How old was the oldest woman you have been with and how old would you go?

[SofiaSexy]

70 years very old woman

[piecenick]

66, everyday she gets older, so check with me next week. Those orgasms keep rolling along.

[ev1l0ne]

For me, she was nine years older than me. I was 17 and going into the Navy.

So as a going away present my parents (dad) got me this hot little blonde escort. She was 26.

Yeah my dad is pretty cool.

[mockme]

20 years older than me.
She was in her 40's I was in my 20's.

She is now in her 60's. Gah.

[OPD940B]

She was more than twice my age at the time, actually almost 2.5 times my age now that I do the math.
Thought I had posted to this thread before.

She was my buddies mother.

Started when I was contracted to seascape an aquarium for her over the summer it the late 70's.

Filled the a 75 gallon glass tank with gravel and water and installed the filters to prep the tank. Showed her how everything worked and how put live plants and rocks in. How to contour the gravel surface to make the tank appear deeper. Then add a foil background to give it the appearance of greater depth. Several times her top would get wet making her nipples standout. And have me sporting wood. I would often stay over after a night of partying and would get up in the middle of the night for a cigarette. So after about a month of her teasing we end up out on the deck for a smoke in the middle of the night, me in a t shirt and boxers and her in an over-sized shirt and robe. Still being a little drunks I started joking with her and playing a little grab ass when she tried to teach me a lesson and grabbed for my shorts and ended up with my dick in hand. Everything kind of slowed down and we ended up naked on the deck with me behind here looking out over the street and across the way the dorms to an all girls Catholic School. I was able to nail her a few more times before she stopped saying that it wasn't right.

Other than that the oldest is my wife at 53.

[Diablofan3]

Always had a thing for older women and I was lucky enough to lose my virginity at 22 to a woman who was 56. I have seen her a few times since (she lives out of state now) but now have a 50 and 59 year old playmates. I'm 37 now. Oldest I have had though was a woman I met in a store. We flirted a little and she came over to my home and brought a friend. She was 54 and her friend was 63. The 54y.o. was lousy but her friend was great.

[charismatic]

Originally Posted by Diablofan3

Always had a thing for older women and I was lucky enough to lose my virginity at 22 to a woman who was 56. I have seen her a few times since (she lives out of state now) but now have a 50 and 59 year old playmates. I'm 37 now. Oldest I have had though was a woman I met in a store. We flirted a little and she came over to my home and brought a friend. She was 54 and her friend was 63. The 54y.o. was lousy but her friend was great.

Where you in a coma for a few years or just waiting for the right lady

[lovethempuffy]

Seven years ago when I was 51 I hooked up with a local woman who was 68 through an online adult dating site. I had for years been attracted to women older than me, and enjoyed older porn online as well. It was always a fantasy of mine to be able to be with a woman much older than me. She told me that she had contacted me because of my small penis, so I wouldn't hurt her during sex, and so she could take my whole cock into her mouth without gagging. She told me that she loved doing oral more than anything. I thought this would end up being the perfect situation for me.

I went over to her house and she met me at the door wearing just a robe. I was only inside for a couple minutes before she opened her robe and let it drop to the floor. She was in great shape and still fairly thin but not skinny, short all white hair on her head and thinning sparse gray and white pubes. Her breasts were smaller and mostly empty, hanging down long and flat about half the distance to her belly button, her chunky nipples extending from the bottom curve of her breasts pointing straight toward the ground. Except for her bush not being full and thick anymore, I couldn't have asked for a more perfect older body for me. I was getting an erection in my jeans instantly, and she noticed that.

She walked closer to me and slid the palm of her hand down across the front of my jeans rubbing along the length of my little shaft and stopped at the bottom of my crotch lightly squeezing where my balls rested inside. She made an approving “mmmmmmm” sound and proceeded to quickly remove my pants and underwear. I was by then fully erect. She dropped to her knees right there and took my whole shaft into her mouth all the way down to my balls. At that point I thought I was in heaven, and I would enjoy visiting her again many times into the future.

Unfortunately she was a terrible lover. Her technique at everything had the opposite effect of getting me off. Every time I would try to guide her or tell her what I liked that she was doing, she would quickly switch to something else and not let the good feeling gain any steam. I've never had anyone have such a tough time getting me off from the first BJ of the day, if anything I sometimes don't last as long as I'd want to be able to enjoy it. I actually ended up going soft in her mouth, and while I like being suckled soft, that's not what either of us wanted in that moment.

We went to the bedroom and I had her sit on the edge of the bed and I kneeled down and massaged her soft breasts and licked her nipples for a bit. I made my way down to her pussy and began licking. She said the medication she was on has made her juices dry up and tough for her to orgasm, so there wasn't much pleasure there for me either. She also began to make these loud grunts and noises getting into it, but again for me they were jarring and didn't sound sexy at all in my mind.

Finally I stood up and just had her hold my balls while I jerked off to get hard again. The only thing left that was turning me on about her was looking at her breasts hanging there, and seeing her looking at my penis smiling. Since I'm good at making myself hard and ready that part didn't take much effort. She laid back, I put on a heavily lubed condom and I entered her, immediately followed by the noises she was making when I was doing oral. Then within only a couple minutes she wanted to stop and get on top. It was great being able to watch her breasts jiggle and sway that way, but again she would stop and start movements every minute or two never letting any pleasurable feeling continue or develop. Then suddenly she stopped and pulled off of me saying her dry pussy was hurting now. She asked how we should finish me off, and I said that I think I would need to finish by hand. So the only way I was able to finish with her was doing it myself. I can do that at home without all the other aggravation. At least she massaged and tugged on my balls while I stroked, and had me finish into her mouth and swallowed.

I haven't found anyone else older since then to try for a good experience. All I can say is not every older woman is automatically a great lover. I just had bad luck finding one that wasn't.

[xxxxenophile]

Originally Posted by lovethempuffy

Seven years ago when I was 51 I hooked up with a local woman who was 68 through an online adult dating site... All I can say is not every older woman is automatically a great lover. I just had bad luck finding one that wasn't.

I'm sorry things weren't a better fit - I think that many older women are too shy to try such a connection, and so it's a shame that her style wasn't well matched to your turn-ons... but point for effort and get out there and find another foxy granny!

[oldncowboy]

I fucked an 80 year old woman. I was 70 at the time. she still had the wettest pussy I have ever experienced.