Embarrassment

The Latex Wedgie

DownUp (No Ratings Yet)
Loading...

I was 16, and so was my friend May. We’ve been friends since Kindergarten, and we had this rivalry going on. It was on-again, off-again, and it never seemed like it was gonna end. Well, the last prank I did to her was pretty, no, VERY exteme, so she wanted to get me back, just as extremely. No, 100x more extremely…

 

After her swim class ended, we decided to swim in the pool. The majority of the people left the pool, so it was basically just her and me in the pool, but that didn’t mean we were the only one there. We were swimming for a while, until I realized I felt a bit bare down there. The water seemed to be getting colder, until I looked down only to see my swim shorts were off!! She must have pulled them off while I wasn’t paying attention! “Hey! Give those back!” I yelled at her. May just giggled. “No way!” She says “After that last prank, you won’t be getting these anytime soon!” She jumped out of the pool and pulled out the plug that was keeping all of the water in, so the water was leaving the pool and my penis was going to be revealed! “Ok! Ok! I’m sorry! Just give me my shorts back before everyone sees me!” She smirks “Well…” She says. She throws a 10 sizes too small purple, frilly thong that says “DADDY’S GIRL” in big black letters “No way am I going to wear this!” I say embarrassed. But the pool was getting lower and lower “Fine! I guess everyone will see your dick!” I get nervous, but seeing that there was no other solution, I quickly slipped it on. At least I tried to. Like I said, it was 10 sizes  too small so it barely fit. By dick was crushed and by booty was red, as the thong pressed against it intensely. I almost cried from the pain. Some people snickered when they saw me. That’s when May grabbed my thong and wedgied me so hard it almost ripped. “You like that, daddy’s girl?” She giggled, as I squealed in pain. Then she pulled down my thong and slapped my butt, as if it wasn’t red enough! She poured burning cream on my dick and watched as I screamed in pain. She handcuffed my hands  and kicked me so hard in the penis, I swear it shriveled a bit! She gave me one last wedgie and then carried me outside. “Wh-what are you doing?” I asked nervously. She tied my feet together and put a sign next to me that said “Embarrass the loser! Only 25 cents!” I almost peed my pants- er.. Thong. She pulled down my thong to my knees and I couldn’t even pull it up because my hands we’re cuffed! I got a massive erection too! She grabbed a video camera and recorded me. I was about to scream, but she put tape on my mouth. People were walking by and giving May 25 cents to humiliate me. Some people spanked me on the butt AND the dick. Some people kicked my dick and threw things at it. Some one pulled up my thong and gave me an atomic wedgie so hard, my thong ripped! I was so humiliated, I turned tomato red! Some girls rubbed my dick to tease me and my erection got harder and harder! I wanted to cry so much. That’s when May let me free, but not without giving me another thong. This one actually had kawaii Bears on it and a hole in the back, so my bum cheeks were visible! I ran home, but that’s when squirrels jumped through the hole in my thong and crowded around inside my thong! They tickled so much and I just kept jumping around like a clown! May kept laughing and she ran back over to me, and carried me up to her house. She threw me out her window, causing my thong to catch a hook outside her house, giving me the biggest wedgie ever! My butt was bleeding and turning red and by dick was riding up. Some more people came and took videos and threw eggs at me. The thong have out eventually and I was naked again. I escaped back to my house safely, but I was so embarrassed!

 

The next day at school, everyone was snickering, May must have told them what happened. But she didn’t have to, because on the jumbo tron in the hallway, it showed my embarrassing torture! My thong, my wedgie, my humiliation! It was featured on the school page and my friends never let me hear the end of it!

0

Wedgie Humiliation: The Performance

DownUp (No Ratings Yet)
Loading...

