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Sex 101, or: That Time Castiel Asked Dean to Teach Him How to Have Sex

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“I want to have sex,” Castiel announces suddenly.

Dean chokes on his gulp of Baja Blast. “What? Like right now?”

They’re both in the Impala, waiting for Sam to pick up his rabbit food take-out. Dean and Castiel had obviously opted for Taco Bell.

Castiel looks over at Dean like he’s a moron. “No, I mean… sometime. It’s something I’m interested in doing as a human.”

Dean figuratively chews on that a moment while literally chewing on his straw. He doesn’t quite know how to phrase his reply. “So… like… with a chick? Or a dude?”

Castiel returns to staring out the windshield of the Impala. “Does it matter?” 

“Uhh, I mean, kinda. I guess not. I dunno,” he replies noncommittally while rubbing the back of his neck. 

It is a very rare sight that Castiel takes down his dysthymic tax accountant mask. He looks down at his hands, and Dean can swear he sees him blush. “I guess I don’t know yet.”

Putting the pieces together, a mischievous grin spreads across Dean's face. “Well there’s only one way to find out.”


Four hours later, Dean and Cas are in the parking lot of a bar in some suburb in bumfuck nowhere, Ohio.

“You ready for this?” Dean asks, a little more excited at the prospect of hooking up his ex-angel friend than he should be. He’s not worried about a repeat of the last time he attempted this endeavor because Cas has since lost his psychic mojo.

Cas looks ten times more apprehensive than he did when admitting he didn’t know if he liked chicks or dudes. His eyes are wide and he’s trembling, staring off into space while not seeing anything at all. “I… no. No I’m not. Let’s forget I ever said anything. I can’t do this.”

“Sure you can! Look, we’ll go in there, grab a couple beers, watch the game, scout for chicks, chat ‘em up, and then you can take one back to the room and seal the deal.”

Castiel looks to Dean now, icy blue eyes blazing under the street lights of the parking lot, more anxious than Dean has ever seen him (which is saying something, given their history of almost getting killed on a weekly basis). “But isn’t that... wrong?” he asks, with more curiosity than condescension. “Convincing a person that you like them, only to use their body for your own personal fulfillment?”

“Whoa, buddy," Dean replies, holding up his hands. "Couple things. One: we’re not convincing anyone we like them. We’re convincing them we want them. Two: sure, you’ll get your own personal fulfillment, but you gotta give a little too, you know what I’m saying?”

Castiel evidently does not know what he is saying. He stares at Dean blankly.

“Okay,” Dean pinches the bridge of his nose with his fingers, acknowledging that the night ahead of him is going to be a long one. “Maybe we jumped into this too quickly–”

“Can I just watch?”

If Dean had been drinking a Baha Blast, he would have choked on it again. But he does not have a Baha Blast, so instead, he blinks at Cas in rapid succession. “...What?”

“Watch,” Cas replies, flat.

A silence settles over them so thick that Dean hears crickets in the distance. His mind blanks temporarily, and then he asks, his voice an octave higher than normal, “You mean me? And a chick? Go at it?”

“Yes,” Castiel replies, all semblance of previous hesitation gone. “So I can learn how to properly fornicate.”

Dean sighs. “Okay dude, lesson one: no using the word ‘fornicate.’ And secondly, that’s what porn is for!”

Cas again looks at Dean like he’s an idiot. “I know that pornography is staged. It’s… fake. And I’m not interested in the experience that pornagraphic sex will afford me. I’m interested in… real sex. So I want to see real sex.”

Dean sighs again and paces across the span of the parking spot they’re standing in, pushing back the waves of sordid memories he'd rather not recount at the moment. “Man, this is weird. I dunno man.”

Cas remains silent.

Dean continues pacing, then spins around toward Cas and points at him. “Okay, here’s how this is gonna go. You follow my lead. Don’t say a word. Pretend you’re invisible. Keep your dick in your pants the whole night. I choose the chick. You have no voice and no vote in this, understood?”

