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

[oldncowboy]

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

[SlyBry2010]

I was 28 and she was 42. In the late 1980s we met at a local singles group (pre-Internet) that put notices in the free advert sheet that came out every week. We talked while having brunch a couple of times. There wasn't really anyone in my age group- mostly older like her. Eventually she talked me into coming over to her place after dinner. I say that because she wasn't actually very attractive- definitely horse-faced and dumpy body shape. Very nice boobs, actually - not huge but a great handful with large (and quite sensitive) nipples. But, I wasn't getting anything anywhere else and thought what the hell - give it a shot.

Anyway we lay around her living room while we watched a couple of (regular) movies and I drank beer. She steered the conversation toward sex, and to the point of showing me an adult mail-order catalog that she regularly got that had all kinds of toys and sexy things and movies (on VHS, of course). She pointed to a pic of a dildo and said something like, "That one is mine."

Holy crap, it was HUGE. It was supposedly molded from a guy who went by "Jeff Stryker", a porn star of the 80s. The next thing I know she scampered off to her bedroom and brought out "Jeff" to show off. She talked about how sometimes it hurt her to fuck herself with the dildo and I advised her to get the usual lube from the drug store. She was like, "Wow- thanks!" Apparently it never occurred to her?

In time we started kissing and she was grabbing my cock through my shorts. I don't think she was getting much action at the time, either, so she was happy to latch on. We made it to her bedroom and she kept the lights off, with her master bathroom light on to give us a little illumination.

Well, not the most stellar sex ever. Like lovethempuffy told us, lots of enthusiasm but no skills per se. Nice to be in her mouth but couldn't stick with any action long enough. I loved playing with her tits and she definitely enjoyed. I don't recall the 'blow-by-blow', so to speak, too much but when I entered her it quite a disappointment.

I am not small but still was no match for a pussy that had been abused by ole "Jeff" for who knows how long. To be fair, I was more used to the grip of my hand than a pussy at that point in my life, but still. She had a great time because I banged her in every position she wanted to try. She was the first I experienced to actually get on top and pull her legs up into a squat and bounce up and down. Still didn't work. I know she came a few times but I never did.

We got together a few more times with largely equally unsatisfactory results. She came to my place and watched a bit of decent 'couples' porn with me. We got naked and masturbated together on my couch but she wanted the D so after a bit she stood up and turned her back to me and sat on my cock and bounced on me while we both continued to watch the porn. I really gave her nipples attention then and she just about came from that.

The only time I came was with us laying on her living room floor and making out while she tried to suck me off. Just like lovethempuffy related, she was not Ginger Lynn, and in time I just jacked it off while she licked the head and then had me shoot in her mouth.

In retrospect I was at a bad place in life then and not overly thrilled with women in general. She really didn't get a fair shake from me. I wish now that I was paying closer attention and appreciating what she did have to offer rather than just focused on the negative. Both of us definitely would have had more fun. She got married to some pathetic bastard a few years later and if she's still alive I think she's quite happy.

[Couplein2MFM]

Five years ago we were on vacation at a beachside cottage. The cottages were directly on the Gulf Beach and wrapped in a horseshoe around a pool. We had arranged to meet a local couple on a online swinger site and sat around the pool drinking and grilling. The lady was super hot and sexy and looked maybe 50 but said she was 68. She had pert little breasts with rock hard nipples and an amazing tight ass and great legs. Her hair was colored blonde and below her shoulders. There was a definite attraction and chemistry between she and I.

Her husband looked every bit of his 65 years and there was zero attraction to him on my wife's part.

The lady and I ended up in the pool naked and then fucking in a pool side open cabana bed. She was a fantastic lover and one had one of the tightest pussy's I have ever had. She also had a very fresh and clean smelling pussy when I went down on her and she could suck cock like she really enjoyed it. My wife and the husband sat at a picnic table talking the entire time.

I have not ever met or seen a lady of her age that looked as good as she did but if I found one with her looks her age would not matter.

[Thebigg]

When my ex and I broke up (at 48), she was fucking a 28 year old. I couldn't figure out why this young guy would want her. We had these late night sex texts, and I asked her why this dude wanted to fuck her like 5 times a day. She told me, "you idiot. 28 year old girls have no experience. They are all 'hot dog hallways'. He knows I have had every shape and size, and work hard to keep my muscles strong and contoured." After we got back together, I knew exactly what she meant!!!

[FREDBARNES]

No Limit :-)

I had wanted to fuck a woman born in the 1800's but never got to & its too late now.

I would love to fuck the crap out of Betty White ( Better rephrase that as at her age I might Literally fuck the crap out of her LMAO)

[Macmmot]

I was 26 and she was 84 and my bosses mother. She was stand reluctant at first but once I was sucking her nipples she turned into a porn star and to this day she was the best sex in my life. So tight wet and made me fuck her over and over. Can not believe 84 year old granny could fuck like a kid. No one ever found out about us but her old saggy body did it for me. Just to give this old woman the last sex in her life was such a thrill for me

[SixPointFive]

My sister's sister in law is early to mid 50s and is HOT! Met her for the first time last year and spent the next few days thinking about her whilst jerking off.

[thorne_uk]

I slept with one who told me she was 65 but I think she was 70 as I looked her up on the electoral roll.

She didnt look her age and I was 40 at the time, I always had a granny fantasy so when I met her i just went for it and she would come over and stay at mine at weekends. She had been married once with two children who were older than me. She had only every been with her ex husband so I was only the second man she had every slept with but she wanted to make up for lost time. She let me shave her pussy which was the first time she had ever been shaven, she did anal, loved giving blowjobs which she had never done before. I would buy her sexy things to wear and she had a great body but it was never more than a sex thing and after a while it just fizzled out and we lost contact.

[Fox Mulder]

So far, it was a grandmother, mid 50s. How old will I go?
First...young guys, I get it. I know that for you, anything above 40 is a helluva novelty for ya. Well, here's good news for you. Sex is not an Olympic Event. There is no age at which one must consider retirement. Young women are beautiful. Wonderful. The good news is, the older you get the more you appreciate the beauty and wonder of the older ones. Your brain matures. You'll reach a point where you'll enjoy looking at the young ones and having a fantasy or two...but you won't want to hang out with the vast majority of them. Once they open their mouths and words come out, you'll realize there's nothing there you want beyond pussy. Mentally, they're out of your league. You'll want someone around you that you can relate to. More good news...pussy tastes just as good, be it 20 or 50. Your cock will be just as happy inside a grandma as it would be in a young babe. Take comfort in this, because one day you'll be carrying some extra pounds and wrinkles...a little gray in your beard. You'll become largely invisible to the age group you're focused on now. When that happens, young guys, if you're not an asshole, you'll still find someone to love you, and it will be very enjoyable. Meanwhile, enjoy the young flesh while you can...and if you find a cougar looking for young dick, go for it. She'll make you a better lover and maybe a better man.
How old will I go? It depends on how old I live to be.

[wifeuserscot]

In my late 20's and 30's I often went with older married women often with the husband present. On average the age gap was 15 - 20 years. I think one or two might have been 30 years older. They were still fine f***s