Cowboi

A "cowboi" epitomizes the blend of vintage Western grit with contemporary urban charisma. These avant-garde trendsetters don cowboy-inspired attire, seamlessly merging the charm of the old West with the pulse of cities like New York, Boston, Austin, and Portland. Whether drawing from authentic ranching roots or crafting a unique metrosexual statement, their presence is unmistakable in hip clubs, bars, and streetscapes. Icons such as Elon Musk, Kacey Musgraves and Orville Peck might have ignited this movement, but cowbois are truly the vanguards of a new cultural frontier, where heritage meets innovation and tradition dances with novelty.

"Introducing their innovative tech product at the Austin expo, the team adopted a cowboi theme, blending the city's Western heritage with its modern tech boom, making a memorable impression on attendees."

by Gordon0022 September 24, 2023

Commonwealth cowboy

A "Commonwealth Cowboy" refers to men from smaller communities within Commonwealth nations (UK, Ireland, Canada, Australia, New Zealand) who embody a blend of rugged practicality and quiet confidence. They are typically sturdy and dependable individuals, known for their willingness to work hard and their genuine, straightforward communication style. Unlike those focused on image, they possess practical skills and a grounded nature, offering a sense of security and respect through their competence and kindness. This archetype represents a refreshing authenticity rooted in real-world abilities rather than superficial displays.

Woman: On our way to dinner, my date pulled over to change a strangers tire, just said, “can’t leave ‘em stranded”. I swear men from the prairies are built different.

Friend: sounds like he’s a commonwealth cowboy

by I H8 City Boys April 13, 2025

Naughty Cowboy

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

by The Real Queer Cowboy March 4, 2022

coldwater cowboy

Full time boat cruise captain, part time lumberjack, sometime supervisor.

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

Cowboy hug

When you bear hug another man and shape your two fingers and thumb like a gun to finger his arse

Don't make me give you a cowboy hug

by Shimoss March 30, 2023

bloody cowboy

When the time right, but time month is wrong. One must remove the tampon, holster it is as a lasso, and swing it around flinging blood everywhere, while yelling yeehaww ,thus resembling a cowboy lassoing a bull.

Omg Finley, no way you got with that trany last night

Finley: Dude I went bloody cowboy with her/ her all night

by meoooowowwwwwww May 29, 2025

Cowboy Freight Train

When a group of men engage in the act of standing in a line with a person both in front of them and behind them; as the line starts to progress across an area all the men involved simultaneously insert their penis into the anus of the man in front of them, place their hands on the shoulders of the man in front of them, and walk, dance, and thrust to the rhythm of the music that is playing.

Rules:
1) Making train noises with your mouth is encouraged but not required.

2) Women with strap-ons are allowed to participate depending on who is taking part, but it is always looked down upon.

Guy 1:"Hey man, would you like to take a seat?"

Guy 2:"Thank you, but I can't, me and a couple of other gentlemen had a Cowboy Freight Train last night and I'm afraid I won't be sitting down for a while."

by Jimbo McDoodle Snout November 22, 2011