Top Definition
When a straight man, spends an entire night picking up an extremely sexy girl, and takes her home under the impression he's about to get incredibly lucky, starts fooling with her, goes down her pants only to find a massive cock.

Usually observed by a bystander, who laughs hysterically knowing the girl's shemale identity.
Jer: So what happened with that girl last night?

Dayo: Man, i brought her home, and found she had a fucking cock bigger than mine.

Jer: (Laughs) I know man, I Sheboozled you, pay back's a bitch fagget.
by JROC444 November 24, 2010

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