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Third Time's the Charm

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"So you are virgins. Again," Cas says, squinting like this doesn't make any sense. Sam shrugs. It doesn't make any sense to him either. "But a virgin is someone who hasn't had sex," Cas says. "You and Dean have had sex."

Sam shrugs again. "Apparently intent counts in the greater scheme of things. Dean's taken care of his, but I'm stuck with a pesky case of virginity."

"I don't understand what that means." Cas tilts his head in that way that means he doesn't get it but he's trying to, really, really hard.

Sam sighs, wiping his hands down his face. How does he get stuck explaining all the hard stuff to Cas? "In our line of business, virginity is something of a handicap. There are a lot of things out there that feed on virgins, or who can smell them. Dean nearly got eaten when he was thirteen, so he was determined to take care of it as soon as possible – and as soon as I was old enough to get what sex was about, he made sure I took care of it too."

Cas's eyebrows shoot up and Sam waves his hands, shaking his head to get the idea out of it ASAP. "No, no, no! He locked me in the Impala with a girl. She was nice, and willing, but it was awkward and a little traumatizing." He's never been too broken up about it, but Dean's weird fetishization of his own virginity has made Sam think about it more than he normally would. It's just another part of growing up like they did that was all fucked up. He can't really take his newfound virginity too seriously; just thinking about the last two times he lost it makes him cringe.

"Maybe the third time's the charm," Sam says, chuckling.

"For what?" Cas asks.

"Oh," Sam answers, suddenly realizing that explaining means giving Cas way more information than he's particularly comfortable with. "Well." He clears his throat. "My first time was kind of disappointing. And then, if Dean's whole theory about getting your virginity back when your body is rematerialized is right, my second first time was with a prostitute. Or maybe two. That whole soulless time is a little fuzzy."

Cas looks pained but before he can apologize for the hundredth time, Sam interrupts. "I was just joking about my third first time," he says, though he wasn't, not really. He doesn't want to think about the fact that he might not have another meaningful sexual encounter for the rest of his life. "It doesn't really matter."

"Your virginity doesn't really matter?" Cas asks, and Sam rolls his eyes. This is a weird and complicated issue to be tackling with Cas – especially since it's completely moot. Cas isn't a virgin anymore, and technical virginity aside, neither is Sam.

"It's just a human thing. Some people want their first time to be special - you know, with someone they love and all that. Some people wait until they're married." Sam smiles. It's the kind of thing he thinks he might have decided to do – just to piss Dean off – if their childhood had been more normal. "I was just kidding, basically. I never had the chance to decide that for myself, so I thought maybe I could do something special this time."

"Special," Cas says, sipping at his beer. He's never seemed to like it much, but Sam doesn't drink a whole lot else besides beer and water these days, and it didn't occur to him to get soda or whiskey. "So, some sex is more meaningful than other sex." He tilts his head at Sam again. "Why?"

Sam frowns. Trust Cas to ask all the really difficult questions. "Depends on the reason, I guess."

"And what reasons are those?" Cas seems mildly curious about everything; probably because he's never had this sort of discussion before. The only other person he might have asked would've been Dean, but Dean is a twelve-year-old at heart and can't actually talk about things like sex like an adult. Sam will never forget his birds and bees talk, much as he would like to.

"You can have sex for all kinds of reasons," Sam answers, playing with the label on his beer. "For fun, to blow off steam, because you hate each other–" Cas gasps, and Sam would actually love to see Cas's face when he figures out hatesex, "–because you love each other, because you're bored, you know, whatever."

"I hadn't realized it was so varied."

Sam laughs and takes a swig of his beer. "Across humans it is. And for some people, they have sex for all those reasons, and I'm sure a bunch more I've never even thought of." He takes another drink. "Some of us are more selective, though."

He glances at Cas, who looks thoughtful. "You?"

