Cowboy Freight Train

When a group of men engage in the act of standing in a line with a person both in front of them and behind them; as the line starts to progress across an area all the men involved simultaneously insert their penis into the anus of the man in front of them, place their hands on the shoulders of the man in front of them, and walk, dance, and thrust to the rhythm of the music that is playing.

Rules:
1) Making train noises with your mouth is encouraged but not required.

2) Women with strap-ons are allowed to participate depending on who is taking part, but it is always looked down upon.
Guy 1:"Hey man, would you like to take a seat?"

Guy 2:"Thank you, but I can't, me and a couple of other gentlemen had a Cowboy Freight Train last night and I'm afraid I won't be sitting down for a while."
by Jimbo McDoodle Snout June 06, 2011
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Dirt Box Cowboy

A gentleman who is a bit light in the Loafers, who is also an avid member of the Cheesy Wheelbarrow Pushers Club.
While playing cricket over the weekend I was asked if I'd bat for the other team. "no way!" I replied. "I ain't no Dirt Box Cowboy".
by Adlof Hilter February 28, 2023
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Wantagh Cowboy

A big burly bad boy who is equally comfortable in a saloon or camping in the 'Daks.
He knows that everyone wants to be an outlaw until there is outlaw shit to do. Armed with that information he still attends country music concerts on a regular basis at Mulcahy's and Jones Beach. He meanders along the Wantagh Parkway and Sunrise Highway aboard his trusty steed Rav4 or square body pickup. Dreaming of a class B.
He will whisper or shout while telling you a story in excruciating detail.
If you run across him tread lightly,
kindly purchase him a cadillac margarita, tip your hat and mosey on along.
The saloon doors flew open and coming in hot a figure entered. We all gasped, it was the "Wantagh Cowboy"!
He sauntered up to the bar, his bride at his side with empty six shooter hands and shouted, "Yee Haw" while ordering a Cadillac Margarita. "Don't forget the triple sec he exclaimed."
by Days1 June 24, 2024
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cowboy george

cowboy George is a guy that has a small penis. he is a not nice guy. he thinks he's the the shit. he's not the smartest.
by big farmer man December 14, 2023
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Cowboy Unit

Typically used to describe a dirty ol' redneck that aspires to be as monumentally stout as an Absolute Unit. Wears Ariat boots with faded blue jeans. Wears hats as often as possible. Probably to cover his bald spot.
Damn y'all look at Bradley walking down the hall like a Cowboy Unit. That guy is a poser -- he's no Absolute Unit!
by absoluteunit9000 October 15, 2018
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Grindstone Cowboys

In every Little League, two dads always do the work of 80 volunteers.
Sheila said, "Travis & Chris work the field for every game, even the ones their own kids don't play in!" Bob replied, "They are the Grindstone Cowboys."
by Kobayish June 25, 2024
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Reverse cowboy

A sexual phenomenon performed by 2 guys w big cocks. One male lies on the floor on his back while the other stud mounts him deep inside while facing away from him an rises his cock like a cowboy
Buddy and Joey love to ride each other’s pony’s in reverse cowboy .

Buddy rides all the homies DP and reverse cowboy
by Bullsryche January 14, 2020
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