Like many on here, the one that sticks out in my memory was an accident.
I was 23, she was 30, I actually picked her up at work, she was playing on one of the tables I was dealing at, a few drinks after work, a long conversation and it was back to her place.
At this point, I should point out that she was way out of my league, i'm a tall, kinda scruffy 23 year old, she is a very attractive 30 year old with long blond hair and a body to die for, what the hell she saw in me I have no idea, but hey, not complaining.
Over drinks the discussion of course turned to sex, she had been married for a few years to a conservative type of guy, lights out etc, I made it clear that that was not my thing, if we were going to make love, then fine, if we were going to f**k then game on (damn how I miss being in my early 20's), she was fine with that, but did say that she had tried anal with her ex and had stopped before it went to far because it hurt, okay i'm cool with that, as long as I know.
So back to her place, a few more drinks, then the clothes start coming off. Yeah I am way out of my league with this one, what a body.
So we are messing around for a while, her on top, on her side, then into doggy, at this point I am pretty much wasted, to many drinks, in my mind I am a stud, truth is it was probably a disjointed mess, but hey, she seemed to be enjoying it and I know I was, and then it happened.
Like others, pull back and go for the power stroke, slip out and wrong hole it, i'm not a huge guy, right around 8", but a little on the thick side, she screamed, face in the pillow and I stopped, first thought through my mind, I am here with a stunning woman who is screwing my brains out and I just did the one thing she said no way to, s**t.
She takes her head out of the pillow, looks at me and says "is that what I have been saying no to, f**k me now"
I looked at her, said sorry, then said "let me pull out and go find a clean rubber"
She said "are you stupid, leave it there and f**k me"
Over the next 10-15 minutes I pounded her, she must have cum 5-6 times, I finally cum, we lay for a while, then off to the shower.
I again say sorry, it was an accident, she is giving me the dumb ass look, then tells me that she has never orgasmed like that before and she wants it again when I am ready. I ended up f***ing her for the next 2 days, calling off sick at work, it was insane.
This went on for about a month, then one night she drops the great news on me, she was actually still married and hubby was coming home in a few days, so thanks but it was over
I really didn't care, the more I got to know her, the more it was clear that she wasn't my type, but damn the sex was so good, I explained this to her and offered to be the man on the side, but she was having none of it.