it will never be repaired.

High gasps start to escape your throat, though, and Dean pulls away. He cups your face between his hands, frowning slightly, and presses his brow against yours. You struggle for air, almost pressing forward to try and kiss him again, but he holds you in place.

“Breathe, sweetheart,” he mutters, rough and thick. It’s the same voice he uses on you during hunts. When he’s giving an order you didn’t ask for.

Usually, you protest or ignore him. Right now you’re putty in his hands. He could tell you to follow him to hell, and you would. You’d do anything, just for him to never let go.

You inhale unevenly, and Dean rubs your upper back. His hand slipped under your shirt, and his palm is broad and warm. It—annoyingly—helps a lot.

“There you go,” he murmurs, watching you under hooded eyes. “That’s a good girl.”

You whine again. “Dean-“

“Sorry. Couldn’t help it.”

He doesn’t fucking look sorry. His lips are twitching, and there’s a smug glint in his eyes that’s almost dangerously intoxicating.

“Better?” He asks, and you nod, slumping closer to his chest. He doesn’t push you away.

This might be real.

“Are you sure, ‘bout this?” Dean rasps, and you almost giggle.

“Yes.”

“I’m old, sweetheart-“

“I like it.”

Dean blinks, and you stutter, so sure you should shut up but not really sure how.

“I- I mean- I like you, so- I don’t care if you’re old- I like you old- I like you-“

Dean smirks, holding your face so firmly against his  you can’t shy away.

“You- Can you- I mean- If it’s just- Just sex- You can forget I said- I think you being old is hot-“

He finally takes mercy, and shuts you up with a long, rough kiss. You hum, pushing further up on your knees, and climb slowly into Dean’s lap. He sucks on your lower lip, angling your head back as your core settles against his bulge, then pulls back with a low sigh.

“Not just sex,” he mutters, dragging his thumb over your swollen lower lip. “Not with you, baby.”

You nod, smiling wider than you probably should. “Cool.”

Dean grins back. “Yeah?”

“Mhm.”

“Cool ‘cause you like me,” he teases, shoving your hips down, right over his crotch. “Of ‘cause I’m old.”

You face burns. All you can do is stare and him and whimper, “You’re spritely.”

Dean huffs, in disbelieving amusement. “Spritely? You think I’m-“

“Youthful,” you babble quickly. “You’ve got a lot of…” You flush as he stares at you, sort of wishing he’d just kiss you and shut you up. “Youth.”

Dean’s mouth curves up. “Youth, huh.”

You nod, and he chuckles, pressing the lightest kiss over your lips.

“Hurts when I bend over now, honey, don’t think that’s very youthful of me.”

“So don’t bend over,” you mumble, and Dean snorts.

“Demanding, aren’t we?”

You shrug, trying not to turn into a puddle and miserably failing. Dean kisses your cheek, then under your eye, tracing his mouth down so he breath tickles your ear.

“Mouthy and demanding,” he rubs your hips, dragging your hips back and forth across his crotch. “Don’t worry. I’m gonna fix that.”

You whimper, and Dean’s grin grows.

“You like that, huh.”

“Dean-“

“Ah,” he kisses the corner of your mouth, moving away before you can chase his lips. “You wanted my help. This is how I’m gonna help, baby. Takin’ real good care of you,” he thrusts his hips up, and you whine as the hard outline of his cock hits your clothed pussy. “Just like this.”

 You nod, pressing your face into the crook of Dean’s neck. You don’t think you’ve ever been this turned on. It’s different, with Dean’s hands wandering your sides and his voice right in your ear. Your heart pounds and everywhere gets slick with sweat and arousal, just his dirty talk reducing you to a heap of confused nerves. Dean’s lips drag over your jaw, and you curl further around him, your nails digging into his shoulders as he nips at your throat.

“Just gotta do what I tell you, alright?” He mutters, squeezing a handful of your ass. “Can you do that, baby? Do it for me?"

You nod quickly, and Dean chuckles against your skin.

“Eager,” he drawls, pushing his fingers slowly under the hem of your shorts. “Eager and soft.”

