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“So like,” Dean said with a mix of curiosity and uncertainty, “it actually, y’know, feels good?” He squinted at the skin mag he’d accidentally unearthed from the pile of debris on Cas’ desk.
Cas rolled his eyes. “No, Dean. Men have been sticking their dicks into each other for thousands of years because they hated it.”
“Asshat,” Dean said, tossing the magazine at Cas’ head. “But like, most of the girls I know said it really just hurt.”
“Well, most of the girls you know are probably having sex with either teenagers or frat boys, neither of which are particularly known for their sexual prowess or were interested in adequate prep. Or lube,” he added with a shudder.
“Huh,” Dean said, chewing on a fingernail. A slight blush highlighted his freckles, and Cas willed himself not to get a boner while discussing anal sex with his mostly-straight best friend. “I’ve, uh, fingered myself,” he admitted, and that particular battle went out the window. “In the shower. But it didn’t really feel good.”
“Contrary to popular belief, water is terrible lube,” Cas pointed out. “Sexy as shower sex seems, it’s usually pretty awkward.”
“Huh,” Dean said again. He paused for a moment, then blurted, “Do you think you could show me?” Cas’ eyes widened, but before he could respond, Dean continued in a rush, “Like, um, a porn or something? I mean, just to, like – oh, God, never mind.” He dropped his head into his hands, the tips of his ears bright red.
It wouldn’t be the first time their decade-long friendship had gone a little beyond PG-ratings, between curious middle-school jerkoffs over the pilfered Playboys from Dean’s hidden stash to some drunken high school party games that maybe got a little more handsy than necessary. But they were seniors in college now, and Cas’ attraction to Dean had acquired a weight it hadn’t had as teenagers, and he was pretty sure watching gay porn together was a bad way to fuel that fire.
“Okay,” he said, before his mouth caught up to his dick.
Dean jerked his head up. “What?” he said stupidly.
“I said, um, okay.” Cas could feel a twin flush rising on his own face. “I, y’know, know some good sites.”
“Of course you do,” Dean said with a lopsided attempt to regain his usual bravado. “You big gay pervert.”
“Excuse me, I wasn’t the one who compiled a Excel spreadsheet of their favorite porn stars when we were sixteen, sorted by category.”
“Hey, I like to be organized.” He flashed a grin, but his feet were tapping nervously. “So, uh, like…”
“You sure you want to, Dean?” Cas asked. “I can just give you some sites and you can look it up on your own…”
“I’d probably chicken out,” Dean admitted. “And I’m kinda curious.”
“Okay.” They settled back against the wall with Cas’ laptop between them, the way they had since before their respective growth spurts had sent their legs sprawling off the bed. Cas opened his bookmarks, earning a snort from Dean, and scrolled through the list until finally clicking on one.
It started out fairly tame, two young guys about the same late college age, sitting shirtless on a bed and tickling each other in the ribs. Dean glanced at Cas, struck by similarity to their own interactions, but Cas resolutely ignored him.
Eventually the darker-haired actor leaned in, catching the other’s wrists before he could go on attack again, and sucked his lip between his teeth. Cas glanced over as Dean let out a slight, barely-audible sigh, then turned his attention back to the video.
Soon enough they were naked on-screen, but still doing little beyond making out and languidly rolling their bodies against each other. Cas was hard in his jeans, inevitably, but refused to check out his best friend’s crotch.
Eventually, though, the golden-haired guy on the video was laid out on his back, with a lube-slick hand drifting lower and lower down his chest, though the trail of hair on his stomach, bypassing his cock to stroke between his legs. He moaned, bending his knees as one finger pressed further, finally slipping the tip inside.
“Jesus,” Dean murmured, as the guy writhed, trying to take more inside of himself despite the firm hand on his waist. “Is it really, y’know, that good?”
Cas swallowed. “Yeah,” he said, aware of the rasp in his voice. “It can be.”
Two fingers were working in and out by now, with precome visible from both actors in the close-ups. The other guy – the top, Dean thought, with a jolt – did something to his fingers that drew out a long, broken wail.
“I want to try it,” Dean said, breathless. For the first time, Cas allowed himself to look over, to really look, and Dean’s eyes were wide and dilated, mouth wet and cheeks pink – and definitely not unaffected by the video, given the bulge in his pants.
