 | My Embarrassing MomentsA shared journal of embarrassing pictures and stories from our awkward childhood to the present. |
Public Depantsing
Posted On Wednesday March 19, 2008 By Jaylene
This was when I was a freshman in college. Me and 4 of my friends went out bowling one Saturday night. We got a lane next to a group of 4 really cute guys that went to our school. I made the mistake of wearing jogging pants. Next I made the mistake of not tying the drawstring. Last I wore a pair of really ridiculous looking underwear with snoopy on them and my friends knew I had them on. Well we were there next to these guys and some of my friends were flirting a little. One of the guys who was pretty cute was standing there talking to one of my friends. He had shorts on. While they were talking one of his friends sneaked up behind him. We all saw what was about to happen. The only one who didn’t was the victim. Well his friend grabbed his shorts and dropped them down to his ankles. He had on a pair of red boxer-briefs. All 5 of us girls just burst out laughing really bad. We were pointing and laughing at him. I’m sure he felt terrible. It was just so funny. Then a few minutes later I went up to bowl and one of my friends pulled the prank on me. Only It was when I was bowling and I tripped with my pants down at my ankles and fell out into the bowling lane. And everyone around saw me not just us. I looked back and saw them all laughing and pointing. Talking about my snoopy underwear. I was so embarrassed I could have cried.
Rate This Embarrassment: 6.4/10 (34 votes cast)Laugh At Me
Never Trust A Guy Who Wears Lace Thong Panties
Posted On Wednesday January 9, 2008 By barrymy girlfriend and i had spent the night together and there had been lots of passion. in the morning, she thought it would be fun if i would wear her panties for the day. she said that only she would know and it would excite her. so i did – a string-side lace thong panty. while we were out at a bar, we ran into two of her girlfriends. she must have told them about the panties because while one was talking to me, the other went behind me and surprised me by giving me a wedgie. she kept tugging on the thong and we were all laughing so hard. i turned several shades of red from my extreme embarrassment. to this day, whenever those two girls see me they ask, “are ya wearing thong panties today???”
Rate This Embarrassment: 7.6/10 (49 votes cast)Laugh At Me [1]
Pillory
Posted On Sunday December 16, 2007 By Victoria Williams
I should never have made that bet. Feeling cocky about my extensive knowledge of sports, I bet my wife that our beloved hockey team, the Toronto Maple Leafs, would earn a place in last year’s playoffs. They didn’t, much to my surprise — and my wife’s delight. We often bet on things, and this time her twisted sense of humor got the better of me. First, I was ordered to go to the local Goodwill and buy a week’s worth of women’s clothes. Seven complete outfits were required — 4 dresses, 3 skirts and blouses, plus some bras, panties, pantyhose, heels, and nightgowns. Next, I was to construct a pillory in the backyard. From the photo, you can see what happened next: I was dressed each day in one of my new outfits and made to stand in this old-fashioned punishment device for four hours. Pictures were taken to document my wife’s “superiority”. Fortunately I too have a sense of humor, and I must confess that, despite the long hours in the pillory, living as a woman for a week was a lot of fun.
Rate This Embarrassment: 7.3/10 (32 votes cast)Laugh At Me [2]