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A Brief Sexual History of Dean Winchester

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It's not the first guy Dean flirts with that gets into his pants, or the second, or even third. Not the Statie or the insurance salesman or even the super-gay bartender who gets him roaring drunk. No, it's the unassuming middle-aged banker, the one his dad sends him to hit up for information on the vic's financials.

It isn't that Dean can't take the guy. There are very few guys Dean can't take at seventeen, and certainly not this guy, who's shorter and scrawnier than Dean. It's that the dude's almost dad's age, and he just looks so pathetically grateful for Dean's interest. Dean's always had a weird respect-your-elders streak.

He hadn't gone overboard on the flirting, either, just some big eyes and one suggestive remark, but the guy's salivating like Dean'd stripped naked and laid himself out on the desk. The guy's nervous eyes flick back and forth between Dean's face and his dick. Okay, so the jeans might be a little tight, but that's kind of the point. Dean's stuck; not sure how to get out of the situation without blowing his cover or breaking the guy's nose – and that's just out of the question. So when the guy reaches out a tentative hand, Dean figures, what the hell. He hasn't gotten laid in a while anyway. Turns out, the guy just wants to suck his dick, and a blowjob is a blowjob – Dean sure isn't complaining.


For the first six months or so, his dad has to nudge him every time. Only the guys – Dean's already charming the pants off the ladies out of habit. Mixing business with pleasure is fast becoming a specialty.

Once he starts paying attention, he can't miss it. He can tell who's into him or his dad, or, for a few perverted guys, Sammy. Dean gets in between them and Sam, shifting their interest to him, when possible, and if that doesn't work, then he warns them off.

There aren't that many, really. Sam's always been a weird-looking kid. He was a little chubby before he got his first growth spurt, and then just before he turned thirteen he got another that made him look like a giant string bean, all flailing arms and shaggy hair. Women love him, especially thirty-something waitresses with kids at home. Sam can charm them out of half the food in the diner if he has a mind.

The guys that like Sam, though, they always have that creepy uncle vibe, and Dean usually just keeps himself staunchly between them and his brother, staring them down until they look away. He wonders how often Dad had to do that for him when he was Sam's age.


The second and third guys give him head too, and Dean doesn't really think he'll be this lucky for the rest of life, but he also knows he's putting on muscle, losing some of his boyish looks and baby fat. A lot of the guys expect him to make the first move. When he doesn't, they sit there looking dejected, just like the women he strings along for information. The few who push their luck are usually bigger, self-confident guys, but even most of them will back off if he bristles. He knows he's a scary motherfucker when he's got his back up, so the only ones that push it have more muscles than brains and usually end up going home with a black eye.


The fourth guy he's with is just a misunderstanding. "Please," he says, before Dean can gracefully exit the scene, "blowjob?" And Dean figures, why not? It's not like a blowjob is ever a bad thing.

Then the guy unzips his own pants and Dean thinks again. He's not a welsher though, so Dean gives his first blowjob in the back room of a morgue to a guy only a couple years older than he is.


Sometimes, he wonders exactly what his dad thought would happen. Did he really think Dean would walk away from all those guys he was flirting with and never get felt up or backed up against a wall to have to fight or fuck his way out of it?

They talk about it indirectly one night, over beers shared while they watch Sammy sleep in the middle of a pile of books on his bed. Dean tells Dad the story about the pity fuck he'd given the shy, plain girl who'd accidentally given them a huge break in the case. She'd just looked so damn hopeful that Dean couldn't break her heart. It was pretty good sex too, which just goes to show he should stop judging books by their covers.

"Just wait till you get to be my age, son," his dad says, with a sly grin. "Then it'll be you that gets the pity fucks." Dean doesn't believe it for a second. He's seen the way women look at his dad, but he just rolls his eyes and takes another beer.


Dean stops counting somewhere around twelve – all blowjobs. He's just lucked out, it seems.

Or guys are just that easy.

It's almost always a blowjob for him; sometimes a blowjob for the other guy, if he's feeling particularly magnanimous or completely uninterested. He never thought there would be actual sex though, since he isn't planning on fucking any guys, and his ass is strictly off-limits except for maybe a little groping.

That's before Johnny in Cedar Rapids, Iowa. Johnny's a kid, eighteen at most. Probably only seventeen. He's the vic's best friend, and Sam isn't around to provide that puppy dog look of moral support that he does so well.

