summary: when you think of dean winchester the first thing that comes to mind is the hollowness he left inside of you the moment he left. you swore you were done with him. you grew your walls brick by brick. you never had to think about what you would do when he shows back up at your door.
warnings/tags: angst, I am so sorry for the angst, set in season 3/pre dean going to hell, lil fluff, gotta let the man have some happiness, smut (oral f receiving, unprotected sex, praise)
masterlist // join the taglist
You never let yourself believe the stories about second chances. Not after Dean Winchester.
Years had passed since the night everything changed—since the vampires had come for you in the dark of this same quiet town, and a stranger with a machete and a smirk had dragged you out of hell before you even knew hell was real. He’d been reckless and cocky and so damn alive it hurt to look at him. You’d fallen hard, stupidly, completely. Let him in your home. Listened to him talk about family and hunting and the things that went bump in the night like it was just a normal day. Let him press you against the Impala under a sky full of stars and kiss you like he was trying to memorize the shape of your mouth.
Then he’d left. Hunters don’t stay. You’d known that even while you were still tasting him. Still, it had hollowed you out.
You’d tried. God, you’d tried. Dated men who were soft and safe and never carried silver in their pockets. Forced yourself to smile through dinners that felt like pale imitations. None of them ever looked at you the way Dean did—like you were the only solid thing in a world full of monsters. None of them ever made your pulse kick the same way. Eventually you stopped trying. Built a quiet life in the same town he’d saved. Pretended the supernatural had been a fever dream. Pretended the ache in your chest was just residual trauma and not something with a name and green eyes and a leather jacket.
Tonight the past walks right up to your door and knocks.
It’s late. Rain is tapping against the windows in a steady, tired rhythm. You’re in an old sweater and bare feet, hair still damp from a shower, when the knock comes—three hard raps that don’t sound like a neighbor. Your stomach drops for reasons you can’t name yet. You check the peephole out of habit more than fear.
And the world tilts.
Dean Winchester is standing on your porch like a ghost that never learned how to stay dead.
He’s thinner than you remember. Shadows sit heavy under his eyes. There’s a cut high on his cheekbone that’s already scabbing over, and his left shoulder is held carefully, like every breath costs something. The familiar leather jacket looks lived-in and worn, collar turned up against the rain. Water drips from the ends of his hair onto the porch boards. He doesn’t smile when he sees the curtain shift. Just waits, jaw tight, like he’s bracing for you to tell him to leave.
Your hand is shaking when you unlock the door and pull it open.
Cold night air rushes in. So does the smell of him—whiskey, rain, iron, and that undercurrent of something darker you never could name. For a second neither of you speaks. The years between you sit heavy and sharp.
“Dean.”
Your voice comes out quieter than you meant it to.
He huffs a soft, almost-laugh that doesn’t reach his eyes. “Yeah. Still me.” His voice is rougher than it used to be. Lower. Like he’s been screaming or not speaking at all. He shifts his weight and winces, just barely, before he can hide it. “Sorry about the hour. Didn’t know where else to go.”
You should slam the door. You should demand answers. You should tell him that the girl he left behind learned how to stop waiting. Instead you step back, heart slamming against your ribs so hard you’re sure he can hear it, and let the door swing wider.
“You’re bleeding.”
He glances down at himself like he forgot. There’s a dark stain along the side of his shirt, mostly hidden by the jacket. “It’s not that bad.”
“That’s what you said last time.” The words slip out before you can stop them—sharp with old hurt.
Dean’s mouth tightens. He looks at you properly then, really looks, and something complicated moves behind his eyes. Guilt. Hunger. Exhaustion so deep it looks like it’s carved into the bone. “I know.” He swallows. “I know I don’t get to just show up. But I’m here. And I’m… I’m not in good shape, sweetheart.”
The pet name hits like a brand. You feel it low in your stomach, unwanted and familiar.
You cross your arms over your chest, mostly to keep your hands from reaching for him. “Why are you here, Dean? After all this time. Why now?”
He opens his mouth. Closes it. Rain continues to fall behind him in soft sheets. For a moment he looks like he’s going to give you one of those charming, deflecting smiles he used to hide behind. Instead his shoulders drop a fraction, and the honesty that comes out is quieter than anything you’ve ever heard from him.
“Because everything’s running out.” He meets your eyes and doesn’t look away. “And I needed to see you one more time before it does.”
The words settle between you like a loaded gun.
Your pulse is a war drum in your throat.
You step aside anyway.
“Come in,” you say, voice steadier than you feel. “Before you bleed all over my porch.”
Dean limps past you into the warm light of your living room, bringing the rain and the past and every unfinished thing with him. The door clicks shut behind you both.
And just like that, the life you’d carefully rebuilt starts to crack open all over again.
You don’t move right away after the door shuts.
Dean stands in the middle of your living room like he doesn’t quite belong in the soft light, dripping rainwater onto the hardwood, one hand pressed low against his side. The years haven’t softened him. If anything, they’ve sharpened every edge. His eyes track you the way they used to track threats—careful, assessing—except there’s something raw underneath it now. Something that looks a lot like need.
You stay by the door a second longer than necessary, arms crossed tight over your chest, every wall you’d spent years building rising back into place.
“You don’t get to do this,” you say quietly. “You don’t get to show up bleeding and look at me like that. Not after you left.”
Dean’s mouth twists. He doesn’t argue. Just gives a short, tired nod like he expected the hit. “Yeah. I know.”
You force yourself to walk past him toward the kitchen, heart still hammering. The first-aid kit is under the sink where it’s always been. When you come back he’s lowered himself onto the edge of the couch with a muted hiss, jacket already half-shrugged off. The dark stain on his shirt is larger than it looked on the porch. You set the kit down harder than you mean to.
“Shirt off.”
He glances up, one brow lifting in that old, automatic smirk—but it fades fast when he sees your face. No games tonight. He peels the fabric up carefully, revealing a long, ugly gash along his ribs and a constellation of older bruises in various stages of healing. You kneel in front of him without thinking, the same way you used to, and the familiarity of it almost undoes you.
“Why me, Dean?” The question comes out sharper than you intend while you clean the blood away with careful, efficient strokes. Alcohol on gauze. His muscles jump under your fingers. “There are a hundred people who know how to stitch a hunter back together. Why did you come here?”
He’s quiet for so long you think he won’t answer. Then his voice drops, rough and low, like the words cost him.
