What was your most disappointing sexual encounter

Disappointment is the product of excessive expectations. As my sexual experience has increased, I have had more realistic expectations, and consequently far fewer disappointments over time.

The most disappointing sexual encounter I ever had was my first experience with coitus. She was also a virgin, and we were both greatly disappointed by the experience. We each had a different set of expectations, as we discussed later, with a few common elements. The reality wasn't magical, explosive, or orgasmic. Our arousal and excitement prior to penetration was intense. The act itself - mutually unsatisfying. Seeing the disappointment on her face, and despite repositioning, there was little penile-vaginal sensation or stimulation for either of us.

Once I lost the small erection I'd had earlier, and after my penis shriveled to almost nothing, we didn't give up. We should have. Our continuing efforts to get and keep me in her, in order for either of us to derive some physical pleasure from this act we'd so looked forward to proved as impossible as keeping a condom on me. The condoms we had were too large and loose on my erection. On my tiny flaccid member, there was no hope of keeping it from slipping off unless I held it on with my fingers, nor of achieving any penetration at all with it that size.

No, the experience wasn't accompanied by the fireworks expected from our earlier passionate kissing. I'm sure she regretted the lace camisole and panties she'd bought in anticipation of us doing the deed.

 

Me too! I distinctly remember thinking, once I was in, this is it? I can feel more if I do it....but it could have been the condom plus my high expectations and general teen cluelessness. BUT, after the initial round of 'oh I guess we did it', the follow-up session turned out to be one of the hotter moments that I remember....crazy hot and risky, but luckily I got to my senses in time to put another condom on to finish out the night. Shit, that was all we would have needed was to get pregnant on our first time.....too bad she turned out to be such a head case.

 

When it's so small you can barely feel it and the fact that it keeps slipping out every time you pull up to bounce on it...

 

You're a sad person..... It's a huge thing to accomplish dropping weight like that and you want to judge her based on excess skin that she had. Do you realize how much that surgery cost to have that skin removed?

Walk a mile in someone's shoes before you judge them. Douche

 

I believe you got me all wrong. The post asked about a "disappointing sexual encounter." That was it for me. It may not be for another person but it was something I was not use to. I did not shame her which I stated in my comment. I do understand how difficult it is for some people to lose weight and for that I applaud her efforts. But the experience itself was something I was not expecting and therefore it was disappointing for me.

So if you can explain to me what it was that I said that offended you, please feel free to do so.

Actually I have had the opposite experience. I was with a girl that was a bit over weight and expected the obvious that I have experienced with over weight girls in the past. However when we got down to it she was like a wild cat in bed. Her excess weight made my expectations completely wrong.

She jumped around and had more energy that I have ever experienced even with thinner girls. She was very solid and strong. She didn't just lay there like a log which was what I expected. So one's expectations can go in either direction. I do not put people down for any reason. We are all a bit different but very equal.

 

there's really no point... I couldn't have said it any clearer. Maybe once you're overweight and you struggle with it, you would understand what it's like. But I bet you're one of those people that has "high metabolism" and can eat whatever they want without ever gaining a pound.

 

Actually no, I am not one of those people. I have been on the Keto diet for 8 years. This diet takes all of the self control a human being can muster to stay within the boundaries of 30 carbs per day.

 

Try this. no sugar period, no grains, no pasta, no pizza, no booze, no bread, no spaghetti, no BBQ sauces, no preservatives, and that's just the beginning. Give it a try.

 

Oh yes and fast for 16 hours every day.

 

Yes being thin takes some work.

 

I do believe arguing with this one is like wrestling a pig in the mud. After a while you realize the pig likes it.

 

My most disappointing or more so shameful was not one time but probably over a 100 times with my ex long term gf. When we first got together it was pretty awesome. A year and half in then U started to experience premature ejaculation with her. It got worse and worse and I would be constantly worried about it before sex and ashamed after. The last 6 months together, I would cum my full load as she would slide down my shaft very first time. All her friends knew my problem and she ended up leaving me for one of my mates. After her I started fucking a woman I didn't have feelings for and then couldn't cum. With my current wife, all good.

 

Oh no doubt...this time:
I was at a New Years Eve Party, met a girl there and we hit it off. It turned out she was best friends of the couple that lived there.
After everyone left, the couple went to bed and we stayed in the living room.
Got naked... started having sex, and this gal just laid there. I mean no movement of any kind. Not even expressions.
I couldn't finish. My cock actually lost it's erection while inside of her. I felt like I was raping her.
And now for the weird part... she contacted me about a week later and asked if I wanted to go out sometime... uh...no.