✧･ﾟ:when he loves you—and he does—after care becomes just as intimate as the sex itself. He’ll spend a few minutes after you’re done laying over you, his face pressed between your breasts as he collects himself, and then he’s moving. Starting a warm bath and heating a towel to clean up the mess he left between your thighs, then carrying you into the steaming water and sitting on the lip of the tub as long as you let him. He gets water and sits you on the toilet after you rinse off, then carries you back to bed. You don’t protest—you couldn’t if you wanted, your thighs made of jelly and your head still a little dazed from the pleasure he wrung from your body—and press you face into his neck and letting him coax a little more food into your before you knock out in his arms.
B = Body part (their favorite body part of theirs and also their partner’s)
✧･ﾟ:if you ask Dean, he’ll say he loves all of you, but both of you know the truth. There’s nothing he loves more than your breasts. Big and bouncing when you ride him, or small and able to fit in the palm of his hand, it doesn’t matter. They’re soft and pretty, almost a toy for him to play with when he has you beneath him. He’ll mouth at them and roll your nipples between his fingers, watching almost obsessively the way your back arches into his touch. It make it easy for him say that his favorite body part is his hands. Anywhere else they’re weapons, coated in blood and dirt and grime, but on your body they’re tools, and he never apricates himself more.
C = Cum (anything to do with cum, basically)
✧･ﾟ:dean loves to mark you up in any way he can. It’s possessive and dirty, but he’s past the point of caring about such things. If he can paint it over your stomach and tits, it’s a good day. A better one when he can smear it on your face, his sore cock twitching when you lick the excess off your lips. But nothing is better than spilling inside of your warm, wet heat. Watching the proof of your effect on him dribbling out of your little hole, down your ass and thighs, it makes him want to bury his face back against you, pushing himself into your with his tongue. If he’s lucky you’ll let him fuck you with slow lazy thrusts after you’ve both finished, making sure he’s driven it properly inside of you. His messy girl.
D = Dirty secret (pretty self explanatory, a dirty secret of theirs)
You pretend you don’t know, but he’s not that good at hiding it. Your underwear doesn’t just grow legs and walk off by itself. Before you were dating, Dean used to steal it used, clenching your panties in one fist and beating his cock with the other. He’d smell that little wet spot and moan your name against the fabric, the arousal and need in his chest just managing to outweigh the shame. Once you’re together, you start just passing them into his hands without a word. The day you let him eat you out through your panties, then keep them after? One of the best of his life.
E = Experience (how experienced are they? do they know what they’re doing?)
Dean’s the first to call himself a whore, as if it doesn’t bother him in the slightest. And it didn’t used to. Sex was for fun, to feel good, to forget about the pain and—for once in his damn life—do something useful for someone else. But after you, it’s different. The experience was just practice, just building up to this. To knowing exactly what women like, exactly what makes them feel good, and using his mastery to turn you into a pretty little puddle beneath him. He’s a champion, and you’re quickly the only game he wants to play.
F = Favorite position (this goes without saying)
There isn’t really a position Dean doesn’t like—he can make anything feel good, and he takes pride in it—but his favorite position soars above the rest of the already high standard. When he’s got you in his lap, brows pressed together, mouth slack and easy to kiss, it’s close to heaven. Your boobs bounce and push against his chest, your ass wiggles in his massive palms, and your cunt hugs his cock just right at the angle. You can ride him until you get whiny, and he can pin you down and fuck up like an animal, watching your face go slack with pleasure, your eyes glazing over and tiny moans of his name falling from swollen lips. You cling to him, and he holds on back, keeping you just as close as you’ll allow.
G = Goofy (are they more serious in the moment? are they humorous? etc.)
Dean lets you set the tone, every time. He’s just happy to be there, and he can make anything work. If you need to be treated like lace, he’s serious and gentle, murmuring low praise and worshiping every inch of your body. If you fall into bed after a date or climb on top of him in the middle of a movie, he’ll tease and joke until you’re whining and glaring at him under lidded, glossy eyes. His shit eating grin won’t fall until you’re screaming his name, and it turns smug and proud. He knows you love it, when it’s easy. He loves it too.
H = Hair (how well groomed are they? does the carpet match the drapes? etc.)
He tries to stay groomed, but life on the road makes it hard. Even when he gets to settle in the bunker for a week or two, shaving isn’t very high on the list of priorities. He does his face because a beard is hard to maintain, and basic maintenance around his cock to keep it clean, but not much else. The look of the tool doesn’t matter much. He knows how to use it right either way.
I = Intimacy (how are they during the moment? the romantic aspect)
When it was just hookups, he sometimes wouldn’t even bother to learn the right name to moan. It wasn’t about being vulnerable or romantic, it was about being a fleeting, passing ship that lent another some warmth. A shadow of intimacy, to stead over the gap in his chest from sinking too deep. But then he had you, and even when you’re play fighting before sex or giggling while he fingers you stupid, there’s a thin layer of adoration under every single kiss and touch. It’s rawer and sharper in the dead of night, when he cradles you in his lap and presses his face against your neck, or folds himself over your body and drives in with slow, torturous thrusts. He’ll never say it allowed, but that’s how he loves you. With a real good show and undying attention, whether the sex is rough or slow or quick in the bathroom, it’s all just to be close to you.
