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.

Caught Jerking Off

A few years ago i was hanging out at my best friends house who had a younger sister(only by a year) She was hot and she knew it. She would walk around in see through short shorts and wear bright colored thongs. This one day was a day after a night of drinking and i get super horney very easily the day after drinking and my load is usually extra large. We were in the kitchen and i was leaning back on the counter with my arms crossed talking to her brother. she entered the room and was standing in front of me making something to eat. still talking to my best friend turn to grab something and shot me a cute little smile and continued making food. Her brother went to washroom which was like 6 feet away and as soon as he shut she "accidentally" dropped something in front of me saying opps . As she bends over to pick up the item her bright pink thong is showing a lot and this was driving me crazy and started to get hard. I heard the toilet flush and she went back to making food and i went and sat down on the couch to hide my boner also with a blanket on top. She then sat next to me. My buddy then got a text from his dad saying he needed a hand in the workshop out back he said he would be right back. As soon as he left i jumped up and went into bathroom downstairs saying i just wasn't feel good probably from drinking the night before. But i couldn't take it anymore. I pulled my pants down and started jerking off. i was in there for a bout maybe 4 or 5 minutes. I'm jerking it like crazy and I'm cumming doesn't the sister open the door mid cum and she is literally watching me cumshot for cumshot. She did scream, yell or run away she was just staring at me cumming. She then shut the door went to her room and i cleaned up and went home. I did't go back over there for about a week but man it was awkward when i saw her again.

  • She Might As Well Be My Conjoined Twin

    So I'm going to call this aggressive affection. She is our maid's daughter. She is my age and they live with us since she was tiny. My mom doesn't want her to feel less because she is the maid's daughter so she's been raised more like my sister. She doesn't know that she isn't blood. The other night she got in my bed, again, snuggled up until we were breast to breast, in bed we don't have bras on so as you can imagine she wants to rub boobs. She wants to snuggle up and kiss.

    She joins me in the shower, lays her head in my lap, holds my hand when we walk. I 'love' her, true, she's as close as a sister, but she 'loves' me in a different way, she wants to kiss, rub up naked, and I'm not kidding, she has rubbed her face in my crotch when we are watching television.

    We are going to college together next year. We will room together. I don't have an independent social life, aka, boyfriend because she hangs on me. If I dated, she will come along. I might as well have a conjoined twin.

    He Was Too Big

    So let me start by saying that I'm a very petite girl. I'm 5'2 and weigh 97 pounds. I'm a 32 B cup with strawberry blonde hair that's naturally curly and I have blue eyes. I met this boy I really liked when I started my first year at university. After dating for 6 weeks I decided that this would be the night I would have sex for the first time. Mind you, I had been masturbating since I can remember and even have a small vibrator and real skin dildo that I use for masturbating. I took my own cherry years ago. I have sucked a couple of boyfriends in the past. But this was THE night I would get fucked for the first time. I was excited and nervous because I really liked him and thought that there was long term potential, and honestly I wanted it bad. I had never seen him naked yet, nor him me. So we were making out and it's getting hot and heavy so we go into his bedroom and we start taking our clothes off. It was dark but not too dark as he had a table lamp on his nightstand. I was just taking my bra off and I looked over to see that he had his pants and underwear off. There it was, a huge hard penis standing straight out! It had to be a foot long and as thick as my arm. It was probably longer than my arm from hand to elbow. I just stopped and said, I'm sorry honey. THAT IS NOT GOING IN THIS! I put my clothes back on and left. He was begging me to just wait and we can take it slow and so on. I'm sorry. No way. I felt really bad. Really bad. I was crying all the way back to my dorm.

    I told my friend what happened and she said I'm lying. I'm like go and see for yourself.

    I guess she did because a week or so later she says... You weren't lying at all! They have been having sex all the time since then. It makes me mad at times. But I'm glad he has a girl that likes what he has. It was really just told big and scary for me to even try. I'd never be able to fit it in my mouth even.

  • My Mom Recently Found Out I'm Gay

    I’ve always kept my sex life private. I’ve known I’m gay since I was 13. I was never attracted to women. Plus having sucked my first dick in high school made it very clear I was attracted to guys.

    I have an apartment that my mom bought where I go to college at. She wanted a place there to come visit plus she didn’t want me living in a dorm room. I don’t blame here there, I didn’t want to live in a dorm. So this is my second year in college and last year I lost my virginity. Easy to do when you have your own place!

