Painful Wedgie Dare XD

by Dez Kimura
(Evansville, Indiana)

Hi, I'm Dez and I'm 14. I got this dare from my wedgie buddy and so I want to share it. She dared me to wedgie myself from a tree and to make it worse than ever.


The dare is also to put toothpaste in my underwear while doing the wedgie, so I went into the woods behind my house and picked a tree with branches I could climb. One of the branches was just taller than my head so I took my toothpaste from my pocket and squirted half the tube into the back of my undies, then I climbed up and sat on the branch.

Already the toothpaste was smearing everywhere, I Hooked my bungee cord around the branch and put the hooks in the leg-holes. When I tried to lower myself down easy, I lost my grip and fell giving myself the most painful wedgie I've ever had!!!

My underwear didn't even rip a little because they're the thick kind. I screamed and my butt hurt SO freaking bad but I couldn't climb back up. I tried to bounce and rip them but it just hurt my butt even more. I tried hanging on to the tree and it helped a little but I couldn't keep my grip and fell back down.

I wanted to scream for help but I decided I'd rather torture my butt crack than let my mom find me like this. It took me a long time but I finally flipped upside down. Only I slid down and now the bungee cord was hanging me upside down by my ankles and the bottom half of my was naked.

Eventually, I kicked out of my shoes and landed on my head wich hurt. Then I got my pants and underwear out of the tree and went back inside with seriously hurting rug burn and toothpaste smeared in my butt. I need to think up a really good dare to get her back with.

Help me with yours ideas.

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Nov 17, 2016
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Painful NEW
by: Misty

Did it hurt to have toothpaste in your undies? I'd think that it would be super painful, like if it were a mint. The burning sensation kind of makes me wonder.

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