He squeezes your ass again, his fingers brushing against the edge of your pussy. You grind backwards, trying to push him to where you need him so very desperately. He lets you, teasing his fingers over the lips of your pussy, and you whine in his ear.

“Sit still,” he grunts, and you have to bite your lower lip, but you force your hips to come to a stop.

It earns you a sharp slap of your ass, and a kiss on the side of your head. Worth it.

“That’s right,” he mutters, letting those thick fingers dance back over your cunt.  “Good work, baby girl. You fuckin’ love the attention, don’t you. Eager to please me, eager to make me proud.”

You swallow, hugging him so tight you’re a little worried you’ll choke him. Dean doesn’t even flinch. He dips two fingers into the wetness of your heat and groans right in your ear, spreading the arousal everywhere between your thighs.

“If you’re gonna hide that pretty face,” he grunts in your ear. “At least fuckin’ kiss me.”

Nervously, you wander your lips over the strong curve of his shoulders, the arch of his neck. Dean moans in your ear, his cock jumping in his jeans. His fingers keep wandering near and around your pussy, and you get a little bolder. Kissing up his jaw, over his cheek, the top of his lip. You’re panting, trying to focus on your job as Dean keeps pulling and teasing you with his touch.

“Shit,” he moans your name, tracing around your flutter entrance. “That’s it, baby, just like that-“

 Dean grabs your jaw with his free hand, like he can’t fucking help himself, and slams his lips against yours. You squeak in surprise, but kiss him back, grinding down onto his hand. His fingers dip inside of you for a moment, and you moan. Dean grunts and shoves those fingers inside of you.

Your mouth falls open, your eyes widening at the thick, pleasurable stretch. He feels so good, so fucking right, you’re worried his cock might kill you.

“Look at you,” Dean coos, smirking at your slack face. “Just my fuckin’ fingers, baby. Keep breathin’, or this is all we’re doing tonight.”

You take a deep breath, sharp and sudden, and Dean smirks in approval.

“Good girl,” he pushes his fingers a little deeper, scissoring them and bumping against a spot that makes your whole body jerk.

“Dean-“

“Shh,” he kisses you, crooking his fingers to rub against that hidden button, and you mewl against his lips. “You feel that, baby?”

“Mmm- Mhm.” You press your cheek against his, eyes fluttering as Dean keeps pushing and tickling deep inside you. “Feels good.”

“I know it does, sweet girl,” he wraps his hand back around your neck, guiding your brow to press back against his. “It’s that special little spot, gonna make everything feel good.”

His words are sweet and mocking all at once, and it sends a new gush of arousal between your legs. You watch him with wide, clouded eyes, and Dean’s smile softens for a single second. He kisses you, more gentle than before, and pulls his fingers slowly out of your cunt.

“Lie down,” he whispers before you can protest, and you swallow, but obey.

Dean hums in approval, rubbing a massive hand on your thigh.

“Everything off,” he says, and you go still.

“Everything?”

“Mhm,” he raises his brows at your flushed expression. “That gonna be a problem?”

You shake your head, wrapping your arms around your stomach. You don’t want to disappoint him, but he’s going to see you. Really, fully see you. God, you really don’t want him to see you and change his mind, and-

“Hey,”  Dean takes your hand, squeezing it gently. “You want my help?”

“Yes, please,” you breathe, and that’s all it takes. 

Dean rips off his shirt first—makin’ it even, he says—then makes quick work of his jeans. You don’t get more than a second to marvel him—flushed, tanned chest and thick everything, and heavy cock that does not look like a worm—before he’s touching you. He shimmies your shorts down, then peels your shirt over your head, leaving you in only your underwear. For a moment he just admires you, palming his cock with a tiny grin, and you roll onto your stomach.

Dean laughs, tapping your ass with a single finger. “Gettin’ shy, baby?”

“Shut up-“

“Ah.” He drags that finger down your clothed pussy. “Who tells who what to do?”

Your face burns, and you press your face further into the pillows. Dean chuckles, and you feel the bed shift as he crawls over your body. You can feel the heat coming off of him, feel the drag of his cock somewhere near your ass as he whispers in your ear.

“You were doin’ so well,” he drawls, unhooking your bra with a single hand. “Don’t get shy on me now.”

