Dean woke up at what felt like the crack of dawn, blinking his eyes blearily at the sun that streamed through the windows. He felt as if someone was pounding a hammer against his head. The room he saw through his blurry eyes wasn't the one he and Sam had taken. He frowned at that. Then he saw the feminine arm draped over his chest. Oh. Right. He had been at the bar last night. The memories were vague but he had gone home with someone. Carefully so as not to wake the other sleeper, he turned over. A redhead. Like Anna. Only Anna was dead now. His eyesight adjusted as he woke and he frowned as things came into focus and he registered the face of his bed partner.

"…CHARLIE?!"

~LAST NIGHT~

"Are you SURE we can't convince you to come?" Charlie wheedled. The redhead had been in a neighboring town for a convention and had called the boys up. She had just spent the last hour trying to convince Sam to join her and Dean for drinks, to no avail.

"Seriously, Charlie, I just want to finish this up and make an early night of it."

Charlie gave Dean an imploring look as though begging him to intervene, but he just rolled his eyes. "Don't look at me." He heaved an exaggerated sigh, shaking his head. "Sometimes I don't even know how he's my brother." In response, Sam threw an empty beer can at him. "Hey! Bitch."

"Jerk." Sam had been holding his place in his book with one finger; now he opened it again, smiling at the two of them. "Go on. Have fun."

Dean shook his head again. "Your loss, Sammy." He grabbed Charlie's elbow, tugging. "C'mon. There's a good bar down the road."

Dean didn't come to the bar often. When he and Sam were at the Batcave, as he liked to call it, he mainly drank the beer and whiskey they kept there. But now and then, it was nice to get out to a real joint. He realized just then how infrequently he HAD been hitting the bars, which in turn meant how few women he'd been hooking up with. Weirder than that was the fact that he hadn't even noticed, and in turn that he didn't even really care. When had he stopped trying to pick up women every night?

He shook his head, telling himself they'd had far too much to worry about for him to even THINK about hook-ups. Important things. That's all. He'd find someone soon. Someone with soft brown hair and a pair of pretty blue eyes….

For some reason an image of those eyes came so vividly to mind that Dean was struck almost breathless with it. "Fuck." He knew those eyes. Why did he know those eyes?

"Dean?"

Startled, Dean turned to Charlie. "Oh, hey. Sorry. Just thinking." He looked to the bar where Charlie had gotten shots lined up for them. Six each. He raised a brow. "You think you can handle that?"

"Do you?" There was a challenge in her voice, and he laughed.

"Sounds like you wanna make this a contest."

She smiled, sharp and wicked. "I'm down if you are."

Dean reached out, picking up his first shot and raising it. "A contest, then. First one to pass out has to pay the tab."

"But how will they pay if they're passed out?" Charlie quipped, and from the tone in her voice it was clear that she knew she was being a smartass. Dean gave her a Look.

"I will reach into your pocket, take out your wallet, and get the cash."

She arched a brow at him. "So sure you're going to win, Winchester?"

He shrugged a confident shoulder. "Pretty sure, yeah."

Charlie raised a shotglass. "Well then, put your money where your mouth is." Smiling, Dean clinked his glass against hers, and they both threw back the liquor like it was nothing stronger than water.

Many rounds later, both were still going strong. So far they were matching each other beer for beer and shot for shot. Now Dean could hold his liquor damn well, but after a couple hours of this, even he was beginning to get tipsy. This is when things began to interesting.

Men were starting to hit on Charlie. She was one of few women in the bar and she WAS hot. Even Dean had to admit it, and he had never had anything other than friendly feelings for her, unusual for someone with a libido like his. It seemed like men thought that, now that she was drunk, she was more likely to be receptive to their advances. They were wrong.

After Charlie had turned away three men, she seemed to decide it was Dean's turn to handle the problem. Another man came up to her and she immediately draped herself over Dean, arms around his neck, body plastered against his.

"I don't think my boyfriend much appreciates you flirting with me."

