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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 Male / 24

Performance Issues

Something happened six months ago that has changed my life. I used to be a normal 24 year old straight guy. Now I don't know.
I spent 45 days in jail for bad checks. It didn't go well. I had a choice. Get my ass kicked all the time or perform sexual favors. Two guys in my section promised to keep me close and safe if I serviced them. I started giving them blowjobs but soon it wasn't enough.
The first night it happened I was face down in a bunk with another man shoving his cock in my ass. It hurt but he didn't care. He fucked me hard. Besides the pain in my burning asshole I started to feel something. I realized my own cock was rock hard and digging into the mattress. Afterward I was so embarrassed. Not at getting fucked in the ass but at the thought I enjoyed it. Getting fucked became a near daily thing. And most of the time my cock got hard, a couple of times I even came myself without touching my cock.
After I got out things got worse. I constantly wonder if I am gay. I have a girlfriend but for the past several months I have only been able to have sex with her two times. My cock will not stay hard when I try to fuck her. It has only made my shame worse. And enforced my thoughts about being gay.
What should I do???

5
# 69659 - by Confused / January 18, 2024
    • - Embarrassing Moments -
    Straight Male / 28

    My Reputation

    Next weekend is my high school 10 yr reunion. But I am too embarrassed to go. I can't even tell my wife why because she doesn't know anything about my teen years.
    I guess it all started when I was 13 because I had just started middle school. My best friend was staying over. Late that night when we were in bed we started elbowing each other and that turned into wrestling on the bed. At one point he was on top and I was on my back. Our crotches were rubbing together. We both realized we were getting hard. After some touching he rolled over on his back and pulled his shorts down a bit. I reached over and stroked his cock until he came all over my hand. I immediately grabbed my own cock and jacked off. The next weekend he again stayed over. This time I stoked him a little then put my mouth on his cock. I only sucked for a few seconds when he filled my mouth with cum. I didn't know what to do, I managed to swallow most of it.
    Now here is where the problem comes in... The next weekend for some reason there was a gang of neighborhood boys including my best friend hanging around on Saturday. My friend had planned on spending the night so we could play but 3 other boys asked my mom if they could sleep over. It was then I realized my friend had told them what I did. I was scared to death. I kept quiet and tried to avoid everyone all evening, but finally my mom went to bed. My friend and the other 3 boys started looking at me like they "expected" something. We were in the living room in the open and there was no way. Finally I whispered in my friends ear and asked what he told them. He admitted it and said they wanted sucked too. He kept elbowing me and saying we should go to my room. Finally I got up and said "OK, lets go". We all went to the bedroom and shut the door. I got on the bed and just sat there as all the boys stood there looking at me. Finally my friend went first. He took off his shorts and got on the bed. I leaned over in his lap and started sucking his cock. He didn't last long. From there the other boys were ready. One by one they got on the bed and I sucked each one of them off.
    At school I quickly realized word had spread even further. I got invited to sleepovers by many boys. Also boys were asking if they could come over to my house.
    Thats how it started. From there and all through high school I was known and the "blowjob boy".

    1
    # 69651 - by BiBoy / January 18, 2024
    - Embarrassing Moments -
    Straight Male / 48

    Too Small

    I wish I was bigger, I am so small, there must be something I can do No women want me

    9
    # 69538 - by Smalluk / January 9, 2024
    • - Embarrassing Moments -
    Straight Female / 36

    My Dildo And The Workmen

    Enjoying myself with my favourite suction cup dildo (I have four) in our kitchen, I looked up to see two workmen looking through our patio windows.
    I'd clean forgotten about them starting some work in our back garden. And I'd just sank anally all the way to the base while playing with my clit.

    Obviously my husband wasn't at home and I was completely naked.
    They saw everything and watched as I lifted off the dildo. But the large dildo had been sliding in and out of my pussy and arse for ten minutes by then and I couldn't stop myself from orgasming.
    I looked at them with my whole body convulsing and couldn't help myself from crying out with utter joy.
    When I settled down, with them both still staring at me, I stood up and brazened it out.

    Walking to the patio doors, I told them I'd be with them shortly and walked as calmly as I could back through the kitchen and upstairs utterly embarrassed.
    To this day my husband knows nothing about any of it, but I still see one of the builders every now and then. He never says anything directly, but he winks in that 'I'd love to be your dildo' way.

    0
    # 69478 - by Julia / January 6, 2024
    - Embarrassing Moments -
    Straight Female / 33

    Men Are Pigs Sometimes

    I had been dating my boyfriend for about a year when we decided to part ways. We had a situation…

    We are fucking on his couch one night and three men walk into the room. I am naked, tits hanging out, with my ass in the air. I was embarrassed and I told my boyfriend to stop and let me go to another room. He told me he couldn’t do that. I asked why and he said he owed these three men some money and i was payment. His dad and two friends…

    I was outnumbered so I let it happen. These men used me like a piece of meat, like a whore, for their pleasure. By the time it was finished, I could not walk, I could not talk and my c**t was beaten down. My boyfriend could only apologize. The other men said I should leave him as this is what he agreed to allow to happen to me. I did…on the spot. I went home an never saw these men again.

