A/N:

This is a small idea of mine; I started working on when I needed some distraction from my other, more angsty fic I currently work on. It is basically a classic romcom story, and as such it is quite straightforward, but I thoroughly enjoyed writing it. It definitely is something a lot lighter than my other writing.

Fair warning: Dean is a bit of a jerk for the most part, as you would expect in this type of story, but like in your typical romcom it includes an eventual happy ending.

Also, in part the idea of this fic, i.e. Cas being part of a chastity group and Dean's speech at one point during the story, is inspired by 9x08. I was just trying to turn this somewhat debatable episode into something more positive.

The story is all written out, just chapter 2 and 3 still need some tiding up but I shouldn't be too long in posting them. This is unbeta'ed and as such all mistakes are mine and mine alone (although I tried my best to catch them all).

The Bet

"NO way!"

"Mhm. I'm telling ya."

"What? All of them?"

"Affirmative. Come on Ash, just look at them. For one, look at the clothes they're wearing. When was the last time you saw a whole group of people in turtle necks, in September!? And then the way they hold themselves. Basically screams 'never been tapped'."

"Oh, and I bet, you would just love to 'tap' some of that."

Dean nodded enthusiastically. What was there not to like? Teaching a blushing virgin a few tricks of the trade? He could think of a worse way to spend his Saturday evening. But before he could answer his friend, they were rudely interrupted by their boss, old slave driver that he was.

"Hey! I'm not paying you asshats to just stand and have a nice natter. Get your pretty asses back to work. Table 4 is still waiting to have their order taken." Crowley's annoying voice and even more annoyingly British accent cutting their rather entertaining conversation short.

"Got it." Dean said, smirking. "Watch me," he winked at Ash before sauntering towards table 4, which seated the rather illustrate party that had been the focus of their exchange. Six girls and four guys, in age ranging from early twenties to early thirties, Dean would guess. And all of them 'screamed' never been kissed at him. Oh, he would be having some fun tonight.

He plastered on his brightest smile, focusing in on the red head that had grabbed his attention the minute she had walked in.

"Good evening. My name is Dean and I will be your waiter for tonight." He passed around the menus and threw in a wink for good measure and bingo, the red head, while managing to hold his gaze, was definitely blushing. Dean would bet she was a feisty little thing.

"Would you like to order any drinks while you decide on your food?"

There was a short conversation between the people at the table and then it was decided that they would order a couple of bottles of sparkling water between them and three were even daring enough to order a coke. 'Raunchy' Dean had to bite his tongue to not let that slip out loud. But honestly, water? On a Saturday night? Seemed like these guys needed more than just one stick removed.

"Coming right up." He grinned and walked back to the bar.

"Definitely virgins. The lot of them. Unless it's an AA meeting. Water, they ordered water!" Dean said like it personally offended him.

Ash just laughed. Obviously his bar tending skills would not be needed for table 4 tonight.

"Still, the fiery red. I caught her eye."

"You're so full of yourself." Ash teased while pulling out the glasses and four bottles of water.

"Erm…" Someone cleared their throat behind them and Dean spun around being met with the bluest set of eyes he had ever seen.

"Can I help you?"

"Ah, yes actually." Blue eyes said quietly as though he didn't want to be overheard.

"See, it is my friend's birthday tonight, we are sitting over there." The man pointed to the table Dean had just taken the order. How had he not noticed him and those eyes? Ah yes, red head.

"Your girlfriend?" Dean asked curiously.

"No, we're …part of the same group."

"And what group would that be?" Dean leaned in a bit, flirty grin on his face, seeing his chance for some information.

He could see the man tense and pull himself up, like he was preparing himself.

"The St. Mary's Church Pre-Marriage and Chastity Group", he said sternly, like he was already waiting for the ridicule.

"Ah, ok. Dunno how you guys do it, but 's cool." Dean smiled briefly turning and giving Ash a raised eyebrow before turning back and smiling at them man, who seemed surprised by Dean's fairly relaxed reaction (not having seen the 'I told you so' smirk).

"So anyway, I was … I brought a cake and was wondering whether it would be possible for it to be brought out at the end of the meal?" Blue eyes continued.

"For you… anything!" Dean teased, lips curling into an easy smile. Ash kicked him in the shin. Bastard.

The man averted his gaze for a brief second, almost like he had to gather himself, before looking back at Dean, but not saying anything.

"The cake," Dean said, a teasing lilt to his voice.

"What?"

"You gonna have to give me the cake so I can bring it out later."

"Oh yes. Of course. Here." Blue eyes briefly looked over his shoulder to see if he was being watched before turning back to Dean and handing him over a small plastic bag he had been clutching to his chest.

"Candles are inside and…"

"Relax. This is not the first time I'm doing this." Dean winked, hoping his innuendo would not go unnoticed.

"Erm… Of course. At the end of the meal. Thank you." And Dean could bet the guy sounded flustered. He rested against the bar as he watched the man head back to the table, admiring his very nice rear.

"Ok, first I was totally right!" Dean beamed cockily. "And second, forget red head. I'm gonna get into that." Dean whispered leaning close to Ash. "I like them coy even more than I like 'em feisty".

Ash just shook his head. "Man, slow down, you gonna give me whiplash. That was a quick change of mind."

"You know me. Always been an equal opportunity kinda guy."

Ash rolled his eyes. "Whatever, but, ignoring the fact that the guy is probably as straight as the stick you want to pull out of his ass, what makes you think that he would be just rolling over and spread his legs for you?" Ash now all but whispered, careful not to be overheard.

"Hey! Who says he'd be the one doing the spreading?" Dean made a rude gesture with his legs and how was that even possible.

Ash almost choked on his own saliva. "Dude, TMI! But honestly, if he hasn't done it yet, he clearly is not just going to give it up for any Dick, John or Mary that comes his way, even less for some manslut like you."