J = Jack off (masturbation headcanon)
Sam used to joke about him taking long showers, but he had no idea. Dean tries to ignore his cock when it gets demanding—when you’d bend over in a skirt or brush past him in the hall—but he started feeling like a teenager with no damn control, and he’d storm into the bathroom to care of himself, quickly and brutally. It gets better after you start dating, but sometimes you have to be apart. Then old habits return, and he finds himself kicking Sammy out of the motel room just so he can pull out a picture of you and jerk himself off.
K = Kink (one or more of their kinks)
There are more of them than he cares to count, but three stand out above the rest. There the only three that can still make Dean, of all men, blush.
Cockwarming until the sun comes up. Holding you around him until you’re dripping and wiggling and whining his name, until he’s so hard it hurts and ends up just rutting into you like a dog. It’s not the filthiness of the act that gets him, but the intimacy of it. You’re so close he can’t tell where he stops and you end, and it makes him so dizzy he almost loses control. He’d trade a life to keep you like that all the time. Soft and completely, totally his.
The first time you call him sir, he almost feels something in him shift. He’d always said he didn’t get that kind of shit—sex was supposed to be give and take, not just a girl doing everything for him—but then he had you below him, babbling the word by sheer accident, and his cock twitched like it had been jumpstarted. He liked it. He liked it too much. He’d follow you like a dog to the end of the earth, but right here, when he was making you feel good, he was the one in charge. He had a handle over the situation, you trusted him to be in charge of you like this, and that tiny whimper of sir made him lose his goddamn mind.
And the breeding kink he tries to hide. He’s not trying to baby trap you, or reduce you to just a body for him to knock up, but the idea of it makes his mouth water. Fucking you so good a little bit of him sticks. Forcing his cum into you until you’re stuffed up, your eyes rolling back in your head from the pleasure. Making you round and glowing with his baby, letting the whole world know just how well he treated you. You notice it, because you always do, and son of a bitch, you encourage him. You let him press his hand flat on your stomach so he can feel his cum spurting into your heat, you cling to his shoulders and moan when he asks if you like it, and he can’t help it. He wants you good and bred. He wants you to be his.
L = Location (favorite places to do the do)
He wouldn’t call himself an exhibitionist, but there aren’t many places he won’t do it. As long as it’s not a crime and you’re comfortable, the bathroom in a police station is as good to go as the kitchen in the bunker. However, there’s nothing he loves more than his bed. A good mattress, the sheets sticking to your skin, the smell of you all around him, it’s almost enough to get him hard all on it’s own.
M = Motivation (what turns them on, gets them going)
The list is so long, he stopped trying to understand it a long time ago. There are the simple things—your mouth around a banana, the curve of your ass, your fingers tracing the line of his jaw, when you get mouthy and bratty and he wants to drag you over his knee or pin your to the wall—but then there’s… other stuff. The time you shoved him and spat in his face after a fight, and he was seconds from splaying you out on the table, squeezing your jaw with one hand and fingering you with the other, all while rutting against your leg like an animal, kissing away the drool when dribbled down your chin. The other time you drove baby for five seconds, and he made you pull over so he could eat you out in the backseat. He’s starting to think it might just be you. He doesn’t really care, either way.
N = No (something they wouldn’t do, turn offs)
When he was younger, Dean would try anything once. The benefit of that is that now he knows what he really doesn’t love. He doesn’t get piss stuff or age play, but he doesn’t count himself one to judge. The one time he let a girl tie him up, he ripped his hands out of the bonds and had a knot in the top of his chest for a week after. Life is hard enough as it is, and as fun as a lot of that kind of stuff looks, there can be too many deep, serrated scars in him for it to feel good.
O = Oral (preference in giving or receiving, skill, etc.)
While he’ll never say no to getting some head, the only sight better than you on your knees with his cock in your mouth is you flat on your back, grabbing at anything you can reach as he tongue fucks you into oblivion. He thinks he could live and die between your legs, your pussy gushing on his face and his name falling from your lips. And he’s good at it. He knows he’s good at it. He’ll shoot you a wink before he kisses his way down your body, because he knows you’re never even try to resist him. Once he convinced you to sit on his face, and he’d never known anything closer to heaven.
P = Pace (are they fast and rough? slow and sensual? etc.)
He can read and match the tone well, depending on what you want. When he’s rough, he bullies his cock into your like a drill, making the bed creak and tears spring into your eyes from the almost overwhelming pleasure of being fucked over and over and over like some sweet little doll. When he’s slow, he’s slow, taking his time to make your feel every thrust, every kiss, every brush of his fingers over your clit. But even when he’s slow, he drives into you with the force of a man falling into a black hole. He can’t help himself. The way your gummy walls squeeze him just feels too good, to not make them clench and flutter around him.
Q = Quickie (their opinions on quickies, how often, etc.)
If you’d let him, Dean would just fill the whole day with quickies. Wake up and fuck you between the sheets, get breakfast then have a second meal between your thighs, interview a few vics and cradle your head while he drive, pulling off to the side when you suck his cock a little too well, and his vision starts to go blurry. Sometimes he’ll spend a whole day teasing you, just to try and get you to start it. It’s a great victory, if you drag him into a supply closet to bang one out. It’s all he’s ever wanted in the world.
R = Risk (are they game to experiment? do they take risks? etc.)
