Dean didn't think the befuddled look on Castiel's face when he'd gotten them both kicked out of the brothel would ever stop being funny. "So, Cas, tell me again what that chick said?"

Castiel just slumped further down into the passenger seat. "I don't want to keep going over this."

Dean was going to have to mark tonight down as the day he'd learned angels could blush. "Okay, okay, you're off the hook." He pointed to the bag sitting between them; he'd only planned on splurging on one classy bottle of booze but the clerk working the overnight at the liquor store had bought his lie that it was Cas' birthday and given them a nice deal. "We'll start the party back up once we get back to the motel. Trust me, you drink enough of this stuff you won't even remember what she looked like." Castiel didn't answer and Dean glanced over at the passenger seat; he'd been confused in a generally good-natured way when they'd made the run for it but he'd been quiet since, even for him. "You okay?"

Castiel kept staring into the darkness beyond the window. "You don't have to entertain me for the next seven hours, Dean."

Dean felt that twist around in his stomach. "Dude. Of course I do." He'd been trying as hard as he could to put dawn and archangels and everything else breathing down their necks out of his mind, the last thing he wanted was Cas dwelling on it. "So we still got seven hours 'til dawn, huh?"

"Seven hours, ten minutes and thirty-eight seconds."

"You are just the life of the party, Cas." Dean pulled into the motel parking lot and hustled him into the room; he pulled the bottles out of the bag and looked around for glasses (there weren't any, which wasn't much of a surprise) and watched Castiel sit on the edge of the bed, looking like he wanted to avoid touching anything. Which Dean couldn't exactly blame him for, considering the state of the place. "Here," he said, opening one of the bottles and handing it over. "Drink up."

Castiel knocked it back and downed half the bottle in one long swallow, not bothering to so much as glance at the label. He smacked his lips when he finally came back up for air, lines tight around his eyes. "That burns quite a bit."

"Yeah," Dean said, taking a much more human-sized swallow from his own bottle. "You're gonna want to pace yourself."

"Dean?" he said after a few quiet moments, and Dean couldn't get over how he wasn't so much as slurring. "What exactly did I do wrong?"

"Thought you didn't want to keep going over it."

"When I make a mistake I prefer to understand why."

Dean drummed his fingers against the side of his bottle. "Well, bringing up her old man was a pretty terrible start."

Castiel looked away. "I wanted to set her at ease."

"Dude, this is her job. Trust me, she was plenty at ease. You were the nervous one." Which Dean supposed was partially his fault; so much time had passed since he'd been a nervous virgin he could barely remember there was such a dark time. There was more to being a wingman than just putting a girl in front of someone and Dean realized he'd fallen down on the job.

"What should I have said, then?"

"You should've..." Dean sighed, parking his bottle on the nightstand and taking Castiel's from his hand. "Okay, let's try something." He sat Castiel further back on the bed and draped his own jacket over the nearby chair. "You pretend to be the hooker and I'll be the john. This way, next time you're in that situation you can just do what I'm doing and everything'll go smooth."

Castiel frowned. "I don't know how to play that role any more than I did the other."

"Yeah, but we saw how bad you sucked at that. At least now you'll have a decent role model." Dean sighed again, straightening Cas' tie out of a loss of what to do with his hands. "Look, it's not that complicated. Use your imagination a little bit: you like your job, or at least you're good at pretending you do, you want to make me happy and you want to get paid. Think that's enough motivation?"

Castiel tilted his head to the side for a moment, as if he were considering that, then he nodded once, closing his eyes as he let out a deep, long breath, looking for all the world like a method actor getting into character. When he opened his eyes again there was an intensity there Dean had never seen before, one that made him feel almost as off balance as Cas had looked back at the brothel. "That should be sufficient."

"Um. Cool. Okay, so, the first thing you want to do is get down to business, make sure you both are clear what's on the table. It lets the girl know you're not the kind of creep who's gonna try for freebies. So, um..." Dean was having a hard time getting his thoughts in order with Castiel staring at him like that. "Okay, so, what's covered under your basic package?"

