I had known Sheila for as long as I can remember, she lived next door to my parents, she was never one of my regular fantasies, though undoubtedly I did think of her from time to time when ************ and imagining being seduced.
I was 28 when we had sex, which would make Sheila 56.
The circumstances were that she had just gone through a divorce caused by her husband absconding with a woman half his age, so I guess she was feeling unwanted and unattractive.
I was home visiting my parents and found myself home alone on this particular day as they were both out at work, I don't smoke regularly, but this one of those times that I just fancied a cigarette. I was sitting in the conservatory having a smoke when Sheila arrived, she made some comment about how my parents would not be happy at smoking in their house, I agreed and said that was why I was using the conservatory so that I could open it up and get rid of the evidence. I offered her a cigarette as I knew she smoked.
We sat and smoked and generally chatted, she asked me if I was dating, I said there was nothing serious, I knew about her divorce and told her I thought her husband had behaved like an idiot, especially as she was very attractive, why I said that I don't know, it was true but not the sort of thing one would say to their mothers friend, whatever the reason I am glad I did say it, given what it led to.
Sheila said she could not be attractive or he wouldn't have left, and in any case she couldn't compete with younger girls, I then told her that I preferred women who were more mature.
There was a change to the atmosphere at this point, Sheila was looking at me in a subtly different manner, I wondered if she was wondering the same as me, that is say was the other person up for a roll in the sack.
I confessed to her that I preferred women of her age to those my own age.
Sheila looked at me, she went to speak, then stopped herself, then she finally spoke and asked me to take her upstairs.
Once in my bedroom, we kissed and undressed. Her body was in good shape and the sex was good. I went down on her, she was clearly uncertain about sucking my penis, of course I said she didn't have to, she gave it a few licks, but it was clear that oral sex was not in her repertoire. I sucked on her breasts and she fondled my hard penis, then I slid inside her in a missionary position, looking down at the face of my mothers friend as I screwed her was, I have to admit, a turn on. She was not quiet, but not loud either, after a few minutes of the missionary, she asked to go on top, so I lay on my back and watched as she lowered herself onto me. It felt really good to play with her breasts as she rode me to her ******, soon after that she completed the ride by bringing me to mine.
We never screwed again, but she did start to date a younger man, so I guess I must have given her back her sexual confidence.
MiddleAgedToyboy MiddleAgedToyboy
46-50, M
1 Response Aug 16, 2010

Great story! I'd love to find an older woman for myself. It's always been a fansasy of mine!