“Because you were the only thing that ever felt real.”
Your hands still.
Dean stares at the floor between his boots, jaw working. Rain ticks against the windows. When he finally looks at you again, there’s no bravado left. Just honesty stripped down to the bone.
“Everything else was noise. Monsters. Motels. My brother. The job. But you…” He swallows. “You felt like something I could actually keep. Something that wasn’t going to turn into ash the second I looked away. I left because that’s what I have to do. Because hunters don’t get soft landings. But I never stopped thinking about this place. About you. And right now—” His voice fractures, just slightly. “Right now I needed something real again.”
The confession lands heavy between you. You want to be angry. You want to throw the gauze at him and tell him real things don’t vanish for years without a word. Instead your throat tightens and your hands resume their work, gentler now, almost against your will.
“Tell me what’s happening,” you whisper. “Please. You’re hurt worse than you’re letting on. You’re tired in a way I’ve never seen. Something’s wrong. I can feel it.”
Dean’s eyes flick to yours, then away. He shakes his head once, firm.
“Not yet.”
“Dean—”
“I said not yet.” The words are quiet but final. He reaches up, surprising you, and covers your wrist with his hand—calloused, warm, careful. “I’ll tell you. I swear. Just… not tonight. Let me have this for a little while. Please.”
You search his face for the usual deflection and find none. Only exhaustion and a quiet, stubborn desperation. The same stubbornness that once made him stand between you and a nest of vampires without hesitation.
You finish cleaning the wound in silence. Butterfly bandages. A neat wrap of gauze. Your fingers linger a second too long against his skin before you force yourself to pull back. He doesn’t comment. Neither do you.
The rain softens into a steady hush. The house feels smaller with him in it. You should send him to the guest room. You should put distance between the past and the present. Instead you sink down onto the couch beside him once the kit is put away, both of you still damp from rain and tension, and the fight drains out of you all at once.
Dean shifts carefully, making space. You end up half-curled against the armrest, legs drawn up, while he settles more heavily into the cushions. Neither of you speaks for a long time. The only sounds are the rain and the slow, even rhythm of his breathing as the pain medication and sheer exhaustion start to pull at him.
At some point your eyes grow heavy. At some point his shoulder becomes a solid, familiar warmth against yours. You tell yourself you’ll only rest for a minute. That you’ll get up and put proper space between you before morning.
You don’t.
Morning light cuts soft through the kitchen window when you finally wake.
Sleep takes you both like a tide—quiet, inevitable. Your head tips against the back of the couch. Dean’s larger frame eases sideways until the side of his face rests near your temple, one arm loosely curled as if even unconscious he refuses to let the only real thing slip away again.
The couch is empty. The blanket you’d half-kicked off sometime in the night is folded over the armrest with surprising care. For one disorienting second you wonder if last night was another dream you shouldn’t have let yourself have. Then the smell of coffee reaches you and the low sound of a cabinet closing tells you otherwise.
Dean is already up.
You find him in the kitchen in yesterday’s jeans and a clean black T-shirt you don’t recognize. His hair is still damp from a shower, the cut on his cheek cleaned, the careful way he moves still giving away the injury under the bandage. He’s leaning against the counter with a mug already in his hand, staring out the window like the backyard holds answers.
You don’t speak at first. Just cross the cool floor in bare feet, pull the second mug from the cabinet, and pour yourself coffee from the pot he made. The silence stretches, not quite comfortable, not quite hostile. You sit at the small table and let out a long, quiet sigh that says more than words could.
Dean’s eyes flick to you. He doesn’t smile.
“You gonna ask again?” he says, voice still rough with morning.
“Yeah.” You wrap both hands around the warm ceramic. “What’s going on, Dean?”
He stays where he is for a long moment, gaze fixed somewhere past the glass. The muscle in his jaw flexes once. When he finally answers, it’s low and careful.
“I need more time.” He looks at you then, green eyes tired but steady. “Just… give me a little more time before we have that conversation. Please.”
You study him. The way the morning light catches the shadows under his eyes. The tension he carries like armor. Something in your chest aches, but you nod once.
“Okay.”
Relief softens his shoulders for half a second before he hides it. He comes to the table and sits across from you, both of you cradling coffee like it’s the only solid thing in the room.
You break the quiet first. “How’s Sam?”
Dean’s mouth quirks, almost fond. “Same as always. Researching himself into a headache. Eating too much pizza. Worrying.” He takes a sip. “He’s good. Stubborn as hell. We’re… managing.”
You nod, accepting the surface answer for what it is. “And life? Still the same endless bullshit?”
“Pretty much.” He shrugs, and the motion is carefully controlled so it doesn’t pull at his ribs. “Monsters. Driving. Trying not to get dead. The usual.” His eyes stay on his mug. “Nothing worth writing home about.”
You let the half-truths settle. Then he looks up, really looks at you, and the question comes quieter.
“What about you? What’d you do with all the years I wasn’t around?”
You breathe in the steam from your coffee and tell him the truth without embellishments. The job you settled into that keeps the lights on and asks nothing of you after five. The small circle of friends who still don’t know why you check the locks twice every night. The way the town stayed mostly quiet after the vampires, everyone pretending that it was just some freak accident that killed all those people. You don’t dress it up. You don’t make it sound braver or lonelier than it was. Dean listens without interrupting, thumb moving slowly along the rim of his mug, and when you finish he just nods once, like he’s filing every detail away.
The quiet returns, softer this time.
You watch him across the table—the way the ordinary morning light makes him look almost reachable—and something restless and gentle rises in your chest.
“Do you want to do something normal today?” you ask. “Something that doesn’t involve whatever’s really going on with you?”
Dean’s brows lift. A real flicker of surprise crosses his face, followed by something that might be hunger for exactly that. He leans back a little, considering you.
“Yeah,” he says after a beat. “I do.”
You think for a moment, then offer it simply. “There’s a botanical garden on the edge of town. It’s quiet this time of year. Lots of green. Nowhere near anything that goes bump. We could just… walk. Breathe. Pretend the world is only flowers for a few hours.”
Dean studies you for a long second. Then the corner of his mouth curves—small, genuine, the first real smile you’ve seen since he arrived.
“Botanical garden,” he repeats, like he’s tasting the words. “Alright. Let’s go be normal.”
