Embarrassing stories involving nakedness, humour, sex and public humiliation

Funny Stories & 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.

Can we tempt you to share your embarrassing story with our readers?

Showing 10 stories, ranked by: Random (click to retrieve another random set) - Top rated - Least votes - Most recent - Most votes

My Most Embarassing Moment by Tim - Feb 5 2007

I experienced my most embarassing moment a few days ago. I was with my girlfriend at school. School was over and we were walking around the grounds. We leaned against a banister. I leaned in and kissed her. It was so perfect. Suddenly we heard clapping. I heard a deep, deep voice. We stopped and turned around. It was our principal. He said "No, no, no stop doing that. Don't you dare do that on my school grounds. I won't allow it! Never again!" I screamed "Sorry sir" and we ran. He thankfully didn't realise who we were and he didn't say anything afterwards. Thank G-d because the last time he caught my other friend kissing his girlfriend he gave them an entire lecture and even phoned their parents. I'd die if he phoned our parents because my girlfriends parents don't know about us being together! Anyway we told the class and they laughed at us and we got over it the next few days.

(Rated 5.7 out of 10) with 268 votes
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Worst Truth Or Dare! by SerenaLove - Aug 25 2014

Now I've had a lot of embarrassing moments, but this is definitely in my top ten. My friends and have this Truth or Dare Saturdays where we gather a few people and play. One time, I was wearing a tube top that showed my belly and a short skirt with purple knee socks going up to my thighs. The way we play is that a normal dare is given to the person, if they refuse to take it, then its a double dare, which is much worst, and if they refuse THAT, they have to do anything anyone tells them for the remainder of the match. When it came to one of my dares, I was dared to flash my breasts for a few seconds in front of everyone, including the boys. I refused, because at 16 I didn't want to well... show anyone my body, considering a lot of people considered me to be perfect in terms of my body, because I work REALLY hard to keep it that way, but I regretted saying no to the dare right after, because I was now dared to strip completely naked for the rest of the match. I didn't want to have the third stage of refusing the dare... so I did it. I took off my top, showing everyone my breasts and then my skirt, showing everyone my thong. I was very hesitant about taking those off... but I finally managed it, showing everyone my shaved downstairs. I was told that I would sit down, with my legs stretched and that I wasn't allowed to cover anything with my hands. Everyone could see everything, and it was so humiliating! I only had my knee socks left, and I REFUSED to take those off. No matter what,I refused to show everyone my body COMPLETELY exposed, even if they were just covering my legs and feet. During the same match, I was asked to make out with the guy right next to me for five minutes. He had his hands around my waist and sometimes went lower, and I had to press my naked body against him while we kissed. It was so humiliating that I didn't play for the next two weeks with them...!

(Rated 5.72 out of 10) with 194 votes
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Privates Exposed!! by Shinobiwun11 - Dec 20 2012

I was at a huge party with some friends. It was the biggest party of the year and everyone was there. This girl I really liked was having shots with me and flirting a lot, and she wanted to fool around. So we went to a room and started messing around. She took off her top and let me play with her privates, and then she started taking off my pants and pulled my underwear down. When she did that and looked at my privates, she gasped and her eyes got big and I guess she was excited at how big I was. It must have really turned her on and we started having sex. I started to put it in her and it wasn't easy, she was really tight and it wasn't going in. I asked if she was a virgin and she said not even close, so I got some lube but it wouldn't go in. I pushed harder and finally the head went in and she started screaming. I didn't think I was that big but she stopped me and said she couldn't take it. I was disappointed and she felt bad so she tried to give me a bj, but she couldn't get much in her mouth, so we got dressed and went back downstairs. she went to her friends and I went to mine. Later that night when more people left, her best friend grabbed me and asked if she could see my dick. Her friend told her I was big and she wanted to see, and she grabbed my crotch and she got really excited. We went up to another room and she wanted to have sex. I told her the last one couldn't take it and she said she could, so I started putting it in and it took a while but finally it got partly in and we started having sex. I was so drunk I started pounding her vagina like crazy, and she was screaming her head off and cumming all over the place, and I looked down and she was bleeding. I asked if she was on her period and she said no, so I must of been tearing her up pretty bad. Afterwards she said I was by far the biggest she's ever had and couldn't believe I was so big, and she never came so many times before. She was freaky and wanted to take pictures, so she snapped a few with her Iphone. I told her to keep them private and she said ok, but the next week I had random girls coming up to me wanting to see it. It was flattering but very embarrassing and I felt like a piece of meat and being used for my large member. I am not a mindless sex animal I do care about other things, it just annoying to deal with that all because the girl I liked couldn't take my penis.