"I want to do everything in my power to bring you pleasure."

Well. Dean hadn't expected that. "All right, Cas, um...look, just so you know, most girls aren't going to say that."

"You said I could play the role how I pleased."

"Just wanted to make sure you knew." Castiel was pitching his voice lower than normal, the deep rasp turning into something thick and lush; all of a sudden Dean was having a hard time meeting his eyes and he didn't know what was wrong with him. "Okay, so the next thing..."

Before Dean could even finish the sentence Castiel stood up and kissed him, his lips a soft, steady pressure against Dean's. When he pulled back Dean felt the scratch of Cas' stubble and tried to follow after him for an instant before catching himself. "I think I should be telling you not to talk so much."

Dean hadn't expected the lesson to be quite so hands on."Cas...okay, again, just so you know, most pros don't kiss their clients, it's kind of a thing...

"I do." Castiel was still standing so close Dean could feel him breathing. His lips twitched up, his voice softening as he broke character for a moment. "You don't get to play both roles, Dean."

Dean knew there was a line here they were dancing all over but in that instant he didn't remember why he was supposed to care. And anyway, learning how to kiss was at least as important a life skill as proper brothel manners. "Okay, then." This time Dean initiated the kiss, one hand along Cas' jaw to hold him steady as Dean coaxed his lips open. He backed Castiel toward the bed again as he gradually took the kiss deeper, the first touch of Cas' tongue hitting his spine like a jolt of lightning. He could taste a lingering hint of the alcohol and something deeper beyond it, like tasting the air after a lightning storm. He'd never kissed anyone who tasted like that and Dean felt it sink down into his skin and fill up his veins like a drug.

He pulled back and this time Cas was the one left staring. "Dean?" he whispered, the word rough-edged and breathless. "Are...are we still pretending?"

"Yeah. Yeah, this...all part of the lesson, Cas." Dean didn't think he'd ever told a bigger lie. "Okay. So. Most girls wear a lot less than you are but if you're nervous undressing them's a good way to get that under control." God himself knew Dean could use a little help with that right now. "You want to start with the little stuff first and work your way in, untying ribbons, taking off gloves if she's wearing them, take off her stockings," he said, sliding Castiel's coat off his shoulders and unknotting his tie, the band of silk sliding through his fingers. "Well, you can leave the stockings on if you want, sometimes that's pretty hot too." He hesitated before touching Cas' belt but finally slid that off, too, the way Cas leaned back to give him better access not helping the building pressure in his groin at all. Soon the suit jacket was on the floor next to the trenchcoat and tie and Dean couldn't get over how different Castiel looked without all of his layers on.

"I think you're supposed to disrobe, too."

Dean was still working his way up to that. "You first," he said, starting in on the shirt buttons. "One being naked while the other's still dressed is one of the hotter things out there. Doesn't matter which is which, both are awesome." Dean grinned, unable to help himself. "Besides, maybe I want to see what I'm buying."

Castiel inclined his head at that, that phantom smile flitting across his face again. "Whatever you desire, Dean." He leaned back on his elbows and Dean finished with the buttons and let the shirt hang open. "You want to make sure you get her into it, too. The point is for both of you to have a good time, remember that." He trailed one hand down Castiel's chest by way of example, the way Cas' breath caught short circuiting his brain for an instant. "See? Like that." He slid the shirt off Cas' shoulders and threw it down to the floor, fighting the urge to rip it off him; he finished tracing his fingertips down to his waist, forcing himself to take his time, letting himself sample each inch of that exposed skin. Dean worked open Cas' pants button and undid the zipper with exaggerated slowness, pulling everything down past his hips and off, discarding the last of his clothes away with the rest.

Castiel lay back on the bed, as if he wanted to make sure Dean got the best possible look. "Do you like what you see?" he asked, and Dean had no idea how he was making his voice sound that sultry.

