A very short, often ugly
man, that for some reason can pull some serious ass. It could be because the
guy has legitimate game or he has a big sausage or a combination of both. Every college campus has at least
one pimpsqueak. Usher, Jeremy Piven, Prince, Joe Rogan and Jermaine Dupri are all perfect examples of pimpsqueaks.
Ron: "Is that
Mandy Harris kissing on that little ugly dude over there?"
Chuck: "How in the
fuck? I'd kill to bounce that ass."
Ron: "Why in the
fuck would that guy get her?"
Chuck: "What can you say, the guy must be a pimpsqueak."