Top Definition
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 June 13, 2004

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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."
by mycockismycaptain April 27, 2009

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the official activity of jails and prison showers
YO!!!, stop cornholing me. FAGGOT
by tatomuck1 March 26, 2009

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when you pick corn, and put the aformentioned corn in a random mailbox, and imagine the expression on the owner's face when they open their mailbox.
Chris Chris, dude, check it out, I cornholed at least 7 mailboxes last night!!! Going cornholing is the best.

Sick-nasty!!

yeah!
by piss up my ass April 16, 2010

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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.
by spider420 October 31, 2008

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