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1. cornholing
Butt-fucking; anal intercourse; penetrating the rosebud with one's prong.
Captain Pissgums and his pervert pirates were always cornholing one another and anything else that moved.
by octopod Jun 13, 2004 share this
2. Cornholing
the secret meaning behind the song "Ride Capatin Ride" by The Blues Image. this song continues to talk about men going up to San Francisco to travel on "another shore," meaning the anus. The "Captain" is riding a mystery ship which means he is cornholing his fellow gay(sticking it up the butt that is).
"Dude, this song is about sea travel, I'm telling you."

"Shut up Kyle, its totally about a dude cornholing 73 other guys while calling his dick a Captain."
3. cornholing
the official activity of jails and prison showers
YO!!!, stop cornholing me. FAGGOT
4. cornholing
the act of sitting in such a way, on purpose, that your penis slips in between your butt cheeks and you have to fart to pop it out. When done by accident, it is just called corndogging.
John is such a pervert he was cornholing at his own wedding.
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