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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.

- Embarrassing Moments -
Straight Female / 36

One Day Refresher Course

I am 36 in decent shape and like to show off a bit. I do like the attention but this time I took it a little to far. I have to do this refresher course every year most of the people there are guys some young some old myself and another women where the only 2 women I’m a class of 40. I was late so I ended up at the back of the class and was leaning against a high desk. Every one else was sitting except myself and 2 older gentleman. I wore a dress about to my knees nothing super sexy just a snug fit. The lights went off and this class is a lot of 20-30 minute movies and some explanation of what happened and what could be avoided. Being in the back in the dark made it really easy to go with out being seeing. I noticed the younger of the 2 guys next to me kept looking at my ass. I made sure he got a good view and made sure to lean forward on the high table desk we where at. Figured I’d show off a little and give him something to look at. It was quite and dark when I though I felt a hand graze my ass. Didn’t say anything or move then I felt it again. This time a firm squeeze thy made me jump a bit. I was about to look over when I felt a hand up my dress and he had good aim and hit the dead center of my slit. He rubbed fast through the fabric and I did everything I could to stay quiet. I then heard him right next to my ear telling me what a good little slut I was. Shocked wet and horny I didn’t say anything kept my mouth closed and eyes shut. He slid 2 fingers in me and went slow. I should have moved but I did not. Then fingers came out and his middle finger went straight into my ass. He hit his knuckle it hurt a little but again I kept quiet. 2 hours into the class i had been finger fucked and my ass fingered. We took a break nothings a said I went to the restroom and rubbed my self to a shaking orgasm. Went back after 20 minutes and again was finger fucked this time I had removed my panties. Long story short at lunch I was fucked in his truck for close to an hour. Fingered until the end of the day. Was supposed to meet my husband for dinner. Told him i was going to be late because the class ran late. I was a little over an hour late got to the restaurant leaking cum form my ass and pussy. To make things worse the guy stold my panties so I was a sticky mess. I had to go shower and wash up. I’m hoping that next year I can do this again. Made the class tolerant

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# 74203 - by Tanya / October 23, 2024
    • - Embarrassing Moments -
    Straight Female / 38

    Lesson Learned

    In my senior year of high school we were at a pool party for one of my classmates. Horsing around I fell into the pool. I had on a thin white top, no bra. In a second I was pulled out to the clapping of my classmates. I tried to cover my chest with my arms, but a couple of the guys pulled my arms away and everyone laughed. Except one boy, a foreign student in our class. He covered me with a towel to the howling of the other boys.

    I learned something that day. Boys, and girls, really have a thing about girl's tops. It's irrational. Stripping you of your dignity isn't on their mind, not if there are titties and a wet shirt.

    I've used my tits to open doors, make sales, disarm jerks. That boy that saved my dignity, he is the one that fondles my tits, and earned my cherry.

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    # 74051 - by Vivian / October 16, 2024
    - Embarrassing Moments -
    Straight Male / 32

    Big Hard Erection At Dermatologist

    Having suffered with skin issues since I was 19 I used to go to a dermatologist but stopped going years ago. So ultimately decided I wanted to get things taken care of once and for all

    Set up an appointment at a new local dermatology office.

    Went after work one day thinking I’d just be getting my hands and arm examined since that is where all my issues are but after getting checked in the nurse got a gown out and said take everything off but your underwear. Had I know that I would had put on nicer underwear

    So as I sat there in the gown with just blue fruit of the loom briefs on the dermatologist walks in. Super good looking woman. And her nurse follows her in. She explains the first visit is always a full body skin check

    So off comes the gown and I’m in just my briefs. Things are going smooth till she tells me she’s needs to pull my briefs down to have a look at the skin down there.

    I hadn’t groomed in almost a year so when she pulled my briefs down out flopped my hairy dick! My very hairy dick. Quickly she noticed I’m uncut and asked if I ever had any foreskin issues or infections.

    as soon as she touched my dick it got erected instantly. I was super embarrassed and quickly apologized. She said it’s nothing to worry about and she retracted my foreskin to look inside it.

    As she’s got my skin held back she tells her nurse to make a note that the patient is uncircumcised with healthy foreskin and no issues with the glans

    My hard dick still in her hand she let it go and I pushed my skin back over the head. She said oh sorry forgot to do that.

