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1.
A mountain pass near the juncture of Tennessee, Kentucky, and Virginia, popularized by the folk song of the same name. The Cumberland Gap is where neighbors go to drink a little whiskey and take a little nap. You are always fifteen miles from the Cumberland Gap, no matter where you are.
My liver is extremely unhappy with me because of all that moonshine i drank at the Cumberland Gap last week.
by rogueclown January 05, 2010
15 5
 
2.
This act is done during a Chicago Wind Tunnel. It is when you shit inbetween her tits and bust your load down to her vagina making a appalachian trail.
Sorry Jenny, you liked hiking so i thought you'd like a {Cumberland Gap}.
by ChiChi McPee December 20, 2009
5 15