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

[cators]

Hmmm good question how old is your mom again?

[ilovedollydog]

Originally Posted by maxdibble

Ok it was the late 1980's I was 35 No cell phones no micro sized video Cameras. Mine was full sized tapes. I was asked to video tape a property for sale. And Duplicate the video and show the ranch house and the property and the Crop. I met the owner and his lady who worked as his Secretary and house keeper of sorts. He was in his late 70s and was an arrogant British ass, asked all the part of the lord of the manner. However his House keeper for 30 plus years was a real sweet lady. He asked if I knew anyone who could trim the trees rubbing against the roof. I told him I could do that and would come to do it said the next day. The house keeper was 87 that year and a boxed red head that had gray roots showing more than she liked and she was very friendly showing me where the tools and saws were. She always was elegant as she moved around the property. So I trimmed the trees and came down pretty dirty and sweaty. Her name was Jessie but she said her friends all called her Pinky. She said to go get ready for a shower in the bathroom off the hall near her room. She said to strip and she would wash my clothes while I showered and she just waited for me to take them off. She stood there looking at me as I undressed and then took my clothes and left me getting into the shower nude.

When I shut off the shower and got out there she was with warm towels from the dryer. She said turn around and she dried my back and then said turn around again she toweled my legs and then my shoulders and chest stomach and my cock and balls. She then sucked my penis into her mouth and said nothing as she sucked me until I came. She said relax on the couch wrapped in the towel until my clothes were out of the dryer. She made me a grilled ham and cheese and gave me a cold beer. Shit head was taking a nap mid afternoon so we were on her side of the Ranch house. I said thank you for everything and she says no she wanted to thank me. And so the next nine years years I did handy work around the ranch. I have more if you want just let me know.

That's what you call Full Service " CLEANING "

[Krst]

When I was 19, I befriended a couple who where probably in their early forties. Her name was Nina; his name Alex. The couple had two beautiful daughters, around my age, who were also my friends. I had many reasons to frequent them during evening time, being the main one the opportunity I had to see the two girls in their see-through nighties. I also loved to get in my hands, and sniff, their used panties, which they deposited in a laundry container in the bathroom, but that's another story.

That Sunday evening I stopped by just to visit with the whole family and have a family moment. But to my surprise Nina was alone. Not much ago her husband had had to leave in a hurry to take care of a construction contract in the making (he was a builder), and the girls where elsewhere visiting with other girlfriends.

As usual, Nina invited me in and asked if I had ate. "No," I said. So she offered me food which I accepted. While a ate, she went to take a shower. She came out from the shower with a gown on -- a piece of clothe I was used to see her on -- and we both sat in the living room to chat. Being 19, shy, naive and innocent, I must say I was very, very respectful of Nina. Her husband was somebody I had in high regard, and I saw her as if she was my mother.

The conversation spun around trivial topics -- my college, my sister, her daughters, etc. But then, at some point she changed whatever topic we were at and, while pulling her gown up to show me her thighs she said, "today we went to the beach and I got a tan".

I looked down to her thighs. They looked shiny and reddish, and beautiful.

- Oh, wow, I think you got a nice tan. Any burning sensation? - I inquired, trying to extend the topic as I found it interesting.

She ignored my question. Instead, she slid her fingers on the upper part of her thighs as if caressing them while adding, "I've always been admired by men because of my legs. They say I have beautiful legs."

- Well, I think they are right - I said - I think you were blessed with beautiful legs.

At that point I was a little torn inside. On one side, I respected Nina and her husband. On the other, I was fascinated by the beauty of her legs and the cleavage her gown was letting me see. It was obvious she wasn't wearing any bra.

- But I have a problem - she added.

- What is that?

- I suffer from an illness.

- What do you mean?

Then, lifting her head to look directly in my eyes with this innocent face, as if begging for some empathy on my part, she proceeded on:

- From time to time I experience this horrible pain in my vagina. It's so intense that I can't bear my husband penetrating me.

I swallowed a little bit thick as I sensed she was wading into new waters. It was a territory I wasn't prepared for, specially because it was her, Nina. Besides that, I had never been with a woman, and had never talked with one about their intimate problems. What did I know about vaginal pain?

Not knowing what to say I simply added:

- I'm sorry to hear that.

Nina decided to elaborate on her topic. Looking down to her thighs again, and while opening her legs and pulling her gown further up she said:

- You have no idea how painful it is. During those days a small vein forms and it goes from this side -- she said while opening her legs even further apart and touching the right side of her crotch with the finger of her right hand -- and goes across my inner labia to the other side.

