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Dean was pretty much an amateur at "gay sex" until he got with Castiel, in his too attractive vessel. The first time he'd kissed Cas had been an accident. Seriously, Dean hadn't intended for it to happen. Castiel was confused at first as well, but it wasn't like he was ignorant to the way that worked. Meg, then April kind of proved that. Thankfully Sammy had been out on a beer run when Dean had tripped like a chump, only to be caught by Castiel and connecting lips with the angel. Dean had been utterly aghast and had grumbled about personal space for the twenty minutes Sam took to get the pizza. He was not prepared to admit he had kind of liked being in Cas's arms like that.
The second time they kissed Sam was in the room, but it was no accident. Castiel had apparently talked to Sam about it, who claimed to be their number one "shipper." Castiel had brazenly grabbed Dean's shoulder from behind and turned him to face him. Castiel had grabbed Dean's jaw and kissed him, good and proper like the pizza man, not allowing Dean to move an inch from where he stood. While Dean was sleeping Sam changing his background to that pathetic excuse for a lip lock.
Obviously there had been many more kisses following that one, not a one of them initiated by Dean. He was a little ashamed for liking it. John had made it clear he didn't want no fag for a son really early and it just kind of stuck with him. Castiel never lost patience with him.
It took four months for Dean to admit to having (maybe, sort of, just kidding, not really) a crush on Castiel, as childish as that sounded.
Six months after that, Dean allowed himself the indulgence of having that kind of comfort from Cas. He'd let Cas watch over him as he slept, something he hadn't really liked at first, but Cas took pleasure in seeing Dean asleep, but not in a perverted, tape it and beat off kind of way. More like a protective pride. Mary always said angels were watching over him. He allowed himself to play with Castiel's hands or stand too close to be platonic. Castiel always had a secret smile whenever Dean indulged in this behavior.
Two months later had a case that knocked Dean's dick in the dirt, metaphorically of course. Castiel had been worried, like an army wife, and had kissed Dean hard, full of tongue, teeth, and desperation. It wasn't the best kiss in skill but it was the best in passion. Dean had never felt that before. Castiel had healed Dean's wounds and kissed where each one had been. His neck, shoulders, collar bone, chest, and thighs were rained with kisses. Dean was blushy and embarrassed, but he didn't try to stop him. He would not look at Castiel for three days after that. He couldn't do it without blushing like a school girl with a crush. Sam thought it was hilarious.
A year of cute flirtations and (mostly) innocent kisses and neither had pushed for further. Dean was sick of it and ready to grab life by the balls, or in this case Castiel.
Dean was making like he was getting ready for bed, knowing Castiel would be along soon to watch over him. Dean brushed his teeth changed out of his jeans, opted for his gray shirt and sat on the bed, waiting for Castiel and a heavy dose of courage. Castiel showed and gave Dean a chaste kiss. Dean wasn't having it, so he gripped Castiel's face and wouldn't let him go. Castiel kissed him deeper, but slowly pulled away, lips making a wet sound as Dean whimpered.
"Dean, are you alright?" Castiel was worried, confused by Dean's enthusiasm.
"No, now shut up and lay down," Dean demanded. Castiel did as ordered and let Dean straddle him. Dean rocked his hips back and forth, hands popping the buttons on Castiel's shirt. He didn't care about the trenchcoat and suit jacket yet. He wanted to taste Castiel's chest. He leaned down and licked from nipple to nipple, teeth scraping the muscles in his pecs. Castiel's hands found their way to Dean's bare knees and slid up to grasp his firm thighs, fingers feeling the taut muscle.