"Well, I might just be that awesome. Also, that guy - as gay as they come, repressed virgin or not. I'm telling you!"

"Tell you what. You manage to get into that guy's pants within a week and I give you 100 bucks."

"Why not make it 200."

"God, your ego is so over-inflated, how do you not just spontaneously combust? But- Deal! Easiest 200 bucks I've ever made."

Dean gave his friend a cocky grin as he picked up the tray with the glasses. "Watch and learn, watch and learn my young apprentice," he laughed, swinging his hips as he walked back to table 4.

#

Dean knew he was good. He never had a problem scoring anyone he set his sight on, although admittedly, those people generally didn't have a vow of abstinence hanging over their heads. But that just made the whole situation even more appealing. Dean loved the challenge of getting someone's attention and then systematically taking them apart until they were putty in his hands, and he basically could fuck them right there and then, wherever there and then happened to be.

He went for full on charm offensive. Giving everyone on the table almost equal amounts of attention (after all he needed the tips, his brother's college didn't pay for itself) but letting his eyes and smile rests slightly longer on the dark haired man, whose name still escaped him, 'accidentally' brushing against him as he refilled his glass, or leaning in close as he picked up the empty plates. All these gesture were to be explained away innocently enough should Dean need to but he had the distinct feeling that that would not be the case. As much as the man tried not to show that he was affected whenever Dean was nearby, he had caught him staring once or twice, blue eyes fixed on his form only to be quickly averted when he had been found out.

He just needed to somehow get this guy alone for a minute, or find a way to get his number. And Dean knew this was not one of those situations where asking the guy outright would go down too well. Stealth was what would be needed. It would come to him. It always did.

"Dean."

"Gimme me a sec, Ash." Dean hissed, in the middle of restocking the drinks cabinet.

"Ok. Not that I couldn't do with easy money, but I like a fair fight. Just thought you might want to know that my 200 bucks are about to walk out of the door."

"Shit, what?" Dean's head shot up. "They haven't even paid yet."

"Yes, they have. Crowley took care of it, while you were busy daydreaming."

"Shit, shit, shit," Dean cursed under his breath, leaving the bottles abandoned on the floor, and bolting towards the door, in time to catch up to the object of his desire.

"Hey," he said breathlessly, turning on the smile factor.

"Yes?" the man turned around, looking at Dean perplexed.

"I … erm, I was thinking, would you want to meet up sometime."

"What?"

It took a second for the man to catch up with what Dean was asking.

"I, you know- I'm flattered but I'm not, I don't…" he stuttered, eyes darting between Dean and over at his friends who watched the scene with amusement from where they were waiting on the sidewalk.

"Oh, no, no no no… I mean, I just, I guess you got me curious about, like why would someone choose to, you know… not do it."

At that the man's blue eyes lit up slightly. "Oh, you want to talk about chastity."

"Well, I know it's too late for me but…"

"No, see, it's never too late to recommit yourself but, it's probably not the best place to discuss this here. I can give you my number and we can arrange to meet, if you wanted, I could ask my pastor along."

"I… if it's ok, I would like to talk to just one person first, it's kind of a sensitive topic." Dean smiled shyly. He could go for coy too, no problem.

"Of course, you got a pen?" The man's voice all but softened at his request.

"No, just punch your number in my phone." Dean said taking out his phone and handing it over.

He watched mesmerized and long slim fingers made quick work of the number (and imagined what else those hands would no doubt also be good at doing) before handing the phone back to him. Dean looked at the new contact curiously.

"Castiel. That's an interesting name." The man rolled his eyes. "Sorry, bet you get that a lot."

"You could say that. I'm normally free in the evenings so whenever you feel ready."

"It's my day off tomorrow." Dean burst out.

"Oh, ok, well- give me a call and maybe we can meet up. I have to go now." Castiel said pointing at his waiting group of friends.

"Of course, thanks. Nice meeting you Castiel." Dean smiled and held the door open for the man to walk through. He sauntered back towards the bar, grinning cockily at Ash and holding up his phone.

"And that's … how it is done!"

"Smooth. Got to give you that. Still one week and counting!" Ash laughed before turning back to wiping down the bar.

#

"Nice place you have here." Dean sat in the middle of Castiel's living room, on the couch with Castiel sat opposite him in an armchair. He had texted him in the morning and to his delight the man had agreed to meet him in the afternoon for a chat.

"Thank you."

"Can't be cheap, what you do for a living?"

"I teach, middle school." Castiel replied, locking eyes with Dean before looking a way again.

"Cool. Never thought it would be enough to rent a place like this though."

"I was lucky I guess. Inherited some money which allowed me to buy this place."

Dean nodded in understanding. "Lucky indeed."

There was a small silence, enough time for Dean to turn on the smile factor, fixing Castiel with his gaze and, not so subtly, letting his eyes wander over the man's form. If he had noticed, he wasn't showing it, his own blue eyes staring back into Dean's, making Dean shift in his seat. God, the guy's eyes were something else, and Dean had to get his mind out of the gutter fast before he would embarrass himself, as he imagined staring into those eyes as he slowly fucked into the man.

"So you're a waiter full-time?" Castiel asked, trying to keep the nervous tension out of his voice. The man was unsettling him in a way that was making him feel twitchy, but also had an appeal of 'forbidden fruit' about it.

"No, I'm actually a mechanic. I do waiting on the side, to help put my little brother through college. Bright kid he is, got a scholarship to Stanford believe it or not."

"Wow, so two jobs. That must be- tiresome."

"It has its moments, but sometimes I meet great people, like you." Dean directed a smile at the man opposite him, and was pleased to see him turning away for a second, clearly affected by it.

What followed was a short awkward silence, which Dean used to make himself more comfortable on the couch, slouching back, bringing his arms up behind his head for a long stretch, knowing full well his tight fitting black t-shirt would ride up just enough to expose a tiny slither of skin. It was a proven move and always had the desired effect. Yes, he knew he looked good and he wasn't afraid to use it.