So maybe Dean overdoes it a bit, trying to be nice to the kid. He isn't even flirting – just trying to be a good listener – but Johnny gets all up in his face and starts kissing, and Dean's a sucker for kissing. Why not, he figures, why not give the kid a little make out session; something to remember him by. Johnny crawls right up on his lap though, and his pretty hands and squirming fingers make their way under Dean's shirt. Dean starts to protest, but then Johnny's unzipping Dean's pants and it's blowjob time again. Dean still feels a little bad for the kid, though, so he knocks Johnny's hands away and goes down on him instead. It's hotter than it usually is with guys; generally, it's a chore that Dean just tries to get through, but Johnny's leaning back against the wall, shivering and moaning, and Dean is probably a perv for actually getting hard while blowing someone so young.

Then Johnny asks Dean to fuck him.

No one's ever asked Dean for that, not even women he's spent hours on foreplay with. And Dean doesn't even now how he got here, but they're in Johnny's room, and either Johnny is getting fucked a lot or he sure likes putting things in his ass, because there's a gigantic bottle of lube and big box of condoms and before he knows it, Dean's figuring out how to open a guy up on the fly, because he really, really wants to nail Johnny to the mattress.

He figures it out.


By the time Sam leaves for college, Dean's pretty much half and half, sex on the job with guys and sex with women in bars. Sometimes he gets together with women from the job, but they're a lot warier and tend to be good girls, not the one-night-stand types.

Apparently he comes off as toppy, too, because no one ever complains about him being the one sticking his dick in. Most of them are salivating for it, and Dean's gaydar is pretty finely tuned. There's a whole rhythm to the stolen glances, to the nervous gestures, to the embarrassed shifts of the eyes anywhere but where they really want to look.

That's why it's so surprising when Glenn, the bartender Dean's grilling about the most recent vic, backs him up against a wall in the storeroom, his eyes never leaving Dean's.

Dean recognizes his fear response, and he takes a step back for every one of Glenn's forward, but mostly he's thinking maybe Glenn is the shifter. He's trying to figure out if there's anything silver back here, which is tough when he can only use his peripheral vision because he doesn't dare look away from the guy who, Dean realizes as his back hits the wall, probably has thirty pounds on him. He's a little taller than Dean, too, and clearly he knows how to handle himself.

Dean hadn't caught a whiff of interest, so it's a complete surprise when Glenn goes down to his knees to give Dean a blowjob. It's even more of a surprise when Glenn demands he return the favor, which has never happened in all Dean's adventures so far.

Glenn is pushy, though, getting his hands in on the act and being way more aggressive than any of the other guys Dean's been with. It's messy, too, spit everywhere, and it's the first blowjob Dean's actively disliked, even of those he's given. And if that isn't bad enough, Glenn hauls him up before he's even done. Dean would be relieved about that, but Glenn flips him around so he's facing the wall and digs around in Dean's pants, his fingers leaving bruises on Dean's ass.

"Uh, sorry, man," Dean says, not even sure why he's trying to be nice about this. He brings his arms in and uses his elbows as leverage against Glenn's groping, forcing him to take his hands off as Dean whirls back around, bracing his back against the wall. "That's a no-go."

Glenn looks ready to spit nails, and Dean is currently wondering about Glenn's IQ, because no one has ever thought they could overpower Dean before – and Glenn looks like he's planning to try.

That pisses Dean off. Sure, he's had lots of not-really-his-idea sex, pity fucks for guys and all kinds of other stuff, but no one ever forced him. No one even thought to try. The fact that Glenn thinks he can take Dean is laughable, but the fact that he might try – might have tried with other guys not as capable of handling themselves as Dean – that pisses Dean off.

"Back off," Dean says, his voice as menacing as he can make it. He's twenty-three, and long past the tenor of his teenage years, but he's nowhere near his dad's authoritative growl, and Glenn raises an eyebrow at him, almost like he thinks Dean is being cute.

Dean shifts his weight forward, forcing Glenn off-balance so he has to back up a little. Dean smiles thinly and steps around him, hoping that's the end of it. His experience with bullies is that they back off when someone shows even a little bit of fight.

Glenn is not one of those types of bullies, though, and he puts a hand on Dean's arm, squeezing hard enough to hurt. Dean uses the grip to yank Glenn down and throw him off balance, right into Dean's uppercut.

