What was your most disappointing sexual encounter

One of the first times I was receiving oral sex the girl decided to bite... and I mean -bite- the head of my penis. Needless to say, that whole session was instantly ruined at the truly horrible pain of that happening...

 

One of least memorable times I had sex with my ex. Missionary style, I was in to it, building to the big finish...she says “what are we going to get your mother for Christmas”.

 

Any pussy that smells!

 

Never made one limp (pretty funny), but did give one a sore tail bone once.
That from spending the night on a big rock next to a waterfall on the river.

 

this girl i dated from Argentina, was super sexy, nice bubble butt, large implants, long black hair, olive skin.... absolutely gorgeous in my eyes.... everybody was always hitting on her n just everyone wanted to fuck her... she would never date anybody though n she would always talk about the crazy sex she was into and her amazing blowjob skills and how wild she was.... finally after working together for years we started dating... her body was amazing but all she did was lay on her back, she didn't like to get head or give it, i wasn't allowed to cum in her i had to pull out n cum in her hand... it was the most boring girl i've ever been with... if she wasn't a sexy looking as she was i don't think i'd even get hard cause me n my dick got bored with that shit quick

 

I don't remember some of the night, I had "whiskey Dick" and ended up watching the guy fucking my gf.
All I could do that night was suck his cock after he finished in her pussy. I slowed down the drinking.
The most disappointing was not being able to cum my wife and one of her girlfriends.
Difficult to enjoy watching two beautiful women going at it when you can't join in or jerk off