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

[barepubs]

When I was around 35 during the 1980's I shared a house with a 61yo women. She unpacked my clothing while I was at work and discovered I did not wear any underwear, when I got home she asked me why? I said, I prefer the comfort of my cock and balls swinging free.
We talked about my underwearless over dinner that night and finished up having good sex, I came inside her and most nights after that.
She started going without a bra and knickers after that, and in the time we lived together she never wore any underwear.
She never shaved or trimmed her pubic hair or her underarm hair.
We had great sex and she loved to suck and swallow my seamen, and when I came inside her she would sit on my cock and the seamen would dribble out of her c*nt over my cock. She would then lick up my seamen and suck my cock clean and if I got erect she would keep going until I delivered another load down her throat.
At home we had a policy of being nude unless we had visitors and always slept and showered together and often got a hand job in the shower.
I lived with her for 5 years before I got another job in another city.

[cfag]

That was a really cosy and great situation you had there mate, but sharing it with all those seamen must have been strange. Only joking but it's semen not seamen. I do envy the fact that you had such a good housing situation.

[alyndavies]

when I was 18 and working as a barman I pulled a 49 year old woman, I screwed her on the grass outside her caravan while her husband was inside sleeping!
The margin of 31 years is pretty impressive I think.

I guess the other one was in a hotel in Glasgow, I slept with a married 42 year old School teacher, while her 18 year old son was in the next room sleeping! I was 26 at the time.

[Dansei]

Last year, I lived in Japan for 2 months and I took part in a work-exchange program. I did some farm work in exchange for food and a room. The lady who owned the farm and house was a 56 year divorced japanese woman(I was 19 at the time). The 3rd night I was there after we came home from doing work in the plot of farm land she owned, she made me take off my pants before I went inside the house, because she said my pants were very dirty. She spoke in japanese all the time(I understand quite a bit of japanese) however I tried to pretend I didnt understand her, because it is embarassing for me to take of my clothes in front of people because i get an erection if I do it in front of people. So she ended up saying "pants, take off" in english and so then I couldnt fake any longer, so I took of my pants and had a huge erection, and she could clearly see that I had a huge erection from my thin boxers. It was quite for a few seconds until she said(the rest of this conversation took place in japanese) and asked if I was excited, I said I was a bit nervous, and she asked why, and I said it is embarassing for me take of clothes in front of people. She said it was ok, because I have a thing I should be proud to show in front of her and then she asked me if I had an erection because of her. I thought she was very sexy for her age and I said yes, it is because of you. Then she came close to me and whispered in my ear and and touched my shoulders and told me to get inside. She then asked if I wanted her, and I said yes, so we started kissing and we went in the bedroom and we started to have sex. She taught me so many moves, she was such an experienced women, I was so impressed with her and she was so impressed at my white, young dick and she said it was first time she had sex with a foreigner before. We had sex 2 more times during my stay, and she asked me to marry her before I left and I could work on her farm and get a japanese work visa, but I knew it would not be right to marry a woman who is that much older then me, so I returned to Tokyo where I got rejected by all the women my age and never had sex again the rest of the time I was in japan and then returned home to America, and i kind of regret not taking up on her offer to get married.

[mgguy]

Originally Posted by Dansei

Last year, I lived in Japan for 2 months and I took part in a work-exchange program. I did some farm work in exchange for food and a room. The lady who owned the farm and house was a 56 year divorced japanese woman(I was 19 at the time). The 3rd night I was there after we came home from doing work in the plot of farm land she owned, she made me take off my pants before I went inside the house, because she said my pants were very dirty. She spoke in japanese all the time(I understand quite a bit of japanese) however I tried to pretend I didnt understand her, because it is embarassing for me to take of my clothes in front of people because i get an erection if I do it in front of people. So she ended up saying "pants, take off" in english and so then I couldnt fake any longer, so I took of my pants and had a huge erection, and she could clearly see that I had a huge erection from my thin boxers. It was quite for a few seconds until she said(the rest of this conversation took place in japanese) and asked if I was excited, I said I was a bit nervous, and she asked why, and I said it is embarassing for me take of clothes in front of people. She said it was ok, because I have a thing I should be proud to show in front of her and then she asked me if I had an erection because of her. I thought she was very sexy for her age and I said yes, it is because of you. Then she came close to me and whispered in my ear and and touched my shoulders and told me to get inside. She then asked if I wanted her, and I said yes, so we started kissing and we went in the bedroom and we started to have sex. She taught me so many moves, she was such an experienced women, I was so impressed with her and she was so impressed at my white, young dick and she said it was first time she had sex with a foreigner before. We had sex 2 more times during my stay, and she asked me to marry her before I left and I could work on her farm and get a japanese work visa, but I knew it would not be right to marry a woman who is that much older then me, so I returned to Tokyo where I got rejected by all the women my age and never had sex again the rest of the time I was in japan and then returned home to America, and i kind of regret not taking up on her offer to get married.

That's a hot story!!!

[Bredjones]

When I was 19 or so I worked at an apartment building. There was a 62 year old woman that used to sit in the lobby in the mornings and wait for her bus to start running. When she would leave the lobby every morning I would watch her walk down the street till she caught her bus. At first to make sure she was safe but eventually found myself staring at her HUGE ass!