He finishes his coffee in one last swallow and stands, already reaching for the jacket draped over the chair. The movement is still careful, still edged with pain he refuses to name, but there’s a lightness in it that wasn’t there last night.
The botanical garden sits on the edge of town like a secret the world forgot to ruin.
You rise too, heart doing that complicated, cautious thing it hasn’t done in years.
Wide gravel paths wind between tall stands of ferns and flowering trees, the air thick with the green smell of things still growing. It’s quiet this early—only a few distant voices, the soft trickle of a hidden fountain, the occasional rustle of leaves. You walk side by side at first, careful space between your shoulders, until Dean’s fingers brush yours once, then again, and finally stay.
His hand is warm and calloused when it closes around yours. He doesn’t look at you when he does it, just keeps his eyes on the path ahead like the contact is the most natural thing in the world and the most fragile. You let him. Your fingers settle between his without comment, and something in your chest eases even as it aches.
“This is weirdly peaceful,” Dean murmurs after a while. His voice is low, almost careful not to disturb the quiet. “Feels like the kind of place that shouldn’t let people like me in.”
You glance sideways at him. “People like you?”
“People who track blood across the states as a living.” The corner of his mouth lifts, but it doesn’t quite become a smile. “Pretty sure I’m tracking mud on sacred ground right now.”
“You’re allowed to walk somewhere beautiful, Dean.”
He doesn’t answer right away. His thumb moves once across your knuckles, absent and gentle. “Not sure the universe agrees with you on that.”
You open your mouth to argue, but a flash of color interrupts. A monarch butterfly drifts down from a nearby bush and lands squarely on the back of Dean’s free hand, right over a faded scar. He freezes mid-step like someone just pulled a gun.
You stop too, watching the tiny wings open and close against his skin.
“Don’t move,” you whisper, fighting a sudden smile.
“Wasn’t planning on it,” he answers under his breath, staring at the butterfly like it might explode. “What the hell does it want?”
“Do you have pee on your hand?"
"Do I have— What?!"
"Pee. Butterflies are attracted to the smell. Thats why they always land on kids."
Dean snorts softly. “I wish I knew why you knew that.” The butterfly stays, unbothered, and for a few long seconds the two of you just stand there in the middle of the path while something soft and living chooses him without fear. When it finally lifts away and disappears into the greenery, Dean watches it go with an expression you can’t quite name.
“Guess even the bugs know I’m on borrowed time,” he says quietly, almost to himself.
The words land heavier than the joke he tried to wrap them in. You squeeze his hand once and keep walking, letting the silence stretch until it softens again.
Later, when the sun sits higher and the paths begin to warm, you tug him toward the small stand near the exit that sells ice cream out of an old white cart. Dean raises an eyebrow at the chalkboard menu like it’s written in another language.
“You dragged me all the way out here for flowers and now ice cream?”
“Yes.” You order two cones without waiting for further protest—his the most ridiculous chocolate-and-caramel combination they have, yours something simpler. He takes his with a long-suffering sigh that doesn’t hide the way his eyes light up the second the first cold bite hits his tongue.
You find a shaded bench beneath a flowering tree and sit. For a little while the only sounds are the distant fountain and the soft crunch of cones. Dean leans back, one ankle crossed over the opposite knee, and looks almost young again in the dappled light.
“This is dangerously close to a date,” he says after a minute, voice dry.
“Is that a problem?”
He considers the half-eaten cone in his hand, then you. “No. Just… unexpected.” A beat passes. “Most of my days don’t end with ice cream and butterflies.”
“Maybe they should more often."
Dean’s gaze drops to the gravel at your feet. When he speaks again the teasing is gone, replaced by something quieter and more honest.
“Maybe. But days like this don’t usually stick around for people like me. They’re just… borrowed. Same as everything else.”
You feel the truth of it settle between you even as the sweetness of the ice cream lingers on your tongue. Still, the weight in your chest is lighter than it was this morning. The ordinary rhythm of walking beside him, of watching a butterfly choose his scarred hand, of listening to him complain about melting caramel has loosened something you didn’t realize was still clenched.
You lean your shoulder lightly against his. He doesn’t pull away.
“Then we should make the most of the ones we get,” you say.
The next few days settle into something that almost feels like a life.
Dean looks at you for a long moment, eyes searching, something almost grateful flickering behind the usual armor. He nods once, small and sincere, and takes another bite of ice cream like he’s trying to memorize the taste.
You cook simple dinners together. Dean washes the dishes without being asked, sleeves pushed up, quiet and focused like the ordinary task is a kind of prayer. You take long drives with the windows down and the radio low, his hand resting on your thigh like it belongs there. One afternoon he fixes the loose hinge on your back door just because it bothers him. Another night you sit on the porch steps and watch the sky go dark while he tells you an edited hunting story that makes you laugh even though you both know he’s leaving things out.
It’s ordinary. It’s domestic. It’s the softest either of you has felt in years.
On the third morning he leans against the kitchen counter, coffee in hand, and studies you over the rim of the mug.
“Don’t you have a job you’re supposed to be at?”
You shrug, pulling your sweater tighter around yourself. “I called out. Told them I needed a few personal days.” Your eyes meet his. “You’re more important right now.”
Something complicated moves across his face—gratitude, guilt, hunger. He doesn’t argue. Just nods once and looks away like the honesty is too bright to hold for long.
Sam keeps calling.
The first time the phone buzzes on the counter Dean glances at the screen, jaw tightening, and declines it without a word. The second time he does the same, but his shoulders stay tense for an hour afterward. By the fourth call you stop asking. You just watch the way his thumb hovers over the screen before he silences it again, like every ignored ring costs him something.
On the fifth night the phone starts up while the two of you are on the couch, some old movie flickering quietly on the television. Dean stares at Sam’s name for a long moment. Then, finally, he answers and walks into the kitchen, voice already clipped.
You don’t mean to listen. The walls are thin.
“—I said I’m fine, Sammy.”
A pause. Dean’s voice drops, sharp with something that isn’t quite anger.
“No. I’m not coming back yet. I need a few more days.”
Another pause, longer. You hear him exhale hard.
“Because I do, that’s why. Just—stop. I don’t want to talk about the research right now. I don’t want to talk about any of it.”
His tone turns quieter, almost tired.
“I’ll call you when I’m ready. Yeah. Love you too. Bye.”
The call ends. Silence stretches from the kitchen.
He doesn't come back to the couch.