Sam goes back to picking the label on his beer. "Generally, yeah. Sex means something different to me than it does to... well, Dean, for example."

~~~

"You have sex with your brain," Cas says, leaning forward on the chair with his hands tucked between his knees, the beer he's nursing dangling from his fingers.

"Not exactly," Sam says, struggling for a way to get through to Cas that won't lead into another forty minute tangent about the concept of romantic love. "I mean that sex can have a mental component – and an emotional one. That doesn't mean that your actual brain is doing anything other than thinking."

"Sex is not simply physical, then?"

"Not always," Sam answers, wondering if there is anything he can give Cas a straight answer to. "It depends on who's involved. Dean can have sex with any remotely attractive woman who gives him a second glance."

Sam smiles at Cas's nod of agreement.

"That's just Dean. As long as they both have a good time, everything's fine. And that's one way of doing it – one that's worked pretty well for Dean over the years."

"But it's not your way," Cas says, leaning back in his chair and bringing the beer up for a sip.

Sam takes a deep breath and lets it out slowly. "No, but my way isn't necessarily better. It's just my way."

"I'd be interested to hear about your way." Cas takes another sip of beer, setting it down on the table and giving the bottle a sidelong look like it's personally insulted him.

Sam shrugs. "I'm not generally attracted to women unless I talk to them first. I may think they're pretty, but I have to feel connected to them somehow to be interested in having sex with them, and that means conversation to get to know them better."

"So you're saying having sex without mental stimulation is less satisfactory?" Cas asks.

Sam hesitates. He's never really said any of this out loud – Dean would just mock him, call him Samantha, but he's not really ashamed of being a romantic. He thinks Dean is at heart, too – Dean's just better at burying what he wants under his sense of duty.

"And emotional. I think I find intelligence attractive, but there has to be some kind of emotional connection."

"I see," Cas says, but he doesn't look like he sees. He looks slightly confused. "And the sex itself – the emotional and mental components are important?"

"Well, yeah," Sam says. "Sex is better if I'm emotionally invested in the other person, and that usually means that I take the time to learn what they'd like. I like figuring out what makes people tick."

Cas looks alarmed and Sam puts his hands out, a silent "what?" to see if Cas wants to talk about it.

"Human beings tick?" he asks. "I've never noticed any ticking."

Sam laughs and takes a long drink of his beer. "No, Cas, it means how they work – what turns them on."

At Cas's further-widening eyes, Sam adds, "No, there's no on/off switch. It's a phrase. To be 'turned on' means to be aroused."

"Oh," Cas says, nodding solemnly. "I understand."

Sam highly doubts it.

~~~

"And you don't have sex with blood-related members of your family," Cas says, because apparently repeating everything Sam says is the way he learns the basic rules of human copulation.

"It's a very strong cultural taboo," Sam explains, shifting over to the bed because the long drive and the beer have suddenly gotten to him and he's getting tired. "It's probably based on the fear of having a deformed child."

"And this is why you and Dean have never had sex."

Sam opens his mouth to protest and doesn't even know where to start. He throws up his hands. "Dean and I have never thought about having sex."

"Because of the culturally-ingrained taboo." Cas takes another sip of his beer and valiantly keeps his face neutral.

"Because we just haven't," Sam insists. "It's not something that's ever crossed our minds."

"So you don't know how attractive Dean is." Cas looks him up and down. "And you don't think Dean knows how attractive you are."

"I… what?" Sam asks. He understands Dean is attractive because women never stop flirting with him – and men too, for that matter. He doesn't think Dean has ever thought about how attractive Sam is, except in a sideways sort of way, back when he used to go out of his way to get Sam laid.

Cas doesn't repeat his statement; he seems to understand that it takes a while for Sam to process the more difficult questions and find a way to explain that will satisfy him.

"I understand that Dean is attractive because people have stared at him since he was a teenager, but he's never been attractive to me personally," Sam says. Cas seems to accept that answer, so Sam pushes on. "I don't think he's ever thought about whether or not I might be attractive to women, honestly."

"Why to women?" Cas asks, and Sam groans and flops back on the bed.

~~~

"Some people like men, some people like women, and some people like both. Everybody's different."

Cas tilts his head. "Some people aren't sexually attracted to anyone," he says, like he knows this for certain.

Sam shrugs. "I suppose so. Though I've never personally known anyone like that."

Cas lifts his chin. "Jimmy was like that."

"But…" Sam doesn't know if it's hard for Cas to talk about Jimmy or not; he wants to ask but he doesn't want to be intrusive.

"But?" Cas prompts.

"But he was married," Sam says in a rush. "He had a daughter."

Cas nods. "It was his duty. He did it because it was expected of him, and because he loved his wife."

Sam wonders if that's part of the reason Cas has never showed an interest in sex, the way Gabriel clearly had. This is the sort of thing he'd be interested in discussing with Cas, but he doesn't know if it'd be uncomfortable or not. He's shared stories about Jess and Amelia, but they are distant, warm memories now, not open wounds that he still has to deal with every day.

"You have something you'd like to ask?" Cas smiles at him encouragingly.

Sam thinks about that for a second, taking the warm beer out of Cas's hands and switching it out for a cold one. He makes fewer faces when the beer is cold. "Well," he hedges, and then decides to go for it. "You said you liked sex with April. But Jimmy didn't enjoy sex, and that's his body. So is sex somehow related to… your…" There is no word for what Cas has – it's not a soul, and grace isn't the same thing as a soul either, not that he has that right now. "…consciousness?"

Cas tilts his head, thinking hard for a moment and answering with the same earnestness he's displayed all evening. "I believe so. Jimmy's memories indicate the physical sensations were pleasant, when he had them. Even so, he would have avoided the physical contact if he could have done so without upsetting his wife."

Cas looks sad, but Sam can't untangle that without asking more questions and he thinks that might make it worse. He takes a deep breath and tries to think of anything to change the subject.

