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Anything You Can Do

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“I don’t know about it.”

Dean bit his lip, inching closer to the half-open door. He wasn’t usually the kind of guy who spied on his girlfriends, but Daphne had been acting distant all evening. It had been more than ten minutes since she’d left for the bathroom, dinner untouched on her plate. So sue him, he was worried.

“That’s the thing,” Daphne sighed. “It’s not even working as a rebound. I can’t stop thinking about Castiel.”

Heart hammering, Dean peered into the bathroom. Daphne had her back turned to him, leaning her hip against the marble counter.

“I don’t know what I expected,” she continued. “Maybe if it had only been about sex…” she paused, glancing around the room. Dean ducked out of view, just in time. When Daphne spoke again, her voice was lowered, “But even then, I don’t think it would have worked. Between you and me, he’s not as good at it as Castiel was.”

What. The. Fuck?

*

It wasn’t that Dean had ever expected him and Daphne to last. She was an archetypal good-girl, crucifix around her neck, bible in her bedroom drawer and all. The only thing they had in common was needing to get over an ex, and that was what had brought them together.

Daphne was about as far away from Lisa as Dean could imagine, and from what Dean had heard about him he didn’t bear much of a resemblance to Daphne’s ex, Castiel. The guy had sounded like her perfect match, right up until he came out as gay.

So while Dean had been fine with not measuring up to this Castiel dude, he’d at least counted on being better in the one area that counted.

But apparently not.

Not as good in bed? As her gay ex?

He’d sure as hell never gotten complaints before. Dean Winchester took care of the women he slept with. More than a few of them had even told him he was the best they’d ever had. Had they been exaggerating? How could some guy who wasn’t even into chicks be better than him?

Had his whole life up until this point been a lie?

*

“You’ve gotta be kidding me.”

Dean grunted, not even bothering to raise his head from the couch cushion or tearing his eyes away from the TV to acknowledge Sam. On the screen, Rebecca Bunch waved pom-poms, cheerfully singing, “I had a stroke!”

Then Dean’s view was blocked by a pair of gangly legs. “Dude. Move.”

“Really?” Sam had his hands on his hips, eyebrows raised at Dean. “Crazy Ex-Girlfriend?”

“It’s a good show.”

“That you called me a pussy for watching like three weeks ago.”

Dean pointed a finger at Sam. “That’s sexist, man.”

“You were the one who-” Sam huffed, letting his hands drop at his side. “Never mind. Have you even been out of the house since Friday?”

“I bought groceries,” Dean said, which wasn’t technically a lie, if one counted beer and a bag of donuts as groceries.

Sam bent down, pushing at Dean’s shin until he sighed and sat up, making room for them both on the couch. “Are you this upset about Daphne dumping you?”

Dean snorted. If only it were that simple. “Why would I be?”

Sam didn’t answer. A long moment passed, and Dean braced himself, knowing what came next. Then, “Is this about Lisa?”

“Oh my God,” Dean groaned.

“Well, what is it then?”

Dean slumped into the couch. “You wouldn’t get it.”

Sam huffed, and Dean smirked to himself, knowing that he’d won this round. “Fine. Just tell me you’re gonna leave the house soon. Or at least take a shower.”

“I’m not that bad,” Dean groused.

“You’re only saying that ‘cause you’re used to the smell.”

 

They finished the episode together, then Sam left with yet another reminder for Dean to get over himself and rejoin decent society. As Dean looked around the apartment, he couldn’t ignore the nagging feeling that Sam had a point. The curtains were drawn and the kitchen counter was littered with empty take-out boxes and bottles of beer. Dean let out a sigh, allowing himself one more moment of indulgent self-pity, then got to work. 

An hour later, the apartment looked passably tidy and Dean himself was clean as a whistle. Feeling fired up by his small bout of productivity, Dean booted up the computer and logged onto Facebook.

Technically, he wasn’t wallowing anymore. He was doing something about his problems. Technically, it wasn’t even unhealthy behavior, because it wasn’t Daphne he was about to stalk. And really, could it even be called stalking? Technically, the information was all public.

Finding Castiel proved to be easy. Aside from Dean being connected to him on Facebook through Daphne, it wasn’t exactly the most common name. No one had apparently taught Castiel about online safety, because his page was set to public (see?), and Dean started scrolling down his feed.

An embarrassing amount of time later, Dean found himself all out of posts and pictures to comb through, and no closer to finding an answer to any of his questions. The guy was handsome, sure, maybe even sexy, but nothing about him said ‘sex-god-so-good-it-transcends-his-own-preferences-and-makes-Dean-Winchester-pale-in-comparison’.

Dean didn’t get it.

He scrolled back to the top of the page, absentmindedly refreshing his browser, as if an explanation for everything would suddenly pop up. It didn’t, but something else did: a public message from some chick named just ‘Meg’.

‘see u at Harvelle’s tonight stud ;))))’

Dean stared at the screen. ‘Harvelle’s’? As in the Roadhouse? Did Castiel and this Meg chick frequent it? Had to, if they knew Ellen’s name.

And seriously, how many women did this supposedly gay guy have chasing after him?

He licked his lips, filled with indecision. Looking someone up online was one thing, but going somewhere you knew they’d be in real life? That felt like crossing a line Dean wasn’t sure he was comfortable with crossing.

On the other hand, trawling through Castiel’s Facebook page hadn’t turned up anything important. Shouldn’t he be working to move past this? And wasn’t the best way to do so to find out what the hell was so great about this guy?

Reaching into his pocket, Dean pulled out a quarter. He turned it over between his fingers, then tossed it decisively, catching it in his closed palm. Heads he’d go, tails he wouldn’t.

He opened his hand. Tails.

That was that, then.

*

Dean took a deep swig of his third beer, glancing around the Roadhouse once more. When he’d come here an hour ago, Castiel had already been sitting in a corner booth opposite two women, one of which had to be Meg. Dean had taken a seat at the bar where he could see them, then proceeded to spend the next hour watching them as sneakily as he could.

From where he was sitting, there was nothing remarkable about this Castiel guy at all. Granted, he was more handsome in person than in his pictures, but he looked so stiff and serious. At least, until one of the women he was with said something that made him laugh. Then Dean could almost see whatever charm had drawn Daphne to him in the first place.

He was also kind of scruffy, with his beard just past a five o’clock shadow and his flasher trenchcoat looking a size too big. His tie was also turned backwards, and Dean’s fingers itched to reach out and fix it.

Suddenly, Castiel was looking right at him. They were sitting too far apart for Dean to see their color but they were piercing even from this distance, and for a moment Dean felt caught in them.

Then he realized that he’d been caught staring and he turned his head away, cheeks flushing in embarrassment. He took another sip of his beer, more for something to do than because he actually wanted to. He surely couldn’t keep up his surveillance now, they’d be watching to see if he looked their way again.

Dean was so busy pretending to be interested in his beer, he missed Castiel coming his way until he was sliding into the seat next to him.

“I don’t mean to sound too forward,” he started, and holy shit that voice, “but I noticed you looking our way.”

“…Yeah?”

Castiel shot him an uncertain smile. It looked more like a grimace, like he was deeply uncomfortable with the whole situation but soldiering on anyway for god knew what reason. “Were you looking at me or one of my companions?”

“You,” Dean admitted, without thinking. He wanted to smack himself in the next instance. That had been a perfect out! Why hadn’t he said he’d been looking at one of Castiel’s hot friends?

Castiel nodded once, looking like he was bracing himself for something. “Then could I… buy you a drink?”

Dean straightened, putting his beer back down on the counter with a hard thud. “What now?”

“Unless I misinterpreted something?” Castiel looked wary. “In which case, please don’t hit me.”

“I wouldn’t- uh-” Dean sputtered, and he could feel his face turning even redder than before. “I-I mean…” he could feel the words coming, knew what he was about to say, and as much as he didn’t want to, he didn’t feel capable of stopping. “Yeah, sure.”

Castiel brightened. Then he was smiling again, no uncertainty or hesitation in his expression, and for a moment Dean forgot to breathe. “What would you like?”

Dean blinked. “What?”

“To drink?”

“Uh,” Dean glanced at the now empty glass of beer in his hand. “Beer, I guess.”

Castiel nodded and turned to the bartender, trying to catch her attention. Meanwhile, Dean tried to catch his breath, chest constricting in mild panic.

What was he getting himself into?

 

A really fucking great evening, as it turned out 

A couple of hours and three more beers in, Dean had completely forgotten why he’d come to the Roadhouse in the first place. Cas was fun, in a way Dean hadn’t experienced since the good days with Lisa, before he fucked everything up.

Not that Cas was anything like Lisa. He didn’t know anything about movies, or tv shows, or anything that had come out in the last like sixty years for that matter. What he did know about was beekeeping and obscure documentaries and video art, which Dean hadn’t even been aware was a thing until tonight.

Their conversation was easy and carefree enough that Dean didn’t even notice they’d been drifting closer all evening until Cas’ knee bumped against his inner thigh. He gulped, glancing down, and when he looked up again he could see Cas watching him through hooded eyes.

