When you fuck a girl's asshole until it bleeds.
Yea Becky... you are bleeding. I just cherry holed your ass.
by Guatamalan kunt nugget April 13, 2011
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The man inserts the tip or head of his penis into a butthole and the two precede to rotate their bodies in opposite directions until a 360 is completed. If the individuals are lucky a chocolate dipped cherry donut hole will occur and the partner must proceed to lick it off. Partners must be married. If more information is needed to explain this task please leave a post.
"I rocked a cherry donut hole last night."

"If you don't shut your mouth, I will give you a cherry donut hole."

"May I have a cherry donut hole please?"

"A dozen cherry donut holes to go please."
by thebaker125 July 30, 2009
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