Photo Story #29 (Patreon)

For this week's photo story (picture taken from @wedgieguy19 on X), I'm going to answer a question that I've had a few times . . .

Have you ever had a wedgie?

The answer is yes and here's what happened.

So, I was nineteen and at a house party with some friends, and with a lot of people I didn't know. There was a lot of drinking, and a lot of games.

Unsurprisingly, we ended up playing Truth or Dare, which was a common occurrence at most house parties when everyone had had a few drinks and wanted to spice things up.

My dares were fairly mediocre, but one of the guys I didn't know was dared to get a wedgie.

As much as I'd seen wedgies on US TV shows, it wasn't something I'd ever seen in person.

The guy in question laughed off the dare and stood up before the guy who'd come up with the dare came up behind him and lifted the back of his t-shirt.

There was something incredibly intimate about not just watching this, but the way the wedgie happened.

After lifting his t-shirt, the guy took time to pull up the waistband of the boxers and get a good grip before tugging them skyward. The guy getting the wedgied yelped and begged him to stop very quickly whilst the rest of us laughed.

Once the guy released him, the one getting the wedgie made a show of unbuttoning his jeans and putting his hands down the back of them to yank his underwear free from his crack.

By this point, I was hard as a rock and quickly excused myself to go and get some air.

Whilst I had a cigarette in the backyard, the guy who'd given the wedgie came outside and lit one himself.

"What made you think of a wedgie as a dare?" I asked him.

He laughed. "They're funny! And it means you get to grab a guy's undies. What's not to like?"

I nodded, a little unsure of how to play the conversation. I really wanted to ask if he was into wedgies and if the embarrassment side of things did it for him, but I was young and barely comfortable with my sexuality, let alone capable of discussing kinks.

"Have you ever had one?" he asked after a pause.

I shook my head and kept my attention on my cigarette. "Nope. I thought they just happened in tv shows and movies."

He grinned at me. "Seriously? You've never been given a wedgie."

It was my turn to laugh, though somewhat nervously. "No . . . never."

He flicked his cigarette butt on to the floor. "Maybe we should change that?"

"You want to give me a wedgie?" I asked, part of me hoping he'd say no, whilst the other part desperately prayed he'd say yes.

"Yup, turn round for me."

I looked at the ground as I slowly turned my back to him. My dick was hard from the wedgie I'd just watched, not to mention the conversation.

I felt his hands on my waist, first moving the hem of my t-shirt up and then pulling my jeans away from my body so he could find the waistband of my boxer briefs.

I remember feeling his breath on my neck as he said, "Mmm nice CK's."

That didn't help with my throbbing dick.

Then he gave me the wedgie, gripped the waistband of my CK boxer briefs and yanked it as hard as he could. It initially hurt before the material bunched between my cheeks and then the sensation felt weirdly hot! He kept tugging for ages, before I started begging for him to stop.

I forced myself to laugh as I turned around to face him, my hands immediately going to my butt so I could pick the wedgie free.

"You enjoyed that."

It wasn't a question and I frowned. "Not really. It hurt."

"This says otherwise," as he said as he grabbed my hard dick through my jeans. "Catch ya later."

And that was the last time I ever saw him. I asked a few people who he was and it turned out he was a friend of a friend's brother. I often wondered what would have happened if I'd been more confident and had asked him to hook up or something.

But, there it is - my first wedgie story!

Have you guys ever had a wedgie? Feel free to share your story in the comments or the chat.