We've all had them - those truly hateful embarrassing moments, caught with your finger up your nose, or snooping through a medicine cabinet, sneezing snot all over a fellow passenger, or realizing you forgot to set the parking brake after your car rolls into a gully, or needing to wrap your jacket around your waist when your period unexpectedly started when you were wearing white pants. This is the place to chronicle those most embarrassing moments so we can laugh at it together. Let the whole world know your bad habits and when you got caught committing them.


I was only 16, only seen pictures of pussies and tits. The couple down the street whom I'd known for about a year hired me to do work for them when I was 15. After a few months and a day or two after my birthday, they were talking about giving me a present. She left the room and he told me that I could fuck her, if we could all play together. I was VERY unsure about that explaining I didn't like guys. Taking me to their bedroom door, she was naked, lying there with her very nice body spread eagle, her brown pussy hair being pulled apart while I could look at her pussy inside. Her tits were D cups with light brown nipples. Her brown hair on her head moved from her face, she told me to come and get a feel. I moved to her, and she told me to take off my clothes. I was naked in a flash, and her husband was naked too. I laid on the bed with her sucking her nipples as she fed each one to me, he was rubbing my butt and playing with my nipples. She moved me up and started sucking on my nipples,which I found suprisingly I really liked. I was squeezing her tits, and reaching to her pussy which was very wet.

"Take care of Bob first" she said. I looked at his hard cock and she moved my head to it. I didn't care anymore as her hand found my cock my mouth went to his. She moved around to suck me and I imitated her motions. She pulled off and said she wanted my first cumload in her hot pussy. I sensed that Bob was about to cum and he pulled out of my mouth and moved around to my butt. She was under me, I was again sucking her tits and feeling her pussy while he lubed me up and fucked me. He came, and she pulled me on top of her between her legs and quickly had me inside her. I fucked for a few minutes and shot off inside my first pussy. Though I did it with a load of her husbands sperm deep inside my ass. We all stayed on the bed, playing with each other the second time he fucked her cummy pussy and added a load to mine, he rolled her over and told me to fuck her in her ass. It was heaven. It was so tight and so different from her fertile, wet pussy.

After, she got up and went to the bathroom, I thought that was a good idea as I had to go to after the action and being buttfucked. But when she came back she was wearing a strap on dildo. Bob explained that Carol always took a mans ass if he took hers. So there I was getting sucked by Bob, on my hands and knees with Carol pounding me doggie.

That was my first time, I've been bi ever since. I still play with them both even though they are now divorced,she still loves to finger me after I have a load of sperm inside me.

  • Girlfriends Mom

    This happened a few years ago. I was at my girlfriends house after baseball practice. We were just laying in bed and I was quite tired. So I took off my pants and cuddled up next to my girlfriend in her bed.

    She had on some short running shorts with no underwear, a shirt and no bra. I had on a tshirt and white FTL briefs. I know not the most popular underwear choice but it’s what I was bought and my girlfriend didn’t mind briefs.

    We must had fell asleep right away because I woke up 4 hours later. It was 8pm when I looked at the clock when I woke up. Or only that but I noticed my girlfriend had taken her shorts off and her bare butt was up against my now hard dick in my underwear. We both were still virgins. But we had seen each other naked plenty of times or see each other in underwear.

    I had go pee bad so I walked down the hall real quick to go pee. Wearing just my shirt and underwear. When I opened the bathroom door her mom was standing there! She reached out and pinched the head of my dick through my briefs and told me to follow her! She held onto my dick as she dragged me to a room down the hall! There she had me sit down and asked if we had sex and what were we’re doing? I told her we just fell asleep and I took my pants off because I sleep in my underwear. Telling her this all while I’m sitting there with my tighty whities tenting. She hands me over a towel to cover myself up with.

