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A "Jack Dempsey" refers to one beating his meat very aggressively, as the legendary boxer Jack Dempsey flogged his opponents.
Dude, I got so excited over that midget porn I was watching that I stole some face cream from my sister's make-up bag and gave myself a "Jack Dempsey". Now my pecker is sore.
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A man who owes the majority of his fame to a fish.
I didn't know who Jack Dempsey was until I went to the "aggressive cichlids" shelf in petco