by token1 September 25, 2009
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.
by Braveheart's thirst for blood February 12, 2007
When at a casino and you throw a chip at someone and tell them to get a blackjack book and leave the table because they have no fucking idea what they are doing....
Hey! Cowboy...here's a $25 chip...go buy a book on blackjack and come back when you know what the fuck you are doing - you have cost me $400 in 20 minutes....
Ben threw a Cowboy chip at an old lady and told her to leave the table...
Ben threw a Cowboy chip at an old lady and told her to leave the table...
by B. Hanback January 15, 2010
When two homosexual males take a shit on each others chests, then give each other a long shitty hug and smell each others shit.
by Crisp June 24, 2008
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.
by Al Tonen April 06, 2004
by Roy69 April 19, 2010
A group of fans that have low IQ, low sperm count and never stop making up excuses for perennially failing for the past 20 years. Have stupid chants of “We DeM bOyS!” Or “HoW bOuT tHeM cOwBoYs”. Will talk about the glory years that happened over 2.5 decades ago like a guy who can’t get over his ex and never shuts up about them. Their god is the crypt keeper known as Jerry Jones. They will also cheer for them as well as the Lakers and the Yankees
by Cowboys SUX November 23, 2021