What was your most disappointing sexual encounter

You’re a good man

 

You definitely have to vibe with someone to really enjoy it.

 

I love them to thrust onto me, get a bit noisy, and fuck me as hard a s I fuck her. Damn. So long ago

 

I always try to "fuck back"

 

A month or so after my wife threw me out, a good friend told me I had to get laid to get over being thrown out. He set me up with a date to fuck and invited me over to his place to meet her. She wasn't my type, but hey, I was horny and as my friend said, I needed to get laid.

After we had a couple of drinks, my date stated, "I'm ready to fuck you. Let's go to my apartment."

We undressed when we got to her bedroom and began kissing lying together on the bed. My cock sprang to life quickly. I began fingering her and soon went down to give her an oral orgasm, but as soon as my tongue licked her vulva, I was disgusted by a horrible smell and taste. She had sprayed her pussy with FDS, a feminine deodorant spray. That stench immediately broke my mood, but we fucked anyway. I never saw her again.

 

Good girl. It makes such a difference when she fucks me as much as I fuck her.

 

I had one gf that upon the first time for us was worried I was too big, but I knew I wasn't too big for anyone. But she had just divorced from a 1 year marriage at age 18 and told me he was very small cocked, so I said well mine is really average, but she said since she had been used to that small cock that it just looked huge, I do have excellent girth. and then she told me I had to go slow to start. So that worked just fine ...on the outside of her vagina she was dry but once she gave me the ok to go deeper I discovered quite a deep well of slick wet pussy juice and I started pulling some of it out and soon she was dripping on the bed making a big wet spot. And the whole time I fucked with her she was that way dry on the outside and flowing deeper in...but since she had got used to my size I could go plumb it out to the outside sooner in the fuck like 2 strokes almost every time after that. So the next time you meet a girl horrified by your cock you might say something like, ok, lay down here with me and Ill hold you and we will talk and then while you are holding and talking and maybe your roaring hard on tapping the back of her thigh intermittently. She will feel like she isn't being rushed into anything BIG, get it? Big. Then in a bit ask her if she would like to try slowly, and let her know you will stop anytime she says. Then see what happens, or, just see what happens.

 

As I man you gotta be prepared for this. Lol it feels amazing

 

One older woman I had sex with a few times, I used to go down and lick her out. Once I wanted to get her to fever pitch by spending a while licking her and sucking her clit. She had peed and hadn't cleaned up properly and she had thick pubes,so and I had piss flavoured licking out. I said nothing and worked through it, and it was yuck at first but she flushed out as she got juicier. She got vocal as she got hornier. "Ooh, I'll get you back. Come on. Fuck me hard. Forget the condom. I want your cock in me". I got on and slipped in bareback for the first time with her. "OOh, that feels better." So I said nothing about the piss flavoured lick-out and it paid off with a wild fuck.

 

Amazing. Personally, I wouldn’t mind the piss but it sounds like it ended up great for you.

 

I was dating this beautiful woman (me 45, her 35). She was every guy's dream as she had been a major college cheerleader. Our intelligence and educational levels were equal. She caught on to play on words jokes. We liked the same music. It was a perfect match......except she never really got into sex. The instance I am about to relate is still painful. We had been going at it half an hour when she said the words that instantly changed stiff willy to a flower: "Are you almost done?" Goddamn right. Got up and got dressed. Would have gone home except we were at my house.

 

I can think of a couple of experiences.

A long time ago in my 20s, I met this girl in a club who was a model. Really pretty. We went back to her place that night and had sex. It was fun. We make plans to go away the following weekend to a ski resort that is known to be romantic. On the 3-hour drive, she tells me about an ex who turned out to be a drug dealer that was upset after she broke up with him. She tells me how he basically kidnapped her, injected her with drugs and was eventually arrested. When we get to the hotel she wants to have sex. I wasn't really in the mood after her story, but I was young and did it anyway. The whole time I'm thinking about omg, I had sex with her unprotected last week. This was at the height of HIV paranoia. Anyway, we're having sex (no condom again) and I was incredibly mentally distracted. She kept yelling at me to go harder and faster. I just couldn't get into it. It was probably her most disappointing sex encounter. Mine, too, I guess from my expectations. I got an STD test immediately that Monday. Luckily it was clean.

