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.
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.
by Philly Cowboy lover May 8, 2022
Get the Philly Cowboymug. “I saw Jamie wearing a guys hat when she was out on the town the other day”
“You know the cowboy hat rule - you wear the hat, you ride the cowboy”
“You know the cowboy hat rule - you wear the hat, you ride the cowboy”
by ClassyKit November 12, 2023
Get the The Cowboy Hat Rulemug. by The big phink January 12, 2019
Get the crystal cowboymug. by Eagles on top November 24, 2022
Get the Cowboysmug. 
A type of fetish where a male lays down naked and another male rides his shlong and the dude laying down jerks the male riding him until he creams
by Darianyen September 27, 2025
Get the Cowboys Ridemug. A type of police officer. Prefers large caliber revolvers, .44 Magnum for example, over the traditional semi-automatic handguns. Also uses a thigh or drop-leg holster instead of a typical duty belt holster. May use phrases such as, "If leather were brains, he wouldn't have enough to saddle a junebug" or "He's about as useful as a screen door on a submarine." A cowboy cop will usually be very "Rick Grimes-esque"
by Agent_007 November 23, 2014
Get the Cowboy Copmug.