~~~

"Friends can't have sex? Is this some kind of rule?"

Sam closes his eyes. Why is this his life? "No," he says, sighing. "There aren't any universal rules. A lot of people have their own ethical codes, though." He gets up to set his empty on the table and takes another beer. He doesn't normally drink more than one, but serious conversations with Cas require copious amounts of alcohol. "And yes, friends can have sex, but most don't."

"Why?" Cas asks. "It seems like a wonderful way to celebrate a friendship."

"Lots of reasons," Sam says. The prevaricating is really starting to annoy him. "Maybe there's no sexual attraction between them, or they worry if it's bad they won't be able to face each other anymore, or if it's good, maybe the friendship will shift into something else, or... who knows, really?"

"I see," Cas says. "Well, I understand the lack of sexual attraction, but the other two seem like perhaps it's not a very good friendship, if those are concerns."

"Cas," Sam says, aghast at himself when he hears Dean's I'm-cutting-you-off-because-this-is-too-much-bother snarl. He twists the cap off his beer and flicks it at Cas. Cas gives him half of a smile, one corner of his mouth curling up for just a second.

Sam takes a deep breath and starts again. "Sex and friendship are both complicated. Trying to mix them… There are just a lot of variables involved."

~~~

"We should have intercourse," Cas says, standing and stretching, arms overhead. He rolls his head on his neck.

"Excuse me?" Sam answers, because he can't have just received the most matter-of-fact proposition of his life from someone who couldn't be bothered to stop stretching and make eye contact.

"You indicated you don't wish to be a virgin anymore, we are friends so it wouldn't be 'meaningless'" – Cas actually uses the air quotes – "and I think we would both enjoy it."

Sam is at a loss for words, something that doesn't happen very often and is always awkward with Cas. "I…" He coughs.

"Unless there is a problem with the attraction part. You aren't attracted to me?"

Sam coughs again, harder this time. "Not you specifically, Cas. I just… men aren't really my thing."

"Oh," Cas says, sounding a little put out. "I didn't realize that would be a problem."

"It's not a problem," Sam says, because jeez, the last thing he wants is for Cas to think he's some kind of homophobic asshole, "it's just not the way I'm wired."

"But I thought you said sex had a mental component. Surely you're creative enough to overcome that part of it."

Sam gulps the rest of his beer and sets the empty on the nightstand. Cas does not make this sort of thing easy. "I don't really see any reason to," he says. "I'm sure I'll get rid of it in due time."

Cas tilts his head, and for a second, Sam expects him to just make a confused face and drop it. But that would be too easy, and besides, Cas took stubbornness lessons from him and Dean. He finishes his beer (three long swallows that nearly make him fall over backwards) and says, "But you said it was a liability. And I am here and willing. Your only argument is that I'm the wrong gender. I fail to see that as a significant issue, as I have spent time in male and female bodies. In essence, I am still genderless."

"Okay, that's not helping," Sam says, rubbing his temples because now he's picturing Cas with Ken doll-type junk, and that's just messed up. "Seriously, Cas, we've been talking about sex for nearly two hours and I haven't even had the slightest interest. Dean would've had three orgasms by now. Clearly this is a problem."

"We have only been intellectually talking about sex. There is a difference between a discussion and a seduction."

Sam might be able to take that seriously if Cas wasn't still in his blue Gas-N-Sip vest and standing too close to the kitchenette table because he's probably a little wobbly from his two beers. "No offense, Cas, but I have my doubts about your seduction techniques."

Cas straightens and walks directly to the bed. It's purposeful, that walk, and it reminds him of what Cas was like as an angel. Very few people intimidate him, but Cas has done it on several occasions, and seeing him like this makes a shiver run down Sam's spine.

"Sam," Cas says, and Sam looks up at him automatically, a weird hopeful feeling rising in his chest like it had when he first met the angel, when he was so desperate for Castiel's approval, despite everything that was wrong with him, the demon blood, his addiction, his inherent weakness.

"Yes, Cas?" he answers, hearing the anticipation loud and clear in his voice. He doesn't know if Cas can sense it; he would have known, if he was still an angel.

"Let me do this for you," Cas says, crouching down so he is on Sam's level. It's something he never would have done as an angel, make concessions so Sam might feel more comfortable. Something about it makes Sam sad – and yet makes him want to give Cas what he wants, too, like it might be a gift for both of them.