It doesn’t help. You keep grinding, trying to get some friction with the sheets. Dean’s hand comes down on your pussy with one, sharp smack, and you squeal, pushing back against his hand.

“Needy fuckin’ baby,” he mocks. “Can’t even help it, can you. Still tryin’ to be good for me.”

He hooks two fingers around your panties, pulling them tight so they push against your clit. You push back against his hand, and he smirks against your ear.

“You want a little more?”

You nod, and he snaps the fabric down, sending a tiny shock through your body.

“Say please-“

“Please,” you gasp, moving your arms up to hide your face. “Please, Dean- More- Oooh-“

Dean’s thumb finds your clit, rubbing in slow, tight circles. Your words fall off, and he fists a hand in your hair, tugging your head back to allow him to kiss you again.

He’s not cruel, with how he touches you. He’s generous, but controlled. Every stroke of your clit is deliberate, making your head spin and your mouth fall further open. That seems to be exactly how he wants you, though, because he pushes his tongue further down your throat and flicks his thumb back and forth, working you up into a writhing frenzy.

When his fingers finally push back inside of you, Dean almost seems unwilling to pull back and stop kissing you. You’re bent back and pliant under him, whimpering happily as he feeds his fore and middle finger into your hole.

“Greedy little pussy,” he rasps against your lips. “Know you’re gonna strangle my cock, baby, son of a bitch-"

He groans, like he’s the one being fingered into oblivion. He’s set a harsh pace with his wrist, snapping his fingers in and out of your cunt without relent. His thumb moved away from your clit, replaced by the heel of his palm, rubbing in tight, unrelenting circles on your swollen clit.

Every single time, he hits that spot inside of you, and your head is starting to get light. All the electricity and heat in your body is pushing down into your core, building like a bomb and threatening to explode. You almost sob, with how overwhelming the sensation is. Dean notices, kissing you a little softer.

“Poor girl,” he mutters. “Already like this and I’m not even properly fuckin’ you.”

“Your- Your hands,” you push out the word between sharp breaths. “They’re big.”

Dean grunts, his cock jumping near your ass. “Yeah, sweetheart? You like how fuckin’ big my hands are?”

“Mh- Mhm.”

You try to kiss him again. He pulls back, moving his hand impossibly faster against your cunt.

“Words,” he grunts. “You’re not stupid enough to not speak, not yet.”

“Like it,” you breathe out. “Love- Love it, Dean, oh- Oh my god-“

You moan again, and Dean grunts. His hips are starting to jerk near your ass, making him rut against you as his fingers work.

“Your close,” he mutters, pressing his fingers fully inside and crooking them against that gooey spot. “Cum for me, pretty girl. Now.”

His voice must have some kind of supernatural power over you, because that pressure in your lower tummy bursts, and your orgasm rips through you link a hurricane. Your thighs clench, trapping Dean’s hand between your legs, and he groans, rubbing his fingers harsher and harsher against your g-spot. You’re shaking and rolling beneath him, and he has to grab the back of your neck and pin it down to keep you still.

Dean works you through your orgasm, whispering low praise in your ear as you float back down to earth. Your pussy feels empty, when his fingers finally pull away. Your eyes are slightly crossed, and your smile is dazed and a little stupid.

You don’t even squeak, when Dean grabs your thigh and flips you over. You keen, back arching and body twitching, but you’re mostly just staring stupidly and happily up at him. Dean swallows, his chest rising and falling fast, and leans down to press a soft kiss to your lips. You hum, eyes fluttering shut, and cup the back of his neck to hold him against you.

He drags his fingers lazily through the mess between your thighs, sending pleasurable little shivers up your spine. He drags your panties fully off your body, holding them up to his nose and taking a deep, long whiff before tossing them off to the side. He gathers your arousal on his fingers and slowly pulls away, rising over you with parted lips and gleaming, almost wholly black eyes.

Dean sucks your juices off his fingers, lapping them up with his tongue and a lazy, knowing smirk. Your breath catches. You almost push up to try and grab him, but you’re still foggy and boneless from the orgasm, and he shoves you back down with a broad hand splayed over your tummy.

