Based on Season 4, Episode 5 "Monster Movie"
Prompt: "Which leads me to conclude, sadly, that my virginity is intact" – Dean
He hadn't got it right the first time. It hadn't been disastrous or anything – in fact he'd probably given the girl the night of her life – but looking back, in hindsight and all that crap, he wished he could have saved it for someone special. Hell, at least for someone memorable. He was pretty certain she's had a name, he was less certain that he'd bothered to ask for it.
But here was a second chance – and if Heaven wanted him to use his awesome powers and underwear-model good looks for the sake of all people-kind, then who was he to argue.
Well, usually the first admittedly, although not in this case.
He didn't think God or His Angels would approve of what he had in mind, but Dean knew just where he was going to start.
And finish come to think of it.
He was reborn with the certainty that he was only going to sleep with one person ever again. Not that he was planning to turn celibate or anything after that, quite the contrary. He was hoping to have sex on a more than regular basis and, while it would no doubt take place in a lot of different motel rooms, he would not be sleeping around.
This was his opportunity to get it right. Now he just had to tell Sam about it.