    5
    # 69455 - by Lauren / January 5, 2024
    • - Embarrassing Moments -
    Straight Male / 53

    Curious No Longer Straight Moment

    What I thought was just a typical day turned out quite differently I was watching some porn and masterbating alone at my house not thinking I would be interupted as it turned out my buddy dropped by to visit my door was unlocked which is not unusual he just came on in little did I know he was there I guess he caught a glimpse of me lying on the bed jacking off and decided to have a little fun and catch me when I started to shoot my load he walked in on me while I was still cumming I got a bit on my hand and was just licking it off as he entered my room talk about being embarassed! He said what havewe here lol I said well thought I would see what it tasted like not bad I joked he said yeah I have often wondered that myself and to my surprise he said do you mind as he dipped his finger into my cum pooled on my stomach and proceeded to taste it hey pretty good let me know next time you unload I would love to taste it straight from your cock what do you think I said sure maybe later today hows that sound Perfect! he said now what is your thought about getting cum right from the source well I never really thought about it but I must admit it certainly has my attention now I chuckled and at that moment something cameover me I couldnt understand I really wanted to take his cock into my mouth and just have my way with it he was only to eager to oblige next thing I know I have my lips wrapped tightly around this 8 inch very thick veiny cock I had no control of my actions I bobbed my head up and down that shaft and sucked and twirled my tongue all over his pulsing twitching cock until I felt a sudden gush of thick white cum hitting the back of my throat sawllowing as much as I could the rest I swished arond in my mouth savouring the taste of his sweet cum now what I thought was a typical day turn out to be the day I discovered I love tasting cum and cock as well so a new begining for me .More please

    0
    # 69447 - by Cummeo / January 5, 2024
    - Embarrassing Moments -
    Straight Male / 20

    Mom Now Has Some Serious Nipples.

    I am a sophomore in college and came home for the holidays. When my Mom met me at the airport, I couldn't believe my eyes. Seems she has been on this makeover kick and was slimmer and very busty. She gave me a big hug and I could feel her large firm boobs pressing against me.

    On the drive home, I complimented her on her new look and I asked her if she'd had some work done. She told me after her divorce from Dad, she'd been working out regularly and had even gotten a boob job.

    So over the course of the next few days, I kept looking at her new boobs as she walked around the house braless. I couldn't believe the difference. Now I had seen my Mom's boobs a few times while living at home but she was altogether different looking now.

    One morning while having my coffee, I went down the hall and she was on the treadmill. She had on a tank top that looked about 2 sizes too small and fit her like a glove. As she was working out, the shirt began to get wet with sweat and her nipples poked out as big as the end of my thumb.

    She saw me staring at her boobs and I spoke up and told her how awesome she looked. She laughed and told me that with the help of modern medicine and $10K she was now a 36DD. I laughed and told her she needed a bigger shirt and it looked like her nipples were gonna pop thru the fabric.

    She laughed and said since having the surgery, her nipples were like permanently erect. She then shut of the treadmill and raised her shirt and showed me her awesome boobs. "See how hard my nipples are now, they're like this all the time" she said as I just stared at her boobs.

    She took my hand and placed it on one of new boobs and said "Feel how firm they are now, what a difference ,huh"? I massaged her boob and then slightly pinched her thumb sized nipple between my fingers. I grinned and said, "Wow Mom, you could be a porn star with these things". She just giggled as she pulled her shirt backdown. I could feel my cock getting hard, Wow.

    A few mornings later she was standing at the kitchen sink and I came up behind her and gave her a hug and couldn't help but run my hands up and cradle her huge boobs in my hand while squeezing her nipples. I could feel my cock getting hard as I pressed against her.

    " You really like these don't you" she teased saying "Most guys do". Before I went back to school, I convinced her to pose for a few topless pics with her face obscured, so I could show the guys what a hot Mom I had. She loved the idea and gladly showed them off for the camera as I played with those big erect nipples.

    10
    # 69406 - by Paulie / January 3, 2024
    - Embarrassing Moments -
    Straight Male / 28

