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When a group of men stand in a line and have anal sex with the person in front of them so on and so forth, while walking and imitating train whistle noises with their mouths. Usually wearing cowboy attire.
1) "We had the craziest cowboy freight train at our lemon party last night."

2) "Hey look! Those guys are having sex let's go start a cowboy freight train."

3) Call up all your friends, there's going to be a huge cowboy freight train in front of the city hall. Bring your cowboy hats and boots.
by Jimbo McDoodle Snout May 15, 2011
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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.

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 05, 2011
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