I was one for being made fun of, mainly because of my… Ahem.. Pubescent problems… Well I was also one for teasing, and there was one girl I always teased named Sarah. Sarah and I were sort of friends and enemies at the same time. We’d always pick on each other, but I always won, but today, it looked like Sarah wanted the trophy for once, and she went hardcore…

Today I had a big performance, and Sarah was coming to watch. I went to my dressing room to change, and things were going pretty well until Sarah came into the room. She didn’t even knock! And I was in my boxer shorts! I was pretty humiliated. “Get out!” I yelled at her “What are you doing here?!” She laughed for a moment, and when I least expected it, she pulled down my boxers and she saw my penis! And remember what I said about my pubescent problems? Yeah… My dick was barely 3 inches… She began to laugh and laugh, while I blushed and tried to cover it up. “G-give them back!” I yell nervously, hoping no one hears. That’s when she tears them up into shreds “Whoops!” She innocently says. I blush like crazy! “You’re on in 5 minutes!” My director says from outside “OH NO!” I yell “I can’t go out there naked!!” Sarah smirked “Well I have something you can wear…” She deviously says “Oh thank god! Give it to me!” I say relieved. That’s when she pulls out a 6 sizes too small, pink, frilly, thong. I was mortified. “LIKE HELL I’M GONNA WEAR THAT!” I exclaim in disbelief “Well I guess you’ll be naked in front of everyone, now won’t you?” She says, twisting the thong around her finger. I blush, and reluctantly wear it. She laughs. The thong was extremely small, so it rode up my booty and nearly crushed my dick. It was burning so badly and I felt like it was gonna pop off. “Good boy!” She says deviously. I turn completely red, and that’s when she gets out burning cream and pulls down my tiny thong. She rubs it on my penis and closes the thong. “GAH!” I say “I-IT BURNS!” She then handcuffs my hands behind me and pours an entire container of itching powder down my thong and on my crotch. I jumped like crazy and screamed, but she put tape on my mouth! That’s when she gave me the most intense wedgie ever and my buttcheeks pursed together as I got a massive erection! She pulled down my thong, grabbed a paddle, and spanked me until my booty was red like a tomato! She gave me one last wedgie and then kicked me in the crotch so hard, it shriveled! I wanted to hold on to it, but my hands were cuffed! I was in so much pain! That’s when she began to laugh again “Ok, I think that’s enough pain for today!” She said “Quick! Get on the stage!” My director called out again. I couldn’t! I was in a tiny thong with a burning, itching, and erect crotch, and handcuffed and with tape on my mouth! But Sarah pushed me out there on the stage and everyone saw me! They all began to laugh! I was so embarrassed! “NOO!” I screamed through the tape, as people snapped photos. I wiggled and ran around in circles trying to escape from the handcuffs clutches. That’s when Sarah lowered a hook on the stage and gave me the biggest wedgie ever! My penis actually began to slip out and my booty clenched in pain! Everyone was pointing at my small dick and laughed even more. That’s when the wedgie tore my thong and I was naked! I didn’t know what to do! People began to throw things and one hit my tiny crotch! My dick was still itching! I just ran off the stage, but not without Sarah spanking one more time, and this time, my dick!

0

You should NEVER bet against your step-sister

DownUp (+1 rating, 1 votes)
Loading...

When you’re seventeen years old, and you have a one year older step-sister that isn’t afraid to show herself to you in her bra and panties, you should NEVER bet with her. It’s just a really bad idea. Sadly I didn’t know this until it was way too late. On time when our parents were out of the house, she called up five of her girl-friends to hangout that night. My step-sister is hot, and so are her friends, but that didn’t stop my embarrassment that night.

My sister came up to my room while I was just reading a book. She was with her friends and she decided to place a bet with me. She said that if she won, I would have to strip naked in front of her and her friends and I would have to let them do whatever they wanted to me, not just then, but every other time they would tell me to get naked. I told her that if I won, she’d have to strip naked when I told her too, and let me record her strip-teasing to show to all of my friends. We both agreed and then she told me what we had to do: ”Arm wrestle.”

