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

Bikini Prank by Embarrassing

I had gone to sleep on the beach. I was with 30 guys from my class. While I was asleep one of them had cut the straps of my bikini and as soon as they started tickling me I got up and my bikini fell off and I ran to find something to cover me up but they had taken photos and videotaped itand they put it on the internet.I was so angry and dumped my boyfriend who did it.

(Rated 5.19 out of 10) with 696 votes
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"please Use Me Freely" by mariofan

When I was thirteen years old my arch nemesis at school pulled the worst prank on me. She was pure evil as during my shower after gym class, I was knocked out cold. I only remember waking up in a closet of some sort. I was stripped completely naked, my pussy having been shaved and my mouth was covered with tape, my hands bound behind my back and a little sign around my neck that had "Please use me freely" written on it. The door of the closet was only slightly open and out of curiosity and being scared I barged out after finally managing to get up. As soon as I saw a bundle of 12th graders from school ( around 30 of them ) were all naked and looking at me. They grabbed me, pinned me on the ground and each of them pounded my virginity away. I was crying, I was bleeding, I was sore in my downstairs and behind. I was completely filled and covered in cum all around and after it all my nemesis came out to look at me and took pictures of me completely helpless. After everyone went away and I was left in that room, her older brother came along, called the police and brought me to safety. They were all apprehended and my nemesis brought to a psychiatric hospital before being sent to juvenile detention, but not before she showed the pictures to everyone at school. I had to move towns completely. I still keep in touch with her brother who saved my life.

(Rated 5.19 out of 10) with 167 votes
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Stolen Clothes At The Beach! by Billy

On a hot summer day I decided to go to the beach with a few friends. We decided to go in the water for a swim so I left my shoes and shirt along with my phone and wallet on the sand. After we got out I went to get my stuff but it was all gone! I searched for hours but I couldn't find it! I had to take the bus for 45 minutes to my house with no shoes and no shirt

(Rated 4.97 out of 10) with 677 votes
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Sex At School by andria young

Ok so this happened when I was 16. I was sorta popular in high school and everyone else was wearing mini skirts, so I decided I would wear a mini skirt without panties under it. I had a crush on this super hot guy who was the most popular guy in school and he was super sexy and a little perverted. So I went to school and I thought I looked hot, I had on a black mini skirt that barley covered my butt and a matching black crop top that showed off my cleavage. I was talking to my friend and my crush layer down underneath me and looked under my skirt. I had no clue until I heard him say damn I want to eat you out right now. I screamed and my crush grabbed my ankles and he pulled me down so I was over his face and he started licking my pussy. I tried to get away and he ended up pulling down my skirt so now everyone could see my butt and vigina. He got up and started fingering me, I was really turned on and then I started making out with him and I wrapped my legs around him and he took my top off, we started having sex. Then my principal came out and I got in huge trouble, my punishment was that I had to keep my clothes off for the rest of the day. All the guys were whistling, slapping me, and licking me. I left school crying, I was so embarrassed.

(Rated 5.68 out of 10) with 194 votes
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Shit A Brick Realy by rosestonton

Im a 24 year old girl and i went to the public toilet cuse i needed a shit so i seat down but then some girls walked in so i dident went to shit so i w8tted but when one girl went out one came in so there was about 8 girls in there and out of no where it dropped a farting shit stinky shit so alot of them shed thats gross and walked out so i pulled up my skirt and wished my hands and the only girl in there shed you so i shed me she shed yer you can i buy your knickers of you i shed y she shed cuse iv shit myself so i shed ok so i tork them off and gave them to her and she shed i think theres something wong with you skirt so i shed what is it so she shed take it off i will show you so i went in one of the toilets and gave her the skirt she shed thanks i think it will fit and i shed what you mean she shed im taken it bye so i had no knickers or skirt on and just a tank top but then i looked in she toilet bit there was shity knickers and jeans so i try putting the jeans on now im a 28 wast and thay where 24 and shit in them so i had to make a run for it to my car so i hated and i put them shity tight knickers on and i grapped some toilet roll and ran to the car it was embarrassing

(Rated 4.59 out of 10) with 711 votes
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Sister And A Change??? by ryan s.