Sam nods jerkily. "Okay," he says, and immediately questions crowd his mind. What counts as sex between two guys? Who's sticking what where? What about protection?

He has to ask the last question – he doesn't carry condoms on him all the time like Dean does. "Um," he starts, wondering if maybe this will be the end of the whole situation because going out to buy condoms is going to break whatever minimal forward momentum they have going on here.

"Yes?" Cas asks, putting a hand on Sam's knee. It's strangely comforting.

"I don't suppose Dean gave you the birds and bees talk before you left the bunker?" He doubts it – Cas left in a hurry (probably some idiot thing Dean said) and Dean hadn't been inclined to talk him out of it. Sam's been carefully avoiding the whole subject.

"Why would Dean want to talk to me about winged animals and insects?"

Sam nods. So the conversation continues. He's not sure if he's glad for the reprieve or not. "Well, remember when Dean asked if you used protection with April?"

"Yes," Cas answers. "I thought it was a bit strange at the time, but Dean does always carry a weapon."

"Not that kind of protection," Sam says, glancing away from Cas. This whole situation is weird and he's not embarrassed, not really, but it's difficult to keep eye contact when the discussion is no longer strictly about hypothetical sex. "When two people have sex, they need to have a barrier between them, to avoid pregnancy and spreading disease."

When he looks back at Cas, he is blinking his incomprehension. "I thought only females of your species could get pregnant."

Sam nods once, tightly. He doesn't say, Our species, Cas.

"This body does not have any diseases. Do you have diseases?"

Sam wrinkles his forehead. He can't even comprehend how much he doesn't want to discuss this. It occurs to him that if this is supposed to be his "special" virginity-losing sex, it's starting out pretty badly. "I don't think so," Sam says. "I haven't been tested in a while, but I haven't had sex in a while, either. Not to mention–"

He doesn't want to talk smack about the girl that reaper was riding, but there's nothing for it. He sighs deeply. "You don't know if April had any that she might have passed on to you."

Cas lowers his gaze; embarrassed, or chastened, maybe. "I see."

Sam huffs out a laugh. Cas looks up at him, curious, and Sam just shrugs. What had he been expecting, Cas to take him forcefully like some fainting maiden?

"It seems I need to make some preparations," Cas says. "Will you change your mind if you have to wait?"

Sam thinks about that for a minute, knowing the patented Winchester way would be to wait until Cas went out and then pack up and leave the state. Even as nervous as he is about the whole situation, though, he doesn't want to do that to Cas.

He shakes his head. "I'll be here."

Cas smiles, a surprising look that Sam hasn't seen in a really long time. It suits him, oddly, and makes Sam feel better about this whole weird situation. "Good," Cas says, surging forward to kiss Sam on the side of the mouth and then standing.

It wasn't enough of a kiss for Sam to even respond to, but it'd been determined and sweet and maybe this won't be quite as awkward as he thinks.

"I can run out and pick up the condoms," Sam offers, because he knows they're going to want lube, and he doesn't actually want to have that discussion. Better to just figure it out in the heat of the moment. Assuming there is any heat, when they get to the moment.

Cas's face pinches up unhappily. It could be anything. He might be thinking Sam will take off; he might feel guilty because he has no money to buy supplies; he might feel stupid because he doesn't know what a condom is. Whatever it is, Cas gets over it and nods.

"Anything else you want?" Sam asks, throwing on his jacket and snatching the keys off the table. He thinks maybe a request for more alcohol might be forthcoming, or maybe food – Cas had eaten like a bear going into hibernation at dinner.

"Just for you not to change your mind," Cas says. His determination is weirdly charming.

Sam smiles. "My word is good," he says. "I'll be back in a few." He looks Cas up and down. "If you could maybe get out of that vest, it wouldn't hurt." Cas looks down at his vest like it might bite him. "Oh, hey," Sam says, remembering what Dean said about Cas not having a place of his own, "You could use the shower if you wanted."

Cas looks sad again. Sam takes a deep breath, trying to make this the least uncomfortable he can. "I didn't mean anything by it," he says. "Dean told me about–"

Cas puts up a hand to cut him off. "Thank you," he says, making a shooing motion at Sam. It's the most human thing he's ever seen Cas do. "And actually, coffee might be nice, if you don't mind. I've become quite fond of it, working at the gas station."

Sam nods once, the awkwardness settling back in with a vengeance. "Okay," he says. "I won't be too long."