Dean’s stomach flipped (the stupid thing had been doing that all night. Had he had anything weird to eat?), as he desperately wracked his brain for something to say.

“What’s-” his mouth was dry as a desert, so he wetted his lips, stomach flipping again when Cas’ eyes dropped to follow the movement of his tongue, “What’s with the name, anyway?”

Cas frowned. “My name?”

“It’s kind of a weird one.” Dean grinned half-heartedly.  “No offense.”

“None taken. It’s the name of a minor angel. My parents are quite religious. I was, too.”

“Was?” Dean repeated.

Cas cast his eyes downward, looking for a moment as awkward and stiff as when he’d first approached Dean. “I… didn’t have much support from the church when I came out as homosexual. I severed most of my contacts with it after that. The only person I still talk to was my fiancée at the time, Daphne. She was understanding, much more than could be expected of a person in that situation.”

“Oh.” Dean cleared his throat, guilt squirming in his guts. “Well, fuck the rest of ‘em. They sound like dicks.”

Cas snorted. “I suppose they are.” He looked back into Dean’s eyes and just like that, the air between them shifted into something tense and heated. “I would rather not dwell on them, if it’s all the same to you.”

“Y-yeah.” Dean shifted in his seat, leg once more brushing against Cas’ as he did so. “I totally get you. Mind over matter. Que sera, sera. Carpe diem and all.”

He was babbling. Why was he babbling?

And when had Cas gotten so close? He was way in Dean’s personal space, distractingly so, with his stubble and way-too blue eyes and undefined smell that was too subtle and heady to be anything but Castiel himself.

“Perhaps I am being too forward again, but would you like to get out of here?”

This was it. Now Dean had to clear up this misunderstanding, let Cas know that he was straight and not even remotely interested in being picked up by men, no matter how handsome or interesting they were.

Except… this was his chance to prove Daphne wrong, wasn’t it? It wasn’t like Cas was gonna sleep with her again, so she couldn’t find out that way she’d been looking at the past through rose-tinted glasses and that Dean was actually the best she’d had. If Dean could beat Cas tonight, he’d walk away secure in the knowledge that this had all been some big misunderstanding, and his status as sex expert (sexpert? He’d come up with a better phrase later) could go on unquestioned.

It was a crazy idea. But crazy enough to work, maybe? The five beers Dean had downed over the evening seemed to agree on that.

He steeled himself.

“Lead the way.”

 

Even Cas’ apartment looked better than his, Dean reflected moodily as they stepped inside. He didn’t have much time to mope, however, because a second later Cas had grabbed him by the arm and was pulling him in for a kiss.

Dean’s first thought was that there was no way of confusing Cas with a woman. The second was that it didn’t really matter, because Cas was a fantastic kisser. He was enthusiastic, pressing into Dean and coaxing his lips apart with his tongue, crowding him against the door so that their bodies pressed together.

It took a moment for Dean to get with the program but once he did, he did his best to respond in kind. He pulled Cas even closer by the waist, twisting his tongue in a way that had been proven highly effective with most of his ex-girlfriends and hookups. He was rewarded with a soft groan and Cas arching against him.

Then he was pulling away. “Bedroom?”

Dean nodded without thinking, grabbing Cas by the lapels of his coat to snatch another kiss before they started slowly making their way down the hallway. They kept kissing, fervent and mindless, bumping into what seemed like every goddamn furniture in the apartment on the way.

Finally, they made their way to the bedroom, and Cas was backing Dean up to the bed. Dean went willingly, surprised at how easily this all aroused him. He’d never done anything with another man, never even thought of it in more than the most abstract terms (and a couple of… dozens of dreams about Dr. Sexy, but no one needed to know about those). Was Cas really this good?

His legs bumped against the mattress and then he was going down, Cas on top of him, straddling him in one smooth movement.

“I…” Cas pulled away, cheeks flushing, suddenly looking almost coy. “I’m not sure how to ask…”

Dean got up on his elbows, struck with the terrible possibility that Cas had changed his mind and that his whole plan was about to go out the window. “Just ask.”

“Could I,” Cas turned even redder, “Could I fuck you?”

Dean frowned in confusion. “I thought that’s what we were…”

He trailed off, the meaning of Cas’ request hitting him like a train. His mouth dropped open, head spinning with a sudden barrage of images. Shockingly, it didn’t make his dick flag. If anything, it had the opposite effect.

It made sense, didn’t it? Dean had made it this far, and letting Cas… letting him do that would put him in the same position as Daphne. If he was gonna prove Cas wasn’t that good of a lay (he ignored the voice inside his head whispering that it seemed pretty unlikely at this point), this was the way to do it.

“If you don’t want to…” Cas said, looking worried.

Dean swallowed. “I- I do want to.”

It didn’t even feel like a lie.

“Alright.” Cas’ voice was coarse, heated, and it sent an unexpected bolt of lust down to Dean’s gut. “Okay. Good.”

Then he leaned down, stealing Dean’s breath with another mind-melting kiss. Dean arched into it, moaning in approval. He wasn’t so sure about what was coming next, but this he could get used to. Cas kissed like he was dying of thirst and Dean was a fucking oasis in the desert, with all the desperation and eagerness that implied.

Dean got so lost in it, he barely noticed that Cas was tugging his shirt off until they had to break apart to get it over Dean’s head. Not willing to be a step behind, Dean started unbuttoning Cas’ shirt, fingers tingling as they came in contact with the warm skin underneath.

Way too soon, they were down to their underwear. Dean’s head was swimming and he felt disoriented, almost lost. Cas had somehow taken complete control of the proceedings and if Dean hadn’t been trying to prove something, he wasn’t even sure he would have minded. Especially not when Cas’ lips started kissing a trail down the column of Dean’s neck, down to his chest, until his mouth latched onto a nipple.

“Oh, fuck,” Dean gasped, hand automatically grabbing for Cas’ shoulder.

Cas bit down in response, and Dean could swear he felt the bastard smile when he moaned. He definitely didn’t mind the bit of rough treatment, especially not when Cas followed that up with laving his tongue over his nipple to soothe the sting.

But this wasn’t how it was meant to go, so reluctantly Dean tugged at Cas until he raised his head.

“Cas-” he flushed, hardly believing what he was about to suggest, “I wanna blow you.”

Cas’ pupils dilated, eyes dropping down to Dean’s lips. “Later,” he promised, kissing Dean once, open-mouthed and filthy. “I don’t want to come too soon.”

Dean was about to protest, but then Cas was pulling down his underwear, leaving him completely exposed. His mouth went dry when Cas took off his own underwear, revealing an impressive erection. His dick was easily as big as Dean’s, curved but thick and leaking already.

Maybe it was a good thing Cas had refused the blowjob, because Dean’s jaw ached slightly just looking at it.

And that was going to go inside him.

Dean could feel the beginning of panic setting in but he didn’t have much time to react. Cas crouched over him, putting his hands on Dean’s knees and gently spreading them. Dean allowed him to, lust and apprehension turning over in his stomach, making him dizzy with it.

“Relax,” Cas muttered, leaning down to kiss Dean again.

It was a good distraction, because Dean didn’t notice Cas’ hand had moved until it was gripping Dean’s dick and starting to pump it slowly. Dean whined into their kiss, hips unconsciously moving in time with Cas’ hand.

Cas broke away, pressing his lips against Dean’s jawline. “I have lube and condoms in the nightstand.”

“Huh?”

Dean blinked, dazed. He craned his head up and to the right, seeing the nightstand just within reach. He stretched his hand back, clumsily opening the drawer and groping around for what he needed.

Meanwhile, Cas reached between his legs with his free hand, teasing his perineurium, one dry fingertip rubbing over Dean’s hole.  This wasn’t unfamiliar territory to Dean, who’d had some adventurous girlfriends in the past, but the thought of what was coming next made it feel completely new. He couldn’t help grinding down into the sensation, and he couldn’t even feel ashamed about it when it made Cas grin against his neck.

Finally, Dean found what he was looking for, and he pulled his hand back, thrusting the lube and condoms at Cas’ chest. Cas accepted them, with the unfortunate side-effect that his hands were nowhere near Dean’s junk anymore. But that also meant that Dean’s head cleared, and he realized that he needed to step up his game.

While Cas was busy with the bottle of lube, Dean reached down and with only slight hesitation, grabbed Cas’ dick. Cas faltered, groaning when Dean tightened his grip, running his thumb over the head of Cas’ dick.  

“You like that?” Dean murmured into Cas’ ear, pumping his hand and twisting it at the top in a way he knew felt amazing. “Let me hear, baby.”

He was rewarded with a breathless moan and Cas’ hips moving into his hand. He nipped at Cas’ earlobe, licking and kissing a small trail down his neck, and he knew he’d hit a sensitive spot when he sucked on the soft skin just above his Adam’s apple and felt precum spurt out of Cas’ dick.

