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
Get the Naughty Cowboymug. ( an insult used between men only: to metaphorically 'grow an extra pair of balls' and take ones responsibilities like a grown man
Incompetent teen son: dad I got my girlfriend pregnant. What do I do?
Father: cowboy up and be a dad. And btw, I am busy ( slams door in son's face)
Father: cowboy up and be a dad. And btw, I am busy ( slams door in son's face)
by Sexydimma April 24, 2021
Get the cowboy upmug. 
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
Get the horny cowboymug. Uncertain; my guess: slang term to bypass YouTube filters? A red light district? Perhaps a particularly named district or night market?
by Boboodo June 13, 2024
Get the soi cowboymug. by cryptologies May 6, 2015
Get the moaning cowboymug. by Hulksta June 25, 2025
Get the Cowboy Sodamug.