Growing up I always jacked off to the site of my sister and her huge D cups. I did that till I was about probaly 13 or 14 years old. But once I hit puberty and I started growing my sister change. One night I really had to go to the bathroom so I ran to the toilet and I started taking a crap. I didn't even notice that my sister was half naked only in her bra and panties. She's just staring at my errection and starts to giggle. I tried to cover it up but my body was growing and I couldn't cover it all. But my sister just left. Later that night while I was sleeping(and I'm a heavy sleeper) I woke up with a start and find my sister pulling down my pants. She sees me and asks me what do I think??? I told her she's fucking crazy but then she does the most amazing thing ever she "accidentlly" falls over hits her huge boobs on the side of my bed and they pop out! After that she ask me what I think I'm all like oh fuck yeh those are fucking huge sis. She tells me to touch them touch them and so I do they feel amazing I'm getting a huge bonner and all of asudden my door bust open and my crush who is 18 (I'm only 15 at the time) comes in naked. At this point I'm fucking drolling. But then my sister just starts laughing and shows me a video camera. I was so fucking pissed off but I got to see and touch so big ass boobs!!!

(Rated 4.92 out of 10) with 690 votes
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I Had A Wild Night by P-Money

one of my friends was having a huge blow-out party and it was the biggest party i had ever been to. there were hundreds of people there. i was flirting with girl i met in the pool and we ended up making out next to the bar. eventually a couple of my friends, the girl, and I decided to have a drinking contest. i was starting to feel funny around my 10th drink. everything went downhill after that. i can't remember everything i did, but i think i lost a fight with an inner tube, and had 5 more drinks. the last thing i remember was the girl i spent all night with leading me in to a bedroom. when i woke up, the first thing i saw was a bikini hung on the ceiling fan. as i looked around, i realized i was naked, and that the room was messed up. the dresser was turned upside down, i found my clothes in the desk drawer, and when i looked to see what kind pillow was this warm, i turned red. she was naked and my head was stuffed into her boobs.i got an errection as soon as i saw her. i tried to get up and dressed, but she grabbed my head and put it back in her breasts and pretty soon we were having sex. my friend who was having the party was checking all the rooms to find anyone still here and he saw us. he said i'll just let you two go back to what you were doing. i had never been that embarrassed in my life.

(Rated 5.54 out of 10) with 718 votes
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Im A 24 Year Old Girl Now Me And My Boy Friend by rosestonton

Was out on a date so he got me and himself a ice cream me and him sat down and as soon as i got up i had a wedgie i cant pick it y hes there so we went on it was getting wose it was going up my ass so much we went to a public bathroom with one toilet so he went so i tryed pick but my jeans where so tight so i cant put my hands down my pants so i undone them pulled them down to my ankils picked it looked up saw my boy friend so i had my jeans down with rainbows knickers so he shed nice knickers so i pulled them up and got on with the date it was embarrassing

(Rated 4.74 out of 10) with 688 votes
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The Lost Bet by clocksarecool

I made a bet with my best friend that said if the Stealers won in the Superbowl(of '11), then he had to run butt naked through a rural trail in a park forest. The same fate awaited me if the Packers won. Well, of course, I ended up losing and I ran a full three miles stark naked. When I got back, my clothes were gone and I ws stuck in the middle of a city park. Worst experiance of my life!