His upper hand lasted for about ten seconds. Then Cas’ fingers returned between his legs, slick with lube, and he was pressing one finger inside Dean. It stung and felt really fucking strange but something about it also went straight to Dean’s cock. Cas seemed to know exactly what he was doing because it wasn’t long before Dean started to loosen and he was adding another finger, twisting them expertly.

Then his fingers hit something inside Dean that sent a white-hot spark of lust straight through him.

“Holy shit,” he breathed.

Cas hummed, clearly pleased. He kept pumping his fingers inside Dean, occasionally brushing past that spot inside him that made his nerves sing. Dean lost himself so completely in the sensation he didn’t even notice Cas had added another finger until there were four inside him, stretching him wide.

“You’re so warm,” Cas panted into his ear, as if he were affected as deeply as Dean. “So tight. I can’t wait to be inside you.”

It was silly as hell blushing over that, with Cas four fingers deep, but the casual dirty talk had always been a weak spot for Dean.

“Then get inside me,” Dean groaned.

He wasn’t prepared for Cas pulling out, and he couldn’t hold back the whine of disappointment at being suddenly so empty. He watched Cas through hooded eyes as he fumbled with the condom, biting his lip as he wondered how the hell he could take control now, get the upper hand back.

In a stroke of brilliance, Dean clasped his feet around Cas’ calves. Cas shot him a confused look and then his eyes widened as Dean twisted them around, successfully putting himself on top and straddling Cas.

Dean smirked. He could feel Cas pressing between his ass cheeks and he couldn’t resist grinding down a little, feeling the head of Cas’ cock catching on his rim. “Get the condom on, cowboy.”

Cas seemed to catch himself. “I believe you are the cowboy in this scenario.”

“Damn straight,” Dean muttered, bending down to kiss Cas, raising his hips to allow him room to maneuver.

It wasn’t long before Cas’ cock was again pressing against Dean’s hole, and then he was starting to push inside. Dean’s self-confidence faltered as he felt the stretch, and it seemed like half an eternity before the head was finally past his rim.

“You okay?” Cas said, and Dean knew he must make quite a picture, red and panting and eyes wide with uncertainty.

But like hell was Dean gonna give up now. In response, he sunk down on Cas’ cock in one, smooth movement, not stopping until Cas was balls-deep in him. He had to pause again, breath catching in his chest. Maybe he’d been a little ambitious. He felt full to the point of bursting, Cas’ cock feeling fucking huge inside him.

Apparently, none of this was enough to discourage his dick, because it was still hard enough to pound nails. Experimentally, Dean started moving, grinding his hips in small circles. Cas let out a strangled gasp, hands grasping for Dean’s thighs.

Feeling boldened, Dean lifted his hips and ground down. His thighs trembled slightly with the effort of going so slow but he kept his rhythm, almost choking on his tongue when Cas’ cock brushed against that spot from before.

As the sting faded and Dean got used to the stretch, he started moving faster, soon enough bouncing in Cas’ lap. Cas was meeting him thrust for thrust, grabbing Dean’s hips tightly and grinding his cock up inside Dean. Dean couldn’t hold back the breathy, punched-out gasps tumbling past his lips, couldn’t even find it in himself to care when Cas’ cock was filling him so perfectly, sending sparks up his spine with every thrust.

He barely noticed when one of Cas’ hands left his hips, grabbing his cock again and jerking it in time with their movements. He could feel himself hurtling closer to the edge with no hope of slowing down, and when Cas’ hand twisted on his cock just right at the same time as he slammed his hips down, Dean was coming with a drawn-out moan that would make a porn star proud.

Dean,” Cas gasped, and then he was coming too, cock twitching inside Dean.

Dean for his part was trying to catch his breath, hardly believing what had just happened. He’d come first. Cas had won.

Dazed, he climbed off Cas’ lap. Cas didn’t seem to notice his shock, busy getting off the condom. He tied it up and threw it on the floor, kissing Dean’s slack lips before getting up. Dean wordlessly watched him leave, still trying to understand just what the hell had happened when Cas returned with a damp towelette and wiped them both clean.

Then he settled beside Dean in the bed. “Was that… okay?”

Dean bit his lip, holding back the hysterical laughter bubbling in his throat. “Um, yeah. That was… way more than okay.”

Cas smiled at him. It was soft, almost tender, and something inside Dean’s chest clenched. “Do you want to stay the night?”

And really, why not cap the night off with yet another terrible decision?

“Sure.”

Dean laid his head down on the pillow. When Cas leaned in this time, he kissed him back, gears already turning in his head. After all, a morning after meant another chance to beat Cas.

Closing his eyes, Dean grinned to himself as Cas gathered him in his arms. Come morning, this sucker wouldn’t know what hit him.

Chapter Text

Dean woke slowly, drifting into consciousness piece by piece. First, he became aware of an arm wrapped around his midsection and a warm body pressed against his side. Then, the slight headache that signaled he’d been drinking the night before, though not painful enough to really qualify as a hangover. Then, aches in other places, ones that didn’t normally ache.

That last detail caught his attention, and Dean’s eyes snapped open as memories started flooding in. Stalking Daphne’s ex on Facebook and then in real life. Going home from the bar with him.

The sex.

It didn’t make him panic like he might have expected. Probably it was still sinking in, and he’d start hyperventilating in the car on the way home or something. Right now, he just couldn’t wrap his head around it.

He’d had sex with another guy, let him fuck him up the ass. And he’d liked it.

“What the fuck?” he whispered to himself, staring up at the ceiling.

Next to him, Cas started to stir. He let out a long huff, then pulled himself closer to Dean, burying his nose in the crook of his neck. Weirdly enough, Dean didn’t feel the impulse to push him away. This whole morning felt strange, almost unreal. Dean was half-expecting to actually wake up any second.

Cas huffed again, and he was clearly starting to wake up, because his lips moved against Dean’s neck, kissing it softly. Dean twitched at the sensation, then something seized in his chest and yup. There was the panic.

He flailed, and Cas obviously hadn’t been expecting that, because he didn’t even react when Dean pushed him away and sent him rolling off his side of the bed and to the floor. The next moment, his head popped into view, eyes wide and staring at Dean in shock.

Dean for his part was doing a very good impression of a goldfish. “Uhhh.”

“I’m… sorry?” Cas said slowly.

Dean’s jaw snapped close with an audible click. “Ticklish,” he managed.

Cas didn’t call him out on the half-assed excuse. He got up, rubbing his hip, giving Dean an uncertain smile. “Do you not do this often?”

Do what? Wake up next to strange guys after having amazing sex with them that throws your whole self-image into question?

“Not really,” Dean admitted.

Cas sat back down on the bed next to him, a little too close for comfort. “Me neither,” he told Dean. “As a matter of fact, you’re the first person I’ve slept with since I broke it off with my fiancée.”

“Bullshit,” Dean blurted. “You were way too good at that not to have done it before.”

Cas blushed but looked clearly pleased. “I did do it before I met Daphne. Besides, there is not a whole lot of difference between sleeping with a man or a woman. Aside from my attraction to them,” he added thoughtfully. “I just pay attention to what the other person wants.”

“And boss them around,” Dean added, thinking back to the night before, and not feeling a twinge of lust at it, my god.

“You didn’t seem to mind that.”

Great, now Dean was the one who was blushing.

“What about you?” Cas looked Dean over. “You seemed to enjoy yourself last night, but…”

But now he was on the border of freaking out.

“Just not used waking up in beds that aren’t mine,” Dean lied, and pretty shamelessly. Before Lisa, his whole sex life had revolved around one-night stands.

Cas nodded absentmindedly, eyes darting down to Dean’s lips. “And now that you’ve… caught your bearings?”

It didn’t take much to understand what was on his mind, even for a clueless idiot like Dean. Now was the time to make an excuse and bolt. Except…

Dean hadn’t really shown he was better at sex than Cas, yet, had he? Which meant he hadn’t done what he’d set out to do, which meant that if he backed out now, it had all been for nothing.

Besides. “I did promise you a blowjob, didn’t I?”

The effect was instantaneous, a bright pink blush spreading over Cas’ cheeks. He swallowed audibly. “Technically, you didn’t promise-”

Dean shut him up with a kiss. They both had morning breath so he kept it short and clean, trailing his lips down Cas’ neck and guiding him with a hand on his waist to lie back down. Cas was naked, which made the proceedings simpler, but that also meant that his rapidly hardening-dick was impossible to ignore as it bumped against Dean’s hip. Dean ignored it, at least for now, focusing on the parts of Cas’ anatomy he had experience with.

Cas didn’t seem to have sensitive nipples, but judging from the low keen that escaped him and the way his hips buckled he liked it when Dean sucked on the skin just below his stomach. Dean filed that spot away in his mind, along with the spots above Cas’ collarbone and behind his ear. Not that he’d need that information for later but hey, it never hurt to be prepared.

Pretty soon, Cas’ erection became all but impossible to ignore. Dean still did his best, kissing and licking and stroking the area just around it, on Cas’ pelvis and the insides of his thighs.

“Dean, please,” Cas whined.

Okay. Dean had to stop stalling. He stared down at Cas’ dick, now fully hard and leaking, and felt a twitch in his own that was surely just coincidental. He glanced up, but Cas wasn’t looking his way, head thrown back on his pillow.

