A person (usually a man) riding on a horse he had in the back (🤠) wearing a cowboy hat, in a country vest with boots that's black to match.
* walking down the old town road*
person 1: "yo did you see that cowboi?"
person 2: "yeah! he had a noice hat!"
p1: "did he cheat on his baby?"
p2: "yeah, you can go and ask her!"
person 1: "yo did you see that cowboi?"
person 2: "yeah! he had a noice hat!"
p1: "did he cheat on his baby?"
p2: "yeah, you can go and ask her!"
by drinkyouryeeyeejuicekiddos May 29, 2019

A man with an abundance of joy in his pants. Men named Matt are often defined as such. Favorite positions are cowgirl and reverse cowgirl. Let the women ride until they're warm through before they hop off the saddle.
by horneeslutt69 September 27, 2017

When a gay guy dressed as a cowboy rides you whilst you thrust into his ass like theirs no tomorrow, it ends when your about to cum and the guy riding you screams “Fill me up Daddy”
Hey Ryan what’s up?
Not much
Do anything interesting last night?
Yeah, I found out that Tyler likes to be a Naughty Cowboy
Not much
Do anything interesting last night?
Yeah, I found out that Tyler likes to be a Naughty Cowboy
by The Real Queer Cowboy March 4, 2022

The "Coldwater Cowboy" is most noted for leaving a fiasco in his boat wake, a disaster in his wood chips and a few tears in the hoistway.
by SEABISCUIT797 July 10, 2024

A) verb, to- to get one's news from doc-med sources such as Facebook, Twitter, etc...
B) noun- the actual news that one reads on soc-med
B) noun- the actual news that one reads on soc-med
If you are a fan of a cowboy update definition b), and want to get a cowboy update definition a), please learn how to think critically.
by Sexydimma May 26, 2017

by Bdhuxjsbwvauisjxbch103 June 16, 2023