Glenn yelps and lets go, immediately shifting his weight forward and swinging wildly. Dean blocks easily and uses his right to jab, a quick hit right to the solar plexus. Glenn wheezes, too busy trying to breathe to bother with Dean anymore, and Dean gets right down in his face and says, "Next time, ask first. And no means no."


In between jobs, Dean only fucks women.

Of course he only fucks women.


He's pursuing a pretty woman one night – Amanda – chatting her up and buying her drinks, and he's just about to nudge her to go outside, ask if she wants to see his ride, when another guy comes up to the bar, and right in front of Dean's face, asks Amanda if she wants another drink.

Amanda looks at Dean, up and down once, and then turns back to new guy, up and down once, and says, "Sure, why not."

And Dean has never been scooped quite so thoroughly before, so he's willing to admit defeat. He gets off the barstool, pushing his unfinished beer toward the barback, ready to go lick his wounds back at the motel when they guy says, "And what are you having there, big boy?"

Dean freezes. He's had plenty of threesomes with two women, but this… this is something he's not 100% sure he's interested in. He can't stop looking up at the guy, and when he remembers Amanda, he glances down at her, unsure of how he feels about the amusement that's playing on her face.

He glances up at the guy again, and he looks less gay than Dean expects. He's not usually tracking guys in bars but it's not like he can turn his gaydar off, and this guy doesn't ping it, at all.

Dean decides on, "I'm fine," picking up his beer and saluting the guy with it.

The guy smiles at him, taking a step forward, sliding a hand around Amanda's waist, and putting the other on Dean's forearm. "Well, the next one's on me."

And Dean should really disengage now. The only problem is that this scares him a little, and that has always pissed him off and made him a little stupid, so he turns around, dislodging the guy's hand and putting his arm around Amanda's waist, too. "You want to wait around here that long?" he asks. "I was just thinking about heading back to my motel room."

It might be a little aggressive for Amanda, but Dean plays to win, and right now, winning means being ballsier than the guy that saw him about to get some ass and invited himself in for a threesome. Dean looks down at Amanda, smiling encouragingly, and she says, "Oh, hell yeah."

Amanda leaves her number on the dresser. He never even learns the guy's name.


It's another tweak on his gaydar, one that takes a hell of a lot of fine tuning, which means for a while, Dean gets in a lot more brawls than beds when he goes out, but when he figures it out, the subtlest of cues, not even really cues, but a conglomeration of things, posture and the way they wear their jeans and the way they scope a room, he learns how to get threesomes almost every time he goes looking for a little action.

He'll still go for the women first – two girlfriends who are inseparable and have that particular kind of smile – but if there aren't any BFFs in the bar (and really, it's pretty uncommon), he looks at the couples and finds one that'll take him home. Every once in a while, he thinks about pulling the same trick that guy pulled, stepping in just as another guy is about to seal the deal, but he hasn't quite had the right opportunity.


It isn't until Sam comes back that Dean realizes just how many dudes he's had sex with. He still doesn't think of it as anything more than convenient, a quick way to get information or evidence or sometimes just an extra person in the bed, which usually works out really well for Dean.

The thing is, guys don't hit on Sammy. Ever. It's like he's a beacon of straightness. Which is weird, mostly, but also really fucking annoying, because they get mistaken for a couple all the time and that means everybody thinks Dean's the really gay one.

Not that he's ever thought about having sex with Sam, but if he did, he certainly would be topping. Absolutely. Besides, if he was going to bottom, it would've happened already – he's twenty-six and he's had sex with lots of guys, and they all wanted his dick, not his hole. Except that asshole bartender, but Dean took care of him just fine.

Still, he tones it down. He knows he's picked up a couple of bad habits from all the flirting, so he tries to reel it in, mostly with the guys, but with the women too. It's too easy to forget himself when he has the charm at 110% and starts spewing it everywhere.

Sam's already given him a couple of looks and Dean's desperate to keep Sam on the road with him, so he tries to remember what it's like to have Sam's earnestness around to get information, instead of flirting it out of people. It's weird, how well Sam's puppy dog eyes work.

And Dean has Sam with him, so he doesn't even notice that he's not getting anywhere near as much sex as he's used to.


Hell fucks everything up.

Dean's always known, somewhere deep inside, that he is a monster, something that should be put down, something that needs to be punished. He can't even look at Sam when he tells him the things he did in Hell, and he leaves some of the most important stuff out.

