When a guy brings home a broad, he proceeds to pound her like a jackhammer in the ass, get his nut (she cant have hers), then, the most important part, steal the chicks phone, kick her out of the house and make her walk back to her house, which distance must be longer than 4 miles. Hence, the Trail of Tears. You can make her wear a headdress for effect if you want
Man, Wingo, i thought i didnt like that girl DR, so why did you take her home last nite?
oh dont worry, i made her walk the trail of tears.
That a boy wingo! Headdress too?
oh yeah, no other way!
oh dont worry, i made her walk the trail of tears.
That a boy wingo! Headdress too?
oh yeah, no other way!
by John Torrisi October 16, 2008
The opposite of a happy trail. The hair leading down the back towards the ass crack of a male/female.
by John Runde June 12, 2008
The little droplets of cum that drip out of a woman's vagina onto the floor as she makes the journey to the bathroom to clean herself off after intercourse.
by Partsguru13 June 3, 2017
by Kodykhaos February 2, 2020
When you put two fingers in a girls vagina and two fingers in her ass. You then proceed to wipe your fingers just below her eyes so it looks like she has Native American war paint.
Sean was trying to fuck this one chick last night, unfortunately his penis was much too small for her so he gave her the trail of tears instead.
by Dj urffff August 25, 2010
Contrary to popular belief, the Trail of Tears isn't the strip of hair from a girl's back to her asscrack. It is actually the name given to a particularly hairy man's happy trail, or trail of hair starting as far north as the chin and ending in the pubic region. Some men's Trail of Tears are so hairy they actually do not have a distinct path and may continue onto the rest of the man's belly or chest.
When Zack Martin took off his shirt for the swim meet, we all got a really good look at his Trail of Tears...
by me May 4, 2006
by Stevie Yates September 13, 2009