Anything once really did teach him to know what he liked, so at this point it’s more indulging any risks you’d want to take. He knows his lines, and he’s more than willing to help you find yours. If you shyly ask him to tie you up or wrap a hand around your throat or fist you, he’d have to be a madman to tell you no.
S = Stamina (how many rounds can they go for? how long do they last?)
Even at his age, Dean counts himself impressive. He might not be pulling the day long marathons he did in his twenties, but he can go the whole night if he keeps the focus on your pleasure, which he finds easy to do. If you make him cum in your mouth or hands, he’ll dedicate as long as he needs to teaching you a few lessons and opening you up, before he’s hard and ready to go again. Once he’s in you, though, he’s no chump. He can hold himself off for over an hour on the best of nights. Sure, there were the few cases when you were just too soft and pretty and he couldn’t stop himself, but you found it hot anyway. The loss of control, just from looking at you, you’d never felt more beautiful. And it wasn’t like he didn’t make it worth your time.
T = Toys (do they own toys? do they use them? on a partner or themselves?)
He’s tried a few toys on himself, but they’re all complicated, and he lives with his damn brother. Knowing each other’s porn habits is bad enough, the idea of sex toys getting exposed makes him feel a little sex. He’s got a perfectly good hand, and a hot girlfriend, and that’s all he’s never going to need. If you want him to pull out that vibrator you keep in your nightstand, though, he’s never going to protest. Watching you come apart—your thighs rolling against the head of the toy and your mouth hanging open—is always too good an opportunity to pass up. The toy might be the one giving you the pleasure, but Dean’s the one holding it. He’s the person you’re crying for when you cum, and he usually gets to fuck your already swollen pussy after. Doesn’t get much better than that.
U = Unfair (how much they like to tease)
Some might call him a monster. And the some is you. You didn’t know how much you could get worked up, until Dean came around and showed you. Through the day he’ll make you flush with little comments, then trace his fingers over your inner thigh in the car, making you flush and pant before he just kisses your cheek and walks away. And you thought that was bad, until he actually got his hands on you, and you learned how much the asshole loves edging. Getting you so wet and flustered your almost sobbing for him, whispering dirty praise until your face is burning, somehow keeping you on the edge with teasing touches, even as his cock drives right into that gummy spot inside of you. He says you’re too adorable not to tease. You roll your eyes, but never ask him to stop. It’s always, just a little, too good.
V = Volume (how loud they are, what sounds they make, etc.)
The mouth on him should be worthy of a lawsuit. Between the moaning and grunting, the strangled, rumbling sound he makes when he pushes himself inside of you, and the deep, filthy dirty talk, you think you might just be able to cum from his voice. It’s not fair, but Dean doesn’t play fair, and you don’t want him to. One day, when you’re brave, you’ll ask him to test the theory. He’ll oblige, and you’ll certainly end up right.
W = Wild card (a random headcanon for the character)
Dean’s never in it for himself. If his partner wants him to hand over control, he’ll do it, but it’s never going to be what he prefers. He spends every day of his life begging for the people he loves to listen to him, for once in their damn lives. He’s got a grip over his own world, even if his hands shake on the worst of nights. It’s not liberating for him to be degraded in sex when all he’s known is bruises and spit from the people who were supposed to love him. He wants to be trusted more than he’s ever going to be able to say, to be the only person you turn to for pleasure, to take his hands and mouth and body and have them feel safe for just one, one fucking person. He might be in control during sex, but it’s still all about you, and that’s exactly how he likes it.
X = X-ray (let’s see what’s going on under those clothes)
He doesn’t get his confidence from nowhere. For a while—before you—it was sort of the only kind of confidence he had. Dean didn’t count himself for much, but no one could deny their own eyes. The size of him is one thing—long enough to hit spots you didn’t know you had, veiny and uncut and almost pretty—but the girth- It makes your mouth fall open, the first time you see it. You’re not sure you can stretch that wide, and when Dean tells you that you will, sweetheart, you almost roll your eyes. But, damn him, he’s right. You mold around that thick, big cock like a glove, and feel him in every inch of your body.
Y = Yearning (how high is their sex drive?)
If anything, he only gets worse with age. In his younger days, fucking was something he could work himself up to almost any day of the week, even if he wasn’t sure he wanted to an hour ago. A pretty girl and a good drink, the engine could get itself going. Then you came along and made him feel things, and then he let you get close and start making him eat well and drink water and go for stupid walks, and suddenly there isn’t a second that’s enough. If life didn’t get in the way, he’d never let you leave the bed.
Z = Zzz (how quickly they fall asleep afterwards)
He’ll push through the exhaustion for some proper aftercare, but the moment he’s sure you’re good, Dean’s out like a stone. He doesn’t sleep well under any other circumstance, but you work him hard, then let him use you like a human body pillow, and he finds the closest thing he knows to peace, right there, with you in his arms.
