[Non-Fiction] Punishment Wedgie

[lilgurl]

I’ve had a few questions about the second response I made here http://www.getdare.com/bbs/showthrea...=151568&page=2 so I’ve been asked to tell the full story about that punishment. It was a while ago, so I’m filling in some of the detail, but I was asked to do it in a story form, so here it is:

It was a few years ago that a friend of mine started a game of truth or dare between the two of us. I had only played the really, truly innocent version before (truths were usually about who you had a crush on and if you’d ever kissed a boy; dares were silly things and still no one had the guts to chose them). I’d certainly never played with any guys. I think I was eighteen when it began.

My friend (I’ll call him TJ) didn’t have many other friends. We weren’t sad and lonely about it, but we did get bored. Then he mentioned that some of his friends (I didn’t know them) liked to play truth or dare. I thought it sounded silly and childish because I was used to the safe, watered-down version of the game, but then he told me about some of the stuff they did. Most of it just sounded awkward or uncomfortable, some of it sounded painful. He talked me into giving it a try, and since my truths were all lame, we just dared each other back and forth while he eased me into things.

He really liked wedgies, spanking, ice, nudity, and humiliation. I didn’t like any of those things. Still, we were bored and needed something to do, so while I was uncomfortable, he respected my limits and I tried his dares. I did most of his dares in private and reported to him. We rarely did dares together because neither of us lived alone, so we didn’t have much privacy. Eventually, TJ gave me a choice between a hanging wedgie and being his dare slave. I chose to be his dare slave because hanging wedgies are freaking painful, and I was way to scared to do it.

After that, he challenged me a lot more. I had to do a lot of things I didn’t enjoy at the time, but he taught me things I did enjoy, too (I had never masturbated until then, believe it or not). And I was willing to do the things I didn’t like because that’s what he wanted. He was sexually attracted to me but didn’t want to be romantically involved, and I just wanted to be friends, so we had an odd relationship. I never did anything sexual or nude with him, but he got off on the control he had over me and the reports I sent him. We were both okay with that.

He punished me for things like not completing dares, not reporting to him on time, not shaving my legs as often as he asked, having any grammar or spelling errors in my reports, and being indecisive when he asked where we should eat. He didn’t always punish me immediately, so there came a point when I owed him multiple punishments. That’s where this particular story begins.

He gave me instructions before he picked me up that I was to wear snug panties secured in a bra connection. To hide my wedgie, I was allowed short athletic shorts and a t-shirt. Public was one of my limits, but since this was a punishment and I hated humiliation, this would all take place in public yet stay hidden from anyone but TJ.

The wedgie was uncomfortable from the start: not too painful, but definitely impossible to ignore. And I was already incredibly embarrassed. I didn’t even know why I put up with these things, but I did. The shorts let in a lot of air and I was worried about my shirt hiding the way my bra and panties were in the back. I felt very vulnerable and nervous, but I knew TJ wouldn’t take things too far and I had agreed to his terms as a slave, so I deserved a punishment.

I rode with TJ to a Walmart outside of our town. He decided it would be best for us to go unnoticed if we weren’t likely to see people we knew. i parked and got in his car. He explained to me what would happen.

“We’re going to go in together, and I’m going to give you money to buy some things that I pick out. Some of it’s for me and some is for you. You’ll go through the check out alone.”

“Okay,” I stated reluctantly.

He looked at me and said, “Spread your legs.”

I was confused but did as I was told. When he reached toward my crotch, I closed my legs because he wasn’t allowed to do anything sexual to me.

“I’m not gonna feel you up,” TJ explained. “Just trust me.”

I slowly and nervously opened my legs again. He reached into my shorts and grabbed the front of my panties, tugging them up slowly as I felt the fabric slide between my pussy lips. For that moment, it actually felt nice. My face went red from embarrassment that this wedgie had turned me on a little.

Then he tugged them a bit tighter and I squirmed from the discomfort.

He smiled. “Is it between your lips?”

I nodded.

“Did you like when I did it gently?”

My face turned brighter red as I nodded again.

TJ laughed, “I knew I’d get you to like wedgies. This isn’t for you to have fun though; it’s a punishment, so I’m going to keep tugging on them when we are in the car to make sure it doesn’t start to feel too good.”

“Yes, sir.” I called him sir when we were in master/slave mode. I knew he really liked hearing it out loud.

“And I’ll keep checking on you to see how you’re doing. Be honest with me.”

