So, I kind of loved the episode Free To Be You And Me, just because of the amount of focus it put on Cas and Dean's relationship. It's one of those times that really focuses on the banter between them but also brings the emotional connection to the surface. And then of course, Castiel is just hilariously innocent with some stuff, despite being over a thousand years old, and so I had to write this fic. Because, seriously, what made Dean decide it would be a great idea for him to be the one to make Cas lose his virginity?

"You have been with a woman before, right? Or an angel, at least?"-Dean Winchester, s5, ep03, "Free To Be You And Me"

OK, it's not like Dean Winchester's the kind of guy who sits around thinking about angel's virginities on a regular basis or anything like that, but he has to admit hearing that Cas has never got any action shouldn't really surprise him as much as it does.

Hell, just looking at him, sitting rigid, ramrod-backed in that chair, with that pissed-off look on his face, his lips all pursed, like Dean's just knotted his panties for him-OK, enough with that image-and that little bitten-out phrase I never had occasion, OK? would be enough to tell you the guy's wound up tighter than your average jack-in-the-box.

(And Dean's really got to stop with the springing up and loose imagery.)

But yeah, it's not a surprise. It's just-he'd never really thought about whether Cas was-into that. He's never really seen Cas check any chicks out down here, but then maybe he'd kind of assumed that angels were above that kind of thing, being all righteous-path and shit. But then again, Anna hadn't been.

Dean thought of the backseat of the Impala. Anna definitely hadn't been.

But then, Cas was different. At first, Dean had just assumed the whole closed-face, I'm-a-good-soldier, he's-not-on-any-flatbread-and-no-I-don't-know-why-that-was-funny-Dean-why-do-you-keep-asking schtick was just an angel thing-get to be a warrior of God, lose your sense of humour. But OK, while the rest of them were still a bunch of humourless dicks, most of them had some idea that sarcasm actually existed. Cas still made that weird I-don't-understand-Dean face whenever Dean said "Oh, freaking great" if the Impala stalled or the motel room cable cut out or half his burger fell to bits in his hands.

So, OK, maybe it was a Cas thing, not an angel thing. Maybe angel chicks weren't into the whole my-sense-of-humour-is-faulty thing. Maybe Cas's angel form just wasn't the salt to their pepper.

Whatever Cas's angel form looked like.

But either way, the way Cas is glaring away from him kind of reinforces the reason Dean thanks God every night for the Playboy channel. If this is what never getting laid reduces you to-specifically, reduces a however-many-decades-old angel to-Dean's pretty glad he got rid of that revirginized problem early on.

(Did Cas restore his virginity? Weird thought.)

Anyway, to get back to the main problem, this could be Cas's last night on Earth and at this rate, the dude's going to go out thinking the best thing about human pleasures or whatever he wants to call them are the occasional swig of beer or taste of fries he's had from Dean's plate (OK, he seems to kind of like the TV, given by the way that grin breaks out every time he gets one of the jokes on whatever sitcom re-run he's watching. Cas doesn't often grin like that and whenever it breaks across his face, Dean sometimes busies himself with cleaning a blade or pulling at a shirt, just so Cas doesn't see his own grin. Cas's grins are kind of contagious.)

But whatever, Cas cannot go to his angelic grave thinking that that is the only good stuff about being human. Dean owes it to humanity to give Cas a better representation than that. It's basically a public service he's performing. Painting humanity in the best possible light. Someone should really give him a medal.

So, he grabs his jacket and tells Cas how they're spending his last night on Earth. (OK, maybe he kind of pushes, but come on, it's for Cas's own good. Plus, he really doesn't like thinking about Cas going to any angelic grave and he's going to choose to push that part of the conversation out of his head because they'll find a way to get through it, they always do, and he doesn't know when Cas became one of them but he has, even if he doesn't know it yet.)

Cas is still staring up at him with that confused look, that why is humanity so confusing? look that's kind of puppy-dog adorable and what the hell is Dean thinking, with the words Cas and adorable in the same sentence? But he looks like a kid on his first day of school and so Dean tries to smooth it over with a line about Bert and Ernie (and he does not know why gay cartoon characters are what come into his mind right at that moment) before he basically beckons Cas out the door.