    She explained to me that she was worried we were having unprotected sex. She saw her daughter was naked from the waist down and I told her I was asleep when she took her shorts off but I had known she only wore a shirt to bed with no panties or shorts. I told her we both are still virgins, her mom was surprised. I told her we had been waiting to have sex for a few years now with each other. I told her anyways I have a box of condoms in my bag that I carry and her daughter has some in her closet too. Didn’t tell her that we were planning on having sex the next day when we were going camping.

    She said alright good. Then she got up and said I better get back in her room before she wakes up. Her mom looked down and told me to adjust myself before walking back to her room because my briefs were gaping open and things were visible. I looked down and my balls were visible! I was so hard that I was tenting my briefs that far open! I reached in and adjust real quick. Pulled my dick up into my waistband. Her mom also mentioned that her daughter had scheduled her first waxing appointment for tomorrow morning. I was surprised to here that and I told her mom to talk her out of it. I liked her bush that she had! Her ..(continue confession)

    Getting Caught Well Sorta

    I’m still a virgin with a very over active sex drive. So I masturbate a lot.

    I was with my mom visiting some of her family over the weekend. We were staying in a hotel. I sleep in just my underwear, I wear briefs. Typically colored ones but I do have tighty whities too. No big deal really, my mom has seen me in my underwear at bedtime for years.

    I wake up very hard every morning and typically masturbate to get my mind off of it first thing. But staying in a hotel I don’t have the privacy for that so I went without cumming for two days! Hard to do for me! Honestly my mom knows I masturbate a lot, she knows about my sex drive.

    My mom saw me with morning wood both Friday and Saturday in my briefs. No biggie, it’s natural. Brought white briefs on that trip so I guess it was a little more visible then usual.

    So on Sunday day morning I was up and went pee before my mom showered. We were going to church with her family so we needed to dress up a bit. I had morning wood and didnt think any thing of it. But my mom comes out of the bathroom before she showered setting the box of tissues on the bed I was in. She told me to drain my pipes while she was in the bathroom because she didn’t want me to get erect in dress pants. I fully understood that, hard in dress pants isn’t good. Briefs can’t even hide that. I wear briefs because I’m hard so much, it’s the only underwear that helps contain me.

    My mom knew it had been a few days and she knows how I am but it was really embarrassing having her hand me tissues and telling me to do that. It once she shut the bathroom door I lowered my briefs down and masturbated. I came all over myself. Bad decision because I git cum on my stomach, chest and on the bed. I was wiping cum off myself when my mom came out of the bathroom.

  • Caught Red Handed

    Growing up we had a boy next door who was eight years older than me. From my earliest memory I was in love with him. He ignored me, but when things were quiet he let me hang out with him, take me to Baskin-Robbins, go to my soccer practice. Thanksgiving when I was 16 was my moment of truth.

    It started with pulling my skirt down to cover my legs, telling me to take off my glasses, pulling me to him to ask me to go get him some snacks. My need to be hugged was on overdrive, all I wanted was to have him hold me tight. When he put his hand on my thigh I let him run his hand up and down until he was running his hand across my butt.

    We went to the back room where we got on the bed, this time he put his hands under my skirt and pulled my panties off before eating me. He got on his knees, lowered his pants and with his wicked erection nailed me to the bed. We got dressed and returned to the living room to watch the game on television.

    That night, back in my house my mother came to talk to me. Since I was AWOL she went looking for me, the door to the bedroom we were in was unlocked and she opened the door and saw us. She left us alone but not without telling me that I hadn't made love, I'd been fucked.

    He Embarrassed Me, Now I Own Him

    I worked for an energy company in their financial reporting department. I went home early due to lady's problems. At nine that evening my boss knocked on my door, I was in a nightshirt. He walked in, told me to get on my computer I needed to add a post closing entry and rerun the reports. Before I could even get my act together he asked for the bathroom and headed into my bedroom, bed unmade clothes on the floor, into the bathroom with my panties soaking in the wash basin.