Castiel could feel his face flush. Of course, he put it don to the fact that he didn't really have much experience with introducing people to his 'life style' if that was what you could call it, rather than being affected by the man on his couch. While he understood Dean's desire to not have too many people present when first addressing these issues, he now wished he had someone else here with them. Whether for Dean's or his own benefit he was not too sure about at this stage. He had spoken to his pastor and he had given him some pointers. Make small-talk first, get the person to feel comfortable and relaxed. He hadn't mentioned anything about making Castiel feel relaxed though, and he could feel the tension in his shoulders. No point dragging this out any longer.

"Erm, so, maybe best to jump straight in, what do you want to know?"

Dean had to give it to Castiel, he was definitely holding his own, although he had noticed the way the man's eyes briefly found their way down to his midriff, resting there just for a second or two, before coming back up to focus on his face.

"Ok, so, I guess there is not much point in asking you why you're doing this. I assume it's got to do with your upbringing, your religious beliefs and …"

"Well," Castiel interrupted him. "While you are right that my faith does encourage waiting until marriage until having sexual relations with another person, it is more than that for me. I don't know about you, but to me the idea of finding someone you can share this most intimate act with, the person you want to spend the rest of your life with - to be the first person to touch them in that way and in return for them to be the first person to touch you, is very appealing. It is what I want. Call it romantic or old fashioned or whatever but to me that what makes this whole thing special. Don't you, I mean - I don't know you but I could not image just "doing it" with someone. I need to get to know them, establish a connection. You know."

Dean's sarcastic brain supplied 'how would you know' and he had to work hard not to let it slip. On the flipside, Castiel sounded so convinced and after a moment Dean could do nothing but listen to his voice, captivated by the low rumble. He probably only caught about fifty percent of what the man actually said. Because, God help him, he had a voice to die for, and Dean could listen to it all day. So he was kind of sad when Castiel finished, looking at him, clearly waiting for his input.

"Ah, well, never been one for that kind of personal attachment, I'm more a love them and leave them kinda guy," Dean joked, before remembering why he was here, "but… what you say sounds nice, if it's you know, your thing. But while I kind of get the whole not having sex until marriage thing, you surely must have you know… pleasured yourself in other ways?" There just was no way someone of Castiel's age had not indulged in a little self pleasuring.

"You mean masturbation?" Castiel asked bluntly but not flinching. He had heard those questions before, although they normally didn't come attached to such a nice package, and Castiel gulped, he didn't want to think of Dean as anything other than someone enquiring about abstinence.

"Yeah, I mean that's not like having sex really, is it?"

"I know you're gonna laugh but no, I have never masturbated."

Dean's "whaaaat?!" rang loud and clear around the room. "Dude, how is that even possible, I mean, what are you doing about morning wood for example, and don't tell me you're not getting that, you're a guy for goodness sake." Dean looked like his green eyes were about to pop out of his head.

Castiel let out a nervous laugh. "Well, I am but a man and, of course, on occasion I wake up aroused or, had the odd wet dream. After all I am not foolish enough to guilt myself into thinking I can control my dreams. But anything conscious, like touching myself or seeking pleasure in that way, no."

"So you never, touched yourself down there? Not even a bit? Not even when you lather yourself up in the shower or - just gripped yourself tight when the pressure was really getting too much - I assume you don't watch porn - but there must be things that arouse you- and relishing in that sweet tight pressure and promise or relief as you press into your hand, letting the thumb slide over the head of your cock and feel your whole body shiver at the touch as you gently rock into your closed fist, just feeling the friction, working yourself closer to the edge and -"

"Dean!" Castiel's strained voice effectively cut Dean off. And Dean could be a total bastard and shove his by now straining erection in Castiel's face, giving him something to really get flustered over. But the way the man looked nervously at anything but him, made Dean reconsider; it was not the time yet. The guy would no doubt panic and probably throw him out. Instead he rearranged himself, hiding his hard-on as best as he could.

"Please, could you … stop talking about it?"

"Oh, yeah, sorry, got carried away." Dean smiled impishly. "Just don't get why you can't even do that. I mean, if I, you know, was considering this whole recommitting and abstinence thing, would that involve no jerking off as well? Because I have to outright tell you, I don't know if I could do that." Dean leaned in a bit for dramatic effect, fixing the blue eyed man with his stare.

Castiel felt hot and flushed and not at all sure how to answer that question, and Dean really needed to stop looking at him like that. As far as he was aware all his friends in the group did abide by the no masturbation rule, but then again, what people really got up to within their own four walls he had no idea. And while he had managed to keep himself pure, he would not condemn anyone who had resorted to the occasional 'helping hand' if that kept them from the bigger evil of having random sex with someone.

"I guess that would have to be between you and God, or whatever you believe in, in the end. Maybe, if it would help you feel like you need it in order to hold to your commitment, then- I don't know, maybe it would be permissible!"

There was an awkward silence, which Castiel eventually ended by asking his guest whether he wanted a drink which Dean gladly accepted. Castiel returned after a brief trip to the bathroom, with two glasses of lemonade and placed on in front of Dean on the coffee table, taking a sip of his own.

"So, in all your years, you have never met that someone special yet?" Dean changed the subject subtly. Also, because he kind of wanted to know. Was there never even the real temptation for the man to take things further?

"Well, short answer is no, obviously, otherwise I wouldn't still be part of the 'club'." Castiel smiled, making his eyes crinkle up at the corners, Dean couldn't help but notice.

"So no special lady ever caught your eye? Or maybe - guy?" Dean knew he was pushing it but the way Castiel took in a deep breath; he knew he hit a nerve. Bingo. His gaydar hadn't failed him yet.