✦Dean Masterlist - Main Masterlist - read on AO3!✦
✦Author's Note: i think about him. all the time <3✦
⊹₊ ⋆ 〔ㅤㅤㅤㅤㅤㅤㅤ part of my dean winchester, who… series. 〕
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dean was an absolute god at sex. you knew that. everyone on the planet probably knew that.
every single girl that’s ever left his motel room that you’ve seen has had a smile on their face that could light up a small country—and obviously, that didn’t come from not doing a good job of dicking down a woman.
you should’ve known he’d be just as good at the aftercare, too. you really should've.
and sure, you wondered what it would be like, to be with him. of course you did. and you let yourself ponder and fantasize, but never acted on your urges. sure, you flirted back with dean when he flirted with you, because it was just make-believe. it was funny. it was a joke, and it was easy.
and it was a joke between you for a long time. yet somewhere along the way, that changed.
that’s how you got yourself to right now: laying in dean’s bed. on dean’s sheets.
in dean’s arms.
he’s never brought a girl back to the bunker—so that’s gotta count for something, you think as you lay in his bed. you’ve never seen a girl walking out of dean’s room in the bunker like you see when you stay at motels, so maybe you did matter more to him like he said you did. you let yourself believe it, even if it really wasn’t exactly true. let yourself believe that maybe this wouldn't end tonight, maybe you’d have something more with dean.
but you can’t really even think about that—or anything else, for that matter, because in your time together, dean made you come 4 times. you’d never been able to do that in one sitting—by yourself or otherwise, at least not without breaks in between—but dean was wringing you out for all you were.
and you gave it to him. willingly. truly.
you were barely making coherent noises by the end, on your last orgasm. and you were loud. and it sounded like you were in pain—thank god sam was gone, because you felt embarrassed, so goddamn embarrassed to be making such noises. but dean quite literally fucked the self-consciousness right out of you. he pressed his nose to your cheek like the tip of his dick pressed deep inside you—and when you poorly stifiled a moan that was coming out of you, he just shook his head against yours and said to let him hear it.
dean told you that he could hear your thoughts from here. he told you to just enjoy it. told you that you could say stop if you felt too overwhelmed, and he would. he said most of that while he pounded into you, so it was hard to focus on his words.
but you still heard him.
yet you didn’t tell him to stop.
he also shushed you when you tried to apologize for essentially being a ragdoll instead of an engaging member of sex with him after the third time you came. he didn't mind, he said. said he got off on it, watching you come undone, over and over, getting drunk on him. and you should've expected this kind of reassurance from him, you really should've. he provides in every other possible way, in every sense—so how could sex be any different?
you’re close to dozing off now, though. you can distinctly feel dean’s body still on top of yours—he’d also gone full ragdoll after holding off his own orgasm for so long—but that’s about all you can feel, besides the throbbing from your lower region, which is still wrapped around dean.
you're wet in every sense—sweat, fluids, basically a puddle of yourself. you’re starting to feel sticky from yours and dean’s fluids mixed together as your senses come back, but you don’t move. you’re too tired. your eyes are just so heavy, so you just close them. allow the aftermath of the experience you just had to wash over you completely, leaving you all floaty-like and celestial. your hands are still resting on dean’s back, somewhere by his shoulder blades, no longer hanging on for dear life, now just holding him. you still don't move, save for breathing.
then, it could've been seconds, it could've been hours—but dean finally stirs enough to look up at you from where he lay on top of you, rests his chin on your chest right bewteen your boobs. the movement makes you look down at him, too—but don't get it twisted, you just open your eyes enough to look at dean. you’re still wiped.
and dean just looks at you, doesn't say anything right away. he blinks a few times, then reaches up to your face, brushes his fingers against your cheek. the corner of his mouth twitches up a little, and if you were the tinest bit more coherent, you’d probably feel embarrassed—but you aren’t coherent.
now, you're too tired to care if he thinks you’ve lost all your appeal, now that the sex is over. now that there’s nothing new to discover, now that he’s scratched the itch. too tired to care if he’s gonna kick you out back to your room, because now you’re all sweaty and gross and sticky, no longer a shining star, no longer something to be conquered.
but he doesn't do that.
instead, his fingers continue to gently caress the side of your face, over and over. like he was trying to memorize it. then he lifts his chin and places a kiss on your chest. then another kiss before he lifts himself up off and completely out of you with a small grunt—and for a split second you think he’s gonna leave you here, but then his face comes completely into view above you, his nose brushing yours again.
“y’got any idea how perfect y’are?”
the slurred words catch you off-guard—but that’s a severe understatement. you don't hear the word ‘perfect’ from dean often, and certainly not after he was just balls-deep inside of you, moaning your name over and over again. touching you. wanting you. needing you.
dean doesn’t let you answer his question, though. he just kisses the side of one of your cheeks, murmuring a ‘b’right back’ against your face, inking the reassurance in your skin before you can even attempt to say anything or reach for him. then he moves, and you hear a squeak of the sink in the corner of his room, hear his footsteps padding back over to you against the concrete a few beats later.
dean’s hand touches you first—sliding up your leg gently, and you’re certain he’s making sure he doesn’t scare you, since you’re laying there deader than a sack of potatoes. you hum when he does, moving a little—or at least trying to, but he shakes his head at you, his other hand pressing you down on his bed.
his bed.
jesus. his bed. the pillow smells like him, everything fucking smells like him. it’s invading every pore of your body. your heart’s still pounding, but it’s slowing down when dean moves away from your face again. you feel warmth between your thighs, and look down, squinting in the dim light to see what dean was wiping you with.
it’s his shirt he was wearing, the one you yanked off of him earlier. he’d gotten it wet in his sink with warm water, and was currently wiping at the creases of your thighs, slick and sticky with dampess up with his shirt.
