Embarrassing Other Stories

Crossdressing Dare

On a senior trip to New York, all of my friends, girlfriend, and tons of other people went with me. My senior principal and history teacher were both with us as well.

Anyway, we were all in the apartment in my room late at night and I got pretty smashed. While I was drunk, we all decided to...

A Wet Massage

I'm 16 years old, and I was out with my girlfriend one time, and she wanted to go to this spa. well, she persuaded me to go, so we entered. she automatically went to the spa section, but I found that it also had a few massage tables. I figured I'd get a massage for the heck of it, so I went over. so...

Naked at the pool

Hi my name is aaron and i am 17years old. one day 5 of my mates asked if i wanted to go swimming with them. i said yes.

when we were getting changed i noticed that my mates had the swimmies underneath their clothes so they got changed really fast. when i was in the middle of getting changed...

Problem With My Aim

About 1993 I was teaching in a school and really, really hard up. I was living in the house of one of the other teachers, a woman who was about 15 years older than me. The situation was awkward, because she quite fancied me, and was basically letting me live there because she hoped something would d...

Cheerleader for the day

My name is Barry and one of my most embarrassing moments ever was when I bet my friend Brittany on a football game a few years ago. We agreed that the loser would have to do something for the winner (as long as it was not illegal). I told her that I was not worried because "the only sport females ...

We wont look!

im 15 and male, and this happened when i was 11

i live in a block of flats. so i was playing around downstairs with a girl and a boy, and i needed to pee badly. but i didn't want to walk all the way upstairs, (12th floor!) and most of the place was visible to maids and guards and the cars. ...

Stripping Soccer

One time me and my team were playing soccer, we are a great girls team all aged 19-20. Anyway, We were losing one game 1-0 and it was quite late in the game, I ran down the side and scored a great goal! Then just a couple of minutes later I scored again, just before full time. It was great! My team ...

Fart prank gone wrong!

I remember when I was 13, feeling a little bored one summer's day, and thinking it would be funny to bother my older sister, Rebecca, and her friends Wendy, Sarah, Amanda, and Michelle. They were all 15-16, and over at our house hanging around with my sister. I had a real crush on Wendy and thoug...

Caught..in a thong!

I went to a party at my friends house because his parents were gone for 2 days. We played truth or dare and one of the kids from my school dared me to go up into my friend's parent's bedroom and steal one of his mom's thongs. I had to put on the thong and wear the thong all night long. Well the kid ...

The Exchange Student

Through our school we got an exchange student from France. She was a pretty girl who could speak quite good English but was not well understanding American customs. Like the fact that you do not strut around your host's backyard butt naked. One day my friends were supposed to come over to meet her s...