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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 —
    Straight Female / 26

    We were all eighth graders and we went to a birthday party at a lake house. After cake and ice cream we went to the dock to talk. I laid my head on my want to be boyfriend's lap. His penis got hard and I rolled my head over it, feeling his dick with my head. When we got up to go inside he was embarrassed to stand up, he had 'wet' his pants. This was all new to me, really new I had no idea what happened. He took his shirttail out and we went up to the house together.

    My 'innocence' was such that at home I told my shocked mother of rolling my head across his erection and how he wet his pants. That brought about my first sex talk, not biology which we got in the seventh grade, sex, a boys erection caused by my stimulation, and as to his wetting his pants I got my first talk about ejaculation, with an introduction to the commonly used words.

    It was many days before I talked to him again.

    #45444 — Comments (0) — Jul 26, 2019 at 3:05 PM — That's Juicy! (5) Remove It.
  • — Embarrassing Moments —
    Straight Female / 44

    Throughout my marriage I always wanted to try and encouraged my husband often, to enter my arsehole during sex. He did take me anally once and I loved it, orgasming multiple times. Yet he hated it and wouldn't ever fuck my rear hole again.

    My husband passed away a little over two years ago.

    Around the middle of March this year, I met and began dating a very sexually active much younger guy. Within a couple of weeks our sex life was amazing and we were having all types of sex, including for me, mind blowing anal sex.
    May rolls along and I'm entertaining my young lover at home. We've already had over two hours of wonderful sex and I've sucked his long thick cock back to life. Naked and sprawled across my coffee table, my young lover thrusts into my arsehole and begins to fuck me really hard.

    Building up to yet another orgasm with his cock pounding me relentlessly, we both saw the living room door open and in walks my twenty year old son. Just as he does, I have an almighty climax and my lover plunges into me once more and cums deep up my arsehole. And all of this was seen only a few feet away by my son, who stood with his mouth agape and struggling to say something.

    When he does say something, he says "So this is what you meant by fucking a MILF". I'm about to begin saying sorry for him finding me that way, when I realise he's not talking to me (MILF).

    Oliver is my sons boyfriend (Yes my sons' gay) and his on off bisexual sex partner just so happens to be the young guy who's cock was sliding out of my arsehole, dripping his cum on our lounge carpet as he did.
    Totally and utterly embarrassed, I tried to make my excuses, but my son tells us both we're "Fucking horrible bastards for cheating on me this way".

    The fact is I had no idea Oliver was his boyfriend and I would never have had sex with him, if I'd known. Having said that, I fully understood when my son had told me in the recent past, just how happy his 'fella' made him feel and how amazing he was in bed.

    My son and I have just begun speaking again. I'm not seeing Oliver anymore, yet I am having sex with a younger man. He's just as keen to fuck my arsehole, and if anything fucks me even harder than Oliver did.

    #45417 — Comments (2) — Jul 24, 2019 at 8:39 AM — That's Juicy! (11) Remove It.
  • — Embarrassing Moments —
    Straight Male / 48

    My wife Maryann and I joined some other couples to play the glory hole game one afternoon. This is a couples game where 4-5 couples play. The husbands or boyfriends stick their cocks through a glory hole. The wives are supposed to find their husbands cock and suck it completely off. I knew right away that whoever started blowing me wasn't Maryann. I believe every woman got it wrong when we played. Maryann is slutty and I'm almost sure she chose the wrong cock on purpose. I get so turned on by the way I see her that we immediately had dynamic sex. Just thinking about how slutty she is makes me fuck so very good. I love how I'm so much better with her than I am with a conservative girl. I blew more cum in her and got her off than I normally do in spite of me just getting a blowjob from the unknown wife.

    #45396 — Comments (5) — Jul 22, 2019 at 4:20 PM — That's Juicy! (9) Remove It.
  • — Embarrassing Moments —
    Straight Male / 18

    When I was 16 I snuck into an Adult Theater. I went to the theater to watch the porn, jerk off and hopefully a woman or couple would show up. I was wrong. An older guy sat next to me and started jerking off. He grabbed my hand and put it on his cock. I was kinda into it at the moment. He quided my head down, and I started to suck him off. At this point I was still into it. Then some one pulled down my shorts. I tried to stand up, but a couple of of other guys held me down. So now I'm sucking one cock, getting hit in the head with two or three more, and having one forced in my ass.

    For the next couple of hours I guess about 20 different guys sodomized me, and a lot of others were cumming on my back and head. As soon as one would blow his load in me, another would go in behind him. Eventually I was taking 2 dicks in the ass at a time. It was so painful.

