Embarrassing stories involving nakedness, humour, sex and public humiliation
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Showing 10 stories, ranked by: Random (click to retrieve another random set) - Top rated - Least votes - Most recent - Most votes

Gag-a-rama by Barry - May 1 2010

I used to date this girl named Sara and she loved to playfully do role-playing. It might seem kinda weird but we had a lot of fun. One of the roles that she liked to play was being my Dominatrix. One of my most embarrassing moments came from one of these role-plays. Sara had taken me to the mall to buy some thong panties and took me back to her place. When we arrived at her house, her ex-boyfriend and two of his friends were there waiting for us. She asked me to strip down to my thong panties and perform fellatio on each of the guys while she watched. It took her awhile to persuade me, but she did. I slurped on the first two guys and worked them very thoroughly - they both finished in my mouth. Sara had me swallow each time. Then her ex-boyfriend started to force-feed me and even hard-core gagged me repeatedly for like 20 minutes. Sara seemed to love it. When he was done with me, I felt like a total slut but Sara said it was great. I felt sooo embarrassed about it. That was the first of about 20 times that role play was played out for Sara and I.

(Rated 5.3 out of 10) with 152 votes
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Too Relaxed by sirius - Jan 17 2014

Most embarrassing moment ever - One time I picked up this really hot guy off the street and we went back to his place. He was rimming me and I farted in his mouth LOLZ!!! I saw him often because he lived nearby but I had to avoid him at all costs after that.

(Rated 5.35 out of 10) with 197 votes
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Exposed And Embarrassed In Exchange For Money... ( Not Worth It ) by AliceCleave - Aug 17 2014

My bff and I decided to pull a little trick on the boys of our school and see how many would fall for it ( we were expecting none, to be honest ) One Friday, when I knew my parents wouldn't be home at night, my friend and I decided to post a few posters on the wall of the school, saying this message "Boys boys! With penis' of any size, pay only 15 dollars to have it wanked by Alice Cleave and/or by "my friend's name" or 35 dollars to have it sucked like you never got it sucked before! Come to "My address" tonight starting at 5:30 PM with your money to get your pleasure!" My friend and I were considered some of the best looking girls at our school, but we wondered HOW many of these guys were either desperate or perverted enough to give use their money to have use play with their penises, which she had done only a few times before, and me only once. Turns out, we were very much surprised by the outcome. When my door bell rang, there was a HUGE amount of boys waiting for us as we opened the door. I'm not sure how many there were, but there were way too many for us. But with all of them showing us their money and how it would be kind of a jerkish thing to tell them to go away and that it was fake... we decided to try it out. Some of the boys asked us if they could pay extra to get a second time with us playing with their penis's and we said sure. Throughout the whole night me and my friend were jerking and sucking different penis's of different sizes. We were making so much money off of something we thought was just a JOKE! Then one of the guys seemed to REALLY want to throw his money away, because he payed 150$ to each of us so we would strip completely naked. We decided to do it, and told the boys we were open to a few other requests depending on the price, but no penetration was allowed. For a while no one offered, so we both sucked and rubbed penis after penis completely naked. We were making so much money and I didn't feel like I ever wanted to stop. I actually started to suck on one penis and rub two others at the same time to have it go quicker. Some guys had way too much money to spend, as they would pay 50$ to spank our butts, 100$ to rub and suck on our tits and one decided to pay 200$ each to eat our pussies. It was so hard to refuse such an offer! Embarrassment in exchange for money... A lot of the guys started to record the whole thing with their phones when they weren't getting played with, which for some reason, my friend and I didn't mind. Throughout the whole night, my friend and I made a total profit of 1755 dollars! We split it in equal halves, but it was quite embarrassing when the boys showed the video to everyone they could at our school: Showcasing our naked bodies and us acting like complete sluts... I sometimes think now that it wasn't worth it.

(Rated 8.94 out of 10) with 17 votes
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Umm Football Me Crap by rosestonton - Aug 23 2012

I was playing a 3v3 football im a 24 year old girl now my team was loseing 3-2 so we all had a plan so we where all in this little shed me and my team striped naked to have a 5 min shower but when we came out are clothes where gone thay just lifed are knickers and bras now my team put £50 in to win thay did the same so if we did not play we lose £50 or get embarrassed by the other team so we did i was in goal now it was a pen and my knickers where up my ass so wedgie + just knickers and bra + embarrassed = somehow i win my team 5-4 so we got £100 i was embarrassest but won

(Rated 5.37 out of 10) with 100 votes
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True Princess Leia Bikini Story by the listener - Oct 11 2013