“Dean-“

You cut yourself off under his stern gaze, swallowing nervously.

“Please?” You try again, and he chuckles.

“You’re cute.”

“I- I am not-“

“Yeah, you are. Cute when you cum for me,” he dips his fingers back into you, smirking lazily. “Cute when I touch you. Cute when you beg.”

“Deeeean-“

“Deeean,” he mocks, squeezing your upper thigh. “Listen to you. Fuckin’ adorable.”

You flush, a new wave of arousal hitting you like a rising tide, and you don’t even understand how you could possibly be ready that fast. Dean watches you pussy tremble and flutter, letting out a slow, rough breath.

“Son of a bitch,” he shakes his head, his hand moving to rub against his cock. “You got no idea what you do to me, baby, no fuckin’ idea.”

You swallow, watching him move against himself, almost enchanted. He really is prettier than is fair, in every possible way. His cock is thick and long, flushed at the head and leaking pre-cum against his thumb. Your tongue flicks over your lips, as you try to mentally measure the girth and length of him. You’ve taken toys before, when you got really curious. He’s bigger.

“You wanna touch, sweetheart?” He prompts, and you nod, your tongue flicking over your lips.

Dean pushes his hips forward, slowly taking your hand and guiding it against his shaft. He’s warm. Warm and hard. You dance your fingers down the length of him and he grunts, a vein ticking in his neck.

“Easy…” He rasps, and you nod nervously.

You find his balls, give them a light squeeze, and Dean catches your wrist.

“That’s enough.” He mutters, twining your fingers together. “Jesus, woman, gonna blow it before I even get inside of you.”

Your eyes widen. You’d almost forgotten about that part.

“That’s not going to fit inside of me.”

Dean chuckles. “Yeah, it will.”

“No, I mean like- It can’t-“

“It can.”

“Dean, I’m serious-“

He shuts you up with a quick rough kiss, and you go embarrassingly limp. His cock rubs between the folds of your pussy, bumping and pressing against your clit, and your breath hitches. Oh, God.

“Just do what I tell ya,” he mutters. “We’re gonna make it fit.”

You do. It is very easy to do what Dean tells you, when he follows through on all his promises. When he gives you such low and certain orders, and you find yourself molding perfectly around his cock.

Because it does fit. Somehow, Dean spreads your legs and kisses your pussy once—as if he can’t help himself—before crawling over you and slowly pushing the head of his cock inside of you. It’s tight at first. He grunts, pressing his brow to you shoulder, and rubs tight circle around your clit with his thumb.

“Open up for me, baby,” he rasps. “C’mon.”

You go limp with every inch he feeds you. The stretch is glorious, pulling you apart with every drag over your fluttering walls, every low grunt of your name from Dean’s lips. His determination to tease you seems to dissolve, by the time he’s fully seated inside of you, his balls pressed against your ass. He pants in your ear, hot and heavy, and cradles your body in his arms like it’s fragile.

“Slow,” he mutters, and it sounds like he’s talking to himself more than you. “Gonna go slow.”

You keen, at the first, lazy thrust of his hips. A lewd, wet sound fills the air, and the head of Dean’s cock pushes right up against that already abused spot inside of you, making stars dance behind your eyes. Every roll of Dean’s hips makes your whole body spark. He kisses all over your face, his own voice thick and wrecked as you clench around him.  

“Takin’ me so well, baby,” he rasps. “Feels good, doesn’t it. Feels so fuckin’ good, bein’ filled up with cock like you deserve-“

His words fall into a moan, his hips snapping forward, and the air gets knocked from your lungs. A sound you’ve never heard escapes you, and Dean chuckles, kissing your open mouth as he repeats the motion.

“Yeah, you like that.” He pulls almost fully out, then slams back forward. “Say it, baby girl, say you like it-“

“I like it,” you gasp out, sounding drunk to your own ears. “Love it, Dean- Fuck- Fuuuck-“

Dean captures your mouth in another kiss, and sets a brutal, drilling pace. You’re split open with every thrust, your every nerve on fire as he fucks you like a machine. He never gets too fast, just hard. Over and over and over again, until you’re gasping for air and clawing at his shoulders. That pressure turns molten and demanding, threatening to burst. Dean’s fingers dig into your hips. He moans in your ear, his own words staring to slur.

