by Dominic Bone February 27, 2005
When you are having sex with a woman who is on her period and cum inside of here causing the blood and cum to mix to make it look like the inside of a cherry pie.
when your girlfriend is cool enough to let you do this. Or wife. It's meant to be nasty so I'm not so sure you'll ever get to do it since a Cherry Pie Filling requires you having to stir the paint.
by Skrimp Weiner March 15, 2014
by frodaddy March 03, 2005
When you are giving a girl a blumpkin in The Johnny Bench style and she doesn't tell you she's on the rag.
Dude I was givin this broad the a blumpkin and it turned out to be a blumpkin cherry pie, I freakin puked!
by Bonglajio August 10, 2006
What is leftover or the remains from having sex and blowing your load inside a female with heavy menstrual flow.
The cherry pie payload after that sexual storm looked so much like cherry pie someone could confuse the two.
by Bvalds February 07, 2022
when a guy sticks his penis in a girls vagina while she menstrates on his penis then atempts to give him a blowjob
by Jacob Meier February 15, 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