A guy who's well versed in seeking and attaining the pleasures of the tight female bootyhole. Typically their tactic is to sneak in a St. Louis shocker ("accidental anal") and never call the girl again. Can also refer to a homosexual.
Jason: I totally slipped it into Alyysa's brown eye last night when we were having sex!
Paul: No way dude, that's four in one week. You're becoming a regular bootyhole bandit!
Karl: That new guy at work, Jake, seems pretty cool.
Tim: I dunno man. I hear he's a little limp wristed. Possible bootyhole bandit.