(Rated 5.19 out of 10) with 723 votes
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Teaching Problems. by caprice

I don’t know whether this can be considered as a funny story but it was extremely embarrassing incident of my life for sure. I had qualified for IIT and secured a seat at Delhi IIT. My father was working with a multinational construction company and away from home most of the times. My mom was a senior lecturer at Delhi University and we all moved our residence from Mumbai to Delhi. We belong to an orthodox Brahmin family and my mom hails from a Brahmin family from Benaras hence adjusting in Delhi environment was not a problem for her although she was born, brought up and educated in Mumbai and loved it. I had turned sixteen and mom was around thirty eight. All the members of our family were tall including my mom who was five feet ten which was unusual for any Indian woman. She was fair complexioned and of late I noticed something about her, the lusty way my friends, her students and other men looked at her. Even some of her female students who got on very well with me, told me that they were jealous with her personality which they called as very sensuous and the males fantasized about her. Mom was a maths professor, another paradox, and a superb and passionate teacher. Her classes were instant hits and attendance was always full. Sometimes boys and girl students visited our house with their complicated problems and were never disappointed. Let me describe my mom briefly before I narrate the main incident. Mom was about five feet ten with long thick hair which hung upto her thighs when she dried after bath. She used to paint them with brown mehendi and was very fond of her hair. She was a busty woman with very narrow waist and massive buttocks. My friends used to pass remarks about her butts which made me angry. They even expressed their desires to see her breasts by arranging but I never responded. Mom usually wore sarees below her sexy bellybutton which was deep and round and was exposed when her pallu got shifted by her movements. They all loved watching her exposed back and waist between her blouse and saree from behind. Sometimes mom wore north Indian style churidar( bottom) and Kurta(top) with dupatta( Covering for top) and most of the times saree and blouse.However she was unable to hide fullness of her boobs and exposed her cleavage occasionally when her dupatta or pallu of the saree shifted.The onlookers always loved to watch it happening. On one occasion, she wore a deep ‘c’ neck kurta and churidar and gavemy friends an eyeful of her cleavage when she was bending to clean the floor with a broom in the absence of the cleaning lady.I had become fully conscious about my mom’s beauty when I entered my teens. Although my mom was very orthodox and modest in her ways, she was of friendly nature,very naive ,unsuspecting type and laughed a lot hence very popular. She was very modest and always changed clothes behind closed doors and windows. Even I had never seen her nude or semi nude.Once she was irritated by me as I left the door of her bedroom ajar when the driver of our vehicle walked inside without knocking and she was putting on clothes after her bath. Later I asked Pankaj, the driver who was of same age as me what he saw, he laughed and teased me but never disclosed but said Madhura madam ( my mom’s name)is very beautiful.When I protested with mom and asked the same, she too laughed it away. Later she told me she was just in her petticoat and putting on her bra when Pankaj had entered to give the keys. When I asked her that means he saw you topless, she giggled and said you can guess it yourself. Later Pankaj told me she had just hooked her bra and he had narrowly missed her seeing topless. I knew my friends tried to see her boobs by various means but failed consistently and were frustrated until that embarrassing incident . One morning, mom was somewhat restless and waiting for something.She was late for her usual lectures but still hung on.Then without a word she went to take her bath inside.Some time later my friend Sajid, a Punjabi muslim , an African friend who came to Delhi university like many African students and Caeser a Goan friend came to our house for one complicated calculus problem which they were unable to solve at the college and couldn’t attend classes at the college. Sajid had brought his young brother Naved who was nine years old and on summer vacation. They were regular visitors at our household and mom loved and pampered Naved. As ususal Pankaj came to collect the keys of the vehicle. I told him to wait for mom as I didn’t have the keys. We started discussing the maths problems but couldn’t make head or tale of it and gave it up and sat idle quietly when the phone which was situated opposite to the couch where we sat ,started ringing. I had a feeling that mom called me from bath for sometime but ignored it and I was too lazy to respond to the phone either. Before the rings of the phone stopped my mom came out of bath to pick it up. The sight of her literally