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Corporate Cowboy 

Noun: an individual who works for money for the sake of money. Takes care of business for business' sake. Renegade working inside corporate ranks, fucking up all kinds of bottlenecks and complacency. Rocks the boat and follows the money. Takes "In God We Trust" to literally mean our, the royal "We", trust held in fiat currency. Will break rules AND take credit for it. Not afraid to catch flak. Cutthoat. Guilty by association.
Example 1
Person 1: Hey did you hear redacted got called to the 11th floor?
Person 2: Technically, redacted can't be called anywhere. They're an 1099- Independent Contractor.
Person 1: Fucking Corporate Cowboy. Probably stays cutting checks.
Person 2: Probably stays breaking necks. "Earn your keep, if you know what I mean..." haha

Example 2
Person A: Since when is a work day 8-5? WTF happened to 9-5?
Person B: "Right-to-Work", bud.
Person A: WTF is "Right-to-Work?" What happened to "Fire-at-Will?"
Person B: You need approval to fuck with Rules of Engagement. Corporate War and all. Can't just lick potshots all willy-nilly.
Person A: Fucking ay, man. Corporate Cowboys don't have to deal with Chains of Command. Are they hiring?
Person B: They don't hire. They only fire. Hahaha
Person A: Haha lit
Corporate Cowboy by el socio October 10, 2018
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Honolulu Cowboy

You’re a fuckin honolulu cowboy
Honolulu Cowboy by Poopvagina March 18, 2019

The crazy cowboy 

When a men ties his penis in a knot, and spins around with two fully loaded pistols in both hands
Hey mommy look i can do the crazy cowboy just like daddy
The crazy cowboy by Jhonny Turner August 27, 2009

Cinnamon Cowboy 

While penetrating a girl who's on all fours you reach for your cinnamon candle that's been lit a while. You then toss the hot cinnamon wax into her anus, grab her hair and hold on for the ride. A cowboy hat and chaps are optional.
Yeah Shasta hasn't called me back since I gave her that Cinnamon Cowboy.
Cinnamon Cowboy by Jedi 007 October 12, 2005

pink cowboy 

a gay who gets anal from equestrians
that guy loves his horses so much he is a pink cowboy
pink cowboy by Anonymous October 9, 2003

Thristy Cowboy 

The cupping hand posture similar to a thristy cowboy drinking out of a river, but instead the hand cups the genitals of either sex.
"Seth looked like he was taking a long drink of water with that thirsty cowboy move on Tara."

"Did that guy just give you the thristy cowboy on the dance floor?!"
Thristy Cowboy by DezNutsTsNuts April 20, 2009

space cowboy 

Sex position where the female ties her legs to a ceiling fan, spins in circles nude, and the male has various attempts to pork her.
My woman was too fat when we tried the space cowboy, and the fan broke.
space cowboy by Derek Allison January 17, 2005