Dean looked at, face silently inquiring 'boyfriend?' She just smiled adoringly back at him, batting her eyelashes. He didn't know if he wanted to laugh or kill her. Damn, she smelled nice, though.

The man didn't look at all impressed. "Oh?"

"Yeah. Leave me alone or he'll kick your ass."

…yeah. Kill her was definitely it.

The man snorted. "This puny guy?"

Now, that was it. "Yeah," Dean answered. "This puny guy." He shrugged Charlie's arms off of him. "Care to have a go?"

The man looked amused. Dean could work with that. As annoying as it could be to have someone underestimate you, it could work to your advantage, too. As the man swung at him, Dean ducked, the punch going over his head. He sidestepped it and hit the guy in the ribs. The man spun to face him and Dean gave him a right-hook to the jaw. He stumbled back into the bar, sliding to the floor; an effort was made to stand but his feet slipped out from under him and he sunk back to the floor, back against the bar. Clearly he wouldn't be giving them any further trouble tonight, and by the look of it, no one else would be, either.

Charlie wrapped her arms around Dean's neck again, cooing "my big strong man."

Dean gave her a Look. "I hate you."

"Oh, you do not. Defending my honor."

Dean felt Charlie's warm, soft body pressed against him and wondered something. "Charlie, have you ever been with a man?"

"Been with?" Charlie cocked her head. "What do you mean? Like…..BEEN with been with?"

"I don't know. Whatever you want it to mean," Dean answered.

Charlie leaned back, elbows resting against the bar. "Dated a couple before I decided it wasn't for me."

Dean nodded. "Figured."

"Why're you asking?" There was that curious head-tilt again. For a moment it reminded Dean of Cas, and he smiled.

"Don't know. Just asking."

Charlie grinned. "Don't lie. You've got the hots for me, don't you, Winchester."

Dean's reaction was immediate, making a face. "UGH, no. That's just weird. Ew. No."

Charlie laughed. "Oh, gee, thanks."

"Oh come on. Like you think of me as anything more than a friend."

Charlie considered it. "True." She gave him a once-over. "Still, wouldn't mind tapping that, if I were straight."

Dean shrugged. "Duh. I'm gorgeous." He grinned as Charlie laughed. "And likewise."

She arched a brow at him. "You'd screw me if you were straight?"

He realized what he had said and flushed crimson. "NO! I'm straight! I mean….if YOU were straight! I just…fuck." She was laughing. He glowered. "Shut the hell up."

"No." Charlie took a long sip of beer. Dean watched her, thinking.

"So…." He wasn't sure that this was an okay question to ask, but it was Charlie, and Charlie was usually okay answering anything. Besides, by this point he was drunk enough that it seemed okay to say or do just about anything. "Lesbian sex."

Charlie arched a brow again. "I'm familiar."

"Like…how similar is the real thing to what they show in porn?"

Charlie looked both intrigued and amused by the question. "Huh. Good question." She considered it for a moment. "Well obviously the porn is really overacted."

"Obviously."

"Lot of really fake moans. And the positioning is really overdone."

"Really?" Dean was disappointed.

"Yeah." Charlie looked at the crestfallen look on Dean's face and couldn't help a little laugh, shaking her head. "Dean, when it comes down to it, there aren't as many differences between gay sex and straight sex."

"…seriously?"

"Lesbians use their hands and mouths on each other the same way a man would use his hands and mouth on a woman." She paused. "…though probably with more skill, since they themselves are women and therefor know what women like. Obviously not in all cases."

"Like me," Dean said. "Cuz I'm awesome."

She laughed. "Well obviously the great Dean Winchester is the exception."

"Obviously." He took a moment to mull it over. "So…..it's mainly the whole…dick….thing?"

"That's the main difference, yes."

"Huh." He considered it. "And you use a strap-on." This wasn't so much a question as a statement. He may be curious but he still had a pretty good idea how everything worked.

"Yup. Strap-on, dildo, vibrator…..I've actually got a strap-on in my bag back at the hotel."

"Really?" Dean was intrigued.

"Yeah. You wanna see it later?"

