Winchesterfields Reads

Cruel World: Chapter Twenty

Everything was perfect—you were about to welcome a baby girl into the world and finally leave the life of hunting behind. Sam was supposed to have it all: the house, the family, maybe even a dog in the backyard. But before the three of you could begin your new life in an old craftsman home on the prairie, the apocalypse arrived.

All Sam had to do was lock Lucifer in the cage…

Pairing: Sam Winchester x fem!reader, Dean Winchester x OFC

WC: 5.9K

CW: 18+ MDNI, canon-type violence/injury, blood, wound care, mild angst/emotional tension, language, implied smut, mentioned character death, some sweet, tooth rotting fluff these idiots deserve <3

A/n: this one's a little longer as I'm finally wrapping up my first multi-part fic! I separated this chapter into two parts to bring two storylines together.

Thank you to everyone who's come along for the ride, and I hope you enjoy!

Cruel World masterlist

“Share my body and my mind with you, that’s all over now. Did what I had to do, I found another anyhow.” - Cruel World, Lana Del Rey

𝙥𝙖𝙧𝙩 𝙤𝙣𝙚

Dean had never been on that side of the line.

Waiting and wondering.

Pacing in front of the same row of motel rooms where she’d left him. Holding the empty coffee cup—her number scribbled across the cardboard sleeve in fading blue ink—in one hand and his phone in the other. He stared at the numbers like there was a punchline hidden somewhere among them.

He’d never been the one wondering how soon was too soon to call.

It had been two weeks since Rhi had pulled out of the parking lot in her old Bronco, glancing over her shoulder at him one last time.

He’d tried like hell to forget her.

It was pointless.

It wasn’t just that she was pretty, though that certainly wasn’t helping. She wasn’t the kind of woman Dean usually noticed first in a crowded bar. No impossible curves. No bright lipstick. No easy invitation.

Rhi made people earn her attention. And for some reason, he wanted it. She didn’t buy his “cowboy Casanova” act—as you’d once called it—which meant he didn’t feel the need to perform around her.

Without the act, he was just Dean. A guy who’d only ever been himself around a handful of people.

Leads about the wolves had dried up and Crowley was getting impatient. Maybe he could call her under the guise of chasing down leads. 

That might give her the impression that he’s using her. The thought made him shudder. 

Finally, he dialed her number with a shaky hand and continued to pace while he waited for her to deny his call. 

After three rings, he was ready to hang up. Instead, he stopped dead in his tracks at the sound of the voice he’d been unable to forget.

“Hello?”

Silence. His mind went blank. He’d even forgotten her name. 

“Hey…Rhi.”

Nope. He’d forgotten his name. 

“Uh. It’s Dean—“

Nailed it, he thought. 

“Dean…”

His heart sank at the sound of her struggling to remember him. 

“Winchester.”

“Doesn’t ring a bell.”

If he had died, he had just discovered a new circle of hell. One that Lucifer wouldn’t even visit. 

“Oh…I’m sorry—“

“Kidding! I was wondering if you’d ever call.”

He caught a glimpse of his reflection in the window outside of his motel room. He looked as flustered as Sam did when Dean brought him to a strip club for his eighteenth birthday. Ears tipped pink with an involuntary, nervous smile tugging at his cheeks. 

Rhi agreed to “assist” Dean on the case to track down the werewolves. Research only, he had insisted, to which she rolled her eyes. Her defiance frustrated the hell out of him. It prevented him from fulfilling his purpose in life—keeping people he cared about safe. 

“Haven’t you died a time or two, Dean? Why are you so worried about something happening to me?”

He couldn’t answer that. Not without spilling his guts, because he knew Rhi could see through his bullshit. He’d risk telling her that, even though he barely knew her, he didn’t want to lose her. 

“Shit shit shit shit—“

“Language, asshole.” Rhi laughed carefully before wincing. 

While the group was attempting to restrain the werewolves and bring them to Crowley, Rhi had let her guard down within striking distance. Of course, Dean was the only one remotely interested in her injury. He quickly guided her to the Impala. Shrugging off his flannel, he balled it up and pressed it hard against the bleeding wound near her hip.

Dean glared at her in the passenger seat, completely ignoring the blood that was staining the door and leather seat. He reached over her and pulled the fabric back enough to see if she was still bleeding, which resulted in fresh blood rising to the surface. 

“Son of a bitch—I’m takin’ you to the hospital.” 

“You’re not taking me to the hospital.” She winced through gritted teeth. “Just take me back to the motel.” 

His jaw ticked and his knuckles were pale from gripping the steering wheel. 

She was smart enough to know this wasn’t a wound she could stitch in a bathroom. She didn’t want to admit that she was terrified of hospitals. After the death of her parents, she associated the smell of antiseptic in a sterile environment with death. 

He could see the tiny dimples forming when her chin quivered. She pressed the shirt tighter against her hip and tried to cloak her fear with pain. 

Her face softened when she felt Dean grab her hand that was gripping the seat and tracing his thumb across her knuckles.

She was trying like hell to dislike the man. Trying to lessen the sting when he inevitably disappointed her. But doing things like that was making it difficult. He didn’t ask if she was scared. Didn’t patronize or crowd her. Just acknowledging that he saw her and didn’t think any less of her. 

Rhi was going to be down for at least a few weeks while she healed from the deep claw mark to her side. 

Dean stayed in the waiting room, dodging calls from the Campbells and Crowley. Eventually he was able to visit Rhi in her recovery room. 

“Just take me back to the motel and I’ll take it easy for a few days.”

Dean shook his head. 

“No. You don’t need to be staying in some shitty room trying to take care of yourself. Doc said you lost a lot of blood. You need to rest. And you need help keeping the wound clean.”

She folded her arms in front of her chest. 

“Why do you care, Dean?” Her voice was soft as she tried keeping it steady. “I’m basically a stranger to you.”

There was softness beneath the harshness in her expression.

“And what? Do you have some big fancy house with a white picket fence where I can put my feet up for a few weeks?”

“I mean… it doesn’t have a fence.”

The words were out before he could think them through. His stomach fluttered at the idea. He’d need to clear it with Sam and you first. But like you’d reminded him more than once, it was his home too.

Her eyes widened when she realized he wasn’t joking.

For some reason, that reaction stung more than he expected. He wasn’t offering because he felt obligated. He was offering because the thought of dropping her back into a smoke-stained motel room and driving away made his chest feel tight.

“Rhiannon, please—”

“This wasn’t your fault, Dean. You don’t owe me anything.”

She didn’t want him collecting guilt like spare change. Didn’t want to become another person he felt responsible for saving.

“You wouldn’t be in this mess if it wasn’t for me. I never shoulda called you.”

He pushed himself out of the chair and paced a few steps away before she could see how much he meant it.

“If we’re being honest…” she said quietly. “I’m glad you called.”

Dean stopped and she felt nervous under his gaze.

“I dunno. You’ve kinda grown on me.”

His shoulders relaxed.

“In a fungus-y sort of way.”

There she is, he thought. He breathed a sharp laugh and his gaze dropped to his feet to hide the blush creeping up his neck.

“So you’ll stay with me? No strings attached. Just a free bed and home cooked meals—“

“—please stop talking.” The entire ordeal, coupled with the blood loss she sustained, was brewing a massive headache. She was also trying to fight the  warmth blooming in her chest and spreading to her cheeks. 

Rhi agreed to accept his hospitality for a couple of days only. She made it clear that even though she could barely walk, she could still kick his ass. Or at least shave a few more years off of his life. 

𝙥𝙖𝙧𝙩 𝙩𝙬𝙤

After checking to make sure Willa hadn’t woken up from Walker’s playful barking, you joined Sam downstairs with Castiel. You were incredibly frustrated by the timing of his arrival. All of your hormonal need had been converted directly into bitterness.

Settling onto the couch beside Sam, he rested a hand on your bare thigh and squeezed lightly, shooting you a quick smile meant only for you. You sighed and let your head fall against his shoulder while you collected yourself.

Walker plopped down at the angel’s feet, happily panting and looking up at him for more attention.

Sam’s eyes flicked between the dog and Castiel.

“Oh. Some animals are drawn to celestial beings like myself. Your dog appears to be one of them.”

Sam raised his eyebrows, fascinated by Walker’s immediate attachment to him.

“Anyway…” Sam sighed and began wringing his hands together nervously. He leaned forward, resting his elbows on his knees. Glancing over his shoulder, he found you already looking at him. You were clearly exhausted and frustrated. But you were still there—at his side like always.

He wanted to minimize the situation. Make it sound smaller than it was. The reality was that his nightmares about Hell, the Cage, and his time without a soul were threatening the fragile peace the two of you had finally found. They were warning signs that the barrier Death had constructed around his memories was failing.

“We’re retired, Sam.”

Your quiet voice reminded him of the conversation you’d had in the car. That the two of you didn’t do solo missions anymore. Not now. Not when you had everything to lose.

Sam explained everything. From the first memories that had started bleeding through. The dreams that no longer felt like dreams. The nightmares of his soul trapped in the Cage with Lucifer and Michael.

The things he’d witnessed through the eyes of a stranger.

The things he’d done to you.

Castiel listened silently, his expression unreadable.

“I don’t know what to do, Cas.” Sam rubbed a hand across his face. “I can’t afford to lose it completely. We can’t keep living like this.”

He looked at you again for reassurance. Your tired eyes were glossy as you listened to him recount the twisted reality of the last six months.

Sam’s return from Hell had really only marked the beginning of yours.

Even though you’d found peace, it had come at a cost.

“I can’t help but feel responsible,” Castiel admitted quietly.

You bit your tongue. Selfishly, irrationally, part of you still resented him. Sam had made his choice to stop the Apocalypse, but that didn’t mean you had forgiven everyone involved. You likely never would. 

Not when you hadn’t even fully forgiven Sam.

“Let me see what I can do.”

Castiel stood and stepped toward Sam. Before you realized what you were doing, you were already on your feet. Your arm moved protectively in front of Sam’s chest.

“What the fuck does that mean?”

Your mistrust of him made you question every move he made.

“Y/N, it’s okay.” Sam reached for your hand.

“I need to examine whatever remains of the barrier Death created around his soul,” Castiel explained. “I need to know whether it can be repaired.”

A tense silence settled between you.

“And how exactly are you supposed to do that?” you asked.

“It’s difficult to explain.” Castiel tilted his head slightly. “But it won’t be pleasant.”

Unbeknownst to either of you, Sam remembered exactly what that meant. He remembered Castiel discovering his missing soul, and Death forcing it back into place. He knew it was agonizing. But the cost of losing everything was worse.

“Let’s just get it over with.”

Sam’s resigned sigh earned matching looks from both of you.

The three of you moved to the basement—technically the root cellar of the old house—so as not to risk waking Willa.

“Whatever happens,” Sam said firmly, “do not stop him.”

Your face fell as you wrapped your arms tightly around yourself. Partially to fight the icy chill pressing in from the cellar, and partially because of the edge in his voice.

It was every bit as terrible to witness as you’d expected. Every instinct in you screamed to eliminate the threat. Instead, you paced nervously, staying close enough to intervene if you needed to.

Even with his belt clenched between his teeth, Sam’s body was screaming for relief. His skin flushed red, every vein standing out beneath the surface. His brows were drawn tightly together.

Eventually, his body relaxed against the chair as he inhaled deeply, not realizing how desperately his lungs had been starved for air.

“Just as I suspected,” Castiel said, almost to himself, as he stepped away from Sam.

Sam was still catching his breath.

“The problem isn’t the wall. The problem is you, Sam.”

Sam’s eyes narrowed on him, confusion written plainly across his face.

“There are cracks, so to speak. But they aren’t from age or poor construction.” Castiel tilted his head slightly. “They’re from your inability to let things go.”

The weight of the truth settled over Sam in the form of guilt.

“Using some of my grace, I can seal off the remaining memories. But you have to let them go, Sam.”

You immediately turned toward him, hopeful he was receiving the offer the way you had—as a gift. As a key to finally moving forward.

Instead, he still looked cautious and unconvinced.

Castiel sighed. As an angel, he possessed strong moral convictions—arguably stronger than Sam’s. But he wasn’t burdened by human emotion the way people were.

“Humans do not heal by knowing everything. That is not how you were designed.” Castiel watched as the words settled over him. “They heal by deciding what they can survive without knowing.”

He paused.

“You were given free will, Sam. Use it. I can give you the opportunity to move forward.” His voice finally softened. “Please take it.”

He seemed almost as determined to help Sam as you were. There was desperation in his words and something uniquely human—hope.

“Sam.” Your hand settled on his shoulder, grounding him. “Please.”

He nodded and swallowed around the knot in his throat. There may not have been anything he could have done to make it home to you the night he was locked in the Cage. But now, there was nothing he wouldn’t do to keep his family together.

It was nearly dawn by the time you both made it upstairs. You were exhausted, but neither of you closed your eyes when you crawled into bed together.

Maybe it was the relief of the whole ordeal finally being over.

Maybe it was a side effect of Castiel’s grace.

Whatever it was, you both felt ten years younger. A hundred pounds lighter.

Curled against his side with your legs tangled together, your cheek squished against his chest and his fingers loosely threaded through your hair, you felt like twenty-somethings again.

He still got butterflies when you glanced up at him through your lashes, squinting playfully and asking what he was staring at.

Without warning, he rolled you onto your back and settled between your legs, caging you beneath his broad frame.

Your fingertips traced the hard lines of muscle in his arms before slipping into his hair.

“You should rest, Sammy.”

Your voice and your body were giving him very different messages.

“I know. And I will.”

He punctuated each statement with a kiss trailing along your throat.

“After I take care of you.”

You pinched the bridge of your nose and let your eyes flutter shut as Sam turned onto the gravel driveway, trying to stave off the next wave of pain throbbing behind your eyes.

It had been three weeks since Castiel had shown up in the middle of the night and given you your life back.

Three weeks since Sam had finally chosen to let go of the past in exchange for the possibility of a future. A future that apparently included themed birthday parties for toddlers.

“Fucking Valerie,” you muttered under your breath. “Fucking face paint. Fucking glitter. What the fuck.”

“Jesus, sweetheart.” Sam huffed a laugh as he checked the rearview mirror to make sure Willa was still asleep. “The mouth on you.”

“Sorry,” you groaned, eyes still squeezed shut. “My head is killing me and that… toddler mosh pit… didn’t help.”

He fought back a smile. The party—if you could even call it that—had been an hour of pure chaos.

Willa had consumed roughly a month’s worth of artificial sugar and crashed the second she’d been buckled into her car seat. The emotional fallout would arrive before bedtime. He’d stake money on it.

“Well, I’ll take care of getting her inside—”

He trailed off.

You opened your eyes and noticed the Impala sat in its usual spot. Next to it sat an old Ford Bronco that you didn’t recognize.

Your brows furrowed.

“Just wait here.”

