Skip to main content

cotton cowboy 

Tampon or A compacted tubular-shaped piece of cotton with a plastic applicator that women and emo boys insert into their vaginas when they're having their period.
And she says, "Not this week honey, I'm visiting the cotton cowboy!"
cotton cowboy by pork pal January 22, 2011

enema-cowboy 

An actual password on an AOL trial disk back in the 1990s. An enema-cowboy is gay man who rides another man like a cowboy rides a horse and penetrates so deeply that it effectively impacts the bowels (like an enema).
Did you see that enema-cowboy?, He's got such a lisp and I heard that he rides Elton John like the wild stallion.

Cuddle Cowboy 

When two homosexual males take a shit on each others chests, then give each other a long shitty hug and smell each others shit.
Barri and morrie gave each other a cuddle cowboy, and then licked the shit off each others chest.
Cuddle Cowboy by Crisp June 25, 2008

rowdy cowboy 

A male is on top of a female having sex when a group of people rush into the room to startle them. The male tries to stay on the female for eight seconds while she is trying to get up. Just like riding a bull, hence the name rowdy cowboy.
The girl was startled when we busted into the room so Bill had to play the rowdy cowboy.
rowdy cowboy by Al Tonen April 5, 2004

IT Cowboy 

The act of a System Administrator or other IT administrator to implement any corporate-wide or district-wide change to a system without testing or appropriate forethought of downstream effects.
Wile E Koyochie - I pressed the button for the system change.
IT Friend - Did you test the change first?
Wile E Koyochie - No.
IT Friend - You're such an IT Cowboy!
IT Cowboy by Ketch005 August 21, 2020

gay reverse cowboy 

When a man is doing reverse cowgirl on another man;
the man is pointed upon the other man's penis, with his face and body facing the one whose penis it is' head. Usually, the man is bounced up and down, and it is VERY hot.
did you see that hot gay reverse cowboy porn video?! I cummed twice!