you don’t know why he was doing this. did he do this with everyone he hooked up with? you tried not to think about it, but now that the fog was finally starting to clear in your mind, it was hard not to. the gesture, the view of him in front of you on his bed? it puts a lump in your throat.
you’re in love with him.
you’ve been in love with him for a long time.
and you know he’s probably just as tired as you—he’d done pretty much all the work sex-wise, but you noticed and knew he liked it, being the giver. always giving, never asking for anything. taking care of you.
and you let him.
four times.
but you also noticed he was getting tired at the end. he almost tuckered out, tossed in the towel, and didn’t come at all. he was panting as hard as you were on the last round, and he was just as sweaty. held it off until it almost hurt, like he didn't want it to end. he was speaking all sorts of rambles too, his words stringing together.
you can still see, even in just the dim, barely-there golden light of his room that his face is red. not pink. not blushing. beet fucking red. you can see his shoulders rising and falling quickly with each breath, and you want to reach up to touch him. but you’re not sure about doing it, so you resort to blindly grabbing at him until your hand makes contact with him.
your hand ends up somewhere on his arm—and he looks at your hand on his skin, then looks up at you with those green eyes.
“come up here,” you murmur, tugging his arm—and he moves like there’s an anvil attached him that you pulled on, rising over you just enough to not squish you with his body weight.
your hand on dean’s arm finds purchase on his face as you rise and turn—and dean molds to you like a slab of clay, letting you do what you want. he lets himself lay down next to you instead of over you, like before. your body’s moving him mindlessly without barely touching him—and you just look at him when his head hits his pillow, both your chests rising and falling slower now.
you wish you could tell him he doesn’t have to take care of you. tell him that he’s allowed to rest here with you, allowed to not be… dean winchester. the sex god, the caretaker, always having to be on. you wish you could say that he’s allowed to just be dean instead. you don’t know how to tell him that.
but the thing is: dean already knows.
he knows that he’s allowed to shell out his own little part of you to hide out inside when things get too bad. he knows that you’ll always be there for him—for every nightmare, every apocalypse, every angel and demon that has a hitlist. he knows you’ll hug him without him having to ask, and even patch him up if you come across him drinking by himself in the bunker instead of getting the first aid kit. you’ll gently coax him awake when he falls asleep at the library’s table and quite literally drag him to his own bed, muttering about how this is why his back hurts all the time and other righteous, nice things—because you care about him.
and he cares about you.
he’s been a goner for you.
he’s in love with you, too.
that’s why he’ll take everything you have to offer him, over and over. he’ll let you hold him until the sun inevitably comes up again after a nightmare, let your hands touch him when he fall asleep with his laptop and a bunch of books open—and why he barely flinches when he hears your voice in his ears, waking him up, and he’ll let you tow him to his bedroom.
your hands move, reaching for something—dean looks up out of his thoughts to see what it is.
it’s his shirt.
you sit up more, hair sticking up, bunched and messy from dean’s hands running through it—and he’s never seen anything more beautiful. anything more perfect. he’s distracted by your face, your body, so he doesn't really register what you’re doing until he feels his wet shirt on his skin. you’re wiping him off, like he did for you. that’s when it hits him.
you’re trying to take care of him, too.
he looks down at his shirt that’s wiping his own skin, wiping away his own fluids mixed with yours. he’s unable to move or look away from the sight. unable to breathe. in all his years, no one’s done this for him: taken the time to take care of him. to let him be the one taking a break.
your other hand’s gently brushing his skin at his hipbone, almost as softly as his shirt. he blinks, blearily. it’s hard to keep his eyes open, and he can feel his body slowly starting to succumb to sleep under your touch, your care, just laying here in the warmth of you laying by his side—albeit propped up next to him.
he wants to tell you that you don’t have to do this. that he’s perfectly okay with being the caretaker, the one who carries it all. he’s been cast aside like a used tissue after sex—and he’s done the same too, so really, he shouldn’t feel so empty about that when it happens to him, but he does. he’ll take it. take it and bury it deep instead of letting himself feel it. that’s all he knows, all he can do. because he can’t try to unpack everything, not now.
truly, he doesn’t mind if no one ever took care of him—because he’s not allowed to mind. he’s not allowed to feel any sort of way about taking care of others, he just has to do it. no questions, no talkback, no lip. because that’s his job. most of the time, he just ends up pushing people away. he’s not good at showing anything other than anger. but he has everyone taken care of, in the end. at least he has that.
dean doesn’t tell you to stop doesn’t tell you to get off him, or make a joke as you wipe at him. he doesn’t do anything, actually. not a damn thing. he’s not sure why, either. he’s pretty sure he blacked out, instead of being present in the moment. he’s been doing that a lot recently—not knowing what he’s doing, lost in his own thoughts, brain on autopilot. he almost walked into a sign in front of a restaurant in the middle of the sidewalk the other day. a goddamn sign. what the hell was wrong with him lately?
dean finally snaps back into the moment, slowly blinking his eyes at you like an owl. he swallows the words that never came, that never even formed into a thought as looks at you. you're still naked—and that is a sight dean could get used to, that’s for damn sure.
you turn and lean over the edge of his bed a little, and dean immediatley siezes up, a sinking, deveastating feeling weighing on his chest like a dumbell, because this is it. you’re leaving. you got what you wanted, just his body, just to get off, and now you’re leaving. he’s given you everything and more and you’re leaving, leaving him like a toy you don’t want to play with anymore, leaving him like everything and everyone in his life. you’ve already grown bored of him, and now this thing between you is over before it even began.