    Holiday Party

    I have been having seeing a woman from my office now for about 2 months. It started shortly after I started. Alyssa is in her late 30s blond short hair blue eyes nice full lips that I use often small perky tits with big nipples and what attracts me the most is her nice thick thighs and her plum ass. Up to a couple of months she did not enjoy anal but has learned that I like it and she accepts it nowadays.
    We spend a lot of time together at work alone so as long as we get out work done we have plenty of down time to use our office for sexual activities. It’s to the point that she asks me what I want her to wear. Some days I like her in leggings and some in skirts. Skirts are a little easier to access but leggings really show off her ass. I am single so am able to order toys online and have them sent to my place. She has a collection of butt plugs that she will wear for me throughout the day and I take pleasure in putting it in and taking it out. She is married with kids and I know this sounds selfish but our sexual chemistry is really good. I have field a good amount of women some married some single older younger and some where close but Alyssa tops them all. She is very well respected in our work industry and is a nymph in our private lives.
    The night of our holiday party our company was hosting it at a large hotel. Most people had gotten a room including my self. Before we left the office I had given Allysa a g*ft. It was a remote control vibrating slim toy that you placed right around the clit and the remote had a few settings of vibration. I put it in place and we tested it on low. She sat looking at me and instantly I could tell be the look on her eyes that it hit her spot. I turned it off and she said that felt great. I kept the remote she kissed me and we agreed to meet later that night. I got to the party and was talking to a few people when I saw them arrive. She made her way over and introduced her husband to me. We talked and he said that I had heard lots about me and the group of people that we worked with in our office. She had gotten him and herself a drink. He put his drink down quickly and went back for another asked if we wanted another I was good as well as his wife. Off he went and on the vibrator went. I took pleasure on the control I had over her. I hit her with the 3rd setting and she nearly fell over. I left it on going from low setting to medium and back, within minutes she was close to coming and I could tell. I hit the high setting and instantly she brought her fist to her mouth and started to shake a bit I slowed it down and she told me no not yet. I put it on high and she let out a slight scream and bit down on her lip. Her face was blushing and I kept hitting the medium and high setting and I could see her grinding her ass against the chair she was sitting on. She had in a shirt skirt and it was dark enough that I put my hands under her skirt and felt around her crotch and it was soaked. She asked we move tables as she had soaked the chair. We found her husband at the bar and he had it was easy to see that he had a few already as he was already heavily intoxicated. She talked to him for a bit I went and found myself sitting with a group of women that worked in another part of the building. A couple where hot so I was keeping my options open in case I went back to the room with out Allysa. I wasn’t sure how she was going to ditch her hubby but I was rock hard and needed some relief. Alyssa found me waved me over to her and we got a drink. At the bar I hit the toy on and again she had that look. All she mouthed was oh fuck then I turned it off. She leaned in and whispered please turn it back on. I told her I needed to blow my load as well. She had me follow her right past her husband at the bar he had no clue we walked right past him out side the hall into an empty conference room she checked it and it was open we walked around the corner of the room and she turned around drooped to her knees and ordered me to turn it on. I hit it on medium and would go from med to high. She sucked my dick and I wasn’t going to last I told her babe I’m going to cum. She was getting hit with a wave of orgasms when I blew the load right down her throat. She swallowed most but did have some come out the sides. She sat there in a wet spot with cum on her chin. We cleaned up went back in found her husband got him to there room put him to bed then I took Alyssa to my room which we had asked for rooms close to each other. We spent a few hours fucking and the past out. Then next morning I woke her up around 6:30 with a poke to her rear end. I hammered her ass hard and fast. She went to her room and as she walked in she saw her husband still past out. She crawled into bed with him. I had breakfast with them later that morning before heading home. He was hung over and before we left she met me in the hall to the restroom and showed me a plug and said meet later this afternoon.

    1
    # 69366 - by BigH / January 1, 2024
    - Embarrassing Moments -
    Straight Male / 41

    Got An Erection At The Doctor's Office.

    Right after I turned 13 and started Jr, High School I wanted to play football. We were required to get a physical in order to play. My Mom took me to the family health clinic and we went in to see Dr. Jill. Dr. Jill had been our family's doctor since I was a little kid.

    Mom took a seat in the corner as usual and Dr. Jill went thru the whole exam, listening to my heart, checking ears and mouth, tapping on my chest and back etc. while chatting with my mom. Finally, she told me to stand and slip my underwear down to my thighs.

    She did the "turn your head and cough thing" and at the age I was hairy and beginning to fill out if you know what I mean. When Dr. Jill started to handle my cock and balls, she mentioned to Mom that I was really a growing boy. Mom walked closer and as they both chatted, I looked down and my cock was getting hard.

    I looked at my Mom and her eyes were as big as saucers as she stared at my hardening cock. Dr. Jill still was cupping my cock and balls in her hand and my Mom said " He certainly is". Dr, Jill told me to pull up my underwear and she signed off on the physical form, gave me a hug and wished me good luck with football.

    That was the first time any woman ever saw my hard cock. After we got in the car, my Mom tells me that it might be time to have a "talk". Mom and Dad were divorced and soon afterward Mom began to explain the " facts of Life". but I already knew....LOL.

    4
    # 69365 - by Chris / January 1, 2024
    • - Embarrassing Moments -
    Straight Female / 23

    Sex Difficult Without Real Love

    I have some days were I can barely feel a thing so worried and masturbating to porn and climax is a low dive and zero excitement and other days its great and a high.

    3
    # 69363 - by Boobsome / January 1, 2024
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