I was looking to her crotch. She was wearing white panties. Her right outer labia protruded a little bit out of the panty line and I could appreciate some hair. It was evident she wasn't shaved.

I knew what she was going to do next. She wanted to show me exactly how "the small vein" ran across her slit. I knew that panty was going to be pulled aside. My heart was racing in such a way I thought it was going to stop any moment.

And then, at the distance we heard the metallic noise produced by the gate when the girls opened it. They were coming back home.

The last thing I was able to say was, "I hope you will not experience that pain again." The nervousness caused by the moment and the imminent presence of the girls made my hard-on go away... until later that night, when I was alone in the bathroom of my house.

[prototype01]

The oldest woman you've been with?

38 - I was 28. She was huge, must have gone at least 16 -18 stone. I prefer the slim ones, but wanted to try a big one, and met her through an advert she placed in the local paper. The funny thing is, I'm 52 now, and she's still the oldest I've been with!


[I]How old would you go?[I]

I would go up to 132 - that would be a threesome with Joanna Lumley and Felicity Kendal

[photophil]

when i was 22 i wnet to a work night out. ended up dancing with a 42 year old secretary who was definitely a MILF but i never thought in a month of sundays we'd get together. She was married, had a son my age and appeared very happy with it.

The venue was quite dark and as it was getting towards the end of the evening there were few people around. As we danced i started to touch her and stroke her legs, sliding my hand up her skirt a bit further each time. Eventually I hit stocking top (i hadnt much experience of suspenders and stockings then).

When we were kicked out I asked her to wait for me then took her round the corner on the pretext of getting a taxi (as i didnt want to be seen by me colleagues- i thought i might get a slagging and she might get a reputation).

We got a cab abck to my flat which was in a tenement block on a hill. The bedroom had huge windows and was easily overlooked form the flats across the street. We had a great night together and I did pretty much everything I every wanted to try sexually with her, all in front of my open curtains. (to be fair it was about 2am so probably noone was watching.

My flatmates saw her leave so i did get a royal slagging but I have to say I didnt give a damn- what a great night!

[charismatic]

Originally Posted by photophil

when i was 22 i wnet to a work night out. ended up dancing with a 42 year old secretary who was definitely a MILF but i never thought in a month of sundays we'd get together. She was married, had a son my age and appeared very happy with it.

The venue was quite dark and as it was getting towards the end of the evening there were few people around. As we danced i started to touch her and stroke her legs, sliding my hand up her skirt a bit further each time. Eventually I hit stocking top (i hadnt much experience of suspenders and stockings then).

When we were kicked out I asked her to wait for me then took her round the corner on the pretext of getting a taxi (as i didnt want to be seen by me colleagues- i thought i might get a slagging and she might get a reputation).

We got a cab abck to my flat which was in a tenement block on a hill. The bedroom had huge windows and was easily overlooked form the flats across the street. We had a great night together and I did pretty much everything I every wanted to try sexually with her, all in front of my open curtains. (to be fair it was about 2am so probably noone was watching.

My flatmates saw her leave so i did get a royal slagging but I have to say I didnt give a damn- what a great night!

Good story, mine was on a work night out aswell.

Was out in town with a few from work and i started to get talking to a women from work. Never really bothered with her before. we were talking about the age difference ( she was 45 and i was 33 ), We were getting on famously and a lot of snogging was taking place. We both needed the toilet, so I dragged her into the gents and hands were everywhere. Unfortunately it was the wrong time of the month, but she did give me a great blow and tit wank.

We tidied ourselves up and then went back to the others and got some strange looks. Next thing I know we are all leaving and she jumps straight into a waiting car.............................. Her husbands car

[aussiemale7]

Im 26 and dating a 37 year old the oldest i have had was 45 when i was 23, she is married and love it all. she is also a semi famous actress here in Australia.

[srellik]

i was almost 40 n she was 60ish; great tight c*nt, took a while to get wet; body was bad but she was totally uninhibited the longer the fuck session lasted; i'd fuck up to about 75yo for most women

[jennyz]

Originally Posted by aussiemale7

Im 26 and dating a 37 year old the oldest i have had was 45 when i was 23, she is married and love it all. she is also a semi famous actress here in Australia.

How famous?

[Mr and Mrs W]

Our current 52 Year old friend. As you see, she is very fun and enjoyable.