Lucky Bastard by Jason Starr from the anthology Expletive Deleted
Jason Starr's Lucky Bastard has the feel of a Donald Westlake short and the twist ending of a Twilight Zone Episode. Jerry is a 54 year old shlub drinking away in a bar, when the most amazing looking woman he has ever seen slides next to him and lays a sob story on him. Faster than you can blink they are in a hotel room and then--- well that would be telling. The story carries a hint of comedy, a shot of hard boiled looserdom, and enough of a punch to carry the whole thing along. It's a fast read, but well worth the time.