"Dean I- I can't …it's not…"

"Don't tell me your one of those homophobic extremists who thinks gays are all sick or something and need therapy." Dean rolled his eyes. Abstinence he could deal with, it was a choice but being gay, or as he was, bi, that was not a fucking choice and he had no time for people who believed otherwise, not saying that this would stop him from still wanting to fuck Cas senseless.

"No, in fact our church is actually fairly open; we have out lgbt members in our church. Still I-, and this is were you will disagree with me, I consider marriage to be valid between a man and a woman, and as I also believe sex belongs in the context of marriage - well you see my predicament. The general idea that as such you either have to stay celibate or find a suitable partner of the opposite sex."

"That's just crap." Dean burst out way too passionate for his own liking. He was here to get a job done not to take a personal interest in Castiel's slightly skewed outlook on life.

Dean saw Castiel flinch at his outburst and he had no idea where that had come from. It was definitely not the way to charm himself into the guy's pants. But the man had just looked so sad for a moment, that Dean couldn't help but care, although he knew caring generally didn't get you anywhere in life.

"Sorry man, Just, you're telling me that it's not ok for you to find someone you might actually love and have a loving committed relationship with just because they're of the same gender, but that it would be totally ok for you to go and marry some poor girl under some pretence, probably making both of you miserable in the process, just so you can uphold some weird outdated interpretation of marriage? I just don't get it, how would that be fair on anyone?"

And oh god, Castiel looked like a kicked puppy just then, and Dean wanted to go over and just give him a big hug, telling him that is was ok, and that was not something Dean Winchester did, ever! Unless it was for his little dork brother. Shocked by his own impulses, he stayed where he was, giving Castiel time to think, and himself time to get back on track.

"No it probably is not fair, but when is life ever fair?" Castiel said after some deliberation. "Still it is what I believe and I am hopeful that one day I will meet someone I can imagine spending the rest of my life with and if not, I just have to find myself a riveting hobby to keep me busy." And he let out a small chuckle that Dean couldn't help but find endearing, no matter how forced it sounded.

"Right, like fishing," he grinned.

"Fishing, yes," Castiel returned the sentiment with a small grin of his own. "But really this is not all about me," he didn't like the focus to be on him. "What made you even consider the idea of abstinence?" This thought had crossed his mind more than once since last night. Dean just didn't seem the type at all, but he knew better than to judge a book by its cover. He firmly believed in second chances, or even third if need be.

"I don't know, man, just you know or – well, you don't know- the sex is all nice and stuff but I never take the time to get to know someone first, and I'm not getting younger." Dean chuckled. "Also, what you said kind of sounded nice, the whole spending time together first. To be perfectly honest, I have no idea what being in love feels like so, when I saw you guys yesterday, it just made me think. Maybe it's time to try a different approach."

"So you wouldn't miss the whole being with someone like that?" Castiel's lips curled into a tiny smirk, and was he actually flirting with Dean or just yanking his chain?

"Hell yes, I would! But maybe there has to be more to sex than 'hello and goodbye' and if not doing it will help me figure it out, then maybe that's a sacrifice worth making." Dean said and hoped he sounded sincere enough. To be honest, just imagining possibly two weeks without doing it, would be a challenge. Well, technically it might be as much as three, he had been to busy these last couple of weeks to take anymore home. He hoped he would crack Cas way before then or his right hand might quite possibly suffer from RSI by the end of this.

"You - well, you surprise me. You are not what my first impression was telling me." Castiel sounded honestly surprised.

"And what was that?" Dean leaned forward a bit, capturing Castiel's gaze with his own. And damn, those eyes again!

"Total flirt, desperate to get someone to bed on a Saturday night, in short, total douche." Castiel stated dryly.

"Well thanks for the 'douche'," Dean sniggered, "and guilty as charged for the flirt but no, I was actually not trying to get anyone into bed, just can I be honest with you?"

"You shared your masturbatory habits with me; I guess nothing you could say now would shock me." Now it was Castiel who was leaning in and Dean knew he had the guy's full attention.

"Ok, well, here's the thing, I-" Dean gave a dramatic pause, gulping. "I, when I approached you yesterday, I initially only really wanted to get your number."

"Oh, but Dean you understand that…" Castiel's face fell.

"No, please let me finish," Dean held up his hand dramatically. "I said I was trying to be honest here- and well, I liked the look of you, and yes, I thought maybe I had a shot. But now, talking to you, it – I think I get it … I never had a relationship and what you say sounds nice. I think I… would like to do that. Do the whole thing you were talking about. I never really take the time to get to know anyone. And no, I'm not trying to come on to you here, so relax," Dean smiled at the slightly constipated expression Castiel pulled.

"I just, can you help me to figure this out? You know – help me along this whole 'wait until I meet the right one' path?" Dean hoped he put the right amount of stammering into request, adding a shy smile for good measure.

"Oh," Castiel was quiet for a long time, worrying his bottom lip between his teeth. Not sure which bit of information his brain should focus on first. So he was very surprised when the first thing that came out of his mouth was "so you're actually gay? I could have sworn you were flirting with Anna last night."

"The red head?" Dean chuckled. "I was." He shrugged his shoulders. "I'm not really limiting myself to one sex. What I mean is, I can find men attractive on occasion, and," Dean looked straight into Castiel's blue eyes. "At the danger of sounding sappy, when I saw your eyes, I wasn't really interested in flirting with anyone else anymore." And god, wasn't that the goddamn sad truth.

Castiel felt like a freight train had just hit him full on. His heart was hammering in his chest, he could feel his pulse speed up and his hands go clammy. He couldn't get himself to look away from the man opposite him. All the while his head was screaming 'danger, abort'. There was a reason he tried to stay clear getting too close to members of his own sex, it was all a simple exercise in limiting temptation, because a relationship with a guy could never lead anywhere.

