Embarrassing Moments!

If you're here to discover the most embarrassing stories of nakedness and humiliation, from the wild and wacky to the down right indecent, you've come to the right place.

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Showing 10 stories, ranked by: Random (click for more) - Top rated - Least votes - Most recent - Most votes

Princess Leia Bikini Story by the listener

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 cute in a bikini." That was the most embarrassing moment of my life.

(Rated 5.15 out of 10) with 742 votes
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Mixing Up Slippery Lotion And Normal Lotion by GamerPlaysGames

So i put on lotion daily but i ran out and my mom bought a new one she bought the wrong one i put the lotion usually near my butt and legs and its super slippery so i trip at school like i always do then my panties fly off and land on my crushes head ( btw were wearing school uniforms so we have to wear skirts ) someone pantses me im just trying to cover up my hairy areas cuz i hate shaving/waxing then they put my panties back on and gove me a wedgie when im in the air the string goes up into my butt crack and i think i asked them super sexily or something? Cuz they start drooling and i just say Please let me out then i winked so they would let me out they did then proceeded to strip me and i blanked out

(Rated 5.26 out of 10) with 368 votes
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I Got Pranked By My Friend by rosestonton

Im a 24 year old girl and my sis has this boy named brandon at 14 she had to go to a party and it was a age 18 party so she asked me to have him for the night so he was a bit grumpy so i gave him a wet willy to chear him up so he smilled at me and shed he needs to get something so i shed ok im just going to swim he shed ok so i went swimming and i got bord so i stripped naked to swim i went to the other side of the pool looked back and brandon was there i shed hi and he shed bye and picked up my clothes and towel and went in so i went in and with my arm on my boobs and my had on my p.u.shy i shed can i hav my clothes pls he shed ok there in the fridge i shed what told him off looked in the fridge thay where not there so i shed where are thay he shed fine got me to the door and shed there i shed where and he pushed me out the frount naked i try to get in the cat flap and got stuck for about 1h and his mum got back looking at my ass and asked what you doing i told her and brandon told her the truth so he went back and befor the mum went she shed you need to get less of a tan on your ass but other than that its not bad so my hace went so red it was embarrassing but me and the little shit are good friends i told him about this site

(Rated 4.85 out of 10) with 785 votes
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Got Turned On During A Medical Exam by CoronaMan

I was seeing a Physician\'s Assistant for an ingrown toenail on my left foot. As part of her exam, she was tying to find a pulse on my foot without success. rnrnHer next move was to try to check my pulse on my inner left thigh. I unbuttoned my pants to allow this. rnrnI happened to notice she was putting a glove on her hand. My first thought was "Okay, what\'s the glove for?"rnrnAt this point, she pulled the elastic on my underwear and got to where she wanted to be. Unfortunately, she happened to brush my penis in the process. This caused me to have an erection. She just ignored it and kept working. Needless to say, I was quite embarrassed.rnrn

(Rated 261.48 out of 10) with 128 votes
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Naked At Wine Gala by Akki

I was once asked to work as a waiter at a wine gala. This was in my college days. Once I got to the event, I realised that I had to wear a toga. The guy helping me change into it noticed that I was wearing black underpants. He asked me to remove them. I did so. The toga was then wrapped around me. I was handed a tray of drinks and headed out. The first hour went by but I noticed that the pun holding my toga together was not as firm as I thought it was. Decided to put my tray aside and head back to the dressing area but before I could, I was approached by two ladies who started admiring my toga. To my horror, one of them slipped her finger under the pin and took it out! The entire toga felt to the ground. There was silence and then laughter! Lots of it. I politely handed the tray to the lady, covered up my front and ran towards the dressing area. But by then, they all had a look:-)

(Rated 4.8 out of 10) with 727 votes
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Barry Wearing Panties by Barry

My name is Barry and I wear thong panties. A female friend of mine and I went to a club and she told one of her girlfriends to wedgie me. So this girl walks up behind me and quickly wedgies me - showing everyone behind me the silk tiger-print thong I was wearing. It was very embarrassing. Those girls now call me "tiger."

(Rated 5.29 out of 10) with 732 votes
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Caught Naked...again by Mina

If you have read my first story I was really embarresed. This one is more embarrassing. One time I went to the beach and it was so hot. So i decide to go back hame after a little sunbathing. So i unhook my top bikini and lay there. I guess I dozed off because when i woke up it was 8 pm. So I pick up my towel, put it in my car and went to the ocean so i could piss. The waves were really coming and my bottom straps were undone. So when I run out I am completely naked. So I drive away. When I get back to my apartment. I rap myself in my beach towel and head upstairs. When I got inside I relized I had forgotten my work keys in my car so I run out and when my door closes I am naked. Unfortanatly I did not notice till I get to the car. And again I had to go pee. i thought If I ran fast enough I could make it. Though while I was running I slipped on my pee and was nocked out. In the morning some dude wakes me up. God. I ran to my apartment, and noticed most of the cars were gone and it was 11 am. And wouldn't you know it I have a note on my door with pictures of my chest and vagina and says Nice Bod. R U a hore. Signed Macayla. Oh god who got the photo.