Sam’s voice was low, but lacked any real concern. Dean would never bring anyone dangerous around you or Willa. Still, he didn’t take chances anymore.

The smell of bacon grease and the sound of quiet conversation drew him toward the kitchen.

“Dean?”

Rhi stood so quickly her chair nearly tipped backward. One hand moved to grip her side while the other braced against the table. Her eyes never left Sam.

“Hey—relax. Sit down.”

Sam stopped short, immediately noticing her reaction.

“Hey, Sammy.” Dean rubbed the back of his neck awkwardly. “I, uh, tried calling you.”

After a few rushed introductions, the tension eased slightly—slightly being the operative word.

Curiosity pulled you inside. After letting the door click shut behind you, you were immediately greeted by the familiar sight of Dean in the kitchen, leaning against the counter with his arms loosely crossed over his chest, framed perfectly in the doorway.

He didn’t notice you, though. His attention was fixed on someone else. Someone who made his features soften and those subtle crow’s-feet appear when he smiled.

Willa was asleep on your hip, her head resting on your shoulder. Your view was suddenly obstructed by Sam, who noticed you standing in the entryway. He gently gathered Willa into his arms without waking her.

“Who is that?”

“A friend of Dean’s. I think she’s staying with us for a few days.” He kept his voice low, but Willa stirred anyway. He shot you an apologetic look before carrying her upstairs.

You continued to observe a version of Dean you hadn’t seen in a long time. One of genuine happiness and comfort.

His earthy green eyes had a spark in them again, and there was a healthy glow about him you hadn’t realized had been missing.

Walker wandered into view and sat at Dean’s feet, clearly interested in whatever was on his plate. When Dean glanced around to see if he could get away with sneaking him a scrap of food, his eyes finally landed on you.

Heat rushed to your cheeks and you quickly pulled yourself together. He hadn’t seen you since you’d completely fallen apart in front of him. It had only been about a month, but it felt like a lifetime ago.

Even though you felt like a train wreck standing there, he seemed to immediately recognize the dramatic improvement in your condition.

You finally willed yourself forward into the kitchen and were overwhelmed by the mixture of scents, making your nose wrinkle. Strong coffee, breakfast food, and the hunter special—gun oil and motel soap. All familiar, but overpowering with the migraine you’d been fighting all day.

“You okay?”

Dean’s familiar, steady voice centered you.

You hummed and nodded, offering a quick smile to compensate for what your body language was probably saying.

Dean introduced you to Rhi, who waved politely mid-chew. She certainly looked the part of a young hunter. Edgy, alert, and hyperaware of her surroundings.

But there was more to it than that. She was pretty in an effortless way. The kind that looked good in harsh motel lighting and after sleeping in her truck. The kind that didn’t seem to require any effort at all.

You glanced down at yourself. There was still glitter on your sleeve. Probably in your hair, too.

“Rhi, this is Y/N.”

You smiled politely while tugging your sweater over your hand and attempting to rub at the glitter stain. It only spread the irritating substance.

Dean briefly explained the situation while watching your expression for any sign of apprehension.

“Well, we’ve all been there.” You gestured toward the bandage peeking out beneath the hem of her shirt. “Everyone in this house has, anyway.”

She tilted her head curiously.

“You’re a hunter too?”

You let out a weak laugh.

“Once upon a time, yeah. We had the opportunity to retire and took it.”

Almost on cue, a tired cry echoed from upstairs, followed by a frustrated sigh and the familiar creak of old floorboards beneath Sam’s feet.

You used it as an excuse to end the increasingly uncomfortable interaction.

“I’ll set some towels and blankets upstairs for you. Stay as long as you need to.”

Dean was visibly relieved by your warm reception, but he still watched you walk away, searching your expression for signs that you were saying one thing and feeling another.

Rhi noticed the way his gaze lingered. The way he seemed to be looking for something beneath the words. There was no resentment in the observation. She simply filed it away the way hunters do.

After Sam got Willa settled again, he found you decompressing in bed. Hovering somewhere between sleep and relaxation. After grabbing you a glass of water and a couple migraine tablets, he sat beside you on the edge of the mattress.

“You sure you’re okay?”

“It’s just a migraine, Sam. I’ll live.”

He rested a hand on your leg and gave it an affectionate squeeze.

“That’s not what I’m talking about.”

You finally cracked an eye open.

“What? Dean’s friend?”

He chuckled at your dismissive tone.

“You’re fine with her staying here?”

Frustrated, you pushed yourself upright and immediately winced when the pressure behind your eyes intensified.

“Why wouldn’t I be?”

“Just checkin’.” Sam shrugged awkwardly.

He pressed a kiss to your forehead before heading back downstairs to join his brother. Eager to hear about life on the road. Now more determined than ever to find Dean a way out of Crowley’s debt.

Sam couldn’t help but notice the chemistry between Dean and Rhi. And the way they both tried to ignore it. How they stared at each other when they talked before quickly looking away whenever the other noticed. 

She really was a female version of Dean. Less false bravado than him, but she still fought to maintain a hardened image of herself, even when cracks appeared and revealed her soft underbelly.

Guilt twisted in his gut when they described Rhi’s injury. The same way it did for Dean. Hunting was dangerous enough without the added risk of bringing live monsters back to Crowley.

“This has gotta stop, Dean. I never should have let you take this debt.”

He expected the usual cocky, dismissive retort.

“I’ve been doing some research.”

Sam leaned back in his chair and crossed his arms in disbelief.

“Now who’s the nerd?” he huffed under his breath.

Rhi looked equally surprised, seeing as Dean had attempted to assign her to research duty.

“Alright, alright.” Dean gestured dismissively. “It’s hard to find something to hold over the King of Hell. But—”

Dean paused and pulled out a weathered lore book that Sam recognized immediately. He tried not to let himself fantasize about long nights poring over ancient texts and a glowing computer screen.

“—if we could find the bones of his vessel?”

Sam’s interest was piqued when he realized where Dean was heading. He was thoroughly impressed. Burning the bones of a demon’s vessel killed the demon within.

“Isn’t he, like, four hundred years old though? And Scottish? How the hell are we gonna find his bones?”

“Without going to Scotland?” Rhi asked, pressing her knee against the edge of the table. “I have no idea.”

Her eyes flicked between the brothers as they arrived at the same conclusion through a silent exchange.

“Maybe Cas?”

“Worth a shot.”

Dean shrugged and agreed to try summoning the angel who had been particularly difficult to reach lately. As usual, it would be a waiting game.

After a tense standoff, Dean convinced Rhi to take his bed while he slept on the couch. It had been years since she’d slept on anything better than a stiff motel mattress or a pull-out couch. Most nights she slept in the back of the Bronco at a state park or national forest. To her, it was more comfortable than a stuffy motel room and reminded her of camping with her parents when she was a kid.

The soft mattress and fresh-smelling comforter were a welcome change.

The first day was unnaturally quiet despite the addition of two more people to the house. Willa was cautious of the stranger at first, but she was also the first to break the ice. Once she let her guard down enough to smile and laugh around Rhi, life resumed as normal.

Rhi was impressed by how a gun-wielding, battle-worn man like Dean could soften enough to carry a toddler without breaking her. The same booming voice that could break up a bar fight could read the same board book twenty times in a row without complaint.

She did her best to stay out of the way and quietly observe the household dynamic.

You and Sam were clearly in love and shared parenting responsibilities equally. There was never any question about Willa’s parentage—she was a spitting image of her father with her hazel eyes and messy brown locks. But some of her mannerisms and expressions were a curious blend of yours and Dean’s.

Dean had given a vague explanation of the last two years. She knew Sam had essentially been dead for a year and then simply… come back. It would have been miraculous if he wasn’t a Winchester.

He never mentioned the way your relationship had changed after his loss, but it was obvious that it had.

It was obvious in the same way a smoking candle revealed that it had once burned brightly. Love had existed there once. It had burned hot and fierce. Now all that remained was a pleasant lingering scent—a reminder of a different time.

It showed in the way Dean dished up your plate at dinner while you got Willa settled. Or how he always brewed enough coffee so there would be a fresh cup waiting when you woke up.

His touch didn’t linger. Your breath didn’t hitch. But your lives were still uniquely intertwined. In the way only surviving tragedy together can be. 

A few days later, you offered to help Rhi change her bandage while Dean was running errands with Sam.

“It’s really no problem. I’ve patched those idiots up more times than I can count.”

You asked about her life. Trying not to be too invasive, even though she was standing shirtless in your bathroom save for a sports bra.

It had been so long since you’d talked to another woman that you found yourself opening up without even trying. For once, you didn't have to lie about how you met Sam. Or what you did after high school instead of going to college and chasing a dream job.

It was easy to see why Dean liked her so much, even if she was nothing like the women he usually went for. She was more than tolerable—you actually liked her. Even if you were slightly intimidated.

“I don’t think I’ve ever seen him this happy.”

The words left your lips before you could catch them. You silently kicked yourself, hoping you hadn’t accidentally ruined something good for him.

Sensing your anxiety, Rhi gently nudged your shoulder.

“Girl. Chill.”

You let out a nervous sigh.

“Just try not to hurt him too badly.” You quipped, though there was a thread of sincerity beneath it. “He’s more sensitive than he looks.”

She raised an eyebrow.

“The man cried watching a Disney movie. He should come with a handle with care sticker.”

“What movie?” Her voice was tight while she stifled a laugh.

You pressed your lips together, trying and failing to suppress your own laughter.

“The Brave Little Toaster.”

For a moment she just stared at you. Then both of you dissolved into uncontrollable laughter. 

At that moment, you weren’t a mom or a soon-to-be wife. You weren’t a former hunter. Or a survivor of tragedy. You were a woman laughing hysterically in a bathroom with another woman. Gossiping about a silly man. It was a tale as old as time.

You hadn’t heard the brothers when they came home. They just stood at the base of the stairs listening to the chorus of wheezing laughs. The thought passed between them silently that they hadn’t heard you laugh like that in years. 

“Guess I’m not as funny as I thought I was.” Sam shrugged at the idea. 

“Trust me, Sammy. Out of the two of us, I’m the funny one.” 

Eventually, Castiel did appear. Of course, it was at an inconvenient time and nearly gave everyone a heart attack. He agreed that the bones of Crowley’s vessel would make excellent leverage. If they could find them, Crowley would have little choice but to release Dean from any debt he believed Sam owed him.

Dean could finally move on and do whatever he wanted with his life. He didn’t want to leave hunting completely. It was too deeply ingrained in the fibers of his being. But he wanted the ability to choose it.

More than freedom, though, he wanted somewhere to belong. More importantly, he wanted someone to belong to. Whether or not that someone was Rhi, he wasn’t sure yet. But you had awakened something in him. A part of himself he’d buried beneath duty, guilt, and self-sacrifice.

You had shown him that he was worthy of belonging and being loved.

The rest happened surprisingly fast.

Once Castiel located the remains of Crowley’s vessel, you agreed to let Sam join his brother to handle the negotiations. The only condition was that Rhi went along to supervise.

Crowley complained loudly, threatened everyone equally, and eventually decided the arrangement was no longer worth the trouble.

Unlike that night more than a year and a half ago, Sam came home.

You both knew this would be the last time that you’d have to wonder. 

You were on him the second he set foot on the porch, nearly knocking him off his feet. Laughing, he caught you around the waist and helped you wrap your legs around him.

You buried your face in his shoulder while he held you effortlessly against his chest. Even after he set you down, you couldn’t bring yourself to let go.

“Why’re you crying?”

Sam tried pulling back when he felt your shoulders shaking.

“No.” You shook your head against him, laugh-sobbing into his shirt.

His hands rubbed slowly up and down your back.

“Baby… why?”

“I don’t know!” you cried through a nervous laugh. “I don’t know.”

Dean and Rhi were lost in their own world while they unloaded the Impala and casually debriefed in the driveway.

Neither of you noticed Castiel until he was standing a few feet away.

“Congratulations.”

Both of you jumped and you cursed under your breath. 

“Thanks, Cas.” Sam said automatically.

The angel simply stared while Sam’s smile slowly faded.

“Wait.” He frowned. “For what?”

You felt your stomach drop. Your eyes fluttered shut when the realization hit you.

Castiel was looking directly at you with the same puzzled expression he always wore when attempting to understand humans.

He tilted his head slightly.

“Is that not what humans say when they learn someone is expecting a child?”

The realization hadn’t reached Sam yet. You watched him trying to make sense of the words. Waiting for it to land. 

Finally his eyes widened and flicked towards you. He was puzzled by your lack of reaction.

“Did you know?”

You shrugged nervously, desperate to get a read on him.

“Know what?” Dean asked, stopping at the base of the porch steps.

Rhi’s eyes widened first. 

“Oh shit.” 

Dean looked between all of you.

“What am I missing here?”

The tension shattered when the weight of understanding finally crashed into Sam.

He laughed. A loud, disbelieving laugh that seemed to erupt from deep in his belly. The kind of laugh that only finds you safely on the other side of survival. 

“Really?”

His eyes were already shining.

You felt tears stinging your own again.

“I think so—”

You barely had time to squeak before he wrapped both arms around you and lifted you clean off the ground.

“Sam!”

His hands cradled your face when he finally set you down. His forehead pressed against yours. He wasn’t checking for injuries—physical or emotional. Not checking to see if you were falling apart at the seams. 

He wanted to confirm to himself that this was real. 

The smile that spread across his face was brighter than any you’d seen since before the Cage. There wasn’t a thread of panic there like the first time he held Willa.

After everything this world had thrown you two, there wasn't a shred of fear or hesitation anymore. 

Summer was boiling on the Kansas prairie. The only reprieve was in the evenings. The setting sun and gentle breeze made the heat more bearable. The rhythmic creaking of the porch swing punctuated the swelling chorus of cicadas. You and Sam were settled on the swing with Willa in his lap while you showed her the strip of ultrasound pictures. Trying to explain to her that the tiny black and white blob was her new sibling. 

Walker laid with his head between his paws on the porch. Releasing a deep sigh as he stared down the driveway bathed in golden light. Always on alert for intruders but letting his eyes gently shut while he baked in the glow.

The door creaking open behind him made him sit up. He slowly pushed himself up to watch Dean and Rhi step onto the porch, continuing a conversation they had started inside. 

“Ha, remember the last time you tried assigning me to research duty?” 

“Yeah! You put yourself in the hospital!” 

She stopped, her jaw fell slack in disbelief, while Dean continued down the steps with a cocky smirk. 

Walker’s head snapped back to the sound of Willa’s whimpering cry. She wiggled out of Sam’s lap to plod after Dean, gently nudging Walker out of her way. 

“Sorry kiddo.” He scooped her up and perched her on his bicep. “Gotta stay here.” 

He peppered her with kisses before handing her back to you. 

“We’ll be back in a few days.” 

“Be careful.” You said warmly while settling Willa on your lap. 

“Always am.” 

