Disclaimer: SPN is not mine

Dean strolled back into the broken-down house they'd appropriated, grin still plastered on his face, leaving Castiel to shut the door behind them.

"I swear, you're the only guy I know that couldn't get themselves laid in a whorehouse," he said, mostly to himself, as he sat down at the wobbly table next to the window. Castiel sat down across from him, the imitation of Dean's smile slipping off his face.

"I apologize."

"No, don't. It's no big deal. I got a good laugh out of it, at least, and we all know how much I needed one of those..."

The angel nodded, slowly, and turned to face the wall, returning to his plan of sitting there quietly the whole night. Dean had half a stubborn mind to let him, before coming to a quick realization that Cas was actually going to stare at the wall for hours, and deciding to avoid that scenario if at all possible.

"So...guess we're out of options, huh?"

Castiel glanced at him with his patented blank stare and tilt of his head.

"In regards to what?"

"You know. Getting you some action before you get smited, or whatever."

"We are?"

Dean raised his eyebrows.

"Unless you've got an idea."

Castiel opened his mouth to speak, but then apparently decided otherwise, shifting in his chair to turn slightly away. "No, I don't," he said eventually, running his fingers along the edge of one of his cuffs.

Dean's eyebrows didn't go down.

"You sure?"

"Yes, very," the angel said to his lap, continuing to fidget with his coat.

The hunter laughed, and leaned closer to Castiel, careful not to put too much of his weight on the unstable table that was already squeaking in protest.

"You got the worst poker face I've ever seen, Cas," he said, smirking, "What's this idea of yours?"

"If you haven't thought of it already, then I'm sure you'll disapprove."

"Try me."

Castiel looked up at him, face a picture of exasperation instead of the nervousness his fidgeting had betrayed.

"I thought you might do it."

Dean frowned.

"Do what?"

The angel shook his head, and turned away again.

"Wait," Dean said, leaning forward once again, the table creaking dangerously, "do you mean-"

"Yes. I'm sorry, I was mistaken."

"...oh. Well..."

The hunter sat back up, staring at Castiel with a faint look of surprise.

"Isn't that supposed to be some huge sin? You know, a man lying with a man and all that."

"No. That was a mistranslation. It was originally intended as a warning against pedophilia."

"Huh. Well, that's a relief."

Castiel glanced over at him.

"Why is that?"

"What? Nothing. Nothing, it's just..."

The angel continued staring.

"...actually, the hell with it. I've slept with a couple of guys before. Maybe six or seven, ever since Dad stopped following me around during hunts. So, you know. I'm already going to hell, but it's nice to know that I didn't ruin it for the rest of those pretty faces."

"Really?" Castiel asked, obviously intrigued, "Then why do you only ever show interest in women?"

Dean shrugged.

"I just like chicks better, mostly. And, well...Sam doesn't know about it..."

"Do you think he'd disapprove?"

"Uh...well...no, actually. It's just a little...it feels like I'm doing something wrong."

"You're at peace with hunting near-human creatures, but not with sleeping with people of the same sex?"

Dean smiled somberly.

"Yeah, I guess that's pretty ass-backwards."

Castiel shrugged, and turned back towards the wall.

Dean remembered the plan and was once again determined to interrupt. And also a bit inclined towards...something else.

"So, well…I do like keeping promises to my friends."

The angel quirked an eyebrow at him.

"So if you're really okay with screwing me, then, well...I don't mind. You got yourself a pretty face."

"I would much rather it be you than a woman that I've never met before."

Dean, to his annoyance, felt his face go slightly red. But he got a hold of himself and just hoped it wasn't apparent in the dark room.

"Alright, I guess," he said, standing up, "let's go find a place with a bed that isn't about to rot away."

Dean ended up spending a bit more money than he really needed to, getting a room for the whole night since he didn't really trust any of the pay-by-the-hour places that were hidden around here. Actually, he plain just didn't trust those places in the first place, no matter where they were.

And if Cas didn't want to lose his virginity in a whorehouse, then dammit, Dean was going to get as far from a whorehouse experience as possible.

Or, well, maybe that wasn't quite true. He drew the line at rose petals and champagne.

"Come on, Cas."

He ushered the angel to the motel room, trying not to betray his nervousness. Fucking a guy was once thing, taking his virginity was something else-and having to teach him basically everything about sex during the process was just going to be plain uncomfortable.

But, Hell. He said he wasn't going to let Castiel die a virgin, so he was not going to let Castiel die a virgin. And if this is what it took, then so be it.

"Hey, so," he started, placing his jacket on the table in the room, "if you don't mind me asking...where's Jimmy Novak in all this?"

"Sleeping," the angel answered, eyes sweeping the room, presumably for anything demonic in nature.

"Is that a good thing?"

"It's not ideal, but I did what I could. I've sent him pleasant dreams."

"Huh. Okay. So...uh...he doesn't really...know what you're doing with his body, right?"

"That's correct."

Dean sighed in relief.

"Good, or else this was gonna get real complicated."

As it was, he walked over to the angel, who was standing in the middle of the room, looking...well, he was a bit harder to read than he had been at the so-called "Den of Iniquity", but Dean was fairly certain he was nervous.

