The oldest women I have been involved with have included one 39 year old woman when I was myself 21 or 22, and a 41 year old when I was myself 24. The 39 year old I met online and must admit, part of the reason I hooked up with her was just for the experience of being with an older woman, something I hadn't done before. We met once, had dinner and had sex. She wasn't very attractive and overall it wasn't a very positive experience for me, in spite of her being very sexually responsive, which I normally like. I don't know what she viewed me as... but she was just getting out of a bad marriage, seperated but not yet divorced, and I was the first guy she had had sex with since she had stopped having sex with her husband. She also told me I was the youngest man she had ever been with, in terms of the age discrepancy. I think her reasons for going in were about the same as mine- just trying to have some fun and experience something new.

The 41 year old I liked a lot more, she was much more attractive and more fun to go out with. I believe she liked me as well, but in the end I think her own insecurities about how a younger man might see her (not based on anything I said) led to the relationship never becoming serious or sexual.

Beyond that, I think the oldest woman I've slept with was 32... oldest I've been somewhat involved with beyond sex was 29... oldest I've dated for an extended period of time was 27 or 28... usually I go for younger, including the girl I'm seeing now, who is a lot younger than I am. But my first girlfriend was a bit older than me, the most serious crush of my life was on a girl three years my senior, and ultimately age doesn't matter much to me.

Sorry I didn't have much to actually add to answer the original question.