Drawing a deep breath, Dean leaned forward and took the head of Cas’ dick in his mouth. It was warm and weirdly spongy, and the taste of precum was bitter on Dean’s tongue. It didn’t taste that different from Dean’s own come, which shut up, he’d only tasted because he was curious.

Carefully, Dean sucked on the head, grasping the rest of Cas’ dick with one hand and pumping it slightly. He tongued at the slit, remembering what he himself liked, and was rewarded with a guttural groan. Sucking dick honestly wasn’t as strange as Dean had expected; it really was just one step away from a handjob, which was just one step away from masturbation. Totally not gay.

Okay, Dean acknowledged to himself as he tried sucking Cas in deeper. Maybe a little bit gay.

He swallowed instinctively around Cas’ dick, causing Cas to thrust into his mouth. It went deeper than Dean expected and he just barely held back from choking. Weirdly enough, his cock went from zero to half-hard at that. Flushing, Dean grasped Cas’ hips and with a push of his hands, encouraged him to move a little. Cas took the hint and started to thrust in small, manageable movements that pushed his dick against Dean’s tongue but not down his throat.

Dean couldn’t help himself; he started moving his own hips against the mattress, seeking friction, and began sucking in earnest, tongue moving around the head of Cas’ cock and down the shaft, moaning encouragingly. Cas’ hand shot down, fingers tangling in Dean’s hair but not pushing, just letting them rest there, digging into Dean’s scalp whenever he ran his tongue over the slit of Cas’ dick.

“That’s it,” Cas groaned, still thrusting in a steady rhythm. “Fuck, so good, so eager for it, Dean-

And Dean was so turned on he could barely focus on sucking Cas’ dick, hearing those words tumble from Cas’ lips in that deep, rasping voice, feeling his dick twitching on his tongue. He sucked him down deeper, rocked his head, and he felt like the world’s cheesiest porn star as he moaned around Cas’ dick, hips driving against the mattress, seeking some sort of relief.

He kept jerking the part of Cas’ dick he couldn’t quite wrap his lips around, the other hand reaching between Cas’ legs to play with his balls. Dean felt them twitch in his grip, heard Cas gasp breathlessly, and that was all the warning before Cas was coming, seed spurting from his dick and into Dean’s mouth. Dean swallowed on instinct, the bitter taste overwhelming his taste buds.

He kept sucking until Cas went soft (hey, if you’re already swallowing come, might as well make sure none of it gets in the sheets). Then he pulled back with a soft pop, looking uncertainly back up at Cas.

This time, Cas was looking at him, a lazy smile playing on his lips. “I enjoyed that very much.”

Dean swallowed. His own dick throbbed, nowhere near satisfied yet.

“Come,” Cas directed, pulling at Dean’s shoulder.

Dean went willingly, lying down next to Cas, gasping in surprise when Cas grabbed his dick. He started jerking, hard and fast, the friction burning a little from the lack of lube but feeling so, so fucking good. Dean bit back the moans bubbling in his throat, hiding his face in the crook of Cas‘ neck as he came, hips twitching helplessly into Cas‘ hand.

Okay, so that had taken no fucking time at all. But then again, Dean had blown Cas and gotten just a handjob in return.

So did that make them... even?

Dean was still pondering this when Cas leaned in and kissed him on the lips, oddly sweet considering what they‘d just been up to.

“Would you like breakfast?” Cas asked as he pulled back, still near enough so that Dean could feel his breath on his cheek.

Dean licked his lips. “Uh, sure.”

 

Dean might not have accomplished what he’d set out to do, but Cas’ omelets nearly made up for that. The man was a damn good cook, and his coffee wasn’t half bad either.

When Dean got dressed and ready to leave half an hour later, he almost felt sorry to be leaving Cas behind. Probably because he hadn’t been able to prove Daphne wrong.

Yeah, that had to be it.

Cas leaned against the doorframe as Dean shrugged on his jacket, smiling contently. As Dean got ready to leave, he slipped a piece of paper into Dean’s pocket.

“My phone number,” he explained. “I like you and I’d like to spend more time with you.”

Something in Dean’s chest clenched. He leaned in, gave Cas one final kiss goodbye. “I’ll call.”

He felt a little bad about lying, but he probably would have felt even worse at seeing any sort of disappointment on Cas’ face. Better to leave this on a benevolent lie.  

Chapter Text

Three days later, Cas’ number was still burning a hole in Dean’s pocket.

He honestly didn’t know why he hadn’t thrown it out already, only that something kept him from doing so. Maybe it was because, the whole gay sex thing aside, Cas seemed like a cool guy to hang out with. Dean didn’t have the easiest time getting along with people when he wasn’t putting on the charm but with Cas, it had been effortless.   

That had to be it. Dean just needed more friends. He’d lost a lot of them when he and Lisa broke up, since most of them had been her friends more than his, so it was only natural that he’d want new ones.

Maybe he could call Cas up for drinks. Dean was self-aware enough to know the truth would make him sound insane, but coming up with an explanation for why he'd temporarily seemed not straight shouldn't be too hard. He could tell Cas he’d just been trying something new, hadn’t liked it, but still wanted to be friends. Staying friends with an ex was always a terrible idea in Dean’s experience but the rules had to be different for drunken hook-ups. Besides, Cas was a nice guy. He’d probably be cool with it. 

Mind made up, Dean pulled up Cas’ number as soon as he got off work on Friday and shot him a quick message.

‘drinks at harvelle‘s tonight? this is dean btw‘

He got a swift response.

‘Only if you’re buying this time :) '

Dean smiled to himself. This was exactly what he liked so much about Cas. What kind of a grown man used emoticons?

‘ur such a dork. see you at eight' 

He pocketed his phone, feeling pretty good about himself. They could totally be friends. This was gonna work out great.

 

 

Dean had gotten plenty of practice opening his apartment doors blinded with one hand while mid-kiss with some handsy woman. Cas wasn’t a woman, but the principle was essentially the same. It was a good thing, too, because Dean was about three seconds away from saying ‘fuck it’ and just stripping in the hallway.

The doors opened with a soft click and then they were tumbling across the doorway, still connected at the lips. Dean just barely remembered to grab his keys from the keyhole before they were inside and the door was slamming behind them.

Considering this was only their second time doing this, they were surprisingly practiced at moving down the hallway and stripping on the way. By the time they got to the bedroom, they were down to their underwear.

“How do you want me?” Dean asked as they finally parted for air, not even realizing the way it sounded until he’d said it.

The way it made Cas groan, he couldn’t bring himself to regret it. “On the bed, hands and knees.”

Dean swallowed, dick throbbing in his boxers. Riding Cas had been a new experience to say the least but he’d still been technically on top. This felt entirely different, and for some reason it had his knees almost buckling with lust. He almost tripped over himself getting to the bed, chucking his underwear off as he went.

Hesitation crept into his chest as he took his position. He felt so vulnerable and exposed like this but before he could get too worked up about it, Cas was climbing on the bed behind him. There was a small sound that took Dean a second to place. 

“Did you bring your own lube?” he asked, incredulous but mostly amused.

A finger brushed over Dean’s hole. The lube was still cold and it made Dean twitch away instinctively. One hand grasped his hip, keeping him still.

“It never hurts to be prepared,” Cas responded, sinking the tip of his finger into Dean’s hole and twisting it.

There wasn’t much talking after that. Cas made quick work of fingering him this time around, like he couldn’t wait to get his dick inside Dean, and as much as Dean liked to take his time with foreplay there was also something extremely hot about Cas being so eager to fuck him he couldn't be bothered with more than the most rudimentary preparation.   

In what felt like no time at all, Cas was pulling out his fingers and grasping Dean’s hips with both hands, rubbing the head of his dick over Dean’s hole. Dean pushed his hips back, which earned him a quick slap on the ass. He bit back a moan, dick twitching and leaking precum on the mattress. If Cas’ fingers hadn’t already gotten him hard, that slap might have done it.

Slowly, Cas started pressing inside. It was somehow just as overwhelming as the first time, his dick feeling huge and unyielding compared to his fingers. He didn’t go all the way inside yet, pumping with small movements, pushing his dick only half-way inside before pulling it back out again almost completely, head popping past Dean's rim and inside him again. It was an unbearable tease. Dean tried to push back, get him deeper, but Cas kept a vice grip on his hips, keeping him right where he wanted him.

“Come on,” Dean groaned. “Fuck me already, Cas.”

Cas’ dick pressed just a little further inside, then he was pulling back out. “I am.”

Dean growled in frustration. “You know what I mean.”

“I’m afraid I don’t.”

The fucker sounded so amused, too. For how fast he’d gotten the prep over with, he didn’t seem to be in a hurry now that he had his dick inside Dean.

“The hell you don’t. Stop teasing, and fuck me like you mean it!”