    I could barely walk when they let me go. They gave me my cum soaked clothes and pushed me out the door. I saw blood and cum running down my leg .
    I went to the hospital where I find out that my entire anus was perforated, and detached from my intestines. My asshloe was literally torn to shreds. Now I have a colostomy bag, and a gaping asshole for the rest of my life.
    Stupid naive me.

    #45345 — Comments (1) — Jul 18, 2019 at 1:30 PM — That's Juicy! (10) Remove It. ( * )
  • — Embarrassing Moments —
    Straight Female / 26

    My girl friend and I got caught by four teenaged boys in a sport complex shower we used to go too. We were both standing bare ass naked in open stole shower when we saw them sitting on the bench looking at us. When we found out our towels and bags were gone, we knew they walked in for a cheap thrill. I remember them laughing and making comments about our tits and pussies whiel pointing their cel phones at us. There was nothing we could do but stand there spread out in front of them getting touched and fingered. It was that or being left stranded naked brain storming about how we were going to get home. I remember thinking it was better to get fingered rather than shouting out the door for help and save ourselves from public humiliation. I think giving us our clothes back was a way to get off easy. Smart because we both weren't about to tell our story.

    #45340 — Comments (1) — Jul 18, 2019 at 8:19 AM — That's Juicy! (7) Remove It.
  • — Embarrassing Moments —
    Bi-Sexual Female / 21

    A few years back when I was living with my mom and step-dad an embarrassing moment happened. My good friend Becky and I was wanking my little brother on the sofa. We was bored and thought it was kinky cool thing to do. My step-dad came home real early from work and caught us. My little brother scooted out of the house quickly. "What in the world was going on girls!" he yelled out. "Especially you Sarah, you was performing an immoral act on your brother!" He said when mom comes home he was going to tell her about me. He went to take a shower as usual when he gets home from work.

    We didn't know what to do. Becky was afraid she would be banned from seeing me at my house and I was afraid I would be grounded for a long time and really get hell from mom. We figured we offer a hand job to my step-dad to keep this quiet. We went into the bedroom where he was putting clean clothes on. "What do you want?" he said to me. I told him what if I and Becky stroke him, will he keep quiet about what he saw to mom. "Are you nuts, no way! he answered. I didn't know what possessed me but I removed my top and Becky's top. He stared at our breasts. "That's not enough to keep me quiet." Then Becky blurted out, "What if Sarah and I put a show on for you?" "What kind of show?" he asked. Becky told him girl to girl play and I nodded. "Alright, but a real good one." he answered.

    Becky and I undressed as he looked at my fuzzy snatch and Becky's smooth slit. We started to kiss and fondle each other. I went down and started licking Becky's slit. My step-dad lowered his pants and was stroking a good size dick that I didn't know he had. Becky was eating me while I was laying on the bed. My step-dad took off his pants and offered it to my face. I grabbed it and started wanking it. "Suck it, suck it good, don't stroke it!" he yelled. While I was giving him a blow job, He told Becky to sit on his face and started on her kitty. I stopped giving him head and wanted to try his dick in me. I had to slowly and carefully lower my self on that shaft, while Becky facing me, watched me take it in me. Becky and I started fondling each other tits as I slowly started bouncing on the shaft. He told me he was about to explode and for us girls to lay close side by side to each other with our legs spread slightly. We watched his junk shoot out onto our kitty.

    I knew then that my step-dad was putty in my hand. He couldn't say anything to mom because I threatened him that I would tell her what he has done. For a period of time there, Becky and I would wear a strap-on and bang him with it saying abusive things to him.

    #45339 — Comments (1) — Jul 18, 2019 at 8:09 AM — That's Juicy! (10) Remove It.
  • — Embarrassing Moments —
    Straight Male / 55

    Have you ever had a moment that you REALLY wanted things to go right , and it didn't ?

    Well , it happened to me . I've been doing on-line dating for years now . Maybe I like the mystery , not knowing what will happen on any date . This story is about my most embarrassing date .

    Some dating websites will offer a free messaging to others and you don't need to be a paying member . I took advantage of it a few times . The only problem with it , that most free messaging are only at late nite hours ( like : 10pm - 3am ) and one nite only . So , I came up with ( I thought ) the perfect plan to get the word out to others that I'm available . Just send them a quick and simple message : My phone number is xxx-xxx-xxxx , and email address is [email protected]@@@@@@@@@@@@@@@xxxxx.**m , and move on to the next one . I was typing like " The FLASH " . All I had to do was wait and see who would respond , I kept checking my phone for any missed calls .

