Warnings: First time, threesome (sort of), fingering, oral, prostitution, exhibitionism

"This is a den of iniquity, I shouldn't be here."

But here they were, Cas being pulled away by a sexy girl who looked like she'd be better off hitting the books than the sheets. Cas' eyes screamed a silent "help me" as Dean slipped some money in his hand and watched him get dragged down the hall. He chugged his beer and followed behind them.

"That's it, baby, just lie down and relax." Chastity pushed Cas
against the headboard and climbed up between his legs, her hands running along his collar and playing with his tie.

"Your name's Cas, huh? Cute name." Cas could only nod as she worked the first few buttons of his dress shirt open, exposing warm, smooth skin. Her small lips pressed against his neck and Cas closed his eyes, took a deep breath and tried to calm the irrational nerves. Angels had sex all the time. Sometimes they even had sex with multiple partners at once. He shouldn't be so terrified.

Except he didn't want to lose his virginity to a girl who didn't want to do this anymore than he did. He had his eyes on someone else.

"What'cha thinking about, baby?" Chastity nipped at his earlobe, eliciting a nervous groan from the Angel. "You thinking about your friend?"

Cas should have seen that coming (mind reader that he is) but his thoughts had strayed so far from what they were doing, from Chastity's hand rubbing circles against his hip bone, that it took him by surprise.

"You know, the friend with the pretty, plump lips, just made for sucking cock?" The words sounded so weird coming from her sweet voice, but oddly enticing at the same time. "Maybe you're thinking about those strong muscles holding you against the bed as he takes off your clothes and runs his hands all over your naked body."

"N-no, I wasn't-"

"Shh, it's okay. Wanna know a secret?" She pulled his tie from his neck and brought his hands up to the bars on the bed, pressing his wrists together and slowly knotting the tie around them. "Sometimes when I'm in here being eaten out by some stranger I imagine it's my girlfriend's tongue fucking my pussy. I bet you think about your friend bending you over and fucking you until you can't even hear your own screams anymore."

Cas bucked his hips up, erection painful in his suddenly too-tight pants. Chastity giggled and yanked his shirt open, trailing a finger down his chest.

"I like you," she smiled softly. "He told me I would."

"Who told you?" Cas tilted his head in confusion.

"I did."

Cas' head snapped up to the foot of the bed where Dean was standing, belt hanging loose in front of his jeans and shirt opened wide, and how on Earth did he not notice Dean entering the room?

"Dean, what are you doing?" Cas felt his pupils dilate as Dean shrugged off his shirt and yanked his belt out of the belt loops.

"What I promised. Not letting you die a virgin."

Dean dropped the belt on the ground and climbed on the bed, quite literally crawling up to Cas. He paused in front of him, eyes roaming over the olive-tinted skin. He brought his hand up to the back of his friend's head, threading his fingers through the dark locks, and locked eyes with Cas. He was so close, Castiel could taste Dean's breath on his tongue, the odd combination of breath mints and alcohol, before those perfect lips brushed against his.

Cas melted in to Dean immediately, transforming the kiss into something more needy and intimate. Dean gasped softly, jaw falling open, and Cas let his tongue slip between Dean's lips to explore his hot mouth. Cas knew right away that he would never get enough of this, the feeling of Dean opening up to him and letting him have something he'd wanted for so long. Dean gripped his hair tight and Cas moaned as the sensation went straight to his straining cock.

"Oh, I think he likes that." Cas had forgotten that they had an audience. He unwillingly pulled away from Dean's lips and peaked over Dean's shoulder at Chastity, who had taken a seat in a chair at the foot of the bed. Her voice was a sweet, seductive whisper, as if she was trying not to interrupt but just couldn't help but comment, and Cas found that he liked the way she stared hungrily at the scene in front of her. She didn't often enjoy her job, this much he knew, but she enjoyed it right now.

"That true, Cas? You like it when I pull your hair?"

Dean pulled experimentally and Cas arched his hips against Dean, pushing their erections together. Dean groaned and slumped over slightly, going in for another kiss, this one messier than the last.

"Yes, Dean, feels so good." Every rational, angelic part of his being told him he shouldn't succumb to these feelings so easily, shouldn't lose himself in them, but he pushed those parts aside in favor of Dean grinding against him teasingly.

Dean kissed along Cas' shoulders and followed his lips down Cas' shuttering chest, over his belly button until he licked the V-shape lines of Cas' hips. Cas let his head fall, eyes locked onto his own hands where the tie was coming undone as Dean worked on getting him out of his pants, tongue dancing over his skin.

Cas pulled on the tie, wanting to have his hands in Dean's hair, pushing his head further down, but small, dainty hands stopped him.

"Uh uh, you have to keep them up until we say so," Chastity said, and Cas smiled softly at the way she said 'we' instead of just Dean. This was as much for her as it was for Castiel. "He told me you were strong and might need some reminding."

