walk the cowboy

Man wearing a cowboy hat while his female partner is holding his legs up and fornicating him with a dildo.

My boyfriend and I are going to walk the cowboy tonight! It was the first time I was in control!

by StellaNaughtBerry October 2, 2021

cowboy

a person who is reckless or careless, especially when driving an automobile.

"cowboy coach firms are alleged to have flouted safety rules"

by Arminkshipper July 19, 2024

Cowboy RyRy

This one sexy ass sex-worker

Yooo Cowboy RyRy is that bottom bitch

by Heyyuhhhhhh May 23, 2025

Cowboys Comeback

When the Dallas Cowboys lead their fans on by closing a large point gap in the fourth quarter, making it seem like they’re going to win, just to end up losing yet another game. Typically involves a stupid play call, bad call by a ref, or turnover.

Don’t get your hopes up, it’s probably just a cowboys comeback...

by NotACowboysFan October 4, 2020

Water Cowboy

One who is constantly on the water or wishes they were

You're just a real Water Cowboy

by Orange Crush July 11, 2017

cowboy up

( 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)

by Sexydimma April 24, 2021

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