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3.
when you fuck a girl so hard she bleeds
Tom: i plowed susie so hard it was a cherry dip

Joe: Dude, that is such clown shoes
by Tobs July 10, 2005
 
1.
Sexual act in which a man gives a woman a pink sock, then she puts it in his mouth.
She cherry dipped me last night. . . .
by Phreak_Commander December 27, 2007
 
2.
Fucking a girl on her period but just with the tip
Hey baby even though I'm on my period will you cherry dip me tonight?
by HeyZeusey November 13, 2011