When Dean appears in the doorway of your bedroom later, the only light comes from the hallway behind him. You’re already in bed, sitting up against the headboard, waiting. He looks exhausted in a way that has nothing to do with the healing cut on his ribs. Without a word he crosses the room, toeing off his boots, and climbs in beside you like he’s been doing it for years instead of days.
The mattress dips under his weight. He settles on his side, facing you, close enough that you can feel the heat of him through the sheets.
You keep your voice soft. “What was that about? With Sam earlier."
Dean’s eyes search yours in the dim light. For a second it looks like he might actually answer. Then something closes behind his gaze—old armor sliding back into place—and instead of speaking he leans in and kisses you.
It’s not careful.
It’s deep and hungry and edged with everything he won’t say. One of his hands comes up to cradle the side of your face, thumb brushing your cheekbone, while the other slides around your waist and pulls you closer until there’s no space left between you. His mouth moves against yours like he’s trying to pour the truth into the kiss instead of words—apology and desperation and a fierce, quiet need to stay right here for as long as the universe will allow.
You make a soft sound against his lips and kiss him back just as hard, fingers curling into the front of his shirt. Somewhere far away a car passes on the wet street. None of it matters.
When Dean finally draws back, just enough to breathe, his forehead rests against yours. His voice is rough, almost wrecked.
“Not tonight,” he whispers. “Just… not tonight.”
You don’t push. You simply stay there in the dark with him, hearts still racing, the unanswered question hanging heavy between every shared breath.
You don’t let him pull away for long.
The second his forehead rests against yours and the words “not tonight” leave his mouth, you chase him—tilting up, catching his bottom lip between yours, deepening the kiss until it’s wet and open and hungry. Your fingers slide into his hair, holding him there, and you feel the exact moment his careful restraint cracks. A low sound rumbles in his chest. His hand on your waist tightens.
When you finally break for air, Dean’s breathing is uneven. His eyes are dark in the low light, searching your face like he’s looking for any sign he should stop.
“Tell me I can touch you,” he says, voice rough, almost rough enough to scrape. “I need to hear you say it.”
“Yes.” The answer leaves you without hesitation. “Please. Touch me.”
Something like relief and hunger flashes across his face at the same time. He leans in again, but slower now—kissing you deep and thorough while his hand finally slips under the hem of your shirt. Calloused fingers skim the soft skin of your stomach, then higher, mapping you like he’s afraid the map might disappear. He eases the fabric up and off only after another quiet check of your eyes, and then his mouth is on your throat, your collarbone, the upper slope of your breast.
He’s careful. Almost reverent. Every kiss is deliberate, lingering, as if he’s trying to memorize the exact taste and temperature of your skin. He mouths along the underside of one breast, then the other, tongue flicking over a nipple until it’s tight and aching before he closes his lips around it and sucks slow and deep. Your back arches. A soft, broken sound escapes you. Dean makes a low answering noise against your skin and does it again, like he’s cataloguing every reaction.
“Fuck, look at you,” he murmurs, voice thick. He trails open-mouthed kisses down the center of your stomach, pausing to breathe against the soft skin just above the waistband of your sleep shorts. “Been thinking about this. About how you’d feel under my hands again. How you’d sound.” His fingers hook into the fabric. “Can I take these off?”
You lift your hips in answer. He peels the shorts and underwear down together, slow enough that the cool air kisses every newly exposed inch. Then he’s settling between your thighs like he belongs there—broad shoulders spreading you open, hands sliding under your legs to hold you steady. For a moment he just looks, eyes heavy-lidded, thumb stroking absently along your inner thigh.
“Pretty like this,” he says quietly, almost to himself. “All soft and wet for me already.”
He leans in and presses a kiss to the inside of one thigh, then the other, working higher with maddening patience. When his mouth finally reaches you, it’s with a long, deliberate drag of his tongue through your folds—slow enough to make your hips twitch. He groans low against you, the vibration sinking deep.
“Christ. Taste even better than I remembered.”
He doesn’t rush. He eats you like he’s got all the time in the world and none of it at once—flat strokes of his tongue alternating with focused flicks over your clit, lips sealing around it to suck in soft, filthy pulls that make your thighs tremble around his head. One hand stays firm on your hip, holding you in place when you try to rock up against his mouth. The other slides up your body to cup your breast, thumb brushing over the nipple he already made sensitive.
Every so often he pulls back just enough to speak against your soaked skin, voice wrecked and honest.
“That’s it… let me hear you.”
“Gonna take my time. Want to remember exactly how you fall apart.”
“So fucking sweet. Could stay right here and drown in you.”
You fist the sheets, then his hair, breathing his name like a plea. Dean only settles deeper, tongue working you open with focused, filthy precision, like he’s trying to brand the memory of your taste into himself before the night is over. The careful reverence never leaves his hands, but the way he licks into you is pure hunger—wet and devoted and just short of desperate.
“Dean—please. I need you.”
The words leave you wrecked and honest, fingers still tangled in his hair. He lifts his head immediately, mouth shiny, eyes dark and searching. For a second he just looks at you like he’s committing the sight to memory. Then he’s moving—crawling up your body with deliberate care, dragging open-mouthed kisses along your stomach, between your breasts, over the rapid pulse in your throat until he’s braced above you— tugging his pants down and kicking them somewhere behind him.
He settles between your legs, the hard, hot length of him resting against your soaked folds. One forearm plants beside your head. The other hand cups your face, thumb brushing your cheekbone. He kisses you deep and slow, letting you taste yourself on his tongue, and when he pulls back his voice is rough.
“You sure?” His hips stay carefully still even though you can feel how much he wants to push forward. “I need you to be sure. Once I’m inside you I’m not gonna want to stop.”
“I’m sure.” You slide your hands down his back, under the hem of his shirt, feeling warm skin and the faint ridges of old scars. “I want you. All of you.”
Something in his expression fractures—relief and hunger and a quieter, heavier emotion he doesn’t name. He reaches down and the blunt head of his cock is nudging through your wetness. He pushes in slow, inch by careful inch, watching your face the entire time. The stretch is perfect, thick and overwhelming in the best way. A low, punched-out sound leaves his chest when he finally bottoms out.
“Fuck… there you are.” His forehead drops to yours. “Missed this. Missed how perfect you take me.”