“Um,” Cas said slowly. “You mean… someday?”
“Now,” Dean insisted.
“Dean… you don’t have to – I mean, you could –”
“With you,” Dean clarified. His hands were clenched at his side, clearly trying to stay off his dick, then he drew back. “Unless, I mean, you don’t –”
“Moron,” Cas said affectionately. “Who wouldn’t want. I just, I don’t – it’s not going to get weird, will it?”
Dean opened his mouth, ready for a lust-driven denial, then shut it. “I don’t know,” he said honestly. “But uh, I want this. And, um, I really want it to be with you.”
Cas let out a slow breath. “Jesus, yes.” He paused, chewing his lip. “How do you want to – I mean, we don’t have to –”
Dean just rolled his eyes before leaning in and kissing him, the taste of his mouth not entirely unfamiliar in Cas’.
“So,” Cas muttered unsteadily when they finally broke apart, “clothes?”
“Clothes,” Dean agreed. He pulled off his shirt unselfconsciously, watching in appreciation as Cas did the same, then stopped, fidgeting with the button on his jeans. “Except, uh, can I – maybe I should, y’know, shower?”
“Not on my account, but if you’d prefer to, by all means.”
“Yeah, well, maybe it’s dumb, I just –”
“Go shower, dumbass,” Cas interrupted. “Don’t forget to wash behind your ears.”
Dean just stuck his tongue at him before scrambling off the bed and into the hallway, the bathroom door snicking shut behind him.
Cas flopped back to the bed, throwing an arm over his eyes. Without Dean’s irritatingly irresistible face and form on the bed in front of him, his brain helpfully began providing him a bullet-point list of reasons why this was a really bad idea, and he jammed the pillow over his head with a groan.
By the time the shower shut off, Cas had prepared an argument as to why Dean shouldn’t do this with him, of all people, beginning with best friends and roommates and finally concluding with and you could have anyone, you asshole, and you know it.
All of which promptly shriveled up and died on his tongue when Dean shuffled back inside, a tattered Donald Duck towel slung around his hips, the ridiculousness of which Cas’ dick remained happily oblivious. A stray drop of water dripped down onto Dean’s shoulder, sliding down over the freckled skin before disappearing under the fabric.
“Um,” Cas said intelligently, dragging his eyes back up to Dean’s face.
It wasn’t like he’d never seen Dean in various stages of undress over the years; even as an adult, half the time he’d come home to Dean sprawled in his boxers with a beer balanced on his belly and his ridiculous medical soap on the television. But he’d never really been allowed to look – hell, he still wasn’t entirely convinced he was – but based on the way the shyness in Dean’s face was curling into a small smirk, nobody was complaining.
“Shut up,” Cas informed him.
Dean quirked an eyebrow. “Is this where I say ‘make me’?”
“Oh, my God.” Cas swung his legs over the bed. “The Disney towel is bad enough. Are you trying to kill the mood entirely?”
“I think I’m adorable,” Dean said cheerfully, but the way he shifted from foot to foot belied his nerves.
“Dean,” Cas said gently, neutrally, “we don’t have to do this now. Or at all, obviously. I don’t want you to feel like because you’re curious, you have to go all out.”
Dean looked at Cas consideringly for a moment. Before Cas could barrel on, Dean whipped the towel from around his waist and snapped it hard at Cas’ jeans-clad thigh.
“Ow!” Cas yelped, shifting back on the bed and fumbling for the towel until he could yank it from Dean’s hands. “You fucker!”
“Suck it up, buttercup,” Dean grinned. Cas just raised his eyebrows, still rubbing his leg, and Dean’s naked cock twitched visibly.
Dean snatched the towel back from Cas and sat down on the bed, leaving it in an awkward lump on his lap. He reached a hand out vaguely, paused, and withdrew it. Cas just waited, keeping to his own space.
“You – you are into this, right?” Dean finally blurted. “I mean I know you said you are, and not like I think you’re a liar – hell, don’t think you know how to lie, you nerd, but – I don’t – you’re not just doing this for me, right? Like, you know, just ‘cause you don’t want me to get hurt, or ‘cause you feel sorry for me, or –”
“Dean,” Cas interrupted, resisting the urge to roll his eyes. “Of course I don’t want you to get hurt. But it wouldn’t be a kindness to either of us to do this in spite of myself.” He paused, chewing on his lip. “I’d be lying if I said I weren’t worried about how it could affect our friendship. But… I’d also be lying if I said I didn’t… maybe… want that.” He finished in barely a whisper, waiting for Dean to shrink away, apologizing for giving the wrong idea.
