The act of intercourse wherein a male-to-female transgendered "woman" anally or vaginally penetrates "her" partner.
Friend 1: "Hey, so that hooker you hired for my birthday yesterday wasn't really a woman...."
Friend 2: "What? You serious? That chick was smokin' hot!"
Friend 1: "Ya, that's why I let her stay and I fucked her. Who knew tranny was that good?"
Friend 2: "Wow, you must have been drunk."
Friend 1: "Very, that why she shenailed me."
Friend 2: "I bet that hurt...."
by GorgeousMoe December 18, 2008
11 Words related to shenailed

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