Cas’ hands tightening their grip was all the warning Dean got before he plunged all the way inside, immediately picking up a fast and hard rhythm. A moan tore itself loose from Dean’s throat when the head of Cas’ dick brushed against his prostate. Cas took the hint and angled his thrusts just right to keep hitting that spot, again and again. Dean's upper half collapsed against the mattress, and he gave up completely on trying to hold back any sounds, breathless grunts and moans tumbling past his lips, feeling punched out of his body by the relentless way Cas drove into him.

It wasn't anything like last time, when Cas had seemed in control of himself the entire time. It felt almost mindless, like Cas was past anything but chasing his own pleasure, using Dean's body to get it, and it shouldn't have been so hot but it was

"That's it," Dean gasped, "fuck me, Cas, fucking use me, c'mon."

Cas groaned, bending over Dean’s body as he kept fucking into him, pace fast and merciless, one hand leaving his hips to grab Dean’s shoulder instead, using the leverage to fuck even deeper. Dean pushed his hips back, trying to keep up with Cas’ rhythm. He soon gave up, instead focusing on tightening his muscles, making Cas’ dick feel impossibly bigger inside him.

“Oh,” Cas gasped, pressing his forehead against Dean’s shoulder, his movements growing faster and smaller. “Dean, I-”

He cut himself off with a long, drawn-out moan, hips stuttering and then stilling. Dean could feel his dick pulsing, and he couldn’t hold back a whimper at the realization that Cas was coming inside him. A condom between them, but still.

Cas’ hands loosened their grip on Dean’s shoulder and hips and then he was straightening and pulling out of him, dick already softening. Dean didn’t have much time to get disappointed, however, because then Cas was grabbing his cheeks, spreading them and licking over Dean’s hole.

Some animal sound escaped Dean’s lips, heat running through him like lightning and pooling low in his gut. Cas’ tongue felt so weird, so warm and wet, Dean couldn’t decide whether he wanted to push into it or pull away. Then Cas was spearing his tongue, pushing it inside him, and Dean’s brain melted into a puddle.

Cas ate him out with incredible ferocity, tongue moving over and inside Dean’s hole, the sound echoing around the room along with the almost continuous moans and whimpers coming from Dean’s mouth that he just couldn’t keep in. It was so strange, unlike anything he’d felt before. His dick was rock hard and leaking, and it felt like a stiff breeze could finish him off.

Instead, what did it was Cas raising his hand a smacking his ass again, right as he plunged his tongue inside Dean’s hole and twisted it in some miraculous way. Dean bit down on his lips as he came without even a hand on his dick, pleasure washing through his body in waves.

He collapsed against the mattress, with just enough presence of mind to avoid the wet spot, gasping as if he’d just finished running a marathon.  “Fuck.”

Next to him, Cas laid down and stretched out. “That was enjoyable.”

‘Enjoyable’ was putting it mildly, Dean thought. ‘Mind-blowing’ might fit better. It had been so good, he hadn’t even realized while it was happening that it had not been the fucking plan.

What the hell was it about Cas? Get a couple of beers in Dean (literally only a couple this time, which was just embarrassing) and he was ready to jump into bed with him and bend over for his dick.

At least Cas had come faster this time around. Did that mean Dean had accomplished his goal? What even was his goal anymore? Dean couldn't remember. He felt like Cas had literally fucked his brains out.

Cas rolled over, wrapping his arm around Dean’s midriff and pressing a kiss against his shoulder. “Can I stay the night?”

Like Dean could tell him no.

*

Clearly, the solution was to avoid alcohol around Cas. Something about mixing the two did some strange things to Dean’s head, even if he barely got tipsy. This time around, he asked Cas to meet him at a café. Nice, neutral location to break it to him how very not gay Dean was but that he still wanted to stay friends.

Cas was already there when Dean arrived, sitting at a table by the window. He smiled up at Dean when he approached 

“I already ordered something,” Cas told him. “I hope you don’t mind."

“You did?” Dean asked, sitting down.

“Maybe it was presumptuous of me.” Cas looked suddenly nervous. “But you mentioned the other night that you had a special fondness for apple pie.”

Dean was pretty sure the words he’d used had been much more graphic than ‘special fondness’. But still. “You remembered that?”

“It was only a few days ago,” Cas said, shrugging. 

Something fluttered in Dean's chest. “That’s, uh… thanks. I appreciate it.”

“I’m glad.” Cas was smiling again, looking relieved. “I was worried I had overstepped my boundaries. I suppose this is technically only our first date.”

Whatever had knocked loose in Dean’s chest went even crazier at the sound of that. Which, no, Cas thinking this was a date was a bad thing. “Yeah. About that.”

Cas cocked his head. He tended to do that when listening intently, Dean had noticed. If Dean thought that kind of thing about other grown men, he’d call it adorable.

“I- I’m not… that is, I never-” Why was this so hard? Dean wasn't even at the part where he needed to come up with excuses yet, this was just the truth, plain and simple. “I don’t really date guys. Or sleep with them. I’ve always been into women. It’s just...”

“It’s alright,” Cas interrupted. “I understand.”

Dean swallowed. “You do?”

“Of course. It’s not too long ago I was in your shoes.”

“Huh?”

“It can be difficult coming to terms with your sexuality when you’re already an adult.” Cas offered a sympathetic smile. “When you feel like you should be past questioning who you are. Not realizing you’re gay until you’re into your late twenties-"

“I’m not gay,” Dean blurted. “I like women.”

Cas’ eyes widened. “I’m sorry, I didn’t mean to imply- I was only talking about my own experience. I know bisexuality is real, you don’t have to worry about that.”

Wait, what?

That was just- of all the ridiculous-

Bisexual? Dean?

Someone cleared their throat. Dean looked away from Cas’ worried face, to the waitress standing next to them, holding two plates.

“You guys had the apple cakes, right?” she asked.

“No, sorry,” Cas said. “I ordered the apple pie for us both.”

The waitress sighed, looking profoundly bored with the entire exchange. “We’re out of pie.”

“Oh.” Cas glanced at Dean. “I suppose we could go somewhere else?" 

“No!” Dean blurted, before he could think twice. Both Cas and the waitress looked at him, eyebrows raised, and he could feel himself blushing under their attention. “I mean, it’s okay. I like cake, too.”

 

 

They ate their cakes, which turned out to be pretty good, and neither one of them brought up their previous conversation again. Instead, they talked about their families, finding common ground with shitty dads and awesome siblings, and Dean found himself lecturing Cas about the sorry state of current blockbuster cinema. To his credit, Cas at least looked interested, and Dean did his best to follow along when he in turn talked about a video art installation his friend was producing. 

The whole thing straddled a strange fence in Dean’s head between date and just-friends-hanging-out, and he honestly wasn’t sure which side he wanted it to fall on.

God, this was confusing. 

When they walked together to the parking lot, Dean still hadn’t made his mind up.

“You sure you don’t want a ride?” Dean asked, one hand in his pocket and nervously fidgeting with the Impala’s keys.

Cas shook his head. “Thank you, but I only live a couple of blocks away. Besides, I could use the exercise.”

“Coulda fooled me.”

Dean wanted to bite down on his tongue as soon as he’d said it, especially with the filthy grin Cas shot him. Like the situation wasn’t confusing enough, he had to make it worse by flirting. He kept his mouth shut the rest of the way until they reached the Impala.

“Well,” he said, leaning against her side. “This is me.”

He wasn’t prepared for Cas to lean in, or for the almost aggressive way he kissed Dean, pressing him against his car. Instinctively, Dean kissed him back, arching into Cas’ touch when his hand came up to palm Dean’s cheek.

It was over entirely too soon, Cas pulling away with a soft smile.

“I’ll call you soon,” he promised.

Dean could only nod, watching stupefied as Cas walked away, lips still tingling and mind still spinning.

Chapter Text

It wasn’t like Dean didn’t know what bisexual meant. He had Netflix, okay? He’d blown through both seasons of Crazy Ex-Girlfriend in one weekend, he knew that being bi was a thing.

He’d just never thought of it as a thing that applied to him. Sure, he’d always had kind of a crush on Harrison Ford, but everyone had same-sex celebrity crushes. There was also Dr. Sexy, but Dean maintained that his sexiness defied gender or sexuality.

Also, that was like two guys against hundreds of girls. Dean was definitely more about the ladies. This little… aberration with Cas didn’t change that.

So, fuck it. Dean was done agonizing over it. He liked being around Cas, the sex was good, what else was there he needed to know? He’d probably get the whole ‘liking dick’ thing out of his system in a couple of weeks, and then he could give Cas the friend speech.

For now, he’d just enjoy the ride.

*

And it was a pretty good ride. Over the next month, most of Dean’s free time seemed to be spent with Cas. They went to pubs, and cafés, and gallery shows. They stayed in, taking turns picking out movies to watch and shows to binge. More often than not, they ended up in bed (and, one very memorable time, the Impala’s back seat).

It was good. Fun. Cas sure as hell was a better rebound than Daphne had ever been. Dean went days without thinking about Lisa, which was a first since she’d dumped him.

Things with Cas were simple. And then, suddenly, they weren’t.