Alistair rapes him only once. Oh, he's a sweet talker, but after the first time, he says he'll only fuck Dean if Dean asks him to. And as much as Dean craves the respite from the torture, he won't let himself ask. That much, he can hold on to.

When he's the torturer, though, rape is the sweet spot. Psychological torture is much more effective than physical, and Dean knows how to make his subjects lust for things that twist their psyches into knots. He knows how to give them something that's just to the left of what they want, and make them beg for more.

He throws up for hours on the side of the road the first time those memories come back to him.


Something about Castiel speaks to Dean. There's something powerful about him; righteous. He feels like Castiel could burn the monster right out of him, and one night when he's way too drunk for the occasion, he asks Cas. He asks Cas to fuck him, to punish him, to maybe give him some respite from the damn guilt he carries around like a dead body.

He doesn't remember anything after that. He's not sure if the whiskey got the better of him or if Cas put him to sleep, but he wakes up with his ass intact and Cas never mentions it, so he assumes the answer is no.


His libido drops and drops as the apocalypse nears, and he almost forgets about sex entirely. He doesn't have any room for it. His whole life is filled with Sam and the end of the world, and there is nothing outside of that.


When Sam makes him promise to go to Lisa, he wonders what the hell he's supposed to do with her.

It's scary, though, how quickly he falls back into take-care-of-Sammy mode, except with Ben. Having someone depend on him like that narrows his focus, lets him concentrate on what needs to get done to take care of Ben. Lisa, too, though she needs a different kind of care.

A few months in, after things have settled a little, Dean's nightmares about Hell come back. He searches them for intent, for a message from Sam, anything, but they don't seem to hold any particular meaning. It's just him, raping person after person on the rack, and suddenly he is completely and utterly impotent.

Sex with Lisa had been fine; good sometimes, expedient sometimes, luxurious sometimes. Since the nightmares, he still takes care of her – he knows more ways to get a woman off with his mouth than other guys know with their whole bodies – but he curls up behind her on the bed after, not willing to talk about it. He knows she's worried, but there's nothing to be done about it and Dean is never sharing his time in Hell with another living soul. It's one of his failures that he shared it with Sam. He won't do that to another person.


Dean doesn't think about sex again until Purgatory. He has a few opportunities, tries too hard for Sammy's sake (he knows Sam equates Dean getting laid with things being normal, and Dean does his best to oblige, though his heart's not in it). But Purgatory.

Purgatory is surprisingly aptly named. It purges most of the crap, brings Dean down to his basest instincts, which, since Sammy is safe and sound in the mortal dimension, are: find Cas and kill everything that gets in his way.

Benny… Benny is everything Dean needs. He's someone who's in it for himself, but who knows what Dean is worth, so he's got Dean's back. He can't afford to let Dean lie to himself, so he calls Dean on all his bullshit. He expects the same, but Benny never bullshits Dean, so Dean never has to call him on it.

They spend months in the wilds of Purgatory tracking Cas. They get close a few times, but not close enough for Dean to actually get a glimpse.

Nights after a just-miss Cas sighting, Dean shakes with frustration. He has to find Cas and he's failed again, and he just needs to let it all out. The first time, he punches Benny when he gets too close, asks too many questions. Benny punches him back and it's so reminiscent of the way he and Sam used to spar their annoyances out in middle school that it gives him exactly the release he needs.

As his frustration with his inability to find Cas builds, though, fighting doesn't always work. Dean's not even sure how Benny knows, but one minute, Benny's holding him against a tree by his throat, and the next he's fucking Dean hard enough to get tree-burn on his ass.

The relief is intense; the release of guilt is better than the orgasm, and if Dean's got punishment and sex mixed up in his head, well. He supposes that's to be expected with the life he leads. Benny never comments, never gentles him after. But he does watch over Dean when he sleeps, sitting down close, somehow mimicking the feeling of having Sam in the bed next to him, and that's when Dean knows that Benny's not completely in it for himself.


When Cas puts his arms around Dean after Dean tries to put a hammer through his brother's head, Dean's out of his mind. Even under the Mark, and the demon, and every fucked up thing that's going on in his head, there's something breathlessly exciting about the way Cas handles him so easily, like he's a doll, some girl's plaything.

