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

[ilovedollydog]

Wow it just hit me..

This is my story , 35 years ago I was 19 and at the bar I met this gal .. Well we hit it off and after she had some problems with her room mates I moved her into my house .. I didn't think about our age difference as she was horny and liked it in all three holes ..
Sandy was 42 and a school teacher and very horny ... I had a good time with her until she started drinking heavily and I caught her stealing from me .. I told her she had to move out and gave her two weeks to leave ..

I cut her off from sex .. BUT in the night I would wake up to her riding me .... MY junk in her trunk so to speak !!!!
Thats right ANAL ... She LOVED IT .. I would just lay there and let her go ...
These days I would kill for some of that ... Any how to make this story complete ,.... my mother passed away in 2005
at age 69 and I got to thinking about her age and the way she treated Sandy .. She was very good to her !!


Sandy was 1 year older than my MUM and I never figured it out
until MANY YEARS LATER
When Mother Passed ..... What The HELL WAS I THINKING ?????

PUSSY ..... THATS WHAT !!!!!!!!!!!!!!!!!!!!!

[apeyboy]

Awesome stories!

[grandpawoody]

This is hot and it's not. Have a couple of friends who introduced the wife and I to nudism. For the past few years it has been me only - wife no longer wants to participate. Our friends, who I will call Henry and Helen, always invited us over to go hottubbing. When wife stopped, I continued to go. Well, Henry was no longer capable of getting erect or having sex and Helen was horny. We all three would get in the hot tub together and Henry would make an excuse to get out (he actually wanted me to fuck his wife who was 84). Helen and I started kissing and hugging in the nude and my mouth was watering as she was not bad for her age. I eased my mouth down to her perky titty and all of a sudden she called a stop to the proceedings and would go no further, which I don't understand. Henry had told me that she admired my 'smooth cock' but why she would go no further I'll never know. I still think about how it would be for her to sit on my lap naked and move around vigorously. She still looks pretty good.

[Bellatrix]

I was about 35 y/o and working for a large kitchen manufacturer who supplied kitchens to Housing Associations etc, I was surveying a property and the tennant was a 66 year old divorced lady with shoulder length grey hair and you could tell when younger she was very attractive as she still turned me on at her present age, whilst measuring up she was loading her washing machine and was bending over in front of me, she was wearing black leggings and she still had a great figure, curvy as you would expect from a 66 y/o but very nice, her bum was lovely not too big etc, I could see the out line of her full knickers which always turns me on, she caught me looking and to my suprise just came out with it, saying you should have seen me when I was your age and to my suprise I answered no need you look great now, she then made a few suggestive remarks and before I knew it she was leading me upstairs to her bedroom, she said she had not been with anyone since her divorce 10 years ago, because she simply did not fancy men of her age, we had sex twice that afternoon, nothing kinky just normal sex, no blow jobs or me going down on her, just me on top, her on top and from behind.
This carried on for approximately 6 months, probably two or three times a month, it suited us both she need no string sex and my wife had lost interest in sex due to the kids being born etc, Gill that was her name had one little fetish I did not expect and was a bit embarrassed to ask me at first, she like me to put my finger up her bum which drove her wild! she then moved to be with her son & daughter in law in spain who had bought a B&B out there, which was probably a good thing as it brought a natural end to it.

By the way she was a retired teacher, she had only ended up in a Housing Association property due to her husband gambling the own home away

[rico0973]

when i was 17 and was living in a small town in Calif with my sis and her husband. One night I was at a bar with by bro in law ( I had a fake id). we ran into a friend of his who was hitting on a older woman (I later found out she was 58). We sat down with them at their table and bil and his buddy started talking about some job, and she started talking to me. I was half drunk and feeling very suave. Next thing I know, we're leaving to another bar, and I'm in the back seat with her. My bil and his friend are ignoring us and I lean over and kiss her. All hell breaks loose and next thing I know we're driving out on a country road and she's got her pant off, my pants down and she riding me. Being a bit drunk I was able to last quite awhile (impressing my bil and his buddy). We ended up parking out in the country and fortunately there was a blanket in the back of the car. I thought they were gonna want her to but ended up with just ne fucking her twice.

[Kilgore Trout]

The widest age gap occurred when I was 26 and very recently divorced – so it must have been 1984 or so. I was invited at the Grand Opening Night of a new Blues Bar by some friends. I was planning to cut it short, since I had a huge party scheduled at my pad the next evening.

I don’t remember exactly why, but there were large tables facing that small stage on which musicians performed and I ended up being seated besides a slim and sexy 50 year old short haired blonde… wearing a more or less loose fitting blouse and pair of jeans. She immediately smiled at me; and I couldn’t escape noticing her nice, full breasts under her loosely unbuttoned blouse.

