What was your most disappointing sexual encounter

Discussion in 'The Orgasmic Experience' started by TylerDurden2019, Jul 8, 2019.

  1. Romper

    Romper Lifetime Supporter Super Moderator

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    No, it didn't end there, but I was expecting a lot more than I got.
     
  2. Romper

    Romper Lifetime Supporter Super Moderator

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    I went ahead and did her, but it wasn't nearly as good as I had planned on it being. I mean, how can sex with a blonde be nearly as good as sex with a redhead.
     
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  3. Tonynewyork6969

    Tonynewyork6969 Members

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    So there is a divorced milf in the neighborhood who is pretty stuck up. My fwb hates her. Anyway we chat every now and then when we meet at starbucks or the supermarket etc. she is totally hot about 5’1, toned and tight blonde hair fake of course. Anyway a few weeks ago we met at starbucks and she asked me if I had a few minutes to help her move a small file cabinet. Who am I to say no lol. So I help her out and she asks me if I wanted a glass of wine. We started chatting and one thin leads to the next and we start to make out and she starts to rub my pants. Anyway she starts to blow me. Not so good I can see why she is divorced. I eat her to an orgasm and then fuck her. She is just lying there like she doesn’t know what to do. I came and left after a bit politely. She texts me and I text back as I am not rude but totally disappointed.
     
  4. Gojira Man

    Gojira Man Members

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    Several and unfortunately drug and drink were involved, reducing the participants to flailing zombies. One in particular, was a lovely buxom young lady with whom I awoke, both of us having passed out in our underwear. It had been one of those parties where the sun rises, the birds sing, and you know that the candle had been burned on both ends....fully. We managed something but the hangovers were too brutal. The act was slow, short and unmemorable. I later regretted and was never able to reconnect with her. An opportunity lost.
     
  5. Josephinelcajon

    Josephinelcajon Joseph

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    When I first started to cum at 11 a friend (girl-not girlfriend) was over when I told them all I started to cum. All wanted to see. Us guys masturbated together before, but she had not. She was the focus of our attention but soon turned to my new ability to cum. She wanted to do it for me. She was very awkward and worried I would cum all over. Asking a million questions how far how much. I did finally orgasm but just a few drops. Between her stroking and questions, me just starting to cum it felt like a BIG let down in performance. We all got to see me cum the next day a good shot up my chest which amazed everyone.
     
  6. oldguynurse

    oldguynurse Lifetime Supporter Lifetime Supporter

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    Got delegated by my hospital to attend a medical products conference in New Orleans. During the Saturday afternoon presentations, lectures and sessions I got to flirting with, and having it returned by, a lovely lady a few years younger. It got to where there was definite chemistry, light touching. and imagination going on for both and we decided to meet in my room at 8:00. Now, I hadn't been laid in months and my anticipation was so high I started having some vodka to calm myself. Ooops! A good idea, taken too far.

    By the time she got there, looking gorgeous and quite ready, I was truly plotzed. Even after 20 minutes of making out on the bed, MrHappy could not come to full attention. I made up for it by licking her pussy awhile, with which I'm usually able to make ladies cum. But I did such a bad job of it she couldn't make it. We called it off and decided to meet for breakfast in the morning, and she left. Yes, we did meet and got along wonderfully as I kept apologizing and both agreeing we would have fucked each others brains out. It was a moment lost.
     
  7. Romper

    Romper Lifetime Supporter Super Moderator

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    So, why didn't you get with her again and start over? Opportunity lost.
     
  8. oldguynurse

    oldguynurse Lifetime Supporter Lifetime Supporter

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    The conference ended at noon that day, and she had company things to pack up. And I still remember her full name, V_____ L____ T______.
     
  9. Romper

    Romper Lifetime Supporter Super Moderator

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    What a shame. I hate missed opportunities like that. When single, I would never drink too much when the possibility was there.
     
  10. straightma1e

    straightma1e Members

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    The last time i got to fuck a pussy was frustrating if not disappointing. I really didn't have a good mindset and even though she felt great and did everything right I couldn't reach orgasm. No matter how hard we tried i just couldn't get there.
     
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  11. Tonynewyork6969

    Tonynewyork6969 Members

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    As an update the blonde milf texted me to move boxes again which i knew was code for fucking. She was dressed in a tight tshirt and jeans and a wry smile. She gave me a glass of wine and asked me if I could repeat what we did last time. I ate her out and made her squirt which she said she never did before. She blew me a little and then i fucked her to a few orgasms again. she said she never felt the way i made her feel. She also said she did not have many partners outside of her ex husband. She is 39 and is so hot . At 61 we are enjoying our time together but I don’t have any connection like I do with my fwb , wife, fb and the twenty somethings. Still it is a win win for both of us.
     
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  12. Pussytimes

    Pussytimes Members

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    My disappointing sexual experience was. I was on med because of fever and after few days fever have gone but doctor told me continue eating med till is finished which heavy antibiotics. My wife bisexual friend come visit her they start playing with eachother after charging up both need a fuck my wife call me but hardly get up even my wife and her friend both have try oral nothing happened both women were horny and furious too that day..
     
  13. scratcho

    scratcho Lifetime Supporter Lifetime Supporter

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    All the ones I passed up , which were many. :(:(
     
  14. jimandjan

    jimandjan Member

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    I think that's something we all regret. But I know a couple that I'm sure I made the right choice, and let my big head think before my little head.
     
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  15. curiousgeorge

    curiousgeorge Senior Member

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    Amen!
     
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  16. oldbeater

    oldbeater Guest

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    You should have eaten her pussy first until she had an orgasm
     
  17. Andy Schumer

    Andy Schumer Members

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    jeezus. Not jealous or feeling sorry about myself but saying, I can’t even seem to be able to find just one fwb, that’s all I’m looking for
    Thought I had one, a coworker, but things didn’t go far. I cautiously tested the possibility with another one but she’s a no-go.
    I can’t be asking too many girls at work.
    Not going with supervisors, avoiding any possible conflict; just the way I am.
     
  18. The Shark

    The Shark Members

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    Worst experience I’ve ever had was this girl I dated about 20 years ago. She was beautiful and had a great body - but she had a laundry list of rules for the guy that it really took the enjoyment out of dating her. Even sex was a letdown so much that one afternoon we were at my place and had some impromptu sex. We were tight on time which may have factored into it - but she kinda just laid there and made me do all the work. Even though we weren’t using condoms and I was hard as a rock I still couldn’t cum.
     
  19. jade-

    jade- Members

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    A guy was eating me our and it was painfully underwhelming. He sneezed into me too :neutral::mask:
     
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  20. 6Sailor9

    6Sailor9 Lifetime Supporter Lifetime Supporter

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    Ohhh! :-(
     

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