    Then my skin check was done. She pulled my briefs back up and talked about what she saw them told me I could get dressed

    But my dick was so hard that I was having trouble getting dressed

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    # 74042 - by Steven / October 16, 2024
    • - Embarrassing Moments -
    Lesbian Female / 25

    Presumptuous And A Liar, My Family Hasn't Yet Accepted Me

    I had dreams, fueled by my teacher, of attending an important school in the Northeast. I was sure I was IV league material. I applied with absolute certainty that I would make it into Princeton or Harvard, my safe school was Columbia. I didn't make it in to any of them. I was rejected. Facing working and living at home after college I had to do something, I couldn't have that happen to me. I applied to a private college and was accepted.

    I embellished my school choice, and was certain of going to law school. I didn't get accepted. Not to any of the law schools I applied for. Out of desperation I applied for and was accepted to a graduate school in The Netherlands.

    By the time I returned I had discovered the other side of me. I had been in a relationship with another woman from Denmark. She insisted in coming with me, and the only way to get a residence visa was for her to marry me. We got married in her home town in Denmark. I did not disclose this to anyone back home. We were friends.

    She got a job in her field, as a physical therapist working for the hospital. I got a job worthy of my non education, as an office manager for a lawyer. He knew from the very beginning that I was married. I had to add my Danish wife to my insurance. He just didn't think it was up to him to keep my secret. He openly said it. He told me that my mistake was hiding my lesbian persona. It was a disaster with my parents, with many of my friends. I got caught, out in the open.

    It didn't take very long for my noneducation to come to light and my two year fun school in The Netherlands. I went there for a graduate degree and came home with a lesbian. I am navigating my new found persona, the liar and cheat and behind their back behavior. My parents have not forgiven me, and many of my friends have moved on with their lives and careers. My 'wife' comes from a modest home, and her expectations can best be described as a work ethic. Having the US opportunity is most important, even if it is with a liar and a cheat. From her I feel disappointment, I am not who I told her I was. My grandfather told me to quit digging, I am already in the hole so deep I can't imagine getting out of it.

    I am allowed to bring my wife with me, but to be true to my situation, my family is not open about homosexuals. If I were their son and not a daughter, I would be banished and disinherited. I am allowed to refer to my wife as my 'new sister'. A euphemism for lesbian.

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    # 74019 - by Mandy / October 14, 2024
    - Embarrassing Moments -
    Transsexual Male / 26

    Chosen To Be A Sex Slave

    I finally let him do it. After months of harassing me, he finally belittled me enough to the point where my blood began to rush with humiliation as he pulled my pants down, grabbing my dick like it was his, then working his finger into my butthole. Next thing I knew I was bent over my couch, and he was pumping in and out of my ass. I was moaning so hard it was so embarassing. I felt like a slut, the ones you see in porn that just suddenly turn into willing fuck toys that just let the guy do whatever to them, as if I was asking for all this. I was so hot with the shame. He wrapped his arm around my neck still fucking me, pulling me closer to him arching my back. I came so hard I was about to faint, until his own load rushed deep inside me. So much cum it was endless, flooding my insides.
    He loosened his grip on me as his cock popped out of my hole. He just stared at me with this smirk. I didn't know what to say or do, I just laid there trembling, with this strange delight. I felt used, and I never felt so satisfied. All my responsibilities of being a man in society was stripped away from me that day. And if I wanted to keep enjoying this strange new feeling, all I had to do from then on was be total fucking cockslut.

    1
    # 73981 - by Samantha / October 13, 2024
    • - Embarrassing Moments -
    Straight Male / 31

    Embarrassing Moment, A Blessing In Disguise

    I was 15 and my sister was 17. She was having her friend Charity over for the weekend. I had a huge crush on Charity, she was kind of a dork, had glasses, dressed out of style, but my god she had some big knockers attached to her little body. They were almost cartoonish compared to the rest of her. I got home about noon Saturday and they were sunbathing in the back yard. I nearly busted a nut when I walked past the sliding glass door. I made my way out and tried to talk to her, as I always did, but my sister was quick to shoo me away.

    I couldn't contain it, so I went into my room to relieve the pressure. My sister, being a typical evil big sister must've known exactly what my plans were. I was just a few minutes into flogging my log when they burst into my room and threw a water balloon at me. I'm sitting there dick in hand, soaking wet, and dying of embarrassment from the girl I had a crush on seeing me jacking off. I cleaned up and left with my sister berating me by calling me a pervert and loser as I walked out.

    I came home about midnight and quietly made my way to my room trying not to be noticed. It didn't work and in a matter of seconds my sister was in my room saying she was going to tell mom what I was doing, and again calling me pervert and a loser. Charity was trying to deescalate the situation telling her they should just go back to her room leave me alone.

