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Railroad Man

A guy who apparently built all the railroads in the USA, and tried doing a loop-de-loop with a steam train because the Wright Bros (who don’t make a right with two Wrights) convinced him to. He ended up failing, and they told him to shove his rail up his crack, so he wrote in the land “Go fuck yourselves”. So some guy who hated airplanes because he owned trains.
“I wanna share a tale with you about the ‘Mercian dream, when all the railroads ran on time and our nation ran on steam. Behind the tracks and railroad ties, a hero took command, of connecting every town, and he was called, ‘Railroad Man’”

-Cyanide and Happiness™, “The Ballad of Railroad Man”
by I.E.I. Industries February 25, 2023
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Railroad

"man I want to work for the Railroad."
by Canadianbasterd November 4, 2021
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Greasy Railroad

The act of ejaculating onto a girl’s braces while she smiles.
Dude 1: “I saw you go home with jessica after the bar last night!”

Dude 2: “Yeah bro she let me give her a greasy railroad on that fucked up smile!”
by MFE.51101 October 5, 2021
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California Winter Railroad

The sexual act of cooking mini corns dogs in a hot toasty oven at 400 degrees F for 20 minutes and then proceeding to insert a minimum of 6 mini corn dogs into a XL condom. After this, proceed to freeze for 24 hours in the tied off condom and then insert that California Winter Railroad into any orifice of the body you desire.
Your fetish with mini corn dogs has taken you down an interesting path on the California winter railroad.
“My partner ask me if we have California Railroads set up in the freezer to stuff in their giant phat ass.”
by Gannimal October 28, 2021
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Railroading

A railroading is when you seek up on someone in the middle of the night and scare the crap out of them.

To have this happen to you is to be railroaded.
Hey man, are you okay? You look pale.

Yea man a guy just walked up on me and railroaded me. Scared the crap out of me that railroading did.
by SwampFox56 November 19, 2022
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I built the railroad

A commonly used phrase spoken at the Santa Cruz Motel that in turn, means you want a train pulled on yourself.
This chick just showed out of nowhere and was like, " I built the railroad. " So we all gangbanged her tight lil ash.
by Adub408 February 11, 2022
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Elevated underground railroad

The part of the subway that runs above ground.
The black people were in plain sight of the racists while on the elevated underground railroad portion of the underground railroad.
by Solid Mantis November 25, 2020
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