Drugsto' Cowboy

A popular internet blogger, vlogger, and music video comedian, The Drugsto' Cowboy is the self-proclaimed "most color-coordianted rapper to ever come out of Sheboygan, WI."

"The Drugsto' Cowboy has more game than a Jewish Community Center on BINGO night."

by Dave Lahna December 31, 2008

Penis Cowboy

Somebody who rides the penis much like a cowboy rides his horse

Wow... look at tim cook... such a penis cowboy.

by TheFridgeMaster November 30, 2009

cowboy hard

Condition in which one worked so hard he can't get a full erection, but the callouses developed riding in the saddle makes the penis feel hard.

Mike: After all these years on horseback I think I may have given myself ED.

Jane: yeah but at least you're cowboy hard

Mike: *silence*

by Gonna Be Dumb, Better be Tough April 21, 2014

kotex cowboy

1. A person who is a pussy
2. Someone bitches a lot
3. A person acting in a cunt like manner

John is a Kotex cowboy today

by God's Gift To Electrical December 17, 2013

Yooper Cowboy

People from the U.P who dress in a flannel, work boots, and a Stormy Kromer while sometimes carrying a gun.

Yo what's with all these Yooper Cowboys lately?
You can tell when it's buck season because the Yooper Cowboys come out in full force.

by tilsby November 12, 2018

river cowboy

Rugged men who work on the inland river system- loading, unloading, and towing barges of cargo. They can tie a line, fetch a wire, and will work 365 days a year.

“Hey, It’s time to switch these barges out at the dock. I’m gonna need some river cowboys to help flip this load out and tumble one of those empties in”

by Flat Dick October 4, 2018

Steamroom Cowboy

A gentleman who enjoys loitering in steam baths in the company of other nude men, for any number of other reasons - mere voyeurism; the prospect of a good, hearty romp with another like-minded fellow; or possibly he wants to check out the other chap's todger to see if it matches the description of the one his wife has been playing around with.

When the Ambassador caught Alex hanging around the steam baths, peeking at stray John Thomases, he proclaimed him to be a "Steamroom Cowboy".

Naturally, the Ambassador thought nothing of keeping the photographs of this behaviour.

by Hangus the Monkey September 29, 2019