The entire way there, Cas is pretty quiet which gives Dean time to look over at him and wonder just how the hell Cas has gone this long being a virgin and never even seems to have thought about-

OK, Cas has probably thought about it. Maybe. Not that Dean thinks about Cas thinking about it, but...He probably has. Just out of, you know, intellectual curiosity. He bets that's how Cas would put it, some of that old I-am-not-a-lowly-human thing creeping through. I do not understand why you use the term "jerk off", Dean, and no, I have never needed to do so.

And why the hell is he thinking about Cas jerking off?

He glances across at Castiel, just to check angels haven't become telepathic (they weren't the last time Dean looked, but with the world Dean's living in now, he wouldn't be surprised by anything anymore) but Cas is just staring out of the window, his hands knotted together in his lap, chewing at his lip in a way that shouldn't look so human, the same way that that little rub at the neck earlier shouldn't have looked so vulnerable, like this wasn't the same creature that had yanked Dean up out of hell and pinned him against the wall with a hand over his mouth and eyes like fire so cold it burnt.

But in the meantime, Dean takes the chance to just look at Castiel. He guesses that he picked an OK-looking vessel-purely from the point of view of getting some chick interested tonight. But then, that's why Dean's chosen this place-chicks are paid to be interested. Not that he'd think someone'd have to be paid to be interested in Cas. It just-ups their chances.

And anyway, Cas could probably pick some girl up if they were just going on looks. Dark hair, kind of messy, like you could run your fingers through it, big blue eyes, this way of looking at you under the lashes like he could send your ass to hell one minute and ask you for help with a tie the next, and that neck, that weirdly pale skin at his throat that you could probably nibble on-jeez, what was that?

Dean nearly swerves but manages to hold the wheel straight at the last minute. But Cas hasn't missed the sudden tension in his shoulders or the tightness of his jaw and asks something about Dean, is there a problem? and Dean shakes his head, mutters something about his foot slipping on the accelerator, and prays that Castiel doesn't look down and notice the tension somewhere else.

Because, OK, what? Cas is a...friend? It took a while for Dean to think of him as even that. But then obviously, Cas is a friend. Freaking hell, Dean would miss him if he wasn't around. (And that's another reason he really needs tonight to distract them both.) And Dean was just-getting into character, really. Trying to figure out the best chance of getting rid of the whole virginity thing, trying to work out what chicks might like best about Cas, that's all.

At that thought, Dean cheers right up. Yeah, that's all it is. Like that-what do those Hollywood guys call it? Method acting. Yeah. He was just imagining things from the point of view of some girl who might be interested, you know. Just checking things out through another pair of eyes. Nothing in it at all.

But this is just a one-night thing they're looking for, obviously. Though he guesses if Cas stuck around on Earth and wanted some girl for longer, maybe he'd find one. Sure, he'd have to work on sounding a little more human and maybe find some clothes that were more yeah-I-can-pop-down-to-a-bar and less I-just-got-home-from-filing-holy-taxes, but he was pretty sure there'd be a few girls who could get past the whole thing. And Cas wasn't that bad. He could learn sarcasm, some of the time-and anyway, there might be some girls who'd be into that kind of thing, the whole painfully-sincere thing Cas had going on sometimes. Yeah, there were probably plenty that would be. Though he'd have to teach Cas about some honest opinions. If some girl asked him if she looked fat in a shirt and the shirt made her look like she was expecting a few babies in a couple of weeks and Cas opened his mouth, he didn't see the outcome being too good for dating prospects.

Dean just tries to picture Cas's hand wrapped around a girl's, their fingers linked together. It doesn't fit, for some reason. That grin on Cas's face, darting out for anyone else. Maybe that's just because Dean isn't used to the idea. Yeah, that must be it. Obviously.

But Cas would have to be careful. That whole painfully-sincere thing might just drag in the wrong girl, some bitch who could just use him for some kind of easy ride. Cas might have lived for thousands of years, but the guy couldn't do his own tie up, for God's sake. And it might not occur to him when some girl was reaching inside his coat that she was heading for the wallet. (Not that he was sure Cas even knew what money was.)

Dean's teeth ground together and his fingers dug into the wheel. Nah, if Cas ever thought about dating seriously (and honestly, Dean was kind of pleased Cas had never shown any serious interest) they'd have to guide him through it. Because Dean's a good friend like that. He's not going to let Cas get screwed over. That's why they're going here tonight, rather than letting him take his chances in some random bar.