“Yes, sir.”

We went into the store and he walked me around for a while, not revealing what he intended to make me buy. He occasionally looked at me and smiled. Anyone who saw us probably thought we were just a teenage couple; he was smiling at me because he thought I was cute, and I was blushing because I thought he was too. In reality, he was smug about how nervous and uncomfortable I was, and I was humiliated to be in that state even thought TJ was the only one who knew what was happening.

He would occasionally lower his voice to ask me questions.

“Are you enjoying yourself?”

“No, sir.”

“How does it feel?”

“It’s so uncomfortable, sir.”

“Are you comfy?”

“No, sir.”

“Are you embarrassed knowing that your ass is being flossed in front of all these people?”

“Yes, sir.”

“Are you wet anyway?”

“Yes, sir.”

“And does that make it all the more humiliating?”

“Yes, sir.”

“Tell me why I’m making you do this.”

“Because I’ve been a pathetic slave. I broke your rules, and I deserve to be punished like the slut I am.”

After a while, he found the athletic cups and picked one out. I carried it in the basket. Then he took me to family planning and told me which pack of condoms to get from the bottom shelf, forcing me to bend over and stick my butt out to get it. It pulled at my wedgie, and I felt ridiculous bending that way. Finally, he took me to the women’s underwear and had me get a pack of the biggest granny panties we could find. They were all white and large enough to fit three of me inside. I knew they would be for future humiliating wedgies.

With all these things in my basket and more embarrassment than I’d ever felt, TJ sent me to the checkout to pay for everything. I wound up between two other customers in line who had a lot more items than I did, so the cashier seemed to busy to notice. Still, that didn’t calm my nerves. He still might notice or the other customers could. There was no way to place those things discreetly on the belt.

No one seemed to pay me any attention, though, and I got away from the register, relieved to have my items hidden in a bag. I found TJ waiting for me, and we went back to the car.

Once we were both in his car, he wasted no time and commanded, “Spread ‘em.”

This time I didn’t hesitate to spread my legs, even though I knew what was coming. It was better to take that than to add more punishment. As expected, he grabbed my panties and tugged them tight, causing pain in my slit.

“Are you still wet?”

“Yes sir.”

“Why are you wet?”

“I’m wet because despite, the pain and humiliation, you’ve got my panties rubbing my clit, and that makes me wet.”

“Ready for a ride?”

“Yes, sir.”

He started driving and took us to some country roads. They weren’t paved well, some of them were gravelly, and it jostled the car. You don’t realize how much that can affect your bum until you’ve got something else messing with it at the same time. The uneven ride bounced me around a bit and made the wedgie feel worse. Then TJ took us back to some better roads and stopped at a McDonald’s.

We went inside and each got a sandwich and some fries. He told me to order a large drink, so I did, and he did the same. He made me drink all of mine while we were there, but warned me not to use the restroom. I did as I was told. As we ate, he asked a few more of his probing questions. By the time we finished, I already felt the affects of the large drink. Or maybe I was just nervous. I was afraid to ask to use the restroom.

TJ decided it was time to get back to the car, and I looked to the restrooms. He saw me and asked if I needed to go.

“May I please, sir?”

“Not yet.”

We got in his car again and, after tugging on the front of my panties, he drove me back over the bumpy roads, jiggling me and my bladder. I did not hide my discomfort well. He had actually placed a towel on my seat, so I knew he was willing to let me piss myself, but I couldn’t take that humiliation. After what seemed like ages to me, we arrived at a park. It wasn’t a popular time to be at the park, and it wasn’t a popular park, so there were only a few other people there. TJ let me use the restroom, but when I came back out, he checked my wedgie himself by tugging the front ant back. It was just as uncomfortable as ever, and I nearly panicked in the moment he did it, for fear of someone else seeing us.

“How wet are your panties right now?”

“Very wet, sir.”

“Good. Are you going to be sore from this wedgie?”

“Yes, sir.”

“Excellent.”

We walked around the park for a while, and when there weren’t other people around, he would occasionally reach under my clothes to tug on my panties again.

“Do you think you might enjoy some of the wedgies I make you do after this?”

“I think I might, sir. At least, the physical stimulation might feel good.”

“I’ll have you turned into a wedgie slut in no time.”

“Sir, it’s starting to get cold out here. Can we be done soon?”

He turned to me and I knew I had messed up. I wasn’t allowed to ask for favors when I was being punished. TJ checked that no one was around and grabbed my arm.