Dean smiled and scratched Walker between his ears. Walker watched as he joined Rhi at the bottom of the steps and they crossed the yard.

The familiar black car roared to life. He tilted his head as it disappeared down the gravel road and beyond the trees. For a moment, he continued staring after it and watched as the dust settled back onto the road.

The creak of the porch swing caught his attention. He watched as you stood up awkwardly and moved towards the front door to start dinner. 

He finally turned away from the empty driveway and walked back toward the porch swing. With a satisfied huff, he settled onto the warm boards and rested his head between his paws.

The familiar voices behind him blended into the evening chorus of cicadas. 

His family was home.

And this time, everyone who left would come back.

A/n: It's crazy that I started this fic when I was eight months pregnant with my daughter, and now I have an almost-three month old who's asleep on my shoulder right now.

It was so fun to learn and grow as a writer, and I hope you enjoyed! <3

My current taglist was made just for Cruel World. If you'd like to join my taglist for supernatural or other fandoms, fill out my form

𝙲𝚛𝚞𝚎𝚕 𝚆𝚘𝚛𝚕𝚍 𝚝𝚊𝚐𝚕𝚒𝚜𝚝:

@ambiguous-avery , @insensiblelimerence , @samiwinchester444 , @staley83, @little-rose-universe , @ferncloud0191

𝚂𝚞𝚙𝚎𝚛𝚗𝚊𝚝𝚞𝚛𝚊𝚕 𝚝𝚊𝚐𝚕𝚒𝚜𝚝:

I can’t believe it! The final chapter of the fic that brought us together 🥺❤️ It might be over, but there’s no way you’re getting rid of me, bestie 🤪

Chapter 8: Wish I Could Erase It, Make Your Heart Believe

Pairing: Soldier Boy x f!Reader, Reader POV

Summary: With a birthday printed on your wrist that happened over a hundred years ago, you always thought that you were cursed to never meet your soulmate. But when you finally meet the man that's supposed to be the other half of your soul, you wonder if the stars were wrong, and wonder how this man was meant for you. Reader is Hughie's sister, is not a supe, and is a Literature Professor that gets dragged into the middle of things. This fic takes place in an AU set loosely after Season 3 and does deviate from the plot of The Boys

Tropes: Soulmate AU, Little bit of Grumpy and Sunshine, Age Difference (Reader is in her 20s), Forced Proximity, Protective Ben/ Soldier Boy, Jealous Ben/Soldier Boy,

Warnings: Self Deprecating Thoughts, ANGST, Sexism/Homophobia (It's Soldier Boy), References to Sex, Cursing, Sexual Thoughts, Sexual Inneundo, Soldier Boy being Soldier Boy, Loneliness, Longing, Basically the reader just wants to be loved, Reader wears glasses?, Soldier Boy might be a little OOC.

Word Count: 6.2K

Song Inspiration For Chapter: Bad Liar by Imagine Dragons, title of chapter taken from this song!

Note: This is told from Reader's perspective. Any references to the reader is made using you or your. There is minimal use of y/n. I tried my best to proofread, but nobody's perfect. If you don’t like, don’t read, but if you do like, you’re my favorite!

Internal Monologue Is in First Person And Is In Italics

Main Masterlist

Series Masterlist

A/N: Yes, the rare potato miraculously appears rearing her head to drop another steaming pile of angst.

@lunaleah @glitterspark

@n-o-p-e-never @j2ash @xxmusic13luverxx

@happilygoldenvortex

@nommingonfood @deans-spinster-witch @kellyIs04 @goosy-goose @whitepearl

@coventina2001

@luckynibblz @andrianasinger

CHAPTER 1: 1988

CHAPTER 2: 1992

CHAPTER 3: 1995-1996

CHAPTER 4: 1998, I 06/23/26

CHAPTER 5: 1998, II

CHAPTER 6: 1998, III

Suggested listening: ▶︎•၊၊||၊|။||||။၊|။• American Teenager ▶︎•၊၊||၊|။||||။၊|။• Crush ▶︎•၊၊||၊|။||||။၊|။• Family Tree (Intro) ▶︎•၊၊||၊|။||||။၊|။• House in Nebraska

Cruel World: Chapter Eighteen

Everything was perfect—you were about to welcome a baby girl into the world and finally leave the life of hunting behind. Sam was supposed to have it all: the house, the family, maybe even a dog in the backyard. But before the three of you could begin your new life in an old craftsman home on the prairie, the apocalypse arrived.

All Sam had to do was lock Lucifer in the cage…

Pairing: Dean Winchester x fem!OC

WC: 3K

CW: 18+ MDNI, canon violence/weapons/firearms/injury, language, slow burn simmer, Dean being charmingly self deprecating, some implied DV themes, well-earned fluff

A/n: Big shoutout to @winchesterfields67 for work shopping this OFC with me!

Cruel World masterlist

“Share my body and my mind with you, that’s all over now. Did what I had to do, I found another anyhow ” - Cruel World, Lana Del Rey

Being on the road normally had a way of setting Dean’s mind straight. Hunting was second nature to him. This wasn’t hunting. These people weren’t Sam, or even Castiel.

Even a little rusty, Dean could still take down a few vampires or a vengeful spirit on his own. Capturing and transporting a living werewolf wasn’t just difficult—it was wrong. But he was doing it for you. Well, he was really doing it for Sam, so that he didn’t have to. Sam actually had something to lose.

How Sam had ever run with a crowd like this, soulless or not, was beyond him. Hunting in groups relied on trust, and he didn’t trust them. Even if they insisted they were family. Resurrected kin or not, they were strangers to him.

Crowley’s orders were simple—bring it back alive and try not to die.

The house was dark and quiet when Dean pulled in and parked behind the team’s van. They were already standing around waiting impatiently for him.

“About time,” Gwen purred.

“Let’s just get this over with.” Dean rolled his eyes and loaded a magazine of silver bullets into his 1911. He didn’t trust these people enough to believe they’d prioritize his life over capturing the werewolf. The silver bullets were for his own peace of mind.

The old house was the last known location of the recently turned monster. Dean and Samuel entered through the front while Gwen and Christian secured the perimeter.

“So,” Samuel began, his eyes carefully scanning the interior of the decrepit building, “have you heard from your brother?”

“Nope.” Dean answered quickly, drawing a humorless laugh from Samuel.

“That was a rhetorical question, son.”

Dean side-eyed him while keeping his weapon trained on the shadowed corners.

“The Sam you knew is long gone. That’s all you need to know.”

Before Samuel could continue, a commotion outside drew both men back toward the front of the property.

“Don’t fucking touch me!”

Dean’s eyes landed on Christian struggling to keep a young woman in a headlock, one arm locked tightly around her waist. She bit down hard on his forearm, drawing a pained growl from him. Christian dropped her immediately.

The woman stumbled back and drew a small blade from inside her boot, holding it in a steady, tactical grip despite the tremor in her hand.

Dean hollered in an attempt to break up the confrontation, but it was almost pointless.

“The crazy bitch bit me!”

Christian drew his sidearm and trained it on her.

She didn’t even flinch.

While she looked absolutely feral, Dean knew she wasn’t a monster. Any werewolf would be raging, trying to tear everyone limb from limb. Her anger was controlled. Directed.

“Everyone RELAX!” Dean boomed.

Christian reluctantly lowered his pistol, but his gaze remained fixed on the mystery woman. Dean slowly holstered his own weapon in an attempt to put her at ease. She didn’t loosen her grip on the knife, but she did lower it to her side.

For the first time, Dean actually looked at her.

She was young, but old enough to have experience. Clearly she knew how to defend herself. She dressed like a hunter—a worn leather jacket and faded jeans that complemented her figure while still being practical. Her dirty-blonde hair was tied back in a loose braid, with several strands escaping during the struggle.

She wasn’t the kind of woman who immediately caught your eye in a crowded bar. But once you noticed her, it was impossible to look away.

That was where Dean found himself now.

“What’s your name?”

Her eyes flicked toward him before continuing to scan the area.

“None of your fucking business.”

Dean visibly recoiled at the bite in her words.

Gwen stepped forward, saying something antagonistic that Dean didn’t quite catch before the woman took off.

Out of instinct, he followed her. Samuel stopped him briefly. “We’ve still got work to do—”

“I’m not just leavin’ her out here alone.” Dean brushed past him and continued after her.

For some reason, she reminded him of you. He hoped that if you were ever in her position, somebody would care enough to make sure you were safe. When he finally caught up, she had already picked the lock on the van. Instead of hot-wiring it and driving away, she stood frozen beside the open rear doors. Just staring.

Inside sat a heavy-duty cage, large enough to hold an adult. Horror washed across her face. She spun around, now armed with a pistol she had likely found inside the van.

Dean immediately raised his hands and stopped where he stood.

“Who the fuck are you people? What are you doing here?”

Dean huffed nervously and did his best to explain the strange situation without mentioning that he was currently working for the King of Hell.

“That’s just wrong.” She shook her head. “They need to be put down.”

“Couldn’t agree with you more.”

Her posture eased slightly, though she remained on guard.

“I’m Rhi, by the way.”

“Dean.”

She glanced toward the Impala, then back at him as the pieces clicked together.

“Winchester? As in one of the guys who kicked off the apocalypse?”

“And helped stop it…”

Dean glanced at his boots and laughed nervously. He still carried a lifetime’s worth of shame for what he did—and what he failed to do.

“You should really get out of here. It’s not safe.”

Rhi barked out a laugh at his attempt at chivalry.

“I can’t tell if you’re serious or not. But I gotta say, you don’t live up to the hype, Winchester.”

For a moment, she looked genuinely disappointed before turning and heading toward an old Ford Bronco.

Dean frowned as he watched her leave. As the Bronco rattled down the road, he spotted a small, faded peace-sign bumper sticker on the back. He squinted at it for a moment before scoffing.

“Fucking hippies.”

Shaking his head, he turned and headed back toward the group.

“You just let her go?” Christian shot daggers at Dean while cleaning the deep bite mark on his arm.

“What was I supposed to do? Kill her?” Dean regretted even asking.

“Not necessarily.” He shrugged casually. “She might have had valuable information. Your brother never would’ve just let her go like that.”

“That animal wasn’t my brother.”

“That’s enough.” Samuel had the decency to shield Dean from his brother’s behavior. He didn’t always agree with it, but he was effective. “Let’s call it a night and regroup tomorrow.”

Dean refused to bunk with the group. A creature of habit, he settled for a shabby motel next to a bar. As long as it had bourbon and a pool table, he was a happy man.

He pulled out his phone to send you a text.

Made it to the motel in one piece.

His thumb hovered over the send button.

He backed out and opted to send it to Sam instead. He’d probably tell you. And if he didn’t, you surely wouldn’t lose any sleep over it.

Tossing his phone onto the empty bench beside him, he scanned the parking lot out of habit. His eyes settled on a familiar peace-sign bumper sticker on an old Ford Bronco.

His pulse quickened. He was relieved to see Rhi had made it out alright. The sting from her parting remark still irked him. What had she expected, and why didn’t he live up to it?

He contemplated grabbing a drink and settling on the opposite side of the bar, but her eyes landed on him the moment he stepped inside.

Rhi didn’t react the way he expected. She didn’t seem angry or freaked out. She just smirked into her drink as he took the stool beside her. At that point, it would’ve been weird not to.

He ordered a bourbon and tossed it back quickly before ordering a second. Dean stared into the amber liquid, trying to think of something clever to say.

“Awfully quiet over there, Winchester.”

She glanced at him and chuckled at the blush creeping up his neck.

“I didn’t follow you, if that’s what you’re thinking.”

“Not off to a great start.”

He gaped at her for a moment before downing the rest of his drink and reaching for his wallet. He was tired and he’d been humiliated enough for one day.

“Next round’s on me.”

She signaled to the bartender before flashing him a playful smile.

Dean learned that Rhi was short for Rhiannon.

“Yes, like the song.”

“Lemme guess. Your parents were a couple of hippies?”

She was raised in a loving home by two parents in the Pacific Northwest. She was a unicorn in the hunting world.

Her parents had been killed by a wendigo during a wilderness retreat in the Cascades when Rhi was seventeen. The rangers ruled it a bear attack.

Dean noticed the way her expression tightened when she recalled the memory.

She’d been a fiery teenager—polar opposite to her pacifist upbringing—and she refused to accept the lazy explanation for her parents’ deaths.

“So that little bumper sticker on your truck?”

Rhi smiled to herself.

“Yeah. They always had one on their station wagon. I hated it growing up.” She swirled the whiskey in her glass. “It’s different now.”

Nobody became a hunter by choice and she was no exception.

She’d gotten the same lead about the small werewolf den as Dean and Samuel’s team. That was how their worlds collided.

“I don’t get it.” She leaned back in her chair. “Who’s got the big, bad Dean Winchester by the short and curlies? You guys went toe-to-toe with the Devil himself.”

Her smile faded when she noticed his body language. The proud, imposing posture she expected was gone. His shoulders looked heavy. His expression carried more regret than confidence.

“Family?”

Dean nodded, keeping his gaze fixed on the dusty bottles lining the shelves behind the bar.

“Like I said. It’s complicated.”

“Trust me.” She snorted. “When it’s family, it’s usually not.”

She was right—he was doing it so Sam didn’t have to. 

So Sam could be there for you and Willa.

So Sam could live the life Dean had always wanted for him.

“Ma’am.”

The bartender placed another whiskey in front of Rhi.

“This is for you.”

He gestured toward a man sitting at the far end of the bar.

Dean watched the interaction and expected her to abandon their conversation.

Instead, she grabbed the glass, smiled politely at the man, leaned over the bar, and slowly poured the entire drink into the sink. Dean choked back a laugh as the smug look on the guy’s face dissolved into a glare.

His heart sank more than he cared to admit when she stood and shrugged on her jacket.

“This was nice.” She smirked. “Thanks for stalking me.”

Her words still had teeth.

Her expression didn’t.

Dean fumbled through a goodbye while she tossed some money onto the bar and flashed him one last smile.

His eyes lingered on the gentle sway of her hips as she walked away, though he noticed she never stopped scanning her surroundings. Every few steps she glanced over her shoulder, staying aware of every exit and every stranger in the room.

Hunter instincts—the same ones he lived by.

He waited a few minutes to finish his drink before finally looking around the bar.

The man who had bought Rhi the drink was gone, and somehow, that bothered him more than it should have.

He was relieved to see Rhi’s truck was still in the parking lot, meaning she’d gotten a room for the night, too.

Dropping his duffle bag on the bed, he kicked off his boots and collapsed onto the mattress. He checked his phone and saw a text from Sam.

Thanks for checking in.

Short and to the point.

Dean tossed his phone onto the nightstand and settled in to get a few hours of sleep.

He woke to muffled pounding and yelling.

His hand immediately reached for the pistol on the nightstand as he scrambled out of bed. Pulling on his boots, he stepped into the breezeway and scanned the row of motel rooms.