When I was 9 years old, I didn't have a lot of friends. Therefore, I hung out with my brother and his friends. I was kind of a tag-along. He was 10, and I was younger than everyone in their group. Anyway, if you included me, which most of them didn't, their group consisted of 5 boys. Having said that, we were all real young, and liked to play silly games. One thing we did was act like we were characters in our favorite movies and get into adventures and stuff. One day, one of the boys suggested we played "Return of the Jedi." Our plan was to use sticks as light sabers and the bad guys would be pretend, so we would just strike the light sabers at air. As far as costumes, we decided to use bed sheets, towels, stuff from the Halloween box, and tinfoil armor and stuff for costumes. You know, silly kid stuff! Like, the boy that pretended to be Luke, for example, was able to find a black cape in the Halloween box and hide his light saber in it. You know, stuff like that. So, when it came time for us all to call the characters we were pretending to be, one boy called Han Solo, another boy called Chewbacca, my brother wanted to be a "white" Lando, and the last boy called Luke Skywalker. By the time it came to me, no other male characters were left, (none of the main ones anyway). Since there were no girls in the group, they all asked me to play Princess Leia. My first thought was, no way am I playing a girl's role! But they all used the whole "you're a chicken" technique and the whole "we need someone to play leia, so we beg you to do it" technique. One of the boys was even clever enough to point out that men played women in old Shakespeare plays back in medieval times. Even as a 10 year old, he was that clever! Anyway, so eventually I said yes, but made them swear not to tell anyone. After they did, I grabbed a white sheet to make into a robe and said that would be my costume. They all said no, however! They told me Princess Leia wore white white robes in the death star in one of the other Star Wars movies. They wanted to act out scenes from Return of the Jedi. I didn't remember what Leia wore in the Jabba the Hutt scenes in that film, but they all laughed and my brother's friend, (whose house it was), snuck off into his sister's bedroom for a minute or two. Here's the embarrassing part: he came out of his sister's room with a bikini in his hand. He handed it to me and told me that would be my costume. I went back to saying "no way," but I don't know why, somehow they convinced again, but it took longer. I'm not gay, but at 9, I was naive. Anyway, I guess Leia wore a gold bikini in Return of the Jedi when she was Jabba's slave, so I can see why they picked that. I once again, made them promise not to tell anyone. So I went to the bathroom to change. They all got to put their costumes on over their clothes. I was so embarrassed, I had to take mine off to put the bikini on. When I walked out there, it was real embarrassing to see them fully-clothed, and I was standing there in a girl's skimpy bikini. I remember it was green with white polka dots. The most embarrassing part was when his mom and sister came home. At first, his sister was annoyed that I was wearing her swimsuit, but after a few moments, she said to me, "for a boy, you look in a bikini." That was the most embarrassing moment of my life.

(Rated 5.05 out of 10) with 142 votes
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His Pants Confused Me by Miranda - Aug 23 2012

Ok so it was me and my boyfriend at the time and we were hooking up and I decided to go into his pants...but I seriously could not figure it out. After like 10 minuets he showed me that there was a little hook kinda like on a bra. I didn't know that they made guys pants lie that...it was so imbaresing.

(Rated 4.66 out of 10) with 102 votes
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At My Cuzin House by Abbie456 - Sep 26 2010

I have a cuzin name james and i was there with my cuz and my 3 bro and 3 step brothers and my cuzin james was pretty evil and it was a pool party we were celebrating my other cuzin leslie and miranda bday the twins. Then it got really late everyone left leslie and miranda was going to the movie theather with there bf. So we were playing truth or dare btw i was 12 there. My brother said to me whispering if u pik truth ill tell ur secret wish he got my secret by my notebook so i got little bit nervous cuz i didnt want him to tell my secret and i pik dare they told me well remember the rules r when u pik a dare u need to do the dare that the ppl ask u then my bro and cuzin and step brothers look at each other smiling. Then they started whispering then they all agreed. Then they said Ok u need a dive in the pool naked i said no way pik another dare then they said remember the rules i did it cuz i new that they will do something embarrassing then i took of my clothes then they started laughing and say look bak and they started laughing. They said ok go jump i dive in and then they grabbed me i was cold and they tied me in the chair

(Rated 5.33 out of 10) with 154 votes
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The Basketball Game by Billy - Feb 3 2014

My girlfriend told me that she could beat me in a basketball game one day and I immediately laughed in her face and said "if you beat me I would play a whole other game with you naked!" She took it literally and I was confident that I would win so we bet that. Well the day came that we were going to play and she was much better than I thought! We played a game up to 50 and she won 50-47! So right there in the middle of the park I stripped naked and we played another game! A few people giggled as they walked by and a bunch of people looked shocked! I know for sure my naked body is saved on a bunch of strangers phones! Even after this my girlfriend wouldn't give back my clothes so I had to walk home along a main road naked! It was so embarrassing!

(Rated 4.54 out of 10) with 114 votes
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School Dork by Bookworm - Aug 7 2011

My clothes were all in the laundry so I put on thes jeans that were WAY to big and A my little pony shirt 3rd grade. I forgot my bra and am wearing granny panties and I am a c cup I also slipped on my white trainers with dorky tube sox. My parents are over protective and strict so I wear dorky outfits like this. So I went to the bus stop and the "popular girls" saw me and they hate me so tied my hands together and made me sit by them on the bus and then guided me off with them pushing me and giving me wedgies and then at lunch (no teachers) they stood me up on stage and pantsed me and then hung me on the flagpole and I started crying and they pulled me up hanging above everyone by me granny panties and peed on their heads and pooped In my pants ( I was VERY nervous) they lowered me down and stripped me naked with just my poopy but and tube sox and trainers. They they poured milk all over me and then I got my clothes back and then I was so nervous i peed and pooped again and now my parents make me wear a diaper and tight pants to make sure I an wearing one. They also banned me from make up and bras and I am the biggest looser ever.

(Rated 5.04 out of 10) with 164 votes
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Don't Bet Versus Your Sister by Frank1234 - Aug 19 2014

When I was fourteen, I made a bed against my older sister ( 16 ). The bet was that I couldn't get a 75% on my next math test. If I lost, I would have to masturbate in front of her and all of her friends whenever she asked me, but if I won, she had to do a personal strip tease for me every time I asked her as well. I attribute this loss to bullsh*t, because I got a 73% on the test. The worst part was, some of her friend's are the older sisters of some of the girls I knew from my classes, so when the time arrived for me to wank in front of them for the first time, there were about twenty girls, with a few of them that I actually knew. The girls used their phones to record the whole thing and I was so embarrassed. Still to this day she makes me wank in front of her and her friends. Never bet against your sister, EVER!

(Rated 3.63 out of 10) with 16 votes
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