    This past holiday weekend I had my fwb over for a night. He came over on Friday and was staying there over night. He’s 44 and a total top. Nice hairy daddy type. Friday we had sex then went to bed. Come Saturday morning we were having sex again. Only I didn’t know my mom was gonna show up Saturday morning!

    So as my fwb is on top of me fucking my butt I heard the apartment door open. I got up in a hurry. Put on my underwear and a shirt to see my mom there! She noticed my fwb in my bedroom. Naked and saw his hard dick. He looked kinda surprised too. I shut my room door. My mom was kinda shocked. We went into her room and she asked if she walked in on me having sex. Plus there was two boxes of magnums sitting on the kitchen counter.

    So right then my mom asked if I was gay and I told her I am but was afraid to tell you. She just hugged me and said you should had told me years ago. My fwb was still in me bedroom and my mom asked where I met him and his age. Then said you like older guys I see.

    Then here I am taking me mom I go my bedroom to meet a guy that fucks me. He’s naked because his clothes are in the dryer. He just kinda covered up his private parts with a towel bad he met my mom. He informed my mom too that his clothes are in the dryer. She said she was told that already and she’d leave us too alone.

    When my mom walked out he revealed he was still hard so I got back on the bed and he fucked me till he came. As I’m carrying a cum filled condom out into the kitchen to throw it away my mom sees it. She just says I’d assume that’s his. My mom quickly caught on that I’m a bottom.

    Later that day she did joke and say I saw that your a fan of more bigger men. She was referring to my fwbs dick size. I just smiled and siad I didn’t know he was hung till we first had sex a few months ago.

    Then we got into talking about sex, anal sex, when I knew I was gay, when I had my first sexual experience, when I lost my virginity, etc.

    Caught In The Act

    Ever since I can remember I have been masterbating as much as I can. I just love coming so much it's all I can think about. I even do it in the bathroom in school. My mom caught me with my hair brush in my cooler yesterday in the bathroom at home. I thought I locked the door but I was just getting into it feeling the tingling that happens just before I explode and then OMG Annie! What are you doing??? I was soooo embarrassed I don't think I'll ever recover. Mom had a long talk with me and offered to get me counseling. But I told her it was just the second time I did it. I didn't say since I got home from school though. But it was too embarrassing to talk to her about the birds and the bees and that I can hurt my lady parts as she put it. I just said ok mom, it just felt good and I wanted to try it again after I did it a week ago.
    So now I have to be careful to not get caught. I already comed like 5 times today. 3 times before I got up for school and once in the bathroom at school and one just before I wrote this. Mom doesn't get home for a couple more hours. I love half days!!!

    I really want to get a dildo but I don't have a way to get one without mom finding out. I can't wait for three years before I'm old enough to go buy one. Any suggestions how I can get one?

  • Underwear In School

    Was anyone else embarrassed to wear white briefs growing up? Like in middle and high school it seemed to common for guys to be embarrassed about wearing briefs in the locker room. Just does t make sense how a style of underwear could cause some much embarrassment. Briefs seemed to have a bad rap and still do.

    I’m a life long briefs wearer, wore only white growing up but since my mid 20s I’ve mixed colors in . My oldest nephew is now experiencing those embarrassing times, my brother grew up wearing white briefs too so obviously that’s what him and his wife buy their son. He came to me asking if I was embarrassed about my underwear in school. He knows I wear white briefs and seems to be a lot more comfortable asking me about this situation since I’m a lot younger then his dad (my brother).

    I pretty much told him it’s just underwear and briefs definitely support the best. I asked if he found briefs comfortable and he said yes. So I told him to just wear them proudly then, dont let peer pressure make you think you need to change. He told me he doesn’t like boxers and doesn’t like how boxer briefs look or feel. He tried a pair last month. I asked if he’d feel more comfortable wearing colored briefs instead and even offered to buy him some. He walks to my house every day after school and waits for his dad to pick him up after work or his mom. He’s too embarrassed to ask his parents for colored briefs so I told him he can take a pair of colored briefs home, put them on in the morning before school then leave them at my house and I’ll wash them for him and he could wear his white briefs home.

    So Sunday when I was at the store I got him a pack of colored fruit of the loom briefs. He wears an adult small. So yesterday I was at my brothers house and I secretly gave my nephew a pair of dark blue briefs to wear to school today. He definitely was thankful. I told him to put a pair of his white briefs in the bottom of his book bag that way he can switch to them after school.

