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Adult Confessions | Embarrassing-moments |
Embarrassing Moments
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 section of AdultConfessions.com is here just to chronicle those most embarrassing moments. Let the whole world know your bad habits, and when you got caught committing them.
  • — Embarrassing Moments —
    Transsexual Female / 25

    I was a normal guy when married my wife. I think?

    After a month of talking me into being a good cuckold "girl" I agreed to try it. She called me a good girl and told me to call my best and tell him to, "come over and make my wife feel what a real man can do to her".

    I was given a sexy lingerie with stockings and garter belt and high heels. When he rang the doorbell my wife said, "Ok slut go let him in". I opened the door and he said, "You weren't kidding about him wearing sexy things".

    I said, "When did you two talk about this"? My wife looked at me and lifted my lingerie and she said, "I told you he has a super small penis". Then she opened his pants and out popped 8 big inches of soft cock.

    My best friend grabbed me and he is much bigger and stronger than me. He said, "Your lovely wife promised that you want to suck my cock to get it hard but I know that you really want to taste my cum".

    I was just taking his big cock in my mouth and he told me that my wife has always been very tight for me. My wife laughed and said, "Well that is why you never felt my pussy because after our "sex" John was the man of our life.

    I was trying not to gag but first my wife pushing my head down and saying, "That's a good girl gag on your new Love's cock. We decided yesterday that you will dress and be our sex princess but you only get John"

    She told me to tell him how much you love his big cock. I did my best to say it but she and John were pushing my head down. John told my wife he was about to cum and should they warn the SLUT? Me, and she said no she needs to get used to it like the pretty girl she is.

    My mouth filled with a wonderful warm sticky salty sweet cum. I tried to swallow but my mouth full he shot my face too.

    I decided right then that I was not making any mistakes and with sperm all over my face I smiled and said, "I am so happy to be a good girl for you and be the beta female to the real girl".

    Only married for 29 days and I am so lucky to have been nudged into my true calling, my penis is extremely small and my wife is the only female I have ever been with. In the nine months of dating and one married we had sex 3 times. John kept her happy. She told me that we were having more sex than normal.

    My first 30 days as a girl I did all housework and was learning to cook. Plus 2 or more blowjobs and/or sex a day. I was happy. My wife gets 3 or more times a day, lucky girl I am so jealous.

    Within 30 days of my change my breasts got sore and began to grow. My wife said she started me on testosterone blockers 6 months before the wedding and estrogen 1 month before. She giggled and said, "You are just a much better person this way. I agree.

    I hugged her and thanked her over and over for giving me this wonderful opportunity to see my feminine side. She said she thought I would be mad. I asked, "How could anyone get mad at becoming a girl, it is the best thing in the world to be a girl".

    I am a little scared today I am being introduced to a man who can make me his girlfriend. I have heard rumors that he buys girls for sex slaves or turn me into a prostitute. I don't know if it's true but my wife said, "You will be a great little whore girl". I am dressed like a slut without panties to show off how much the estrogen shrunk my already small penis and testicles the size of small raisins.

    He is here I will finish soon.

    Well he said he likes me and grabbed my ass and boob and asked if I wanted to be a prostitute and get lots of sex. I said if he would protect me. I was tried out to make sure I am Good with cock. My wife said, "She is good with cock. In 10 months I only let her try to be a man 3 times then after one month married she was in lingerie and taking big cock.

    He pulled out a huge vibrator almost 2 feet and very thick. I was sucking him and my wife took the vibrator turned it on high and pushed it hard and deep into my ass. She was encouraging me to suck more. Then my new pimp said, "Push it in as deep as you can so I know how much makes her cry". She said that it will hurt but you can take a lot.

    It felt like the whole thing but I only took 14 inches before crying like a girl. He said that was great but next week i would take 17 - 19 inches.

    I am being called to go with him. My wife said that she needs me to sign papers so her and John can get married and I am free to marry a man too. I am lucky to have been turned into a girl and discover how wonderful big hard cock is and how delicious sperm is. My tiny penis is not able to get hard at all, so lucky.

    #37681 — Comments (0) — Oct 25, 2017 at 9:01 PM — That's Juicy! (2) Remove This.
  • — Embarrassing Moments —
    Bi-Sexual Female / 19

    So at my last physical, my doctor said he needed to check my sexual responses and asked me to masturbate so he could check my arousal, and ideally orgasm. I was kind of clumsy at it so after a few minutes of staring at my vagina, he just asked if I'd like him to do it, or if I would prefer a nurse or something.. I didn't want to involve any additional people as it was embarrassing enough, so I said he could do it. He took off his rubber glove and fingered me for a few minutes, which is all it took to have an orgasm. He really really knew what he was doing, it was so gentle and smooth but right to the point. He seemed totally dispassionate and professional. Then he just looked inside a bit, pulled the hood back on my clitoris, and went on with the exam.
    Is this a normal part of teen girls' exams or was this doctor extra thorough?

    #37674 — Comments (7) — Oct 25, 2017 at 11:38 AM — That's Juicy! (8) Remove This.
  • — Embarrassing Moments —
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    #37665 — Comments (0) — Oct 24, 2017 at 9:58 PM — That's Juicy! (0) Remove This. ( **** )
  • — Embarrassing Moments —
    Transsexual Female / 23

    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.

    #37654 — Comments (2) — Oct 24, 2017 at 12:38 AM — That's Juicy! (2) Remove This.
  • — Embarrassing Moments —
    Straight Male / 53

    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.

    #37639 — Comments (3) — Oct 23, 2017 at 10:27 AM — That's Juicy! (5) Remove This.
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    #37575 — Comments (0) — Oct 19, 2017 at 1:20 PM — That's Juicy! (0) Remove This. ( *** )
  • — Embarrassing Moments —
    Bi-Sexual Male / 25

    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 couldnât 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 didnât 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 wouldnât 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 couldnât 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 Iâm 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 donât worry nurses see it all, itâs no big deal. She proceeded to say as long as you feel good then Iâm happy.

    Never saw that nurse after that

    #37558 — Comments (0) — Oct 18, 2017 at 11:12 AM — That's Juicy! (3) Remove This.
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    #37544 — Comments (0) — Oct 17, 2017 at 4:02 PM — That's Juicy! (0) Remove This. ( **** )
  • — Embarrassing Moments —
    Straight Female / 25


    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.

    #37530 — Comments (1) — Oct 16, 2017 at 5:30 PM — That's Juicy! (4) Remove This.
  • — Embarrassing Moments —
    Straight Female / 38

    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.

    #37506 — Comments (0) — Oct 15, 2017 at 10:17 AM — That's Juicy! (2) Remove This.
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