The oldest woman I have had sex with is 58, but that is not that old at all. However, your post made me think of the biggest age difference in terms of sex. I have just remembered a woman I had sex with when I was 23. She used to work as a cleaner in a medical centre where a friend of mine was working as a nurse. A couple of months after he starting working there, he arranged a birthday party and invited some of the staff members. She was about to turn 48 and she was divorced, but with a 14-year-old ....... My friend and many of the guests got a bit ...... but she was sober, because she had to drive back and pick up her ...... from her ex. We started to chat and had a good conversation. When she was about to leave, I asked for her phone number, but I did not call her. Around a week later, my friend told me she had been asking him about me and I told him that we had had a very good conversation. This led me to call her one day and she told me that she was off on a Thursday. I told her that we could meet after my university classes on that day and have lunch. She accepted. When we met, we had a good lunch and I could not take my eyes off her boobs. However, she seemed not to be interested in anything sexual. After lunch, I invited her to have a coffee and we went to a local café. I suddenly decided to ask her whether she would be interested in having sex with me. I did it writing the question on a small piece of paper. "Would you like to have sex with me. If so, just smile or laugh. Otherwise, return this piece of paper, so that I can use it somewhere else". She read it and started to laugh. I asked her: "Does it mean "yes?" And she said: "yes, why not... but we cannot go to my place today..."
We went to her car and I told her to go to a plantation area close to the sea, so we could hide. We had sex in her small car. I remember sucking her big boobs and how passionate she was while she was riding me. She loved it.
A couple of months late, I visited her one morning. She was wearing no underwear. It was a great fuck again but the condom broke and we did not have more condoms. I finished on her face.
Shortly after, she started a relationship with an older man, so we never had sex again.