Confess Something

Embarrassing Confessions

I sent her images of **

I sent my girlfriend images and criteria regarding women putting ** ** up guys buttholes and in their mouths because she knows I’m into that myself

In fourth grade I lifted the skirts and dresses of several girls to see their underwear, until I picked on the wrong one. The new girl wore a dress, and I ran up behind her on the playground and pulled the back of it up exposing her flowered **. She snatched it down, whirled around, shoved me to... (more)

Embarrassed.

I am back again and I am praying and praying for you and everyone else to find this again and I am trying not to be sad again and I miss talking to you like before and I will always keep praying for yous and everyone and so is my teacher and my friend and her mommy and lots of people are praying for us all and you are so sweet and kind and caring... (more)

What happened to rawconfessions.com somebody please tell me

Seriously I need to know

**

I'm a 60yo wm I love girls but ever since I gave my first ** as a young teen I get so turned on giving ** at first it was to see how big of a ** I could (more)

Boy gives me wedgie in class

I've never gotten a swirlie in my life. As for a wedgie from a bully, I've only gotten one. I don't know if I'd count the kid who gave me a wedgie a bully though. He was a mean kid, always arguing back to the teacher and not doing work but he never really bothered his classmates only occasionally. So we were in the same class when I was 9. So I... (more)

School bully

My friend in high school was a transfer student from a private school. One day in the boys bathroom, we were using the only two stalls in the bathroom, when some bullies came in. They saw two sets of legs, one in each stall, when they came in. One said for us to come out right away. Another said to grab us some shoes.
I was able to smack their... (more)

Poor me

It seems to me that nowadays everyone's a Billionaire except me . To make matters worse I'm not even a Millioaire . Oh , poor , poor me .

My ** aches after last night

I was coming home from school and my friends dad gave me a ride. I was over there the other day and I could see he was perving out on me (which is weird cuz I have smaller ** that all the other girls) and he took me in his house cuz noone was home and said I'd stay a virgin so after I got his (more)

Friends sister pulls my pants down

This happened when I was about 5.
I went over to my best friend Brad's house for some reason I can no longer remember.
We were playing some random game upstairs and his older sister, Alison, for some reason pulled my pants down revealing my Teenage Mutant Ninja Turtle briefs.
I was in shock, and they both thought it was funny of... (more)

Pantsed playing basketball

My junior year of high school I was playing basketball with some friends and some other guys I didn’t really know, but they were friends of friends, and we did shirts vs skins and I was on skins. I guess you could see the waistband and a little bit of my underwear though from the top of my shorts, because right as I was about to shoot, this guy on... (more)

Jeans fall down on mechanical bull

Once when I was 15 I was waiting to ride a mechanical bull at a funfair. I was shirtless because it was hot and wearing blue skinny jeans. I was sagging about mid ** so you could see my boxer briefs that were red and yellow stripes. Anyway when I got on the Bull it started slowly then began to speed up... (more)

Pantsed in front of kids

I was in the woods, on a hike guiding some small children (that's what we did at my school) with two of my friends, who well name Chris and Ben. Well, Ben was supervising in the back, Chris and I were up front, pointing at flowers and wildlife tracks and stuff. I've seen Chris in his underwear before, and I thought we were okay and he'd never try... (more)

Brother's hanging on fence in underwear

Jackson was not a very popular boy at school. His nerdy status was not helped by the fact that he liked to wear tighty whities every day. He always wished that he could be as popular as his older brother, Luke, who despite only being a year older had far more luck when it came to interacting with people. When Luke had been in high school, he was... (more)

Pantsed at sleepover

Once when I was 12 my friend was having a sleepover for his birthday. He told us we were going to have a Star Wars night and we were going to watch Star Wars and play Star Wars related games. I was really excited because I could wear my Star Wars underwear and no one would know. Well that day after school I took off my regular underwear and put on... (more)

Pantsed at Track Practice

I was on the track team in middle school. Now there were a group of guys that liked to mess with me and would pants me. A lot. After it happened a few times I kind of got over it but was still embarrassed because everyone could see my underwear. Well one day they struck again. I was doing my normal stretches to get ready to run and one of... (more)

Pantsing on the Street

One time I was hanging out with my friend and we were walking down the street. At a certain point my friend asked if I wore boxers or briefs. I told him I wear boxers and boxerbriefs. He asked which ones I was wearing now. I told him I was not telling him. So he decided to pull my shorts down revealing my green plaid boxers. I said hey why... (more)

Girls see my heart boxers shorts

Back in sixth grade I wore gym shorts to school because I had PE everyday. My gym shorts were also pretty short in the fact that they were only a little bit longer than my boxers. One day in class I was sitting on the floor and a girl in my class started grabbing my legs to pull me around the room. After about 30 seconds she stopped and went over... (more)

Secret sissy

So the title says it. I started with my sister's clothes and can't stop. Love the feminine feeling, girly things are so fun.

