Work Header

Dean Winchester Is a Gay Virgin

Chapter Text

Dean Winchester has a grand total of two big secrets:

Secret #1 is that he’s a virgin.

Secret #2 is that he’s gay.

The latter, he feels, is the cause of the former. He’s not what one would call “out” about his sexuality, having an overbearing father who Dean is fairly certain would disown him if he ever found out.

And Dean is quite partial to having both food and shelter.

Dean is a virgin because he’s kept himself off the market purposefully, so as not to take a chance at anyone finding out and ruining both his reputation as the town’s star pitcher (no pun intended), and risking his baseball scholarship.

Sam thinks Dean might be paranoid about that last part, that no one would take away Dean’s scholarship just because he digs dudes, but Dean also has an image to uphold. It’s a heavy burden to bear, but Dean has dreams, and he knows the darkness of this world far too much to trust that it will accept him with open arms for exactly who he is.

Dean’s little brother Sammy is the only other person who knows. He probably knows the first secret too, the kid being MENSA-level smart, and having never seen Dean express any genuine romantic interest in anyone, ever.

When Sam found out, he was 13 years old and Dean was 17. Dean came home from school to find Sam kneeling at the foot of Dean’s bed, rifling through a shoebox of gay porn mags.

Dean thought he was going to die right then and there, that his cover was blown, that this was the end. Their dad would kick him out of the house and he would be thrown to the wolves. Dean trusted that Sammy could keep a secret about as well as his father could keep a bottle of booze in the house without drinking it in a single evening. That is to say, not at all.

“Sam,” Dean had said, eyes wide and heart pounding in his chest, dropping his book bag to the ground. “What the fuck are you doing?”

Bless Sam Winchester, he didn’t look shocked, or disappointed, or even confused. He just looked at Dean and asked, “So you don’t have any girl porn?”

Dean could have cried with relief, but even he wasn’t that gay.

Four years later, Dean is a psych major at Wright State University in Dayton, Ohio. Both he and his father work full time at Bobby’s auto shop downtown, so with both school and baseball thrown in the mix, Dean doesn’t have time for dating anyway. Or friends. Or fun. Or even sleep, some days.

Dean finishes up at the shop early today, so he heads to class early—Behavioral Neuroscience—and is stoked that he has a few minutes to shovel a piece of pizza down his throat so that he doesn’t have to suffer through two hours of the history of prefrontal lobotomies on an empty stomach.

On his way into the cafeteria, he sees a group of colorfully-dressed individuals standing outside of the building.

One of them, a guy in a bright blue Hawaiian shirt and a plastic lei, cuts in front of Dean as he reaches for the door and shoves a flyer in Dean’s face. “We’re having a luau!” he exclaims in a voice that is completely contradictory to his attire: it’s deep, gravelly, and far too serious to be excitedly telling Dean about a luau.

Dean crosses his eyes to look at the flyer. It’s as colorful as the gaggle of people behind the man who is standing a bit too close in Dean’s personal space. Dean grabs the piece of paper from the man’s hand and looks at him.

The guy takes off his 80s style Raybans and has eyes that are impossibly bright blue, brighter even than his shirt, which could hail airplanes from the sky.

Dean looks down at the flyer. It reads:


Next Friday! 7PM!! The Student Union Atrium!!!


“Sorry, man, not my thing,” Dean tells him, and hands the flyer back to Blue Eyes, opening the door to the cafeteria.

The dude follows him. “I’m Castiel,” he says, trying to keep up with Dean. “But everyone calls me Cas.”

Dean doesn’t look back at him. He walks faster, and Cas walks faster too. “Cool,” Dean mumbles. He’s painfully hungry and painfully attracted to Blue Eyes, a combination that always leaves him painfully grumptastic.

“I’m head of the LGBTQA Alliance,” Cas adds.

“Cool,” Dean says again.

“What’s your name?”

They round the corner to the cafeteria and Dean grabs a slice of pepperoni pizza from under the heat lamp of the pizza place. “Dean,” he replies, gruff.

Dean walks across to the other side of the cafeteria and grabs a Red Bull from the cooler, slamming the door shut and heading to the cashier.

Cas is still following him. “I think you should come to the luau.”