Chastity pressed her lips softly against Cas', held his wrists in place as Dean reached into Cas' underwear and pulled his cock out. Cas groaned against her lips but kept his hands still. Chastity pulled away, smiled as she tightened the tie around his wrists, and dragged the back of her nails smoothly over his cheek.

"You gonna be a good boy?"

"I-I'll be good, I promise." It was getting harder to think, what with Dean's hand wrapped around his length and his face so close, breathing hot air against him. Chastity winked and moved back to her seat.

"Oh, fuck!" Cas nearly ripped the tie clean off the headboard as Dean swallowed his cock in one swift movement. He pressed his shoulders hard against the headboard, a gentle reminder to keep his upper body in place, as Dean worked his tongue over the underside of Cas' cock even as it slid further into his mouth, teasing his throat.

"Dean, Dean, oh my God, so good..." Cas pushed his hips up without realizing it and effectively shoved his cock down Dean's throat. Dean gagged and pulled off quickly. He let out a small cough and smirked up at Cas.

"Careful, buddy, try not to choke me."

"My apologies," Cas said, eyes fluttering closed as Dean wrapped his lips around the head, tongue flicking over the hole gently, before he took Cas as far as his muscles would allow. Cas was surprised that it was further this time; he could feel the muscles of Dean's throat working to open up for him.

Dean bobbed his head, deep-throating Cas while still pushing his tongue over Cas' shaft. Wet, gagging noises filled Cas' ears and for a second he thought it was too much for Dean, but Dean was practically worshipping his cock, holding his hips down as he made Cas fuck his mouth.

"Think he's ready for the real thing?' Chastity asked, legs folded over each other in a seemingly innocent way. Cas could see how tight they were pressed together, though, and knew she must be aching from her own arousal.

Dean pulled off Cas' cock with a wet, popping sound and smiled bright at his friend even as spit and the first traces of pre-come glistened on his lips. Castiel couldn't take his eyes off that wetness, couldn't stop wondering what he tasted like mixed with Dean's tongue.

Dean grinned and leaned so close that his lips were literally two centimeters from Cas'. He made no move but his eyes were amused and challenging. Cas swiped his tongue along Dean's plump lips, a noise of approval slipping from his mouth as the taste hit his tongue, something bitter but not bad. The knowledge that he tasted his own arousal made him pant and push his mouth hard against Dean's.

"Yeah," Dean breathed when he finally pulled away, staring at the panting mess of a fallen angel in front of him. "Yeah, I think he's ready. So how do you want to do this, Angel?"

"How...what ways are there?"

Dean licked his lips and palmed Cas' thighs, pushed his legs apart.

"Well, I can sit on your lap and take you in my ass-" Cas' eyes became impossibly dark as he briefly imaged bouncing Dean on his lap, making the hunter clutch to him hard and moan like a slut. "-or you can spread your legs for me and find out how it feels to have a nice long cock inside you. Your choice."

Cas blinked several times, eyed Chastity who shrugged and bit her finger, and tried to think through it quickly.

He wanted to be inside Dean so bad, wanted to know how much hotter and tighter his ass was than his mouth. More than that, he thought back on Dean's plump lips glistening with spit and cum and just imagined what that would look like if it were his ass, the tight ring of muscles loose and smeared with Castiel's seed. But he didn't want to hurt Dean. That was the deciding factor in the end.

"Want you inside me," Cas managed to get out, though he barely recognized his own voice. It wasn't like him or Jimmy; it was more animalistic than he had ever heard.

"You sure?"

Cas nodded vigorously and Chastity left her seat again to pass Dean a bottle and something in a wrapper. Dean held it up to Cas with his eyebrow arched.

"Condom or no?"

"Not necessary." He noted the quizzical look on Chastity's face as Dean tossed the condom aside, no questions asked, but she didn't voice her curiosity. Dean reached up and - bless his soul - pulled the tie from Cas' wrists. Cas let his hands flop down on the bed uselessly. Now that he was free to touch he didn't know what to do.

"S'okay, come here." Dean took one of Castiel's hands and guided it to his opened pants. His boxers were visible, as well as the outline of his cock, and Cas brushed his fingers over the length gently at first. He had seen humans do this all the time but without any personal experience it was the equivalent of a human virgin watching lots of porn and then going to have sex for the first time: fairly useless.

"Doing just fine, Cas," Dean muttered when Cas' hand paused with uncertainty. Encouraged, Cas slipped Dean's bottoms down his legs enough to get his length out. His hand went to work immediately with slow, lazy strokes that had Dean keening.

"Ah, fuck, that's good!"

Cas let go and reached over for the bottle of lube. He gave Dean a quick peck on the lips before pushing the bottle into his hand.

"I'm ready."