    Will have to see how his day went today. I guess I forgot how embarrassing things can be as a teenager. He’s a quiet shy kid

    I Lost My Compass And Messed Around With A Woman

    After my gym reopened i joined a spin class. There were just six of us at the 6:30 class. The woman next to me was a fitness queen, marathon runner, she looked like she was fat free all over. I had gained 20 pounds and was spinning to work it off my thighs.

    That one day when she approached me she wasn't wearing underwear or leggings. As my brother referred to it she was wearing a lip reading leotard. Every move was spelled out in detail. She talked to me invading my personal space and touched me between my legs asking me if I wanted to go with her to the Starbucks next door.

    And just like that she kissed my lips and she grabbed her gym bag, took out a pair of jeans and pulling them on she patted her ass and asked if I liked. Nothing so forward had ever happened to me before. I felt like leaving but something else took over and I went with her to Starbucks. She touched my hand, knee, thigh, patted my cheek, and after excusing herself for the bathroom came back and kissed me on the lips.

    I don't like saying I was helpless, but I was. I followed her to her condo, showered with her, and let her take me apart on her bed. Before that only once before had I experimented in college. After I got home I sat on my couch for a very long time thinking about what I had done. I decided not to go back to the gym. Usually I share everything with my boyfriend, but I kept this to myself.

    It haunts me, I've not seen her again. I don't go near the gym. I'm 100% heterosexual, I swear.

    When Your Young

    19 and I got a job in an insurance office. The owner swatted my bottom one day, and realized I had a pad in my pants. He drew his hand back and looked at me with eyes of disgust. Later that day the office manager talked to me. If I was on my period I should wear dark pants and high waist cotton panties, so he did not have that experience again.

    He liked me well enough, and during my period I made sure to maintain a low profile. If I was giddy and affectionate and wore a dress or light pants he new he could pat my bottom, if I wore black pants and stayed at my desk he knew not to touch me.

    Inappropriate Behavior

    I changed jobs to work closer to home, I worked in Human Resources at a bank but my new job was in accounting at the regional offices of a grocery chain. The dress code at the bank was office casual, skirts preferred over pants. The dress code at the grocery chain was informal, very informal. Most of the women at the bank were naturally attractive, and they took care of themselves, hair, nails and made up. At the grocery chain the women did their best to look like lower class housewives, which is pretty much what they were. It was shockingly different, that's one of the penalties of remote recruiting. When I brought up the subject of mandatory bras the manager, female, told me to mind my own business.

    Several weeks into my job I was in the women's restroom, a two stall bathroom. I was wearing a nice pair of black slacks, and a nice silk top. And pumps. My hair and nails were done, and I had professional training on makeup. I looked at myself in the mirror, admiring myself really, compared to the other women. I didn't notice my manager who had been in the other stall. "You think you are high class don't you, to us you're a bitch". And with that she walked up to me and grabbed my crotch. "You like that don't you".

    Nothing in my training had ever prepared me for that. The chain of command required me to report any harassment to my boss. I knew the VP only in passing, I couldn't see myself telling him I had been grabbed by my pussy by my boss. I decided to quit instead and go back to the bank. At least there if I was going to be groped it would be by a man.

  • Had To Come Out To My Kids

    So I've been with my girlfriend now for a couple of months. I'm totally in love with her and she me. We are both single moms.

    We have been keeping a low profile as she had to get used to the idea of being in a committed relationship with another woman.

    Well my kids noticed how much time the two of us have been spending together and my daughter just came right out and asked me if we were a thing. I tried to play it off but my daughter knew, so I said what if we were a "thing" as you put it. She very nonchalantly says oh that would be ok. I like Mrs. V.

    My son on the other hand didn't take it so well when I told him. He said mom, that's gross I don't want my friends knowing my mom is a lesbo. We had a long discussion and as embarrassing as it was I had to tell him a lot of things I did not ever want to. Ultimately he said ok but please keep it in the family. He doesn't think he can handle the teasing he'll get in school.

    So it's just us that knows. I definitely feel better not having to hide it from my kids. Do you know how hard it is to not kiss or touch the one you love for hours on end because your kids might see?

    As embarrassed as I was, I'm glad to be out now. But it may just be at home. Out in public, we are just two close friends. I'm ok with that for now at least.