but then you turn back to face him, your entire expression soft.
you were just putting his shirt you were using on the floor.
oh.
dean tries to look like he didn’t just get scared, but he knows some part of you noticed. he’s vulnrable right now, a easy target. you could walk out his bedroom door right now and he’d probably just cry instead of going after you. he actually feels like he could cry on the spot right now. he hopes you won’t say anything. you usually don’t—just hold him, hug him, touch him without a word.
and oh, how dean loved to be touched by you.
he’d take 40 more years in hell if it meant your hand could brush his face one last time. he’d take an eternity of torture, or he himself doing the torturing in the pit for your arms around him again. he’d kill anyone, steal anything, do whatever it took if it meant being near you.
but he has to act like he wouldn’t do that for you. he’d burn down anything for you to even look in his direction, for your touch on his flannel-clad shoulder, for your kiss on his cheek, an embrace from your arms. yet he had to act normal about it. but you were the only one who knew how to hug him correctly. sam, knew too, by default. but that was different—that’s his brother. his blood.
but you touched him like you’d spent your whole life learning to.
and you even hugged him like second nature, but still molded to the moment, still exactly what he needed. because you always knew where to squeeze, where to rest your head on him, no matter the situation. no matter if you won a hunt, a fight, an apocolaypse, or if you lost, you fit his body like a puzzle piece. like a lock and key. he’d known that—but it was carved into him forever after tonight, and he’d never forget.
because earlier, when he first slid inside you, it’s like the whole world had been off-kilter until he found his way inside you, the way he’s wanted to be inside you for so long. once he’d bottomed out, it’s like the world was right, for once in his life. like everything made sense after so long of it being chaos.
dean knows it’s ridiculous to feel such a thing, especially during sex, but in that moment, he did. he fit so snug, so perfect inside you that it felt like he’d gotten chucked into one of his dreams again, where he was watching you below him, you touching him the way he’s wanted you to touch him for so long. moaning his name, bringing him closer to you with your hands. just for the sake of being close, touching.
he’s been waiting for it. since forever, it feels like. since the moment he laid eyes on you. since the moment he had even an idea of what love was.
he must’ve been staring pretty hard, because one of your hands had made its way up to the side of his face, your eyes searching his expression. you’re looking to see what he’s thinking about. dean hopes it’s not written all over his face, but you seem to know what he’s thinking regardless if his expression shows it or not.
your thumbs brush his cheeks once, twice—still searching. still wanting him. he honestly still can't believe it. he’s not sure he ever will. you being here with him, he’s sure to wake up from this dream at any moment.
but he doesn't. you’re still in front of him. touching him.
and you want him there.
that’s why he lays down and rests his head on your chest with no complaints, no pushback when you tug him towards you after you lay down yourself. he doesn't protest partly because he actually really was fucking tired, but mostly because eventually, you’ll leave him—and dean will have nothing but the memoty of you, of your touch. maybe that’ll be changed, now that you’ve crossed the line he’s wanted to cross for so long now.
your hand finds his way into his hair, gently running your fingers through it and tugging dean out of his thoughts—and he has to bite back a noise from how good it feels. he sighs softly instead, relaxing more on top of you. he wonders if he’s making it hard for you to breathe. it’s happened before.
but you don’t move.
and now he can die happy.
dean would die for anything. it was damn near inevitable in this line of work—and shit, it already happened. he’d die for you, for his brother, his father, or some random person he doesn’t even know. he’ll lay it all down, if it meant saving the world, or even just saving one life. he’d do it. he has done it, over and over.
but you don’t say anything. you just hold him. dean can feel your heartbeat, feel your chest rising and falling. and in that piece of sunlight and everything warm and good, dean knows. he’s always known the terrifying truth about you.
in 𝓌hich ﹒ ﹒ ﹒ you ask dean to do your laundry & he finds his new favorite hobby !! 𝗉𝖾𝗋𝗏𝗒! 𝖽𝖾𝖺𝗇 𝗉𝖺𝗇𝗍𝗒 𝗄𝗂𝗇𝗄 𝗆𝖺𝗌𝗍𝗎𝗋𝖻𝖺𝗍𝗂𝗈𝗇 𝗅𝖺𝖼𝖾 𝗄𝗂𝗇𝗄 ⦂ 𓈒ּུ𓂃༷ ✶˚ 𝟴𝟭𝟱 .
⠀﹒ ❤︎ ' for a hunter, you had the largest collection of lacey bras and underwear. they all matched, had pretty designs, fit perfectly; dean knew. obviously, he’d seen your underwear before, you were on the road together.
usually though, laundry was your job once you got to motels. you knew how to do it best. but this time, you’d ask dean to do it while you followed a lead that was easiest for you rather than a man. he hadn’t thought much of it when he agreed, but boy, was he rethinking it now.