"HELL yeah!" Yeah, he'd probably had too much alcohol tonight. Though if the flush in Charlie's cheeks was anything to go by, so had she. Still, he wasn't so drunk as to get through the next question without embarrassment.

"Have you ever…." Dean actually found himself blushing, which was strange in and of itself. Dean Winchester didn't DO blushing. He gestured in a way that he knew completely failed to indicate his meaning. "…..ever tried it in the back door?"

Charlie seemed to grasp his meaning, thank God. He didn't know that he could handle stating it outright. "Well…..yeah. I mean, it's not like I NEED to…..no pleasure source there for girls like there is for you guys…" And Dean found his cheeks burning up as he blushed yet again. "But you know….nothing like experimenting."

Now THAT was something he could get behind, grinning. "Amen to that, sister." He raised his glass and, with a matching grin, Charlie clinked her own mug against his.

"Why is that, Dean….." and there was a look to Charlie's eyes as if she knew there were more to Dean's inquiries. "…..thinking about doing a little….experimenting…..of your own?"

Dean scratched at the bar top with his fingernail, glancing up at Charlie. "….maybe." His tone was defensive, as if daring Charlie to say something about it. But she didn't. At least not in the way he was afraid of.

"Got anyone in mind?" she asked. Dean looked at her, confused. "To experiment with."

"Ah…..no."

There was a moment of quiet; one could almost feel the hesitation in the air. "…well…." Charlie sounded unsure, as though she didn't know how Dean would react to what she had to say. "….I DO have that strap-on back at the hotel."

Dean's head shot up; he stared at her. There was a long silence as the two simply looked at each other. Finally, Dean spoke up, a small smile curving across his lips. "I think I'd have to be a lot drunker to agree to that."

"Well, then." Charlie gestured for the bartender. He came over and, with a word, lined up more shots for them. "How bout we continue with this drinking contest and see where things take us?"

Dean smiled. "I can definitely get behind that."

Several hours later they stumbled into their room, the door slamming shut behind them. Dean didn't know the last time he had been so completely drunk, and he wouldn't wager Charlie was any better off. Speaking of Charlie…Dean quickly figured out that she was one hell of a good kisser.

She broke away with a little giggle. "I'm not used to this," she said, stroking her hand against Dean's cheek, feeling the stubble there. Dean laughed.

"Think I've got a lot more than that that you're not used to." He paused, considering his words. "…..least not in the flesh and blood way."

If he wasn't mistaken, a flush had risen to Charlie's face. "Why, Charlie Bradbury, are you blushing?"

"No!" Her answer was immediate. "Besides…..thought we were gonna be working with borrowed equipment, here."

This time it was Dean's face that heated up, crimson creeping into his cheeks, making his freckles stand out. "Ah…..right."

Charlie gave him a little shove towards the bed. "Strip, Winchester."

There was something extremely sexy about the authoritative tone in her voice. "Yes, ma'am." He wasted no time in complying, toeing off both shoes and socks and shucking his pants, the whole time watching Charlie root around in her bag. With a triumphant "aha!" she emerged, and in her hands….oh God.

The strap-on was black and shiny, and bigger than Dean himself, and he was no slouch in the size department, if he did say so himself. Fuck. What've I gotten myself into?

Charlie cast her bra aside and Dean took a moment to take in the view. She really WAS gorgeous. He would say it was a shame she was a lesbian, but a relationship between the two of them would never work out. They were too close. Friends. This entire thing was like a game. A game where he was going to get brutally pounded in the ass. Right. Just a game. He felt a nervous fluttering in his stomach.

Charlie moved towards him, smiling. "Nervous, Winchester?"

"No." But even Dean could tell how defensive his voice was. Charlie just laughed.

"Hey. It's okay. We'll go slow." She put a hand on his chest and gave him a little shove. "Now on the bed. Hands and knees."

There was that bossy tone again, and the nervous flutter was replaced by that same wave of lust at the authoritative tone. He complied, kneeling on all fours. Immediately, he felt something wet against his entrance…..wet and extremely cold. He jumped. "Jesus! What the fuck…."