“Can’t.” Dean sets his food down to take out his wallet from the back pocket of his jeans.

 “Why not?” Cas asks.

“Work,” Dean replies as he hands the cashier a ten and gets his change.

“What do you do?”

Dean leaves the cafeteria and walks down the hallway toward his class. “I fix cars.”

“You’ll be fixing cars on a Friday night?”

Dean turns on his heel to glare at Cas, and Cas almost runs into him. Unlike every other person on the planet, he doesn’t step out of Dean’s personal space, he just lets Dean stare him down, cross-eyed and silent.

To be fair, Dean realizes, he hasn’t stepped out of Cas’s personal space either.

But Cas started it.

“I’m not gay,” Dean tells him, a bit too stern of a response to a question that wasn’t even asked.

Cas’s lips turn up slightly.

“I’m not,” Dean reiterates.

Without breaking eye contact, Cas holds up his horrifically colorful flyer. “The ‘A’ in LGBTQA stands for ‘ally.’ As in straight ally. I wasn’t trying to imply that you’re gay, Dean.”

Dean’s face softens and he blinks, “Oh.”

Cas shoves the flyer in his hand. “I think you should consider attending,” is all he says before turning away from Dean and walking back toward the cafeteria.

Dean has no idea what just happened, but he knows he just broke closet rule numero uno: don’t get super defensive about your sexuality when it was never in question in the first place.

He shakes his head at himself and takes a seat in class to choke down both his pizza and humiliation.


Dean can’t get Castiel’s alarming blue eyes out of his head. He sees them when he jerks off, he sees them behind his eyelids before he falls asleep, he sees them in the back of his mind when he’s at the batting cages or when he has his arms elbow-deep in an engine.

By Friday night, Dean realizes that he is totally fucked.

No one has ever had an effect on him like this before, except for maybe Balthazar in high school, the dreamy star quarterback a grade ahead of him who served as Dean’s ultimate spank bank fodder for many years.

The result of this infatuation with Balthazar is why Dean adamantly avoids using the word “crush.”

And even if he did, he would never admit to having a crush on the Hawaiian-shirt-wearing, sex-haired, blue-eyed, pink-lipped, deep-voiced, stubborn mule who serves as the head of the LGBTQA Alliance at WSU.

So when Dean checks the clock a quarter after 7, snaps his Ramachandran book shut, throws on his shoes and leather jacket, and heads to campus, it’s because he wants to support diversity, and not because he wants to see Castiel again.


Dean arrives at the luau at a time he considers to be fashionably late. He’s wearing a white v-neck t-shirt, his dad’s trusty old leather jacket, jeans that may or may not be a little tight around his ass, and his work boots.

He appreciates that he defies the gay stereotype by only owning three pairs of shoes: his work boots, his running shoes, and his baseball cleats. To him, that’s all anyone really needs anyway. Other than the secret partition of his hard drive that has a quantum fuckton of porn on it, Dean Winchester is a minimalist.

He enters the Student Union to find a surprisingly large gathering of people wearing all manner of bright Hawaiian garb.

Dean also defies the college student stereotype by being able to count the number of college parties he’s been to on one hand, living off campus, and working full time.

This might explain why Dean stands awkwardly at the punchbowl, filled with bright red liquid and floating pineapple rings, staring at it as though it will tell him how to interact with other human beings.

Even with his baseball team, Dean is a bit of an outsider, keeping his nose in a textbook between innings, and ducking out before pizza parties and barhopping. His team likes him, he thinks, but they don’t get him. No one does, except for Sammy, and, like his three pairs of shoes, that’s all anyone really needs anyway.

Someone bumps into Dean, nudging him with an elbow. “Hello, Dean.”

Dean looks up to see Castiel, wearing an outfit Dean has trouble comprehending in full: flip-flop sandals, a grass hula skirt, and no shirt. Around his neck is the same plastic lei he was wearing when Dean met him, and atop his head is a crown of flowers.

The motherfucker has a chest and shoulders that look like they were chiseled by God Himself.

Dean swallows.

Eyes wide, he forces his gaze up to meet the obnoxious beacons of blue light that have served as Dean’s ultra-porn for the past week.

And now the dude is right in front of him. Shirtless.

Dean is so fucked.

