When The Cherokee Indians of 1838 and 1839 were forced to leave their home of present-day Oklahoma, many dying in the process.
by Jon December 29, 2005
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A happy trail leading to a disappointingly small penis.
“I thought I was in for a good time, but all Chad had to offer was another Trail of Tears.”
by 3BigBootyBitches December 25, 2017
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lower back hair that leads directly to the asshole; the opposite of happy trail
I helped my friend Rafe shave his shoulder pads, but I'm not going anywhere near his Trail of Tears!
by ajkh1 June 25, 2011
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The small strip of hair leading down a girls back to her ass crack. Not a desirable trait in females. Typically found on Italian and Mediterranean women.
Oh shit man, it was all over when I saw her Trail of Tears. She has more hair on her crack than me.
by daveOMG!!1! November 11, 2005
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The act of unknowingly walking behind someone who is cropdusting such nasty fumes that your eyes begin to water.
- Were you crying?
- Naw, I was just walking the trail of tears behind Big Joey.
by theoxfordcomma July 29, 2013
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When you go on a strict diet of only hot sauce and chilies for three days and then blow your load directly into a girls eyes. It burns so bad she will leave a trail of tears.
So I gave her a trail of tears last night.....now she is legally blind
by Jamie Malinquetoast December 14, 2009
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