A Bunny and Her Jackrabbit

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✦