    Then about 2 am I got a text from an unknown number apologizing and hoping I'd forgive her. I sprang out of bed with excitement when I realized it was Charity was texting me. We texted back and for for about an hour, then through the entire next day. The next night she came to my room and we quickly for after it. I was so eager to get those tits out, and they did not disappoint! They were each bigger than my head and left them both covered in hickies. We didn't fuck that night, we just made out and I licked and sucked all over her body. The next time she stayed the night, about 2 weeks after that I got her on my cock. She had the tightest little bare pussy and it was made so much better with those big tits slapping up and down.
    My sister being livid about my fucking her big tit best friend made the pussy that Mich better also.

    1
    # 73969 - by Rod / October 11, 2024
    - Embarrassing Moments -
    Straight Male / 25

    She Is A Keeper

    I have been dating this good looking Mexican chic named Dolores. Big hips nice ass big tits really pretty face long dark strait hair. To be honest i have had a thing for Alison Tylor so almost every girl I have dated seems to look like her. If you don’t know who she is look her up. Dolores is the same age as I am has the look height hair and body type. We where heading to the last Oakland As home game ever the next morning and a bunch of us where going. We took the day off she was spending the night but so were a few friends as well. Dolores and I started to mess around we lost track of time. She hopped on me and started to ride me her top was off and her tits Ds where bouncing around as she grinded away. I was about to blow my load I felt her legs start to tremble and she grinned harder and faster when 2 of my buddies walked in from the garage. I was going to stop and she kept going I shot my nut and Dolores moaned as she bounced and continued to grind away and cum as my 2 friends stood and watched. I told her hey so and so are here and can see you. Out loud she says they can wait I’m cumming. By now my 2 buddies are clapping and cheering her on. She kissed me and stayed on top of me in her thong her tits out big ass out cock in her she wants to kiss. I’m getting hard again she feels this sits up and says let’s go to the room. Almost naked she gets up drags me to the room and we fuck for a while longer. A little later we came down and again my 2 buddies cheer and clap. This time she is a little more embarrassed I gave her a kiss and we all headed to grab some dinner. One of my buddies at dinner leans over and asks me if when I’m tired of her would it be cool if he got her next. I laughed and told him I don’t know man she checks all the boxes.

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    # 73951 - by Brent / October 11, 2024
    - Embarrassing Moments -
    Straight Female / 31

    Getting The Unvarnished Talk, No Sugar Coating

    My sister and I are less than a year apart. We shared the same bedroom until we left home.

    When we were fifteen and fourteen our mother sat us down for the 'the talk'.

    Face it, you are going to get fucked. It's not nice, but it is not unpleasant. It's all about whether you like the boy enough. You have to be prepared, he has to get you hot enough, to feel you up, to suck you tits. To finger you. Put your finger in your vagina and don't let him until you are wet enough. Some boys want you to suck their dick first. Use lots of saliva. Grab his dick in your hand, and use lots of saliva. The reason you suck his dick is to get him hard enough to fuck you. A limp dick doesn't work as well.

    These are examples of condoms. Condoms are a line of defense, they are not a sexual aid. Sexual aids are for fun when you are alone. Don't get them confused. Condoms are for defense. You defend yourself from some other girls STDs. That's what you are defending yourself against. How do you think he got the STD? That means he fucking some other girl too.

    On the defense side is birth control. You are both on birth control. But don't think for a moment that you cannot get pregnant. Plenty of girls on birth control get pregnant. Because they forget. If you are getting spermed, then you need birth control. Take it. The only reason he is fucking you is to get his sperm in you. Everything else is a convenient diversion. If he is fucking you, he is getting his sperm in you. USE YOUR BIRTH CONTROL. It's playing defense.

    Last but not least. Be selective. Don't choose poorly. A dick in hand is not a dick you want. You have to set the limits and the dick you are willing to have shoot sperm into you. Pick carefully. Choose wisely. In the meantime there are sex aids, like these dildos. Use them.

    We have a very open relationship with our mother. We found out from her that she forgot and got pregnant, twice. Lucky for her my father stuck around. She could easily have been a teen unwed mother.

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    # 73854 - by Liz / October 6, 2024
    - Embarrassing Moments -
    Straight Female / 40

    I'm Ready For My Role, But Where Is The Man To Fulfill His Role On Me?

    I studied voice for college. I finished and got an opportunity for further study in Vienna. It was my first time abroad, and it was quite intimidating. I didn't like the people, they were very strict and standoffish. My professors were very demanding. To me they disliked me and used me as an example for the other students. As soon as my year was over I returned home.

