What's the most embarrassing, sex related, thing that's happened to you?!

Discussion in 'Free Love' started by Calmerchameleon, Jan 5, 2023.

  1. Calmerchameleon

    Calmerchameleon Members

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    I have a few embarrassing sex moments in my life but the one that happened to me on Boxing day was a classic!

    My mother-in-law, who was staying with us over the holidays, was going through Christmas photos and videos on my wife's phone. Instead of going through the photos in the gallery, she browsed through Google Photos (on the cloud). Unknown to us, there was a video of me having sex with my wife from behind, going ten to the dozen, which we had deleted from gallery but had saved on the cloud! Having no thumbnail, my lovely mother-in-law, innocently clicked on it and because we were both preping food in the kitchen we didn't realise what had happened until we heard the 'noises'! It was like in slow motion when it dawned on us what was happening and we both raced out to take the phone off her! However, by that time she had already seen enough to know that it was us starring in the show! We all had a laugh about it over dinner but it wasn't our finest hour!

    Come on then, make me feel better, tell me your worst!
     
  2. olderndirt

    olderndirt Senior Member

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    My girlfriend and I had been dating for almost eight years before we married at 22. I refused to have sex with her because I loved her too much to risk getting her pregnant. She game me many handjobs and I fingered her to orgasm on almost every date. Finally, on our wedding night the moment arrived. My beautiful bride was naked, legs spread. and I was super hard. I entered her and almost immediately shot my load. I was so embarrassed! She had been fucked by several other guys, and I am sure I held the record for shortest fuck. We waited a few minutes and tried again. We had sex a total of seven times that night, and I never had another premature incident.
     
  3. Calmerchameleon

    Calmerchameleon Members

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    7 times! You more than made up for it then!
     
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  4. jimandjan

    jimandjan Member

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    Talking about Mother-in-laws. While living together with my wife, before we married. Wife's mother walked in and caught me nude. I felt her eyes were looking down. I may not be hung like a horse, but better than average. I wonder what she thought.
     
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  5. Andy Schumer

    Andy Schumer Members

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    Probably «lucky girl »
     
  6. olderndirt

    olderndirt Senior Member

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    It was quite a night/early morning. Both of us were sore.
     
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  7. jimandjan

    jimandjan Member

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    She smiled, I took it as a smile of approvable.
     
  8. jimandjan

    jimandjan Member

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    Got to take it easy, break her in easy, not try to wear her out. Hope you didn't have to wait to get back in the saddle. I found out later a couple of my wife's girlfriend, broke her in good with big toys. Never heard her complain about being sore.
     
  9. Andy Schumer

    Andy Schumer Members

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    It was more feeling bad than being embarrassed.
    I went for a massage that included the happy ending. Nicely done, no rush, all parts receiving the desired attention. But I reached the point where I was not able to reach orgasm from her hand. She accepted my request for a titfuck which I said often works in times like that.
    And it did but …
    Instead of laying inclined propped up with cushions or pillows she lay flat and I took my position. I rubbed between her breasts and it felt good, but I still remember mentioning about her position.
    Neither of us were holding my penis in the right position to aim the cumshot and also due to the curve on the shaft my cumshot squirted on her face. She jumped in surprise and she didn’t like it, unfortunately I had two reactions.
    First, I felt bad and that was not what I wanted to happen to her.
    Second, I found it amusing despite of myself and I laughed. That was something she DIDN’T like, even less and I could not find the right words to apologize.

    Needless to say she didn’t want to see me again.
     
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  10. olderndirt

    olderndirt Senior Member

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    Her other lovers in college had broken her in. I was happy she had experience.
     
  11. Calmerchameleon

    Calmerchameleon Members

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    That's funny!

    It reminds me of the time I had a happy ending massage when I was on a training course with Toyota. After a really long day of sitting in mini lectures and random group activities, I was aching all over. So back at the hotel, I Googled a local massage parlour that looked half decent. I chose an Indonesian/Thai parlour with all calming music and mini bonsai trees type place.

    So I genuinely innocently go there with the intention of getting a relaxing massage to get the knot out of my back.

    So the massage starts as you would expect with me naked under a towel on my front. The girl was a very petite Thai looking girl with a very tight body and very pretty face. You could tell she was a professional masseuse because she had really strong hands and knew where every knot was. So it was time to turn over.

    Now bearing in mind, at this point nothing on their website mentions or hints at any sort of sexual services are provided, not a single staff or myself has mentioned anything of a sexual nature so the next bit caught me off guard a bit! So I was naked, small towel over my bits, with a pretty girl massaging my leg and moving up to my thighs... Inevitably, there's a reaction under my towel (in which she notices). She just says "Do you want me to help you with that?" Pointing at the bulging towel. After telling me the price, I just thought, to hell with it, why not!

    She starts working on me and stroking me in ways I've never been stroked, her strong hands being put to good use. Needless to say, I couldn't last long and after the point of no return, I shot the biggest cumload I had ever experienced OVER my head and on the carpet behind me! The next wave hit my chin and the third wave hit my chest. I practically gave myself a cum facial! It was mayhem. I guess some of that extra cost for the service would be to cover the carpet cleaning!

    I don't know if it was the back massage or the happy ending but I slept well that night!
     
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  12. Lovnflman

    Lovnflman Members

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    Years ago the two kids were in bed, And my then fiancé, no wife, going at it on the living room floor about 2 AM. We freaked out when the kitchen light came on and “our” teenaged daughter was up to get some water. She stuck her head in the living room while we scramble to somewhat cover up with some large throw pillows. It was almost like she was sleepwalking, didn’t look for long, and went back to bed. And we were so embarrassed that we couldn’t finish and just went back to our bed. Years later, and I don’t remember the circumstances, she confessed yeah she did see us. I think my wife and I both blushed.
     