    Then one took a chance and text me , BINGO . We chatted for a few days , then she wanted to take it to the next level . We planned to meet on one Friday evening , the date from sexual-hell .

    I've always let the women pick and choose as to how they want to meet . She chose 8pm at the local Starbucks . I was there a bit early ( as I always do , I hate being late...for anything ) . But she didn't seem to care about being on-time for any dates . I sat in the truck and waited...and waited ...and waited . Nearly an hour later , she texts me that she'll be there soon . It was already passed 9pm when she finally drove up ( not a good start ) . I brought flowers and offered them to her , as she quickly jumped into my truck ( she was already acting like she was in a hurry to get this over with ) .

    We did the usual " 50 Questions " game . But , I started to lose focus as I noticed her huge rack ( my bad ) . Trying to behave like a true gentleman and not stare at her big boobs , I suddenly said " damn , I really want to kiss you " . She didn't hesitate and lean towards me and joined in a full-mouth kiss . As soon as her juggs touched my chest , I lost it . I just had to cop a feel and she knew it . " you want to kiss them too " , she said sarcastically . " Sorry , I didn't mean to..." I tried to apologize for my staring . " It's ok , honey...all the guys want them too " as she lifted her shirt off and exposed the bra-less knockers . And they were HUGE ( guessing about 44ddd's ) , as I enjoyed massaging them . She seemed to enjoy my hands too , as she just let me had my way with them .

    I remembered the guys from high school saying " anything bigger than a mouthful , is a waste " , about women's breasts . But , I never saw it that way , and that's why I got more dates than the rest . I've always enjoyed women with big boobs . As soon as she let me " kiss " one nipple , she planted her hands behind my head and drew my face into her cleavage ( almost smothering me ) . She had to be the most aggressive and horniest woman I ever met .

    When she finally let me up for air , " you want to fuck now ? " she asked . I always try to approach all first dates with the thoughts of " ok , we're not getting any sex now , just meet and greet...keep the subjects away from anything sexual...and hope for another date " . She was already trying to get undress in the passenger seat , and we're still in the Starbucks parking lot . Thank god they was closed for the nite .

    I was stunned a bit as to how this so-called " meet-n-greet " was going . I decided to take advantage of her need to get fucked right now , and started to undress myself . Moving the seat back as far as it will go , I saw that fucking in here was going to be cramped and very uncomfortable . She wasted no time , as soon as I got my pants off and my semi-erection was exposed . She dove down on it , with her mouth wide open ( like a shark that is ready to chomp down on some unsuspecting swimmer ) . Damn , that felt good , as she sucked it till I came in her mouth . Then , it got ugly .

    She tried to get positioned in the seat so I could return the favor and go down on her . My truck didn't have the room , like my " 62 " Cadillac from high school ( the girls love that back seat in my " Cad "...plenty of room for any sexual action ). I just couldn't get in the right ( or any comfortable position ) position to return the favor for her . The best I could do was to finger-fuck her already moist pussy with one hand and massage one boob with my other free hand . She got off from that and squirted her juice all over the seat ( like a whale breaching and blasting water from it's blow-hole ) . " oh yeah , baby...fuck me now " she demanded . But , no matter how I tried ,
    I just couldn't get into that position to accommodate her .

    She finally said " we need to take this outside...maybe in the back " as she pointed to the truck-bed . I just went to the dump that afternoon and I haven't hosed off the dirt from that adventure , so , " oh hell no " I wasn't about to fuck any woman back there in that filth . Then she said " I know a place , where we can get plenty of room " . I thought we might go to her place as she started giving me driving instructions ( as I tried to put my pants back on , in a hurry ) . But she lead me to a nearby park / soccer-field . It was late at nite now , and the park was totally emptied . I parked the truck , and quickly slid out of the truck ( butt-naked ) and motioned her to bring herself and spread her legs on the driver seat . So I could fuck her while standing outside and her pussy close to the open door . That proved to be a bad idea , the truck sat-up too high and I didn't have any running boards to stand on . And to make it more uncomfortable , some high school kids came driving by .

    So , back inside , we both knew that this wasn't going to happen tonite ( as she noticed the time on her cellphone ) . We decided that we want to make this happen with a better choice place ( her home , maybe a motel , get an air-mattress for outdoors in the woods ) as she rambled on a few options . By the time any of you will read this , we already made for another date...wish me good luck...PLEASE .

