1.A guy who instead of having a dick he has a pude(pussy) in place of it.
2.A transvestite
3.The opposite of a chick with a dick.
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This phrase is the opposite description of male-to-female trannies, A.K.A. "Chicks With Dicks." The word pudendum describes a woman's external genitalia.
"Hey, brosef, what's up with that new student, Jack? He looks like a chick."
"Don't worry, broheim, he is one of those Dudes with Pudes. Jack used to be Jill."