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Hole Caddie

One who is provide their hole (mouth or anus) to a single handler for pleasure or servitude.
Ben was Big Black Mike's hole caddie in jail for 15 years.
by Huncho Don August 7, 2025
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Hole In one

When you stand over a girl and jerk off and the the cum lands in her pussy mid air
Yo dude I made a hole in one in vanessa from the roof!
by bdriggy September 28, 2025
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Hole Ass

When somebody calls you an asshole, you can simply reply by calling them a hole ass. Thus flipping the insult onto them.
by ItzScenic October 16, 2025
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Hole Roulette

When you alternate between the ass and pussy hole and where you bust is a surprise.
Got that bitch drunk and played hole roulette.
by DLW 513 November 25, 2025
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Choke Your Chicken Up Your Charlie Hole

Bobby: Hey Dave, make us a brew?
Dave: How about you Choke Your Chicken Up Your Charlie hole!!
by Greg_the_Smeg February 7, 2019
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Hill Hole

A democrat who supports a neo con for president of the United States of America.
Don't blame me you smug Hill Hole, I voted for Bernie.
by OwenTate July 26, 2016
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Charlie Hole

Dave: Bobby, I've got a right itchy Charlie Hole
by Greg_the_Smeg February 11, 2019
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