The guy from the bar was drunkenly kicking and ramming a door three rooms down with his shoulder.

He stumbled backward after each impact, hollering threats before throwing himself at the door again.

“Rhiannon, open the fuckin’ door—”

Wham.

“—don’t make m’hurt you—”

Wham.

Dean closed the distance quickly and fisted the front of the man’s shirt. The drunk’s hot breath hit him as he slammed him against the wall. He smelled like a sweaty brewery.

Without thinking, Dean’s fist connected with his jaw. Then again.

“What the fuck are you doing?”

He didn’t give the guy a chance to answer before driving another punch into him. The familiar ache bloomed across his knuckles as bone met bone.

The door finally swung open. Rhi slipped outside, trying to intervene. Dean felt warm hands grab his shoulder, nails digging into the fabric of his shirt.

“DEAN.”

He stopped and turned toward her, still holding the man’s shirt balled up in his fist. Her expression was a mixture of surprise and horror.

“Let him go.” Her voice was weak and uncertain. It sounded unnatural coming from her.

Dean looked back at the bruised, bloodied man pinned against the wall and felt a jolt of clarity. He yanked him away from the wall and shoved him toward the parking lot. The man stumbled backward. Mumbling a slurred insult, he wiped blood from his face and retreated.

“What the hell was that?!”

Dean wasn’t entirely sure why he’d reacted so strongly, or how he expected her to react. But he was baffled. She looked frustrated, though he didn’t miss the slight tremor in her hands.

“Did you know that guy?”

“Yeah.” She crossed her arms over her chest and stared down at her bare feet against the cracked concrete. “We used to work together.”

Before Dean could ask anything else, she cut him off.

“I didn’t need you to do that, Dean.”

“I’m sure you didn’t.” He shrugged. “But I did.”

He watched her shift uncomfortably. A blush crept up her neck and spread across her cheeks. She was embarrassed. Not because she needed help. Because a complete stranger had stepped in to help her—again.

“Well… goodnight.”

Dean caught the quiet thank you she muttered under her breath before she started closing the door.

“Wait.” He stopped it with his hand.

She spun around immediately.

“You sure you’re okay?” He rubbed the back of his neck. “I can hang out here if you want. In case that guy comes back.”

She scoffed and stared at him for a moment, waiting to see if he was joking.

“So I should invite a total stranger into my room to what? Protect me?”

“You could’ve just said no, y’know?”

Dean scrubbed a hand down his face.

“Just lock your fuckin’ door.”

He slammed his own door behind him, trying to punctuate the aggravating situation. Flopping back onto the bed, one arm folded beneath his head, he stared at the ceiling. Maybe it was the adrenaline. Maybe it was his throbbing fist. Whatever it was, he couldn’t get his eyes to stay shut. After a few minutes, he gave up and headed for the Impala.

Dean woke to a gentle tapping on the driver’s-side window. His eyes settled on Rhi standing outside with a smirk tugging at her lips and a coffee in her hand. Sleepily, he cranked the window down and squinted against the offensive sunlight.

He eyed the cup suspiciously when she handed it through the gap.

Bracing himself, he accepted it.

“It’s just coffee. Relax.” She laughed as he peeled back the lid to inspect it. “Just wanted to say thanks, I guess.”

Dean saw the warmth in her expression and the softness in her eyes.He was glad she didn’t ask why he’d spent the night in the car. Truthfully, he wasn’t entirely sure himself. She was perfectly capable of taking care of herself. Maybe it was the chance that she wasn’t. If something happened to her, it would be another layer of guilt he’d carry for the rest of his life.

“Ew, what the fuck—”

Dean nearly spit the drink back into the cup.

Rhi stared at him, completely dumbfounded.

“Tastes like I just tongue-fucked Tinker Bell.”

“Let me try.”

She took the coffee from him and sampled it herself, wondering how badly the teenage barista had managed to screw up a vanilla latte.

“That’s what you call sweet?” She frowned. “It’s still pretty bitter.”

“It tastes like a cup full of cavities.”

Rhi leaned away from the car and laughed. Really laughed. Dean noticed the way the corners of her eyes crinkled. The dimples that appeared when she smiled. The tiny freckles scattered across her nose now that sunlight kissed her face.

“Well, I’m sorry.” She grinned. “Next time I’ll get you black coffee and a Lucky Strike, grandpa.”

His heart fluttered at the idea of there being a next time.

She must’ve seen something shift in his expression because she straightened quickly and the smile faded.

“Next time?” His tone was teasing, but there was a glimmer of hope behind it.

Rhi huffed out a nervous laugh and shook her head. After a beat, she finally met his gaze.

“Yeah.” A small smile tugged at the corner of her mouth. “If you manage to track me down again.”

With that, she grabbed her bag from the ground and slung it over her shoulder. She shot him one last glance before heading toward her truck.

Dean watched in the side mirror as she opened the door and tossed her bag inside. Before climbing in, she looked toward the Impala one last time. A mess of pride and guilt kept him rooted to his seat. He wanted to run after her. Give her his number to make sure there was a next time. Instead, he watched the Bronco rumble out of the parking lot and disappear down the highway.

Once he grabbed his duffle and tossed it in the trunk, he noticed the abandoned coffee cup sitting on top of the Impala.

“Aw, son of a bitch.” He groaned, already imagining the sticky stain underneath.

When he picked it up, his eyes caught the cardboard sleeve wrapped around the cup. Written in slightly smudged blue ink was a phone number. Still perfectly legible. Dean stared at it for a moment . Then, despite himself, he smiled.

A/n: I'm a big fan of our new OFC. Let me know what you think!

Let me know if you'd like to be added to my taglist:

“This was nice.” She smirked. “Thanks for stalking me.”

Cruel World: Chapter Seventeen

Everything was perfect—you were about to welcome a baby girl into the world and finally leave the life of hunting behind. Sam was supposed to have it all: the house, the family, maybe even a dog in the backyard. But before the three of you could begin your new life in an old craftsman home on the prairie, the apocalypse arrived.

All Sam had to do was lock Lucifer in the cage…

Pairing: Sam Winchester x fem!reader, Dean Winchester x fem!reader

WC: 3.4K

CW: 18+ MDNI, description of injury, struggles with mental health (anxiety/trauma), misuse of medication, tension/repressed emotions, language, super soft smut, makeup sex?, Sam Winchester cries through sex, unprotected pinv, fingering (f receiving), creampie, mentions of past pregnancy

A/n: My posting schedule is pretty inconsistent right now as I’m taking care of a newborn, so I appreciate the patience ♥️

this was a doozy to write

Cruel World masterlist

"Because you're young, you're wild, you're free, you're dancing circles around me, you're fucking crazy.” - Cruel World | Lana Del Rey

The house was quiet—the chaotic clatter of toys and high-pitched toddler babble replaced by the static hum of the baby monitor now that Willa was napping. Sam had busied himself with the growing pile of dishes in the sink when his brother finally joined him in the kitchen. Dean settled against the counter with his arms crossed over his chest.

They hadn’t said a word to each other since the previous night. Not out loud, anyway. The brothers had the innate ability to speak volumes with a single glance.

Dean had found a few opportunities to check on you from a respectful distance in the doorway. He noticed the food and water sitting untouched on the nightstand.

“Has she eaten?” Dean’s voice cut through the oppressive silence like a knife.

Sam shook his head, his gaze still glued to the coffee mug he had now cleaned three times. “I can’t even get the dog to eat,” he huffed weakly.

“Walker’ll be fine,” Dean said, his voice sharper than he intended. “But she won’t.”

Sam’s jaw clenched, his grip tightening around the now-sterile coffee mug.

“Just gonna let her sleep?”

A frustrated sigh caged in Sam’s chest sounded more like a growl. “What am I supposed to do?” Beneath the bitterness and frustration was a thread of desperation.

“How’re ya sleeping, Sam?”

The question was rhetorical. Everyone in the house knew about his nightmares. Dean had only been back a few days and had already helped you wake him from one.

“‘Cause I don’t know if you noticed, but she’s running on fumes.”

Sam set the mug down in the sink before finally turning to face Dean.

“I know that…”

“I don’t think you do.”

Sam’s face hardened at the accusation, even if it was true.

Dean sighed and scrubbed a hand down his face, trying to tamp down the anger building in his chest. “Listen, I’m not an expert or anything.” He paused, watching Sam roll his eyes in response.

“But I’ve seen enough to know she’s been holding it together on her own since she lost you. Even when I wanted to run off and do something stupid…tryin’ to find you, she held everyone together.” His throat tightened as he remembered those first few months after Sam was locked in the Cage. “And then you came back…” He hesitated, choosing his words carefully. “Like that.”

Sam looked like a kicked puppy—a look he had perfected without even realizing it. It always softened Dean, not that he would ever admit it.

“I don’t think she dealt with any of it, Sam. Not the grief, the fear…not what you did to her when you were soulless. None of it.” He paused, giving Sam a chance to collect himself while trying not to think too hard about what you had confided in him. “She just kept moving because Willa needed her.”

Sam’s insecurity gnawed at him. He hated how selfish he felt. Part of him wanted to know what you had told Dean and why you couldn’t tell him instead. But he wouldn’t violate your trust like that.

“I didn’t know it was this bad…” Sam’s voice cracked at the end.

“That’s kind of the problem, Sammy.”

Silence settled around them like quicksand.

“I’ve never seen her like that.” Sam’s eyes turned glossy as he recalled the night before. “She was scared. She’s hurt, and she wouldn’t tell me. I-it was an accident.” He threaded his fingers through his hair as the pieces started clicking together.

You weren’t protecting yourself from him—you were protecting him from himself. From the truth about what he had done.

“She was having an anxiety attack or nervous…something.”

“It was a panic attack, Dean. I know that. Was it because of me? Did she think I was gonna…fuck—”

“Stop.” Dean watched him pace, trying to outrun the conclusion he was spiraling toward. “Don’t do that to yourself.”

Sam looked exhausted and terrified. “I don’t know what to do. I don’t wanna make it worse.”

“You need to stop punishing yourself long enough to be there for her.” Because I can’t be, in the way she needs, he thought bitterly. “She’s drowning in that room up there trying to carry all this by herself.” Dean shook his head. He blamed himself almost as much as he blamed Sam. “She doesn’t need you to fix everything. You don’t gotta be perfect…you just gotta be there.”

That finally seemed to land. Sam managed a shaky nod and tried swallowing the knot in his throat.

Dean pushed off the counter and patted Sam on the shoulder on his way out. He’d only be gone a few days, if everything went as expected, but it would feel like an eternity.

You weren’t his to protect and take care of. Not that you had ever let anyone take care of you.

Guilt and anger still churned low in his gut. I shoulda’s reverberated endlessly through his mind. With the Impala keys in hand, he hoped a few days of hunting would channel his anger into something useful.

When you finally woke long enough to form a coherent thought, the light outside was already fading. Your hip and shoulder throbbed painfully after lying on the same side for hours.

The sight of water on the nightstand reminded you how parched you were. Walker thumped his tail and lifted his head from his nest of blankets as you eagerly gulped down the room-temperature water. A few stray drops trailed down your neck, cooling your skin and sharpening your senses.

As you adjusted to your surroundings, panic shot through you when you registered the deafening silence of the house—and the fact that you hadn’t laid eyes on your daughter in nearly a day.

You were surprised by how weak your legs felt. Really, how weak all of you felt. The gnawing in your stomach reminded you how long it had been since your last proper meal. It wasn’t dinner the night before. You had made yourself a plate, but Willa needed help eating, and afterward she desperately needed a bath. Your meal had been forgotten on the table, just like it had so many times before.

Sam was alerted by the creaking floorboards and quickly moved to check on you. When he pushed the bedroom door open, you were digging through a pile of laundry for a clean shirt.

“Hey, you’re up—just take it easy.”

All you cared about was Willa.

“Relax, she’s still asleep. You need to eat. And drink. And not take anymore of these,” he said, holding up the bottle of very expired painkillers. They had been prescribed after Willa was born, but you’d barely touched them back then. Now they dulled the pain enough for you to carry her without raising suspicion about your injury.

“I couldn’t exactly go to a doctor,” you said softly, trying to soften the inevitable sting of your words.

The implication burned.

“You shouldn’t have had to in the first place. Please just…let me take care of you.” His eyes were pleading, like he needed it more than you did. For once, he wasn’t trying to dissect your pain—cutting it open, naming all the pieces, tracing them back to the source. He was simply acknowledging that it hurt.

“I don’t even know what that means.” You bit the inside of your cheek to steady yourself. “I think I just needed some sleep. I feel fine—”

“—no, you’re not. And I’m sorry I didn’t see it.”

Your shoulders visibly sagged as his words settled around you. In his defense, you hadn’t realized how bad things had gotten either.

Sam watched you fidget with the hem of the shirt you’d found—one of his, naturally. Relief softened his expression when you finally nodded gently, silently giving him permission to step in when you needed him most.

Sam drew you a bath while he made dinner. You insisted on taking a shower, but he didn’t trust your shaky legs.

When Willa woke up, you let him handle getting her out of her crib. He insisted that he’d do all of the lifting while you healed, including your growing toddler. Your heart ached to be close to her, but you agreed to finish an entire meal before joining them downstairs. You finished quickly—practically inhaling the pasta dish he brought you—not realizing how hungry you were.

Having your basic needs met left you feeling refreshed and restored. A nervous energy pulled you downstairs, following the tiny voice in the kitchen that promised to make you feel whole again.

Willa’s face lit up as soon as she saw you in the doorway. So did yours. Ignoring the red sauce staining her hands and face, you gently squished her tiny face and nearly smothered her with affection. Her tiny giggles and repeated mama’s made your heart swell.

She lifted her little arms silently asking to be picked up. Motherly instinct made you move without hesitation.

“I got her.”

Your cheeks flushed as Sam shot you a look before moving to pick her up instead.

Sam noticed the way your expression faltered and immediately regretted how abrupt he sounded.

Willa whined softly in protest and reached for you anyway, twisting in Sam’s arms.

“I know, baby,” he murmured, bouncing her lightly on his hip while his eyes flicked back to you. “Just let me help, okay?”

You hadn’t realized how much of your identity was wrapped up in taking care of everyone until your mind and body stopped cooperating with you. Even something as instinctive as picking up your own daughter suddenly felt complicated.

Your heart splintered at the sight of your child asking to be close to you and, for the first time in her life, being denied your comfort. That feeling was far more painful than the blow to your chest.

Walker began whining as Willa’s fussing continued, adding to your growing anxiety.

“Hey.” Sam nodded toward the couch.

You settled into the soft leather and listened to the rhythmic padding of tiny feet on wood floors. Willa quickly climbed into your lap and wrapped her little arms around your neck. You barely registered the pain—the corners of your eyes only tightening briefly—over the warmth and love of the tiny being in your arms. She pulled back slightly and her little hazel eyes scanned your face carefully. You didn’t notice the stray tear on your cheek until she clumsily wiped it away, using far more force than necessary and drawing an emotional laugh from you.

