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What was your worst sexual experience? What made it so disappointing?

Just thought I'd try to spice things up a bit in here...we had a nice streak going a while ago but things have settled down. So, let's ramp it back up again!

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  1. amybyrd21
    Ok I had a friend that said that all sex was good sex. (He was a man)

    My ex. I would just lay there. lol and pretend to sleep. He was truly bad at it.
    1. brianomaracroft
      What made him so bad?
    2. amybyrd21
      he just had no talent and it was small
    3. brianomaracroft
      That's kinda a losing combo.
  2. nothingprofound
    From 1957-1963. 1972 was also a bad year.
  3. LisaNYC
    I suppose it was with inmate 43532 at the State Penitentiary a few years ago. He was a hottie, but conjugal visits are always so confining.....plus the voyeuristic prison guards were constantly peeking in through the door peephole. Kind of ruined the mood!
    1. brianomaracroft
      I would imagine.
    2. DollinNYC
      oOo you got his digits!!
  4. sjtavo
    hmmmmmmm worst? first one that pops into my head is Nate - such a cutie, he was about 23, I was 32. He had had a crush on me for years so we finally got drunk after a friend's calling hours and slept together. unfortunately, Nate qualifies as having a pencil stub for a penis - but he had these huge powerful forearms because he was a bricklayer....so he basically screwed me with his arm. It was odd, it wasn't totally unpleasant but needless to say, I never slept with him again.
    1. brianomaracroft
      A pencil stub?
    2. sjtavo
      ya - poor guy, he's absolutely adorable, hot little body, and i swear, his penis was about 3 inches long and as thick as my thumb. major disappointment.
    3. brianomaracroft
      I thought the pencil stub sort of deal was mostly a myth. One of my friends described her ex-boyfriend as "somewhere between a cocktail weenie and a human thumb." I thought she was kidding.
    4. Onchong
      You are a very naughty Lady, but I like the way you put things in words. LOL
    5. sjtavo
      Brian - it is a sad but true state for many men - i've experienced a few in my life - though Phil was definitely the smallest (didn't even know he was inside me).

      Onchong - LOL you haven't read many of my discussion threads or my blog - you should check it out and then you'll get a glimpse into my personality
    6. ckent27
      Yes. Penises can be that small. I've been with guys who I've felt genuinely sorry for.
    7. AroundTheWaygirl
      I feel quite lucky in life as I have never encountered a pencil stub!
    8. ckent27
      I feel quite lucky not to have one!! :-)
    9. bettieblogger
      That's not a penis .. that's cocktail weenie.
  5. aspotofblog
    One where the guy pulled my hair like I was some kind of porn star and another where the guy was doing the dumbest dirty talk throughout. It was about as sexy as toenail clippings in bed. I just wanted it to be over.
    1. brianomaracroft
      So you aren't a fan of toenail clippings, then?
    2. aspotofblog
      By all means, have toenail clippings! Toenail clippings are a natural part of being human. I just don't want to feel a toenail digging into my back whilst in bed.
    3. brianomaracroft
      That might be a mood spoiler, yes.
    4. AroundTheWaygirl
      Really, you didn't like the hair pulling? I'd think that would be a bit of a turn on. Mind you, by hair pulling I don't mean that after he pulls, most of your hair is in his hand. I'd elbow him in the eye sockets.
    5. aspotofblog
      Some women do. I don't. He practically yanked my hair.
  6. AroundTheWaygirl
    I had a similar experience to sjtavo's only I didn't get to see his "stub". His name was Dean. I was around 27, he was 20, we were co-workers. We had a connection at work, I guess you could say hot for each other, and would always make remarks like what we would like to do to one another given the opportunity. Well, that opportunity came one night when he asked me if I wanted a drive home. Of course I took him up on that. So, to make a long story short, we started fooling around (while he was driving), I felt the need to get into the drivers seat with him. Things were going good and decided that we better pull over somewhere because this was an accident waiting to happen. We get pulled over, practically ripping each others clothes off when he pipes up and says "I can't do this" and grabs himself between the legs. I was like wtf and let him know that he was still driving me home. I'm thinking that he had trouble getting it up the whole way home or maybe had a girlfriend that I didn't know about and was feeling guilty. Nothing was said about it for the longest time, a few years even until I ran into him at a bar a few years where he apologized to me. He said he "went" in his pants and was embarrassed. Poor sucker. Poor me.