~~~

"Welcome to Dylan Drug!"

The woman behind the counter at the mom and pop drug store greets him heartily as he comes in. He should have known that the only drug store in driving distance wouldn't be a nicely anonymous CVS or Rite Aid.

He gives her a quick smile, one he's not really feeling since he's going to be walking out in a few minutes with condoms and lube and she probably won't be smiling at him then. He sighs and starts searching the aisles. After he goes through half of them, he starts worrying that maybe they don't carry that sort of thing around here, maybe they're all God-fearing citizens who don't have sex until they're married and then have lots of babies. He finally finds the section, tucked away in the far corner of the store, and there are exactly three types of condoms and the choice of Vaseline or K-Y Jelly for lube. He grabs the K-Y and a box of each kind of condom because none of them look particularly inspiring.

He's tempted to grab a handful of other stuff to see if he can get the sex stuff through without too much comment, but the stuff in his hands has made the situation terrifyingly real, and if he buys snacks and socks and cough syrup he might just get in the car and leave. He takes a deep breath and braves the lady at the counter.

She blushes when she sees what he's got in his hands, but she smiles at him a little. "Hoping to get lucky?" she asks, sounding scandalized.

"More of a sure thing," he says, handing her a few twenties.

~~~

Sam comes into the hotel room the same way he always comes into a hotel room. Alert for possible signs of danger, and yet not really expecting anything unusual. Seeing Cas in just jeans, leaning over to towel dry his hair, is about as unusual as it gets.

The door drifts mostly shut as Sam stands, transfixed, looking at the ridge of Cas's spine, a tiny mountain range down the middle of his back. Before Sam even realizes what he's doing, he's moved over to brush his hand over the bumps, his fingers juddering from one to the next as his hand travels up Cas's back.

Cas shudders when Sam reaches the point between his shoulder blades, and just like that, Sam's completely on board with this whole crazy idea. Not just agreeing because he wants to please Cas or because it's a good idea to get rid of his technical virginity, but because he wants to trace his hands over every inch of Cas's skin, figure out what will drive him crazy, and then take him apart piece by piece.

Cas straightens up and turns to look at Sam, an interesting mix of emotions in his eyes. "Sam."

The ghost of a smile crosses Sam's face, but this isn't really the time, and he doesn't want to lose the moment. "Yeah," he says, reeling Cas in by the towel around his neck. The kiss is a little awkward – who knew Cas was a pushy kind of kisser? – but they work it out, trading off between leading and following, Cas's hands grabbing at Sam's belt loops to pull him closer. Sam gives up his hold on the towel to pull his jacket off and start unbuttoning his shirt.

A singsong voice interrupts, drawing their attention to the door that's just slightly ajar. "Knock knock, you left your door open!"

A woman pokes her head around the door, mouth open like she's about to say something else. She immediately turns bright red and whatever she was going to say turns into: "I'll just close this for you, then." True to her word, she pops out as quickly as she popped in, closing the door with a soft click.

Sam hangs his head, annoyed at the way his life seems to be a constant flow of interruptions just when things get good. Cas looks a little sheepish, like he hadn't exactly expected things to go down that way. Sam rolls his eyes, picks up the bag of condoms and lube from where it's sitting on the table next to Cas's coffee, and empties its contents on the crappy nightstand. He takes the time to open the boxes of condoms and pull one of each out; trying to mess with that in the middle of things would be more of a mood-killer than Ms. Overly-Good-Neighbor.

When he turns around, Cas is walking out of the bathroom, shoulders free of the towel he'd been using. He looks strangely boyish in bare feet and jeans, standing with his arms at his sides. It's weird – Sam's nearly twice as broad as Cas and he has a hard time standing around with his shirt off, always wanting to cross his arms over his chest. Cas's lack of modesty makes him smile, and he kicks his shoes off before sitting down on the end of the bed. "C'mere."

Cas approaches the bed slowly, probably waiting for some direction from Sam. When he gets close enough, Sam drags him closer with two fingers tucked inside the waistband of his jeans, pulling him in between Sam's spread legs. Cas is taller than him like this, and Sam tips his head back, grinning, waiting for Cas to get the picture and lean down enough to kiss him.