    My headache went from a 2 to a 10, my heart jumped out of my chest, he walked back into my living area asking me if I had gotten the change updated. Never again did anything embarrass me with him, financial, emotional, physical, from that day on he heard everything, he had to discuss anything and everything, he heard words out of me that women never use in mixed company, he had me at his house on weekends, overnights, holidays, he saw me in shorts, braless in nightshirts, no make up, doing my nails in his bedroom.

    When I asked him for sex, he stood at the foot of the bed asking me if I knew what I was doing. I told him to get on, I did anything and everything, until his comfort zone was destroyed. He took me for granted, took away my safety zone, now he has the tiger by the tail and he's figured out he can't let go.

    My Angel

    My school had a field trip. We went to a state park on the school bus. When we got there we got out in the parking area, there was just a one toilet bathroom for the boys and one for the girls. I had been holding it for a long time, the line was twenty deep, I guess it was my look, my crossed legs, that I started to cry because I was going to wet my pants.

    A boy saw me and he grabbed my arm and shoved boys right and left, knocked the boy at door out of the way and pulled me into the boy's bathroom. The only words he said was 'I got sisters nothing I haven't seen' and he yanked my pants down and sat me on the toilet. Once I started going, I couldn't control myself and I got my panties wet but my pants were far enough down that they stayed dry.

    He helped me get out of my pants and he held me up while I took my panties off which he stuffed in the trash can below the trash that was already there. He washed my face with his handkerchief, combed my hair with his hand and straightened out my shirt so I looked presentable. He opened the door and led me out by the hand and took me over to my class. 'Are you going to all right? No one can tell you lost your underwear, if you need me I will be with my class over there'.

    I was 12 in the seventh grade and I still have a crush on him.


    I love honey dew tits, hot melons and I like perky pointy banana tits and jelly wobbly tits. I love to put whipped cream and ripe raspberries on her nipples. well that is how I fancy it while I bake at the shop with her. I orgasm in the toilet to her nude photos. Her honey dew whooping big tits really match my jackfruit hanging balls.

    Hooked Up With A Woman In Her 20s

    This was my first time having sex in a few years so I was definitely very horny. We got back to my place after a date and I was ready to go. As we are stripping I ended up in just my underwear. Plain fruit of the loom white briefs. Tighty whities some call them.

    As I’m kissing her and feeling her ass in her thong she reaches down to my crotch. She then makes fun of my underwear choice. I was unaware that anyone made fun of a guys underwear after middle school? I took them off and tossed them out of the way and had sex with her.

    But I’m still surprised underwear is that big of a deal. I like support a d briefs provide the best support for me. Plus I dont like fabric on my thighs. Is wearing white briefs something I’m gonna have to worry about with future hook ups?


    I was working on a friends pare to suv with him yesterday. We’re were at my house since I got lots of tools. It was hot and humid out so I was wearing shorts.

    So as we are working on the vehicle and I’m thinking nothing of it. I typically wear briefs for support a d modesty especially when wearing shorts but being so humid I took my briefs off earlier in the day. I pretty much forgot I had taken them off so when I was laying on the ground underneath the vehicle I figured anyone would see my briefs through my shorts leg hole.

    But my friends dad says hey your penis is showing. I feel down there and realize that my shorts slide down far enough that my penis was stinking out the leg hole! So my friends wife saw it too! And my friends mom. How embarrassing that was.

    Throughout working on the vehicle I did see up my friends dads shorts as he was standing above the vehicle while I was underneath it. He had white briefs on under his shorts. Not surprised by that, that’s what older guys always wear.

    I pull my shorts back down and put my penis back in them and continue working.

    One In The Oven

    I am 20, during summer break I house sat for some friends of my parents, their neighbor who is retired invited me over for a steak on the grill. I returned to my house sitting duties the next morning.

    Now I am expecting, confirmed by a OBGYN, 13 weeks, I know the exact day. Baby daddy is Retired, AARP, SS, Medicare. He is pretty excited. I know he will respond financially, my parents are not going to be so understanding.

    I am embarrassed, but excited. Baby time just came along earlier than I had thought.