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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!
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When an elite member of a gang gets killed
Damn, the Kreed got some black tears last night.
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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".
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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."
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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."
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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"
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a single tear streaming down your face
"WAHAHAHhhaaahhhh!" *onesie tear streams down face*
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