look up any word, like darude - sandstorm:
 
8.
1)Penetrate the anal cavity.

2) To then rub the genitalia across the vaginal region and across her stomach (the Great Plains) moving forward to the Rockies (her chest) and park your wagon in her mouth, leaving a brown trail.
when your having sex and you make a trail of poop. The Oregon Trail. Have you ever ridden on the oregon trail?
by Trail Master July 19, 2008
 
9.
the cave in Blood Gulch left of Domination Hill with the overshield in it.
Frick! he's in the Oregon!
by Ryo March 29, 2004
 
10.
Oregon Trail: Normally performed in restaurants and or school. It is the act of sending your gassy discharge in a genral direction, generally north or south, (not just a sloppy spray). If done correctly you should feel as though you shated a small marble that is carried on the currents of your ass. Very exzilerating..
Yo, my warm shit breath just took the oregon trail and heated my gooch and tickled my ball hairs....most triumphant

Oh fuck, something fell out the back of the wagon on that oregon trail and left skids all up the crack of my ass, yo
by corterized balls October 25, 2004