Not being able or willing to focus and process the implication that this man, Dean, apparently found him appealing, he focused instead on the idea of helping a 'lost soul' on its way. He had never really been one for making friends but maybe he and Dean could become that. 'Partners in crime' so to speak. He seemed sincere enough, staring at him with his big green eyes. After all everyone deserved a second chance and who was he to judge Dean's past behavior if he wanted to change.

"I guess, I can try to do that. Hold on." Castiel said and jumped off his chair and left the room, coming back a few minutes later with a couple of books and pamphlets.

"Here, maybe try and read these. They have been very helpful to me over the years and might help you focus on what you want out of this and why it's worth doing."

"Ah, thanks man. That's… thanks. I'm not normally a big reader but I will give these a go" Dean said taking the books out of Castiel's hand and looking at them.

A tense silence set in the room as Dean studied the books and Castiel tried not to study Dean, with mixed results if he was being totally honest.

After leafing through the books for a few minutes, Dean smiled at Castiel and stood up. He didn't want to overstay his welcome, he done what he had come to do today. Best to leave while he was ahead.

"So," he cleared his throat. "When- I mean, can we meet again and talk some more about this?"

Castiel considered this for a moment, seeing Dean again was temping, then again seeing Dean again was tempting. He felt like he was being torn in half, and like he might regret whatever he decided to do.

"Erm- honestly, I don't know how much more help I can be right now, but of course, if you need someone to talk I will be here. Just, maybe you want to come along to our meeting tomorrow evening?" That should be safe enough, seeing Dean again in a controlled environment so to speak. He noticed Dean's apprehension and nodded encouragingly at the man. "And before you say no, you wouldn't have to say anything, just sit in the back if you want. I promise we don't bite."

Castiel smiled, and god, with a smile like that he could probably sell ice to the Eskimos, Dean thought, letting himself indulge the view just for a moment. Seeing him again tomorrow was kind of vital, he was on a tight schedule after all, and he was sure he could endure the 'group' for one evening.

"Ok, I mean yes, I come, as long as no one is trying to convert me to anything." Dean smirked at the blue eyed man.

Castiel laughed at that. "Can't make promises, but if anyone tries, I'm sure you're old enough to stand up for yourself."

"Well, then it's a date." Dean added a little wink to his tease, just enough to make Castiel notice and blush (and wasn't that adorable) but not scare him off.

#

"I'm so in there, Ash, easiest 200 buck ever." Dean could hardly wait to call his friend and give him an update on how his meeting went.

"I believe it when I see it," Ash laughed at the other end.

"Seriously, you should have seen him when I shared some of my jerking off habits with him. I am positive he was sprouting a boner. Well, at any rate; he had to excuse himself to calm down. I for one know that my hand will definitely get a good workout tonight, the guy's just that hot."

"Again with the oversharing Dean!" Ash tried sounding affronted but Dean knew him better than that.

"So, what's the plan for loverboy then?" he enquired further.

"Well, I'm going to his group with him tomorrow – shut up Az – of course I can keep it in my pants for one night! Yes - I know it's a room full of virgins, I have willpower you know." Dean had to actually hold the phone away from his ear as Ash's ear-splitting laugh was in danger of bursting his ear drum. "I plan on a lot of hidden flirting and accidental touching, naturally all done with stealth as we will be watched, and of course some alone time after, maybe a kiss goodnight."

"Wow, at that rate you will bed him in like - a year." Ash hollered.

"Shut up, good things can't be rushed, and he is not easy, the man got class. He will feel to need respected first." Dean rolled his eyes at that, respect his ass.

"And you are the one to give him that 'respect'. Dean, you don't even respect yourself."

"Ouch, that hurts Ash." Dean sounded mock offended but couldn't hide the laugh. "Respect is overrated, especially when you could be having a good time instead. Well, anyway, I'm at my car, see you tomorrow."

"Laters." Ash hung up the phone still laughing.

#

All evening Castiel had had a feeling that he was royally screwed.

Well, that had only been a rather abstract concept, up until the moment in the middle of the night when he woke up sweating and panting, humping his mattress, moaning at the friction and images of bright green eyes and broad shoulders vivid in his mind. He knew from the occasional wet dream, when he had woken up literally as he was about to climax, that he was almost too far gone to stop the impending release. Although he probably could make it to the bathroom and a cold shower just in time to stop this if he really wanted to. The only thing was that he didn't really want to stop.

Unlike previous times, when it had just been a physical reaction to a natural bodily need, Dean had provided his mind with plenty of fodder to put a whole new level to his arousal. Every brush of his erection against the mattress sent a spike of electricity through him. And the idea of imitating intercourse by thrusting into his own hand was definitely due to the man's vivid description of his masturbatory habits.

Castiel, sweaty and panting, fought for only about a minute with himself before lifting his hips up and push his pyjama bottoms and boxers down enough to give him access to his straining cock. He pushed his right hand between his body and the mattress, gripping his erection and gyrating his hips, humping into his fist. The friction felt heavenly and the way his synapses were firing, his muscles tensing in anticipation of release was so much more intense than he had ever experienced before. His hips thrust faster and faster as he buried his head in the pillow. In no time he could feel his body go rigid before the orgasm ripped through him. It was so strong that he couldn't stop himself from moaning as he shuddered and felt a wetness coating his fingers.

Castiel collapsed in on himself, for a moment too dazed to worry, but soon enough the gravity of what had just happened hit him full on, effectively pulling him back to reality. He really had no idea whether he wanted to laugh hysterically or cry at the loss of his innocence. Also, now he had to change the soiled sheets and clean himself up. On top of that how could he be expected to meet with Dean tomorrow and look into his eyes, knowing that the man and his stupid, perfect face had been on the forefront of his mind while pleasuring himself. He was supposed to help Dean along this path, not take advantage of him.