Dean pulled Cas down the bed a little and spread his legs before he lathered his fingers in lube and brought one to Cas' hole. Dean knew preparation wasn't necessary for an angel, but Cas figured he wanted to draw the experience out. He pushed one finger in and Cas seized up instantly. His hips pushed down, forcing Dean's finger deeper inside.

"More, Dean. Want you to fill me," Cas gripped the sheets as Dean shoved another finger in and pumped them both. The rhythm was too slow for Cas' liking, so he braced his palms on the mattress and pushed his ass down, fucking himself on Dean's fingers.

"Looks like someone's got a power bottom on his hands." Chastity's soft, smooth voice melted perfectly with Cas' senses and made him gasp, even as Dean laughed at whatever she had just said. He made a mental note to ask Dean what a power bottom was later.

"Deeaan..."

Dean pulled his fingers out and lined himself up with Cas' needy hole. He was aching to feel how tight Cas was, too desperate to even bother with the jeans still clinging to his thighs.

"Ready to lose your virginity?"

"Yes, just, just- ahhhhh!"

Dean pushed his cock passed Cas' puckered rim and didn't stop there, sliding slowly inside him until his entire length was sheathed in Cas' tight channel.

"Holy shit," Dean gasped. Someone so tight shouldn't have stretched for him so easily. The combination made his head spin and he started pumping his hips. Cas grunted and accepted each thrust like it was to best damn thing he'd ever felt, but it wasn't enough. He used his hands once more to force his hips down on Dean's cock, meeting each thrust and making them that much harder and deeper, just how he needed it.

"C-Chastity..." Cas beckoned to her and she was sitting by his head in a matter of seconds.

"What do you need, baby?" She stroked his forehead, bringing her fingers through his hair.

"Pull his hair," Dean grunted, hips pumping fast and sweat dripping from his brows. Chastity grabbed a fistful of hair and yanked much harder than Dean had, but then, she did this for a living. Cas let out a broken moan and slammed down hard on Dean's cock, resulting in a scream that he barely realized came from his own lips. His cock jerked against his stomach, so close to release, but he never wanted this pleasure to end.

He had expected Chastity to talk to him, whisper dirty things in his ear, but she stayed silence, eyes locked on what Dean was doing to him, tugging on his hair at unexpected moments. Cas' senses were being pulled in every direction. His nerves cried out at the glorious pleasure shooting through his ass, at having Dean's cock work him over so perfectly, while his scalp tingled with each pull and the feeling went straight to his dick. He could smell sweat and sex in the air, could even smell Chastity's arousal so close to his face.

"Dean, fuck, so close, so close, ah!"

Cas felt his entire body spasm with such intensity that his eyes rolled back into his head and his back arched right off the mattress. Chastity pressed him down as he came over his chest and a little on her hand.

Dean kept fucking him, though, pounding against his prostate with shocking accuracy, and the overstimulation was making Cas cry, actual tears slipping down his cheeks as pleasure overcame him.

"Cas!"

Dean grabbed Cas' hips brutally hard and thrust his cock one last time, body shaking as he coated Cas' inner walls with his come.

"Oh god, oh god, oh god..." Dean fell forward, head landing on Cas' stomach and just barely missing a line of come. He sucked in huge lung-fulls of air as he came down from his orgasm, feeling Cas stir under him.

"Sorry," Dean laughed, pulling out slowly, grimacing at the sensitivity.

"No worries."

"Oh, isn't he precious!" Chastity brushed hair out of Cas' eyes and Cas grinned, pushing his face against her leg. He really was precious, caught up in that beautiful post-orgasm state that left a person temporarily immobile and looking around like they'd never truly seen the world before.

"Not bad for your first time, huh?"

Cas laughed and swatted at Dean before reaching both hands out. Dean pulled him up and they shared a brief, sweet kiss.

"Thank you," Cas whispered. Dean stroked his cheek lovingly.

"Any time, angel. I think we may have forgotten something, though." Dean turned their bodies to face Chastity, who had her legs pressed tight together again.

"Don't worry about me, boys. I enjoyed the show."

"You sure you don't want some help with that?" Dean inclined his head toward the crotch of her panties and she bit her lip, desire raging in her eyes. Dean grinned, mischievous, and turned to Cas. "Cas, how would you like to find out what a woman tastes like?"

The next thing anyone knew, Chastity was on her back, one hand stroking Dean's growing hard on as Dean guided Cas' head between her legs.

Possibly the greatest request I've ever received. Also, one of the longest fics I've written in a long time. And now I sort of have a weird fondness for Chastity. Anyway, please review, let me know what you think, throw any fic ideas you might have at me. I'm doing a writing challenge so I need all the inspiration I can get! Any pairings, any kinks, don't worry about me judging you cuz I won't. You could throw mpreg at me and I won't judge you. I mean, please don't throw mpreg at me, but still, no judgement. :) I'm castiel-sniffs-deans-panties on tumblr for anyone interested in checking out my blog!