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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

Words related to cherry pie surprise

cherry pie dirty sanchez gilad rusty trombone