Worst sex you've ever had

[DRDavenport]

Originally Posted by outlander2

... I fucked a girl one time who breathed in a really weird pattern when she fucked and then seemed to almost pass out when she came. She was only out for a couple minutes but the first time it happened I was in a near panic wondering if I had literally just fucked one to death. Then I saw she was breathing. Loved fucking her but the passing out freaked me out so I found a reason to move on.

That's unusual, but not abnormal. Masters & Johnson documented it and studied the physiology. It just means you did a good job.

DR

[delt]

My best and worst sex both came from my wife. Early in our dating, I had undressed her and fingered her to a cum, then asked for a blow job. She did not know what that was so I explained and to my glee, she said ok. I leaned back in the driver's seat and pulled out my very hard cock and she licked the head then proceeded to go down on it and began chewing. Her teeth were sharp and it hurt terribly. I yelled and she pulled off, and I explained that the oral sex act was supposed to feel similar to the warm, soft damp feel of her pussy(which I had not fucked). She was sorry but I was so uncomfortable we did not continue that day. Over time, she learned thank heavens.

She was such a virgin, she had not even fingered herself and it was a challenge to first finger her and later to fuck her. I am not well hung, average at best, but it took numerous tries to get her relaxed sufficiently and lubricated that I could eventually get my cock in her. I was very frustrated but at least I was her first. I could not fuck her when she was in pain, so it took a while. Of course, in time it was wonderful.

Finally, I will mention a massage I got in Salisbury, NC on a long trip about 20 years ago. It was a "health spa" located just off I-85 next to a hotel on an access road with parking in the back. I went in and waited for a 20-something white girl to call me in. I got the hour long massage and she did a very basic massage on my back then asked me to turn over. I was horny being away from home so long so I was erect and she asked if I wanted the full body massage which would cost extra. I paid the extra and she grabbed my poor cock in a kung-foo grip I will never forget. She had it in a major squeeze and I begged her to let go. She did and I showed her the way I wanted it done, which I assumed was what everyone enjoyed. I had her put oil on it and she began to move her hand up and down but it was not very good. I finished myself, just wanting to give her something to clean up, and I explained that it was in her best interest to give very good handjobs to get bigger tips and to get the guys off quickly. She told me that she was new and had never given handjobs to any of her boyfriends, they just wanted blowjobs or to fuck. I never went back and if I had to be in North Carolina, I never stopped anywhere near Salisbury.

My best "massage parlor" experience was in Maryland. I went in and a guy about 70 was in front and told me that it was my lucky day. He owned the massage parlor and had just won some sort of lottery for $100,000(he held the ticket in his hand). He was going to give the girls two days off---with good pay---but he had told them they had to treat the next customer special. I was very suspicious thinking it might be the cops or something but he nor any of the 4 girls would take any money. All four rubbed my back at the same time, and when I rolled over, they all took part in making me a very happy guy, including a prostrate rub and all the extras. Two of the girls were really cute, the others only average, but with your eyes closed, 4 girls felt really good.

[animal1242]

Originally Posted by outlander2

Guys, women who hum or recite the alphabet are broken. Whether it is due to upbringing or a bad experience I don't know. I fucked a girl one time who breathed in a really weird pattern when she fucked and then seemed to almost pass out when she came. She was only out for a couple minutes but the first time it happened I was in a near panic wondering if I had literally just fucked one to death. Then I saw she was breathing. Loved fucking her but the passing out freaked me out so I found a reason to move on.

once had a girlfriend who was totally frigid,as in had never had been penetrated. always being up for a challenge I decided that I would have to "cure" her. it took about 6 weeks but when I finally made it ,she had her very first orgasm and passed out for about 30 seconds.i too thought I had fucked her dead. I freaked. because she had never had an orgasm she did not know she did this. from then on if we fuked and she didn't pass out I knew I had done a lousy job on her

[Vcpl]

PN, I feel for you. My first wife would go on hot and cold spells. Sometimes she wanted it everyday for a couple of weeks, then she would go cold for a couple of months, but nothing like what your describing.

The worst sex I ever had wasn't actually sex but a bj. My senior year in high school I hooked up with this cute brunette coworker, who I found out later was a total nympho. Anyway, on our first date, she was pretty forward and said she loved to suck cock and when the movie was over, she practically dragged me back to the car. Once in the car, she couldn't my cock out fast enough and I thought I had died and gone to heaven. Man was I wrong.
Turns out she had just gotten her braces a few days before we met, and hadn't given a bj with the braces. It was so painful I had to make her stop which really sucked. She was the first girl that wanted me to finish in her mouth and but it hurt way to bad to even think about cumming. She apologized and said let's f**k instead. Not a problem, we tried every position we could get into in the back seat of my car which is when I learned what the term multi-orgasmic meant. That girl was a tiny but powerful orgasm factory. She just kept cuming and cuming. After 30 minutes or so, my poor pecker was starting to burn and the sex was getting painful, so I finally nutted, got dressed and took her home.
The next morning was one of those WTF????? moments. I quickly realized why it burned so bad during while I was having sex. When I got up to pee, my poor dick hurt just to touch it. When I looked at it, the head was a bright purple and looked like some one had taken a razor blade and sliced it every which way, some of the cuts had actually bled and I a bunch of little scab on the head. It took a week for the cuts and pain to go away and another twenty years before I could enjoy a bj enough to actually cum in a woman's mouth.
The first wife tried, as did several other girl friends, many of them taking it as challenge, but it never happened.
Finally, after 2 years of trying, MrsV was able to get me off with just her mouth. Oh man, what a relief to finally get that trauma out of my head, actually, both heads. LOL

[PuffyNips]

Another bad sex encounter.