“Hey,” he replies meekly, with a small smile.

Cas grins at him, all teeth and gums and dimples and mirth, and it’s abso-fucking-lutely adorable. But Dean refuses to admit that to himself. “You came!”

A truly awful choice of words, Dean thinks.

“Yeah,” is all Dean can manage, scratching the back of his neck and looking everywhere he can except at Castiel, willing his face to turn down the temperature of the flames erupting on his face.

“Let me introduce you to everyone!” Cas exclaims.

He takes Dean by the shoulder, turning him around to face the room full of people. Cas’s hand feels like it’s burning a brand into him, and Dean’s poor heart hammers in his chest so loud, he thinks Cas can probably hear it.


Everyone, literally every single person, all two or three dozen of them, turn to Dean and say simultaneously, “HI DEAN!”

Dean knows that when he pitches, there are hundreds, sometimes thousands of eyes trained on him.

But that’s different. All those people are looking at Baseball Dean, the man’s man with an arm like a rifle. They’re all looking onto a façade, an illusion Dean creates of himself. Now, a whole bunch of people are looking at Dean, and Dean doesn’t have an illusion to throw at them. He’s suddenly terrified that they can see right through him, see his disgustingly shameful porn collection, see his infatuation with Balthazar, see the fear he has of his father, see his budding—goddammit—crush on Castiel, the grass-skirted motherfucker still burning a handprint onto his shoulder.

Dean gulps. “Hey,” he says in the exact same way he greeted Castiel. He turns to Cas as the large group of people continue mingling and drinking punch. “Is this a cult?”

Cas’s smile drops and he replies, completely serious, “Yes.” He nods, solemn, his hand still on Dean’s goddamn shoulder. “We are the Cult of the Gay, and we’re here to take your soul and drown it in glitter and the tears of our closeted forefathers.”

Something snaps in Dean and his heart lifts a little in his chest, along with the corners of his lips. He laughs, and matches Cas’s goofy smile, relaxing into Castiel’s grasp, which is now bordering on awkward. But Dean doesn’t care. He feels a kind of electricity around Cas that he can’t quite put a finger on, and he doesn’t think he minds if Castiel never stops touching him.

Cas, still smiling, looks at his hand still clutching Dean’s arm like he forgot it was there. He squeezes his hand around Dean’s bicep and his eyes go wide. “That is…” he swallows. “Quite an arm you have there.”

Dean smiles crookedly at him. It’s Cas’s turn to blush.

“I’m a pitcher,” Dean tells him.

Cas’s eyes shoot up to Dean’s, wide.

“Baseball, dude. I’m a baseball pitcher.”

Cas looks both relieved and disappointed. “Ah.” He finally removes his hand from Dean’s arm and turns toward the punchbowl, filling up a small glass. “So you’re here on a scholarship I take it?”

“Yep,” Dean replies. He really sucks at small talk. And big talk. And all forms of communication in general.

Thankfully, Castiel seems to be an expert in the art of conversation, asking smoothly, “What’s your major?”

“Psych,” Dean shrugs, as though he needs an excuse to enjoy being educated in the science of the mind. “Yours?”

Cas hands him a cup of punch and Dean takes it, their fingers brushing, which sends a tiny shiver up Dean’s spine. “Gender studies, but I’m doing pre-med. What year are you in?”

Dean takes a sip of his punch. “Junior.”

“Hey me too! Are you from around here?”

Dean shakes his head. “Well, kind of. I grew up in Dallas, but my dad moved here to find work when I was a kid. You?”

“I grew up in Russia,” Cas replies with a frown, looking at his feet, but then he immediately perks back up into himself, all bubbles and smiles and flamboyance. “I’m here for school.”

Dean huffs a laugh. “Where’s your accent? And why the fuck would anyone voluntarily choose Dayton?”

Cas replies in a Russian accent, “I learned not to use it because I got tired of being asked why I chose Dayton.”

Dean’s dick twitches in his pants. He had no idea he had a Russian kink. Or maybe he just has a Cas’s-voice kink. The result of both this thought and realizing he asked a question he shouldn’t have makes him blush. “Sorry,” he says, staring down at his feet.