 

 

It was rare for Dean to go out without Cas these days but sometimes a guy just needed a solitary drink and burger at the Roadhouse.

Dean thought he was giving off some pretty clear ‘leave-me-alone’ vibes, sitting kind of hunched over his plate in a corner booth, but half-way through his meal someone walked up to him.

“Dean? Dean Winchester?”

Dean swallowed his bite, looking up. It took him a second to place the pretty blonde in front of him. “Jamie?”

“You remembered,” Jamie said with a smile. “It’s been a while.”

Dean shrugged. “I don’t pass through Canonsburg a whole lot.”

He’d met Jamie during a road trip he’d taken with Sam a few years back. Overall, the trip had been a fucking disaster, but meeting Jamie had been one of the few bright spots. She’d been a lot of fun. A dirndl had been involved, if Dean recalled correctly.

“I was on my way out,” Jamie said, “But I’ll be in town for a couple of days, if you want to hang out."

Straight to the point. Dean admired that about her. Under other circumstances, he might have taken her up on her offer. “I’m kinda seeing somebody.”

“Oh!” Okay, Jamie had definitely not known Dean well enough to be so surprised by that. Or had his aura of perpetual bachelorhood been that visible? “Well, if you’re ever single and passing through Canonsburg again, look me up.”

She left with a small wave, which Dean absentmindedly responded to. He went back to eating his burger, and it took him a full minute to process what had just happened.

Had he just turned down an attractive and, he knew from experience, extremely talented woman because he was seeing somebody?

Well, shit.

 

 

Dean didn’t like asking for romantic advice. Most of his friends weren’t qualified to give it and those who were tended to be insufferable about it. He wasn’t even sure this thing with Cas counted as ‘romantic’. It was definitely at least a little bit ‘gay’, though, which narrowed Dean’s choices down to just one. 

Luckily, Charlie was both free and close by so fifteen minutes later she was sitting down in Dean’s booth. She wasn’t the best at keeping secrets, so Dean had planned on just telling her the necessary details, but somewhere in the process the whole story spilled out of him like so much word vomit.

“So?” he finished with, taking a bite out of his last fry. “You got any advice for me?”

Charlie gaped at him. “Is this a joke?”

Dean frowned. “Did it sound like a joke?”

“Kind of, yeah.” At Dean’s offended look, she held up a hand. “But what do I know. Maybe this is a thing all straight dudes go through at one point or another.”

Dean squirmed in his seat, feeling warmth rising to his face. “I mean… I might not be. Entirely straight.”

“Would it be really insensitive of me to say ‘duh’?”

“You’re terrible at this,” Dean sulked. “I shoulda called Sam.”

“I’m sorry.” To her credit, Charlie looked it. “I’m just not sure what you expect me to say. You’re the only person I know who could fall ass backwards into a loving relationship with the man of your dreams.”

Dean held up his hand, heart jumping in his chest. “Back the fuck up. Who said anything about Cas being the man of my dreams? I don’t dream about men.”

“Except Dr. Sexy.”

“Except Dr. Sexy,” Dean allowed, because he was way past the point of denying that one. “Anyway, this thing with Cas is just… temporary insanity or something.”

“This thing with Cas is a relationship,” Charlie said, giving Dean a look that was far too close to pity for his tastes. “And whether you like to admit it or not, the fact that you turned down Jamie means you see it that way too.”

And Dean wanted to argue. He had about fifty reasons why Charlie was wrong, but as soon as he tried to voice one it seemed weak or non-existent and died on his tongue


“It’s not-” he tried anyway, the rest choking in his throat. He tried again, “We’re not… I’m not…" 

Charlie snuck a sip of his beer, giving an apologetic shrug. “I’m sorry, Dean, but it kinda looks like you are.”

Dean’s jaw snapped shut. This wasn’t going the way he’d wanted. He wasn’t sure what he’d expected from Charlie, but some part of him had been hoping she’d have a totally innocent explanation for why he’d turned down Jamie that he just hadn’t thought of himself.

He hadn’t been expecting this mountain of uncomfortable realities to be brought to his attention. Or really, only the two, but they felt enormous enough on their own.

One, he liked Cas. Like liked him.

And two, he wasn’t straight.

Charlie reached across the table, smacking Dean’s arm companionably. “Welcome to the club, dude.”

Goddamn it.

*

“Are you alright?”

Okay, so Dean probably should have cancelled this date. He’d planned on it, and on avoiding Cas until he got his head on straight (so to speak). But even thinking about it had made his stupid heart ache and he hadn’t found it in him to pick up the phone and call Cas before he came over.

So here they were, sitting on the couch in Dean’s living room and eating pizza that they’d ordered because Dean had been too preoccupied with his gay (bi?) crisis and had burnt the meatloaf he’d promised to cook.

“Sure,” Dean said, taking a bite of his slice. “Why?”

Cas just raised his eyebrows at him, which, fair enough. The stench of burnt meatloaf was still lingering around the apartment and Dean was pretty sure he hadn’t looked Cas straight in the eye once this entire evening.

“I’m just thinking through some things,” Dean admitted.

“Should I be worried?”

Cas’ tone sounded light but at this point Dean knew him well enough to detect the worry underneath. He wanted to reassure him that he shouldn’t but he wasn’t even sure if that would be a lie or not.

When a few moments passed and Dean still hadn’t said anything, Cas cleared his throat. “Is this about us?”

Dean swallowed. How much could he even share with Cas without sending him running for the hills?

“I like you, Cas,” he finally settled on, because that much was true.

“But…?”

Dean shrugged. His eyes were laser focused on his lap, the pizza slice hanging limply in his hand. He put it back down on the cardboard, his appetite gone. “I don’t know. I didn’t expect things to go this way. I didn’t even really know I liked guys until we…”

From the corner of his eye, he could see Cas tilting his head. “You seemed sure enough when we met.”

“Uh.” Dean scratched his chin. “Let’s just say I had something to prove to myself. But I’m way past that now and I have no idea what I’m doing.”

Cas was silent for a scarily long time. Dean finally risked a glance up, but it did him no good. Cas’ eyebrows were knitted together, his lips turned down in a slight, thoughtful frown, and Dean had no idea what that expression even meant.

“But I do like you,” he hastily added. “And I wanna keep seeing you. I’m just not sure-”

He was stopped short by Cas’ lips pressing against his. He closed his eyes, relief blossoming in his chest. At least he hadn’t completely fucked things up yet.

Cas pulled away far too soon but he was smiling softly, so that had to be good. “I like you too, Dean, and I want to keep seeing you. Does it really have to be more complicated than that?”

Dean licked his lips. “Exclusively?”

“What?”

“You wanna keep seeing me exclusively?” he repeated, feeling like a massive girl. But fuck it, if being a massive girl would keep him from stewing in uncertainties and doubt, then slap a bow on him and call him Deanna.

“Of course.” Cas’ brow furrowed. “Wait, have you been-”

“No!” Dean cut in, grabbing the front of Cas’ shirt as he made to pull away. “No, I haven’t. We just… never made it official,” he finished lamely. So not only was he a girl, but a teenage girl as well. Great.

Cas seemed to sense what he was thinking, because he smirked. “If you want, I could open Facebook and-”

Dean shut him up with another kiss. Cas responded well, crowding him against the back of the couch, one hand cupping Dean’s cheek and grabbing Dean’s thigh and pulling him into a more intimate position. They broke for air, both smiling like absolute fucking saps.

“Are you finished eating?” Cas asked. “Because I would like to take my boyfriend to bed right now.”

Boyfriend. It was such a juvenile term but Dean felt like a giddy teenager right now, anyway. “Oh, I’m full." 

Cas’ smile turned positively feral. “Not yet, you aren’t.”

 

They never even made it to the bed. The couch was comfortable enough, anyway.

Chapter Text

Dean picked up the phone on Thursday afternoon, punching in Mom’s number and making the call before he could second-guess himself. Introducing Cas to his family was just the next logical step, and it had to happen sooner or later.

It rang a couple of times before Mom picked up, sounding out of breath. “Hey, sweetie.”

“Am I interrupting something?”

“Nah,” Mom said. “Well, kickboxing class, but I’m fine with taking a break.”

“Are you allowed to have your phone with you?”

Mom snorted. “What are you, my instructor?”

“Rebel.” Dean took a deep breath, stomach squirming with nerves. “I was wondering if you wanna come over for dinner on Saturday. I’m gonna ask Sam and Eileen, too, but I can reschedule if any of you-”

“I’d love to,” Mom cut him off. “Any special occasion?”

Dean swallowed. He could tell from her voice that she thought she had it figured out. And she almost did. “Kinda. I, uh, met someone.”

“That’s great!” As expected, she didn’t sound surprised. “What’s her name?”

This was it. Time to get it out of the way.

“His name is Castiel.”

There was a long silence on the other end. Dean’s stomach sank, and he was one moment from breaking and saying he’d been kidding, when Mom spoke.

“I’m sorry, I think I misheard.”

Dean laughed weakly. “You didn’t. Cas is a guy, and he’s my boyfriend. I guess.”

