A female deliberately failing to tell a dude that she's on her period before he proceeds to go down on her.
"I was pissed off at him for that Strawberry Shortcake he gave me last week, so I gave him a Cherry Surprise."
by Rizzle213 December 29, 2006
while the male is positioning his penis between a womans heaving bosum and then he proceeds to ejaculate on the females face and then punches her in the nose and yells "surprise".
by matt oyler November 15, 2003
When a man anally piledrives a menstruating woman (preferably with a huge bush), shits in his hand (preferably behind his back so she doesn't see it coming), then smears the feces onto her bloody vagina and yells "SURPRISE!"
For their 35th wedding anniversary, Harold gave Eleanor something extra special; a black forest cherry surprise.
by luckypork May 5, 2011
When a man is screwing a woman while she is on the rag, and as he makes every thrust he says cherry, after a little while he quickly exits the snatch and enters her ass, at the same time yelling chocolate surprise.
by tunazz June 23, 2008
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