He starts moving in deep, rolling thrusts—unhurried, deliberate, like he’s trying to feel every ridge and flutter of you around him. One of his hands slides between your bodies, fingers finding your clit with practiced pressure, rubbing tight circles in time with his hips. The dual sensation builds fast. He keeps his eyes on yours, jaw tight with restraint, dirty praise falling from his mouth in a low, continuous stream.
“That’s it… feel how deep I am? Gonna make you come on my cock first. Want to feel you squeeze me when you fall apart. You’re so fucking wet for me—listen to that. Christ.”
He adjusts the angle, hitting a spot that makes your back arch and a broken moan spill out of you. His fingers on your clit never falter. The careful reverence never leaves his touch even as the filth in his voice thickens. You come first with his name on your lips, clenching hard around him, thighs shaking. Dean groans like the feeling wrecks him, hips stuttering, but he works you through every pulse until you’re trembling and oversensitive.
Only then does he let himself follow—burying his face against your neck, thrusts turning deeper and less controlled, a raw, broken sound torn from his throat as he spills inside you. He stays there afterward, still buried deep, breathing hard against your skin, one hand stroking absently up and down your side like he can’t quite stop touching you.
Minutes pass before he eases out. He presses a soft kiss to your mouth, then another to your temple, and disappears briefly into the bathroom. When he returns it’s with a warm, damp cloth. He cleans you with the same quiet care he used earlier—gentle strokes between your legs, wiping away the mess he left, eyes flicking up to check your face the whole time. Once he’s done he tosses the cloth aside and climbs back into bed.
You don’t wait for an invitation. You settle against his chest, cheek over his heartbeat, one leg draped over his. His arm comes around you immediately, heavy and secure. Fingers trace idle patterns along your bare shoulder.
Neither of you speaks for a long time. The house is still. His heart beats steady under your ear—alive, present, temporary.
You close your eyes and listen to it anyway.
Your fingers move without real thought—slow, absent patterns over the warm skin above his heart, tracing the outline of his tattoo, the dip of his collarbone, the soft trail of hair leading down his stomach. Dean is quiet beneath you. One arm remains heavy around your back, thumb stroking idle arcs along your shoulder blade. The house feels suspended, like the night itself is holding its breath.
Then his voice comes, low and rough, almost conversational if not for the weight under every word.
“If you knew that I was dying… would it change anything?”
Your fingers still.
The question settles into the dark like a stone dropped into deep water. For a second you can’t answer. Your heart twists hard enough that it hurts to breathe. Somewhere underneath the shock is a quieter, older recognition—you had felt it in the careful way he touched you, in the way he looked at ordinary things like ice cream and butterflies and the morning light in your kitchen. You had known something was coming. You just hadn’t wanted to give it a name.
You don’t pull away.
Instead you press closer, cheek flat over the steady (temporary) beat of his heart, arm sliding tighter around his waist like you can keep him here by force of will alone. Your voice, when it finally comes, is soft but certain.
“No.” You turn your face just enough to press a quiet kiss against his skin. “It wouldn’t change anything.”
Dean’s arm tightens around you. He doesn’t speak again. He only holds you like a man trying to memorize the exact weight and shape of someone he already knows he has to leave. You stay like that—tracing slower patterns now, listening to his heartbeat, refusing to let the darkness between the words grow any larger—until sleep finally pulls you both under.
Morning arrives thin and gray.
✦ . ⁺ . ✦ . ⁺ . ✦
You wake to cold sheets and the absence of his body. The pillow still smells like him. The space where he slept is empty, the blanket folded back with the same careful neatness he used the first morning. No note. No jacket left behind. Just the quiet click of the front door that you must have slept through, and the hollow knowledge that he is already gone.
You sit up slowly, the ache in your chest sharp and immediate. The house feels larger without him in it. Emptier.
You don't know if you'll ever get a third chance at this. But you'll hope and pray that the universe brings Dean back to you once again.
Summary: You’re Soldier Boy’s dealer, nothing more. That was the deal, until you got desperate for money and he offered to pay extra for something else. One rough night on your couch later, you panicked and ghosted him for a full week. He didn’t take it well.
❤︎ Warnings: MDNI, 18+, NSFW, substance abuse, unprotected sex, age gap, finger sucking, power imbalance, slight choking, drug use
wc: 3.5k - part 1
You’d been ghosting Ben for almost a full week.
Every time his name lit up your phone you’d stare at it until the screen went dark, then typed out some half-assed excuse, anything to keep him at arm’s length after what happened on your couch. You told yourself it was just business, that you needed space, that you weren’t supposed to feel anything about the way he’d fucked you like he meant it and then left five hundred dollars on the cushion like it was nothing.
You were half-sprawled on the couch, legs kicked up, mindlessly scrolling when your phone started vibrating hard. You didn’t even have to look. You already knew.
He was getting impatient. You could feel it. The crash was coming, and when Ben needed a fix he didn’t do subtle. If you kept ignoring him he was going to show up at your door again, and this time he wouldn’t be half as polite.
You sat up with a heavy sigh, thumbed the answer button, and pressed the phone to your ear.
“Hello?”
There was a long pause, then the sound of him exhaling like he’d been holding his breath for days.
“The fuck you been?” His voice was rough. In the background you could hear a girl’s muffled laugh, high and annoying.
“Sorry,” you said, trying to keep your tone flat. “I have other customers. Sometimes I have to prioritize them.”
Ben let out a short, humorless laugh that didn’t sound amused at all.
“Really? Do I have to fuck you again just to get some?”
Your eyebrows shot up. The bluntness of it hit harder than it should have, especially with the memory of last time still sitting warm under your skin.
“No,” you answered after a beat, voice quieter than you meant it to be. “You don’t. I can meet you tonight.”
“Yeah, baby. I’ll get ‘em soon. Don’t you worry that pretty head.”
The girl in the background said something, clearly annoyed that he was still on the phone with you. Ben didn’t bother answering her.
You closed your eyes, let out a long breath, and hung up before you could say anything else.
Your body collapsed back onto the couch the second the call ended, a heavy groan slipping out of you as you stared up at the ceiling.
Eventually you forced yourself upright, dragging your fingers through your messy hair and deciding, against every instinct that told you to stay small and invisible, that you were going to get ready properly.
You washed your hair for the first time in days, standing under the hot water until the steam filled the tiny bathroom, then you took your time with makeup.
