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 am a transgender woman. I was 5 when I saw the doctor for it the first time.

I was put on testosterone blockers and estrogen at the right time before I became masculine.

I am a small framed woman with less muscle than lots of women. Their is sometimes a negative outcome, like me.

I went to see a doctor about my sex change operation and I was given terrible news. He said, "I'm very sorry but your penis is too short to be made into a clitoris".

I cried and begged for his help. He said that he was sorry and would watch in medical trade magazines for any new ways that would help me.

I hope they can get something that can be put on my clitoris to make it work. I want to be a woman without a penis even one so small. At least I don't get called sir or he, I am only called female things. Still I don't want to have a penis unless it is on my man.

It is so hard to pee when I sit down and have to push it down and hold it. If it gets away from me my panties or pantyhose get pee on them and sometimes on my dress or skirt. My mother always said that I was such a lucky one to have such a small penis. I think it is too big.

I need to calm down so I am going to call a few men and see if I can get a nice gangbang together. They all know that I will cook for them and they all love my cooking.

Ok I am back from calling 6 men but only 4 can make it. They all know that other men will be here too and that I am the only girl. I made a Lasagna and right before we start the fun I will put it in the oven

In about a half hour I will have a cock in my mouth and ass and one in each hand.

I just got a call from one of the men asking if his friend comes. I said, "The cocks the more fun for me".

Ok 3 guys are here now and want to massage me to loosen me up.

I melt when a man massages me. Ok my SEXY MEN need a woman's touch so I must go be a great hostess.

Thank you God for making men so sexy.

  • I don't know if this is embarrass or gross. My wife of 50 years of marriage slowly telling me she doesn't want oral sex. I can't seem to get over it I been giving her oral sex all these years. She know is my favorite thing to do to her. I'm thinking is she getting oral sex from someone or maybe the neighbor.

    I want to find out so one day I setup hidden camera in the bedroom. Lord and behold what I discovered. She was playing with herself with our toys. We have assortment of vibrator dildos. When she about to cum, she squirted a full stream of pee all over the bed. I can see it, is strong and shooting up in the air. I have never seem her do that and she is keeping a secret from me.

    I finally confronted her about it. First she was so piss off that I spy on her. After she had calm down, she was so embarrass about peeing when she came. She didn't want to pee in my mouth when I give her oral sex. I told her is okay is kind of kinky sex. She then told me you are gross.

    I kept bugging her about giving her oral sex and wants to try it at least once in my lifetime. She agree and told me to be ready when she does it. It will just squirt out and she can't control it. She was right, it was all over my face, mouth and nose. I got so excited I kept licking her pussy and sucking on her clit. She was moaning so loud and intense, trying to push me away. I held her legs tight with my mouth push against her pussy just kept on licking and sucking. She finally said that is enough and I stop.

    I got up clean off my face then I fuck her. I told her I want to do this again I didn't care if she pee on me. She said I hope you don't get sick from my pee. I said if I do so what, you only live once.


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    This happened when I was 17. I was in the hospital for around two weeks getting tests done and had surgery. Well being at that age every guy know how often a teen can masturbate.


    It had been a week since I blew a load so I was way over due. I couldn't handle it anymore and I had blue balls so bad!

    I wait till the third shift nurses were working since it was a middle aged woman and I knew she didn't come in every minute to check on me. She shit the door for me since I liked it shut at night and I knew I had some privacy now. Well I thought so.

    I grabbed the napkins on my tray I had, pull my blanket down far enough to expose my crotch and pulled my gown up. They had pulled my catheter out 3 days prior so I was dying to jerk off. I raised my bed up, and was stroking away and boy it felt good. I knew I wouldn't last long so I stroked it and I started blowing my load al, over my stomach and in walks the nurse. She sees me masturbating and cumming, of course I couldn't stop and she walks back out saying sorry. Boy was i embarrassed. There I am, 17 jerking my dick and a nurse in her 40s catches me.

    I wiped up the cum the best I could with the paper napkins and tossed them in the garbage can next to my bed. About 10 minutes later the nurse comes back. She asks if everything is alright and if I'm feeling okay. I said yes. She proceeded to go into the bathroom, got me a warm wet wash cloth and a dry towel and said this is for you to clean up. That made me turn red! She left, I wiped up my stomach better than what the paper napkins could do and dried off.

    She came in later that night and I was still so embarrassed I said sorry you saw that. She just said don't worry nurses see it all, it's no big deal. She proceeded to say as long as you feel good then I'm happy.

    Never saw that nurse after that


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    I should've been smarter. I was 17 and hanging out with a 40 year old man. He was a close friend of the family for years. One day I just started going over and hanging out at his house. We watched movies and had meals together. He never tried anything.
    And then I turned 18. Game changer. He would tell me now that I'm a woman I can just wear a night shirt when we're alone.
    It took a little convincing but eventually I started just roaming around in one of his shirts. It started with a kiss. Then a touch.
    Watching movies became a challenge cuz his fingers were always in my underwear and I wasn't ready for sex. He would tell me good girl when i listened to him. After a month he got fed up and yelled at me to take off the panties. I was kinda freaked out and did as I was told.
    From there he got more rough. He would hold my legs open, tell me to relax and it got to the point where he took me over his knee and slapped my ass if I didn't obey.
    After enough slaps to my tender ass I just started giving in. In one day I lost my virginity and learned what a blow job and sex was. Including anal.
    I was just a toy. His friends would stop by but I wasn't allowed to put on anything other than a shirt. And if he wanted to touch me while they were there I couldn't say no. If I did I would be punished in front of them.
    I had to keep the house clean and always be ready for sex, and punishment.
    After about 6 months he got bored with me and told me I had to go. I was heartbroken. I thought I was in love.
    I still have nightmares.