    While I was in Vienna I had a sort of awakening. My life was reserved, my family was reserved. Outward displays of affection were looked down upon and it was duty, duty, duty. In that sense, my family was much like the people I was around in Vienna. I was twenty five when I got back from Vienna. Voice is my passion, but there is no money in it and my aunt convinced me to got to law school. Law school was a lot different, for one I was older and the students were older. I went to law school in NY and lived in a small family owned apartment. I was 'growing' up.

    A man followed me home one evening. I had seen him when I left school. And now he was at my door. He said he had seen me in Vienna when I was over there. He remembered my name. It was freakish and uncomfortable. He was an older man, with a beard and grey hair. He didn't ask if he could come in, he pushed his way in. In Vienna he owned a shop which sold instruments to the music academy. He was in NY looking to buy a very special instrument for his collection. To my recollection it was the very first time in my life where I was behind a locked door with a man. A man I didn't know. A man who had followed me. I was nervous. Things went through my mind. He talked but my mind wasn't there. All by myself I had made up my mind that I would suffer in silence, whatever he did.

    When he reached for my wrist to get my attention I jumped back. In the best Operatic scene I surrendered immediately, fell back onto the bed in the apartment, with 'just don't hurt me' emanating from my lips. My mind raced, I waited, I had visions of being Red Riding Hood and before me was the Wolf. I waited to be torn limb from limb, to be ravished. I was aware that as I lay before him, I had already opened my legs, inviting him, thrusting my hips up with my hand over my forehead. 'Take it all', I cried.

    I heard his gruff voice, telling me to take a hold of myself, what did I think he was going to do. He collected his coat and walked to the door, and left. My r**e was over before it started. I lay on my bed for long while, staring out the window. The man was gone, never to return. I composed myself. I had to wait until I was thirty seven before a man put his hand on me, before a man imposed himself on me, before a man took what he wanted and left me disheveled and walked away. I suffered in silence, as demanded by the Opera. I didn't fight, I didn't resist. Life has never been the same since. I wait at night for a man to come to my door, but a man doesn't come.

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    # 73830 - by Gloria / October 5, 2024
    • - Embarrassing Moments -
    Straight Female / 33

    Secrets Of The Dark Ages And The Fire I Feel For Her

    I have a girl who works with me. She is actually in another department, but our offices are next to each other's. We have lunch together in the lunch room. She's younger by five years. We get along real well. Too well. Because I know her secret.

    I have a boss who had carnal desires for me. His day is complete when he gets his dick inside me. I told her about him, how he comes over to fuck me. I told her about the first time, and he shoved my face shoved into a cushion on the sofa, my butt in the air and his dick in me. When I told her she asked me to clarify, when I had his dick in me, which hole? I said well my vagina, he doesn't do anal. That's when she told me her secret.

    Except it is from the dark ages, when she was young girl. The mother's boyfriend came over, her mother refused him, so he took her instead of her mother. Full penetration. She got pregnant from it, but had a miscarriage. It happened at school and that's how the mother's boyfriend got sent to prison. She told me when he had sex with her, he liked it both ways, he had fucked her little butthole.

    After that we became friends, she talked to me a lot about how he had sex with her when he saw her. I let her talk, not out of some sex crazed curiosity, but because if she talks about it, it becomes normal. I know, talking about my man and how I get fucked helps me deal with it. And I'm a lot older than she was. She told me if she got fucked again, she wanted it to be anal. She wanted a dark man, in a dark suit, in a dark room. She didn't want to see his face. Just fucked anal. I asked her about normal, fucked in the vagina. She's not interested. I have to change her mind, my man isn't what I'm talking about for her, I'm talking about a nice guy for her.

    Since we have become friends like this, she comes to my place, when I know he's not coming. We get under the covers and talk about how it feels, how it felt to her, what her mother said when he was with her, and her mother did after he got off of her. She remembers it like telling about a movie. I hold her with my bosoms. I want her to feel the maternal caring. Our bare skin against each other. I care, like a mother should care about her daughter. Holding her in my bosom makes me feel good, and she says she likes it. She likes to have my face in her bosom, nibbling on her nipples. She likes that, and likes it when I let her kiss me. It's playing with fire, because it is fire, the desire to love her. My man doesn't know anything about this. It's our secret. We've gone further. No man wanted, no penetration. Just kissing and holding.

    I want her to know what it's like for her to have a man who penetrates her vagina. To feel what I feel when my man penetrates me. That's normal, not anal.

    And what we do is a distraction, it isn't normal what we do. It's playing with fire. But I do love her, to hold her close to me like that and show her how much I love her.

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    # 73819 - by Tonya / October 4, 2024
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