The 20 Wedgies Challenge
6 -
Bra-Connection (females and sissies)
Pull the back of your underwear as high as you can, until you see the leg holes. Then, you'll want to unhook the back of your bra and re-hook it through the leg holes of the underwear.
(Stay like that for at least 10 minutes)
---------------------------------------------------------------------------------------------------------
Permanent Wedgie (males)
Pull the front and back of your underwear as high as you can, until you see the leg holes. Then loop a (preferably strong and comfortable) lace, rope, string, belt, etc. through the leg holes at the front, bring it over the shoulders, and loop it through the leg holes at the back and tie it tightly, but in a way that won't hurt your shoulders excessively.
(Stay like that for at least 10 minutes)