$miley vs. Cowboy

Two people fighting like a madman or loving your friend so much that you fight them for stupid reason

Will:yo guess what's happening

Billie: wot?
Will:there's a fight going on $miley vs. Cowboy style

Ig:untitled_k2ng

Twitter:POPTARTS86

by POPTART$ March 10, 2023

Depressed Cowboy Syndrome

A hardcore republican with zero self-awareness. Usually has a chronic fear of girls from the goth community.

"Man that dudes corny as fuck he def got Depressed Cowboy Syndrome"

by $$Definition June 20, 2023

cowboy three way

A three way in which a mother and daughter are the females involved.

The MILF I met last night got mad at me for suggestion her daughter join us in a cowboy three way.

by Drock1954 June 25, 2017

cowboy tone digz

The hot sexy cowboy from the pat mcafee show

Pat Mcafee: One half of the hammer DAHN!, cowboy tone digz is here

by Fiendish end October 23, 2023

new generation cowboy

the new generation cowboy is a city slicker that says he's the hottest cowboy on TikTok he calls a donkey a horse, he also has frosted tips and drinks white claws and calls them beer, he has a Jeep and calls it his bad *bleep* truck, he makes fun of Taylor Campbell and thinks the the PBR is FAKE bull ridin there is so many things wrong with him I can go on forever

DO NOT BE A NEW GENERATION COWBOY

by someone.that.dont.like.joe April 9, 2021

job for cowboy

It is fucking hardcore

dude lets go mosh to a job for cowboy breakdown

by matthew 66676 May 29, 2008

White Saddle Cowboy

A sexual position in which a woman is on her hands and knees and a man is sitting on he back or giving it to her anally. To make it a side saddle cowboy the man pulls his penis out of the woman's anus and moves up her back and slides down her left or right side as she tries to buck him off like a bull. In the end the man cums on the underside of the woman's breast.

I did a white saddle cowboy with Cindy last night.

by BING BONG BROTHER December 2, 2009