Dirt Box Cowboy

A gentleman who is a bit light in the Loafers, who is also an avid member of the Cheesy Wheelbarrow Pushers Club.

While playing cricket over the weekend I was asked if I'd bat for the other team. "no way!" I replied. "I ain't no Dirt Box Cowboy".

by Adlof Hilter February 28, 2023

Nautical cowboy

Sex on a jet ski in cowgirl position while on the ocean

After I rolled her from her starboard side, she rode me in the nautical cowboy till the seals came home

by Nickrad158 July 27, 2018

Blowfish Cowboy

Closeted married men who often preach their straightness to their friends but can be found at gay orgies typically in the cowboy position

You hear John’s wife caught him at a gay orgy? I had no idea he was a Blowfish Cowboy!

by Crinklecutcucumbers July 18, 2023

cowboy parked

parked completely sideways, as if you have never seen a parking lot before.

He cowboy parked the fuck out of that truck. Damn near in three different parking spots.

by big bear941 April 12, 2014

Michigan Cowboy

Sexual Position Involving 2 people roleplaying their idea of what Cowboys from Michigan would do.

Have you tried the Michigan Cowboy with your new GF? It’s so much fun.

by Michigan Man Handler March 26, 2022

Memphis Cowboys

THE BEST DAMN PAL TEAM IN THE LEAGUE

Memphis cowboys are so good.

by #70 always blocking January 17, 2025

Wantagh Cowboy

A big burly bad boy who is equally comfortable in a saloon or camping in the 'Daks.
He knows that everyone wants to be an outlaw until there is outlaw shit to do. Armed with that information he still attends country music concerts on a regular basis at Mulcahy's and Jones Beach. He meanders along the Wantagh Parkway and Sunrise Highway aboard his trusty steed Rav4 or square body pickup. Dreaming of a class B.
He will whisper or shout while telling you a story in excruciating detail.
If you run across him tread lightly,
kindly purchase him a cadillac margarita, tip your hat and mosey on along.

The saloon doors flew open and coming in hot a figure entered. We all gasped, it was the "Wantagh Cowboy"!
He sauntered up to the bar, his bride at his side with empty six shooter hands and shouted, "Yee Haw" while ordering a Cadillac Margarita. "Don't forget the triple sec he exclaimed."

by Days1 June 24, 2024