Worst Sexual Experience?

Sad day..

I had an ongoing flirtation at work with a physician. He was so attractive and I would just lust for him whenever I was in close proximity. It went on for awhile until one night we finally ended up in bed.

I thought it would be the best sex ever. But, I honestly think he thought he was so hot (which he was) that he didn't even have to try in bed (not the case). It was so underwhelming. He just wanted to hammer it in like a jackrabbit.

And, then it was awkward since we worked together. :/

The summer after my freshman year of college I started dating this girl that still lived at home.. She had a nice body and really great tits. So, one night when her parents were out of town she plans this whole evening that ends with her in lingerie in her bedroom. Everything's going great until it comes time for us to fuck. She was so tight that no matter what we tried I could not get it in. After what seemed like an hour, I was dripping sweat and so tired that I finally just gave up.

mustang_driver said:

The summer after my freshman year of college I started dating this girl that still lived at home.. She had a nice body and really great tits. So, one night when her parents were out of town she plans this whole evening that ends with her in lingerie in her bedroom. Everything's going great until it comes time for us to fuck. She was so tight that no matter what we tried I could not get it in. After what seemed like an hour, I was dripping sweat and so tired that I finally just gave up.

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That happened when I took someone's virginity. My god it felt like I was jamming it though a pencil hole... it hurt like fuck and took a good hour or more to get it partially in -- it took another 2 sessions after that before she loosened up down there.

This happened a few months ago. Not a worst experience, but a strange experience for me. Finally managed to take home this hot college hockey player after weeks of flirting and texting. He was very nervous but excited as we entered my house. I decided to get right to it rather than deal with his being so nervous. We started kissing passionately and of course I had to make every first move. To make a long story short. By time I got his pants and underwear down, he was rock hard and flowing, not oozing, precum. I wrapped my hand around his rock hard dick and 3 strokes later, he exploded, shooting ropes of cum all over my chest, my face, my hair, and he even got me in the eye which burned like hell. Of all the partners I've had, I never had a guy cum as much as he did. It was literally all over me. I kept stroking him, but he just started crying while apologizing profusely. I wanted to keep going because I was so wet and turned on. But he just cried and cried as he pulled up his pants and underwear quickly and hurried out of my house. Meanwhile I was left standing there drenched in his cum, with my eye still closed and burning like hell.

hottiebonnie said:

This happened a few months ago. Not a worst experience, but a strange experience for me. Finally managed to take home this hot college hockey player after weeks of flirting and texting. He was very nervous but excited as we entered my house. I decided to get right to it rather than deal with his being so nervous. We started kissing passionately and of course I had to make every first move. To make a long story short. By time I got his pants and underwear down, he was rock hard and flowing, not oozing, precum. I wrapped my hand around his rock hard dick and 3 strokes later, he exploded, shooting ropes of cum all over my chest, my face, my hair, and he even got me in the eye which burned like hell. Of all the partners I've had, I never had a guy cum as much as he did. It was literally all over me. I kept stroking him, but he just started crying while apologizing profusely. I wanted to keep going because I was so wet and turned on. But he just cried and cried as he pulled up his pants and underwear quickly and hurried out of my house. Meanwhile I was left standing there drenched in his cum, with my eye still closed and burning like hell.

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Wow sorry to hear

Dated this girl for a little while in my mid-twenties. She gave the best blowjobs that I have ever had in my life, but she would not sleep with me after we had been drinking, because in her words, "The first time we make love, I want to be completely sober." One night I figure I will just drink water because if she is as skilled with her body as she is with her mouth, it will be total heaven. It works, we go back to her house, after a very heavy make out session, we both are completely naked. I go down on her and she barely moves. "No big deal.", I think. Some girls are really not into that. So I move up and slide into her. No noises, her arms don't move, and her legs don't move. Nothing. The entire time I am fucking her, there is no signs of life from her. Not long after, we broke up because she cheated on me. Talked to the guy she cheated on me with, he said pretty much the same thing about sleeping with her.

Terrible sex life

Wife has lost interest after 10 years. We both let ourselves go so I cheat

This is very easy. Wife got an iud for birth control. A piece of wire protruded a bit out of her cervix.

Yep, stabbed the head of my cock. Talk about a quick let down.

I bled a little.

And made an appointment for a vasectomy

I had to think hard about any sexual experience that wasn't at least "good", if not great, and had to backtrack through anyone and everyone with whom I've ever had sex.

....and then, I remembered this one. After a recent breakup, I was at a party at a friends house and a girl who had almost been stalking me for years was there. I had never been interested and had been basically been unavailable, with a girlfriend, for as long as I'd known her. She was a bit heavy (with big tits), though not unattractive, but I felt a little too wild (and promiscuous) to be my type. She, along with most of the other people, were already REALLY drunk when I arrived.