He could of course cancel on the man, although it felt wrong to lay the blame at Dean's feet. It was solely his lack of restraint that was to blame and Dean shouldn't be the one punished for it. The group would be good for Dean, and also Castiel had a distinct feeling he needed a boost in his convictions. He had managed twenty-eight years without getting himself off like that, what the hell had gotten into him? Not knowing what to do, he groaned into his pillow in despair.

Yes, he was screwed for real.

#

Dean had to admit he might have to readjust his world view ever so slightly. These people weren't quite as stuck up and prudish as he had always imagined. He was sat in the back, watching the 'proceedings', not sure what to expect. There had been a fair amount of laughing going on, as people generally caught up with each other's lives before the meeting was officially opened. People were curious as to who he was, some having recognized him from that night at the restaurant. Thankfully Castiel had intervened and they had pretty much left him alone after. Speaking of the blue eyed man, he had been rather funny and tense when he arrived, not really meeting his eyes, but over the last hour or so, he had loosened up, and glanced over at Dean ever so often, giving the odd encouraging nod. Although as far as Dean was concerned he was definitely sitting too far away from him. He would just have his eyes do the flirting for now.

People were surprisingly vocal about something they were apparently trying so hard to avoid, namely S.E.X. There was Steve, who had been dealing with his attraction to a co-worker who was making it very clear she wanted more than just friendship. He was encouraged to ask her out on a date. (So these guys were allowed to date, Dean's ears had pricked up at that. He naively had always assumed these kind of people just somehow magically ended up together or get married off). Steve was given tips on how to avoid the inevitable temptation of going too far, while seeing if this girl could be someone he might want to marry one day. Then there were Susan and John who had announced their engagement to the cheers and hollers of the group and Dean couldn't help but be swept up by all the commotion and feel happy for them too.

The rest of the evening was just a general sharing about struggles, followed by a string of tips and affirmations why it all would be worth it in the end. Dean at that point tuned out, resting his gaze on Cas instead, realizing he rather liked the pet name he just came up with for the man, and imagining things, all kind of good and naughty things. His mind slowly drifted to places that he should not be thinking about in a crowded room, especially a room full of virgins.

Cas' voice was soft and soothing and, god, oh so low and gravelly, Dean felt like he was being lulled into some kind of hypnosis by it and – WAIT! What? Cas was speaking, hushed and labored and – OH…oh! Did he really just say the word 'masturbation'? His face looked very flushed and he wouldn't meet Dean's eyes, instead focusing on the group leader, who smiled reassuringly at him, the rest of the group looking all solemn and supportive, nodding their heads ever so often.

Oh, this was gold! Cas had gotten down and dirty, after one, just one pep talk from him.

Dean: 1, Cas: 0. Or well, maybe Cas: 1 too, being as he seemed to have taken the first step on his sexual awakening. Suddenly feeling very much more relaxed, Dean slouched back in his seat, stretching his legs out before him, letting the rest of the meeting wash over him.

#

"And, what did you think?" Cas said, pulling Dean aside after the meeting before the two or three people, he could already see edging towards him, could pounce.

"Honestly, better than I expected, you guys are kind of normal." Dean chuckled.

"Well, I wouldn't call us normal, but, thanks I guess," Cas huffed but his voice had a kind of fondness to it, that made Dean smile. Cas on his part had decided to try to not act weird around Dean, after all the man didn't know who the object of his fantasies was last night. Despite having felt the need to share and get encouragement from the group, there were certain things that didn't need disclosing.

"So, think you might want to come again?"

"You know, I think I might." Dean felt his chest tighten at the genuine smile Cas was sprouting. He shuffled his feet for a bit as they both tried not to stare at each other (too much) "So- the night is still young, fancy grabbing a beer- or coke or something."

"Dean! I do enjoy the odd alcoholic beverage," Cas rolled his eyes. "But I still have classes to prepare and-"

"Ok," Dean let his disappointment be apparent on his face, "I understand, just maybe another time to filter through all the info I got tonight." Dean waved goodbye and turned to leave.

And Castiel knew he would regret this, knew he should absolutely not even think about spending another second with Dean. He was a mess after just spending one afternoon with the man. But seeing him walk away suddenly seemed like an unacceptable option. "Wait," Cas called after him, grabbing his jacket and bag. "Maybe just one quick drink."

Dean smirked before turning around, face changing to a small timid smile.

Dean insisted on buying Cas a beer as a thank you for putting up with him, and after only a bit of protest the man accepted, making it quite clear that the next one would be on him. Dean smiled; he could definitely work with that.

They found an empty table at the back and sat down, both nursing their beer, taking the odd sip and looking at each other intermittently. Dean edging closer to the object of his affection inch by inch until their legs brushed and he felt Cas jump before he relaxed back against it with his own leg, trying his best to act like nothing was wrong.

It was Dean who broke the silent first. "Dude, that was – really brave back in there."

Cas looked at him confused before realization dawned and he looked away blushing, taking another gulp of his beer.

"Hey," Dean said, nudging his knee against Cas. "Nothing wrong with what you did, at least from where I'm standing, as you well know." He nudged Cas again and the man looked up, blue eyes meeting green and Dean felt his stomach give an excited flip.

"Just- I think it was brave sharing it with the group like that, and they all seemed -supportive."

Cas swallowed hard but nodded. "Yeah, guess I had a good run lasting this long," he huffed, sounding slightly bitter. He rather not talk about this with Dean.

"You're being too hard on yourself, you are only human after all." Dean smiled encouragingly, bumping Cas' shoulder gently with his own. Cas gave him a tired smile in return.

They fell into a tense silence for a few minutes, before Dean leaned in, whispering into Cas' ear, which had Cas' skin prickle when he felt Dean's breath ghosting against his skin. "You wanna know a secret?"

Cas looked at him, a nervous mix of curiosity and apprehension, but nodded after considering the question for a moment.