The hunter placed a hand on Castiel's neck, thumb inadvertently resting over the artery that betrayed a pounding heartbeat.

Well, that made two of them, then.

Dean leaned in and kissed him-but the angel flinched.

"Hey. Something wrong?" the hunter asked, putting distance between them once again.

Castiel's response was the shake of his head, but Dean wasn't about to believe that.

"No, come on. This isn't going to be very enjoyable if you're not honest with me."

"It's not important."

"It is. Tell me."

Cas sighed, and glanced away, but quickly decided that he should probably trust Dean in this matter. He was the expert, after all.

"I'm...nervous."

Dean, to the angel's surprise, smiled.

"Of course you are. I was my first time, too. Don't worry, I won't rush you...and if you want me to stop, just say the word."

Cas found himself being kissed again, and this time stood his ground, though stiffly.

"I don't know what to do," he mumbled against his partner's mouth.

"Just start out copying me, then do whatever feels comfortable. I'll lead, you just have to...participate."

And with that, Dean went on 'leading' his angel. It was predictably rough sailing for a minute or so as Cas was trying to wrap his head around the concept (and his mouth around Dean's) and Dean was trying to figure out what effected the angel the most (which was ridiculously difficult to do considering Castiel's relative lack of response, but every so often there'd be a twitch or a shift that let Dean know he was on the right track), because Dean was intent on making this as great for Cas as possible.

But, to both of their surprise, Castiel figured out Dean first-somehow managing to tilt his head just the right way and scraping his teeth against the hunter's bottom lip, moaning deeply and softly in a way that went straight to Dean's crotch, prick twitching against his zipper as he let out an involuntary gasp-one that he wished he hadn't, since Cas quickly broke away.

"Are you alright?"

Dean didn't answer-just grabbed Castiel, threading his fingers through his dark hair and kissed him harder, wondering why oh why he didn't do this to people with stubble more often.

"That wasn't-my 'stop' noise," he explained in between kisses, "that meant-'do that again'."

"Oh," was all that Castiel managed to get in, before Dean picked him up and relocated him against the wall, shoving his tongue down the angel's throat-which was a lot more pleasant than Cas would have guessed by the phrase.

"This...is a very odd sensation..." the angel mumbled, as soon as Dean leaned back to catch his breath.

"Yeah? What's up?" he panted, sincerely hoping he hadn't done anything wrong. Currently he was in no state to deny that he sure as Hell wanted to do this again one day.

Castiel looked down.

Dean followed his gaze.

And, sure enough, both were sporting erections-to the hunter's pleasure and apparently, the angel's confusion.

Well, Dean decided, now was as good a time as ever to show Cas what this whole thing was all about, and positioned himself correctly before grinding up with his hips, hard, creating as much friction as he could through the fabric of their clothes.

He was expecting a moan, a gasp, something, but all he received as a reaction was a small squeak, though the angel's bright blue eyes grew wide and dilated, betraying himself. So, Dean slid his leg between Castiel's, and nibbled down his neck gently, trying to stay aware of reactions. Again, more twitching, though this time accompanied by the angel's shortening of breath and reddening face.

"Not good?" the hunter inquired against soft skin.

"No, you're...you're excellent."

"Then make some noise, would you? There aren't any people in the rooms near us, promise."

"I...just feel like it's indecent."

Dean grinned, and slid a hand under Cas's shirt, making a mental note that the button-down would have to go soon.

"It'll feel better for both of us if you try and let it go."

The angel gave a nervous nod, swallowing hard.

"Alright. I'll try."

So, Dean scraped his short nails down Castiel's stomach, kissing and nibbling at the skin under the angel's loose collar in order to leave his mouth free for any expressions of ecstasy he wished to communicate. For his troubles, he received a quiet humming of pleasure. Well, it was something. Maybe it was time to kick it up a notch.

The hunter undid Castiel's pants with practiced precision, and slid his calloused hand down, stroking the angel's length just hard enough to gauge a reaction. And a reaction he did get-Cas's hands bunched up in his overshirt, fabric tearing due to unchecked strength as he let out a quiet, shy moan. Dean found himself relieved that he'd had the mind to take off his jacket beforehand.

"Excellent," he encouraged, placing more kisses on his angel's mouth, now turned up in a slight smile.

"I see now why you're so fond of this," Castiel said.

"Yeah? And we're not even at the best part yet."

Dean hoisted Cas up, and moved him the small distance to the bed, placing him down not as gently as he could have-but neither cared at that point-, crawling over him and wasting no time in unbuttoning the angel's shirt and loosening his tie enough to pull over his head, ruffling his already messy dark hair.

Why haven't I done this already? he thought to himself, though he may have said it aloud, before kissing a trail down what he'd exposed of Castiel's body, leaving a mark or two on his neck and pausing to tease at a nipple-was that a freckle above it?-and being slightly surprised at Cas's initiative when he felt the angel not-so-smoothly slide the over shirt off of Dean's shoulders.

Obliging, the hunter sat up and removed it, pulling his shirt off while he was up there-though he might have prolonged it a bit for Cas's benefit. There certainly was no doubt that his angels eyes were glued to him, watching with undisguised interest.