“Tight,” he moans. “So fuckin’ tight- I- I can’t- Shit-“

Dean’s hands fumble, dragging over your thighs and as he gropes for your pussy. Two fumbling fingers find it, rubbing tight circles, and you cry out, clenching down on his cock.

“Let go, sweetheart, need you to let for ‘f me- Fuck-“

Your orgasm hits you even harder than before, and your vision goes white. Your pussy flutters and clenches, something hot gushing out as your body trembles with overwhelming pleasure. It’s a strange sensation, but not bad. Not even close. You think you scream with pleasure, but Dean slams his mouth over yours and muffles the sound.

His hips stutter and jerk. You whine his name and he grunts, slamming forward and burying himself at the hilt as his cum spurts deep inside you, mixing with your own release.

You’re almost gone to the world. Dean lies over you, kissing you as you float back down, murmuring praise you can barely hear.

“Gonna clean you up,” he grunts, and you whine when his weight disappears.

“Deeean.” You grab at the air and catch his bicep. “Stay.”

You pout at him, eyes watery and hopeful. He just chuckles, kissing your knuckles before drawing back up, and promising to return.

He better. You really don’t want to let go of him now.

Dean brings a wet, warm towel, and cleans between your thighs. You didn’t realize how sore you were until he touches you with such light hands, but it’s a good kind of sore. When you moan, it’s not even really in pain.

He brings you water. A snack and a fresh shirt, that he bundles you in like a penguin. You somehow end up curled against his chest, half asleep and smiling against his bare, warm chest.

“I like you,” Dean says suddenly, and you beam. You don’t think you’ve ever felt so bubbly in your life.

“I like you too-“

“No,” his jaw works, the words low and tight. “I like like you- Like- Fuck-“

He runs a hand over his face, shaking his head. It’s almost adorable.

“You- You’re just- That really wasn’t nothin’ for me, sweetheart, not even close-“

You take his trick. You push up on his chest, press your lips together, and kiss him until he shuts the fuck up. He kisses you back immediately, cupping your face between shaking hands. You smile against his lips, pulling back just enough to whisper, “I like you too.”

Dean’s eyes snap open, his voice hoarse. “Really?”

“Yeah,” you flush. “A- A lot.”

Dean grins. He smiles wider than you knew he could, and slams a shorter rougher kiss against your lips before pulling back again. Like he can’t stand not to look at you for too long.

“Can I take you out?” He says, and you nod.

“Can we have more sex,” you whisper, and he laughs, pressing another kiss against your lips.

“Any time you want, baby.” He says. “You’re mine now.”

✦End note: drooling for him ✦

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Y’all had wrapped up the case hours ago. The ghost was gone, bones were burned, the town was safe– which meant Dean had declared y’all were celebrating with greasy burgers and cheap beer at the nearest dive bar. Sam should've known better than to leave you alone in a place like this– not because you couldn’t handle yourself, God knew you could… But because you could handle yourself far too well for men’s fragile egos. He'd barely walked over to the bathroom, hoping to talk to Dean before he ordered too many beers for y’all to handle when:

"Mind if I sit?"

You didn't even bother looking up from your phone, this man’s voice wasn’t either Winchester’s therefore you couldn’t care less. "I’d mind it very much"

The chair scraped against the sticky floors anyway, the man dropping down onto it unceremoniously. "So that's a yes, huh?"

"No" You corrected flatly. "That was a complete sentence that said literally the opposite"

Across the room, your boyfriend glanced over his shoulder while waiting at the bar. "...Someone's bothering her" He muttered, his asshole-spidey-sense tingling. The bartender slid three beers across the counter towards him but Dean didn't move. Not yet. Because he knew you, if you wanted help, you'd ask. Besides, he’d seen this exact same scene play out countless times before– his girl could hold her ground just fine without him playing knight in shining (flannel) armor.

"You don't smile much, do you?" The stranger continued.

"Must be that" You hum dismissively, eyes still locked down on your phone. 

"Bet I could change that, huh dollface?"

