What was your most disappointing sexual encounter

A lot to chose from actually. Right up there challenging for the mumber one spot was when I thought I was going to engage in my first mff threesome. It was all going swimmingly except the two girls involved were just pranking me. They managed to create a situation where they hadnt even gotten down to their underwear and I was fully naked before they started laughing and informed me of their plot.
It as much more embarrassing because I have a very tiny penis ( which didnt go unnoticed and was definitely commented on)

 

The last time I had sex with my wife.

 

:-(

 

I don't know if I posted this before or maybe in another thread, but mine had to be the very first time I had intercourse. I was in the early stages of puberty and the girl that I fucked was a nymphomaniac who was into "deflowering" virgin boys. We went to her house because nobody was home. We retired to her bedroom and stripped. My cock was already hard from the excitement of having actual sex for the first time. She laid on her bed and I crawled on top of her. I knew nothing about foreplay so my plan was to get right to it. I slid my hand between her legs, fumbled around and finally managed to slip a couple fingers in her pussy. It felt amazing, all soft, moist and wet. Now that I had located my target I moved on to the actual "act". I reached down and grabbed my hard cock to slide it in. Unfortunately I missed and slid it underneath her and between her as cheeks. After noticing my dilemma she offered to help. She reached between her legs, grabbed my cock and guided into her soft, silky, wet pussy. After what seemed to me like an eternity of bliss, my cock exploded inside her and I filled her with my cum. I will be the first one to admit that at that age I was far from being a master at fucking. In fact it was awkward, clumsy, way too quick and embarrassing for me. Knowing her reputation I'm sure this happened to her quite often, but it was a sheer disaster to me. Thank god through lots of "practice" I have gotten much, much better at it. My first attempt at cunnilingus wasn't a great milestone either, but the women that I have been with think I learned my lesson very well!!!

 

I was with a girl one time, and she started saying she doesn't feel right doing this when love was not involved. I asked her if she wanted me to stop. Thank goodness she replied not if I was enjoying it. I don't think she wanted me to think she was a bad girl. And if I wasn't enjoying it that would have been a first.

 

:-(

 

Probably snd older co worker. There was some flirting going on for a few weeks and we finally hooked up in his car after work. Let’s just say his only focus was on him cumming. Defiantly left alot to be desired.

 

That sucks

 

Darn old man! He missed the boat!!

 

My wife and I had a couple in our home once. We swapped. My wife went down on him. He busted in about 15 seconds. His wife only wanted me to cum in her for the vitamin aspect of cum. She laid there like a limp noddle. I was so turned off by this, I got up and didn’t finish in her. This was a weird woman/couple.

 

My most disappointing time was my first time, just because I was nervous and could not get completely hard.
I made up for it though.

 

This was 40 years ago but I remember it like it was yesterday. My relationship partner, N, was a beautiful woman of 35. She had been a cheerleader at a major university then married and divorced. I met her former husband at a company gathering. He was with his gf, a mousey. 6 on a scale of 10 gal, a real step down. Later when the newness of our relationship wore off, it was apparent why they had divorced. She had little sex drive. Our sessions were me enjoying myself, her enduring it. This was a Sunday afternoon. She said the following words which instantly caused my erection to deflate: Are you almost done? Yes, at that exact instant. End of that activity. We were together for 3 1/2 years in which time we took a three day sexual relationship seminar and saw a sex counselor. Nope, she just didn't have it. We were a great match in all other ways but the difference in sex desire finally ended the relationship. In retrospect, she would have been the perfect partner in an open relationship. Once just before I was to take a trip to the Midwest, she told me that I could fool around if I wanted as she didn't know about it. I wasn't sophisticated/experienced enough to go down that road. N. was a learning experience for me. Since then if a woman wasn't wildly sexual, I moved on.