Cas stares down at him a long time, and Sam does his best to meet Cas's gaze without looking away. His stare is just as penetrating as it was when he was an angel, but there's a warmth to it now that Sam's never seen, at least not leveled at himself.

Cas reaches out and puts a hand in Sam's hair. It's strange; no one has ever done that without malicious intent before. Sam has to control the urge to pull away. It's only trust in Cas that keeps him in check. Sam lowers his hands to the bed and grips it tightly.

Finally, Cas leans down and kisses him, taking the lead by fisting his hands in Sam's hair so he can't really move his head. There's something thrilling about letting someone else take charge, and Cas isn't shy or awkward any more – he's curious and unabashed, like he wants to try everything right now.

They kiss for a while before Cas pulls back. Sam cracks a smile; he's enjoying Cas satisfying his curiosity, and when Cas gently turns Sam's head to the side so he can kiss his way along Sam's cheekbone and then down to the corner of his jaw, a flood of strange emotions washes over him. He's never been treated like this before, and it makes him feel… cherished. The thought that he is unworthy of Cas's attention, even as a human, bubbles up and he chokes on it, closing his eyes against Cas's tenderness.

"Cas," he whispers, a half-question that he's afraid to ask.

"Hmm?" Cas asks, pulling away to look Sam in the eyes.

Sam has a hard time meeting Cas's gaze this time. This isn't what he thought it would be, and suddenly he's not sure he's ready for it. There's too much history between him and Cas, and he doesn't know if he can deal with Cas's hands telling him things he will never be able believe about himself. "Don't…"

Cas tilts his head, curious. "Don't what, Sam?"

His hands are still in Sam's hair, the fingertips of his left cradling the back of Sam's skull and giving him goosebumps. "Don't…"

Don't treat me like I'm something precious. Don't pretend I'm worth something. Don't make me forget what I am, what I've done.

"Just… don't."

Cas smiles a little, one corner of his mouth lifting. "But I want to," he says, tilting Sam's head back and biting the corner of his jaw, something that makes Sam's eyes flutter closed again. Cas gently tilts Sam's head even further and Sam can feel the way Cas shifts his grip to lift the hair off Sam's neck.

Cas bites Sam's neck, behind his ear, near his hairline, and Sam's eyes roll back in his head. Monsters seem to think his neck is something special – he's had more hands around his neck than he can count – so he normally hates people touching him there. Cas seems to be the exception to every rule, though, because for someone he never fully trusted as an angel, Sam trusts him with everything now, and the way he's sucking on Sam's tendon is oddly exciting.

A strange thought occurs to Sam and he voices it before he can overthink it. "Where did you learn how to do this?"

Cas laughs softly, his breath ruffling Sam's hair. "I didn’t," he says softly. "I'm just doing whatever I feel like."

Sam remembers the feeling of his fingers going up Cas's spine, thinking about how he wanted to figure out everything that makes Cas shudder and he realizes Cas has stolen his only good move. He's always the one that figures out what his partner wants, enjoying himself more when he gets them off first.

His brain comes back online and he raises his hands to Cas's waist, one on either side, his thumbs dipping in under the waistband of Cas's jeans. Cas stutters to a halt, letting out a harsh breath against Sam's neck.

"What are you doing?" Cas asks, and Sam can't help his smirk.

"Whatever I feel like."

Sam moves his hands inward, tracing the line of the jeans, his smirk deepening as he feels Cas's skin tremble under his hands. He dips one thumb into Cas's belly button and feels the tremors take over Cas's whole body.

"I don't understand," Cas says. "That feels good and bad at the same time."

"I think you're a little ticklish," Sam says, giving Cas a reprieve by unbuttoning his jeans and pushing them down his legs, leaving his boxers sitting low on his hips. "Sometimes the signals get crossed on the way to the brain."

He puts his hands back on Cas, thumbs settling on the hollows of his hipbones with a little more pressure. "How's that?"

Cas swallows and nods, staring down at Sam's hands. Cas's fingers loosen their grip on Sam's skull. This, Sam can work with. He leans forward to kiss Cas's stomach, wanting to feel Cas's skin tremble under his lips.