    I suppose that this was wrong, but at the time it was right. I grew up in a close latino family, in an all latino neighborhood. We lived with our grandmother, my mother and I, and she and I shared a room and a bed. When my mother had a 'friend', I had to go sleep with my grandmother.

    On one of those nights, my mother was going at it pretty loud, and her guy was calling her all kind of bad names, we could here him slapping her and telling her to do things, and her telling him that she liked getting fucked and for him to stop hitting her and fuck her.

    My grandmother had me held tight against her, she kept saying things like 'this time she is really going to get it', 'I bet he has a huge cock', 'she likes a man that knows how to treat her', she was humping herself against me and feeling herself and fingering herself and she went into this orgasm and when she was done she said she wished that she had a man that would fuck her too.

    I was 12. That man became a fixture in our house and I had to sleep with my grandmother and my mother got it most of the time. She told me that he didn't slap her face, he slapped her ass, he liked to slap her and that is how she got hot and once she was hot she had to have him. She reminded me that men liked women with a nice ass. Tits were nice, but ass was better and a girl with a nice ass and a pretty face could get just about any man she wanted. In my house my mother and grandmother talked about sex all the timed and my grandmother examined me to see how I was growing up.

    My mother's boyfriend liked for me to be affectionate to him. To put my arms around his waist, to hold his hand, to sit on his lap, to hug up close so he could feel my tits against his chest. He would have me put my arms around him, hug up real tight so he could feel my tits and he would hold me by my butt and tell me that I was growing up and soon he would show me what a man was. We had a large couch, the only real piece of furniture in the living room, and I would straddle him and sit on his hard cock and rub myself until I had an orgasm. A lot of times he would cum in his pants and show me what I had done. I was horny all the time.

    On my 14th birthday, after we ate he had me stand beside him and he pulled my pants out to look if I was grown up. I lowered my pants and panties halfway down my thighs and he felt me up asking me if I was ready to be with a man. he stood up and told me to take my pants off and we would go find out if I liked it. I took my top off and totally naked I lay back on my mother's bed and I had my first complete man experience.

    My mother pretty much told me to find my own man, but to find one that worked because if not I was going to have to work to support him. The man I found was the owner of the home repair shop, he was in his forties, his wife didn't live with him and I became his girlfriend.

    Later, many years later, when I got out of the army I went to cosmetology school to learn how to be hairdresser, I owned my own shop in the neighborhood. My old boyfriend when I was a kid is an old man and I take care of him. My mother is the grandmother, I live with a man and she lives with us, we have a three bedroom house so my daughters have a room to themselves. I'm sure that my mother and daughters can hear everything that goes on at night, my man likes me to be affectionate to him, and I am not quiet.

    I was with my girlfriend visiting her parents in Texas. The own a nice big ranch there and we stayed a week with them. That was the first time I meet them in person. Surprisingly they let me sleep with her in her bedroom. At first I was like I'll sleep in the guest room to be polite but they said don't worry we're not that strict.

    During the dad when her dad was at work I'd get some of his work done around the property and help him in the evening. I seemed to get along great with them.

    My girlfriend told me before we went down there we weren't going to have sex at her parents house. As much as I wanted sex I was like okay I can respect that. But on the fourth night there I couldn't last much longer, I needed sex. That evening after eating dinner we were back in her room and I told her I need pussy, ass or a blowjob bad. She said I do t know about any of that. Finally I said okay I'll just masturbate after everyone goes to sleep.

    So it was around 1 am. I was sure everyone was asleep. I walked down the the bathroom and looked for something I could lube my dick up with. Looking around all I could find was some albolene. So that was gonna have to do.

    I let my pajama pants fall to the floor, push my underwear down around my knees and started beating away. I left the lights off to try to hide that I was in the bathroom at 1 am.

    There was no lock on the door so in walks my girlfriends mom! My dick was in my hand and she noticed. I pulled my underwear up after her seeing me standing there beating off and I was wearing briefs so that didn't hide much. She looked at me and said what are you doing! I was like reliving myself. She said don't use the hand towel for that either! Use the toilet when you cum. I about shit she told me that. She shut the door and I finished.

    The next night my girlfriend tells me her mom told her she saw me jerking in the bathroom. My girlfriend thought it was funny. Her mom said I had a nice uncut cock and thought it was cute I shaved for her! I was embarrassed though. Finally that night my girlfriend had sex with me!

    Last month, still no knowing what caused it, I had food poison while visiting my uncle in New Jersey. I was so sick I couldn't even hold water down, couldn't control my bowels or bladder. My uncles wife Laura and their daughter Vanessa took care of me for 4 days. I was so sick at the time the embarrassment of it all didn't bother me until I started to feel better. They both undressed me many times and cleaned up the humiliating mess I made. There were three times they actually put me in the shower just to clean the vomit and poop off of me. It was bad enough that Laura saw me naked so much but Vanessa is only about 25 and she also took care of me as much as her mother did. I can't think of anything more humiliating as those four days. I haven't seen them since then and am not looking forward to the next time I do.