I love wearing diapers

Yes I love wearing diapers. I wear them anytime I can. I do construction work. I was left alone on a job and owner is not here. First thing I done was to put a diaper on and use it. If any of my coworkers or family would find this out it would be really embarrassing. Hope they don’t because I am really careful. I’m 54 so probably in a few years... (more)

My new friend

My new friend is very respectable & caring; she has 2 jobs; she works at a care home 3 days a week and also services men’s intimate needs with the same care. I feel less embarrassed about the latter given that her other job is so worthy

Ants in jeans

For one of my freshman biology classes we had to do field work that involved collecting samples out in nature. We took a bus to a wooded area where we were going to comb through the tall grass in a meadow to survey what insects were present. I knew there'd be some walking so I wore some black vans sneakers with my skinny jeans and a (more)

How I met my now wife

This is the true and embarrassing story of how I met my now wife back in 2006.Alot of people will think it's **.
I was 14 year old boy.I was sitting at home thinking about the hanging wedgie the nerd had get that day and I thought to myself that I haven't ever been given a hanging wedgies just... (more)

Caught on zoom call in underwear

It was an absolute mess-up when it happened. It was COVID times and I was in one of my online classes for solving math problems, more like a session for clearing doubts . There was the TA and perhaps 6 other students in the call , all with their cams on. It was a pretty important one for me, since I was quite struggling at a particular topic and I... (more)

Pants fall down at sea world

My family went on a big trip to California not long after I graduated high school. Before the trip, I went on a big shopping spree to get new clothes to wear for the vacation. Most of the clothes I bought had not been worn prior to actually getting to California. Sure, I had tried them on, but it’s an entirely different thing to try something on... (more)

Pants taken at mall left in shirt and tighty whities

I was at the local mall one day after school. and had to use the bathroom. The floor was nasty so i decided to hang my pants over the stall door while using the toilet. while I’m handling my business, someone yanked my pants from the stall door and i was instantly mortified. I found myself stranded inside a busy mall bathroom wearing just a t... (more)

Friend pulls me along grass pants come down

I was in Grade 5 my buddies and I were dragging each other by the arms around the field at lunch recess. Not sure why we were doing this. When it was my turn, my lose jogging pants were pulled down as a result of the friction between them and the grass. By the time my buddies noticed, by pants were pretty much pulled right off and pulled inside... (more)

Had to wear sisters underwear washing machine was broken

When I was around 12 years old The washing machine broke down before the laundry was done so I had no clean underwear so my mother gave me a pair of my sisters to wear and I totally forgot that I had gym class that day . As I was changing into my guy clothes I forgot about the girls underwear and a few of my school mates noticed that I had girls... (more)

Caught two retail boys with no pants on

I was once in a big clothing store relatively late in the evening. It was very close to closing time, and the store was pretty much empty except for the employees who were walking around trying to get everything ready to close for the night.
I had very little time before closing, so I wanted to hurry. There was a shirt that I was interested in... (more)

First time caught in a wedgie

This story was a long time ago when i had first gotten into wedgies. I was about 16/17 and was home alone. My sister was out with her friends and wouldn’t be home for a little while and my parents were on a trip and were gone for a few days. I decided to do some random wedgies cause i was bored. Of course I wanted to use (more)

Nerdy girl humiliated me

It was about three years ago that I was humiliated by 3 of the nerdiest girls at my high school. I was about 16 at the time. Even though I was pretty shy and quiet, I was one of the 'cooler' girls because I was an pretty.
So I was walking through some woods on the way home and saw two of the girls on the other side of the chain-link fence. I... (more)

I made myself feel disgusting

I accidentally made myself uncomfortable in a chat with online friends. It’s my fault. I got myself into the situation. We were messing around having a dirty talk battle. I, like an idiot, got myself roped into a 1v1 improv battle because I’m competitive and don’t like to back down from things. It was fun. I like banter, and I was keeping it PG-13... (more)

Handcuff Wedgie

I was playing truth or dare this weekend with a couple friends. 3 girls, 2 guys altogether. One girl was cute and petite, the other two were ok, nothing special. Someone suggested we play truth or dare and the first thing that popped in my head was the message posted a while back. But I needed to wait for the right timing. After about an hour into... (more)

Supermarket Wedgie!

In a time of need, Jason had to take a big responsibility for getting what he needed in a time like this. There was absolutely no food in the house and his parents weren't going to be home until a whole week. Taking this into consideration, he called an uber and made his way to the supermarket.Clearly he could've done the mischievous thing and... (more)

Hannah's Wedgie Torture

Her shorts had been pulled down during gym class – While they were doing stretches to limber up. Touching their toes to be precise. A dozen or so students got an eyeful of her soft yellow panty-briefs and the big blue bunny rabbit head on the ** with ‘Princess’ written underneath it. One of her... (more)

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