And, well, trying to disguise his interest wouldn't have done much good with Dean practically sitting in his lap, anyways. It was fairly obvious by now.

Leveling the playing field, Dean slid the layers of fabric off of Castiel's shoulders, the angel pulling his arms out and laying back down, eyes still fixed on his partner.

"Feel free to touch," the hunter reminded him, enjoying the attention. And, to his surprise, Cas did-tugging him down and kissing him again, hands wandering over Dean's torso-and Dean let him satisfy his curiosity, at least for the moment. That is, until his hands wandered a bit too far, and decided to take a page from the hunter's book, slipping past Dean's waistline and squeezing.

"Oh, God," he groaned before he could stop himself, resisting the urge to press himself against the hand, instead glancing at Cas's face and noticing the angel's raised eyebrow and faint smirk. Well, then-a challenge, was it?

Obviously he'd gotten over his inhibitions.

Dean shifted downwards out of the angel's reach, and tugged Cas's pants off, boxers quickly following-and wasted no time in licking a line up his already oozing dick, relishing in the moan that he finally pried from Castiel's throat.

"D-Dean," the angel gasped, knotting his hands in the sheets, looking like he was just about ready to slip over the edge.

"Yes?" he answered, removing his own underwear and biting back a comment about Cas being way too sensitive. He was a virgin, after all-he'd have to make an exception, just this once.

"This is-you're amazing."

"I know."

Dean slid his tongue between the angel's parted lips, kissing hard enough that it might have left bruises on any normal person, and ground his hips down on Cas's, his angel bucking up on instinct and causing them to groan into each other's throats.

Castiel cursed-either muffled beyond recognition or in a language Dean hadn't learned, though the meaning was clear enough-and scraped his nails down the hunter's back, pulling them together close enough to feel his partner's pounding heartbeat against his own and lifting his hips up against the other's.

This time, Dean didn't resist the urge. Their erections slid together, the hunter gripping a hand around them to guide their instinctive movements and watching Castiel's eyes shut and his mouth gasp for air erratically-if it had been anyone else, Dean might have been worried they would pass out-and god it turned him on so much more than it should have; so much that when Cas, a virgin, hit his climax, Dean was right there with him moments later, sent over by what he could only describe as a whine that parted from his angel's lips-a pleading moan about an octave higher than anything Dean had ever heard emerge from that particular mouth.

The hunter lazily rolled onto his back afterwards, sticky from sweat and cum and brain muggy with the afterglow, a lethargic smile spreading across his face.

He glanced over at Castiel, who was staring back, expression once again unreadable.

"What's up?" he asked, though not particularly concerned at the moment. He didn't receive an answer; the angel just turned away, and after a moment, got up and walked out of his field of vision.

Dean closed his eyes, and listened to footsteps wander around on the motel room carpet. Well, the angel wasn't immediately getting dressed and disappearing, so obviously he'd done something right.

The faucet turned on for a few minutes before shutting off again. Then there were footsteps, a creak of the bed, and Dean felt a warm, damp rag drag across his abdomen.

He peeked an eye open, and watched Cas clean him off, slowly and gently, obviously exploring closer what he'd been allowed to before.

The scrutiny was almost enough to make Dean feel uncomfortable.

Almost.

"Thanks," he mumbled, closing his eyes and placing his hands behind his head.

"I could hardly let you fall asleep like this."

"Who says I'm falling asleep?"

"I do," Castiel said, and Dean didn't need to be looking to hear the smile behind his voice.

"Yeah, alright," he answered, not bothering to fight back a yawn. "What about you?"

"What do you mean?"

"We still got more than a few hours left before sunrise. You just gonna...sit there quietly again?"

The angel shifted slightly.

"I thought I might, yes."

Dean opened a disbelieving eye, and propped himself up on his elbows, staring at the angel.

"Well," he said, once again unable to read Cas's expression and not really awake enough to puzzle it out, "Alright. Do whatever."

And he let himself fall back onto the bed, folding his hands over his stomach and closing his eyes to sleep.

Cas stared at him.

Then he got up and placed the rag in the bathroom, and folded their clothes into neat piles, and really did sit around for a bit, before he became certain that Dean had fallen asleep.

So he crawled into bed next to him.

"...didn't have to wait so long," Dean mumbled.

"Ah," Cas said, frowning. "I thought you were asleep."

"I was."

"Oh..."

Dean glanced at him, meeting the angel's eyes, which didn't turn away.

"...well, come on," he invited, extending an arm towards Castiel, who took a moment to figure out what the gesture meant, but soon wiggled over and rested his head on Dean's shoulder, the hunter fighting to keep a straight face at the movement that seemed so odd coming from the stone-faced angel.

He wrapped his arm around Cas, and proceeded in his attempt to sleep.

"...Dean?"

"Hm?"

"I think I'd like to stay on Earth past the morning."

Dean raised an eyebrow, glancing at the angel who for once wasn't staring at him.

"Yeah? Regretting chasing that girl away?"

"No. I'd like to sleep with you again."

Dean blinked.

"Yeah...sounds good."