Instead Dean just looked at him thoughtfully. “Maybe that’s a conversation we can have later?” he finally said hesitantly.
Cas looked up, eyes widening in surprise, and nodded.
“Maybe after we finish the naked-getting?” Dean added with another crooked grin. “’Cause dude, you’re wearing, like, way too many clothes.”
“And whose fault is that?” Cas returned, gathering his self-possession.
Dean threw the towel at Cas’ head, then crawled over the bed, settling at Cas’ side. “Um, I was in the shower for like ten minutes. What were you doing, readin’ about honeybees or some shit?”
“Maybe they’re more interesting,” Cas said loftily.
Dean smirked at him then stretched back languidly, knees drifting open minutely as he reached over his head. “That so?”
“Asshole,” Cas said, laughing. “Aren’t you supposed to be the shy virgin?”
Dean snorted. “This may be new t’me, yeah – and, y’know, with you – but is “shy” or “virginal” either really how you’d describe me?”
“Is that a challenge?” Cas asked before he could stop himself.
“…Maybe,” Dean said.
Finally, Cas’ self-restraint broke, and he shoved Dean back to the bed, ignoring the surprised squawk. Straddling his hips, he leaned down and kissed Dean hard, dragging his thumbs purposefully over his nipples. Dean arched reflexively, nearly dislodging Cas, but Cas just tightened his knees.
“Jesus,” Dean gasped when they broke apart. His leaf-green irises were almost swallowed by the black of arousal, mouth spit-shiny and parted. “Don’t – don’t fuck around, do you know?”
Cas just gave him a slightly feral grin, then leaned down to kiss him again, softer, a slow brush of lips and tongue and a little bit of teeth.
“You’ll tell me to stop?” he murmured as they breathed against each other. “If you’re not enjoying anything? I’m not exactly a – a – a sexpert, as they – mrrph.” He swatted Dean’s hand away from where it covered his mouth, glaring.
“Dude, as long as you promise that’s the last time you ever use air-quotes in bed, then yeah, we’re cool. And, yeah, I’ll – I’ll tell you. But uh, could you – lose the jeans?”
“Fine,” Cas acquiesced with a long-suffering sigh. Wriggling on Dean’s hips, with a few semi-intentional grinds over his crotch, he finally managed to kick his jeans and boxers off and onto the floor.
“So,” he said, suddenly shy, as they were both suddenly naked, and sober, and very much in bed together, for the first time in their adult lives.
“Yeah,” Dean agreed. He ran his hands down Cas’ back, over the ripple of muscles. “Christ, like, I knew you got hot, but how’d I miss this?”
“Wish I could say the same,” Cas mumbled. “Would it be weird if I said I’ve been perving on you for a while now?”
Dean burst out laughing. “Think that train’s left the station, dude.” He shifted, until their cocks slid together between their bodies, and they let out a shared groan.
Cas reached down, wrapping his hand around them both. Dean gasped, head falling back to the pillow, but flailed down, grabbing Cas’ wrist.
“I, uh,” Dean said, flush creeping back into his cheeks. “Don’t think I’m gonna last if you keep doin’ that. And uh… I still, y’know, wanna try. You know.”
“Fuck,” Cas groaned, resting his head on Dean’s shoulder. “I mean, not – I mean –”
“Jesus Christ, you nerd,” Dean groaned, even as his voice half-broke with arousal. "If you need an explicit invitation, I’m givin’ you one. Put your fingers in – in my ass.”
Despite his bravado, Dean turned even redder, visible even in the fading evening light. Cas leaned over, fumbling in his desk drawer until he came up with a bottle of lube. Slicking up his hands, he paused, considering the bed’s worth of Dean Winchester laid out in front of him, naked and nervous.
“Turn over?” Dean complied, flipping onto his belly, pressing his head into the pillow and spreading his legs. “And you’ll tell me –”
“Yes,” Dean gasped, as Cas’ slick fingers drifted down his back.