Normally, Willa loved to play or read her favorite books after dinner. Tonight, she just wanted to curl up in your lap and stare at you through heavy eyelids. Exactly the way she had when she was a newborn—studying your face intently, trying to memorize the expressions of the person she trusted most in the world.

By the time Sam finished cleaning up dinner, you were both asleep. Your shirt bore remnants of red sauce from Willa’s dinner. He admired that you had never fussed over spit-up stains when she was little—if anything, you wore them like badges of honor for surviving the trenches of early motherhood.

It pained him to lift Willa from your chest and she whined sleepily at the separation, immediately reaching for you again with limp little hands.

“I know,” he whispered softly while settling her against his shoulder. “Mama just needs some rest.”

Walker lifted his head from his bed and watched Sam carefully as he carried Willa toward the stairs. The old shepherd seemed reluctant to leave you alone, even for a second.

Sam paused halfway up the stairs and glanced back toward the couch.

You hadn’t moved. Curled on your side beneath the dim glow of the television, one arm still stretched across the empty space where Willa had been moments earlier. Even asleep, your body looked tense, like you were bracing for something terrible to happen.

The sight hollowed him out.

Dean’s words kept echoing in his head.

She’s drowning in that room up there, trying to carry all this by herself.

He finally understood what Dean meant—you weren’t just tired. You were exhausted in a way that had seeped into your bones. Worn thin from surviving one impossible thing after another without ever allowing yourself to stop and feel any of it.

And somehow, even now, your first instinct was still to take care of everyone else before yourself.

Willa had fallen asleep again by the time he laid her down in her crib. She stirred long enough to mumble a sleepy mama before settling against her blankets.

Sam lingered beside the crib for a moment, brushing her curls away from her face.

“I know,” he whispered. “I miss her too.”

The confession slipped out before he could stop it.

Because even downstairs on that couch, only a few rooms away, it already felt like he was losing you. 

He intercepted you as you were coming up the stairs. 

You were still half-asleep so he easily guided you towards the bedroom with a gentle hand on your back. Before you could land in the soft comfort of your bed, Sam curled his arm around your waist to stop you with almost no effort on his part. You hummed weakly in protest as he pulled you almost flush against him. 

“You should probably change.” His hand teased the hem of your shirt. 

You glanced down and huffed a tired laugh before awkwardly pulling your arms out of the sleeves. The only way the pain allowed for.

Sam’s palms landed on your hips to steady you. His gaze settled on your bare chest. You didn’t try to hide from him. He frowned and sat on the edge of the bed and pulled you close to him. His eyes flicked between the blue and purple nebula of a bruise on your chest and your sleepy eyes. 

“Did I do that?”

You sighed as deeply as you could and gently nodded. 

His eyes were glossy and he tightened his grip on your hips. 

Your hand cupped his face while the other threaded through his soft locks. “Look at me.” 

He tilted his head up while you applied some tension at his roots. You knew it was an accident. One that he couldn’t forgive himself for. Settling in his lap, you kissed him softly and he melted into your touch. You tasted salt and you weren’t sure if it was from your tears or his. His kiss turned more frantic and you tugged at the hem of his shirt, pulling it over his head 

His long arms wrapped around you tightly—almost painfully. Being pressed against his warmth soothed every ache and pain in your body. He rolled over and laid you against the mattress. Every ounce of anxiety dissolved with each pass of his hands against your tight muscles. 

Your sweet, sleepy sounds made his head fuzzy and his throat tight. You could barely keep your eyes open, but your body still hummed with need.

“Please, Sam.” 

He groaned feeling your shaky thighs tighten around his waist. 

“Y’really need to rest, baby.”

“Need you.” 

That broke his resolve. His mouth trailed down your throat, soothing the bruises with his soft lips and a quick pass of his tongue. 

You whimpered when he pawed at your breast and he loosened his grip in response. He placed featherlight kisses in the space between your breasts and muttered a quiet apology. 

“I know, it’s okay, Sammy.” 

He huffed a warm sigh against your skin, now slick with a mixture of tears and saliva. “I love you so much, Y/N.” 

His husky voice against your belly vibrated into your core. 

“I need you—now.” 

He didn’t ask questions. He just wanted to give you what you needed. His hands were shaking with restraint while he gripped the elastic of your panties and slid them down your legs, tossing them aside. 

You whined from frustration and pulled at his waistband, desperately wanting to feel him. 

He stood up and smiled at the sight of you, looking up at him with heavy lids and flushed cheeks. He quickly kicked his jeans and boxers off and settled between your thighs again. The feeling of his leaking cock against your thigh made your heart race and mouth water .

You flinched when he pressed two fingers to your pussy and parted your lips. “It’s okay—s’just me.” He cooed while you nodded weakly. His soft bangs tickled your face while he pressed his forehead to yours. Watching your expression while he slowly scissored his fingers into your tight cunt, just enough to get you ready for him. 

You whined and dug your fingers into his biceps when he finally pressed his swollen tip past your puffy folds. He stilled his hips when he was fully seated, swallowing your pretty cries and moans. “You’re so pretty, baby—so perfect for me.” 

Your hips started to rock as you chased the more of the delicious friction and pressure. 

“What do you need, honey? I just wanna make you feel good—need to.” He was desperate and rambling, pressing hot open-mouth kisses on your neck. 

“Fuck me—please.” 

You yelped when he snapped his hips and your walls struggled to accommodate his girth. 

“Shhh, I’m sorry baby, m’so sorry.” His breath was warm on your neck, his words laden with emotion. 

Feeling the tension in your velvety walls, he slowed his thrusts and pulled back to watch your face while he bottomed out. Your face softened when he started petting your swollen clit. 

“There she is.” He purred lowly against the shell of your ear. “Come for me, baby.”

He groaned when your nails bit into his skin and your cunt spasmed around him. You felt his cock twitch as he buried himself to the hilt, filling you up with his spend. 

“Sam—“ you groaned painfully when he relaxed against you. 

He shifted his weight back, apologizing and peppering your chest and neck with kisses while you both came down. 

Your heart started to race when you remembered you didn’t have your IUD anymore. Sam was still on top of you, slowly going soft but keeping you full of him. 

He noticed a shift, a micro expression. The way your soft features tightened. “What’s wrong?” 

Your throat tightened while you wiggled out from under him. He didn’t do anything wrong. You just weren’t ready. Neither of you were ready. 

“Hey—“ he tried reaching for you but you shrugged him off. 

“I’ll be right back,” you muttered under your breath after pulling a shirt on and slipping out of the bedroom. 

This was exactly how it happened the first time, when you got pregnant with Willa. 

Realizing you forgot to wear a condom after getting caught up in the moment. Quickly rushing to the bathroom and taking a shower, knowing how pointless it was. 

Your chances were low—you only had the IUD removed a few days ago. It wasn’t the right time in your cycle. You opted to skip a shower, but still took time to clean yourself up. 

Walker had taken advantage of the door not latching to creep into the bedroom and hop into the foot of the bed. On your side, naturally, as there was more room for him. 

“Don’t get comfy, bud.” Sam leaned forward to scratch between Walker’s ears. 

You came back a few minutes later looking more relaxed. 

“If I catch one paw to the leg you’re outta here.” Walker stretched out even more, earning a laugh from both of you. 

“You alright?” Sam studied you nervously.

“Yeah, just…not ready.” You returned a nervous look gauging his reaction. Hoping he wouldn’t silently implode or take it as a rejection. 

“Definitely not”. He nodded, almost over confidently. Trying to compensate for the tightness in his voice. 

You slid under the sheets, curling up at his side with his arm draped around you. 

“I love you.” He said softly, pressing a kiss to the side of your head. You echoed him before sleep quickly dragged you under. 

Sam watched you for a while, smiling at your quiet snoring. It was just one of the adorable quirks he’d become accustomed to over the years, that he struggled to fall asleep without. 

Once he was sure you were asleep and properly covered up, he slipped out of bed and walked carefully towards the door. He gazed back at you for a moment, looking to see if you stirred. Satisfied, he gently closed the door behind him, leaving you and Walker to rest.

A/n: Shoutout to @winchesterfields67 for always being my beloved sounding board <3. The next chapter is in the works!

Let me know if you'd like to be added to my taglist:

𝕪𝕠𝕦 𝕝𝕚𝕜𝕖 𝕥𝕠 𝕣𝕒𝕘𝕖, 𝕕𝕠𝕟'𝕥 𝕕𝕠 𝕥𝕙𝕒𝕥

Pairing: Dean Winchester x fem!reader

CW: 18+ MDNI, rough sex (manhandling, marking, hair pulling, etc.), edging, forced orgasm, overstimulation, dom!Dean, sub!reader, unprotected pinv (don't do that), creampie, cum eating, pet names, wow this went off the rails y'all

WC: 2K

A/n: I love this request and thought angsty season 4 Dean was perfect for this. Title is from Is This Happiness by LDR.

The motel door slamming shut made you jump. Your eyes shot up from your laptop and adjusted to the low light in the room, finally settling on Dean. Just Dean. Yanking open the refrigerator door and grabbing a beer before slamming it closed. Your eyes followed him as he paced, each footstep punctuated by a creak of his boots on cheap linoleum. 

“I’m gonna kill her…fuckin’ Ruby.” 

You released a slow breath through your nose. 

“That answers my question.” You muttered to yourself.

That was why he came back without Sam. The tension between them was unbearable. Sam had promised he was done with Ruby. Done using his ability to exorcise demons. 

Done drinking demon blood.

You slowly closed your laptop with a quiet thud before standing up and padding towards him.

He was sitting at the edge of the bed with his elbows braced on his knees and his jaw clenched tight. 

You might as well have been invisible standing in front of him. His eyes didn’t waver from the amber colored bottle in his hands.

A nervous sigh escaped you as you removed the bottle from his hands and set it on the table before settling in his lap. His brow furrowed like you had grown a second head. 

“—the fuck?” 

He was stunned silent—almost. 

You laced your fingers loosely around his neck and did your best to meet his gaze. The man was intimidatingly pretty. Even when he was furious. His intensely green eyes were dark with rage and made you shiver.  

His rough hands landed on the plush of your hips, and you weren’t sure if he was about to throw you off or pull you closer. You could see the battle raging in his mind.

You’d stopped expecting anything from Sam as he got sicker. It made the disappointment sting less when he let you down. But Dean wouldn’t give up on him and it was easier for him to blame Ruby—as if she had the ability to change. 

“I’m not good for you right now, sweetheart,” he drawled, still not making any attempt to push you away. If anything, the pads of his fingers pressed harder, holding you tighter. 

“I know,” you answered softly. Dean was always gentle with you, afraid of taking more than he deserved. Treating you like you were breakable, which is why he didn’t let you hunt with him. You were always on research duty. Stuck at whatever shitty motel or small down library he left you at. 

His fingers trailed down your thighs, causing goosebumps to rise in their wake. You didn’t flinch, even though he felt anger simmering beneath his skin. He was surprised that you didn’t recoil from the heat that was surely radiating off of him. 

“Last chance to stop me. I won’t be mad.” 

Your hips rolled slightly, enough for him to clock it. You pulled him towards you, fingers applying pressure at his roots, enough to draw a pained hiss from him. Your kiss was molten—full of desire and devotion. Telling him exactly what he needed to know.

If you were breakable, you wanted him to be the one to break you.

His hands squeezed your soft thighs and he stood up with you wrapped tightly around him. You gasped when your back hit the old wood paneling on the wall. His mouth abandoned yours and trailed under your jaw where his teeth pinched and dragged against your skin.  Your neck was surely a mess of spit and small bite marks, but feeling him lose control was worth it. 

Bringing one hand between you, he shoved it past the waistband of your shorts and pressed his fingers against the damp cotton of your panties. His breath came in hot puffs against your neck while he pulled the fabric aside and ran his fingers through your slick. 

“Fuck baby—you’re so wet f’me.” He groaned while his thick fingers teased your tight entrance. 

You bit your lip trying to muffle a cry when he plunged two curled fingers into your spasming cunt. He felt you start to clench after a few rough thrusts, his fingers hit your g-spot perfectly, in a way yours never could.

He pressed you harder against the wall so he could brace himself and finger fuck you harder. The way his palm nudged your sensitive clit was bringing you towards the edge. He withdrew his hand making you whine and pulse around nothing. 

“Dean..” you cried and let your head loll back against the wall. 

Your cheeks flushed when you saw him suck your wetness off his thick fingers. He gave you a cocky smile and wink. He knew exactly what he was doing to you.  

“Sorry sweetheart—you gotta wait.” 

Before you could protest his cruelty, his mouth was on you again. His tongue lapping up the precious little moans he loved so much. 

You yelped when he pulled you away from the wall and dropped you on the mattress. He stopped for a moment and enjoyed the sight of you sprawled out in front of him. Nothing but love in your eyes. All for him. 

Your eyes were glued to him as you watched him shed his layers, drinking in every beautiful ridge and valley, the way he almost seemed to glow in the yellow lamplight. Your cami joined the growing pile on the floor. Just as you were undoing the clasp on your bra, he roughly peeled your shorts and panties off in one pull, dragging you closer to him in the process.

“You were taking too long,” he said before stuffing his thick digits inside you again. His warm mouth latched onto one of your nipples, already hardened by the cool air in the room. You were closer than you thought after your robbed climax and Dean knew it. His tongue worked your sensitive peak with expert precision, his teeth providing enough pressure for you to arch your back off the mattress.

“Please don’t stop.” 

His eyes flicked up towards you. The normally beautiful green was almost completely dark with lust. He released your nipple with a wet pop.

“Not yet.” 

You were wondering what you had gotten yourself into. Normally, Dean would make you come as many times as he could before sinking his cock into you. 

He gripped your hips tightly and flipped you onto your belly and pulled your hips back. He took a moment to admire the view of your perfect ass. Your adorable little dimples. The smooth curve of your waist. Your wetness glistening on your thighs. He gripped the base of his cock and gave it a few slow pumps, drawing a bead of precome out of the tip and working it down his length. 

He finally notched himself at your tight entrance and you whimpered. He felt so thick and heavy against you.

Running a rough hand down your spine, he pressed your face and chest deeper into the mattress. 

When he finally sank into you, the stretch was almost blinding. Your body tried to shift forward, but his grip on your waist kept you firmly in place. Exactly where he needed you. 

The mattress absorbed most of your noises, and Dean wasn’t having it. He gripped a handful of your hair and pulled—not enough to hurt. Just enough for him to hear your little whining mewls.

“Perfect little pussy. Squeezin’ me like a vice.” He growled as he bottomed out, feeling your walls flutter to accommodate him. He pulled out slowly, watching your pink ring clinging to him, before ramming back into you and forcing the air out of your chest.

