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

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!!"
"Hell yeah! That sh*t was insane!!"
by TheOneAndOnlyHalfnHalf October 2, 2011

What Russians say when a white person tweaking. Used to be used when white slaves working on the railroads stopped working in Russia.
by Swiftread December 24, 2022

by I KAN SPEEL August 26, 2023

Double penetration, with one guy wearing a conductors hat, and all parties involved make choo-choo noises.
by Jeffsodef April 10, 2016

by AR15 2005 April 20, 2021