I had just finished a major restoration on the Austin-Healey Sprite Mark III I had at the time and a bunch of the guys wanted to see it so we went outside to take a look and she followed us. When we were getting ready to go back inside she asked if she could go for a ride. I said "Yes", and I have to admit that the thought of a different kind of "ride" crossed my mind.

It was late in the afternoon, almost evening, in August with outside temperatures in the high 90s to low 100s. People at the party had been swimming and all she was wearing was a two piece swimsuit and cotton gauze type coverup. We got in the Sprite, top down, and I headed for a curvy road through the foothills where I could let my little sports car shine.

Before we could get out of town, and while still driving on city streets, I looked over just as she pulled the coverup over her head and released her big boobs from the confines of her swimsuit top. It was then that I realized that she was more drunk than I had thought and she merely laughed when I asked her to cover up and even flashed her boobs at passing cars. We were almost out of town so I expedited my pace to get into the country.

With her yelling and screaming, whooping it up with the wind blowing in her hair, and boobs bouncing and swaying with the bumps and curves in the road, I drove out to a favorite "lover's lane" on top of a hill about ten miles outside of town and parked. We started to make out and I soon had my hands on her boobs, and down the bottom of her suit diddling her clit while she plunged her hand down my jammers swim shorts and, albeit a bit roughly, jerked my dick.

I debated how we should fuck, and considered getting out and laying a blanket I had in the trunk on the ground, but decided to do it doggy style in the car. Heck, it has worked before.

We got naked and I had her kneel on the passengers seat facing the rear with her chest laying on top of the seat back. As she had a hard time maneuvering, and seemed totally uncoordinated, I began to realize how totally sauced she was. I felt almost like Thomas Hulce as "Pinto" in Animal House with the devil on one shoulder whispering, "Fuck her. Fuck her brains out," in one ear and an angel whispering "If you lay one finger on that helpless girl you'll despise yourself for ever..." in the other. I chose the devil but it didn't work out.

I moved in behind her, my knees outside of hers on the seat, and began to screw her in this modified doggie style but it just wasn't working. There was no rhythm, no chemistry between us, and she was so drunk that she just didn't seem capable of helping out. It was just wet, sloppy, and loose.

I suggested that she grab onto the roll bar for support, hoping it would make it work for us. Just as she started to reach up I heard her gag a few times, as if trying to hold it back, before vomiting on my convertible top and into the space between the seat back and the boot....of my newly restored and detailed car!!

Instantly FLACCID. Mood gone. Now only in clean up mode and she had turned into a semi-conscious dead weight.

I got dressed and then turned her around in the seat. She was too far gone to even lift up her butt so I could put her suit bottoms back on so just pulled the coverup over her head and slipped her arms through the straps. I then strapped her into her seat belt and headed back to town.

When I got back, and asked for help getting her out of the car, I was informed that it wasn't just alcohol but that she'd also taken a Quaalude (a big thing back then). Now they tell me. It all made sense now. I wondered how it seemed like she was getting drunker while we weren't drinking.

In any event, we never did hook up for real and the incident was never mentioned between us. Some things are best unspoken...I guess.

Melody_lane said:

I had an ongoing flirtation at work with a physician. He was so attractive and I would just lust for him whenever I was in close proximity. It went on for awhile until one night we finally ended up in bed.

I thought it would be the best sex ever. But, I honestly think he thought he was so hot (which he was) that he didn't even have to try in bed (not the case). It was so underwhelming. He just wanted to hammer it in like a jackrabbit.

And, then it was awkward since we worked together. :/

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Had similar in my youth. Friends ex-GF.

We'd flirted etc for months, she was hot but classless.

When we eventually got down to it, she was awful in bed. Selfish and arrogant.

...........

There was a woman I played with briefly who said she was this amazing submissive, and a blowjob queen. Her cock sucking was just okay, she could take a spanking okay, but that was the extent of her submissiveness, and would just lie there during sex. Also, her twat smelled like something died in it. I didn’t like going down on her, and it took forever to wash the smell off my hands. But she was sweet enough, so I kept playing.

Eventually she got all the wanted from me, blocked me on social media, and started spreading rumors about me. This was years ago, but it still bothers me that I was taken in by a manipulative little bitch.

Two spring to mind, the first was in my late teens. Cute, hot little blonde, classless but screamed "I fuck well". Weeks of texting etc. we get down to it.

Cowgirl only, to suit her, silent, she lasted minutes. Done.

Probably the worst ever.