Between the sound of skin slapping, made obscenely wet from your arousal, and your pornographic noises, there were going to be complaints made to motel management. 

His hand slid underneath you, between your trembling thighs, and petted your clit in time with his thrusts. Your walls started to flutter and he felt you getting wetter. He knew your body well enough to know you were about to fall apart. 

“Getting close?” 

You could hear a smirk in his voice. All you could manage to do was hum. There was definitely a small puddle of drool forming on the fabric below you. 

“I wanna feel you come, sweetheart.”

That was all you needed for your vision to go white and waves of pure euphoria to course through your body. He groaned while your velvety walls pulsed around him. It took every shred of his willpower not to join you—but he wasn’t done with you yet. 

You must have blacked out. Somehow he managed to turn you over and cage you underneath him. Hooking your legs over his arms, he folded you in half into a mating press.

“You’re taking me so well.” He purred as he admired how absolutely ruined you were underneath him. His palms pushed your thighs even wider to allow him impossibly deeper. 

 “m’so fucking full, oh my god.” You couldn’t think straight with the way he stretched your cunt. 

You felt every curve and vein. Every time his swollen head kissed your cervix. The slight curve that pressed on that special spot inside you, more sensitive from your first orgasm, driving you towards your second.

You were so sensitive, clit still swollen, when his calloused pad returned to the sensitive bud. You whimpered and tried uselessly to wiggle away from the overstimulation.

“I know it’s hard, but you’re gonna give me another. Just a little bit more.” His voice was warm and smooth like butter, melting you from the inside.

He was right, and he just kept fucking you through it. He knew your body better than you did. 

Seeing the pretty white ring at the base of his cock, wetness glistening on your thighs, made his thrusts stutter.

“So perfect f’me…my perfect girl…mine” 

He groaned as he bottomed out one last time, painting your womb with thick ropes of his spend before resting his forehead against yours. 

His expression was softer now as he searched for any sign of discomfort—worried that he might have gone too far. You were, in his mind, something else he needed to protect. Something breakable. 

He was relieved to see you meeting his gaze. No pain or fear in your eyes because he had let himself lose control. Still, he slowly eased your legs down, allowing you to take a full breath that you didn’t realize you needed.

You relaxed into his touch while the same hands that had folded you in half were gently massaging your aching hips. His thumbs rubbed soothing circles where his grip had been bruising. 

Once he started to soften inside of you, he watched as he slowly withdrew from you, groaning as his release started to leak. He watched you clench at the loss, causing more to seep out. With two fingers, he quickly pressed it back into you with a cocky grin, seeing how sensitive you were now. 

“fffuck—DEAN!” Your back arched as he curled his fingers slightly. 

“Shit, honey. I wanna feel you again.” He withdrew his fingers, now coated in your combined juices, and rubbed your puffy bud mercilessly. He tightened his grip around your thigh and pulled you closer, angling your hips upward on his lap to keep your cunt full of him. 

Your legs trembled with every pass over your clit while his lubed fingers tickled your g-spot perfectly. You were so fucked out that his name was the only word left in your vocabulary. 

When you came again he was gentler, slowing his fingers to guide you down without overstimulating you. This was all about you now.

Your eyelids were leaden. Nerves overwrought. Body loose and heavy like you could melt into the mattress. 

“Hey—look at me.” 

You managed to open your sleepy eyes a crack and smile weakly, humming in response.

“Was that too much?” He rubbed his neck nervously wondering if he had pushed you too hard.

“Hell yeah it was.”

 His stomach dropped. 

“…but in the best kind of way.” 

He huffed a nervous laugh. “You’re gonna be the death of me, sweetheart.”

(Sam Winchester x female reader x Dean Winchester)

Summary A case leads you to a Supernatural convention. You can't help but tease Sam and Dean about their notoriety, but then it turns out you are in the books, too. And there's some stuff in there you don't want the brothers to know about. CWs Sexy thoughts but no sexy actions. Supernatural book series. Conventions. Awkwardness. Cheesy book covers. Secret crushes. Rated Teen. 3.7k words. AN There's a spiritual, more explicit sequel, Horror is one thing, but being forced to live bad smut? Enjoy! Or cringe. Either is fine. 😄

Sam x reader x Dean masterlist ⏐ SPN masterlist

“It’s so… lifelike,” you say, moving your head a little so you can see better through the reflection of the glass.

“Very funny,” Sam says, and his voice tells you that he doesn’t think it’s funny in the slightest.

“I mean the hair, the shoulders, the ripped jeans, blood-dripping axe, the…”

You narrow your eyes, trying to see. “Is that a harmonica?” you ask. Sam leans over you, so close you can smell his aftershave.

“I think it’s supposed to be a knife?” he says, but he doesn’t sound sure.

“I think it’s a harmonica,” you say, turning around and he leans back, while he looks at the glass case behind you with pain in his eyes. “I mean you’re famous for your mouth organ skills,” you conclude, grinning proudly at making that sound as dirty as it does.

Sam doesn’t appreciate the joke, his face full of horror while he does the cutest little pout.

“I hate this,” he says, still looking at the book in the case behind you. Supernatural, by Carver Edlund. Whichever volume this is, it has Sam and Dean on the cover in worrying and completely impractical states of undress, fighting hordes of what are meant to be demons but look more like gremlins.

It has been your utmost pleasure in the last fifteen minutes to torture Sam with how he is portrayed on these covers. They’re ludicrous and over-the-top but if anyone could pull off the no shirt, ripped jeans, harmonica playing look it would be Sam. Or Dean.

Speaking of, he walks up in just that moment. “I hate this,” he says, echoing his brother. You don’t. You actually love this.

❤︎︎ summary. you love dean, but he’s too old for you and he’ll never feel the same.

❤︎ contents. f!reader, sfw, unrequited love, alcohol, drunken confessions, age gap (reader is 24 + dean is late 40s/early 50s), angst, hurt/no comfort, jealousy, pet names (sweetheart, kid), slightly misogynistic thoughts from reader bc she’s jealous lol, canon divergence — 5.1k words

❤︎ notes. inspired by this ask. it was just gonna be a short fic but it got a little out of control haha.

You hate that Dean flirts with other women right in front of you. 

It’s probably not on purpose. He doesn’t think about your feelings enough for him to be that calculated. He’s not searching the bar for the perfect victim, trying to choose a woman that will make you seethe with jealousy and question your own self-worth. 

You doubt he’s thinking about you at all. 

The smile Dean shares with them is always different than the one he gives you. It’s not as warm, not as familiar, but there’s something secretive about it, lust curling the corners of his lips into a grin as his eyes darken a shade. He always leans forward, whispering words to them that’ll make them feel special, even though they’re just one more notch on his belt, another set of heartstrings he’s got wrapped his finger. 

Dean never looks at you like that, and it kills you because you can’t understand why. 

❤︎︎ summary. dean's married—he's been married for years. you want to let him go, you wish you could let him go, but something always has you crawling right back into his arms.

❤︎ contents. f!reader, complicated/toxic relationship, infidelity, canon divergence, secret affair, exes, reader is a hunter, dean & reader are both in their 30s, angst, hurt/comfort, pet names, references to depression & addiction, dean/lisa are married, smoking, emotional manipulation (kinda) — 6.0k words

❤︎ notes. crossposted from ao3. just for some quick context, this takes place a few years post-s5 finale in an au. bobby & cas are dead and sam is still in the cage. dean & the reader are both hunters that met in their early 20s, but they split after sam died. dean has been married to lisa for two years.

The worst thing about change was that beautiful things never lasted.

Nothing lasted, really. Time would make a victim of every living thing, and eventually, the Earth would purge itself of the rot humankind had caused, erasing the evidence that you’d ever existed at all.

Time was, perhaps, the most consistent of all elements. Change came steadily, regardless of whether one sought it out or not. It was unavoidable, even in the smallest of ways. A song that you loved could be soiled in a moment, ruined by the careless words of another. A film with critical acclaim could turn sour, when the culture changed and the lines within no longer fit the social scene.

Things would be forgotten, lost to the grip of eternity. Memories, even those that were promised to remain forever, would eventually be lost.

That was just the way it was.

Dean loves her. He knows it. Not always — there was a time before her, long ago. Dean can’t remember exactly when, but it was when Sammy was still shorter than him and had a little height on her. But since then, he’s loved her.

He’s glad to have met her so early in their lives; he’s glad to have had the chance to cling onto her for so long that she doesn’t have any other options but staying at his side, now. Now, Dean doesn’t think she’d even give him a glance.

Not because it’s him, or anything, but because he’s a dude. Probably, also because of him, honestly. She puts up with a lot of his gross man stuff because he’s Dean. At least, that’s always her excuse. She’ll complain about some guy, and scoff under her breath about ‘men’, and Dean will look a little offended, so she’ll pat on his arm and say, “No offense, you don’t count, De.”

He used to actually get kind of upset because he is a man. He’s very manly, and very much a guy. Now, he just pretends to be so he can ask, “Then what the hell am I?”, so he can hear her say, “You’re my Dean.”

She doesn’t really willingly talk to guys that aren’t Dean or Sam. Ever. Every bar, she rolls her eyes at free drinks, but takes them anyways, and turns back to finish her conversation with Dean about what famous cowboys they would be. He’s Clint Eastwood, unless she’s there in this universe, then he has to be the Wild Bill Hickok to her Calamity Jane, obviousy. Having a smoke outside, she refuses a guys lighter and looks to Dean by her side instead, and continues talking about how she would join the Dark Side, but only if Darth Maul asked, or Dean had already joined. Dean, who doesn’t smoke, but carries the lighter he took from Bobby’s for her.

Never once has Dean seen her enjoy a conversation with a man outside of himself, Sammy, or Bobby. She always looks to him for saving, too. He loves when she does that. Loves that she knows he’s always there for her to do that, even if it’s just throwing an arm around her shoulder to give some guy a hint. He loves getting to throw an arm around her shoulder.

He does it a lot, too. Not just for that, either. They sit in the same booth at every diner Dean pulls the Impala into, whether Sam’s there to take up the other side or not. They share beds, definitely just because it’s cheaper, and maybe even cuddle sometimes, when Dean somehow magically pulls her over to replace the pillow he usually holds. They watch cable screenings of movies together, on shitty leather couches, and always end up toppled over eachother with the comfy blanket she brings on every hunt. He likes when she folds first, and crawls onto his chest and in between his legs, but he’ll never complain about resting his head on her chest.

They touch a lot. They giggle and shove, and rub backs, and squeeze arms, and twirl hair, and grab waists, and maybe even hold pinkies and interlock legs under tables. And he’s allowed to have all of that with her cause he’s her Dean. Even all Sammy gets is a side hug and a high five here and there.

She doesn’t have much family left, and she doesn’t talk to whoever is. Her neighbor, though, some old lady with a husband she hates and an oddly large amount of grandchildren, loves her.

She’s never home much with hunting, but when she is, her and her neighbor will smoke a cigarette on the porch together with a cup of coffee. The first time Dean met this lady was interesting. When he pulled into her driveway the sun was barely up, but it was already glistening against the skin of her legs, and the rest of what was peaking out from under her silky robe.

She grinned, and took a drag, smoke pooling from her lips while he walked over.

“Look at this handsome man,” Her old neighbor chimed, waving a finger. “Thought you didn’t have no boyfriend.”

“I don’t,” She laughed right back. He’d been close enough to touch then, so she gave his forearm a little squeeze. “Hi, De.”

“Hey, Sweetheart.” He grinned back down at her, eyes rimmed red and sleepy from the long car ride, but still just happy to take in the sight of her.

“Sounds like boyfriend talk to me, there, honey.” The old lady sipped on her coffee, eyeing him.

“Nah,” Her hand moved up further, giving his bicep a pat. “This right here is why is don’t need one. Not that I ever really wanted one in the first place.”

He thinks about that a lot. And about afterwards, when she called him baby, and stood from her patio furniture to lead him inside. How her hand was warm on his bicep, and rubbed his back to sleep while she read a cheap novel until he woke back up.

She makes loving her easy, but Dean would still do it if it was hard. She never asks for much, but he always knows what she needs. When they get back to the motel room after a long day, and she flops on the bed on her tummy, Dean knows she won’t want to eat anything but pretzels or crackers, sometimes toast, for a while until her stomach will feel better. He’ll tell her he’s going for a drive and show back up five minutes later with a Ginger Ale.

When she scrolls through the TV channel guide before pouting and tossing the remote in his lap, he can tell there aren’t any Dr. Sexy reruns on, so now it’s up to Dean to find an acceptable movie. When a hunt goes bad, and her eyes go all spacey, Dean knows it’s time to go lay in bed. Not necessarily go to bed, just be in bed. With Dean. To lay together, under her huge, comfy blanket. She likes watching cartoons, then, or just talking. The two of them, they can talk about anything for hours.

Sometimes, she likes to lay on his chest. Dean will already be in bed, channel surfing, when she strolls from the bathroom in his old hoodie and soft pj shorts. She’ll crawl into the bed, and curl up with her head on his abs, facing the TV.

Once, halfway through an episode of Scooby-Doo, she shuffled around to face him.

“Do you think it’s weird I never try to get with guys?”

It threw him off pretty bad. Never once, has he ever really thought about it. She just…didn’t do that, and that was that. End of story.

“No. Why would I?”

“I don’t know,” She shrugged. “Just…when we went to the Roadhouse awhile ago and I was hanging out with Jo, she wanted to talk about boys and stuff. I told her you’re the only guy I tolerate — besides Sam, obviously, but — she kinda made fun of me a little. She was just joking, y’know, but I guess it just made me think.”

“What did?” His eyebrows were crinkled, and his pretty green eyes showed just how truly lost he was.

“I just never realized that it wasn’t normal for that to not be appealing. The whole…sleeping with a random guy thing. That’s probably why i’ve never had sex.” She said it like it means nothing, like it’s the most normal thing in the world.

“…You’re a virgin?” His eyebrows moved all the way up, and his mouth didn’t gape, but it was still open when he finished. The prettiest, smartest, most hilarious woman he’s ever known — is a virgin.

“Well, yeah,” She shrugged again. “Why would I wanna have sex with some random dude who won’t even get me off? I’d rather just do it myself. Besides, I’d want it to be someone I trust, and I only really trust you that much.” Then, after staring him in the eyes and spilling the one thing he didn’t know about her in the most casual tone possible, and saying, out of anyone in the world, she’d only want to have sex with him, she turns back around and watches the rest of the Scooby episode until she falls asleep. Her head is still on his tummy, moving up and down with his breath, and her hand lays in front of it, a little too close to his waistband.

They’ve been different after that. Not much, but enough for Sam to notice. Jo, Ellen, and even Bobby, notice, too when they’re around.