He barely gets to do more than taste, though, before Cas grabs his hands, squeezes, and drops to his knees. His fingers are on the last few buttons of Sam's shirt, and once he gets them undone, he sneaks his hands under the shoulders and slides it down off Sam's arms. Sam obliges, freeing his right arm before it can get trapped in the shirt and then dropping it off the bed from his left. Cas lifts the hem of his t-shirt, licking a stripe up Sam's chest as he pushes it up.

Impatient, Sam grabs the shirt and pulls it off, planning to pull Cas up for a kiss, but stopping as Cas dips his fingers under Sam's waistband, struggling with the button on Sam's jeans. Sam's sure Cas has no idea how sensitive he is, the entire cradle of his hips one huge erogenous zone, so he just sits still, breathing shallowly while Cas fumbles around with his zipper.

"Cas," he growls after a minute of Cas not being able to get his hands coordinated enough to do any good, "just let me." He stands up and strips, taking his shorts down with his jeans, rolling his socks down on the way. When he finishes with a huff he feels a little stupid – he's standing naked in front of the only person in the world he trusts as much as his brother, and Cas is staring at him like he's never actually seen a naked man before. Which, Sam realizes, is an actual possibility.

"Beautiful," Cas says, and Sam might be embarrassed to be called that by anyone else, but with Cas, it's like he's saying the sky is blue.

Cas's own body is different than his – it's the body of a normal man, not someone that hunts monsters for a living. Skinnier than Sam would've thought, but Cas has probably been losing weight since he became human. Sam vows to make sure Cas has enough to eat before he leaves for the bunker.

"Here," Sam says, sitting back down on the bed and pulling Cas in close. He slips his hands under the waistband of Cas's boxers, pulling them down so they're back on equal footing. Cas's hips jut out and Sam wonders if, as an angel, Cas's body might have been a little softer, if he would have had a little more body fat.

He leans forward and licks Cas's hip, earning him Cas's sucked-in breath, which is instantly recognizable as a good thing. Sam keeps at it, biting the bone of Cas's hip, feeling Cas's dick brush his cheek and working up the courage to put his mouth on it.

Cas's breath hitches as Sam explores his body, but it's the only sound he makes, no obvious moans of pleasure. Sam's not sure what to make of it but he keeps going, finally taking Cas's dick in his mouth and feeling satisfied when he gets a breathy moan.

He's less satisfied when Cas can't quite keep his feet and smashes his stomach into Sam's face. Sam pulls off with a squawk of surprise. "Sorry," Cas says, and that's enough for Sam, this is finally moving and he wants to keep the momentum going so he reaches for Cas, going for his hip and getting his shoulder instead because Cas drops to his knees without any warning, a loud thunk in the room that makes Sam flinch.

"I want to try that," Cas says, pushing Sam's knees apart and crawling between them, shoving Sam's shoulders, making him lean back.

"Wait," Sam says, but Cas isn't particularly patient on the best of days, so he's already got his hands on Sam's hips before Sam can finish the word, and Cas sucks Sam's dick into his mouth before Sam can think of anything else to say. Sam's eyes slam shut of their own accord.

"Oh, fuck, Cas," Sam says, because he learned early on to use his words, and while he's pretty fluent in translating moans into something approaching meaningful communication, most people don't get the nuances, and Cas isn't likely to be able to interpret them at all.

Cas hums, his thumbs running up and down Sam's hips like he's trying to make Sam crazy, and that's enough for Sam to remember himself.

"No," Sam says, because he's the one in charge here, he's the one that's going to make Cas writhe and forget his own name, and he shoves Cas off him roughly.

"Did I do something wrong?" Cas asks, surprise and concern both obvious in his voice.

"No, Cas," Sam says, taking a deep breath and sighing it out. "I just want to…" He rubs a hand down his face. He doesn't mind talking about sex, but not in the middle of it. He sighs again. Most likely, this is just the way it's going to be with Cas. "I want to spend some time figuring out what you like, feeling your skin. I like doing that."

"Oh," Cas says, looking thoughtful. He's on his knees in front of Sam, looking over Sam's body like he's cataloging it. "I like doing that too."

Sam laughs. Of course he does.

"Can't we do it at the same time?" Cas asks, a completely innocent question that stops Sam's thought process in its tracks. That's just not the way sex has worked for him. It's about getting your partner off first. It stuns him that he hasn't run into anyone who is similar to him in this way before. He thinks about it, tries to come up with some way they can both satisfy their curiosity at the same time.

