8
Two or more black males having sex with a black female, whilst in a basement.
Black_Guy1: Yo, me & Chanel had an Underground RailRoad last night!

Black_Guy2: Tight, dawg!
by NitroFight53 August 21, 2010
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9
When a train captain drives a train into a woman's vagina.
Man 1: Did you fuck her?

Man 2: Yea, but she was loose enough to give an underground railroad.
by Skeetman69 December 06, 2008
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10
the act of a girl starting with her tongue in the deep south (ball sack) and running up the length of the underside of the penis to the north (penis head). pioneered by harriet tubman, she is know as the best known giver of underground railroads, performing on Abraham Lincoln, getting him to free the slaves.
i hate getting underground railroads, they tickle.
by chrisdylan February 17, 2011
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11
A clever escape route, or the act of leaving a crowded place or a sticky situation, without anyone noticing until long after your gone.
"Hey, anyone seen Tom?"
"yea..like a half hour ago by the keg"

"Damn, He must have hit the underground railroad"
by doughboys9 May 08, 2007
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12
the act of getting a girl drunk and bringing her back to your hotel room, where 4-6 of your friends are waiting in the bathroom. Proceed to slam her from behind, (its key to make sure she cant see your face) and when you are about finished, you call in the next guy. This secret train continues until all 4-6 are finished. When the caboose is done, u go back to the girl, fake an orgasm, and your done with her. Make sure she leaves the hotel room quick, before she wants to use the bathroom.
After the game me and half the team are planning on getting an underground railroad going on some skank from the club, you want in?
by Big Matty Johnson October 24, 2007
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13
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 March 28, 2016
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14
When 2 black guys are running train on a girl.
1.) "Yo Jared, did you hear that Stephanie was riding the underground railroad last night?"

2.) Luis and Tivo gave Monica a ride on the underground railroad last night.
by theMASShole March 27, 2012
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