All their soft, small touches that could’ve maybe passed off as just something sweet between good friends now linger. They fully hold hands, all the time. No more pinkies linked under tables, but now, swinging hand in hand everywhere they go. Kisses on the cheek are mandatory when one is leaving for more than five minutes without the other, whether it’s to a different state or the next room over. Hugs are constant and never ending. She receives a minimum of four Dean Winchester given piggybacks on a weekly basis. Playful pushes turn into tickles and giggling and careful tackles onto beds and big bear hugs. Basically, they’re just fucking insufferable.

They say I love you, like they’ve been doing it for centuries. To Dean, it feels like they have. Everything is just so easy with her, that there’s no way he can’t say it back. It’s not like he’s lying, either way. It kinda scares the shit out of Sammy, though, the first time he catches it.

Dean and Sam were just going to the library, she was staying back in the room with an upset stomach because Dean wouldn’t let her go. He’d had gotten her Goldfish and a Ginger Ale already, had her propped up in bed with the best pillows in the room and Cake Boss ready to shine (Dr.Sexy wasn’t on).

Sam had already been waiting by the door, annoyed and impatient when it happened. He was about to start sighing and grumbling for Dean to hurry up when the older brother leaned back into her side, after just finally being convinced to leave it, and pressed a kiss to her temple.

“Call me if it gets worse or somethin’, alright? We’ll be back in a minute.” Her hand curled up, into his hair, basically petting him.

“I know, De,” She kissed his cheek. “Thank you.”

“Nothin’ to thank me for.” He got all bashful, grinning like he was on top of the world.

“Alright, get out of here,” She laughed, and gave him a push. “Stop making Sam wait.” He moved away, finally, and just as the two were about to shut the door behind them, she shouts for Dean. “Love ya!”

He sticks his head back in, grinning so fucking sickly sweet it almost made Sam’s stomach start to hurt too. “Yeah, love ya, girl,” He closes the door, turning back to Sam. “Hurry up, Sammy, we’re running late.”

Yet, both of them will still claim they’re ’just best friends’. What absolute bullshit.

Cruel World Masterlist

Everything was perfect—you were about to welcome a baby girl into the world and finally leave the life of hunting behind. Sam was supposed to have it all: the house, the family, maybe even a dog in the backyard. But before the three of you could begin your new life in an old craftsman home on the prairie, the apocalypse arrived.

All Sam had to do was lock Lucifer in the cage…

Pairing: Sam Winchester x fem!reader, Dean Winchester x fem!reader, Soulless!Sam x fem!reader

CW: 18+ MDNI, TW!, smut, angst, grief & loss, descriptions of canon-type injuries, language, main character death, language, sexual tension/slow burn

I don’t want to give too much away, but I will provide CW for each chapter 💕

“Share my body and my mind with you, that’s all over now. Did what I had to do, cause you’re so far past me now” -Cruel World | Lana Del Rey

Chapter One

Chapter Two

Chapter Three

Chapter Four - TW!

Chapter Five- TW!

Chapter Six

Chapter Seven

Chapter Eight

Chapter Nine - TW!

Chapter Ten

Chapter Eleven

Chapter Twelve

Chapter Thirteen - TW!

Chapter Fourteen

Chapter Fifteen

Chapter Sixteen

𝕥𝕣𝕒𝕚𝕟𝕚𝕟𝕘 𝕪𝕠𝕦 ❤️

Summary: Dean wants to try something new

Pairing: Dean Winchester x fem!reader

WC: 2.2K

CW: 18+ MDNI, anal (fingering, toys, penetration), unprotected pinv (wrap it up), creampie, dom!Dean, language, overstimulation, aftercare (Dean's a total gentleman), oral sex (f receiving), pet names (baby, sweetheart), size kink, praise kink (I've got a thing with that). I'm probably missing some.

A/n: I don't know how to explain myself, y'all. Probably the sluttiest thing I've ever written. Plz don't tell my mom. Also this is the first thing I've written with just Dean. I feel like I've done him dirty until now.

*(pictures from Pinterest)*

It wasn’t a HARD no for you. Dean had brought it up before and you shrugged—it wasn’t something you had thought about or really desired. Not to mention Dean was large. There was no way you could picture him fitting.

Dean thought you were perfect in every way—inside and out. He loved making you feel good. He loved your beautiful noises that you rewarded him with when he fucked you just right. If he could live between your thighs, buried inside your perfect cunt, he would.

He loved getting you to try new things. You’d be hesitant at first—your cheeks blushing when you’d get that precious doe-eyed look on your face. Dean always respected your decision—if you said no, it meant no. If you didn’t like the way something felt, he stopped immediately. You were in control, even if he was the unspoken dominant.

Lately, Dean had enjoyed bending you over and gripping your perfect ass, gently parting your cheeks to watch your cunt swallow his thick cock. He’d let his thumb drift toward your tight hole, testing the waters, gauging your comfort level.

Eventually, you let him gather some of your wetness and push one of his digits inside you while he stilled his movements. He felt your body tense up, subconsciously pulling away from him. He reached around and massage your your clit, causing your tense muscle to relax.

“You’re doin’ so good f’me baby, so proud of you.” His voice was so deep and smooth, and you melted like butter.

The praise worked—you start to rock your hips back on him. The added pressure of his finger pushes his cock against your sweet spot and you come hard. He lets you ride it out, your whole body shaking while you take what you need.

Dean was going to take his time, though. As badly as he wanted to feel your tight ass clench around his cock, he knew you were hesitant.

He needed to train you.

Over the next few weeks, he’d always try and give your asshole some loving attention when he fucked you. You were surprised how much harder you came, even if it was still a little uncomfortable. It wasn’t painful—it just felt unnatural.

Dean wasn’t crazy about toys—his ego told him that he could give you anything you needed. A chunk of cheap silicon couldn’t make you come as hard as he could. But if he wanted to properly train your tight hole, toys could certainly help.

You laughed when came home with a set of differently-sized plugs. They had a sparkly little purple jewel on the end of them.

“Is this the Dean Winchester version of jewelry?”

“Just trust me. You’ll like it. Besides, they’re way more useful than a ring or a necklace.”

His lack of awareness made you roll your eyes playfully.

He was right, though. You did seem to enjoy the plugs. After the initial burn of it sliding past your tight muscle, you immediately felt relaxed. You still weren’t totally comfortable with him fucking you with a toy inside of you. Instead, he would gently tug on it while he ate you out. The dual sensation was becoming addicting.

After two months, Dean could tell how eager you were—he felt like you were ready to take him. Naturally, he started to pull back. He would tease you by gripping your ass with both hands, but his fingers wouldn’t explore any further.

You didn’t ask why, even though you were craving it. Maybe he wasn’t in the mood. Maybe it was you, but you were desperate. So you decided to surprise him.

Sam and Dean had been gone for a few days. Dean had been texting you more than normal and you could tell he missed you. You were being intentionally vague and aloof. It was driving him crazy.

In his absence, you had been playing with your tight little hole, using your slick to lube your fingers before dipping them past your rim. You even used your favorite vibrator to get used to some length—not like it compared to Dean.

As soon as you started massaging your clit, picturing Dean’s fingers working on you, you came hard, clenching hard around your toy.

Dean really had ruined you.

The boys were driving home that day, so you showered and shaved before slipping into one of Dean’s t-shirts that came down to your mid-thigh and a pair black lacy panties (you only wore them for him)—not before inserting one of the jeweled plugs Dean had gotten you.

He would be home soon—so you laid in bed to watch TV, trying to relax your nerves. When Dean walked into your room, he found you lying on your side, one leg hiked slightly, highlighting your beautiful curves and exposing a thin line of your panties below the shirt.

You didn’t look at him at first, still playing hard to get. Dean let out a frustrated sigh that he kept caged in his chest—it sounded like a growl.

He shut the door behind him, kicking off his boots and dropping his bag, he crawled onto the bed with you, flipping you onto your back which added pressure to your plug. He gazed down at you, caged between his arms, before kissing you like he was desperate and hungry.

“I missed you, sweetheart.”

The nickname made you melt. You didn’t show it though.

“Oh yeah?” You teased.

You could feel his bulge pressing against the bare skin of your thigh. You had missed him too, and you were eager to show him his surprise.

He groaned again, he just wanted to taste and feel you. Show you how much he missed you.

You pulled your shirt off—you were done playing hard to get. His mouth watered at your perfect tits. His eyes traced down to the black panties you had on. The only thing he loved more than you wearing them was peeling them off of you.

He pressed soft kisses to your clothed pussy. He could taste your arousal through them, noticing the wet spot that was forming there. Still, he kept teasing you, licking long stripes and tasting you getting even wetter.

Dean hooked his thumbs into the hem of your underwear and started pulling them down your legs. Only when his eyes returned to your glistening folds did he notice the pretty little jewel below your pussy.

He raised his eyebrows and felt his mouth water at the sight. You blushed, hoping his expression was positive.

“Fuck, sweetheart. Is that for me?”

You nodded sheepishly.

“You think you’re ready for me?”

You nodded again, more eagerly this time.

“Y’gotta say it, sweetheart. You know the rules.”

“Yeah, I’m ready…I think. I’ve been practicing while you were gone.”

Dean moaned at the thought of you playing for yourself. You had let him watch you before, but this was different.

“You’re gonna need to tell me about that later, baby, but I want you now.”

You blushed again—you’d never had anyone who knew or loved you like Dead did.

Before he could bend you over, he dove back into your dripping cunt and slid one of his thick digits into you. The way he sucked and fucked you made you scream and come in a minute.

“Such a good girl for me,” he cooed against you, while gently lapping at your sensitive bud.

Once you started to come down, you were desperate for him to fill you up.

“Please fuck me, De—I want you so bad.”

He grinned while he wiped your wetness of his face.

“Yeah? Where do you want me, baby?”

You blushed nervously, still too nervous to ask for exactly what you wanted.

“You want me in that tight pussy? Or that pretty little mouth?”

You smiled and gently shook your head.

“You gonna let me fuck that tight little ass?”

“Please, Dean—“

“Only if you’re sure, Y/N. If you don’t like it, we stop, okay?”

He made you feel so safe—he pushed you without breaking your trust.

You leaned forward and kissed him, and you could feel him smile against your lips. He stood up and stripped while he nodded towards the bed.

“Bend over, sweetheart.”

You turned over on your knees and elbows, arching your back to give him better access.

Dean grabbed some lube out of the nightstand and set it next to you on the bed. Usually he could use your wetness to coat his finger or a toy, but accommodating him was going to be a challenge.

He slowly pulled the plug out, gently massaging it in and out around the thickest part. You moaned and writhed underneath his touch.

Setting the toy next to you on the bed, he admired at how relaxed your little hole was now. He took the bottle of lube, holding it above your ass and squeezing lightly, watching as a it dripped above your hole, causing you to flinch at the sensation.

He gently massaged it around your muscle, coating his fingers. He applied a generous amount to his cock

“You ready?”

You hummed and pushed your hips back against him, the tip of his cock nudging against your hole. You were nervous, but you trusted Dean.

His big hand pressed against your low back, causing you to deepen your arch, while his other hand guided his bulbous head into your ass.

“It’s gonna hurt a little at first, just like the plug, m’kay?”

You nodded and encouraged him on.

He slowly pressed forward, stopping after a couple of inches when he felt you grip him like a vice.

His arm reached around you and gently massaged your clit while he encouraged and praised you.

“Just relax baby. You’re doing so good. Just a few more inches.”

You weren’t sure how you fit this much of him.

His gentle massage helped your muscle release him and allow him further inside.

Eventually he was fully seated inside of you, his hips flush against your cheeks.

“God you’re so tight. So perfect for me.”

Dean rubbed your sides gently to help you adjust to the size of him. It was starting to feel better.

“I’m gonna move a little bit—that okay?”

“Mhmm, keep going.”

The weight and fill of his cock inside of you was almost overwhelming. You played with your clit again to help relax. The faster he moved, the wetter you got, and the better it felt.

“Please don’t stop, Dean.”

“Wouldn’t dream of it, sweetheart.”

You finally came—your fingers swirling your sensitive bud while Dean stuffed you from behind. He could feel your pussy clenching around nothing and it gave him an idea.

He slowly pulled out, careful not to hurt you, and gently pulled you up, guiding you towards the armchair in your room.

He sat down and pulled you backwards towards him to hover over his lap. With your back against his chest and your legs spread, he could easily work on your pussy while he fucked up into you.

Being on top added more pressure, but you were ready for him. Once you were fully seated on him. He brought two fingers to your cunt, gathering some of your wetness on them before plunging them inside of you. With your ass full of him, your pussy felt impossibly tight.

The stretch was almost overwhelming. His thumb rubbed your overstimulated clit and you started to rock your hips in his lap, slowly fucking yourself onto his cock. He wasn’t going to last much longer like this, so he picked up the pace and gently bounced you on his lap, desperate to draw another orgasm out of you.

The sounds that came out of you were unintelligible moans and whimpers and he felt you tighten up around his fingers.

“Come f’me again baby, let me feel you,” he whispered against your neck.

You squeezed him so hard he was sure you were going to cut the circulation off to his cock. You screamed so loud there was no way Sam didn’t hear you. Dean just hoped he wouldn’t come check on you.

With a few more thrusts, he was spilling into your tight hole and withdrew his fingers from your sensitive cunt. He wrapped his arms around you and stood you up, slowly pulling out of you, before gently laying you down on the bed.

Dean was the king of aftercare. He handed you your water bottle and wrapped a light blanket around you, instructing you to drink. Once he saw you were settled, he went to the bathroom and drew you a warm bath.

Finding you comfortably curled up on the bed, he felt bad scooping you up and carrying you to the bathroom.

Dean got situated in the bathtub before gesturing for you to climb in. You settled back against his strong chest and felt your body melt against him. You were sore, but in the best way possible.

“You did really good, baby,” he mumbled against your head before pressing a kiss there. “You feel okay?”

“Mmm, yes. I loved it.”

Dean couldn’t help but beam proudly. He loved seeing you coming out of your shell and try new things with him.

His mind was already swimming with ideas for things he wanted to try with you, but for now, he was totally content.

𝔽𝕚𝕣𝕤𝕥 𝕥𝕚𝕞𝕖 ❤️

He wasn’t concerned that midterms were next week, or that he had class in the morning. The only thing he was concerned about was making you feel safe and special.

Pairing: Stanford!Sam Winchester x college!reader

WC: 3.3K

CW: 18+ MDNI, virgin reader, loss of virginity, reader is female with female anatomy, description of college party & drinking, language, pinv, oral sex & fingering(f receiving), Sam being sweet and fluffy, size kink if you squint, mild angst

A/n: motherhood is wild y’all! I had this in a draft and figured I’d post it while baby wants to be awake all night 😅💕

You had planned on losing your virginity before you got to college, wanting to leave that awkward experience at home. There were a few times you felt ready, but the person didn’t make you feel safe, or your nerves got the best of you.