A corner of Cas's lips twitch up, and he begins his night of silence at that moment by supplying a curt nod.

Dean about-faces with a huff and marches into the bar.


At the bar, Dean orders the both of them beers and shots of whiskey. He needs to be loosened up for whatever the hell is going to happen tonight. The chances they’re even going to find a chick in suburbia who will let a dude watch them fuck is close to zero. Dean considers his options, scouting the bar for hot tipsy chicks who look like they’re out to get laid. Luckily, it’s a Friday night and the place is hopping. Dean looks over to Castiel, who is nursing his beer and staring at nothing in particular. The only sign of Castiel’s anxiety, Dean notices, is the way his sharp, stubbly jawline is clenched shut. Dean admits that their ratio of attractiveness is what makes this idea even remotely plausible: Dean is a leather-coat-wearing, sly-talking, badass sex god; and Castiel is a deliciously-shy, blue-eyed, bedheaded hottie.

Dean decides not to order another drink, because he realizes he just referred to Cas in his head as a bedheaded hottie.

But it’s a totally objective observation, he adds.

Across the bar, Dean spots a woman spotting him. The chair across from her is empty, so Dean catches Castiel’s eye and hunter-signs to him that he’s going to check out the brunette in the corner. Cas nods.

Dean grabs his beer and meanders over to the woman, who immediately blushes and looks away from him. “Whatcha drinking?” he asks her casually.

She smiles at him, shy and sheepish, but before she can reply, she looks over Dean’s shoulder and her eyes widen. Dean turns to see a dude who is admittedly bigger than him looking very angry, and throws his hands up in an apologetic gesture, swipes his beer off the table, and walks quickly back to the bar.

He doesn’t say a word to Cas, but he can see the bastard smirking again.

A half hour passes. Dean has his eye on a woman who is at the bar seemingly alone. She keeps checking the clock on her cell phone and sighing, nursing a beer while looking bored and dejected.


Dean elbows Cas and nods his head in the redhead’s direction. Cas nods, and Dean slides over the three barstools between them to sit next to her.

“I don’t mean to pry,” he begins, “but you kinda look like you just got stood up.”

She looks at him, at first appearing genuinely irritated, but then her expression softens. “I guess I did. I just didn’t want to admit it to myself until now.”

“Hey, that sucks,” he replies, tone softening. After a brief pause, he grins. “But it looks like your beer is almost empty, so how about I order you another one and we can work on improving your night.”

She smiles at him. “I’d like that.”

Dean orders both of them beers and shots and whatever else the woman asks for, and they chat for an hour and a half.

Her name is Cheryl and she’s a paralegal in town. She was supposed to meet a guy she’d been talking to on the Internet for a couple weeks but he was a no show. Now she’s tipsy, and her cheeks are a little pink, and she’s telling Dean a story about how she got invited to do amateur hour at a strip club on Bourbon Street, which amuses Dean more than he can admit to her. They’re sitting close together so that their knees are touching. Dean can smell her perfume; the music is so loud that she has to speak right in his ear, while periodically grazing it with her lips, and it’s driving Dean crazy.

Dean thinks she’s pretty cool. And really hot, with a va-va-va-voom kind of curvy body, and lips equally as plush. She also seems like she has her shit together, so Dean doesn’t want to bullshit her. He realizes now is as good a time as any to bring up his proposition.

“So speaking of amateur hour,” he says, sipping his beer. “See that guy over there?” He nods in Castiel’s direction.

She looks momentarily apprehensive upon looking at Castiel, but Dean leans into her and takes his turn grazing her ear with his lips, feeling her tremble faintly beside him.

“Do you... want to come home with us?” Dean rumbles in her ear.

Her eyes widen, she leans back, and stammers, “I… uhh, I’ve never… I can’t…” and looks down at her hands.

