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Sol Campbell Gamble 

You're in a room. Five doors. Behind four are your dream women who will let you do anything you want. Behind the other is a raging Sol Campbell. Chained up for months and ridiculously horny, he will do whatever he wants to you for however long he wants. Do you take the Sol Campbell Gamble?
Would you take the Sol Campbell Gamble?
Sol Campbell Gamble by ill.matic January 28, 2015

greasy grundle gamble 

A sexual endeavor in which the woman applies lube to her grundle (aka gooch, taint). The penis is then rammed forcefully into the midpoint of her grundle (equidistant from the anus and vagina). The gamble that ensues is legendary, in which the penis slides into either the vagina or anus.
The greasy grundle gamble is irreversible; once fate has chosen a hole, you must stick with it for the remainder of the intercourse.
I took the greasy grundle gamble with Shelley last night; it was my first poopydick!

grunt gamble 

When you place a bet on whether you have gas or need to take a shit.
Each time on the shitter is a grunt gamble when you get to be my age!
grunt gamble by Dr Bunnygirl August 3, 2019

Lang's Gamble 

Committing a crime so you can go to prison just to get laid.
"dude you hear about Mike?"

"No"

"He ran naked into a church and shit on the altar"

"Wtf why?"

"It was a Lang's Gamble, he figured he'd go to jail and could find a man to sleep with."

"Bold move"
Lang's Gamble by TimesAreToughMan December 29, 2020

5am Gamble

Risk taken under the influence of alcohol very late at night, often during sleepovers, sofa crashes and slumber parties: while feeling reckless and uninhibited, the gambler will make a pass at someone either completely unavailable or way out of their league. The gambler will usually not be successful in their enterprise.
'I took a 5am Gamble last night. Still woke up with my clothes on though.'
5am Gamble by Jalfred Peacock November 20, 2009

losing the gamble

An alternate description of the term shart. An unintentional emission of feces during intended flatulence.
I was taking a piss the other day and tried to fart. It sucked, dude--I totally lost the gamble!
losing the gamble by bscepter February 12, 2005