"man I want to work for the Railroad."
by Canadianbasterd November 4, 2021
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The sexual act of going down on a girl and vaping into her vagina
My boyfriend cannot stop vaping! Last night he vaped in my pussy and called it and Underground Railroad. It kinda tickled though.
by Chu Chu Twain December 17, 2015
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The act of two males having intercourse with a single female a.k.a. "running a train" while under the bedsheets. An underground railroad is exclusively when this act is done by African Americans.
"Yo, I heard you and your bro ran an Underground Railroad on Shanockquolisha last night!!"

"Hell yeah! That sh*t was insane!!"
by TheOneAndOnlyHalfnHalf October 3, 2011
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To "ride" your girl/boyfriend like a freight hopper would
Yeah I "Joy Rided The Railroad Manafest" with Sarah last night.
by AR15 2005 April 21, 2021
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When someone is pooping and you pee between their legs
She was peeing and I had to go so I went with the undergroin railroad
by jjtwatt January 22, 2015
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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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