"I kinda did the same thing last night." Dean volunteered with a glimmer in his eyes, and Cas honest to god chocked on the sip of beer he just took, coughing and spluttering. Dean had to resort to patting him on his back as he tried to catch his breath.

"I did not need to know that." Cas rasped, trying to catch his breath, but he smiled at Dean.

Dean laughed in return, wiggling his eyebrows at Cas. "Well, shared misery and all that- guess I'm not doing so well on the abstinence front."

"Dean, it's- don't beat yourself up, it's like changing a habit, it will take time. At least ‑" Cas fixed him with his blue eyes, shining with the tears from his coughing fit. "You didn't end up taking someone home, so that's a start, right?" Cas said with a straight face, although Dean could see the twinkle in the man's eyes.

"You know me too well already," Dean smirked, relaxing back into his seat and slinging his arm around the back of Cas' chair, and when the man didn't protest, left it there, resting it loosely against his upper back, feeling the heat of Cas' body slowly seeping into his arm. He hated to admit this, but he actually enjoyed the man's company. He had a feeling there was a witty, dry humored, snarky SOB hiding in there somewhere, and Dean really wanted him to come out and play.

They finished their beers and decided to call it a night. Dean insisted on walking Cas back to his car.

"So, thanks for a 'memorable' night." He said, shuffling his feet, not wanting to go quite yet.

"Likewise," Castiel smiled and before he could process, he was pulled into a hug by Dean. He normally wasn't very big on the hugging front, so it took him a moment to move his arms, which were loosely hanging by his sides, and placing them around Dean's waist and back, giving him a few 'manly' pats on the back before detaching himself.

"So- we should do this again."

"The hug?"

Dean laughed. He was really starting to like Cas. "Well, we could do that too. But I meant, hang out."

"Yeah, we should." Castiel didn't actually want to say that, but his mouth suddenly had a mind of its own as he smiled back at Dean.

"Night, Cas" Dean waved as he turned around to walk to his own car.

"Night, Dean," Castiel couldn't hide the grin on his face at the pet name, and for the umpteenth time in two days had a distinct feeling of being absolutely and utterly screwed and not really being able to care about it. He might have to re-evaluate his outlook on life. He had a distinct feeling he would be doing some googling tonight.

#

Tuesday was a bit of a washout as far as getting to the next stage of 'plan Cas' was concerned. Dean had texted him during the day, to ask if Cas wanted a repeat performance of last night (hug optional) but he had to decline, as he had a students-teachers evening to attend, something which apparently he was only allowed to miss in case of his impeding death.

Dean initially had not been to please as this blew a big hole in his tight schedule, as tomorrow evening he had to work. Maybe he was pushing his luck a bit only having given himself seven days to seduce Cas. But no, he didn't want to entertain those thoughts, he would just have to try harder tomorrow.

But as it happened, he needn't have worried too much. They ended up texting each other throughout most of the evening, probably talked more than they would have if they had met up, and Dean was starting to see a whole new side of Cas. To his own dismay, he had to admit he actually thoroughly enjoyed their texting ping-pong. Cas' texts were getting increasingly frantic and questioning his sanity ever having chosen this profession and Dean being his shoulder to cry on so to speak. Maybe this getting to know someone before you have sex wasn't such a bad concept after all. If anything, Cas became more appealing to him by the minute. That thought unsettled Dean deeply so he shoved it to the back of his mind, instead taking good care of himself in the shower that night, letting his mind go freely to the things he would want to do to Cas when they finally got there.

Cas for the first time since he could remember having to attend parent's consultations went to bed giddy and not the zombie he normally turned into. Dean had taken his mind sufficiently off bratty kids and demanding parents, all thinking their little precious is the next Einstein. Really having someone to share things with made life that little bit easier, and more enjoyable.

For a short moment he had even considered calling Dean to ask if he still wanted to meet up, but then he remembered the lesson plan he still needed to draw up and he couldn't let his professionalism slip just because he might or might not start to get attached to the man. It scared him how in the short span of a few days Dean had wormed his way into his life and Castiel needed a day or two to analyze where that might possibly leave him.

#

Cas was startled by his phone going off, being absorbed in grading some school papers, something which had managed to occupy his thoughts and stop him from thinking about Dean and how he already missed the man after not having seen him for one day.

- HELP -

He looked at the text message in confusion, it was Dean. Speak of the devil! He was not sure how to answer that, when his phone pinged again.

- CAS HELP ME -

- What with? –

- MY VIRTUE -

- ? Care to elaborate –

Castiel stared at his phone for a few long minutes, finger hovering over the call button. What a weird cryptic message to leave him and then not follow up with an explanation. Dean was definitely one of a kind. When the phone finally rang, Castiel was so taken by surprise that he almost dropped it.

"Dean, what is going on?"

"Sorry, had to find a quiet corner to hide in before I could call you. Cas, seriously, I need your help man."

"Of course, Dean. Just it would really help if you told me what with."

"I- I really want to do this abstinence thing but- there is this guy, god, he's been chatting me up all night, and I can't just walk away because I'm working, and damn it Cas! I'm about to give in. I'm only human after all and it's been like two weeks and he is basically offering himself up to me and-"

"Dean, take a deep breath."

Cas listened to Dean's breathing for a moment.

"Ok, calm now."

"Now, you calling me is a good sign. You obviously really want to give this a go. Remember you don't have to be a slave to your impulses. If you don't want to do this, you should just go and tell that man to leave."

"Cas, I tried ok, but the guy just won't take no for an answer. Now he moved to the bar and he is basically eye fucking me, and worst of all, he would be totally my type. I'm so close to caving - Cas help me. I'm about to close up here and if he waits around for me after, I'm done for."

Cas groaned, he could feel the man's desperation in his voice, but what was he supposed to do from all the way over here.

"Dean, just- I don't know what to tell you, stay strong?!" Oh god that sounded like such a platitude even to Castiel's own ears. "I've never been in a situation like that."