You told yourself it had nothing to do with him. You weren’t dressing up for Soldier Boy. You just wanted to feel pretty for once, to look like someone who had her shit together instead of a broke dealer who’d let a supe fuck her on her own couch and then ghost him for a week out of pure panic.
By the time you slipped on your sneakers and checked yourself in the mirror one last time, the denial was starting to feel thin. You sighed, grabbed your phone, and typed out a short message telling him you were on your way.
Then you carefully slid the last of the drugs into the bottom of your backpack, zipped it shut, and stepped out into the night before you could change your mind.
By the time you finally made it to the alleyway the night air felt heavier than usual.
Ben’s black car was already parked halfway down, engine idling low, one arm hanging out the open window. He had a thick cigar clenched between his teeth, the tip glowing orange every time he took a slow pull.
“Took long enough,” he said around the cigar. He flicked the half-smoked thing out the window without looking where it landed.
You stopped a few feet from the driver’s side door, backpack already sliding off one shoulder. “Sorry. How much money do you have?”
Ben raised one thick eyebrow. He didn’t answer right away. Instead he just held up a tight band of hundreds between two fingers, waving it lazily like the amount was irrelevant.
“None of your goddamn business,” he muttered.
You rolled your eyes but didn’t push it. Unzipping the backpack, you pulled out the carefully wrapped package and held it out. Ben snatched it from your hand harder than necessary.
He didn’t even bother checking the contents this time. He just tossed three hundred-dollar bills at your chest like they were nothing, the money fluttering against your hoodie before you caught it.
“It’s one-fifty,” you said automatically, frowning down at the extra cash.
He ignored you completely, already stuffing the package into the glove box. Then he turned his head, really looking at you for the first time since you’d walked up, and the irritation in his face shifted into something heavier.
“You needa stop that avoiding me shit,” he said, “I don’t like being left hanging. Especially not after I had my dick in you.”
The words landed like a slap. You opened your mouth to snap back, but before you could get anything out he leaned farther out the window, reaching up with surprising speed. His big hand caught the front of your hoodie and yanked you closer until you were almost bent over the open window, face inches from his. The smell of cigar smoke and whatever cologne he wore hit you all at once.
“I mean it,” he growled, eyes locked on yours. “You ghost me again and I’m showing up at your place whether your mom’s home or not. We clear?”
Your pulse jumped. You managed a tight nod, the extra money still crumpled in your fist. Ben held your stare for another long second, like he was deciding whether to pull you the rest of the way into the car or just leave you standing there. Then, almost reluctantly, he let go of your hoodie and sat back.
“Get in,” he said suddenly, jerking his chin toward the passenger seat. “I’m not done talking to you.”
You hesitated, heart hammering, but the way he was looking at you left very little room for argument. With a quiet breath you walked around the front of the car, opened the passenger door, and slid in beside him. The second the door shut, Ben locked it with a soft click and pulled away from the curb, the alley disappearing behind you in the rearview mirror.
You sat stiffly in the passenger seat, the crumpled three hundred dollars still clenched in your fist, backpack resting between your feet.
Finally he spoke.
“You look different.”
You glanced over and caught him side-eyeing the makeup you’d carefully put on earlier, the clean hair, the way you’d actually tried to look put-together for once.
“I just felt like it,” you muttered.
Ben let out a short, skeptical sound through his nose. “Bullshit. You put that shit on your face because you knew you were coming to see me.” He didn’t sound smug about it. He sounded almost irritated that you’d done it at all. “Don’t start acting like you’re trying to impress me. That ain’t what this is.”
You opened your mouth to argue, but he cut you off before the words could form.
“And don’t look at me like that either.” His hand flexed on the gearshift. “I already told you I’m not paying for pussy every time. That was a one-time deal. You needed the money, I needed a release. We both got what we wanted.”
The car turned down a quieter street. Ben’s jaw worked for a second like he was chewing on something he didn’t want to say out loud. When he spoke again the edge in his voice had softened just slightly, almost against his will.
“You okay after last time?”
The question landed heavier than anything else he’d said. You stared at the side of his face, caught off guard by the unexpected check-in. He still wouldn’t look at you fully, but the fact that he’d asked at all said more than he probably wanted it to.
You swallowed. “Yeah. I’m fine.”
Ben gave a short nod, like that settled it, but his grip on the wheel tightened. A few blocks later he pulled into the empty parking lot of a closed-down warehouse, the kind of place no one bothered to check after midnight.
He killed the engine, leaving the two of you sitting in sudden quiet with only the faint tick of the cooling car and the distant sound of traffic.
“You really thought you could just disappear on me?” he asked. There was no real anger in it this time.
“I don’t do that shit, doll. People don’t get to walk away from me when they feel like it. Especially not after I had you shaking under me on that shitty couch of yours.”
“I wasn’t disappearing,” you said carefully. “I just... needed space.”
Ben let out a short, humorless breath through his nose and shook his head. “Space. Right.” He reached up and rubbed the back of his neck.
“Look,” he said, leaning an arm against the steering wheel. “I ain’t asking you to be my fuckin’ girlfriend. I’m not that guy. We can keep it simple. Or...” He paused, eyes flicking down to your mouth for half a second before coming back up. “We can keep doing what we did last time when the mood hits. You just don’t get to ghost me again. Deal?”
Outside, a light rain started to fall, soft and steady against the windshield.
Finally you nodded, quiet but clear.
“Deal.”
Without another word he reached over, grabbed you by the front of your hoodie, and hauled you across the center console like you weighed nothing. Your knees knocked against the gearshift as he pulled you into his lap, straddling him in the driver’s seat, the leather creaking under the sudden weight.
His tongue pushed past your lips immediately, tasting like smoke and whatever he’d been drinking earlier, one big hand already sliding under your hoodie to palm your breast through your bra. The other hand gripped your ass hard enough to bruise, forcing you down against the growing bulge in his jeans.
“Fuck, you’ve been thinking about this all week, haven’t you?” he growled when he broke the kiss, voice low and rough right against your ear. “Acting all distant, pretending you didn’t want my cock again. Look at you now, already grinding on me like a desperate little slut.”
You tried to say something, but the words turned into a shaky breath when his hand left your breast and shoved two thick fingers against your mouth.
“Open,” he ordered.
You did. He pushed them in deep, pressing down on your tongue, the taste of salt and skin flooding your mouth. Ben watched with dark, focused eyes as you sucked, his hips rolling up against you in slow, deliberate thrusts that made the car rock slightly.
