Oldest Person You've Had Sex With

Sounds like a nice time was had by all. Any unusual requests from any of them? Were some particularly voracious in their appetites? Any that you had to turn away for one reason or another?

 

One of the memorable women I played with was a gal who asked me if I had ever had a gal with no teeth. She called it a gum job !! lol
I said no and she took her teeth out and gave me the most memorable blow job I ever had.
She told me she had always loved giving oral and it was one nice side effect of having gotten dentures, I TOTALLY agreed.
Between her mouth and her playing with m y balls she always made me cum fast.

One gal was a bit self census about her size, she was not fat but a plus size for sure. I have always loved f all sized and BBW so I told her no, it was my preference.
It was so interesting and erotic seeing her super soft skin. As we get oder we loose muscle tone and mass and on a full sized women seeing the soft folds and texture was so nice, for me anyway way.
She was interested in laying back and letting me take charge and I ate her then fucked her like I did when I was much younger.

Most older women I saw were average or slimmer in size, lots of low hanging or drippy tits. I was so impressed with how big some of their nipples would get when aroused.
It almost looked funny seeing big nipples on half full boobs but they all loved it when I would play with their nipples.

 

I have fucked a couple of older women, I was 50 they were 55+ one was just ok the other one like to fuck 12+ hours, EVERY day she knew I was married and she still fuck me, 4 months later she asked me how much I was fucking my wife I said 3-7 times a week I didn't tell my GF that i cummmm in my wife every time but honestly I like the other women in bed more I told her that too I would pound her hard I got bored one time and started fisting her then we found out she was a squitter should have seen how loose I made her pussy, it was amazing how the next day I could slip my cock inside her pussy and go work making her squirt over and over like 10 times we would take little breaks while i stayed in her then she would squeeze my cock which was code for lets fuck some more she had 5 kids with her x husband never had a women like her that like to fuck as much as she did ........I was with her for 5+ years then we broke up I know she got a bf after I left they last about a year wounder what her thought hee hee

 

Were they happy to pass you around or were there jealousies? Was it always one on one? Did they ever team up or watch one another with you?

 

Yes they did pass me around I know they talked between themselves. Some of them would say I hear you and ..... have been spending some quality time together, or something along those lines.I always found that kind of funny, also a post to my ego ... grin. If they were ever jealousies I never learned about it but we would have a few jokes about it like dont worry their is plenty to go around or your not delouse are you etc.
As for teaming up, no, would have been nice but no. I thought about stuff like that but I never wanted too push it too far. too much playing in one place could very well lead to trouble.

 

I was 23 and he was 44, now I’m 43 and he’s 64. I’d go there again. I wanked in front of him a lot as did he. Massive turn on.

 

It nice they could pass you around with no jealousies. As with many other things, I doubt a younger group of women could have achieved that.

 

74 and I was 50ish

 

I was groomed at a young age by a 50 year old buxom women she was very experienced and she taught me how to fuck her in different positions. Not getting enough cock was her problem I spent a month with her mostly in bed I was her young stallion she told me

 

when I was 19 I use to fuck my boss's 66yr old wife. she had such a sexy slim body and liked it hard and rough.

 

When I was 25, I saw 2 women dancing in a NYC club. I went up to them and danced with the hotter one. We were in the corner of the dance floor right under the dj. We started kissing and next thing you know, she had pulled up her sundress and we discreetly had sex on the dance floor. Some of the things I did when I was young I couldn't imagine doing today. Afterwards, we went for more drinks and I saw her license. She was 47. I thought she was in her 30s. That was the biggest age gap where the woman was older than me.

 

68, years before she had been one of the petite girls on the flying trapeze and maintained her figure very well.

 

I’ve posted before about other encounters over the years but last fall I had a few encounters with a neighbor who was 77. I’m 63. We knew each other for years and she was moving at the end of last year. Our conversations over last summer gradually turned to sex and she said her husband was in his 80s and their sex life had been nonexistent for years. Somehow she said she was looking for a nice encounter and if I knew anyone. Of course given my active life how could I refuse. We met at her place because her husband goes out every day for a few hours with friends. She actually has a decent body and huge tits. I started by performing oral on her and she came rather quickly. She blew me for a bit and then I unloaded into her. We met a few times afterwards and then she moved.

 

He was sixty-something years old, I was 16-17

 

Anyone ever find out?

 

It seems like I set a new record a few times each week when I fuck my wife. She is 77

 

In another post you said she was 68. 5 hours later she aged 9 years. Even still that's pretty rare a woman still having sex at that age.

 

The oldest woman I have had sex with was 48 years old (the last time I plowed my ex). Ever since I have only banged 25-40 year old women. However, next month an old flame (a year younger than me) will be back in town (we dated 40 years ago). I saw her recently and she looks great and is in great shape. So, I've been watching "Mature" porn to get my mind in the right state.

 

In my thirties, I began to realize that I have an attraction towards older women and actively pursued several ladies over the course of a few years. Mostly, they were work colleagues and were In their 50s and 60s. I'm not going to pretend that they all looked young for their age or had maintained a fantastic figure from their youth, but each one was sexy in my eyes because I think a sexually attractive woman never loses that allure. The sort of job I was doing gave me opportunities to meet up secretly in the daytime (some were married women) or the chance to spend some quiet hours alone together on night shifts.

The oldest woman that I made love with was my new landlady, Frances. She was 70 years of age when I met her (I was just 40 at the time) and quite the revelation. We had spoken on the phone about the flat, prior to meeting and I thought I detected something in the way she spoke. It wasn't just her upper-class accent, or the words she used, it felt like an unusual connection. It was hard to describe, but I knew that I wanted to meet this woman in person.

It was late autumn on the day she showed me the place, and she was wearing a long fur coat, buttoned up to the neck. I was already attracted to her, and the flat itself was just right. As we chatted, she apologized for there being no bed but demonstrated to me that the couch in the lounge pulled out as a sofa-bed. I lay on it, with her standing right next to it. She asked if it was OK and, chancing my luck, I said it was hard to tell and would she mind just lying on it to give me an idea of how comfortable it could be. To my pleasant surprise, she did just that and before long we were next to each other. I moved around 'innocently' for a moment or two, just an excuse to brush against her really, then she asked me what I thought. I told her that it felt really nice and when I asked her the same question she agreed with me. So I told her that it felt lovely to be lying there with such an attractive woman, at which she scoffed, but didn't seem to mind as I stroked her hair, then her face, and began to kiss her. She responded to my affection, and I gradually unbuttoned that long fur coat. She was completely naked underneath. Later, after we had spent some time making love on that coat of hers, with the sofa-bed springs squeaking and us giggling, she told me that she had felt the same thing I did from our phone conversation alone and that's why she had dressed like she had, because she was so excited about meeting me.

She was one of the most beautiful and sexy women it's ever been my privilege to be with and I was her tenant, and regular lover, until work called me to another part of the country and I had to say goodbye. She was 73 the last time we made love, on that sofa bed once more for old time's sake.