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Cowboy Decision

A brave, bold and sometimes reckless judgement call.
I pulled a cowboy decision and texted her a picture of my limp dick.
by Kahuna77 March 24, 2017
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cucumber cowboy

A HOMOSEXUAL MAN WHO ACTS VERY STRAIGHT BUT REALLY LIKES COUNTRY MUSIC AND COCK.
Burt a super nice guy to drink but beware! He's a real cucumber cowboy
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Cowboy

A rebel. A person that chooses their own destiny and pushes boundaries. A term coined by Shemar Pierre and his affiliates.
Virgil Abloh was a true cowboy, propelling forth the intersection between street wear and high fashion, paving the way for the future young creatives to come.
by NEXUS :: Discipline February 11, 2023
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cowboy speedrunning

A product development methodology where team focuses on delivering daily updates and improvements directly to users, sidestepping conventional processes like detailed task management, frequent meetings, and structured sprints.

It's typically adopted during critical phases such as the lead-up to a product launch or immediately afterwards. While effective in the short term for rapid improvements, extended periods of cowboy speedrunning can lead to burnout, increased technical debt, and potentially risky decisions.
In the past week, our team has adopted cowboy speedrunning. We've managed to rapidly address user feedback and issues, greatly improving their experience.
by pyyding March 20, 2024
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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
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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
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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
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