She wasn't a beauty queen, though I found out later she was a fucking KNOCKOUT as a younger woman! She was a large woman which I like. And sometimes she would use a cane when her knee bothered her. But let me tell you... She had this raw sexuality about her after we spent a few months getting to know each other 30 minutes at a time. She just started talking nasty. About how she loved sucking dick. And the sex parties she used to go to in the 70's. So being a night security guard at 19 is erection inspiring enough in this particular building and I could fill the forum with other things that happened in my 4 years there but now I'm ending my mornings with a 62 year old woman making me hard!

In hindsight she was doing everything she could to let me know we could fuck whenever I chose but I was so damn dense and I guess in awe of her age that those four years were over before I finally made my play. I eventually got in trouble for living with another women who lived in the building (I was horribly young and stupid) and we were actually breaking up at the same time I was being reassigned to another building. So I was removing some personal items from the apartment and I ran into this lady.... Lets call her Mrs. Robinson. and she asked me why I hadn't been at the desk. I fessed up and told her the whole story and added a little twist... I told her I didn't have anywhere to stay the night.

She said I could stay with her. I follow her up to her place. She goes in the bedroom and changes into the old lady house dress number. We talked for a while and I'm still too nervous to make my move so I decide to wait and see how she going to plan out the sleeping arrangements. We had a good time. She even let me smoke weed in her place. Lol. So its getting close to 10 and she hands me towels for the shower. I hop in and do my thing. Come out and all the lights in the apt are out except her bed room. I walk in with the towel around my waist and tell her I don't have anything to sleep in but my underwear. She asks how I slept with my ex. I told her nude. She says she doesn't mind if I get comfortable. So I drop the towel and turn off the light and jump in the bed.

Obviously ROCK HARD at this point! So we just sorta cuddle. She compliments me on my penis. And then watches tv! I'm obviously gonna have to work for this a bit more. So I ask can I see her breast. She ask me if I'm a breast man (I am among other things lol) I say yes and she says how does she know if She shows them to me that I won't want more... I make my promises/lies and she pulls it out. HUGE. With the biggest nipples and areoles I had seen at that point in my life. I say I want to suck them. She laughs at me and says she knew that was coming. So I start sucking. And she starts moaning. So I start touching her all over and fingering her... She's super wet. And is cumming in a couple minutes. So I want to go down on her to really make it memorable because I know I'm not going to last long. Lol. She wouldn't let me go down her for whatever reason

So I get on top of her and slide in. So ridiculously tight. Like it hasn't been touched in ages. And I start stroking and it's like 2 minutes and I'm ready to blow. I was about to try the old position switch stall maneuver but I know the visual of that big beautiful ass won't help me hold out at all. But sure enough ms Robinson says let's to it doggy I'm better on my knees than on my back. Oddly enough the sheer fear of premature ejaculation actually got me under some control and I played it cool like... This feels so good let me do it a little longer. Lol. So I get a few more strokes in. And we go to reposition. She backs to the end of thebed and puts her ass up. My heart is in my throat it looks so damn good Audi hold of for a few more seconds the. Dive in and wrap my hands around her hips and start pumping. Thinkin ive got some control now. Well!!!..... She started fucking ME like no damn tomorrow. Ass jumping all overthe place like a damn 20 year old. And I blew it. BIG TIME!! One of those knee wobbling orgasms it takes a few minutes to recover from.

She goes in the bathroom to pee and wash and I'm laying in bed panting. She comes in the room and says... May now that that thing is drained u can get some sleep. As I'm thinking that's just what I'm about to do she says to me... We can do this as much as u want just don't hurt my feelings. I said ok and drifted off.

Morning... I wake up and she's not in the room. I find her in the living room on the computer and I walk over to her. She playing solitaire. I'm standing just beside her and she makes her move on the computer then just turns around and takes my dick in her mouth. Sucks me to full attention then makes me cum. We spent that whole morning having the best sex. So I'm leaving and I ask when can I come back. She says whenever you want. Just ring the bell. (no phone) so as I'm leaving to building the janitor who I think ratted on me for living with my ex in the first place sees me and wants to chat it up. I'm sure I had guilt written all over my face and i wasn't in the mood for him. So I went to my car and went to my moms place. 30 minute drive...Soon as I get there mom tells me my company called. I call and the operator fowards me to my ops manager (who just chewed me a new ass for living in the building ) and he says he just got a report that I was seen in the building and that I wasn't supposed to be there. I told him I was getting my belongings and that's all. He asked if I had everything and I said yes. He said if he ever heard about me in that building again he would fire me. (rat bastard janitor!!) so I never went back to see her. Couldn't call and by the time I thought to write her a letter it was such a long awkward time that I just let it go. I drive by the place often. I saw her walking into the lobby once years after but I just let it go again. I'm 32 now and to this day a lot if my masturbation ends with her on my mind

[daskers]

Well to start with on the first one,I was 18 and she was 37. On the second one which was my brothers motherinlaw at the time,I was 26 and she was 56. And the last one,I was 41 and she was 62. Those are the three oldest I have ever fucked,I'm 46 now and my wife is 41 we married in 2009.

[rico61]

for me she wasn't so old. she was 38 and i was 19. the sister of guys i met in holidays

[stuffy1969]

I was 19 and she was 44 and the mother of my Gf at the time

[taz1020]

i was 22 she was 45 she was my gfs mum she was hot