Another time was after my ex and I broke up. Her sister was gorgeous and had a thing for me. She invited me to fly down for the weekend. I thought well the sister is hot and this will make my ex jealous, so I flew to see her. We went out and ended up back in my hotel room. The sister tells me, "I only like sex from behind. It's the only way I can get off and my boyfriend is too small, so our sex isn't great. I want to fuck me in doggy style. I'm thinking, um, sure no problem. Then she says she has a thing about being touched. She doesn't like kissing or being touched anywhere on her body. Now I'm thinking, wtf. My ex was a total kinky freak and her sister was the complete opposite. I'm pretty kinky myself, so this is going to suck, but being a guy, I decide to fuck her because she's hot and it will drive my ex crazy. I started fucking her, but it sucked. I just felt so inhibited and I couldn't do anything I really wanted. I did not enjoy it at all. It was the worst sex since that first that encounter I wrote about above. She leaves at about 3am and my ex calls to ask if I'm with her sister. I said, he just left a few minutes ago. She asked if I fucked her sister and I said yes, but that it was terrible. My ex got pretty mad, but ended up coming over to my hotel and we had some crazy fight/make-up sex. So technically, I had both sisters that night. That was the last time I had sex with either one. I just moved on to some other girl.

 

That would have to be this girl who was talking all kinds of shit about how good she was in bed, how she could suck dick and make a guy cum fast so she could swallow and, of course, she could go all night long. I got to get in those panties and (1) she couldn't suck dick as well as she said she could, (2) she was hollering and screaming like I was murdering her when I tried to eat her and (3) when I did get my dick in her, she was acting up so bad that I pulled out and started getting dressed. She had wanted to know why I was leaving, and I told her that she wasn't living up to her own hype and she might want to rethink that shit because she was going to run into a guy who would want to hold her to the hype and it was going to suck to be her when she wasn't all that.

Such a pretty girl but one who's skills weren't as advertised. She was one of the females who had me rethinking a lot of things about sex with them...

 

I guess I've been pretty lucky to have rarely been disappointed with a sexual partner, but I do remember two different encounters. One with a guy and one with a girl. The girl I met at a party right out of high school and provided her a ride home. She said she needed to get up early for work and if I'd leave the party early to take her home, she will provide a great blow job for my efforts. OK, we get to her apartment, in my truck and she reaches over and opens my pants and starts to suck my dick. She was terrible, just sliding it in and out of her mouth, not really sucking on it and sliding her teeth against my shaft. I asked her to stop as it was not enjoyable at all. The guy I met through a Craig's List Ad looking for his first blow job from a guy. I arrived at his house and sat on his living room couch with him and said, you want a blow job right here? OK, her removes his pants as I get on my knees on the floor and start sucking his thick cock, I was liking it as it was beginning to grow inside my mouth but after two minutes, he pulled his dick out of my mouth and put his pants back on and said: "This won't work" and I left.

 

I met this woman I chatted with on a dating site, she came to my motel room when I needed to be somewhere close enough to where she lived.
Sadly as soon as she walked in I sensed the vibe was not there between us.
I gave it a try thinking it could change once things got going. Nope. It was just a little release for both of us, we just went through the motions.

 

My most disappointing would only be times I didn't have sex when I could have.

 

Me and Marie met a swingers couple in a hotel room. Me and the wife had sex on one bed while Marie and the husband had sex in various positions throughout the hotel room. They had sex on the bed, the furniture and on the floor. At one time me and the wife stopped and watched her husband and Marie go at it. I thought Marie had a great time with the husband. When we were on our way home Marie said she was glad it was over. She told me she hated having sex with him. His dick was small and was jackhammering her the whole time. She said she saw I was having a great time with the wife and she didn’t want to mess that up. She was faking it the whole time.

I immediately became irate with her. I wish she would’ve said something. We had a long talk after that. That was a terrible night for us. I was more disappointed in myself than with Marie. That’s when we established a safe word in case we find ourselves in that same predicament.

 

Safe word…”Oh my!” ;-)

 

I can't say that I have had a disappointing sexual encounter. I cherish them all!