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  13. Calmerchameleon

    Calmerchameleon Members

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    That's funny! I think we've all had something similar happen to us!
     
  14. straightma1e

    straightma1e Members

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    One time was out in the desert. Performance was not an issue. The sun was. As in ultraviolet rays that not only tans your body but also burns it. We laid out a picnic blanket and had some fun. But I took to long to cum in missionary. I have no idea how long we fucked like that but it was long enough to where I was burnt from neck to heels including my ass. The wife was burnt every where in front except where my body covered her and over her back from when she rode me cowgirl. I couldn't sit for a week and peeled sheets of dead skin off after that. Not really embarrassing but difficult to explain to the boss why my ass was so sore that I couldn't sit at my desk to work. He was very religious and explaining the burnt ass due to fucking naked under the hot sun wouldn't have gone well.
     
  15. Danny Franks8

    Danny Franks8 Members

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    Having a lunchtime fuck with one of the girls in the office she was definitely keen for it.The building backs onto a forest and we were on the grass hidden by trees. When I got back to the office one of the juniors told me he saw me. He said that he masturbated while I was fucking her
     
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  16. David Vanzant

    David Vanzant Members

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    Back a few years ago a neighbor came up to me and showed me a picture of my wife getting out of the shower. He said he took it off his kids phone after a couple of his friends asked him if he wanted to go see a nude woman. I didn't ask him but if they had been watching for any time at all i'm sure they seen us fucking. The bedroom window is right next to the bedroom window and we usually have sex most night right after she takes her shower. Hope they don't think they need to fuck their gf's from what they saw us do. We may have warped their minds ;)
     
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  17. Romper

    Romper Lifetime Supporter Super Moderator

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    When my girlfriend and I were 18, we decided to have some fun when her father and younger sister left to play tennis. We lost track of time and the next thing we knew, we heard the back door opening. Caught like two rats in the barrel.
     
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  18. oldguynurse

    oldguynurse Lifetime Supporter Lifetime Supporter

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    Years ago I'd gone back to college at the tender age of 23. There was a 3 years younger girl who'd had grown up a few blocks from me in our home town, didn't know each other, just neighbors. At the college she'd introduced me to her girlfriend. We got along well and started an exclusive, and physical, relationship.

    One afternoon my girl-buddy, was at my apartment helping me clean up while my serious girlfriend was in classes. Don't remember how it started, but I have this image of her lying on her back at the edge of the bed, jeans off, legs apart and I'd just slid into her. A few moves and I came inside her. (the early days of the pill).

    I was still sorta cumming when, .....my girlfriend knocked at the open front door!! Fortunately, I'd hooked the screen door or else she'd have just walked right in! My entire life after that would have been completely different since we were together three more years and almost marrried.

    I yelled "be right there" while girl-buddy ran to the bathroom. I got pants up and ran to the kitchen to get a dish towel and dirty dish to explain why I took so long to get to the door was cause I was washing dishes. I told her girl-buddy was in the bathroom and she bought the story. Everything went on like normal after that.

    I can only imagine her on the toilet while my offering dripped out of her and her best friend was in the other room. She later married a good friend of mine and the incident was never talked about even 30 yrs later.
     
    Last edited: May 22, 2023
  19. Twogigahz

    Twogigahz Senior Member

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    Come to think of it, I did have one of those whoops type experiences.... It was a hot summer's day, her parents were out. We had been swimming near by and had walked home in our bathing suits and towels. Things had started a getting a little heated at the pool and we were in for fun once we got back to her house. Once we got in the back door, zip, off came her suit and she gave me that 'follow me' kind of look, and headed up to her bedroom, I needn't have been asked twice... I remember it was difficult trying to wiggle out of my wet suit with a boner and she was there on the bed, legs open, raring to go. She really liked oral...I moved her to the edge of the bed and gladly obliged. Once she made it over the top, she invited me in..."no, I mean now, I want to feel you.." Uh, no, as much as I wanted to, that Trojan was going on. Good thing, too, otherwise it would have been over way too fast .... When we were done she wanted to snuggle and I said no way, what if we fall asleep?? So she set her alarm clock...one of those early digital clocks with the numbers that flipped over...I dunno, we laid there maybe 15 minutes enjoying the delirious afterglow thinking of another round then we heard the rumble of the garage door opener below......SHIT!! So, she yells - quick !! Get into the shower !! Huh?? She'll think we just got back from the pool....So, I zipped across the hall into the bathroom, cranked the water on..she threw clothes on...a minute later I heard her yell down to her mom and she shoved my clothes in to me through a crack in the door so "she wouldn't see".... I think we pulled it off. Mom was cool, "how was the pool, you two?" We helped unload groceries in the kitchen....and there was her bathing suit, still on the floor...I kicked it under the table...mom was clueless... Later, as I was headed home, she leaned over and whispered to me..."smart move with the bathing suit...I got it.....oh, and I dressed so fast, I didn't put any panties on....." Something to think about on the way home...

    They were nice people, her parents, but pretty oblivious as to their daughter's high-geared sex drive...
     
  20. jimandjan

    jimandjan Member

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    That is so cool. I loved hearing my wife's stories. In our early years I traveled for work , in later years she traveled. If she meet someone she might have sex with them, but she always told me.
     

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