This is the act of ejaculating deep inside a girls asshole without her knowing it's about to happen. As she becomes comfortable with a little fingering of the Brown eye as you fuck her, you make your move! Pull your pistol and saddle up her back door for the ride of a lifetime! It's certain to end with a bang! If she likes it, then youll know you found your philly!
The Brown Cowboy is the act of ejaculating in a girls ass without her knowing it's about to happen. Also used as a test to see if she's a keeper.

Bro! I think I'm I'm love! I pulled the Brown Cowboy last night and she liked it!
by Sean Day Lou Swahili Swag September 1, 2016
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When a man is fucking his partner doggy style, he suddenly pulls out and rams his un-lubed dick into his partner's ass. He then grabs their hair and pulls it while fucking their ass. The goal is to see if he can stay in for eight seconds.
I was getting bored while banging my girlfriend last night so I pulled a brown cowboy.
by Nacho Cespedes December 2, 2014
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It's me again, Steerforth. Those of you who think Brown Dirt Cowboy refers to something gay are too young to appreciate what Bernie Taupin was talking about. It's as I said in #2. They are names made up by children when they were playing. We did it all the time. I liked to be Flash Gordon or Rocketman!

Captain Fantastic:

A children's game played in England in the 1960s.

The Brown Dirt Cowboy:

Probaby refers to Roy Rogers
There are links to prove the meaning of Brown Dirt Cowboy, but Urban Dictionary does not allow links in the definitions.

So much for proof and accuracy.
by Steerforth November 23, 2011
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I recall this from my own childhood in England. We would always become a "character" as we were playing. One day it might be "Rocketman" - another day it might be "Captain Fantastic" and another day it might be just a brown dirt cowboy. We could make up our own names, too.

Superman, Batman, the Lone Ranger, whomever.
Rocketman Superman Batman Lone Ranger childhood pretending Brown Dirt Cowboy
by Steerforth July 23, 2010
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Female on all fours, male standing behind. As if snatching a revolver from a holster at noon, male raises finger-pointed hand rapidly and pushes extended digit into female's anus.
"What's the matter Mary?"
"Oh Jim gave me a Cowboy Brown last night"
by Boysie May 20, 2015
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someone who like to pound brown stars is a brown star cowboy
donald is a brown star cowboy case he lieks the brown star
by steven loughran November 1, 2006
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