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n. a life that's seemingly hopeless, a neverending epic fail. Those who lead a Trail of Fail are often emo teenagers or nerdy 40-year-olds who live with their mothers.
My life is a Trail of Fail. I woke up, stubbed my toe, burned my breakfast, found out that my bike was stolen, was dumped by my girlfriend and it's not even noon yet.
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me:do you remember when I first came on the oregon trail?
ex: yeah, we came together
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the trail of pubic hair from the mid stomach to the penis and/or vagina in which crabs can gain access to the belly button.
when i went down on jordans mom, i followed her bushy treasure trail and i felt that the chest may as well have been empty.
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At the time you are hooking up with someone you have an extreme sensation to drop a duece you then do it right there from their belly button down to penis or vagina. Which then it is no longer a happy trail it is a grumpy trail. (this may work best when your partner is handcuffed so then they can not stop or prevent the grumpy trail)
"Yeah i guess Tyler and Mary Jo doing their casual daily routine (afternoon delight) and tyler gave Mary Jo a grumpy trail. And to top it off Mary jo is Tylers mom (RUMP)"
"It was a warm summer day at Beaver Lake, Brookes (45) and Emma (14) just got done jet skiing on the shithole they call their lake. Emma laid Brookes down on the sand then giving him a warm sensational grumpy trail. So sational Brookes moaned, "I LOVE YOU PATTY!!"
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The action of a male sticking his penis into a woman's vagina, then to her ass, then back to her vagina, and leaving a poo trail on the way.
I was nailing this chick last night, got bored and stuck it in her ass then trail mixed back into her vag...giggity.
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When you itch or in anyway cause your pubis to fall off.
It was obvious that Jack was whacking off in my bedroom because he was leaving a trail.
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A woman who hangs out with Jeep Guys, likes to ride in jeeps or is attracted to big 4 wheel drive trucks. usually clothed like a slut, likes to get nailed in the woods, and hangs all over a different guy every weekend or passed around among friends.
did you see that girl with travis?
Yea, she's a real Trail Tramp!
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