You visibly cringed at that, a disgusted sneer pulling at your lips while automatically clapping back with a: "Bet you couldn't even change a tire" You’d learnt that attacking their fragile masculinities usually was enough to get them to back off.

The guy laughed, that dismissive chuckle men always used to act nonchalant and unaffected despite being desperate tryhards. Dean snorted into his beer, enjoying the show of you shutting this random dude (that clearly wasn’t getting a not-so-subtle hint) down. "Come on, princess" He doubles down, leaning close enough for you to smell the reek of his sweat.

You finally looked him dead in the eyes. "I need you to understand something" His grin widened, hoping to get something out of you other than an eyeroll. "I have absolutely no interest in talking to you"

The man scoffs, still leaning far too close for your liking. “Playing hard to get is really not your look" He pauses, shamelessly eyeing you up and down. "You got a boyfriend?" Ah yes, the ‘you’re not fawning over me therefore you must be taken’ routine, how original. Truly, bravo random guy, bravo. Instead of wasting your time trying to educate him, you simply pointed toward the bar where Dean was sipping his beer. The hunter raised an eyebrow, smirking over the rim of his glass in silent acknowledgement. "The guy in the busted up leather jacket?"

"Mhm" You nod dismissively. 

"What he doesn't know won’t hurt him, huh?" The balls on this man, Jesus fucking Christ.

Dean was already walking over. Not fast or angry like other men might’ve been when someone tries to blatantly seduce their girlfriend, nah. He was just confident, calm. You noticed him from the corner of your eye but didn't greet him, didn't really need to yet. "Everything alright?" He asked casually, setting a fresh beer in front of you.

The guy looked between the two of y’all, barely glancing at the blonde, instead fully focused on your deeply unimpressed side profile. "We're just talking"

"We're not" You corrected with a sharp scoff, taking a sip of your newly acquired beer.

Your boyfriend hummed, pointing at you as you spoke. "See, now that's usually a clue that she doesn’t want you buddy"

The guy scoffed, side eyeing him. "Wasn't talking to you, tough guy"

Dean smiled, that easy, boyish grin of his. "I know" Silence. "But…" He continued pleasantly. "My girl's said no about four different ways now–" The smile never left his face. " –so m’starting to think you're having trouble understanding English" Something about Dean's tone made the man rethink every decision he'd made that evening, he mumbled something under his breath before disappearing toward the pool tables. What was it about these types of guys that made them only listen to men instead of the women actively telling them to fuck off? Anyways, he was gone and that was enough.

The hunter watched him leave, an amused huff escaping his lips before turning his attention back over towards you. "You good, sweetheart?"

You nodded once, pocketing your phone now that you had actual company. "M’fine" He searched your face for a second, looking for any sign that might indicate the contrary. Once satisfied, he slid your beer closer and settled beside you like nothing had happened.

Sam came back from the bathroom just in time to catch the stranger shooting your table one last dirty look. "What'd I miss?" He asks, confusedly glancing between y’all and the sulking man.

Dean shrugged. "Romeo got lost" While you replied a simple: "Told him I'd rather lick the bathroom floor than talk to him" The younger Winchester just blinked before nodding, for some reason accepting that as a logical response.

An hour later, another hunter wandered over– apparently one of the guys’ hunting buddies from a while back, Max something was it? You don’t know, don’t really care– he’s nice enough to tolerate and the brothers like him so that’s that. "So..." He starts speaking, looking at you but nodding towards Dean. "Thought you didn't like men"

Dean looked up from his pie at the mention of him, cherry filling still smothered around his lips from his overly-ambitious bites. Meanwhile, you looked genuinely confused by the question. "I don't…?"

The hunter gestured openly at the blonde sitting across from them. "Then how come there’s him?"

You frowned, the answer being strikingly obvious to you. "Well that's Dean"

"Yeah" There’s a pause until the hunter realizes you were gonna leave your explanation like that, instead he prompts you by repeating his previous question: "So how come there’s him?" You just look at him, simple and confused. "I just– I mean" He laughed awkwardly. "He's a man too"

You stared at him for a long second before shrugging. "I know"

"Then what's the difference?"

