coattail cowboy 

One who excels at the act of coattailing. A professional coattailer.

After my presentation, the coattail cowboy was trying to take credit for my work.

coattail cowboy by MowMow February 3, 2015

Russian cowboy 

When a female is bent over the toilet throwing up, a gentlemen puts his genitals into her

I Russian cowboy' d the shit out of her!

Russian cowboy by Bloodymary12 March 20, 2017

going cowboy 

Going against the rules or set of norms. Breaking the mold, usually in a spirited or rebellious manner. Similar to "going rogue". Often times reckless or careless in their pursuits.

"Why do we have so many office supplies? 2000 red pens? 500 boxes of staples? We only have 10 employees!"
"Bob from accounting must be going cowboy with the credit card again."

going cowboy by Pappa Wayne May 23, 2019

Smoking Cowboy 

When you put the butt of a cigarette in your urethra and a little cowboy hat on the head of your penis and flex your penis to exhale smoke from your urethra.

Damn Dave I could really rip off the drawers and go for a smoking cowboy if you have a cigarette on hand.

Smoking Cowboy by PinkVaquero July 29, 2019

crane cowboy 

A person that has the skills to pay the bills when it comes to heavy lifting and shady rigging principles. This person has the shadiest rigging technique and can sneak it by an osha inspector and usually wears a cowboy hat hard hat.

That Larry is a serious crane cowboy when it comes to gettin shit done, all he needs now is a mic ultra and his horse

crane cowboy by TyroneJefferson February 22, 2021

nullagine tandem cowboy shitwank 

Whilst one man is having a standard shit wank, a second man sits on his lap cowboy style and shits between his legs, whilst simultaneously jerking them both off with theirs cocks pressed up against each others

I was having a sneaky shitwank when my man lover Plunky sat down on my lap and joined me for a good ol nullagine tandem cowboy shitwank of monstrous proportions. We simultaneously owned the toilet whilst setting off jizz fireworks all of the bathroom ceiling

nullagine tandem cowboy shitwank by Bumfluff June 25, 2014

Drugsto Cowboy 

A popular internet blogger, vlogger, and music video comedian, The Drugsto Cowboy is the self-proclaimed "most color-coordianted rapper to ever come out of Sheboygan, WI."

The Drugsto Cowboy has more game than a Jewish Community Center on BINGO night.

Drugsto Cowboy by Ross Bailer January 4, 2009