Top Definition
A cherry pie surprise is when you have sex with a girl who is on the rag while you have no idea. Made famous by some dude named Jake Daniels.
"Dude, I heard Jake got some cherry pie surprise from this girl named Jessica the other night. His dick was was covered in bloody pussy juice."
by Hank Thrasher January 23, 2007
4 Words related to cherry pie surprise

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