took away our breaths. She was topless ,with only a small napkinlike towel wrapped around her waist which hardly covered her massive buttocks. It was like dream come true for them as they saw her bare boobs which were big, round , firm and stuck out without any vestige of support.They were shaking vigorously as she came hurriedly to grab the phone. Her long pinkish brown nipples were erect and dripping with water drops. As she stood with her back towards us, her right hand was clutching to the towel and preventing it from dropping down. Her long hair were tied in a tight bun on top of her head hence they had a clear unobstructed view of her long bare back , sexy thin narrow waist and long shapely legs. Slight flab below her buttocks was visible from the underside of the towel she had wrapped.Obviously she had not noticed our presence. It must have been call of her elder sister from the U.S which she was expecting very ardently.I was so dumbstruck that I couldn’t utter a word to warn mom. Pankaj and Sajid were too amused to talk ,the African enjoyed the fortuitous moment quietly and fought to hide the erection. Mom must have spoken for about ten to twelve minutes with her back to us, alternately shifting her weight on either of her legs and occassinally giving a glimpse of her nipples sideways. Shape of her covered butt was clearly visible from the napkin she had wrapped.It had started dropping slightly and her crack of the butt was exposed slightly from top. I was praying that she must be wearing at least a knickers inside to avert an ultimate embarrassment. As she turned rightways to check the time on a wall clock,she again gave us a sideview of her sexy boob. At that moment her hair bun got undone and her long hair dropped all over her face, back and front obstructing her vision also. When she tried to hold her hair with her right hand, her left hand already holding the telephone receiver, her towel dropped to her feet exposing her posterior completely. She had worn nothing underneath.As she continued her conversation for a few more seconds giving us a clear view of her big sexy buttocks when little Naved started laughing and pointing towards her. For the first time she noticed our presence as she turned back by the noise and was shocked to see us watching her.A woman ,my mom, of five feet ten was standing stark naked in front of strangers, a sight never seen by me before except in Playboy magazines. Her massive boobs were heaving with shock and her sexy bellybutton and cleanly shaven pussy were clearly visible through her hair strands . She stood with her mouth open with shock and her words were repeated OMG,as she tried to cover her private parts unsuccessfully. When she nervously bent to retrieve her towel her feet got entangled with the towel and it made her fall on the ground on her stomach. She tried to get up hurriedly but couldn’t as she must have a muscular sprain. She somehow managed to sit on her butts with her legs folded below for some moments. Her long hair were still disturbing her and she got up gradually. Then she turned to the left and drew her long hair tightly with both her hands into a bun and a ponytail. We had another sideview of her shaking boob which jutted upwards, her thin long waist, and butts which protruded backwards as she arched backwards. She seemed to have regained her composure when Sajid broke the silence. He said earnestly’ Madhura aunty we have a maths problem we can’t solve. Can you please?.’ Mom, still naked, asked me to bring her regular towel and clothes from the cupboard while her academic curiosity got better of her and she explained the problem in detail to all as I searched for her clothes.When I returned with her clothes what I saw made me burn with shame and ultimate embarrassment as she still stood completely nude and explained . All along her sexy boobs and buttocks were shaking sexually as she was giggling and talking to them in a very indulgent tone. They all had seen her completely nude, front and back.When she finished she said sorry boys I was not prepared for this situation and shook hands with them all and trotted back to the bathroom, giving me an angry look and a parting view to all ,of her ponytail swaying from one buttock to other which were jiggling sexually. Later, I protested with mom about the entire incident. I said I have become a laughing stock in my friend circle and they are making fun of me that they have seen you nude. Mom said ‘My dear, I was expecting call from Didi and forgot to take my towel and clothes. What else I could have done?. I tried to ask you to take the call but you ignored hence I had no option but to come out of bath nude.I said but mom why you didn’t run inside and kept on discussing math problem when you had the chance later. Mom said ‘Dear they had seen me nude already and they were just young boys.I was getting late for my lectures and couldn’t waste further time on that.’ To date I am unable to put this incident past me.

(Rated 5.07 out of 10) with 682 votes
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