Cas smiles at him, warm, and switches back to his American accent. “It’s okay. I’m happy to tell you about it, but most of the buffoons at this school are all, ‘Har har, a foreigner! Let me ask a million dumb questions because I’ll never risk leaving this country once in my entire life!’”

Dean shrugs. “I haven’t been out of the country.”

Cas eyes him. “If you could go anywhere in the world, where would you go?”

Dean blurts out the first thing that pops into his head, Secret #14,278: “I kinda want to join the Peace Corps when I graduate.” He has never said that out loud before, and he feels like an idiot for doing so. He knows he wouldn’t last one day in rural Africa or Asia, let alone two damn years.

Cas grins. “And here I thought I had you pegged, Dean…”

Again, a truly awful choice of words.

The end of Cas’s statement turns it into a question, which is a sly attempt at asking for Dean’s last name. “Winchester,” Dean supplies.

Cas holds out his hand for Dean to shake. “I’m Castiel Krushnic. It’s really, really nice to meet you, Dean Winchester.” Then he mumbles something in Russian that Dean can’t understand.

Dean looks at him quizzically before replying, “It’s good meeting you too, Cas.”


Dean is unused to the concept of “fun,” so when he realizes he’s having it, it hits him like a baseball to the ribcage.

He’s been at the luau now for a couple hours. Cas introduced him to most of the people there, and now they’re sitting on the balcony of the Student Union, drinking punch and eating now-cold Hawaiian pizza.

Dean is next to Castiel, probably a few inches closer to one another than they have to be given the size of the couch they’re on, and across from them are Cas’s friends, Charlie and some dick named Dick.

Dean really digs Charlie. She’s funny and smart and Dean kind of just clicks with her. He finds out that she’s a computer science major with a minor in gender studies. Dick, however, is the ultimate douchebag and Dean can sense some tension between he and Cas as the evening wears on. Dick is a business major, predictably enough, given the fact that on a Friday night, the dude is still wearing a suit and tie. To a goddamn luau.

When the conversation dies down, Charlie stands and says, “Well I gotta head back to my dorm. It was good meeting you, Dean! I hope you come to more of our events.”

Dick looks from Cas to Dean in what Dean can only assume is a possessive fury over Castiel. Charlie grabs him by the shirtsleeve and tells him, “Come on, Dick, I think it’s time for you to go too.”

He stands and sneers down at Dean with a sickly sweet false smile. “Good meeting you, Dean.”

Dean smiles up at him warmly. “You too… Dick.”

Dean sneaks a sidelong glance over to Castiel, who is looking down and fumbling with his glass of punch, which matches the shade of his face.

Dick leans down, lifts Cas’s chin, and kisses him on the cheek, saying quietly, “Goodnight, babe. See you later tonight?”

Cas, not meeting his gaze, still turning around his now-empty glass in his hands, gives him a small nod.

Dean gets all manner of uncomfortable knots in his stomach. His hair stands on end. Something is just wrong about the way Dick looks at Cas. Like Cas is a thing, a possession. He can’t tell what expression his face is making, but he hopes it’s blank, apathetic. As far as anyone here knows, he’s straight, so he shouldn’t be affected by such a scene. Nevertheless, Dean feels his stomach sink, as much as he doesn’t want to admit that he had gotten his hopes up about Castiel.

Off the market, he reminds himself. It’s for the best.

Charlie smiles apologetically to Dean and drags Dick away from them.

Cas clears his throat, leaning forward, and opens his mouth to speak, but closes it again, not saying anything.

“So…” Dean begins. He swears to God that he physically cannot stop himself from asking the question that comes out of his mouth. “You and Dick are a… thing?”

Cas sighs, and still won’t look up. “It’s… complicated.”

Dean huffs a laugh. “Is that what your Facebook status says about him too?”

Glaring, Cas finally looks at Dean, and asks, “Why do you care?”

Dean suddenly realizes that maybe he showed a few too many of his cards, so he looks down at his hands and shrugs. “Not my business. Just that the dude seems kind of like a, you know… dick.”

Cas shrugs too. “He’s not, though. He treats me well enough. I just… didn’t think this through is all. It’s my fault. I’ll tell him you’re straight and then he’ll be fine. It’ll all be fine. Everything’s okay. Everything’s okay…” he trails off, and Dean realizes that Cas is speaking more to himself than to Dean.