“Oh.” Mom’s tone was impossible to read. “Can’t say I saw that coming.”

“Will you still be over on Saturday?”

There was another scary pause. Then, “Of course, sweetie.”

“Cool.” Dean nodded to himself. “Okay, see you then.”

He hung up without waiting for a response. That was two down, the entire rest of his friends and family to go.

Piece of cake.

 

Sam sounded even more shocked than Mom, although he recovered quicker.

“Definitely didn’t see that coming,” he said with a slight laugh, and Dean felt the knots in his stomach ease at the relaxed tone in his voice. Not that he’d really expected Sam to take it badly.

“That’s what Mom said.”

“So, what does that make you?” Sam asked. “Bi?”

“I guess.” Dean sat down on his couch, letting out a sigh of relief. “Man, I’m just glad you didn’t guess gay.”

“I know you, Dean, there’s no way you faked your attraction to all those dozens of women.”

“I wouldn’t say dozens-”

Dozens,” Sam repeated, with the kind of darkness in his tone that belied some childhood trauma. Okay, so he’d caught Dean in compromising positions a few times over the years. That still didn’t excuse him basically calling Dean a slut. “And it’s not like I don’t know bisexuality is a thing. I’ve seen Crazy Ex-Girlfriend.”

Dean snorted. “Whatever, geek.” He cleared his throat. “And, uh, thanks. For taking it so well.”

“Don’t mention it,” Sam said, voice softer. “See you Saturday?”

“Yeah, see you then.”

*

The next day, Dean got home from work and Mom was sitting on the couch, waiting for him. He hadn’t been expecting to face her until tomorrow, so the sight of her filled him with unexpected dread. Why the hell would she be here now?

“Mom.” He closed the door behind him, clinging to the doorknob for a moment before letting go. “What are you doing here?”

As he approached her, Mom indicated for him to sit down next to her. Once he did, she reached out and took both of his hands in hers. His heart tightened, hands limp in her tight, slightly damp grasp. Looked like he wasn’t the only one nervous.

“First of all,” she said, “I just want you to know that I love you very much. I will always be your mom, and you will always be my child, and nothing changes that.”

“… Okay,” Dean said, dread replaced with confusion. Not that he didn’t prefer this to her being uncool about it, but this was seriously weirding him out. Mom was loving, sure, but they’d never been the most outspoken family. “Is this about Cas?”

“And I want to thank you,” Mom continued, as if he hadn’t just spoken, “for being honest with me. And I want to learn more. And, uh…”

Understanding dawned. Dean pinched his lips together, holding back his laughter. “You memorized that speech, didn’t you?”

Mom huffed in frustration. “Not well enough, apparently.” She let go of one of his hands, tucking a stray lock of hair behind her ear. “Look, I know I’m not the best at talking about this stuff. I figured I should look up what to say so I wouldn’t screw it up.”

Something caught in Dean’s throat. He squeezed the hand still holding his. “You’re doing great, Mom.”

“Yeah?” She smiled wryly. “So that speech was okay?”

“I wouldn’t go that far.”

She smacked his chest with the back of her hand. “Don’t be rude, kid. I have all your embarrassing childhood pictures and I’m not afraid to use them.”

Dean snorted. He looked down at Mom’s hand, still clasping his softly, and back up to her eyes, which were now watching him with obvious fondness. “You’re not disappointed? I know you wanted another daughter-in-law.”

“C’mere.”

Mom reached around his shoulders, pulling him into a hug. Dean hugged her back, relaxing into her arms and feeling for a moment like that twelve-year-old kid who’d come home after school to find out Dad had bailed on them. Mom had hugged him like that, then, and Dean had known instantly that he’d never have to worry about her leaving.

They parted, both pretending not to see as the other wiped their eyes.

“The only way you could ever disappoint me,” Mom said, “is if you start rooting for the Washington Redskins.”

Dean laughed, shaking his head. “Never gonna happen. Fuck the Redskins.”

“Fuck the Redskins,” Mom agreed solemnly.

*

Cas arrived early afternoon the next day to help get everything ready. Dean’s nerves were already on edge, and Cas seemed to sense it as he pulled Dean in for a sweet, lingering kiss as soon as he’d closed the door behind him.

“Are you okay?”

Dean nodded, a little dazed. “Yeah.” He licked his lips, chasing the lingering taste of Cas’ chapstick. “Let’s just focus on dinner.”

“What are we making?”

I’m making Vietnamese beef stew,” Dean said, leading Cas into the kitchen. “You can’t cook worth a damn, so you’re on chopping board duty.”

“I can make mac and cheese,” Cas protested.

“It doesn’t count if it comes from a box, babe.”

They worked in relative silence, the only sounds the quiet tones of golden oldies from the radio, the chopping of Cas’ knife and the sizzling of the beef cubes on the pan. Dean grabbed himself a bottle of beer, hoping to calm his nerves some.

He wasn’t exactly sure what he was so nervous about. He already knew Mom and Sam accepted him, and no one could dislike Cas so they were bound to get along. Maybe it was just that this was the first time he’d introduced his family to a significant other since Lisa, and look how he’d fucked that up.

He offered a beer to Cas, who turned it down.

“I don’t want to be drunk when I meet your family,” he told Dean primly.

Dean snorted. “It’s one bottle.”

“That’s one too many.”

“Dork,” Dean muttered fondly.

In retaliation, Cas snaked an arm around Dean’s lower back and reached down to pinch his butt.

 

Two hours later, the beef stew was fully cooked, the apartment filled with a heady aroma. Dean had finished his beer a while ago and had been on his way to grab another, when Cas pinned him against the counter next to the stove and offered a better way to calm him down.

They didn’t pull apart for more than the couple of minutes it took Dean to check on the stew until the doorbell rang. Dean nearly jumped at the sound, heart immediately in his throat.

“How do I look?” he asked Cas, nervously running his fingers through his hair, which had to be a mess by now.

“Debauched,” was Cas’ not-at-all comforting answer.

Dean glared at him, pushing him away to go and answer the door. He patted his hair down one more time before grasping the doorknob and swinging the door open. Judging by the twin smirks that appeared on Sam and Eileen’s faces once they saw him, it didn’t do much good.

“Are we interrupting?” Sam asked.

Dean rolled his eyes, stepping aside and letting them in. “Hardy-freaking-har.”

“They’re still in the honeymoon period,” Eileen told Sam wisely, going in for a brief hug from Dean. As she stepped away, she flicked Dean’s collar back into its proper position with a wink. “Don’t act like we weren’t just as obnoxious.”

“Here,” Sam said, dropping a bottle of wine in Dean’s hand. “Now, where are you hiding him?”

Dean frowned, but before he could answer Cas cleared his throat from the kitchen doorway. “Hello. Sam and Eileen, isn’t it?”

He walked into the room, holding his hand out for the two of them to shake. Sam and Eileen both looked a little perplexed by his stiff mannerisms, and Dean could hardly keep the fond smile off his lips. God, his boyfriend was such a dork.

“Yeah,” Sam said, hesitantly grabbing Cas’ hand. “And you’re Cas.”

“Castiel Milton,” Cas clarified. Such a dork. “It’s nice to finally meet you.”

It seemed his nerves had finally caught up with him, since he was acting even more awkward than usual, and Dean couldn’t resist peering over Sam’s shoulder and mouthing, ‘doing great, babe,’ at him. Cas pretended not to see him.

“You too, man,” Sam said.

Eileen shook Cas’ hand too, waiting until he had dropped it to introduce herself by both signing and saying, “I’m Eileen, Sam’s girlfriend. Obviously.”

“Oh,” Cas said. “I’m sorry, I don’t know sign language.”

“Not a problem,” Eileen assured him. “Nice to meet you. Dean has told us so much about you.”

That last part was said with a pointed look at Dean, who had, in fact, not told them anything about Cas other than his gender.

He was, thankfully, saved by the literal bell.

“Answer,” he told Sam. “I gotta hit the head.”

“Sure,” Sam said, with a smarmy grin, because he was a smarmy dick. “Maybe find something to cover that hickey while you’re at it.”

Dean responded with a firm middle finger, before fleeing to the bathroom before Mom got inside. She’d been accepting, but that didn’t mean he wanted her to see him all… what had Cas said? Debauched?

He brushed his hair and washed his face quickly, inspecting his neck for any hickeys (none, of course, because he wasn’t the kind of idiot who would let his boyfriend do that right before a big family dinner).

Dean gave himself another minute just to calm down properly, before going back outside. He felt a little bad for leaving Cas out there by himself, but that didn’t turn out to be a problem. They’d all moved into the living room and Cas sat on the couch next to Mom, already in deep conversation with her. Dean stopped in the doorway, heart feeling so stupidly full of love in that moment, seeing the people he loved the most all gathered in one place and enjoying each other’s company.

Then Mary spotted him. “Come sit down, Dean. I was just telling Castiel about your stint on the wrestling team in junior year. Remember that?” She turned to Cas. “He had at least three posters of Gunner Lawless on his bedroom wall. Honestly, in hindsight I should have been less surprised by you.”