When they get out, there's a bit of a panic moment when Cas works out where they are and tries to step back but Dean catches onto his sleeve, tells him something about experience and living and Come on, Cas, you're like a full-on angel rebel, don't you want to live up to it? Castiel gives him a full-on bitchface but follows him in and he doesn't shove Dean's hand off his coat sleeve, either, and by the time Dean figures out that he hasn't let go, they're nearly at the table and he might as well just keep hold until they sit down.

Cas is still looking like a puppy that's seen two headlights heading straight for its' body when the drinks arrive so Dean tries to give him a pep talk on the way to handle this until Castiel starts babbling about dens of iniquity and Dean rolls his eyes, 'cos honestly, he would give anything to see a hooker's face if she was in a room with Cas and he started on with that kind of speech.

(Except he wouldn't because first, it might be funny but the thought of some girl laughing in Cas's face is enough to make Dean want to throw a glass, and second, why the hell would he want to be in the room with Cas in the process of losing his angel virginity or whatever you'd want to call it? Dean's mind must be fried with what's coming next.)

So a girl heads over and Cas is no help at all, and thank God Dean chose this place because if they were in a bar, he thinks that even the most desperate girl would have figured out she was talking to a guy with less experience than Spongebob Squarepants, and somehow he manages to get Cas walking off with some girl named Chastity (really? Could they have found a better name for this?). Cas is still giving him that puppy-dog look of terror as Dean runs through those last few tips and then he's gone, still looking like he'd prefer to go through another battle with Zachariah than go through with this thing.

Dean orders another drink and tries not to let his thoughts stray towards Cas actually dating anyone. Hell, him and Sam haven't figured out any long-term relationships and Cas would be sticking with them if he was here, so maybe Cas would play by the same rules. But he and Sam play the game of one-night hookups and somehow, Dean can't picture Cas playing by the same rules, not when he looks like he's about to pass out just following a girl called Chastity through a door.

He'd never really thought about Cas with a woman. He'd assumed it had happened before he kicked his brain into gear and realised that it was probably about the last thing that had happened with Cas. He kind of pictures Cas running his hands through her hair with those big blue eyes all wide, like he wasn't quite sure what he was doing. He guesses that Cas would probably let his eyes flicker closed as he was kissed, slowly relaxing into it, the girl's mouth exploring his gently (Dean should have told her to be gentle, he should have, dammnit, still, she seemed to figure out Cas was nervous as hell, maybe she'll take it slow with him-)

Dean gets up and sits at the bar and orders another drink. The girl says something to him and he grins, but he's still thinking of Cas. Does he even know how to kiss? Not like there's an instruction manual, but maybe Dean should have given him some tips. Nah, he'll be fine. Those girls are probably used to guys scoring way higher on the douchebag test than Cas. He'll probably be the most polite customer that Chastity chick's ever had.

And maybe she'll find it sweet, the whole nervous-sincere thing. Maybe she'll teach Cas how to kiss, letting her hands cradle his head, pulling back to let her thumb stroke his bottom lip just gently, and then bending her head to nibble at his throat, just a bit, just enough to make Cas gasp and wonder what this was and why he hadn't-

And that's when Dean realises his jeans are now uncomfortably tented and shit, did he just get hard thinking about Cas?

Nah. Nah, he was just into it. That's all. Obviously. He was just-thinking about it. Good imagination, Winchester. That's all.

But yeah, that girl better be gentle with Cas. But she will be. And yeah, Cas's whole trenchcoat thing-she'll have to be careful with that, given Cas never takes it off. She'll have to slide that tie off from round his neck, rub it against his skin gently, let Cas know it's not going anywhere. Just slide that trenchcoat off his shoulders, let your hand go slowly under his shirt-Dean'd be asking the whole time if Cas was OK with it, obviously, making sure he didn't freak him out because Cas might be whatever-thousand years old but the guy doesn't know what way round an ID goes, for God's sake-he'd be talking to him, the words small breaths against his skin, just gently stroking his hips, telling him it was OK, don't panic, Cas, with a kiss to his neck, and another to his mouth, his mouth warm and soft and inviting Dean in, no need to worry-

Dean nearly knocks his drink over. What the hell? Since when did it become him and Cas? Since when did it become Mills and Boon? It was just thinking about that Chastity chick-and whether Cas was OK-since when did it become about him-kissing-him and Cas!-

And then there's a scream from the corridor.

