Trail of Tears

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!

by John Torrisi February 20, 2009

trail of tears

Farting while walking ahead of a person or group that has to follow your path.

When I was hiking with Bob, he had so much gas that he was laying down a "trail of tears".

by Fart Brewer March 7, 2008

fuck me to tears

A declaration of a desire to have painful sex.
What sensitive people request when they wish to fall asleep crying into their pillow.
An utterance of dismay.
A cry for help.
A vulgar version of have sex with me till I cry.

I showed Sally my dick, she exclaimed fuck me to tears!

by jsd9632 February 4, 2012

Trail of Tears

The opposite of a happy trail. The hair leading down the back towards the ass crack of a male/female.

"Check out that trail of tears on that Indian girl."

by John Runde June 11, 2008

trail of tears

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."

by a Tastless Turtle May 15, 2008

trail of tears

the long trip back home when you didn't get any ass

"she kicked me out and had to make that long ass trail of tears back home.....FUCK"

by metamorphosis May 15, 2004

Pink sparkly tears

Tears of frustration when confronted with one's own privilege or racist/sexist behaviors or opinions, often accompanied by claims that white/straight/heterosexual/rich people have it hard too (see; it's tough at the top).

When Sadie was told that blackface wasn't an appropriate halloween costume, she shed pink sparkly tears while exclaiming: "But I didn't MEAN to be racist!"

by Truthsparkles September 19, 2011