By the time you got to Stanford, you had some experience—you’d given a couple drunken handjobs, but you haven’t had much done to you aside from some awkward groping.

When you met Sam Winchester in one of your classes, you were immediately drawn to him. He was hard to miss at six foot four—not to mention he looked like an Abercrombie model. Sam wasn’t really your type, but he had such a pretty smile and charming personality that you would make an exception, if you were lucky enough to have a chance with him.

After you started studying together, you quickly caught feelings for him. Sam was shy and nervous—it was surprising for someone with such an imposing figure, but it only made you more drawn to him.

Your heart nearly exploded when he asked you to join him at a house party on campus. He tried to play it cool, but he was completely infatuated with you at that point. Being rejected would have broken him, but he would never pressure you if you didn’t want to.

You agreed, trying not to sound overly excited.

After spending hours getting ready, changing clothes ten times to find something you felt good in, you showed up at the party with your roommate. You both separated quickly—she was an extrovert and immediately found a large group of people to get lost in. You were only scanning the room for one person.

Finally, you found him in the kitchen, chatting quietly with a group of guys you recognized from class. When his eyes finally found you, they never left. He smiled nervously and moved towards you—offering you a beer and removing the cap for you.

You spent hours chatting in the kitchen. It was amazing how easily the conversation flowed, even without drinking excessively. You were a little buzzed after the second beer, but not drunk.

Eventually, you moved outside, after a loud group moved into the kitchen, making it hard to hear each other. You both settled on a bench next to a fireplace on the back patio.

Cozying up at his side, his warmth was so inviting. It was the first time you had felt this good next to somebody. His woodsy cologne and the faint, tangy smell of beer made your head feel thick in the best possible way.

Sam felt the same way, slowly leaning closer to you. He settled his arm around your waist, gently stroking your side with his thumb. It might have been the liquid courage, but your eyes locked onto his and you quickly leaned in, pressing a light kiss against his soft lips. It was shy and tentative, making him smile at the sweetness.

He pulled you into his lap, letting his large hands settle on your hips. He just studied you for a moment, drinking in the way the firelight illuminated your soft features.

“You’re so pretty,” he said quietly, making you blush.

“Not compared to you.”

He let out a breathy laugh before he cupped your jaw and pulled you closer, kissing you more intensely. He ran his tongue across your lower lip, coaxing you to open up to him and making your breath hitch. You fisted his flannel to ground yourself in him.

He was a better kisser than you, but you learned to mirror him quickly.

His free hand traced your spine, but his touch stayed respectful. By now, other guys would be groping your chest or guiding your hand to their dick.

Part of you wished he would—you were so turned on by him that you could feel wetness pooling in your panties. The friction made you gently rock your hips against his. His hands tightened on your hips to still your movements.

“Relax, sweetheart,” he breathed, smiling as you chased his lips again. “Let’s wait until you’re sober.”

You tried to stifle a groan, but he was right.

It was a few weeks since the party, and you were still mortified by your behavior. Sam could sense you hesitating around him. He felt bad about pulling back, but consent was a hill he would die on. You can’t consent when you’re intoxicated.

He had been thinking about you constantly. There was something so sweet and innocent about you. He wanted to love you and keep you close to him.

Sam invited you to his apartment to study for midterms. You were curled up on his bed taking notes while he sat at his desk, textbook open his lap.

“You okay?”

You hummed and looked up at him.

“Oh, yeah, just tired of looking at this crap,” you huffed, rubbing your face.

“Well, let’s take a break.”

He set his textbook on the desk and walked over to you, settling next to you on the bed. Your heart fluttered at the proximity.

Sam wrapped an arm around you and laid you against his chest.

Something about being close to Sam shattered your inhibitions. You hadn’t felt like this about any of the guys you had dated in high school or before coming to Stanford. They were so simple and predictable.

You grabbed his face, pulling him close to you and kissing him—still slightly awkward, but better than last time. You felt him smile against you as he laid you down and leaned over you. He pulled back briefly to scan your expression, as well as appreciate the sight of you. Your lips were pink and swollen from kissing him, perfectly matching the blush on your cheeks.

“So beautiful,” he cooed softly. You felt your stomach do backflips and your eyes started to water.

“So are you, Sam.”

He smiled and kissed you again, deeper this time, sliding his tongue against yours. You arched into him as he ran his hands down your side, grazing exposed skin at your waist. Sam felt his blood rushing south as he lost himself in your pretty noises.

His palm moved under your shirt, sliding against the soft skin on your belly. The contact felt amazing and overwhelming, like electricity. No one had ever made you feel loved like this.

“Sam—“

You still hadn’t told him you were a virgin. What if he didn't want you anymore? Clearly he was more experienced than you. Maybe you didn't have to tell him—maybe he wouldn’t notice.

You pushed the thoughts out of your mind, thinking maybe you wouldn’t get that far.

Sam trailed his mouth down your body, pulling your shirt up slightly and kissing your exposed skin. Your back arched even more into him and you pulled your shirt off to give him better access to you. The sight of you made his pupils dilate. The soft curve of your breasts above the lace fringe of your bra made his cock twitch in his sweatpants.

You felt nervous under his gaze, but you knew you were safe. Before he leaned down again, he pulled his shirt off, tossing it near yours on the floor. You could have looked at him all day—his body was perfect. He had a few smaller scars that you were curious about, but you were amazed at how perfectly toned he was. Your eyes followed the thin line of hair that started at his naval and trailed below his waistband.

“You’re staring,” he said, breaking the trance you were in and making you blush.

“Can you blame me?” You said nervously.

He leaned over you again and kissed you before hooking his fingers into your waistband.

“This okay?”

You nodded, feeling your heart pounding in your chest.

He started to slowly peel your leggings off, revealing a small spot of arousal on your panties.

Once your pants were discarded, his hand slid up the inside of your thigh and landed on your clothed core. His thumb gently rubbed you through the fabric and your head relaxed onto the mattress. You started to push yourself against his hand, chasing the sensation.

You whined quietly as your thighs trembled around his hand.

“You like that?” Sam was amazed at how much you responded to him, even though he hadn’t actually touched you yet.

The simple act of his thumb rubbing your clit through your panties while his fingers rested on your mound was enough for you. You came with a muffled cry while you shook beneath him.

As beautiful as you looked, he was still surprised. He raised his eyebrows and watched as you slowly came down. You finally propped yourself up on your elbows and looked at him, suddenly mortified by his expression.

“I’m sorry…”

Sam shook his head and affectionately gripped your thigh.

“Nothing to be sorry for, Y/N,” he said, “I like making you feel good.”

You noticed the bulge in his sweatpants and the size made your throat tighten. The nerves started to creep back in, the same ones that had put you in this position to begin with. He looked a lot bigger than any of the guys you had seen before, not that there were many.

He noticed your gaze and blushed, rubbing the back of his neck.

“Do you wanna keep going?”

You nodded hesitantly, smiling to seem confident.

Sam waited for you to answer him before continuing.

“Y-yeah, I want to,” you said quietly.

“We don’t have to, honey, I won’t be mad.”

You rolled your eyes playfully before repeating yourself.

He stood up from the bed, reaching into his nightstand to grab a condom. When he pulled his sweatpants down, you almost had a heart attack at the sight of him. He was long and thick, the tip of his cock was red and swollen, leaking a small bead of precome.

Sam had gotten this reaction before, but he was always gentle—making sure to get them ready before slowly pushing inside.

He kneeled between your thighs and you did your best not to let them shake. His fingers gripped your panties and you lifted your hips to help him pull them off.

His fingers dragged through your slit, coating them in your arousal, making you shudder. Your nerves were on overdrive, but you felt ready.

You trusted Sam, but now you were worried that he might not trust you if you didn’t tell him the truth.

Before you could work up the courage to tell him this was your first time, he slid one of his long fingers inside you. Your jaw went slack and you clenched around him. You weren’t ready for that kind of intrusion—the feeling was so foreign and uncomfortable. You emitted a sound, somewhere between a gasp and a groan, making Sam stop immediately.

He was amazed at how tight you were—his finger almost filled you completely—and your reaction raised alarm bells.

“You’re so tight,” he said, his voice barely above a whisper. “Does that feel okay?”

You tried to adjust to the feeling of his thick finger inside of you, but now you were so uncomfortable and nervous that you were falling apart. Turning your head to the side, facing the wall, your chest started shuddering and you felt hot tears flood your cheeks.

“Y/N? What’s wrong? Hey, look at me—“

He slowly withdrew from you and moved to your side, trying to gauge your emotion.

“Have you…done this before?” His voice was soft and filled with genuine emotion.

“No,” you quietly squeaked, still not able to face him.

His natural instinct to love and protect kicked in and he quickly grabbed a blanket to cover you in. He wrapped himself around you and pulled you close.

“Why wouldn’t you tell me?”

You took some deep, grounding breaths to try and steady yourself.

“I was embarresed— thought maybe you wouldn’t notice and I could just…get it over with.”

Sam’s heart clenched. This was supposed to be a special experience and he felt that he had nearly robbed you of that.

You were worried that you had ruined the moment— one that you were sure now that you wanted to share with Sam.

“I trust you…and I wanted it to be with you. I’m sorry I didn’t tell you.”

He propped himself up on his elbow and turned your chin to face him.

“You could have just asked me, that way I would have helped you feel ready.”

You rolled toward him and faced him.

“I still want that.”

His gaze softened even more.

“I’ll take good care of you, baby,” he murmurs before kissing you again.

He returned to the space between your thighs and lowers himself to your heat. He presses a soft kiss to your clit before looking up at you.

“Anyone ever done this before?”

You shook your head nervously.

“You’re gonna love it—let me know if you don’t, though.”

Sam draped your leg over his shoulder and rested his big hand on your thigh. He started planting soft kisses from your inner thigh toward your core. He wasn’t trying to tease you—he was just trying to get you used to the sensation.

When he finally started to drag his tongue against your folds, you whimpered and your legs trembled around his head. You tasted so sweet and tangy and it took everything in his will power not to selfishly swallow your tight cunt.

“That feels s’good Sam,” you whined quietly.

He had been holding back until that point.

Sam started quickly tonguing your entrance while his nose nudged your clit. You fisted the sheets and your hips rocked gently. Your eyes were watering but you weren’t sad, or scared—you’d never felt that good before in your life. No one had ever made you feel that special.

Your eyes snapped open when you felt him slide a finger inside of you, but it didn’t hurt like it did before. The feeling was still slightly uncomfortable, but he didn’t bury himself to the knuckle—he stopped when he felt you tense up, trying to work you open from there.

It didn’t take long for him to feel your walls start to relax as you got even wetter for him. He wasn’t in a hurry, though. He wasn’t concerned that midterms were next week, or that he had class in the morning. The only thing he was concerned about was making you feel safe and special.

Eventually he was able to add a second finger and the pressure was explosive, but not painful.

He felt your soft walls start to flutter so he gently crooked his long fingers against your g-spot, making your vision go white and your brows to knit together.

“Such a good girl,” he mumbled against you while he watched you come undone again.

Once Sam felt your muscles relax and your breathing still, he withdrew his fingers with a wet pop that made your cheeks blush.

He kneeled between your legs, gently stroking himself. You swallowed hard, trying not to focus on how nervous you still were to take him.

“You sure you want me?” His voice was deep and warm, but it was sincere.

You nodded quickly, shifting your hips and planting your feet on either side of him. He smiled gazing down at you while he rolls the condom on, lining himself up with your entrance.

He opened your legs up wider for him to settle there and dragged the head of his cock through your wet folds. Just the heavy tip against you made you nervous—there was no way he was going to fit.

It was like he could read your mind.

“Just relax—it might hurt for a minute, but I promise it’ll feel good.”

Your eyes screwed shut and your breath hitched when Sam pressed into you. He grabbed your hand that was digging into the sheet, watching your knuckles turning white.

“It’s okay, Y/N, just breathe,” he mumbled against your wrist before pressing a kiss there. You felt your muscles loosen in your back and thighs as you relaxed back into the bed. Sam laid your wrist on your belly and lowered his thumb to your bundle of nerves and gently rubbed like he did the first time.

He pushed further into you. You could almost feel him in your stomach. It was hard for him not to come with the way you were squeezing him. He just kept his eyes on you, watching you slowly relax around him as he circled your clit. He only sank halfway into you before you pressed your hand against his chest.

“It hurts,” you said quietly.

He nodded before leaning down and kissing you, trying to calm you down.

You felt him pull out, just leaving the tip inside, before slowly sinking into you, halfway again. This time it felt different—you felt butterflies in your stomach as your gummy walls stretched around him.

Sam noticed the little smile on your face and started rubbing your clit faster. He pulled out again, thrusting a little deeper this time. After a few more thrusts, he was fully seated inside you.

Once you felt his hips flush with yours, you pushed yourself up on your elbows and looked down to where you were connected. You were amazed at how good it felt despite being slightly horrified that he fit inside of you.

“You’re doing so good,” Sam said quietly, kissing you softly again and laying you back on the bed. He caged you between his arms and slowly started to fuck into you. Your eyes rolled back into your head and you struggled to breathe as he nearly forced the air out of your lungs.

Sam kept his pace slow with one of his hands braced on your hip. You felt another orgasm building in your core and he felt it, too. His eyes fell to your low belly and he could see a small bulge rising from where he was filling you. He laid his hand there and the feeling of your belly bulging sent him over the edge. His hips stuttered and he came with a stifled groan.

You watched him while he stilled his hips—you assumed he was done, and you had already come twice. He didn’t need to keep going, so you just relaxed and waited for him to pull out while you felt your building orgasm fizzle out.

After a moment, he started rutting into you again, this time slightly harder but keeping his pace slow. He was ramming against your cervix, making your eyes roll back into your head. It was almost too much for your first time, but the feeling from being so full was mind blowing.

You were mumbling dumbly, the only thing Sam could make out was his own name. Seeing you take him so well was beautiful. He hiked your leg over his shoulder, giving him better access to your g-spot.

“Fuck—Sam! Oh my god!”

He grinned watching you fall apart again. The feeling of you pulsing around him, almost sucking him in more, made him come again. He stayed buried inside you—he never wanted to pull out. You were almost perfectly moulded around him like you were built for him.

He put your leg down and started gently massaging your hips with his thumbs.

Your body was sore, but in an oddly good way.

“You okay?” Sam was worried that maybe he went too far, or he was too rough.

You smiled and nodded.

“Did I do it right?” You laughed nervously, but you were serious.

“You were perfect,” he said,” besides, it was my job to make you feel good.”

Sam finally pulled out slowly making you wince. You tried sitting up but your arms were like jelly.

“Just…stay still, honey.”

He got you cleaned up and gave you a pair of his sweatpants (that were way too long) before tucking himself around you in bed.

“We should probably finish studying, Sam,” you said with your face pressed against his bicep.

His grip around your waist tightened and he pulled you closer to him.

“Yeah—not tonight. This is about you.”