“Okay.” He bent down, kissing Dean’s scapulae and mouthing down his spine, and he nudged his fingers in between Dean’s legs.
“Beautiful.”
Even with Dean’s face buried in the pillows, Cas could see the flush burning on his ears. He planted soft kisses on every freckle he could find, tracing one cool fingertip over his rim.
“Fuck,” Dean breathed. His hands flexed in the bedsheets, and Cas pressed more insistently.
“More?” he asked. Dean just nodded wordlessly, so he slowly pushed inside.
“Oh shit.” Dean tensed around his finger, and Cas froze.
“Not good?”
“Um.” Dean inhaled several deep, steadying breaths, then relaxed with visible effort.
“Oh,” they both gasped as Cas’ finger slid easily in further, up to the second knuckle. Sweat was pricking down Dean’s back, and Cas ran his unoccupied hand down his ribs, biting back the things threatening to spill from his lips.
“Good?” he asked instead.
“Yeah.” Dean shifted gingerly, spreading his legs wider. “A-another?”
“Yeah.” Cas awkwardly drizzled more lube onto his hand, drawing his index finger in and out until he could slip another finger in alongside.
“Jesus,” Dean hissed. Carefully, slowly, Cas pushed both fingers in deep, listening to the sounds Dean was making. Finally, he crooked his fingers and Dean shouted, his knees drawing up the bed. “What – was that –”
“Mm-hmm,” Cas affirmed. “Is it good?”
“Is it –” Dean broke off with a choked laugh. “Yeah. Yeah, it’s good.”
Cas dragged his fingers in and out, rubbing over that spot inside, until Dean took a deep breath, then flipped himself over on his back. Cas fell back, surprised, but Dean just pulled him back on top.
“Wanna see you,” he said. “That okay?”
Cas stared at him for a moment before laying himself skin-close on top of Dean. “Yes.” He flicked his tongue over a nipple, savoring the intake of breath. “Yes, it is.”
He shuffled himself back clumsily until he was straddling Dean’s hips again with their cocks aligned, one hand pushing back into Dean’s hole while the other traced over all the skin he could reach.
“Cas,” Dean whined, twisting underneath him. “C’mon, your cock, let’s – I wanna –”
“No,” Cas said with finality, even as he began working a third finger in. “Next time.”
Dean froze. “Next time,” he grated out.
“Um.” Cas stilled himself, not moving his fingers but not moving away. “Yes?” he tried.
For a moment, Cas thought Dean might run, and he began to slowly withdraw, then Dean grabbed his wrist.
“Next time,” he agreed, urging Cas deeper again.
Cas ground his fingers against Dean’s prostate, thrusting his hips shallowly, savoring the way the precome from Dean’s cock dripped down his own. He brushed two fingers down and brought them to his lips to taste them together, and at that moment Dean clenched around his hand, head falling back and spilling hot and wet between them.
Cas slipped his fingers in and out gently as Dean shuddered through the aftershocks, finally drawing them out and leaning down to press soft kisses over his chest.
“Good?” he asked.
“No,” Dean affirmed without opening his eyes, and Cas’ insides froze.
“Oh,” he said, shifting off. “I –”
“Not ‘til you come, asshat.”
Cas’ eyes shot down to his dick, stupidly, still hard and throbbing, and then to Dean’s face, boneless and happy. “But –”
“Not in me,” Dean clarified. “Next time.” He cracked an eye, still somehow suggestive. “But if I’m the only one who came all over everywhere tonight, gonna be disappointed.”
“Why do I like you,” Cas muttered, even as he leaned down to kiss Dean, fitting his cock between his legs.
“I’m awesome.”
Cas snorted, but with the half-lidded, satisfied look in Dean’s eyes, it only took a few thrusts between his thighs before Cas was coming in spurts over Dean's belly and chest, his forehead cradled on Dean’s sternum.
After a few minutes, Dean snorted, nudging at Cas’ shoulder.
“Wha,” Cas said.
A slightly hysterical giggle escaped from Dean. Cas lifted his head, and Dean dissolved into outright laughter.
“You came on your own chin,” he finally managed. “Oh my God. You came on your own chin.”
Cas wiggled up Dean’s body, until his face was directly over Dean’s.
“Oh no you don’t,” Dean protested, as Cas brought his face closer, smearing streaks of come and saliva over his neck. “You – you fucker!”