“That’s it, good girl. Suck ‘em like you mean it. Get ‘em nice and wet for that tight little cunt.” His voice was pure degradation, but the way his other hand stroked up your back, almost soothing, kept the roughness from tipping into pure meanness. “You look so fucking pretty with my fingers in your mouth. Better than that cheap blonde I had the other night. She didn’t even try.”
He pulled his fingers free with a wet sound, then shoved his hand straight down the front of your leggings without warning. Two slick fingers found your clit immediately, rubbing in tight circles before sliding lower and pushing inside you in one firm stroke. You gasped, forehead dropping against his shoulder as he curled them, stretching you open while his thumb kept working your clit.
“Fuck, still so tight,” he groaned, voice going rougher. “Didn’t even last a week and you’re clamping down on my fingers like you’ve been starving for it. That’s what happens when you ghost me, doll. You get yourself all needy and desperate.”
He fucked you with his fingers hard and deep, the wet sounds of it filling the quiet car, his free hand still gripping your ass to keep you grinding down on his lap. n.
“I’m gonna make sure you remember who your cunt belongs to when you try to ignore my calls next time.”
When he finally pulled his fingers out you were shaking, soaked, and already close. Ben didn’t give you time to recover. He shoved his jeans down just enough to free his cock, thick and hard and already leaking, then yanked your leggings and underwear down your thighs in one rough motion. He lined himself up, the blunt head pressing against your entrance, and looked up at you with those sharp green eyes.
“Ride it,” he ordered, voice low. “Show me how much you missed this.”
You sank down slowly, the stretch burning in the best way as he filled you inch by inch. Ben’s head tipped back against the seat, a deep, guttural groan leaving his chest. His hands clamped onto your hips hard enough to leave marks, guiding you until you were fully seated, stuffed full and trembling.
“Fuck, there she is,” he muttered, almost reverent for a second before the usual crude edge returned.
He let you set the pace at first, slow, deep rolls of your hips, while his hands roamed, one sliding up to wrap lightly around your throat, the other still gripping your ass. Every time you clenched around him he groaned praise and filth in the same breath.
“Gonna fill you up so deep you feel it tomorrow when you’re trying to act like you don’t want this.”
The car rocked harder as he started thrusting up to meet you, rough and relentless, the sound of skin on skin mixing with the rain outside. He kept one hand on your throat, not choking, just holding, while the other reached up and pushed two fingers back into your mouth for you to suck again, eyes locked on yours the whole time.
“That’s it, suck while you ride. Show me how much you love being used.”
“Tell me how it feels,” he ordered, voice low and demanding. “Tell me how much you missed having me stretch this tight cunt open.”
You could barely form the words between gasps, but the second you managed a shaky “So good, missed it—” he groaned like the admission alone was enough to push him closer to the edge.
“That’s right. Missed my cock. Missed getting fucked stupid in the middle of nowhere.” He thrust up harder, the force of it making the whole car rock. One hand slid between your bodies, thick fingers finding your clit and rubbing tight, relentless circles.
The dual sensation, his cock pounding deep and his fingers working your clit, pushed you right to the edge. Your thighs started to shake, walls fluttering around him, and Ben felt it immediately. His pace turned almost brutal, chasing your orgasm like he needed it more than his own.
“Come for me,” he snarled against your mouth, voice dropping into pure command. “Come on my cock right now. Milk me. Show me who this cunt belongs to.”
The orgasm hit you hard, ripping through your body in sharp, overwhelming waves. You cried out against his lips, clenching down around him so tightly he cursed loudly, hips snapping up as he fucked you through it. The second your walls started pulsing he followed, burying himself as deep as he could and coming with a guttural groan, thick and hot inside you. His hands gripped your hips hard enough to bruise, holding you down while he spilled every drop, forehead pressed to your shoulder as he rode it out.
For a long moment the only sound in the car was the rain and both of you breathing hard. Ben’s grip slowly loosened, one hand sliding up your back in a surprisingly gentle stroke before he seemed to catch himself and stop. He stayed buried inside you for a few extra seconds, like he wasn’t quite ready to pull out, then finally lifted his head.
“Fuck…” he muttered, voice still rough. He looked at you, flushed, messy, still straddling him.
He reached up, thumb brushing roughly across your bottom lip like he couldn’t help himself, then smirked.
“Next time you try ghosting me, remember how full of my cum you are right now.”
You didn’t ghost him after that night.
At first it stayed exactly what he’d offered. He’d text at odd hours, “Got product? Come through.” and you’d meet him in alleys or empty parking lots or, more than once, the backseat of that same black car. Sometimes it was quick and rough, him bending you over the hood or pinning you against a brick wall with a hand over your mouth so no one would hear. Other times it stretched longer, the two of you fogging up the windows while he talked filthy praise and degradation into your ear until you came so hard your legs shook.
But somewhere along the way the “on and off” started changing shape.
He’d show up at your place with takeout after a deal, complaining the whole time about how your apartment was a dump while still sitting on your couch like he belonged there. He’d text you random shit in the middle of the day. “This new dealer’s product is dogshit compared to yours,” and then act annoyed when you actually answered.
Once, after a particularly rough session that left bruises on your hips in the shape of his fingers, he stayed the night. You woke up to find him already awake, sitting on the edge of the bed smoking a cigarette out the open window, looking at you like he was trying to figure out how the hell he’d ended up still there.
He never said anything soft. Not really. But the soft parts started leaking through in other ways.
He’d overpay for the product more often than not and then act like it was an accident. He’d get weirdly quiet if you mentioned other customers. One night, after he’d fucked you slow and deep on your bed instead of the usual hard and fast, he stayed buried inside you for a long time afterward, forehead pressed to your shoulder, breathing like he was trying to memorize the way you felt around him. When you asked if he was okay he just muttered, “Shut up,” and kissed the side of your neck harder than necessary.
Weeks turned into a couple of months. The casual arrangement started feeling less casual every time he showed up.
It happened on a Thursday night, of all things.
You were half-asleep on the couch when the heavy knock came. You already knew who it was. Ben stepped inside the second you opened the door, smelling like cigars and night air, a paper bag of Chinese food in one hand.
He set the food down, kicked the door shut behind him, and then just stood there. Looking at you.