“Yeah, that was a full-on fanboy crush,” Sam agreed with a snicker.

Never mind. Dean hated all these people and was never having them over for dinner again.

 

Despite his family’s compulsion to embarrass him in all situations, dinner turned out better than Dean dared to hope for. Once Cas got past his initial awkwardness, he got on well with everyone. He and Mary even arranged to hit the gym together sometime, because apparently every person Dean loved was a raging masochist.

The only hitch in the evening happened when Sam brought up the possibility of getting together with Cas’ parents.

“We’re not on speaking terms,” Cas said simply, like he was talking about the weather and not half of his family abandoning him because they were raging homophobes. “They cut me out once they found out I was gay.”

There was a long, painful silence. Dean reached for Cas’ hand underneath the table, squeezing it tight, and Cas seemed to realize the terrible revelation he’d just casually dropped.

“But my sister and I do still talk,” he added. “And I’m sure she’d love to meet you.”

The conversation moved on after some awkwardly mumbled condolences. Dean held onto Cas’ hand for a little while longer before letting go, and Cas shot him a grateful smile.

The rest of the evening passed uneventfully and Dean heaved a sigh of relief as he closed the door behind Mom, Sam, and Eileen. He walked back into the kitchen, where Cas was putting away the dishes.

“Leave ‘em,” Dean muttered, tugging on Cas’ hand until he put the dirty dish back down.

Cas smiled, expression unbearably soft, leaning his butt against the table and wrapping both hands around Dean’s lower back. “I liked them.”

“Yeah?” Dean couldn’t hold back his smile if he tried. “They liked you, too.”

“You’re sure?” Cas asked, uncharacteristically bashful.

Dean leaned in, dropping a short kiss on the tip of Cas’ nose. It was quite possibly the single cutesiest thing he’d ever done. “Definitely. You’re a pretty likable guy.”

Cas hummed, absentmindedly letting his hands wander, playing with the hem of Dean’s shirt, cupping his ass.

“Wanna move this to the bedroom?” Dean suggested.

“Here is good,” Cas replied. He looked up into Dean’s eyes, gaze heated. “So, Gunner Lawless.”

Dean groaned. “I’m gonna kill my mother.”

“I haven’t heard of him,” Cas said. “But I’m guessing from the context of our conversation that he is a wrestler. Built, strong. Capable of pinning someone down with ease. Is that your type, Dean?”

Heat was already pooling in Dean’s gut. “You’re my type,” he told Cas.

“Are you saying I’m not strong?”

Before Dean could respond, Cas had flipped their positions, pressing Dean against the table’s edge. Dean’s stomach flipped at the unexpected shift, dick stirring to life in his boxers.

“Are you?” Dean challenged, a thrill going through him as Cas’ eyes darkened at the tease. “I’m not sure I believe you without any proof.”

Cas’ eyes narrowed, and then he was grabbing Dean’s thighs, pushing him up onto the table. Dean flailed momentarily, grabbing Cas’ shoulders to keep his balance and not fall flat on his back, on top of all the dirty dishes and cutlery still littering the table.

“Fuck,” Dean breathed.

Cas grinned. “‘Fuck’ is right. That is precisely what I am going to do, fuck the insolence out of you.”

“That-” Dean choked on his words as Cas grabbed him between the legs, squeezing almost painfully tight before letting go. “That might take more than one session.”

“I’ll be thorough,” Cas promised, now tugging at the buttons and zipper on Dean’s jeans.

“What are you gonna do?” Dean asked, breathless with anticipation.

“I’m going to bend you over this table, and finger and spank you until you’re begging for release. Then I’m going to fuck you.”

It was all said in such matter-of-fact tones, and Dean was helpless to do anything but nod and comply when Cas tugged him back off the table and turned him around. He flushed down to his toes when Cas put a heavy hand on the back of his neck, making him bend over, grinding briefly against Dean’s clad ass. Dean moaned as he felt Cas’ half-hard cock between his cheeks, even through the layers of fabric still between them.

“That’s it,” Cas encouraged, pulling slightly away and reaching between them to yank down Dean’s pants and underwear.

The first slap came as a complete surprise. That was the only reason Dean yelped, and he was sticking by that. The next two came in quick succession, catching each of Dean’s cheeks, and he was pushing into it without even meaning to. It hurt, but not too badly, and every blow seemed to send a jolt right down to Dean’s dick.

Then, Cas was pausing. “I… need to get the lube.”

Dean groaned, raising his head as much as Cas’ hand on his neck allowed and glaring over his shoulder. “Are you kidding me?”

“I’ll be quick. Where is it?”

Dean sighed and slumped against the table. “Nightstand drawer. Hurry.”

Cas gave him another quick slap on the ass, and then he was gone. Dean stayed bent over the table, feeling a little ridiculous being in the position by himself. He glanced backwards, making sure the blinds were pulled shut and that he wasn’t inadvertently giving the neighbors a show.

Cas got back into the kitchen, lube and condom in hand, and glanced in the direction Dean was looking. “Do you want to open them?”

“Too kinky, Cas.”

“You’re probably right,” Cas agreed, and then he was crowding Dean against the table again, rubbing his open palm over Dean’s cheeks before giving them another hard spank. “Maybe later.”

“Maybe never,” Dean argued, biting down on his lip as he got another slap on the ass for his backtalk. “My neighbor’s enough of a perv already.”

Cas hummed, taking his hands off Dean’s body entirely as he opened the lube, but still standing close enough so that Dean could grind back on his crotch. Which he did, despite (or maybe because) of the way his skin burned at the friction.

“I do like having you to myself,” Cas said, trailing between Dean’s cheeks with two lubed fingers. “Spread.”

Dean groaned, moving his feet further apart.

“Lovely, but not what I meant.” Cas leaned down, grabbing a fistful of Dean’s hair and forcing him to raise his head. Dean moaned at the sting in his scalp, his cock now fully hard and leaking. “Now, spread.”

Flushing, Dean reached down and pulled his cheeks apart with both hands. Cas’ fingers found his hole immediately, fingertips rubbing over it a couple of times before dipping inside. Dean hissed at the intrusion, but he stayed still as Cas moved his fingers deeper, already twisting them around.

He let go of Dean’s hair and Dean let his head fall back down against the table with a soft thud. Cas’ fingers were moving confidently, pumping away inside Dean’s hole, just barely grazing past his prostate. Then Cas spanked him again, just as he pressed his fingers deep, and Dean couldn’t hold back a punched-out moan.

Cas kept it up, fucking Dean on his fingers with one hand, spanking his ass and the tops of his thighs with the other, setting an almost ruthless pace and drawing an endless string of gasps and groans from Dean.

By the time Cas was adding a fourth finger, Dean was hard enough to pound nails and despite not being loose enough yet, dying to get fucked already.

“Beg me,” Cas commanded, twisting his fingers inside Dean. “Beg me, and I’ll fuck you.”

And Dean had his pride, but at this moment he couldn’t scrape it together if he tried. “Please, Cas- ah- please…

“Please what?”

“Please, ah-” Dean swallowed, hardly believing what he was about to say, feeling both humiliated by it and turned on beyond belief. “Fuck me, Cas, please.”

At first, he was sure that it wouldn’t be enough, that Cas would make him say it again, and part of him even hoped he would. But Cas took mercy on him, twisting his fingers inside Dean one more time to make sure he was loose enough, before pulling out.

The few seconds it took him to put on the condom felt endless, but then Cas was grabbing Dean’s hip with one hand and using the other to guide himself inside him. He went torturously slow, pushing at first just the head of his dick inside Dean, then pulling it back out, making Dean’s rim tug at his cock.

Cas,” Dean ground out.

“Yes, Dean?”

Dean opened his mouth to respond and Cas picked that moment to grab him by both hips and slam inside him, setting a merciless pace immediately. Dean moaned at finally being filled and fucked the way he wanted, the near painful slam of Cas’ hips against his echoing his earlier spanking.

Cas was fucking him like he’d finally lost control, hard and fast and deep, groaning and panting. Their moans joined the sound of skin slapping against skin and the filthy sound of Cas’ dick plunging in and out of Dean.

They were both close, and when Cas let go of Dean’s hip and reached around him to grab his dick it didn’t take more than a handful of pumps for Dean to come. Cas followed right after, grinding his hips against Dean as he came, pressing his forehead against Dean’s shoulder blade.

For a minute, neither one of them moved, both of them slumped against the table and panting as they tried to catch their breath. Finally, the weight of Cas on top of him became too much and Dean pushed him off.

Cas went, stumbling a little as the effort of fucking Dean so hard had apparently turned his legs to jell-o (nice). Dean straightened and turned around, tugging Cas in for a breathless kiss.

“That was nice,” Cas said when they broke apart.

Dean’s lips twitched. Only his dork of a boyfriend could fuck someone over the table after a family dinner and call it ‘nice’. No wonder he loved him.

Cas tugged up his pants for him, tucking Dean’s dick back into his underwear, and only then did Dean realize what he’d just thought.

What he’d been thinking the entire evening.

He… loved Cas?