Let’s say her name was Diana.

Not long after that, we began to talk, and shared about Blues, music and stuff… but the conversation veered about sex and attraction. She introduced me to a few of her friends and we decided to leave that noisy place to meet up in a nearby apartment were her sister lived. We stayed there for an hour, sharing a few drinks… and Diana became rapidly very adamant and straightforward about having sex with me. In such a way that I felt a bit uncomfortable about it, in front of people I did not even know…

At a certain point, I suggested to her that she’d come over to my place for a nightcap, since it was pretty late and I had a huge party to organize the next day. The moment we got inside, she unbuttoned her blouse and asked me to undo her bra… explaining that she had to get out of it as soon as she got home because of her large breasts. Believe me, I enthusiastically accepted her offer and began immediately to suck her nipples!

Her breasts were unbelievably soft, nice and full, with perfectly proportioned suckable nipples… I could not believe it.

In our hurry, we forgot that we were doing that on the living room carpet and she’d suggested that we’d get to the bedroom… she went to the bathroom, while I got out of my clothes and into the sheets. As soon as she got out of the bathroom, Diana asked if it was OK for me to eat her pussy… OMFG… remember, it was back in 1984 and she was totally shaved, which was not that usual at that time. She was moaning loudly as I made her cum, eagerly licking her clit… and asked if it was OK doing 69 with me. She positioned herself on top and… boy… never had such a nice blowjob done on me like that… she fingered my asshole whilst sucking and jerking my cock…moaning rhythmically while my mouth was glued to her beautiful, shaved, juicy pussy. It was totally incredible.

Then, unexpectedly, she stopped sucking and licking my cock and began to tongue my asshole… all the while moaning and telling me how good I tasted and such… I came pretty soon, believe me !

She started to suck and clean my cock with her tongue a few minutes after that and…*I got hard again, never having encountered such an experienced lady… as soon as my cock regained its hardness, she squatted on it, easing it in her sooo wet pussy, very slowly for starters, on top of me… up and down and down and up…*sucking her own nipple with one hand and rubbing her clit + teasing my balls with the other one. Then, laying on me, moving her hips in order to keep my cock happy inside of her tight pussy…

If I recall correctly, I must have cum three times that night – being younger, leaner and in much better shape, 30 years ago.

Honestly, that was the best fuck I had in my whole life : totally unexpected.

Earlier, the next day, Diana left and came to my party that evening. We were both dead tired, but smiling… after all that fucking and stuff. I learned then, that she was married and had a boyfriend on the side… I told her something like : “Don’t you get enough sex with these two alternate partners” ? And she answered that she regularly needed some kind of change, from time to time !

She called me a few weeks after… but I was already involved in a serious relationship.

I met her 15 years after that… and learned that she was friends with my (then) wife. I will never forget my wife’s facial expression when she asked Diana if she knew me…*and Diana told her something like “How can I forget” ?

[bosnic]

english granny she was around 65 at the time and could not get enough cock , loves it when you cum inside her ! also likes anal ,

[donkeydong]

I was at my aunt's 90th birthday party I am 46 I was chatting with some of her friends from the senior housing where she lives .I met this well dressed I mean actually sexy women that told me she was 91 the week before I swear she could pass for 60-65. Well long story short she had a little to much to drink and I offered her a ride home . We were no more in the car and she leaned over and grabbed my junk and said I have not had any of this since my husband passed 5 yrs ago. I was dumb founded speech less.Rest of the ride was pretty quiet it wasn't a long ride .When we got to her place I went to the door with her and she invited me in for a glass of wine .She brought me the bottle and 2 glasses and a cork puller and disappeard down the hall .Pretty soon I here music playing and here she comes down the hall see thru red teddy garters stockings and heels what a site.For 91 I was shocked well she pointed her fingure to have me to follow and the rest is awsome for a women that old her women hood was sopping wet before I ever entered her and much sloppier when I was done and she truely enjoyed her self as well as I it was a great evening and we have had several more .She is a amazing women for sure.

[donkeydong]

This 91 year old women still works at a high school library and walks to work everyday. She is truely alot of women.When she dresses everyday its always garters and stockings never pantyhose my kind of women.Thanks folks.

[cash23]

I was an 18-year-old college freshman when I met a 26-year-old German grad student at a party. Chatted for a few minutes but no sparks. A few hours later, as a friend and I were leaving, she offered to drive us home. She dropped him off first. Then she drove to her place, took me upstairs and fucked my brains out. I'd had lots of oral before but this was my first time I ever came in a girl's mouth. First time I did anal. Came in her pussy a couple of times, too.

I did the math and decided that at 26, she was older than dirt.