"Relax." Charlie ran a hand soothingly down his thigh. "Just lube. Help ease the way. Sorry. Should've warned you."

"Damn right," Dean grumbled, but he did relax….even if it only lasted a minute, lasted until Charlie pressed a finger into him, and he couldn't help but tense.

"Hey, it's okay. Just-"

"Relax, I know, I know." And honestly, after that it really wasn't that hard. It wasn't like it hurt. He'd been through way too much pain for something like this to hurt. It was just…..different. Charlie stretched him slowly, two fingers inside him now, stroking and teasing, and it was actually starting to feel good now when suddenly….

"Jesus!" Dean jumped as a jolt of pleasure shot through him. "Holy fuck what WAS that?"

"THAT, my friend, is why men do this." Charlie repeated the action, pressing her fingers against that sweet spot (prostate, some corner of Dean's mind reminded him), and he jumped again.

"Fuck! Holy shit okay, fuck, now. Fuck me." He was dimly aware of Charlie giggling behind him at the ferocity of his demand but he couldn't find it in him to give a damn. All he knew was that he wanted more of that pleasure and he wanted it NOW.

"Okay, then. If you insist." And then there was pressure, splitting him, an edge of pain throbbing through the pleasure as Charlie pressed into him, breached him, the head of that strap-on brushing against his prostate as she buried herself completely within him.

He shuddered at the sensation. "Fuck," he whispered.

Charlie leaned over him, a hand running through his hair, the other stroking his belly. "You good?"

Dean's response was to thrust back against her, wanting more. "Yeah, I'm good. More. Give me more."

Charlie laughed, surprised but amused. "Okay, Dean. You want it so bad, I'll give it to you." And she did. The next few minutes were a blur. Since the day he lost his virginity, Dean hadn't thought there could be anything better than sinking his cock into a tight, wet pussy, but this? With each thrust, Charlie was turning his world upside-down, managing to rewrite everything he knew or believed about sex. He couldn't begin to imagine what this would be like with someone he cared about. Somehow a pair of deep blue eyes manifested themselves in his mind and he was coming harder than he could remember coming in…God…..forever.

He collapsed onto the bed, breathing heavily. His heart and mind were racing. He realized that he had just thought of having a relationship with someone he slept with. When did he ever do THAT? And those eyes…..where had he seen those eyes before?

Charlie suddenly flopped down beside him and he looked at her. She was smiling at him. "You really got off on that one, huh."

Goddammit, how many times was he going to blush tonight? He punched her shoulder. "Shut up."

Laughing, she punched him back. "You should be thanking me. I totally rocked your world."

Dean couldn't help laughing despite himself. "Okay, okay. Thank you."

Charlie smiled smugly. "You're welcome."

A thought suddenly dawned and Dean frowned. "You…did you?"

Charlie nodded. She wriggled out of the strap on and held it up to show Dean the inside. "Vibrator."

Dean was impressed. "Now that is a fine piece of machinery."

Charlie grinned. "I've always been a fan." She stretched, folding her arms behind her head. "So…..how do you feel about lesbian sex now that you've seen the non-porny, more realistic side of it?"

Dean took a moment to consider. "Far more interesting. And definitely less-stagey. Though I didn't get to see it with a second girl. Do I get to watch you with a second girl?" Charlie smacked his arm; Dean just laughed.

"And what about the second part?"

Dean feigned ignorance. "What second part?" Now that he was coming down from that post-orgasm high, he was beginning to feel a bit more awkward about what had just happened.

Charlie gave him a Look. "The gay-sex part."

"Oh. That." He took another moment to think this one through, weighing his words. "…..well, I'm definitely a fan of this prostate thing."

Charlie grinned. "I thought you might be."

"And…" he didn't know what else to say. He was not about to admit that he had gotten off on the thought of being fucked by another man, let alone a man he was actually DATING. That was just not going to happen. "…and that's it."

Charlie just looked at him. She clearly knew there was more to that answer. "So….what about doing that with another guy?"