"Sixty-nine?" Sam asks. He hasn't done that since college, and it was a disaster – he couldn't concentrate on the girl enough to get her off before he came all over her.

"The sexual positions have numbers?" Cas asks, dumbfounded. "Is there some kind of manual?"

Sam falls back on the bed, laughing. This is the best idea Cas has ever had. It's weird sex, but it's interesting and fun and funny, and Cas is a treat. "No, Cas, it's just a name for the position. Because that's what it looks like."

He raises his head, but he can't really see Cas over his own body, and he looks down at his dick, still interested in the proceedings, despite the stuttering start-and-stop nature of things. "Come up here," Sam says. "Lie next to me."

Cas does as he says, lying on his side, feet still on the floor, so his head is a few inches lower than Sam's. He traces a finger over Sam's ribs and leans in for a kiss, a quick brush of his lips on Sam's shoulder. Sam smiles, and Cas smiles too, his finger dipping lower, about to hit Sam's hipbone.

"Hang on," Sam says. He debates explaining to Cas how they have to move, but then decides it's easier for him to just pick up his legs and swing them around. He has to keep his knees bent, but he rolls onto his side and Cas's hip is right there, a couple of inches away from Sam's mouth. He leans in and licks it, getting up on his elbow to move across Cas's skin. He twists at the waist so his chest is on Cas's stomach, Cas's dick staring him right in the face.

Sam's taller than Cas, mostly in the leg but some in the torso, too, so when he gets on his knees, one on either side of Cas's head, caging him in with Sam's entire body, Cas can't reach Sam with his mouth. Sam smirks, glad Cas can't see his face in this position, and sucks Cas in – so much easier like this. Cas moans this time, and finally Sam feels like he has a hold of the situation, like he can give Cas what he wants and not get distracted.

"Sam," Cas says, and Sam can hear frustration in it, but he can hear more than that, too, so he keeps working on his cocksucking technique, which he's surprisingly game for. Cas squirms underneath him and mouths wetly at his thighs, which works well enough to keep Sam's dick interested in the proceedings.

"Please, Sam," Cas says, and there's a tremble in his voice. Sam stops what he's doing long enough to look at Cas, where he's raising his head to try and get Sam's dick in his mouth. He can't reach, but he looks really desperate, licking his lips obsessively as he strains upward.

That's enough to put Sam right on the edge, so when Cas brings his hands up to spread Sam's knees apart, Sam goes with it, the stretch in his thighs worth the look of bliss that comes across Cas's face as he puts his mouth on Sam, even though he can only get the very tip in his mouth. Sam bucks his hips up, pulling his dick out of Cas's mouth, but Cas gets greedy, raising his head and capturing the tip again for just a moment, until his neck tires and he has to release it.

The sensation is overwhelming – watching Cas's mouth eagerly await his dick and then slipping into the soft heat, only to pull it out again… Sam rips his gaze away and takes Cas in his mouth, just hoping he can hold out until Cas comes.

Cas raises his hips as Sam's mouth slides down him, and Sam can hear and feel him moaning around the tip of Sam's dick. That makes it even better, Cas suckling desperately at the tip because he can't get any more and he clearly wants to – Sam's orgasm hits him hard and he doesn't have time to do more than pull his hips back so he doesn't come in Cas's mouth. He makes a mess all over Cas's chest, and he doesn't know how, but when he pulls off to take a look, Cas comes, stripes everywhere, on Sam's face and in his hair, and then more into the come already pooling on his belly.

As Sam rolls off of Cas and onto his side, he can't help laughing. The last time he laughed during sex was with Jess. They were tipsy and stupid and messy, and it was just funny. Sex with everyone since her has always been sort of mysterious, dangerous, or just plain serious and definitely nothing to laugh about. He smiles at Cas, wiping a hand through his hair to see how bad the damage is. Not too bad, just one streak that's a continuation of the one on his face. "That was fun," Sam says. "Great idea, Cas."

Cas beams at him, smiling uncomplicatedly, which is something Sam has never seen. It's a good look on Cas. He hopes Cas actually gets into being a human – there's so much that Sam thinks he will really love about it if he does.

"Do you think that was enough to take care of your virginity?" Cas asks, and Sam glances over at the untouched boxes of condoms and tube of KY on the nightstand.

"Well," Sam says, grinning, "Maybe we should try a few more things. Just in case."

~~~