Your boyfriend stayed very quiet– he never answered questions like that for you. If someone asked why you tolerated his presence, he didn’t need to prove a point, he’d just let you reply yourself. You’re a big girl, you could handle it just fine. "The difference–" You said simply. " –is that Dean has never made me regret trusting him"

After that, silence settled over the table– not necessarily uncomfortable, but different now that’d you just calmly set out your reasoning like that. It didn’t take long for the hunter to leave after that, something about his twin sister being outside. Not that you’d been paying much attention, you were too busy eating the fries off Sammy’s plate, didn't think much of it. Dean was definitely thinking about it though– his usual grin was gone. Not out of embarrassment or anything like that, it had melted away into something softer. Because no one had ever put it into words like that, definitely not him with his gruff words and no chich-flick moments mentality. You noticed him staring. "What?"

"...Nothin' " He huffs, defensive and fond all at once.

"You've got the weird face"

"Gee thanks, sweetheart"

You roll your eyes at his deflection, a reluctant hint of a smile tugging at your mouth. "Y’know what I meant– You have a feelings face"

Sam choked on his drink, clearly enjoying seeing his brother be the one being teased for once. Dean shot him an unamused look. "Eat your damn fries"

Later, the three of you stepped out into the cool night air. Sam offered to drive ‘his’ (he’d hijacked it two towns back) car back to the motel, wanting to stop by the sheriff's station one last time. The eldest Winchester unlocked Baby, while you climbed into the passenger seat automatically, claiming your usual spot. A few minutes into the car ride, your hand wandered across the bench, instinctively reaching out for him. Dean automatically intertwined your fingers with his without even having to take his eyes off the road, thumb rubbing slow circles over your knuckles. "Y’know" He said quietly.

"Hm?"

"...Thanks"

You frowned, looking over at him, streetlights catching his unfairly pretty profile. "For what?"

He shrugged, trying to brush it off despite how much it’d clearly mattered to him. "What you said back there"

"Oh" You looked out the window once more, a fond smile tugging at your lips. Despite all the disgusting men out there, constantly trying their luck with you– there would always be a Dean here next to you. With his stupid swagger, dumb jokes and his ridiculously big heart. "Was just answering his question"

"Yeah" He replies, a soft breath escaping him as he glances over at you with a warm smile before looking back at the road ahead.

Another silence, then: "M’proud of that"

Dean glanced over. "Hm?"

"Trusting you" You said it so matter-of-factly that it made his chest swell with pride and love all at once, his jaw worked for a second before ducking his head with a quiet huff. It wasn’t some grand over the top declaration or dramatic confession, just a fact. "I don't hand that out easily, y’know" You chuckle softly, still holding onto his hand.

His hand was on your cheek and the other was pressed on the hood of his car. He had you sitting on top of it. He prioritized your comfort over anything, making silly jokes about how he’d rather have you relaxed while kissing you. And God, you were starting to think those weren’t jokes because you felt like your legs would give up if you were standing.

When Dean palmed your hair and faintly pulled your head to himself, you gasped into his mouth. He kept licking your lips, pressing open mouthed kisses all over you.

His lips were not soft, but they felt like cotton candy over yours. You felt his hand on the hood slowly slide down and snake over your leg. Everything was so dreamy that you were scared to wake up. But yet, everything was so real. His touch, his lips, him…

“Dean,” you murmured against his lips and he mumbled something incoherent. You tried to push him away to speak again, but he didn’t move an inch. “Dean…”

“Yeah?” He pressed his lips against yours, sealing them in a gentle way that it felt like you were bound to stay like that forever.

That would be amazing.

You closed your eyes, deepening the kiss even further. He sighed against you. This time when you pushed him away, he pulled himself back. But he playfully captured your lower lip in his teeth and slightly bit there.

“What’s wrong?” He gently patted the side of your leg, encouraging you to speak up.

“I’m cold,” You said, biting your lower lip right where he did.

“Oh?” His smile got bigger and bigger…

“Yes.”

“We can get inside the car.” He suggested the thing you wanted him to.

“Such a smart boy.” was all you said as you wrapped your legs around his waist, waiting for him to carry you.