"Hey, I have an idea! Why don't we sleep?"

"Dean!"

"What."

"You're not answering me."

"Nope." Dean pulled a pillow up under his head, fluffing it.

"Okay. I'm just going to assume that your evasion means that you're gay."

"WHAT?!" Dean shot up off the pillow to stare at Charlie, mouth agape.

"Yup. It's okay," she said soothingly. "I'm gay, too. No judging. Safe room."

He glowered. "I hate you so much."

Charlie grinned. "I know." She curled up into the pillows, seemingly at peace with the way Dean stared down at her.

"….I'm not gay," he said at last. Charlie cracked an eye open at him.

"You can be gay, straight, or bi, Dean, it's all the same to me. I'm going to like you just the same no matter WHAT you are. When you figure it out, you can tell me, or not. No matter what, you're still you, and I still love you."

Her words mollified him, somewhat calming the raging storm of uncertainty within him. "…..thanks, Charlie."

She smiled. "No problem, Dean." She closed her eyes, and after a minute, Dean followed suit. It wasn't long before both of them fell asleep, and if Dean's dreams were haunted by messy brown hair and big blue eyes, no one was the wiser.

~THE NEXT DAY~

"Mmph?" Charlie blinked away, looking up. "Oh. Morning, Dean." It suddenly seemed to sink in that they were in bed together. Naked. She sat up abruptly. "DEAN?!"

"Uhh….yeah."

"What…..did we? We didn't. Oh my God we did."

"Yeah." Dean handed over more blankets so Charlie could cover herself up. "I've been trying to piece together the events of last night."

Charlie looked around them, taking in the disarray of the room, the strap-on and lube within reaching distance. "…..well, clearly we fucked. And judging from this…." She waved in the general direction of the toys, "I'd say I fucked you."

Dean winced. "Don't SAY that."

"You know it's true."

"Yeah, I know it. It doesn't mean I want to HEAR it!"

Charlie cringed apologetically. "Sorry."

Dean shook his head. "I just….I need a moment, okay? I need to think this through….try to remember what happened."

They both fell silent, thinking about last night, recalling the events. Dean flushed as he remembered exactly what happened. How they laughed, how the whole thing had been his idea…..how he had begged for it. Most of all, how he had come thinking about some man. He didn't even know WHO. All he could picture was a pair of blue eyes and yet somehow he knew that they belonged to a man. Fuck.

Yet somehow, it all seemed okay. Other than the thought of that man, it didn't seem all that bad. This was Charlie. They'd just been goofing around. Harmless fun, right? But you got off thinking of a man, a little voice whispered. He shoved it down. He didn't want to deal with that. The rest he could deal with. The rest didn't even really NEED dealing with. Harmless fun. It seemed weird that he could think of it that way, but he could. And looking at Charlie, he could tell that she was feeling the same. He felt a wave of relief that things weren't going to be weird.

"We're good, right?"

She smiled, clearly relieved that they were on the same page. "We're good."

"Awesome." After a moment, Dean picked up his pillow and walloped her over the head.

"Ow!"

"THAT'S for fucking me in the ass."

"Oh, you were BEGGING for it."

"Tch, details."

Dean found himself being hit over the head with a pillow, Charlie laughing as she got hit in return. Things were as easy and playful between the two as they had always been. Dean was relieved that their evening hadn't changed their relationship. Somehow things devolved into a violent (if somewhat naked) pillow fight, when they were interrupted by a knock on the door.

"I got it." Dean yanked the sheet off the bed and wrapped it around his waist. He pulled the door open and immediately froze.

It was Cas. Dean didn't know how he found them, but he had. A pillow connected with the back of his head but he barely felt it. He was too busy staring into Cas' eyes.

Blue. So very, very blue.

He was so totally fucked.

~tbc~

During a drunken night at the bar, Dean confesses to Charlie that he's curious about homosexual sex. So like any good friend, she shows him what it's like to be on the receiving end of things. Only then he realizes it might not be all curiosity. And why does he keep thinking in particular on one pair of blue eyes?