“I don’t do this shit,” he said, like the words themselves tasted bad. “I don’t ask people out. I don’t do dates. I don’t do... whatever the fuck this is turning into.” He gestured between the two of you, frustrated. “But I’m tired of pretending I only show up when I want my dick wet or a bag of pills. So.” He exhaled hard through his nose. “You free Friday night or not?”
You stared at him.
Ben’s jaw tightened. “Don’t make me say it twice, doll. I’m asking you out. Properly. Dinner. Whatever. And if you say no I’m still fucking you on that couch later, just so we’re clear.”
You stared at him for a long second, the paper bag of Chinese food still sitting forgotten on the counter, the smell of sesame chicken mixing with the faint cigar scent that always clung to him.
Ben stood there with his arms crossed, jaw tight, looking like he’d rather take a bullet than repeat the question.
A slow smile tugged at the corner of your mouth before you could stop it.
“Yes,” you said, voice quiet but clear. “I’m free Friday.”
He tried to play it off immediately, of course, rolling his eyes and muttering “About fucking time” under his breath, but the relief was still visible around the edges of his expression. He stepped closer, one big hand reaching out to grab the front of your shirt and tug you in until you were pressed against his chest.
“Good,” he said, low and rough against the top of your head.
do u think dean winchester would make homemade porn for some extra money?
I am SO sorry it has taken me a month (???) to respond to this because you had a stroke of genius.
And I don't think, I know. It's not like he has a professional job he has to worry about losing, or a family that would disown him. All in all, Dean Winchester is a man with very little to lose.
The thought of him leaning against some shabby motel headboard while he smirks at the camera is too much to take. He knows he looks absolutely fucking mouthwatering on film. Impossibly tanner and somehow more rugged. And his cock... huge and leaking and just as pretty as the rest of him.
Maybe he'd even find a girl who doesn't mind being on camera, his hand wrapped around a dinky little camera he can focus on all the places you're giving to him. A shot of his hand around your neck, gripping your tit, and the way his cock obscenely parts your folds.
And in the background you can always hear him babbling, absolute filth pouring out of his mouth in a volume much too large for him to actually be in control.
Summary: You travel with the Winchester brothers and are the third body to their infamy. But it's not always just about hunting monsters and saving people. Sometimes it's about the smaller things that happen in between.
Warnings: none, just casual life and fluff if you squint
A/N: so I think of headcanons all the time and never write them down, so here you are! Something a little different.
Images in banner from Pinterest
Travelling with the Winchesters meant sitting in the back of the impala, listening with amusement as Sam and Dean bickered relentlessly about who got to team up with you when talking to the locals.
It meant dusty diners and burnt coffee, but no matter where you went and how cheap it was, you were never allowed to pay.
It was late nights after hours of driving, yet you always had to be the first one to shower and get comfortable before they could even think about settling down for the night.
It was them getting protective when random guys tried to buy you drinks or chat to you at bars.
It meant gripping their self control with everything they had when you needed to flirt with other men as part of the job for information.
It was checking you for injuries before a hard hunt had even finished.
It was being patched up with callused fingers and breathing in their cologne when they had to get in close.
It meant helping Sam research lore for a case before sitting close to Dean as he showed you how to clean his gun the correct way.
It meant dragging the boys to a shopping mall to buy new clothes when even your spare set was too bloodstained to salvage - watching them with a grin as they desperately tried not to look at the new underwear you’d thrown in the basket.
Travelling with the Winchesters meant watching shows on Sams laptop whilst sharing Deans pie when you had a rare night off - and you damn well knew that you were the only one who could do that.
✧･ﾟ:dean finds it, less than hidden in your bedside drawers. He turns it in his hands a few times, at first offended. You don’t need a damn toy when you’ve got a perfectly good boyfriend right here. He’s made you cum with just his mouth countless times, his cock so much he worries you’re going to break it, that one time with the single finger, and the other time with just his voice. If he needs to step it up to a damn object, he’s gonna be pissed.
✧･ﾟ:but then he remembers.
✧･ﾟ:you’re just so fun to play with.
When you get home, you don’t stand a chance. He’s sitting on the bed with his legs spread and the vibrator in his hands, a cocky smirk on his handsome face.
“Right here, sweetheart.” He beckons you with two fingers, and you swallow. You can’t help but obey. Dean’s got a hold on you that he still doesn’t fully understand, and if he told you to fall to your knees, you press your cheek against his thick thigh and beg him to put himself in your mouth.
Instead, tonight, he holds you right above him, one massive hand on your waist and the other pressing the head of the vibrator between your thighs. You tremble, clinging to broad, thick shoulders, panting his name as the pleasurable sensation becomes too much to bear. Dean smirks, dragging the toy back and forth, drawing slow, grounding circles on your hip with his thumb.
“That’s it, baby girl,” he coos, watching your every nervous reaction, drinking up your every moan with a smug grin. “Feels so good, doesn’t it? Makes you just wanna fall apart, get really messy, standing up and beggin’ for some more.”
You moan, face burning and body alight with need. Dean drags your panties to the side, pressing the vibrator against your bare clit. You almost jump, but he tugs you right up to his chest, splaying his free hand on your lower back. The feeling is almost too much to bear. You can’t speak, can’t move, can’t do anything but stare at Dean with teary eyes and try not to let your knees give out.
“You’re gettin’ close,” he grunts, because he always knows. “You gonna cum for me, baby?”
You whimper and pull at his hair. He grunts, pressing his face into your neck, and sucks and kisses his way over the soft skin. Up your throat, along your jaw, right to your ear. He nips softly, and whispers in a low, rough voice.
“Let go, pretty girl. Cum all over my fuckin’ hand.”
The orgasm crashes through you, white-hot and wet. You pussy gushes, your eyes roll, and your legs finally give, sending you right into Dean’s lap. He catches you easily, keeping the vibrator pressed against your overstimulated cunt. You writhe and push at his chest, almost unable to take another second, but still grinding down into the overwhelming pleasure. Dean kisses you, deep and bruising, and finally pulls the vibrator away.
“That’s my girl,” he murmurs, leaving light kisses all over your face. “Never gonna get enough of watchin’ you fall apart, baby. Fuckin’ never.”
✦Dean Masterlist - Main Masterlist - read on AO3!✦
✦Author's Note: this one is very specfically self-indulgant i fear but i hope you enjoyed it as well
This is how I imagine my bf feels when I suggest we watch Supernatural together and I’m smiling with all 32 teeth gnawing at my knuckles in the corner the whole episode
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