"You know I do," he bantered back, ignoring how the words shook as they came out. He trailed his thumb over his curve of his hip then knelt over him, grinding against him just enough to make Cas arch his back. He pulled Castiel back up into another wet kiss, trailing more kisses down his neck and lingering at the hollow of his throat, tracing the curve of his collarbone with his tongue. "How do you like that?"

Castiel was so hard he didn't need to answer. He gave Dean an up and down look that didn't need words either and Dean grinned as he pulled his shirt over this head. Castiel pushed him back and undid his jeans himself, the way those long fingers of his brushed against his cock in the process making him shiver. Castiel paused with Dean's jeans and underwear still only half off, running his fingers back over Dean's cock like he'd discovered something new and fascinating. "Is that what you want from me?" he said, looking up at Dean and he had no idea when Castiel had learned to leer like that.

"Good start," Dean said, more breathless than he'd intended. He kicked his clothes the rest of the way off, shorts, socks and all pressed Castiel back against the bed, needing to feel nothing but skin separating them.

Cas rolled him over before he could blink, straddling him with his hands on Dean's shoulders for a long, appraising moment. "You're very attractive, Dean."

Dean rolled his eyes. "You're gonna have to polish your flattery if you want the big tip."

"I don't flatter."

"Cas, all hookers flatter..."

Dean felt Castiel press one finger against his lips. "I don't. You are. From the first moment I saw you there was nothing I wanted to look at more. In Heaven or on Earth."

There was really nothing to say to that. Castiel bent down to kiss him again, stretching himself against Dean like the skin contact was all that was sustaining him. He began to slowly work his way down Dean's body, tracing every inch of his skin with his lips and tongue, his eyes trained on Dean's face. The hyper-focused attention was so overwhelming it was all Dean could do to breathe. "You're not being paid by the hour, y'know," he said, feeling the nervous joke fall flat.

Castiel's lips just twitched up again. "I want to make sure you get your money's worth." Dean felt Castiel's hand wrap around his cock. "Is that what you want me to do?" he said, that impossible leer back in his voice.

"I...yes, but...I mean, it was good before, too," he said, groaning as Cas trailed his thumb around the head of his cock.

Castiel pressed back against him, the tip of his tongue trailing along the curve of his ear. "Tell me what you want me to do," he whispered, his hot breath making Dean's back arch up. "I'll do anything you wish."

"Fuck, Cas."

"Soon enough." Castiel worked his way back down, lips and tongue and teeth all combining to turn Dean inside out as expertly as if he'd done this thousands of times until finally Dean felt his tongue lick up the length his shaft. "Never mind. I think I can guess what you want."

Oh, Jesus Christ."That's kind of advanced for the first lesson, Cas."

"I want to try. Let me try." Dean nodded and he didn't think he'd ever seen Castiel actually grin before. Castiel tilted his head to the side, like he was plotting out a mode of attack, then before Dean had time to take another breath Cas deep throated him in one smooth motion, his eyes still locked on Dean's face.

Dean groaned as he felt his head snap back, clenching his hands into the sheets. His vision whited out for a second when Cas began settling himself into rhythm and seriously, Castiel had no business being so good at this. He had Dean on the edge in seconds, but before he could finish the job Dean pulled him back up into a sloppy, needy kiss, glad to feel that as hard as he was shaking Cas was still shaking harder. "Thought you wanted me to get my money's worth," he said when he thought he had his voice back under control.

"Was that not worth your business?"

Dean kissed him, trying to force his head to clear. "Cas, trust me, you go pro with that and you'll be rich before you can blink." He rolled Castiel to his back, trailing his fingers over his lips. "The lesson's just not over yet."

He kissed Cas before getting up and going back to his jacket, fishing the little bottle of lube out of his pocket and so thankful he'd forgotten to throw into his bag when he'd bought it the day before. He spread Castiel's legs open and slicked him up, sliding one finger inside and reveling in the soft whimper that drew from Castiel. "Most of the girls will have lube next to the bed," he said, working his finger in an out of that tight heat. "You won't always need it but it's better to have more than you need than not enough. You don't want to be too rough. Y'know, unless she's into that. You into that?"