He asks Cas again, that night, runs after him in the hall when he can't stand to stare at the four walls of his room after Cas closes him in. "Please," he says, because the guilt is about to choke him and this is the only thing he knows for sure that helps.

He doesn't have to say anything else, not even what he wants, which just goes to show Cas remembers the last time Dean asked him for this.

Cas tilts his head and stares at Dean for a long moment, and then says, "Yes."

Hope floods Dean's chest at the single word, followed immediately by trepidation that Cas won't be hard enough on him, that he'll pussyfoot around and Dean won't get what he needs out of it after all.

Cas tilts his head again and walks calmly toward Dean, staring into his eyes the whole time. Dean can hold Cas's eyes now, even graced-up Cas, which says a lot about both of them.

The trench coat Cas is wearing gets thrown carelessly inside the door of Dean's room. Cas stands right in front of Dean and pulls his shirttails out of his pants, unbuckling and removing his belt, which gets tossed down on top of the trench coat.

Dean's starting to get nervous; this is the opposite of what he needs, and he thought Cas understood – this isn't about sex or love or even the bonds of brotherhood, this…

Cas puts his hands on Dean's shoulders and shoves him back into his bedroom. With the bonus angel strength, it's enough to lay him out flat on his bed, his legs dangling off the end. Dean lets out his breath, closing his eyes and letting his head fall back on the bed. Cas does get it.

It's proved twice over when Cas uses his angel powers to hold Dean down on the bed, roughly yanking his jeans down. He must do some angel magic to get the rest of Dean's clothes off though, because suddenly he's naked and he doesn't really remember moving enough to accommodate that.

Cas lifts Dean's legs onto the bed, knees up, and crawls between them, shoving Dean up the bed and shouldering his legs open wide enough that the hamstring stretch burns.

The little pains are good, they ramp him up for the bigger ones he knows are coming; he waits for Cas to push his way in, the stretching and tearing.

Dean doesn't have any real-world experience with getting fucked; he's fairly sure the rules are a little different in Hell and Purgatory. He knows that if Alistair had fucked his physical body, he would have died. He remembers tearing, blood, Alistair walking away without touching another instrument of torture, and despite that, Dean passed out after, probably from perceived blood loss.

Benny was only slightly less rough; Dean never tore, but it wasn't like Benny spent forever getting him ready; he just did something down there and pushed in a second later. Dean hurt after but he never bled, so whatever it was, it wasn't permanent damage.

Cas, though. Cas is slowly opening him, inch by inch, with lube and fingers, and at one point tongue. Dean panics, choking on the shame he's feeling because this isn't want he wanted, it's not what he needed, and it's way more than he deserves.

"I'm not doing this to punish you, Dean," Cas says, way too matter-of-factly. Dean's beginning to think this was a huge mistake, he should never have asked Cas for this. "I am doing this because I love you."

Dean can feel the shame and self-loathing bubble up and he doesn't know what the hell he did to deserve having people in his life who love him; not like this. "Cas, stop," Dean says, because he can't – he absolutely cannot - take this, he will die if Cas makes him.

"You will not die," Cas says. "And you wanted me to take you against your will, so I am only doing as you requested."

"Cas," Dean says again, because something else is building in him, something hopeful that breaks through Dean's defenses, making him feel like he can maybe still do some good in this world and take some pleasure in it, too.

He's never been fucked like this, gently and with care, and, he's pretty sure, Cas doing some weird angel thing to his prostate because his body feels really, really good. Tingly. And Cas is still whispering, "I love you" into his skin, pressing open-mouthed kisses onto his shoulders and neck as he slowly rocks into Dean.

The release starts long before his orgasm. Dean can feel his shame lifting, the guilt and self-hatred ebbing away as he arches his back to meet Cas. The litany of Cas's declarations hasn't stopped, he just keeps telling Dean how much he is loved until it takes over everything, whiting Dean out in what feels a little like a display of grace; if he's still alive after, he hopes he remembers to ask Cas about it.


It doesn't fix everything, but it helps for a little while, at least. Dean can accept Sam taking care of him for once; he can stave off the Mark with thoughts of Cas taking him apart on his bed.

He's doing remarkably well, all in all, and when the deputy in Hibbing pings his gaydar, something that hasn't happened in years, he slips into his role like he's eight years younger and still fucking his way through the lower forty-eight. The deputy bites, looking away coyly, taking the bait with a small smile.

Oh yeah, Dean's still got it.