Secondly, my wife. Both a bit tipsy, horny, she went on top. Rare In itself. She's not small. Gets carried away, goes all the way up and off before slamming down. Hits my cock at a weird angle, actually head it "snap" and make a loud pop.

I'm in agony, tears in my eyes, winded. Takes her a minute or two to understand that I'm serious. Tries to carry on.


Hurt like hell for over 2 weeks.

Started having sex with a girl, everything good and she starts to orgasm, when she's on the verge of cuming, she chokes with the chewing gum that I didn't notice she was still chewing. I thought she might die

Another time, same girl, 3 orgasms in a row and at the end of the 3rd orgasm, she fainted. Didn't know what to do so I kept going hoping she would come back to senses quickly and luckily she did

Met a woman on a business trip and took her back to my hotel room. I undressed and lay on the bed while she went to the bathroom. She walked into the room naked and had an OK body but the biggest bush I have ever seen. I dont mind hairy too much and thought it might be a novelty to go down on her. Big mistake. She had the worst smelling pussy I have ever encountered. I tried my best to not embarrass her and get down to it but the cloying smell in my nose was just too much and I could not get hard for love or money. I had to claim a headache to get her to leave. After that I routinely suggest a nice shower before we get down to anything.

I met a woman online. Flirted for weeks, and she finally came over one day in the summer. I was about an hour from where she lived, but she had business in my town. She didn’t wash up at all before we got down to it and she begged me to down on her, which I normally love. She was so sweaty and had such a smell that I half-heartedly lasted about two minutes of that, after which we had mediocre sex and she left.

I’ll also rat myself out on one. I was talking with a girl while drinking and jerking it. Convinced her to come over, but didn’t finish beforehand, like an idiot. We started making out, got undressed, I got her wet and she got on her knees and barely started working on me before I came all over her face and tits. She looked at me disappointedly and said “That’s it? Really?” I felt terrible and offered to get her off, but she refused and left. Thinking back, I’m not even sure she cleaned up first, she was in such a hurry.

I just posted this in another thread a few minutes ago, but it applies here. This happened a little over a year and a half ago.

I had recently stopped seeing someone after eight years with whom I had an amazing sex life except she would not give head. Ever. At all. I met this woman via a friend of a friend and we flirted some online and finally decided to get together one night. I'd told her about how I'd not had a blowjob in over eight years (the time before the last gf was a long dry spell in addition to her not being into giving head. She told me repeatedly she loved to suck dick and was very good at it and couldn't wait to go down on me.

So the "Big Night" arrived and we ate dinner then fooled around some, with both of us dying to get naked and down to business. She asked me to tell her what I liked when receiving head and I told her I enjoyed the head and my balls being sucked most of all as well as switching back and forth from her mouth to her hand. Teasing my frenulum with her finger or tongue was also very fun. But when she started I had to ask her to literally quit biting my dick and she tried to argue with me that every man she'd ever been with before was into that and I should be, too. When she moved to my balls, it was the same thing all over again. I don't mind a playful tease with someone's teeth but she was fucking chewing on me and it was very painful.

I finally got her to the point where she wasn't causing me any more pain, and then the moment my precum hit her tongue she began gagging and acting like she was about to vomit. I asked her if I tasted bad and she told me I didn't. I also told her that if she wanted to stop I was fine with it because I didn't want to make her feel uncomfortable. But she insisted on going back and her reaction every few seconds was as if she were fighting off the urge to puke. I suggested she just finish me off with a handjob and when I came in the palm of her hand she began to freak out, almost sobbing. She got up and ran to the bathroom with her arm extended straight out, keeping her hand as far away from her body as she could. I could hear her talking to herself while taking several minutes to wash her hands.

That was the only time we've ever been together sexually and she left right after. I've only seen her twice since then. I found out a month ago she was telling her friends she and I were fuck buddies (the blowjob was the only encounter we had). Also, since that night, she has displayed some stalker-type behavior, like reading my FB posts and if I mentioned being hungry or thirsty she'd text me later to tell me she'd left something on my carport for me (usually whatever food I had mentioned I was in the mood for or my favorite soft drink). She also told me once she tried to burn down her house with her husband (of only four days) inside. It turned out he wasn't home and she was mad she'd burned down her house for nothing. I thought she was kidding, but she wasn't.

In retrospect I should have listened to my dog. He has never once growled or acted upset if someone came over until that night. In fact, he generally ignores everyone after an initial greeting at the door. He planted himself in front of her and began snarling and baring his teeth. He was literally warning her to not enter the house. I got him to at least step out of her way so she could come in. Last Christmas she stopped by to say "Hi" but I had to talk to her outside. As soon as he recognized her he began the growling and teeth-baring all over again. I wasn't going to risk him biting her and then having to make a trip to the ER.