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 February 20, 2009

by RichieG May 10, 2005

by Fart Brewer March 7, 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 11, 2008

When you are at your partner's house and, just before orgasm, pick her up, continue to climax as you walk towards the front door and as you finish drop her on the front step and slam/lock the door behind her.
"Todd, what do you mean 'Come over to my place'? I thought you lived with Susan?"
"I did, but I went trail of tears on her; It's my land now, Zeke."
"You truly are a man, Todd."
"I did, but I went trail of tears on her; It's my land now, Zeke."
"You truly are a man, Todd."
by a Tastless Turtle May 15, 2008

by metamorphosis May 15, 2004

by KINGLOOLOO July 27, 2009