“You don’t get to decide how your punishment goes.”

“I’m sorry, sir; you’re right. I was wrong to make any requests. I deserve this punishment.”

“Yes, you do.”

He lead me away from the path we were on. I dreaded whatever was going to happen. TJ found a place where the ground dipped down low, and the surrounding rocks hid us from the view of any unlikely passersby. There was a fallen tree that came about to my waist height. He bent me forward over this.

“Tell me why I’m doing this to you.”

Nervously, I answered, “I’m a bad slave, sir. I disobeyed your rules. I disrespected my master. I deserve to be punished like the slut I am.”

“That’s right.”
“Will you continue to let me turn you into my kinky little wedgie slut?”

“Yes, sir.”

“Let me hear you say it. Convince me you want it.”

My face flushed again. “Please, sir, turn me into your kinky little wedgie slut. I will do your dares properly and report to you on time. My ass is yours to floss, and I am yours to command.”

“Will you do what I tell you, even if you’re not a fan of it?”

“Yes, sir.”

“Convince me.”

I took a breath and braced myself for what I needed to say to please him. “For you, sir, I’ll put ice cubes in my pussy and my ass. I’ll do wedgies for you every day. I’ll flick my nipples and spank myself. I’ll stay home naked when you say to. I’ll fuck my holes how you tell me to and I’ll use the toilet when you allow. I’ll do all this for you, sir.”

“That’s what I wanted to hear. Still, you deserve extra punishment for trying to get out of it early.”

He began spanking me, and it was not gentle. He slapped my ass in a steady rhythm at first, then sporadically. He alternated cheeks and hands. He made my ass burn, and although I couldn’t see it, I knew it had to be bright red. I kept quiet the whole time. Careful not to draw attention to us in case anyone was nearby, I only let out a few gasps and quiet whines.

After a while, TJ stopped spanking me, but I stayed where I was since I hadn’t been told to move. He walked a bit away, and I heard him unzip his pants. He jerked himself off then returned to me with a playful slap.

“That was too hot for me to wait until later to cum.”

“I’m glad that you enjoyed it, sir. Thank you for punishing me.”

While I had always know that TJ got off on reading my reports and most likely masturbated to fantasies about me, I felt incredibly awkward knowing that he had just gotten so turned on, that he had done it only a few feet behind me. I was also flattered that he found me so attractive. Then I was humiliated about the position I was in that had made him so hot in the first place.

He rubbed my sore bottom. I remained still, waiting for instructions.

“Have you learned your lesson?”

“Yes, sir.”

“Will you be a better slave in the future?”

“Yes, sir.”

“Tell me again what you’ll do for me.”

“I’ll wedgie myself. I’ll spank myself. I’ll hurt my nipples. I’ll be nude at home. I’ll fuck myself. I’ll put ice up my ass and in my pussy. I’ll humiliate myself for you, sir.” I felt that the embarrassment would never end. I tried not to think about the promises I had just made and how much humiliation was in store for me.

“Damn, that’s so hot to hear.”

Again, I was flattered, but horribly embarrassed. TJ let me get off of the log and took me back to the car. We left the park just as it was getting dark. He took us back over the country roads, which were even worse on my freshly-spanked ass.

We arrived at my place and he parked in the driveway. I knew to spread my legs before he told me. He gave my panties one last good tug before instructing me to chug his large pop, which he had refilled before leaving McDonald’s.

I did as I was told, then he let me go inside, warning me not to use the toilet until he texted me. I waited as patiently as I could, inside. I tried to distract myself from my bulging bladder until I finally got his text. He had made it home and permitted me to piss, but I had to remove my shorts, stand in the shower, and piss my wedgied panties.

I knew better than to argue or disobey. I let the stream of urine go through my wedgie and run down my legs onto the bathtub. I texted TJ back that I had done as he asked, described the humiliating feeling as well and the relief, and thanked him for allowing me to piss. He told me to remove the wedgie and clean up; my punishment was over.

Relief flooded over me, and I was glad to be done with the day. I cleaned up happily, although I still felt sore from the wedgie and the spanking. When I sat, I could still feel just a bit of the sting from the spanking, and the humiliation from the day stayed with me. I learned my lesson and did my best not to make any mistakes after that.

[SLPrince]

Absolutely AMAZING story, thank you very much for sharing.

[WedgieWolfy2]

I love this story I have read it so many times. Kinda wish someone would do this to me