Milky cowboy

Cum cowboy

"Lij is a milky cowboy"

by monkeybuttsnutts November 17, 2021

Broken Cowboy

It's the reverse cowgirl position but two lesbians, where the one with a strap-on is on the top. (Thus "broken", because natural erect penises dont bend like that)

It's referenced a couple of times in House M.D.

House: "Hey Wilson, are you going to do the Broken Cowboy?"

Or...

Foreman: "Do you know what is a broken cowboy? It was on House's bachelor party requirements list... ... I hope she can do the broken cowboy"

by Dyke Biatch March 25, 2022

the cowboy hat rule

A rule made to keep people (ladies) from stealing your cowboy hat. If you wear a cowboy'hat, you have to ride the cowboy!

Well seeing as how you don't made off with my hat, your truck or mine in accordance with the cowboy hat rule.

Excuse me pretty lady, I assume since you're wearing my hat, you're ready to obey the cowboy hat rule!

by Elk_newbie July 8, 2017

A Cowboy's Dozen

to buy as much of a desired product as one can afford with the amount of money one is carrying.

Cashier: Can I help you?
Customer: I’ll take some of those one dollar scratch-off tickets right there.
Cashier: Sure, how many would you like?
Customer: A Cowboy's Dozen (throws money on counter)
Cashier: (counts money) Soooo, seven then?
Customer: I reckon.
Cashier: Good luck!

Could also be used to exaggerate a story:
Derek: How much money did he say he won on that bet?
Jeff: A Cowboy’s $300.
Derek: Meaning?
Jeff: $200

by iBetty January 10, 2012

Whoa there cowboy

Wait a minute! Consider all the risks before you just charge ahead.

The man wanted to jump out of the plane with his parachute, but the trainer said, "Whoa there cowboy" we haven't verified everything is working right on the checklist yet.

by tender vittles December 15, 2012

cowboy dan

a major player on the cowboy scene who goes to the reservation, drinks and gets mean, they say he'll start a war, he hops in his pickup puts the peddle to the floor and says "i've got mine but i want more" then he drives to the desert and fires his rifle in the sky and says "god if i have to die, you will have to die."
he didn't move to the city, the city moved to him and and he wants out desperately

"Cowboy Dan's a major player!"

by obie January 26, 2004

21st Century Cowboy

A man in a wheelchair, whether it be for a paralyzed individual or one with an injury.

Hey you know what we call people in wheelchairs these days? 21st Century Cowboys.

by dephn March 14, 2013