Gypsy cowboy

A homosexual prostitute

That Gypsy cowboy sure was a cheap screw.

by Wild and wet December 11, 2021

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Bitmoji cowboy hat

If your named Finn you should definitely never wear this or wear the matching overalls.

Bitmoji cowboy hat should only be used if your wearing the matching overalls.

by Happysow May 18, 2021

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When a group of men each ejaculate into a pair of boots then randomly select one of the men to chase the others while wearing said boots until eventually catching one and shouting “Philly Cowboy”. The one who is caught then has to repeat the cycle and the game goes on.

This game originates in the streets of Philadelphia (1960s), however it is less popular there now. It is most popular in cities such as: Albuquerque, New Mexico, and Chicago, Illinois.

“Hey guys, who's down for a few rounds of Philly Cowboy?”

by Philly Cowboy lover May 8, 2022

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