“fuck?” he dangled a pretty lilac purple thong on his thumb, staring at the thing like it was the strangest object he’d ever seen. but when he held it up right, his back straightened. it was so… pretty. placing it on the bed next to him and reaching down into the basket. dean pulls out pair after pair, almost in a trance.
they were such delicate little things, too perfect. each one was prettier than the next, all spread out around his lap after he finished folding the rest of your clothes. he was just stuck on these and the fact that they were yours.
dean picks up the pretty pink pair, maybe one of the skimpiest ones. letting out a shaky sigh, he stares at it in his hands. and with the way his cock twitched and strained against the confinement of his jeans? he knew he was in trouble. desire and lust crept up his neck all too fast, taking over his thoughts.
pictures of you flashed in his mind; fully clothed, naked, with these on. dean took a deep breath, tongue wetting his dry lips as he closed his eyes and imagined this baby pink against the color of your skin. he imagined the way they’d fit on you, hug your hips just right.
before dean knew it, his hand was on his crotch, palming himself slowly. “fuck me..” he grunts, giving into his newfound desire.
quickly getting up, dean grabs another little black pair, clutching it with the pink one in his fist as he tosses the rest into the basket of your clothes. he nearly trips over himself as he stumbles into the small bathroom, shutting and locking the door behind him. he leans against it, breathing deep as his other hand shakily unbuttons and unzips his jeans. ‘this isn’t bad, right? they’re clean.’ he’d convince himself, freeing his now throbbing length from his boxers.
his thick girth was swollen with a deep blushy head, leaky with pre already. god, he was so turned on. and he could only pray that you or sam weren’t on your way home right now, he’d be fucked.
dean collects the precum from his sticky tip, smearing it up and down his cock with his spit covered palm. “oh my..” he groans, tightening his grip. he peaks an eye open, reaching for the lace on the counter before wrapping it around his veiny shaft, stroking himself with it. “fuckfuckfuck—”
a knot ties in his stomach as the need for pleasure overtakes any sense of wrong from right. the rough fabric of the lacey panties mixed with the thought of you was more than enough for him.
images of you flash behind his eyelids again, what you’d say, how you’d sound, how you’d feel. “god, you’d feel so fucking perfect, sweetheart.” he moans, stickier sounds emerging. “i need you.. need you so bad.” his hand jerked himself faster, on the verge of release. “i can’t—” the lace provided just the right amount of friction against him, resulting in his hips fucking into his hand wildly. the desire for you was so strong, more than what the lace could provide, but it sufficed.
with one last squeezing stroke, dean’s release hit him like a damn truck, sending him hunching over the bathroom counter as his seed shot out in quick, warm spurts. it got on the cabinets, his thighs, and your panties still tightly wrapped around him. his abdomen flexes as he cums, the white-hot pleasure damn near making him see stars. “aaah… oh, fuck-fucking hell…” he moaned, panting as a thin layer of sweat beaded on his forehead.
reality slowly set in, but dean couldn’t find it in him to feel guilty. not now. he stayed like that for a while, just breathing into the air as he lets go of his softening cock. “m’so screwed…” he stares down at the one pristine and clean pink lace, now stained and ruined with his cum. he hated to admit the sight made his pulse jump again.
dean quickly washed up, rinsing the evidence off your panties and hiding that single pair with his stuff. maybe you wouldn’t notice. he hoped you wouldn’t notice. dean also hoped you would ask him to do the laundry more often without questions of why your underwear started disappearing.
you come home to dean after a long day, one where you can barely make it through the door, your body dragging along as you pull yourself into the living room.
dean's on the couch, his legs stretched out in front of him, feet propped up on the ottoman. there's an old movie playing on the tv, but you don't pay attention, wordlessly plopping down beside him as you rest your head on his thighs.
you make a small sound, maybe looking for some attention, though you won't admit it. before you can say anything, his palm is resting on your head, warm as he massages your scalp.
"bad day?" he asks softly, sparing you a quick glance before his attention is back on the movie.
in a way, you're both like cats; desperate for closeness, but not wanting to draw any attention to it. dean's not the type to push, though he also knows you wouldn’t react well if he tried.
you're both content resting in comfortable silence.
"just tired," you reply, letting yourself sink deeper into the couch as you close your eyes.
dean makes a sound, something close to an agreement, before shifting his hands to your neck, then your shoulders, working out the tension.
"want a drink?" dean asks softly. he's halfway though his beer, considering grabbing another, but you're too sleepy to sit up and sip at one.
"'m fine," you say softly, curling your legs behind you. "thanks.”
"okay." he goes back to playing with your hair, almost absent-mindedly. there's a funny scene on—you don't catch what's happening, but dean makes a half-hearted snort of amusement. "let me know if you change your mind."
you hum in return, already falling asleep to the soft sounds of the television and dean's fingers in your hair. the sun's barely even set, but you're too tired to move.
when you fall asleep, you miss the small smile on dean's face. he still hasn't said i love you—neither of you have—but you know it's true. you feel it every moment you’re together.
part 9 of @bejeweledinterludes’ headcanons series.
📨 had to bring dork dean back. so many people (2) expressed their love for him. so i must oblige.