I almost wanted to burst into laughter. Really? She wanted to have a strength contest against me? I thought it was going to be the easiest time of my life, and easyfap material for the rest of my life. She said it was best out of 5, first to three wins the bet. The first two times, I beat her easily. She looked as if she was regretting her decision, but then, when it came to rounds 3, 4 and 5, that’s when she got me. After thegowas called, she instantly took my arm down in a pinch. I was absolutely caught by surprise that SHE beat me at arm wrestling. That’s when I lost the bet. My sister made me strip naked in front of her friends and show my penis to them. The girls started to feel my penis and my balls and it was embarrassing. Not because it’s a small penis: It’s 7’8 inches. It’s the fact that they were all taking picture of it and saying that they would show it to their friends and what not. Then they told me to masturbate for them, which I did, whilst they were recording all of it with their phones. At least I had very good material in front of my eyes, but I could still never have myself cum in front of them. That was until my step-sister took my place and wanked my penis as fast as she could.

I sprayed so much cum in front of the girls, it was so embarrassing. After that, the girls brought me outside wearing nothing but… a dress. I was paraded outside in a dress with nothing under. One of my sister’s friend said that it her little sister’s birthday party, and that we should go over there. Despite my objections, I was forced to go there, and when I was in front of the fourteen and fifteen year old girls, my step sister and her friendsripped the dress from off of me, leaving butt naked in front of the minor girls. I tried to cover myself, but I was told to stop and let all of the teens stroke my penis if they wanted to. They made me cum a few times before I was finally brought back home, walking naked completely naked along side my step-sister.

She made me do so many embarrassing things after, like making me act like a dog while naked in public, have me to school in my undies or in one of her thongs and other things. But here’s my tip, and I’ll say it again: NEVER BET WITH YOUR STEP-SISTER!

1

Gymnastics Embarrassment

DownUp (+2 rating, 2 votes)
Loading...

Okay so I do competitive gymnastics. One day, I went to gym after school just to do a little practicing. I was wearing dri-fit nike shorts. As you know, they have built in underwear, so I wasn’t wearing any. My teacher was spotting me on a trick, and instead of grabbing my shirt to spot me, she accidentally caught my pants. It was awful. It wasn’t just a little second long slip, they came down do my ankles. I landed on my knees, and my bare butt was there completely exposed to everyone in the gym. That was a ton of people! I turned beat red, and I pulled them up as fast as I could. I know it didn’t help though, because I sat in shock fit a few seconds, so I know everyone got a good look. My coach apologized, but she laughed at first also. I will NEVER get over that! It was soooo embarrassing :(

0

I was having a “moment”

DownUp (No Ratings Yet)
Loading...

WHEW! where do i start lol, okay I was having a “moment” with my crush and my nose started bleeding all over him and his white t shirt, I smoked weed and got so high I couldnt stop Farting around my More

0

Staring at girl punishment

DownUp (+2 rating, 4 votes)
Loading...

A year when I was 14(boy) I was home alone with my older sister(19). It was in the afternoon and my sister had her friend over to come swimming in our pool. My sisters friend name was Heather and she was More

6

Baby embarrassment

DownUp (+2 rating, 2 votes)
Loading...

After we brought our first child home, we went through all the sleep deprivation and adjustments that new parents go through.  Back then, i always slept naked, so when the baby woke up at some point in More

0

Pantsed By Big Sister

DownUp (+2 rating, 2 votes)
Loading...

It was when I was 9 years old. I know, getting pantsed by my big sister sounds embarrassing, but it was even more embarrassing then it sounds!

That day I was coming on home with my friend named Bill More

8

Dolores comes to visit me and my mom

DownUp (No Ratings Yet)
Loading...

was at my house after going home from the Cinco De Mayo party where I had met Dolores. Actually, I live with my mother. She is eighteen years older than me and is a fitness buff. She is well toned and More

2

Cream embarrassment

DownUp (+1 rating, 3 votes)
Loading...

Ok so I’m 15 And I went to the doctor because I have Been having som

Itching and rashes down there. And my mom wanted me to get itchecked out. 

So I protest but I go . I sit in the waiting room and then More

1