    The funniest thing about it was that at work, he would always refer to himself as "Dean The Machine".
    1. brianomaracroft
      That's hilarious. Sad, a little, but hilarious.
    2. sjtavo
      LMAO that is absolutely hilarious!!! awwww, poor guy (LOL)
    3. AroundTheWaygirl
      I know right. You have no idea. I left a lot out because I could have been her all day with this story. It will be a classic forever.
    4. ckent27
      As a guy who was once 20, that can happen very easily! LOL. It takes a few visits to the rodeo to learn how to control things.
    5. AroundTheWaygirl
      The thing is, I wouldn't have had a problem with that if he had told me. Hell, my philosophy is get the first one out the way then it's game on, round 2 ya know? Oh well, perhaps he has a better handle on it now and is having mind blowing sex these days.
    6. sjtavo
      absolutely babe!! cum at once and then don't cum for awhile, that's my philosophy!
    7. AroundTheWaygirl
      Cheers to that sjtavo!
    8. bettieblogger
      the fact alone that he grabbed it and used the words "I went" would have sent me running from the car lol ...
    9. brianomaracroft
      Yes. "I went" sounds more like he peed himself rather than jumped the gun.
    10. AroundTheWaygirl
      Well, in any other circumstance I probably would have but by him grabbing himself, I just assumed that was a hint to me as to not touch him any further. What an awkward moment ...
    11. brianomaracroft
      I think it would be difficult for some, if not all, guys, to admit that they got THAT worked up and couldn't follow through. I can imagine how awkward it would have been for both of you.
    12. ekim941
      "Machine" is right, he is fully automated.
    13. AtlanticEquity
      "Dean, the Yogurt Machine!"
  7. rcrane52
    it was definitely when my hand fell asleep while ... well ... you know ... um ... while kneading the knob is one way to put it. anyway, it took months of counseling but everything's much better now. we came to an understanding ... so to speak.
    1. brianomaracroft
      Yeah, if your own hand betrays you, you're in trouble.
    2. AroundTheWaygirl
      Indeed. If you can't rely on your own hand, than who can you rely on right.
    3. bettieblogger
      I believe they call that "The Stranger"
  8. MrPoo
    I promise, it has nothing to do with animals
    I remember once I did cut some chilis and haven´t washed my hands that properly. It was a burning experience
    1. AroundTheWaygirl
      Owww! For her or you? lol
    2. MrPoo
      Ha ha ha... both of us, and it dont stop burning, even a cold shower wont help
    3. brianomaracroft
      Brings to mind an unfortunate red pepper flake that went missing during our "Pad Thai in bed" day...we found it soon after, sadly. According to my wife, it really, really hurt.
  9. aspotofblog
    Are there any GUYS out there who've had bad sexual experiences? I know many guys say the only bad sex is no sex, but I'm not convinced.
    1. MadameX
      Well, they may not have known it before, but I'm pretty sure that any sexual experience that ends up with a woman mocking you by name and description of your anatomy on a public message board that will be around forever qualifies as a "bad sexual experience".
    2. brianomaracroft
      Yes, that could be true...
  10. wagerwitch
    My ex hubby was intoxicated and I was in the middle of chemotherapy for HepC - which left me feeling horrible and barely able to function... Anyhow since we hadn't had sex for a long time -he was a bit offended, hurt and upset that I hadn't pleased him (he just didn't get the concept that I was sick and had been sick for a long time - and sex just wasn't feeling all "THAT" sexy... And of course by that point I had a lot of resentment... that he wanted sex - and I just wanted to feel better...

    Anyhow... long story short... (hubby was NOT anatomically SHORT - by the way.)

    I just laid there while he literally drooled on me - and tried to turn me on while all I could think of was "Don't puke... I'm freezing, I'm hot, OMG my legs hurt, OMG my guts hurt... Is he done yet? FREAKING HURRY UP!!!! Touching me hurts! Just hurry up".

    It was the longest half hour in my life - and while I didn't say no - my body was screaming it.

    And I hated every freaking second of it which each one felt like an eternity.

    I'm sorry he didn't get "it" all that often after I got sick...