✎﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏﹏
hey so. breaking news here: the hunter, dean winchester? that one guy who looks evil in the eye daily, who has killed damn near every supernatural creature on the planet, drives a badass car and is a known player? yeah, he’s actually a big, fat dork.
first off, just stating the obvious: he seems to know every single movie, tv show, and pop culture reference in the entire history of television and media. it’s a little insane, how quick he can reference something—and do it correctly.
same with books. “hey, i read”, dean said, and he was not kidding. mostly because he stole read the classics sam had permanently stashed in the bottom of his backpack from the ages of 9 to 17 and paid attention in english class (when he actually went) and the assigned reading was actually good for once.
also, it’s not just anyone calling dean a dork. sam calls him a dork. and you call him a dork—because dean is one.
he was rambling on passionately about either a car show he went to back in the day or something about a slasher movie he just rewatched, and you said it: “you’re such a dork.”
dean wasn’t too sure how to react. he’s been called worse—much, much worse than that. and you sorta smiled when you said it, so it couldn’t be that bad. so dean took it as a compliment.
he gets excited over the little things. he gets mach-levels of elated over the most mediocre of events: a new beer at the liquor store, a stumping word search in the newspaper. he treats things like that as if it was gold. and maybe to him, it is.
maybe it’s his inner child he never got to be peeking out through him once in a while, or maybe it’s just because he’s comfortable around you—but more and more, you see a softer, sillier side come out of him.
it’s even worse when he’s drunk. he gets all dopey and happy under the influence sometimes instead of destroying a room like the tasmanian devil. he hangs off your shoulder, talking all sorts of nonsense: “hey, did y’know that bats have echolocation? i saw it on tv.”, and “ya think space smells weird? or does it jus’ smell like… nothin’?”. but you don’t make fun of him—at least, not too hard.
he laughs at the jokes in movies he’s seen over a hundred times. he reads graphic novels and has strong opinions on today’s horror genre compared to what it used to be. he grins when he gets a good message in the his fortune cookie and dresses as a cowboy almost every year for halloween. so yes. dean winchester is a major dork.
Sam’s the one who starts it. One afternoon, he pulls you aside with that conspiratorial glint in his eyes and goes, “Wanna know something that’ll change your life?” Obviously, you’re listening. Sam leans in and murmurs, “Dean always throws scissors in rock-paper-scissors. Like… always. He’s been doing it since we were kids.” It’s so stupidly specific you almost don’t believe him — but Sam’s face says trust me.
So you test it. First game, you go, “Rock, paper, scissors — shoot,” and Dean flashes scissors like he was born doing it. You drop rock, annihilate him instantly. His expression is priceless: full confusion, full offense. “Whoa, no way,” he mutters, “best two outta three.” But it doesn’t matter. He’s scissors every single time. And soon? You’re unstoppable.
You start using this new power for everything. Last slice of pie? Rock beats scissors. Who gets shotgun? Rock beats scissors. Who has to talk to the cranky sheriff? Rock beats scissors. You’re collecting victories like Pokémon. Sam watches from the sidelines, smug as hell, like a proud mentor watching his student go feral. Meanwhile, Dean is…unraveling. He accuses you of cheating, witchcraft, telepathy — “messing with the air around his hand,” which isn’t even a thing, but he swears it is.
Eventually, he gets paranoid enough to make you play with his back to you so you can’t “read him.”
Spoiler: it’s still scissors.
And when he finally decides to be unpredictable for the first time ever and switches to paper? You’ve already evolved like a predator in the wild and beat him with scissors without missing a beat. The sound he makes is a mix between a dying engine and an offended cat. Sam nearly passes out laughing.
Dean, for the record, is equal parts annoyed and undeniably attracted to you — and there’s nothing he can do about it.
──★˙. He's determined to raise him better than John raised him and Sam. He's always been adamant on this--the idea of his kid falling into the same routine he did as a child petrifies him.
──★˙. They roughhouse constantly. Nerf-Gun wars, backyard wrestling--you name it. It gives you a heart attack every time.
──★˙. Dean never reads him fairytales. Only comic books. Captain America, Batman, Ghost Rider. Your baby always falls asleep in his arms.
──★˙. Dean always saves his drawings. Especially if the ones are of Dean as a superhero. It wrecks him every time--he thinks he doesn't deserve it, but he seriously does. He just doesn't see it like you do.
──★˙. He calls him “Buddy,” “Champ,” or “Little Man.” It makes his son beam. Sometimes Dean says “Kiddo,” just like John did to him—but only when he’s soft, never when he’s angry.
──★˙. They watch monster movies together, but Dean pretends they’re fake. Dean wants his kid to believe in the boogeyman only when he’s old enough to handle the truth.
So I have a Destial headcannon that Cas watches Dean sleep, but not in like the "he's so peaceful when he's sleeping" way more so in the "Please dont stop breathing" way.
At first it was just listening for his breathing even of he was thousandsof miles away he would still check for it every now and then.
It started after he pulled Dean from hell. He could rationalize it as making sure his charge was safe.
Then Dean died, and suddenly it wasn't enough anymore. He told himself he was just being vigilant, and would pop in the room every couple of hours just to check.
Then even that wasn't enough to calm his unease, and it soon got to the point of Cas needing to watch Dean's chest slowly rise and fall in the same rythmic pattern he had memorized, and if Dean even slightly strays from that pattern he panics.
He has shaken Dean awake before simply because he was breathing weirdly in his sleep after his ribs broke from a hunt.
The first night he did it though, he didn't wait for Dean to fall asleep, and Dean was creeped out by the angle just sitting there stairing at him from across the room.
After awhile of him just staring Dean finally told Cas to atleast get a book or do something other than just stare. Now Cas sits in bed with him and reads, or runs his hands along Deans back or arm until the man is asleep.
