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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."
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An appellation used to describe an insignificant individual who would otherwise be labeled a "pipsqueak" but has stooped to such a level of personal or professional immorality that it would offend pipsqueaks.
That guy has gone way beyond the pale - he is a pimpsqueak for sure!
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