(Rated 5.3 out of 10) with 956 votes
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On A Beach In Florida by Angélique

Since I was near the Florida coast, and had a few hours' down time, I decided to get a little relaxation and sun. It was a warm day, there was an inviting breeze, and it was still early enough for my avoiding the dangerous rays of the sun with the judicious use of sun block. I changed into my swim suit, took a large towel, chose an unoccupied section of the beach (It was before the season and a weekday), spread my beach towel for my moment to chill out, metaphorically, if not in fact (it was in the low 80's), and untied my bikini bra strings in the back as I lay down in order to avoid the tell-tale line of white tan lines.. Within a short amount of time, I heard a throat cough, and looked up to see a middle-aged minion of the law. He was troubled, but I could not tell why. I demurely clutched my upper garment to avoid inadvertent immodesty, and asked him how could I be of assistance. I find that, if I try to act helpful, then most southern police officers go into their default "be charming with the ladies mode" and it disarms them from whatever might have been my offense. He said, "Miss, I wish you wouldn't do that." I responded, "I'm sorry, I didn't know the beach was posted." Some are. He said, "No, it's just that I wish you wouldn't . . . ." He pointed at my chest while looking away. "The bikini?" He nodded. Now I was beginning to worry. Did Florida suddenly get hypermodest, a detail missed by us heathen Louisianians? If so, I was, in the words of a former President, in deep doo-doo. "Noooo . . . . You see, someone from the nearby high-rise condo complained . . . . this is a family beach, and we don't want . . . . I don't have a problem, Miss . . . . " Finally I understood. He was uncomfortable with the task of having to get after me for my having unfastened my bikini strings, even though I was lying prone and exposed very little of the side and back that wasn't already open to view! (My niñas were properly still in the cups.) This was despite the fact that no one else was around, and I would not have been judged indecent anyway, had one been around, much less someone from a distant high-rise! I thanked him, and tried to comply with his request. Unfortunately, my grasp slipped, and my top blew away down the beach due to an unexpected gust. So there was a spectacle of a topless girl and a police officer chasing a bikini top down the beach. Finally, he retrieved it, and help me to re-tie my suit. He deserved the hug I gave him. After all, it was disagreeable for him to be called on to fuss at me, and he helped me restore decency on public beaches in Florida!

(Rated 5.18 out of 10) with 766 votes
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Wearing A Girls Bathing Suit by mutt

I was always small for a boy, short and small built, and to make it worse I had more of a girls figure than a boys. I got razzed a lot in school, in high school I got taken to the showers a few times by the bigger boys, made to undress and get in with them, and listen to all the comments. The weather was super nice just after graduation, I had just turned 18, my older brother, one of his friends and my two cousins invited some kids from school to come to gramps farm for an afternoon of swimming in the stream. I went wearing cut off jeans, most of the other boys had on regular swim trunks, there were no girls there. As soon as everbody was there, my brother and his friend got me down, took off my cut off jeans, and made me put on a blue pair of his friends sisters bikini swim bottoms. They were the kind that tied on each side, and with me being very small in the guy area, they did fit me really good. I had worn panties before and liked the fit, but didn't think anybody knew about it. But like all secrets, they do get found out, they stood around laughting like mad, saying that I looked better in them than his sister did. I was embarrassed as hell, and that made them more happy. Then they all hit the water, and took me in with them, but after some pinches and a little more jokes, they started playing water ball. There was this 15 year old black kid there, and as I started swimming on down stream, he came with me. We swam around a bend and got out of the water, he started telling me how good I looked in that blue bikini bottom. I knoticed that he had a bulge in his swim trunks, and it embarrassed me knowing that he was getting hard looking at me. He started getting stronger with his comments, and as the old saying goes, one thing let to another, and right there in the grass I ended up letting him fuck me. But to tell the truth I loved what he did, untill after he got done, then the embarrassment, guilt and ashame feelings strated. We got back in out swim attire and headed back to the others, they were so absorbed in the game they didn't even know we wern't there. I saw the kid again a few days afterward, but he never mentioned anything, but that was my most embarrassing day.

(Rated 5.08 out of 10) with 719 votes
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Bouncy by Embarrassing

There was a girl in our class called aleena and she had 40d bra size. She never wor a bra and we had to do jumping and her breasts would always bounce up and down. Them when she bent down to tie her shoelace her breasts fel out of her shirt and everyone got their phones out and took pictures of it and posted it on the internet

(Rated 5.37 out of 10) with 788 votes
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