    But I hated him after that... Which is sad - cause basically he is a GREAT guy.
    1. brianomaracroft
      That's rough. When my wife was sick, it certainly curtailed some of the bedroom activities.
  11. drjalee52
    Loveless sex is not very gratifying.
    1. AroundTheWaygirl
      It is when your single and just want to get some, no expectations, no strings attached.
    2. sjtavo
      loveless sex is the best - i don't need love to intercede with some great booty - sex is nothing but a physical desire - it's not emotional for me. it's animalistic.
    3. Andre412
      drjalee52 - maybe you’re not doing it right ?

      I mean loveless sex is well - lustful and new - exciting and what you make of it, as aroundtheway girl puts it no expectations and no strings, which in some ways allows you to do things you wouldn’t ordinarily do with the one you love.

      that said there is no comparison between sex with love and sex without
  12. polybore
    You are asking the wrong person really.
  13. carsonfb
    When my wife and I were first married, my in-laws arrived 2 hours early from out of state. Her dad wanted to make sure we were awake so that we could let them in, so he pounded rather briskly on the bedroom window to our basement apartment. Nothing kills the mood like "WTF is that!". It sounded like a car was trying to crash through the window.
    1. brianomaracroft
      Parents are definitely an amour killer.
  14. LolitaV
    Sex with a cucumber (?)- it tried: IT SUCKED!!!!!
    1. lotusb
      Me too!! Did you try heating it up a little in the microwave? It helps.
    2. brianomaracroft
      microwaved cucumbers?
  15. Men101
    Huge got really tiny pretty quickly.
  16. alivasim
    I had a sex with the girl who never got into the process before...damn it was so horrible...
  17. lotusb
    This guy a friend hooked me up with. He just laid there and I got on top. He was so nervous that he came after like 4 seconds. Then he couldn't get hard again. I was so pissed off that I literally told him to get the fk out of my house and never call me again because his sex was weak and a waste of time. I thought he was going to cry.

    I was 17.
    1. lotusb
      OH...I forgot. Once my HS sweetheart and I were skipping school to mess around. We were at his brother's house on the living room floor BUTT NAKED doing the freaky dance. His brother suddenly swung the front foor open and we ran into the bathroom. After his brother was done laughing he grabbed what he came for and left. I was SOOO embarrassed. I think I cut the poon off for like two weeks after that happened.
    2. brianomaracroft
      So four seconds is fast, huh?
    3. othellobloke
      Does that guy murder prostitutes in his spare time?
  18. thecantankerouscan
    I slept with a guy once who was so bad I watched the news over his shoulder. I don't even like the news.
    1. xmarks
      Honey, is that you?
    2. brianomaracroft
      That sounds pretty bad. Either that, or the news in your area is very compelling.
  19. DAVI
    In Cuba I was at a party at a friends farm. We were doing it in a bedroom by the front door. It was raining and all the locals were there. An old couple walked in for their umbrella.
  20. aningeniousname
    I would go with anything that has the potential to split my colostomy bag, so nothing rough or anything that involves sharpened objects or industrial lubrications that can degrade medical grade plastics.
  21. DAVI
    Y, medical grade plastics can get in the way of the erotic arts.
  22. othellobloke
    I once had sex with a girl who'd just given birth about a lil while before and was so loose I couldn't feel her muff at all.
  23. cookingasshole
    your mother was pretty bad
    1. brianomaracroft
      You just didn't romance her, that's all
  24. ArsenicCookies
    Second time I hooked up with former baby daddy dude, I was hella drunk and decided to figure him out and jumped different positions. We found one that was awesome but my stomach was upset from the booze so I leaned back a little too far and had one of those awkward "did i break your penis" moments. Worst fail ever lol
    1. sjtavo
      I've done that - riding him like crazy, he's half lifting me off him and pounding me back down, it was awesome! til he lifted me a bit too high and when he he pounded me back down, he almost broke my pelvis and his dick. he was pretty sure his was broken and i was crying LOL god that hurt. thankfully, troopers that we are, we recovered and continued after about half an hour of prayers LOL
    2. brianomaracroft
      I think splinting helps
  25. bexablancas
    One time I had sex that required me to use an ice pack on my crotch when I got home (more like, when I ran away in the middle of the night)

    And trust me...this was not the good kind of needing an icepack...this was the....swelling type....

    eh.
  26. AnastasiaFB
    The first time; too sore.

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