Dean quickly fills in the details. “He won’t be involved. He just wants to watch. That’s what he’s into. It would be all you and me, babe.” He takes her hesitation to dip his lips to her neck and press one kiss gently below her ear. Pulling away, he looks at her and gives her The Smoulder, looking from her eyes to her lips and back up again.

Her eyes are wide, her cheeks are flushed, and she’s breathing heavily. After staring at Dean for a few tense moments, she comes to a decision and nods. “Yeah. Yeah okay.” She knocks back the rest of her beer and stands. “Let’s do this.”

Dean gives her the name and room number of the motel they’re staying at and tells her they’ll meet her there in twenty. He pays the tab, and grabs Cas by the elbow to drag them out of there.


There’s a soft knock on the motel room door. Dean has Cas situated in a chair in a dark corner of the room, after making him take off his suit jacket and roll up the sleeves of his dress shirt to look slightly less creepy. Dean and Cas haven't exchanged any verbal words since their discussion in the parking lot, which made the drive home from the bar terrifically awkward and tense.

Dean opens the door to find Cheryl, still clad in her tight-fitting, bright red dress, with her ample chest perfectly accentuated.

He smiles at her, and she smiles back, looking less nervous and more excited than she had at the bar. Dean, never one for words where actions are better suited, pulls her into the room, shuts the door, and kisses her, slow and deep.

Her lip gloss tastes like cherries and her mouth is small and perfect. Dean explores her lips with his tongue and teeth, gently nibbling her bottom lip until he has her gasping and moaning lightly. He rubs his hands all over her back and hips and ass while she keeps her fingers tangled in his hair. After moving slowly down her neck with kisses, he pulls away, taking her by the hand and leading her over to the bed.

He pulls the zipper down on her dress, and she steps out of it, revealing a matching set of lacy black underwear. She keeps her heels on.

Dean affirms that this chick is really cool.

He takes off his shirt while she unbuckles and unzips his pants, dragging her nails around his hips and admiring him. Dean steps out of his jeans and lowers her onto the bed in such a way as to give Cas the best view.

Dean tries to avoid looking at Cas, who is sitting not four feet away from them, staring with interest at the proceedings in front of him, as though examining an interesting science project.

Dean also tries to avoid thinking of Castiel’s blue eyes while staring into Cheryl’s grey ones. He reaches around her back and unhooks her bra, pulling it off to reveal a perfect, perky set of Ds. Leaning forward, he gently trails kisses from her lips to her neck to her chest until he has his lips wrapped around one nipple while his hand fondles the other.

The small moans and gasps Cheryl makes are igniting the fire in Dean, who trails his hand down her body and between her legs. He softly runs his fingers up and down her panties, barely grazing her clit, until she spreads her legs and pants, “Oh Dean, oh Dean please…”

Dean moves back up her body and kisses her again, sliding her panties to the side to dip his fingers in her. She’s soaked, and he runs circles around her clit.

She grips the blankets behind her head and bites her bottom lip while Dean nibbles at her neck and enters her with his middle finger. She’s beyond coherence, muttering, “Oh god, oh please oh god.”

Dean smirks into her neck and asks, “Please what?” while slipping another finger into her and pressing up into her g-spot.

She moans loudly and bucks deeper onto his fingers. Breathlessly, she whimpers, “Please… down… me… go. Please.

Dean responds with a simple, "Mmm," his lips humming into the hollow of her throat. He’s rock hard, but he will never deny someone his tongue, especially this woman so kind as to oblige Castiel’s voyeuristic request—

Dean had forgotten about Castiel, and briefly looks up at him as he sits up to slide Cheryl’s panties down her legs.

When his eyes meet Castiel’s, the fire burning in Dean switches from a candle to a bonfire. Cas is staring at him with barely hidden desire. His face is flushed and he’s biting his nails, a habit Dean didn’t think Cas even had. His arm is crossed over his chest and he’s slouching a bit. Cas looks so utterly human, so filled with want…

Dean forces his attention back to the task at hand. Cheryl has her eyes closed and is biting her lower lip, squirming under Dean. He trails kisses down her body, stopping again at her breasts to tease and bite her nipples, earning him another shockingly loud moan.

