Worst Sexual Experience

Discussion in 'Relationships, Discrimination, and Jealousy' started by SpoiledPrincess, Apr 7, 2007.

  1. SpoiledPrincess

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    What's your worst or most cringeworthy sexual experience.

    I and an ex were staying at some friends, they kindly let us have their room and took the guest room as their room was nicer. It was gorgeous, white with indigo accents, white rugs, white walls, beautiful white satin quilt. One night we went to bed early and started watching a little tv, with no other lights on the room was dimly lit and as people are prone to we started messing around. I was having my period so he went for a dark towel to put under my bottom. In the dim light we got on with it, ending up with me gripping the bed head while he pounded me. Yum. We turned the lights on MY GOD!!!! it looked like a scene out of Texas Chainsaw Massacre. Pools of blood on the quilt, bloody hand prints on the wall. We spent the rest of the night sneaking in and out of the bathroom for cold water and sponges. It took us most of the night but thankfully we managed to restore the bedroom to it's former glory.
     
  2. ReRil998

    ReRil998 New Member

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    What. The. Fuck.

    Never touching my girlfriend on her period again.

    Ever.

    *cringe*
     
  3. B_NineInchCock_160IQ

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    oh come on, it's just a little blood. What the hell is with guys? They'll happily marinate their dick in sweat, vaginal secretions, saliva and possibly fecal matter for hours on end given the opportunity... get a little blood on the sheets and all of a sudden it's "EWWWWWWW!!!!"

    My worst sexual experiences that I can recall off the top of my head:
    1. My first and only homosexual experience. It wasn't voluntary.
    2. The first and only time I fucked a girl out of pity. She really liked me and I didn't think it would be that bad. Decided to never do that again.
    3. The first time I had sex with a woman much older than myself. She wasn't attractive and I did it "for the experience." Decided to never do that again.

    The above is why it's a policy of mine not to have sex with people I am not attracted to anymore. It's always been a negative experience for me. IMO, no sensation, new experience, or act of charity makes up for having to be intimate with someone you are not physically attracted to.

    also

    4. The first and only time I had a late, drunken, one night stand with some girl I had never met before at some bar. Decided to never do that again. In truth I was not that drunk at all, as I never really get that drunk, but it was very late and if you're extremely tired that's almost as bad as being drunk. It's also my policy now not to enter into sexual or potentially sexual encounters with significantly impaired motor or mental function.
     
  4. B_Think_Kink

    B_Think_Kink New Member

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    Being walked in on by my brother... while I was fucking my gay best friend who my brother threatened to kill more than a few times.... lol bad night...
     
  5. Skull Mason

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    Spoiled Princess that doesn't sound like the worst sexual experience it sounds kind of hot. If that is your worst I would hate to see what you can get done on a regular basis.
     
  6. dickman45885

    dickman45885 New Member

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    I guess worst would be same as one I have posted previously.

    I was under the influence of substances still illegal and was fucking a female I would not normally have fucked. Mid stroke I said to her, "Gosh, if I were not so loaded I would not be fucking you." She must have felt the same way....she let me finish.

    I also was caught a couple of times by one of my sisters, or mother, but nothing of any consequence happened.

    I was also caught fucking my girlfriend at her house, by her brother. They had split level house and thinking we were fthe only ones there were fucking on some interior steps and not being rel quiet about it. All of a subben her brother popped out and says...."Oops, I thought I heard someone out here." He must not have said anything because we never heard about it from her parents.
     
  7. D_Dick_Dock_Doe

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    I was super horny one morning, so I decided to invite some guy I met online to come over to my place for some mid-morning fun. I was under the impression he was going to let me fuck him, since we had agreed to such online, so I was thrilled. When he showed up, thing s went HORRIBLY wrong.

    We were kind of fooling around on my bed and he started to suck REALLY HARD on my neck. I told him to stop since it was really hurting me, and I told him "no hickies." I had a very important interview the following day and was not about to go into it with a huge purple mark on my neck as if I was 16 years old and trying desperately to prove I was sexually active.

    Well, to say the least, he didn't get it, and kept sucking like a Hoover vacuum...so hard it was extremely painful. I told him for a second time to stop it or I was going to get pissed. Of course, he starts at it AGAIN, and this time it REALLY hurt. I slugged him, and he fell off my bed. i jumped up and said "ALright asshole, you need to leave right now. You obviously don't understand boundaries." He gave me a look like "what did I do?" He put on his clothes and I went out to lunch with a friend.
     
  8. D_Harry_Crax

    D_Harry_Crax Account Disabled

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    The three times in my life when I ended up in bed with (three different) guys whose ERECT cocks were each about 2 inches long (the next shortest guys I've been with have been at least 5 inches).
     
