Emo Cowboy

A boy who wears cowboy boots, a cowboy belt, and a cowboy hat but is also tired and sad and shows no emotion. Also known as mike or mike & Ike

AVA: "look at mike & Ike over there, he is SUCH an emo cowboy"
CHASTER: "for REALLL"

by UglyRAtAYEE February 17, 2022

Lazy cowboy

Sexual position where both partners are lying on their backs with their heads away from each other. Essentially, the person riding cowboy stays connected, straightens their legs, and then lies straight backward onto their back. Good passive position when one or both people are tired or convalescing. Also an excellent position to sleep connected to your partner.

1: Hey babe I’m really horny - wanna have some wild sex?
2: Not right now, I’m really tired … but I’ll lazy cowboy ya.

1: you’re seriously not gonna believe this! He and I were so tired last night I just lazy cowboyed him, and next thing I know we are both waking up this morning still connected!

2: Holy crap that’s hilarious! I thought that only happened to us!

1: As funny as it is, I’ll tell you what - it was actually awesome sleeping and waking up like that.
2: oh I know, sometimes I fake being tired just so I can lazy cowboy my way into the next morning like that!

by PeckertonDetinktive February 24, 2022

Naughty Cowboy

When a gay guy dressed as a cowboy rides you whilst you thrust into his ass like theirs no tomorrow, it ends when your about to cum and the guy riding you screams “Fill me up Daddy”

Hey Ryan what’s up?
Not much
Do anything interesting last night?
Yeah, I found out that Tyler likes to be a Naughty Cowboy

by The Real Queer Cowboy March 4, 2022

Michigan Cowboy

Sexual Position Involving 2 people roleplaying their idea of what Cowboys from Michigan would do.

Have you tried the Michigan Cowboy with your new GF? It’s so much fun.

by Michigan Man Handler March 26, 2022

Philly Cowboy

When a group of men each ejaculate into a pair of boots then randomly select one of the men to chase the others while wearing said boots until eventually catching one and shouting “Philly Cowboy”. The one who is caught then has to repeat the cycle and the game goes on.

This game originates in the streets of Philadelphia (1960s), however it is less popular there now. It is most popular in cities such as: Albuquerque, New Mexico, and Chicago, Illinois.

“Hey guys, who's down for a few rounds of Philly Cowboy?”

by Philly Cowboy lover May 8, 2022

cucumber cowboy

A HOMOSEXUAL MAN WHO ACTS VERY STRAIGHT BUT REALLY LIKES COUNTRY MUSIC AND COCK.

Burt a super nice guy to drink but beware! He's a real cucumber cowboy

by The Original Uncle Filthy July 13, 2022

keyboard cowboy

Someone that goes FUCKING CrAzY behind a Twitter post or email or text but is totally harmless and rather sweet in real life.

The keyboard Cowboy walks in and says

“I need to see you immediately”. Walks into the room…. “Hi! How are things?!”

by silviasm September 2, 2022