Long story short, Dean charges out there because there's no way he's leaving Cas in trouble, even if he's currently having some kind of daydream crisis (and first, it wasn't a daydream, it was just a train of thought that went wrong, and second, Cas's voice is way too deep to scream like that) and of course, Cas has screwed this up and it's kind of Dean's fault because he should have warned Cas, of course he should have, gone over things more, but even as they're making a run for it from the bouncers, who've probably been briefed that there's some kind of trenchcoat-wearing stalker in the building, Dean's not that pissed that the whole thing went wrong.

He's kind of worried Cas will be once they get outside-like what if he was really into it and was just trying to do the girl a favour?-but Cas doesn't seem particularly bothered that some chick ran out on him, which reminds Dean that Cas hadn't really wanted to do this in the first place. But Dean's still laughing so hard it hurts, because at least things didn't get too far if Cas really didn't want it, and Cas is grinning at him with that confused look he gets when he knows something's funny, he's just not quite sure what, and next second Dean has his arm around Cas's shoulders and he's telling him he hasn't laughed like that in years, and it slams Dean right between the eyes just how true that it.

Then again, Cas is the only one who makes him laugh like that anyway-duh, he's Cas, the only angel in the world who'd go on about demons to a cop, and need help buttoning a shirt and still be able to smite a city out of existence if he wanted.

He does make Cas tell him absolutely every detail in the Impala, just for the fun of it, mostly, and also to take both their minds off what's coming up, the whole fate that prompted the virginity discussion and the Cas discussion and the Cas-losing-virginity discussion, and Dean really doesn't want to think about anything happening to Cas right now. Doesn't want to think of where this could lead. And he might have just wasted Cas's last night on Earth.

But Cas has still got that smile when he looks at Dean, though he tries to cover it up with a classic bitchface when he catches Dean watching. And Dean, just because, leans over and nudges Cas's mouth into a smile with the edge of his thumb.

Cas pretends to glare but he turns his face away almost immediately and Dean can see the grin that spreads over his whole face reflected in the window. He pretends not to see, just like he pretends that the reason he's grinning is just because he's happy with Cas's company and not because he's also thinking that none of those chicks at that bar tonight made Cas grin the way Dean just has.

The showdown with Raphael goes way better than expected, with Cas trapping the guy in a ring of holy fire and then giving him one of the most truly awesome beatdown lines ever (something about the words my little bitch in Cas's mouth made the hairs on Dean's neck stand up, and OK, maybe brought something else up too, but that was just the situation, obviously) and then they get to leave with their eyes still in their heads and they're back in the Impala and they're driving again.

Cas brings up God and Dean manages to avoid giving his honest opinion (Dean's kind of an expert on dickwad fathers, much as he hates to admit it, and he knows when someone needs to figure shit out for themselves, and this is one of those times, even though it hurts like hell to think of Cas being disappointed and Dean's already planned to forgo the whole no chick-flick moments thing if that happens and Cas ends up a mess and it's Dean's shoulder he needs or whatever) but he tells Cas to go for what he believes. And that's a message that Dean thinks should be put out there more often, if he's honest.

And because he's thinking about Cas and how weird things went tonight, it comes out of his mouth, something about was Cas OK earlier, with that chick, and did anything go wrong, and is he, you know, OK?

Castiel stares at him for a moment and then tells him that he was perfectly safe, he is an angel, and his vessel's physical health has not been endangered in any way whatsoever.

Dean then works his way through the words in his mind, translates them into English and not genius-angel-speak and reworks the question into no, is Cas feeling OK? With what happened? Chastity didn't-you know-offend him? He wasn't-into her?

Castiel pauses as if performing his own translation of Dean-speak and then says that although Chastity was aesthetically pleasing, it did not seem to have much an effect and no, it was not a hardship for him to forgo this act. Did this trouble Dean?

Dean thinks at first Castiel has finally picked up on sarcasm and he's about to toss something back when he catches a glimpse of Castiel's eyes on his, his lips pursed, waiting for an answer, and he realises Cas seriously meant the question. So, he shrugs and says no, of course not, why?

This act-it seemed important to you, Dean. You described it as a rite-of-passage? A fall of the mouth, a downcast flicker of the eyes. I fear I may have-disappointed you by failing to complete it.

And that's when Dean slams on the brakes and yanks the car to the side of the road, yelling something about Jeez, Cas, it's not about me, and Wanted to make sure you weren't disappointed and God, Cas, if I'd known you really didn't want to do it, I wouldn't have-

And Cas stares at him and reaches out to touch his shoulder and just looking at Cas's long fingers pressed against his coat kind of brings back those thoughts from earlier, of sliding Cas's coat off his shoulders, letting his fingers press against Cas's skin.