Dean blinks at him, confused, and sees that Cas is shaking.

Suddenly, Dean puts two and two together and his heart catches in his throat. He’s seen that exact tremble before in someone else, a long, long time ago: his mother. And he thinks he knows exactly what it means. “Cas?”

Cas doesn’t answer, so Dean reaches over to touch his shoulder, asking, “Dick… he doesn’t... you know…?” Dean can’t figure out how to finish the question with anything other than “hit you” so he trails off.

Cas takes a deep breath, straightens his posture and grins at Dean. “So you’re a mechanic? What kind of car do you drive?”

Dean lets his hand drop from Cas’s shoulder. He doesn’t know how to handle these situations, and since he barely knows Cas, he doesn’t think it’s appropriate to butt into his life when he only even has an inkling as to what’s going on. It’s obvious Cas doesn’t want to talk about it, so, like Cas, Dean plasters on a grin and replies, “I drive a 1967 Chevy Impala. She’s my baby. I fixed her up from just a heap of scrap.”

Their conversation continues on, well into the night, lighthearted and easy. Unlike Dean, who is capable of conversing on a total of three topics—baseball, cars, and psych—Cas appears fluent in everything. He knows just enough about cars and baseball that they can have engaging conversations about them. He seems genuinely thrilled when Dean talks passionately about the things he’s into, and asks questions, always wanting to know more, to get additional details. His mind is like a sponge of information, and Dean is happy to have someone to talk to about his hobbies that everyone else finds incredibly dull. When Dean talks to most people, they always change the topic back to themselves, but Cas stays trained on Dean, enrapt in him.

Dean asks Cas about his life in Russia, which is another topic Cas skirts, giving only a minor amount of detail and changing the topic to school, and then back to Dean.

Slowly, the conversation dies down and Cas looks around. They’re the only people left in the building. The luau decorations have all been cleaned up, and the only lights left on are the emergency ones.

“When did that happen?” Cas asks, nodding to the lights and the empty building.

Dean checks his watch. “Shit, it’s 2AM. I gotta go. Got practice at 8.” He stands to leave, and Cas looks up at him, eyes filled with wariness.

“Do you live on campus?” Cas asks.

Dean scratches the back of his neck. “No, I live with my dad and brother downtown by the shop.”

Cas stands too and smiles. “So, um… no homo, but can I have your number?”

Dean grins at him, and holds out his hand for Cas to give him his cell phone. Cas goes for his back pocket, realizes he’s still wearing a grass skirt, and reaches under the waistband to pull his phone out of an invisible, slightly suspicious pocket, then hands it to Dean.

Dean chuckles and unlocks Cas’s phone to find that Cas has 12 texts from Dick and 5 missed phone calls. His smile fades, and he goes to the contacts and adds his number, not saying a word to Cas about Dick.

Dean hands his phone back to Cas, saying, “Text me sometime. I want to come the next LBQTGMSTVRXQLP event that you have.”

Cas laughs, and corrects, “It’s LGBTQA.”

“Sorry, I’m kind of dumb about this stuff. What does that stand for?” Dean asks.

“Lesbian, gay, bi, trans, queer or questioning, and ally or asexual.”

Dean shuffles his feet and looks down. “Sorry if this is too personal a question, but which one of those are you?”

Cas gives him his gummy grin. “I’m gay, Dean.”

Dean tries to push down the little flutter that his heart makes, and the small flare of envy at Cas’s ability to so easily say those words aloud. “Cool,” he nods. “Well if you want to hang out sometime, let me know. We can go for coffee or whatever and you can teach me more about LGB… TQ… A… stuff,” Dean recites slowly.

“Sure,” Cas replies. “I’ll text you.”

Dean realizes that they’re standing a bit closer together than bros normally stand, and he steps away, toward the door, reluctant to leave.

“Cool.” Dean takes another step backward. “Yeah.” Another step. He bumps into a side table, looks down, and steps around it. “See you later, Cas.”

“See you later, Dean,” Cas replies, gummy grin still on his face.

Finally Dean turns away and heads to his car to go home, dizzy with his newfound adoration of Castiel Krushnic.