A/N: This was supposed to be a legit Destiel fic but I started feeling really awkward writing it so it became a fanfic detailing the awkward first attempt of Destiel love-making. Enjoy.

Dean wakes up in a shitty hole of a motel room, hardly remembering how he got there. He must have gotten hammered the night before, because all he can remember is tossing back drinks like a man fresh off the wagon. The curtains are shut over the windows and the room is dim, which he thanks whoever is in charge upstairs for because his head is throbbing dully at the moment.

He's not fully dressed and lying on top of the covers of the bed, like usual, but rather he had been stripped down to his boxer shorts and tucked neatly in. He looks to the other side of the bed but no one's there, and the bed on the opposite side of the room is empty too. With how drunk he'd had to have been to black out and feel as crappy as he did now, there's no way he could have gotten back here himself, let alone strip off his clothes and fold them delicately on the chair beside him. And furthermore, Sam wouldn't have undressed him in the first place.

"Hello, Dean."

Castiel is suddenly leaning over him, his face pulled into a serious, unemotional mask as always. Dean jumps and nearly pees himself, and actually looks down to make sure he didn't.

"Jesus Cas," Dean says breathlessly, settling back into the pillows. "You scared the cannolis out of me."

The archangel merely tilts his head, regarding him with a slightly curious look. There is a long, awkward moment of silence in which Dean looks back with what he would admit was a small amount of nervousness.

"Were-" Dean clears his throat, "Were you the one who took my clothes off?"

Castiel sniffs and averts his eyes. If Dean wasn't still a little drunk, he would say that he saw the tiniest bit of color spill into his guardian angel's cheeks.

"Well Dean, I didn't want you to get overheated. You were sweating profusely."

The way Cas's eyes shift around while he talks, and yet manage to look everywhere but him tells Dean that everything that he just said was a straight up lie. And Cas knows he knows that, but decides not to bring it up.

"Are you thirsty?" Castiel says instead.

"Yeah, like a fish out of water."

A glass seems to appear from out of nowhere into Castiel's hand, and he offers it to Dean, who sits up to drink it. He chugs the water, and as he reaches over to set the glass down on the bedside table, the covers fall away. When he glances up, he sees Castiel staring dreamy-eyed at his chest, lips slightly apart, and his breath hitches.

Dean smirks, and is about to ask if his greedy-eyed friend likes the view, but the angel mumbles something and then disappears with a swish of his wings. It's disheartening, really, to see the weird little guy go.

The door to the motel opens a moment later, and Dean realizes why Castiel left in such a hurry. Sam strolls in, carrying a bag of groceries.

"Sammy!" Dean cheers, causing his little brother to look up, startled. "Did you get me some pie?"

Much later, in the middle of the night, Dean is awoken by a hand covering his mouth and a hot breath in his ear, shushing him. He can see Castiel's form outlined in the moonlight, as well as his wide blue eyes that glisten like jewels. The angel motions for the door, and then disappears with another fluttering of wings.

Dean gets the gist, and creeps quietly out of the room, only cursing once as he stubs his toe at the foot of Sam's bed. The big moose of man doesn't even stir, and Dean wonders how his brother ever got by as a hunter with how heavy a sleeper he was.

Castiel is waiting outside by the Impala, standing awkwardly with his hands in the pockets of his overcoat.

"What is it, Cas?" Dean asks gruffly. He didn't like being awoken by almost being smothered.

The angel looks up from staring at his shoes, and Dean is heavily surprised to see that his cheeks are flushed a deep, deep red. He regards the hunter with uncertain yet hungry eyes, and it's all enough to make Dean's throat dry.

"Perhaps it's not as important as I thought," Castiel said suddenly, scuffing his feet on the asphalt and looking down again. "It can wait until morning."

Dean feels a surge of urgency, and he grabs the back of Cas's neck before he can fly off again. The elder Winchester dips his head down and catches the angel's soft pink lips in his own full ones, and tastes cherry lip balm. He laughs in his head, surprised that Cas had actually prepared for this, but he's even more surprised because it reminds him of pie and that turns him on.

Dean moves his hand to the blue tie around Cas's neck and uses it to pull the angel flush against him, their bodies meeting in all the right places. He deepens the kiss, and Castiel stiffens as if he's about to pull away, so Dean twirls his tongue around the other man's and pushes him up against the back door of the Impala.

Dean yanks the tie off and throws it behind him, and after he undoes the buttons on Castiel's shirt he starts sucking on the newly exposed skin on his neck. Cas makes the most beautiful sound when he does that, and it shoots straight to Dean's groin.

"I don't know if we should be doing this Dean," Castiel says breathily, suddenly trying to slip down and away from Dean's administrations. "We're out in the open like this-"

Dean pulls away reluctantly and sighs. "Cas, we're in an abandoned parking lot in the middle of the night. And even if they could see us, why the hell would they approach?"

Cas blinks. "Maybe they think I'm getting mugged."

With a roll of his eyes, Dean reaches around the other man and yanks the door open, pulling Cas with it so he pushes up against Dean's body. Dean moves them around the door, then shoves Castiel back so he lands with a thump in the back seat of the car.

"This is much better," Castiel says, touching the black leather upholstery fondly. "Very comfy-"

His breath catches when Dean climbs in over him, positioning both hands on either side of Cas's head. He then starts undoing Castiel's belt, like it's the most natural and logical thing in the world, all the while staring into the angel's eyes.

"You know this is my first time, right?" Castiel asks around the lump in his throat.

Dean unzips Cas's pants. "Yeah, I'm well aware."

"I was just making sure you knew, because-"

"You're kind of ruining the moment here, Cas."

"Sorry, I'll stop talking."

The Winchester sighed and paused in his undressing of the nubile angel. "You don't have to stop talking, just don't talk about... that."


Dean starts sliding the pants down Castiel's hips.

"It's lovely weather we're having."

"Yeah, sure, the weather's great," Dean says hurriedly. He starts kissing Cas. It's a win-win, because he can get Castiel to stop talking and taste his cherry lips some more.

Castiel is just starting to get into it, is moving his tongue around Dean's and putting his hands on Dean's chest, but then he feels a hand down his pants, grasping at his genitals.

"Hot mama!" Castiel exclaims, pulling his face away from Dean's.

But then the hand is gone, and Dean is crawling back out of the car.

"I can't do this," the Winchester says. He's standing outside the car now, hands out in a gesture of defeat. "I just- I can't."

Castiel props himself up on his elbows as he watches Dean walk away back towards the motel room. "Another time then!" he calls out after him.