Settling down between her legs, he pauses to kiss and bite her inner thighs, all around her entrance without touching her, licking around her lips while his hands rub up and down her sides.

She has her hands tangled in Dean’s hair, begging for mercy and whispering, “Oh please please please,” over and over. Dean thinks she’s going to come before he even starts, so he dives in, lapping voraciously at her. He runs his tongue up and down her entrance and circles it around her clit until she has to bite her knuckles not to scream.

He pulls away to lick his fingers and then enters her with them, rocking up against her g-spot and keeping rhythm with the swipes of his tongue across her clit.

It’s only a matter of minutes until Dean applies more pressure and steadily pumps into her faster and harder, and she’s so beyond words that she’s biting down on her hand so she won’t scream, breathing so quickly that she might hyperventilate, until finally she comes, hard and loud. Dean can feel her walls clench down on his fingers repeatedly as he continues pumping them into her, riding out wave upon wave of her orgasm.

He sits up and wipes off his face with the back of his hand. Cheryl looks blissed out, blinking slowly and chest heaving. Dean climbs over and reaches into the bedside table to retrieve a condom, tearing the package open and rolling it over himself.

He leans back over Cheryl and kisses her again, and she moans at the taste of herself on him. He reaches down and pumps his dick a few times, then slides it against her wetness while sucking on her lower lip.

It’s only moments before she’s panting into him again, hooking her legs around his back, grabbing his hair and kissing him like she hadn’t just had an explosive orgasm two minutes ago.

Dean continues slowly sliding against her until she meets his rhythm and they’re teasing each other: he barely enters her and then pulls out again, slides up and down against her, over and over, until he can’t hold back anymore.

“May I?” he pants, his voice low and quiet, in her ear.

She can’t speak, only nods and gives a high pitched, “Uh huh."

He puts just the tip of himself in her and then pauses. She trembles below him, waiting, and he peppers her mouth with light kisses before kissing her again, slow and intense. She’s whimpering, and all of their muscles are tensed. Then, when he thinks both of them might break from the tension, he pushes himself all the way into her, pumping into her hard and deep while she claws at his back, gasping and moaning and biting and kissing him. He buries his face in her neck, breathing heavy and unable to control his own gasps.

They find a rhythm, but she’s so tight and perfect that after a few minutes, he’s worried he’ll come, so he pulls out and grips the bottom of his dick while guiding her onto her stomach. She gets up on her knees and buries her face in a pillow.

Dean lines himself up and presses into her again, staring at her perfectly pale, perfectly round ass. He grabs her hips and pounds into her. The noises she’s making are enough to wake up the entire city.

Dean is lost in the moment, eyes closed, rhythmically driving into a beautiful woman whose ass is at the perfect angle, and he feels the familiar pressure in him building. He thinks he’s going to lose it, when he looks up again.

Cas looks destroyed: mouth ajar, panting frantically, clutching at his knees so hard that his knuckles are white. Dean has never seen him filled with such open, wanton lust. Their eyes meet, and Castiel looks at Dean with a white-hot, blatant, burning passion…

That’s all it takes before Dean is coming hard, pumping furiously into Cheryl who is grinding back on him. Dean can’t tear his eyes away from Cas’ as he comes, and Cas can’t seem to control the low, guttural moan that escapes him.

There’s a split second mid-orgasm when Dean imagines fucking Castiel in this very position, and it gives him another intense wave of pleasure before he quickly dismisses the image.

His orgasm finally subsides and he breaks eye contact with Castiel, slowly pulling himself out of Cheryl.

He hears shuffling and looks up to see Cas darting from his chair into the bathroom, and slamming the door shut behind him.