When I was a sophomore in college there was a girl on my floor who I flirted with. We had good chemistry. I could tell she felt it too. But I already had a girlfriend, so the flirty girl would never let me get anywhere with her.

When I was a junior, I no longer had a girlfriend. But as bad luck would have it, the flirty girl went to study in Paris for the year. Interestingly though, she sent me a letter, a very flirtatious letter saying she heard I no longer had a girlfriend. We started to write back and forth to each other. I enjoyed it. But it was also difficult. It was foreplay though letters. It was like we lived in the Elizabethan Age.

So finally senior year came around. She was back on campus. We got together for dinner. It was great. She was such good company. Closest thing I've ever had to a soul mate.

She revealed to me that she was still a virgin. She was hoping to take care of that in Paris, but nothing. She asked if I might want to help her with this problem...

This was getting good. We arranged to meet that Friday.

We opened a bottle of wine. We ended up on her bed kissing. I remember she was wearing a red sweater. I pulled it off. I unbuttoned her shirt. I unsnapped her bra. I sucked on her nipples. I undid her belt buckle....

A few minutes later she was naked, as was I. I got between her legs and started to press the tip of my cock against her labia. I asked if she was okay with this, was she ready, it might hurt a little. She gave me a nod....

But just then, the phone rang. I couldn't take her virginity while the phone was ringing. That's just too weird. I waited for the phone to stop. It rang like 20 times. This was before answering machines. Like holy fuck, how obnoxious.

Once the ringing finally stopped I couldn't just push into her. The mood was all wrong. So I started kissing her again and caressing her. I did this for a few minutes before once again getting into position between her legs. And then the damn phone started ringing again!

This time it just wouldn't stop. It was like 30, 40, 50 rings. I finally said to her, "Look, you better answer the phone or they will never stop."

So she got up and answered the phone.

I was of course listening and I hear her say, "What.... WHAT?... What are you saying.... No... NO NO NO!!!!" Then she starts balling her eyes out.

And I'm like, "What's going on?"

She tells me it's her father on the phone. Her brother just died. His roommates found him in his apartment lying on the bathroom floor. They called 911 but apparently he was already dead. [A few weeks later they figured out the cause. He worked in a nursery and had been administering bug poison to the plants all day and had gotten too much of it into his own system and it killed him.]

But here I was. It was like a two year courtship leading up to the exact moment of me taking her virginity, when suddenly death calls on the phone.

Talk about breaking the mood. It was such a bad feeling for me. I can't imagine how bad it was for her. We never got together again. As if losing her virginity, and sex, and a relationship with me, was forever tied to her brother's death. And it was insurmountable.

She could have been the one for me. But we never got to find out.

[abs14]

Originally Posted by PuffyNips

Another bad sex encounter.

When I was a sophomore in college there was a girl on my floor who I flirted with. We had good chemistry. I could tell she felt it too. But I already had a girlfriend, so the flirty girl would never let me get anywhere with her.

When I was a junior, I no longer had a girlfriend. But as bad luck would have it, the flirty girl went to study in Paris for the year. Interestingly though, she sent me a letter, a very flirtatious letter saying she heard I no longer had a girlfriend. We started to write back and forth to each other. I enjoyed it. But it was also difficult. It was foreplay though letters. It was like we lived in the Elizabethan Age.

So finally senior year came around. She was back on campus. We got together for dinner. It was great. She was such good company. Closest thing I've ever had to a soul mate.

She revealed to me that she was still a virgin. She was hoping to take care of that in Paris, but nothing. She asked if I might want to help her with this problem...

This was getting good. We arranged to meet that Friday.

We opened a bottle of wine. We ended up on her bed kissing. I remember she was wearing a red sweater. I pulled it off. I unbuttoned her shirt. I unsnapped her bra. I sucked on her nipples. I undid her belt buckle....

A few minutes later she was naked, as was I. I got between her legs and started to press the tip of my cock against her labia. I asked if she was okay with this, was she ready, it might hurt a little. She gave me a nod....

But just then, the phone rang. I couldn't take her virginity while the phone was ringing. That's just too weird. I waited for the phone to stop. It rang like 20 times. This was before answering machines. Like holy fuck, how obnoxious.

Once the ringing finally stopped I couldn't just push into her. The mood was all wrong. So I started kissing her again and caressing her. I did this for a few minutes before once again getting into position between her legs. And then the damn phone started ringing again!

This time it just wouldn't stop. It was like 30, 40, 50 rings. I finally said to her, "Look, you better answer the phone or they will never stop."

So she got up and answered the phone.