"Come down here, Cas"

"… What?"

"I know it sounds crazy, but maybe if he sees me being picked up by someone he will just let it go and, Cas you're my last hope." Dean pleaded, while leisurely leaning against the wall.

Cas had no idea what made him agree. He must be possessed or something. He barely even really knew the guy and already he was going out of his way helping him.

"Ok, I'll try and get there as fast as I can."

"Thanks, Cas, you're a real friend." Dean hung up and strolled back into the restaurant, giving the guy at the bar a wink, which he returned with a nod.

Cas must have broken a speed limit or two, as barely fifteen minutes later he walked through the door, scanning the room for Dean. He wasn't hard to spot as the only people left were a few members of staff and a big, burly guy sitting at the bar, being all up and close in Dean's personal space. And Cas had no idea why, but his stomach was coiling at the way the guy eyed Dean like he was a pound of meat.

"Dean," he called out as he walked up to them. Dean detached his gaze from the man in front of him and beamed at Cas with those hypotonic green eyes which made Castiel go weak in the knees.

"Hey, baby," Dean exclaimed, coming out from behind the bar, strutting up determinedly towards Cas.

Castiel's eyebrows went so high, they almost disappeared into his hairline at the term of endearment, but before he could say anything else, Dean was right in front of him, pulling him into a tight embrace.

"Cas, just go with me," he whispered into his ear before facing him, fixing him with his gaze but a second before leaning in and brushing his lips against Cas'.

Cas' brain went offline at the sensation of Dean's lips against his own. He couldn't even move to push the man away, couldn't move at all. Only when he felt Dean's tongue licking against the seam of his lip, did he spring back to life, a low moan escaping him as he tried to do the right thing but instead found himself opening his mouth to grant Dean entry.

Now it was Dean who was moaning deep in his throat as his tongue met Cas', sliding hard against it. He brought one hand up to the back of Cas' head, pulling the man in even more, deepening the kiss until they were both breathless and he had to pull away.

"I won't be a minute, hon," he smirked cockily at a shell-shocked Cas, who could be dead for all he knew, the way he was standing stock still. Dean waltzed back to the bar, giving the man at the bar a wink.

"Guess that's my queue to leave," he said as he pulled out some money from his wallet and placing in on the bar, giving Dean an accompanying wink.

"No bad feelings," Dean said as he took the money. He owed Benny, BIG, for this favor, but a distinct lack of suitable guys to flirt with during tonight's service had left him with little choice but to improvise. He gave his friend one last nod before excusing himself to get changed out of his work clothes.

He had a hard time to hide how giddy he actually felt. Kissing Cas had been, well, amazing. He had thought about what it would feel like for days, and he knew it was a bit of a dirty trick but he had never said he would be playing fair. And there was no way Cas had not enjoyed the 'Dean Winchester' experience judging by that whimper that had escaped him.

"You're one lucky bastard," Benny hissed at Cas as he walked past, keeping up his appearance as scorned one night stand for a bit longer. Dean must really like this guy to go through all this length to get his attention. And who was he to refuse to play a little cupid along the way.

Cas still stood in the same spot when Dean returned, but as soon as he noticed him approach his face went from shocked to thunderous. Dean put up his hands in surrender.

"Cas, I'm sorry, ok," he worried his bottom lip. "Just, I know those kind of guys. He would have seen right through it if we would have kept this strictly platonic."

Cas' blue eyes were boring into him, and Dean felt himself equally scolded and aroused by the display. He bet Cas would be awesome at angry sex, all rough and commanding and, shit, now was not the time to think about this.

Cas still had trouble forming thoughts, let alone words. He wanted to feel angry, violated at having been used in this way, but his lips were still tingling from when Dean had kissed him. To be honest, he had no idea who he was madder at, Dean for not asking for his permission beforehand or at himself because while he should have hated it, he had very much enjoyed their lip lock.

"Cas," Dean tried again when the man remained silent.

"Don't Dean." Cas cut him off. "Let's just leave it at 'I'm glad I could help'." Although his face portrayed a whole array of different emotions, none of them could have been described as 'glad'.

"Yeah, thanks," Dean said, still staring at Cas, assessing the situation meticulously. He kind of felt like an ass all of a sudden. Maybe he should have given Cas some warning. God, he didn't even know whether Cas had actually ever kissed someone, but if he had, Dean would bet his life that definitely had not been another guy. That thought made him feel even shittier. But in good old fashioned Dean Winchester fashion he laughed it off.

"I guess that leaves my new found virtue intact for another day." He smirked.

"I'm sure you can take it from here." Cas simply said, still too bewildered by this all to even meet Dean's eyes.

"Cas, please." Dean pleaded, what for he didn't quite know. He just wanted for the man to look at him.

"I need to go home. I still have to finish grading my papers." Cas stated somewhat detached, meeting Dean's eyes briefly before turning around and walking out of the restaurant.

"Cas, I'm sorry," Dean yelled after him, not sure he actually heard him. And god help him, he even meant it. He hadn't seen the other man upset before and he definitely didn't like it. Well, he had no idea how he had expected this night to go, but he had envisaged something more along the lines of having Cas pushed up against a wall, devouring his every part slowly and thoroughly. Clearly, he had overestimated his pulling power, or underestimated Castiel's determination on the matter. Then, there was the very real possibility that he just didn't do it for the man, and oh god, was Dean having an existential crisis? He simply was not used to being turned down and couldn't help the brief moment of panic. It was almost enough to have him head to the nearest bar and take home the first person that caught his eye, but only almost. Thing was he didn't really want to sleep with anyone else but Cas. So, this proved a bit more difficult than his average hook-up, it would just add to the fun when he finally got there. Cas would be worth it.

With that thought, he locked up, quickly headed to his baby and drove home, not before he shot of a quick text to Cas, apologizing again.