  9. vino123

    vino123 New Member

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    Many years ago I was on the Blind date with a lady who was 10 years older than me, she really wanted to have sex but I was not attracted to her, I was talking with her for an hour to just get out and not give her an impression that I did not like her, but I ended up having sex just because of pity, that was a hard lesson for me, no more blind dates since then and I definitely learned how to say NO, of course I was very young back then.
     
  10. B_NineInchCock_160IQ

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    Some people just suck.
     
  11. SpoiledPrincess

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    It was kind of hot - until it kicked in that we'd have to spend hours cleaning up. I have no problem with any sort of sex whatsoever during my period, and I've never encountered any guys who do either, in my experience once a guy's horny he loses any sense of squeamishness he might have had.
     
  12. dongalong

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    My worst was also my most painful, I had woken up with a crick neck and had to go to work, by the time I came home it was feeling better but when I had my shower I had a shock because my then girlfriend had used up all the hot water, the shock made my neck MUCH worse.
    SO to make up for her mistake I made her do all the work when we made love, it was enjoyable until I moved my neck! OUCH!
     
  13. swordfishME

    swordfishME Member

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    I have been in a relationship (with a woman) where I was afraid to say no. Worst sexual experiences of my life (We did it 34 times over a 6 month period).
     
  14. Xii

    Xii New Member

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    One of my worst sexual experiences was with a boyfriend who decided in his infinite wisdom that anal sex was just like the pornos where guys can slip in and out at will without giving warning, let alone lubing up. At the time it was uncharted territory for me, and after his miserable attempt I ended up in the
    fetal position cringing for half an hour.

    I dumped him good.

    :)
     
  15. Male Bonding etc

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    So many things went wrong this one time, I'll only share some of them. Her bush was bushier and hairier than any I'd seen before. Then she had inner labia dangling down like liver, and I'd never seen that before. I was still ready to fuck her though, except that when I rolled on the regular sized condom it was so tight I lost my erection when I got in her. THAT had never happened before. I was STILL so worked up that I tried to go down on her (even knowing she had Herpes), but when I got my tongue there (despite her trying to push me away) it tasted like the condom. Finally, I gave up... Now, I get cold sores once in a while and wish I'd never "gone there" with her.
     
  16. swordfishME

    swordfishME Member

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    Thats what you get for "doing it" with Paris Hilton!
     
  17. chrstphrrr

    chrstphrrr New Member

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    I was very drunk and going down on a guy I barely knew and barely liked in the driver's seat of his dad's pick-up truck. :blowjob: He kept forcing me down past my comfort zone (he's got a fairly long, thin dick) and my usually well-suppressed gag reflex kicked in, aggravated by the half a bottle of tequilla I'd consumed and...upchuck! :684: He was not cool about it. :zx11pissed:

    I laugh about it now (and a little bit then), so it's probably more his worst sexual experience than mine, but I'm still a little gun-shy about deep throating. Besides, he can't tell anyone about it because he's "straight".:wink:
     
  18. ssongs

    ssongs Active Member

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    Well I definately have all of you beat! When I was stationed in Italy, I would sometimes go out and get a prostitute, since it was legal. In Naples, there are no fancy whore houses like there are in Germany or Amsterdam. You just pick up a girl on the street and do it in your car. Or if you're a big guy like me, you find a quiet spot and do it outside of your car.

    So one night I was really, really drunk (again) and I picked up a hooker. She was blond, thin, had a deeper voice, but I thought nothing of it. I paid her and we got things going. I of course put on a condom. Anyway after a descent bj, we get on to fucking. Oh, also during the bj I tried to put my hand on her head, not to force her to deepthraot, just for something to touch. And when I did, her hair was an obvious wig. So anyway we get to fucking and she just turns around and shes got some kind of crotchless panties on, and just takes my dick and guides it in there. What was I fucking? An ass, a pussy? Who knows!? Anyway after a little bit, I take out my dick and, surprise, the condom is broke. Not just a little hole in the top or something, but it is now a ring of laytex around the base of my cock. That scared the hell out of me. So I jerked off, came on my car, and got out of there. For the next couple weeks I worried that my dick would turn blue and fall off. I haven't done a hooker since. And now when I'm with a woman I make 100% sure that she is a woman.

    I did get tested, as I was in the military and you had to every year or so. Nothing came up, so dodged a bullet.

    Beat that!
     
  19. thk8plus4u

    thk8plus4u Member

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    NineInchCock writes:

    My worst sexual experiences that I can recall off the top of my head:
    1. My first and only homosexual experience. It wasn't voluntary.


    Very curious to hear about your one homosexual experience!
    Insanely jealous that I didn't get there first. I think you would
    have found it a pleasurable adventure.
     
  20. Blocko

    Blocko Member

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    I don't want to read the OP's mind, but you could be a little more sensitive when it comes to other people's *involuntary* sexual experiences.
     
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