I was of course listening and I hear her say, "What.... WHAT?... What are you saying.... No... NO NO NO!!!!" Then she starts balling her eyes out.

And I'm like, "What's going on?"

She tells me it's her father on the phone. Her brother just died. His roommates found him in his apartment lying on the bathroom floor. They called 911 but apparently he was already dead. [A few weeks later they figured out the cause. He worked in a nursery and had been administering bug poison to the plants all day and had gotten too much of it into his own system and it killed him.]

But here I was. It was like a two year courtship leading up to the exact moment of me taking her virginity, when suddenly death calls on the phone.

Talk about breaking the mood. It was such a bad feeling for me. I can't imagine how bad it was for her. We never got together again. As if losing her virginity, and sex, and a relationship with me, was forever tied to her brother's death. And it was insurmountable.

She could have been the one for me. But we never got to find out.

That is without a doubt the worst case scenario to ever face..

[Cervino]

I just read this thread and it prompted a deeply repressed memory to surface.
More years ago than I like to admit to, I was working at a large clothes shop - C&A - in London. This was a six-month placement as part of a business course. Met a very sweet young lady there, student like myself and we got on fine.
We had a few evening dates and then I asked her out - all day -on Sunday. The day came and off we went in my little convertible car. Sunny day, mid-summer, what could be better?
Out in the country, we stopped in a leafy glade and got to the clothes off stage quite quickly and happily.
I stuck it in her and we shagged away very pleasantly. Then we changed positions and she knelt on the travel rug spread out on the grass and I glanced at my dick before grabbing her hips.
Red. Yeuch.Yeuch. Yeuch.
I know there are some men who like the red sauce. I don't.
I had to explain to her why I couldn't carry on. It was the most mortifying moment of my life. I could not find anywhere to look or think of to take the thought away as she wiped herself up and put a tampax in. It was all over my hands and the travel rug as well. Vile.
She was more than embarrassed and just sat with her head in her hands all the way back. Said nothing. Never dated her again.

[sooty]

[QUOTE=Leviticus59;1682615]I wholeheartedly agree with DR . . .
Since this thread is turning into a therapy session (as opposed to the normal "hot story" thread) I'm gonna say this-- I suspect that many of you guys complaining about bad/no sex in your marriage suffer from the classic "Nice Guy" syndrome. I myself am a recovering "Nice Guy," and can commiserate with what some of you are saying, on this thread and the one from a few months ago.

I heartily recommend the book "No More Mr. Nice Guy" by Dr. Robert Glover. The chances are good that if you're willing to put up with practically non-existent, awful sex you'll be reading all about yourself in his book. He explains it all very well, and also how to get the sex you want."

I have spent(wasted?) many hours on OCC and after reading the above post I went to Amazon and ordered this book as it is not available in Australia but it only took about 2 or 3 weeks to arrive by normal mail. I have just finished reading it and can highly recommend it for any "nice" guys out there who are living lives below what they want not only in the sex department but in all aspects of their lives. Yes I could see myself in so much of what the author describes and the power to change it lies within us not our partners who give terrible sex. It is not an expensive book so don't delay, to read this you must be online so take the first step and order the book.

[DevilGrrl]

For me, it was one night when I was out at a club. I am mostly a one person type of girl, preferring a relationship. But when I am single, I often get a little wild and really play the field.

I had met this chick, and she was really hot. long red hair, and this really short slinky blue dress that would let her butt poke out whenever she would turn around while we were dancing. After a couple of hours of dancing, things were getting ready to close up and we had both had quite a bit to drink, so we headed off in a taxi to her motel.

The had told me she had never been with another girl, but she wanted me too. we were getting really engaged in the taxi (and giving the driver a good show in the mirror I am sure), and within minutes of entering her room we were on the bed and I had my fingers and lips will occupied.

I was feasting on her pussy and had both hands filled with her breasts, and she was about to have her first orgasm by another girl, when I heard this "URP" noise. Looking up into her face, I saw her gulp, then suddenly spew a load of vomit straight up, landing on her face, then down her chest covering her tits and my hands.

Ewwwww! I let myself flow backwards out of bed, and sat on the floor at the foot of it as she continued to be sick for another couple of minutes. I went into the bathroom and washed my hand off from her puke, then wet a towel and brought it in to her and helped her clean up. Thankfully there was another bed so after getting her in the shower and all cleaned up I helped her crawl into it, and she was unconscious almost as soon as her head hit the pillow.

I stood there for about a couple of minutes, this was definitely not what I was expecting that night. So I cleaned myself up, got dressed, and called a taxi to take me home.

In the last 2 years I have looked for her several times, but never any luck. But by far that stands out as my worst experience.

[Everard]

My worst experience was with a girl called Lynda (yes, with a 'y', what can you say about a woman who can't even spell her own name?). She was awful in bed, all she cared about was her own pleasure, whatever poor sod of a man she was with at the time, just didn't matter.

Being a few years her junior, I had that problem quite a few young guys have, not being able to last that long. Lynda thought she could cure that by shouting "DON'T YOU DARE CUM!!!!!" at the top of her voice. You can just imagine what effect that had!