Castiel just moaned again, his eyes wide and lips parted. "That's what I thought," Dean teased, speeding the rhythm up just the slightest bit. "Most girls charge extra for this but some are really into it. Even then, you want to go slow," he said, licking up Castiel stomach as he kept working him open. "Besides, you said you wanted me to get my money's worth. Right, Cas?"

Castiel nodded, whimpering again as Dean kept fingering him, learning exactly what made him shake and moan and writhe. "Dean. Dean, please," he whispered, another breathy moan shaking the words.

Dean wasn't sure Cas even knew what he was begging Dean for, just that he needed more. Dean kissed him, feeling him already gasping for air. "You know what's gonna get me my money's worth, Cas?" he whispered, watching Castiel's eyes go so wide. "Fucking you until I get to watch you come."

Cas groaned at that and Dean had never see anticipation like that in someone's eyes. He moved his hand away and put Cas' legs over his shoulders, arranging his hips so the head of his cock could just press against him. Cas moaned like even that was almost more than he could take. Dean took a deep breath to steady himself and pressed in that first inch.

Castiel's whole body arched and Dean held himself still. "Now you wanna go slow with this," Dean said, aware he was teasing now but unable to help himself. "If it hurts you're doing it wrong. Y'know. Unless you're into that." He started rocking his hips, working himself in inch by slow inch as Cas started whispering his name, over and over at the end of each breath. "Just like this, Cas."

He felt Cas shake when he was finally all the way inside, his hands clutching onto Dean so tight Dean thought his nails might be drawing blood. Dean didn't think he'd ever been so hard in his life. "Now some girls fake but you don't do that, right Cas?" he said, rolling his hips into a slow rhythm to get them started.

Castiel shook his head, moaning again when Dean started to pick up the pace. "Don't forget to use your hands, too," he said, wrapping one hand around Castiel's cock, already slick with precome. "That's important." Castiel was already beyond words, his head tossing on the pillows and his skin glistening with sweat, so flushed he was almost glowing in the moonlight. Dean realized there was nothing on Heaven or Earth he'd rather look at, either. "Come on. Come for me, Cas," he whispered, going harder and faster the closer he felt Castiel get to the edge. His eyes locked with Dean's, dilating to deep blue rings as he mouthed Dean and please and other words Dean didn't know, words he didn't think any human on Earth knew. Dean pumped his hand up his cock one more time and Cas moaned so deep Dean almost felt it instead of heard it, his whole body shaking as he came over Dean's hand. Feeling that heat pulse around him was almost more than Dean could take and he only had a few seconds to absorb the desperate, breathless sounds Castiel kept making before he came so hard his vision blurred.

He lay himself down next to Cas and wrapped himself around him, kissing behind his ear as the aftershocks of the orgasm shivered through him. "You good?"

Cas twisted around to look at him, his eyes wide blue circles. "Yes. That...that was very instructive."

"Yeah, I'm an awesome teacher." He shifted over and pulled Castiel on top of him, Cas too spent to even turn over. "So here's the plan. When we finish kicking your dick brother's ass at dawn we're gonna go back to that brothel to celebrate. See what you've learned."

Dean wasn't sure Castiel had even heard him for a second. "Will you watch? To be sure I don't make a mistake again?"

Dean felt himself getting hard just at the thought of that. "Pretty sure they'll charge us double but I think I can cover it."

"Good." He leaned against Dean, his eyes fluttering. "I feel much better."

"How long 'til dawn?"

He shook his head. "I've lost track."

"Exactly what I want to hear."

Castiel managed to prop himself up on one elbow, tracing along Dean's lower lip. "Do you think we have time for another lesson before dawn?"

Dean kissed him again, one hand on his waist to pull him back close. "Think we can work something out."