Demon, 1940s AU. Because yes.
"Well, Salvatore, you wouldn't happen to know anything about vampires would you?"
The only thing Dean really needs to know is in that smile, the one that darts across Damon's face like the flicker of a shadow across light, quick and dangerous and disguised with insincerity.
"What's a smart guy like you doing sniffing around for bloodsuckers?" Damon responds, loathe to admit how curious he is to the truth behind that answer. "Besides, what would I know? I'm just your average private eye, Winchester."
The look that Damon sends him is all show and playfulness, an edge to it that gleams almost like a dare, like a challenge. That kind of thing might work on a pretty little dame, hell, even a lesser man, but no way in hell is this slick son of a bitch going to fool him. He's torn between wanting to punch him or drag him into the back room of the bar when Damon licks at his lips in an act that's nothing short of obscene.