    #45297 — Comments (0) — Jul 15, 2019 at 11:16 AM — That's Juicy! (2) Remove It.
  • — Embarrassing Moments —
    Straight Female / 18

    I can't wait until I leave for college in 3 weeks! My "friends" are teasing me horribly about having sex at our graduation party last month. Not that I had sex, but who it was with. The guy is kind of a geek,but has always been nice to me.

    When I drink I get very slutty. He was there and I was drinking. He has such a nice cock! I sucked him, then he put a Trojan on and rode me hard, he made me raw! He turned me over and threw his condom, and got me anally. He was a fucking machine!

    After he shot into my butt, he collapsed onto my back. That's when I noticed the bedroom door open and everyone watching and taking pics and vids.

    My friends call me "geek girl" now.

    #45242 — Comments (1) — Jul 11, 2019 at 12:24 PM — That's Juicy! (25) Remove It.
  • — Embarrassing Moments —
    Straight Female / 28

    I grew up in a small town, single mother who worked as the secretary for the School Superintendent. During puberty and for fifteen years later I suffered from Acne. That and very low self esteem. No wonder that I never dated, never got kissed, never got felt up. Except in my dreams. In my dreams I was hot, and fantasized I was the main character of the lovelorn novels I read and devoured.

    I got a certification in elementary education and thanks to my mother's boss I got a job in the school district. I actually started making as much as my mother, enough for me to move into an apartment. I supplemented my income working part time at the Christian bookstore. But now that I was living alone I ordered my first sex toy. So much better than my household inspirations. I also ordered some graphic sex novels. The Princess stolen from her father's tent and ravaged by the outlaw under the desert moon. And with my toy it all came alive.

    I was never fat or skinny, too tall or short, a bit tall at five six, and solid thighs and butt. My boobs were never an item for me, I liked my ass, a woman's ass like the novels said, childbearing ass.

    I went to look at a furnished garage apartment in the nice part of town. The lady was widowed and she liked I was a school teacher and Christian bookstore clerk. I got a reduction in rent, bigger and furnished apartment and I could use her washer and dryer. I looked out my window the first Saturday I was there, the man was mowing the lawn, it was hot and he took off his shirt, I found my trusted toy and stood at the window with my toy up my pussy. I was in dreamland when he pushed the mower past my window and saw me going fast and strong. He just stood there, I came out of my dream standing there with my silicone dick in my pussy.

    We stared at each other for that minute while I pulled my toy dick out and covered myself with my dress, turned and walked into the bedroom and screamed. My embarrassment was so bad that I missed work for a week.

    #45225 — Comments (0) — Jul 10, 2019 at 1:58 PM — That's Juicy! (5) Remove It.
  • — Embarrassing Moments —
    Bi-Sexual Female / 24

    I moved to the big city after college to start my first professional job. The HR office helped me get settled offering me the service of an apartment locator. The 'girl' who took me around showed me several properties, including the property she lived in. Of course she sold me on her property and I rented a one bedroom, my first place.

    She called a couple of weeks later to see how I was doing, I was honest, I hadn't met anyone and the people at work were older and married. I guess I whined and she said I could go with her to her friend's place. When we met in the parking lot she was dressed pretty casual whereas I was dressed up. She gave me the sign to get back upstairs and change. She followed to see how I had fixed up my place. She stepped into my bedroom while I changed, she wasn't supportive of my top and stepped into my closet to find a top.

    Things didn't stop there, she kept me on a leash while we were at her friend's. We played cards and I had to be her partner. She had me serve our plates and she carried them to the table. As the night went on she sat behind me and played with my hair. She combed me and asked the other girls to vote what made me look better. Her kiss on my cheek caught me by surprise. Her friend asked if I was really just this girl she knew or if I was 'this' girl she knew.

    How long had we been dating? I must really like her, I was so together with her. She could feel the love and was jealous. She gave me the lowdown on her love life, where they met, how long ago. She was really happy S had met someone. Back in the car I confronted her, sure she was gay, wasn't I? NO I wasn't.

    But life isn't fair, she had told her friends I was the catch she had been praying for and she wasn't going to just walk away. She invited me in, come sleep with her. I tried to say no, so she just stayed with me, went through my dresser found a night shirt and said she had never felt so good. My rejection went in one ear out the other, just push all those negative thoughts away, if ever two people were meant to be together this was it. Heavy petting, kissing and full body contact took me by surprise and I had my first intense girl on girl experience. We just spend all our not at work time together, day and night. Not where I ever imagined myself, being in an all girl relationship.

    #45207 — Comments (0) — Jul 9, 2019 at 5:27 PM — That's Juicy! (1) Remove It.
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