My irl wedgie stories

Wedgie dare #1

This wedgie dare was from a wattpad story called "wedgie dares" by Vanilla_essence. And before you say anything, I asked for her permission to post my experiences with them. So I don't want anyone telling me I'm a thief or anything.

I have bookmarked the "wedgie dares" story for almost 5 months now, and ever since then I've given myself a rule where I like to at least do one a week, and if I don't make it in time, I punish myself (that's a story for another day). And today I felt like doing a random one, so I picked a random number generator and the one it landed on was number 16. Where I had to be in a hanging wedgie and grab the front of my underwear with my teeth. And if I couldn't do it, I had to stay in the hanging for 5 minutes, then front chair for 10.

Like I've said before I'm a pretty big guy, so I couldn't grab it with my teeth. But that didn't mean I wasn't going to try. I spent the whole 5 minutes yanking at the front of my underwear. Each yank causing a popping sound to come out. I could feel it squeezing both sides so tightly. But when I finally made it reach my mouth, the timer ran out.

I decided to stay for an extra 5 minutes, making sure I did the punishment right. To make it worst I bounced a couple of times to make sure it was a punishment. Then it was time for the chair wedgie.

The thing is my undies were already stretched out, so I had to come up with a solution to make it feel grea- I mean, to make it an actual punishment. So I grabbed an old yogurt cup that was at the back of the fridge, and once I opened it I could tell it was old. It didn't smell that bad, but it was really runny. I slowly poured it in the front of my underwear, making sure it was smeared in every nook and cranny. I even added some to the back, make it really messy. Then I hooked the front lace to the chair. And I immediately jump down!!

It felt amazing!! The sound it made once I landed added to the overall pleasure. Then the sudden pain that came with it made me moan. I know it's weird, a guy moaning, but I can't help it. Whenever I find a wedgie that makes me feel good in all the right places, it just slips out.

And as a matter of fact, during the last 5 minutes of that chair wedgie is when I started writing this story. So trust me when I say that the feeling still hasn't gone away.