And Cas says, with that confused head-tilt to the side, Dean, I did not intend to upset you.

Dean catches hold of his wrist then-just so Cas can't blink out on him, obviously-and says no, no you didn't. He just-just wanted to-give you the chance, you know? Maybe he took it too far? You didn't have to if you didn't want to, Cas? Man, didn't mean to make you think you had to do it. You OK, Cas-

But Cas shakes his head and tells Dean that it's forgotten, and Dean grins, and just out of relief, purely out of relief, reaches out and nudges the edge of Cas's mouth with his fingertips. Cas has forgiven him and they're alive and something about that makes this whole night seem pretty much worth it.

Castiel smiles back and then says something about skills with human etiquette being rather difficult for him to master.

I doubt the experience would have been particularly enjoyable for her, Dean he says, and it's so matter-of-fact and serious, that it's Dean who's blushing, not him, and OK, Dean Winchester does not blush, when did this start?

But he shakes his head and then turns and says, without thinking, Look, man, anyone should think they're lucky to be with you, you know? I don't know-I mean, you don't have to be with anyone if you don't want to-but if you're not into that one-night-stand shit, then you don't have to be. And if you know-you wanted anyone-then it should be you know-someone you're happy around. You don't have to impress them all the time, you know? And if it was with them, you'd both enjoy the-experience or whatever-you'd enjoy it even if you didn't get everything right, because you'd like each other, anyway, see?

And that is seriously the most chick-flicky moment Dean Winchester has ever put himself through and what the hell just came out of his mouth? He's about to be exiled to a world of cheesy sitcoms and too-perfect hair and The baby isn't Brad's! lines.

But Castiel just watches him for a long moment, his head tilted to one side and then he says Thank you, Dean. And that small smile's there again and this time, it doesn't fade. It just stays there and Dean doesn't realise he's smiling back, until his heart starts going way too fast to be healthy and somehow, he ends up blurting something like You're too good not to make sure you do the stuff that makes you happy, Cas and oh my God, why is he a soap opera wise next-door neighbour?

(Dean Winchester does not watch soap operas, let it be known, he knows these things from Sam.)

But Cas just smiles and stares back. And neither of them looks away, even as the car idles quietly at the side of the road and the moonlight's washed over half of Cas's face, and Dean can hear his own heartbeat.

He doesn't know what makes him do it, lean in and press his lips so gently to the corner of Cas's mouth. He just hears that small intake of breath as his lips touch Cas's skin, a little rough with stubble, the edge of a jaw against his and then his mouth hovers in front of Castiel's, and Cas's lips are parted, and before Dean can chicken out or have his mind start shrieking at him, he tilts his head and presses his mouth just gently to Castiel's once. Castiel's mouth is warm and soft and even with a bit of stubble scraping his chin and the gear stick digging into his leg, Dean is happy for the moment, just happy, with Cas's mouth warm and open and suddenly, slowly kissing him back the same way.

It's one kiss and it lasts a few moments but when they pull back, Dean's head is spinning and Cas is staring with those big blue eyes and his mouth a little swollen and flushed and Dean feels that little leap in his chest of yay, I was his first kiss. His first proper kiss anyway, thinking of Chastity. His first kiss that he wanted, and there's a difference.

But he bets Chastity didn't get that goofy small smile that Cas gives him now, and those big blue eyes blinking away and the way that Cas sort of darts his gaze to the window and back as if he doesn't know quite what to say.

And neither does Dean so he just says quietly OK?

And Cas looks back and says Better, Dean.

And Dean says Good and before he turns back to the wheel, he lets his thumb brush Cas's cheek for just a moment, a soft touch against warm skin to take with him again.

They don't talk but Castiel stays. He stays in the passenger seat and watches Dean, every time Dean's eyes flicker over to him. They watch each other in the dark as they drive down this road, empty but for the two of them, and it's Cas's eyes Dean holds onto for the rest of the night, Cas's eyes that even as they head back to the motel room, are the closest thing to home Dean holds in his hands.

Cas's smile is the thing that answers the question flickering in Dean's chest and it's the only words they need in the dark.

Hope you enjoyed that! Leave a review if you did! :) xoxo