Cherry Surprise 

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."

Cherry Surprise by Rizzle213 January 2, 2007

cherry surprise 

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".

my bitch called the cops after i gave her a cherry suprise last night

cherry surprise by matt oyler November 14, 2003

Black forest cherry surprise 

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.

Black forest cherry surprise by luckypork May 29, 2011

cherry chocolate surprise 

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.

Hey whats up with the black eye?
Oh, I gave my girl the cherry chocolate surprise

cherry chocolate surprise by tunazz June 23, 2008

cherry pie surprise 

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."

cherry pie surprise by Hank Thrasher January 26, 2007