(Rated 5.08 out of 10) with 258 votes
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The Lost Bet by clocksarecool - Mar 20 2011

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 5.45 out of 10) with 331 votes
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Princess Leia Bikini Story by the listener - Nov 12 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 cute in a bikini." That was the most embarrassing moment of my life.

(Rated 5.73 out of 10) with 201 votes
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My Mom Saw Me Naked!!! by Thinnerkat - Feb 18 2014

One day in the last summer I was 15 and it was just me and my mom home and I went to take a shower when I got out my mom went to sleep then I walked past her but then she got up and started to tickle me and I loved the feeling when she touched near my tip of my penis! I accidentally dropped my towel, butt naked I tripped over the towel on my back my mom seeing everything and she was wearing no panties just a long shirt and I saw her vagina and I got hard and she noticed and said I know your embarassed so she said its fine to get horny when you see one since she believes you should get used to looking at a girls private parts at a young age she let me jerk off and touch her vagina and after that I'm never embarassed for her to see my penis I love it because now I want to have sex with her!

(Rated 5.68 out of 10) with 475 votes
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Sister And A Change??? by ryan s. - Dec 3 2011

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 5.18 out of 10) with 315 votes
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Towel Trippers by lepord & T-rex - Mar 28 2013

i was at my cottage with my mom,grandmpa,uncle,his kids,his friend and her 2 kids.her daughter is my age and supper hot her name is Kiara.for a few days we started to get used to eachother more and hang out alot.But one day my 2 little cousins were fishing on the dock, i was swimming near the shore and kiara was playing with her little cousin just a few feet away from me.we were joking around until she told me i had a fishhook caught to the butt of my swim trunks.i didnt beleive her until she pullede on the line i was attatched to and my little cousins at the end of the line holding the rods and laughing their heads off.she had to bend over and try and get me unstuck.it was one of those big hooks with 9 tiny hooks to get out.after 15 minutes of that they didnt wanna come out so she yelled for my mom.i had to strip naked on the small shore while my mom wraped a towel around me.kiara didnt look but when i was going into my cottage my cousins thought it would be funny to step on my towel while i was walking.unfortinatly i wasnt holdin g on tight enough and the kids ran away with my towel. so there i was standing butt naked penis and all,exposed infront of a girl i liked. and get this i was in too much shock to cover myself and she was too much shock to cover her eyes.i turned blood red. :$

(Rated 5.75 out of 10) with 345 votes
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I Love Football But Ummm I Dont Like Knicker Football by rosestonton - Aug 23 2012

Now im a 24 year old girl love football one day me and my roomate was play take football like per time you get a goal v you you take off a pair of clothes and there is 15 shots now max you can have on is ten so i had shoesx2 socksx2 knickers shots bra top gloves x2 and the losers has to bent over with what clothes thay have left and take 5 shots to the ass if it misses its still a shot so any way i lost my gloves 1st it was ok saved one lost my shoes lost my socks saved one lost me shorts i was getter under comfitable btw i had granny knickers on that go right up near my tits so next i lost my top she got a nerver one in so was it going to be my pussy or my tits so my bra came off i had 3 more i saved one then lost my granny knickers i had one more naked and lost so i bent over naked she can kick hard so she missed 1st going for power missed the 2nd i shed i bet my ass is ok today so one more shot she missed i so i jumped in joy then i looked she had my clothes and went in the house and locked it so me naked outside grate so about 20 mims latter she shed you can come in she asked but 1st can you pick that 2p up so i bent down she smacked my ass with a fly hitter thing so it hurt like fuck

(Rated 4.83 out of 10) with 242 votes
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Boobs Exposed by Savannah T. - Nov 21 2011

The whole 7th grade was at a campsite in the woods near the city. We were in our cabin and the other girls were convinced that I stuffed my bra. I kept explaining them that I didn't stuff my bra at all! They didn't believe me. "Prove it!" they said. So I grabbed my shirt and my bra and I pulled them up and showed the girls my boobs. "There! See? I don't stuff my freaking bra!!" I said. They were probably expecting me to poke my bra or something, to prove I didn't stuff but instead I gave them the shock they didn't expect! Then we heard a knocking on our door. We opened it and my crush, Brian, was standing there. He said, "Uh, what were you doing? Cuz I just saw you... um..." And then I realized the window had been open! My crush saw me flash my boobs!

(Rated 5.14 out of 10) with 253 votes
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