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

I have just fucked a woman (my wife) on her 70’Th birthday, it was as good a fuck as when I first fucked her (and took her cherry) 51 years ago.
She has had lot’s of different cocks fuck her over the last 35 years while we have been swinging and having M F M threesomes and still loves sex.
She still gets plenty of offers when she goes on web cam.
Anyone here top that?

An older woman!
 

No rick181au, I certainly cannot top that! But I can say this...I am seeing a woman on the side that is in her mid-fiftties (my age). She is currently married and contemplating divorce. She has a face and a body of a woman in her early thirties. She is firm, tall and slender, has a small tight ass (no "cottage cheese" nor ripples), and a recently well-done boob job by a top-notch surgeon that looks extremely natural. With this gorgeous figure she also sports a beautiful face. In short, she is a Class 10+ MILF...! The sex that we have is nothing short of supernatural..! She loves to suck cock and fuck! So how old would I go? For me there are no limits as long as the woman in question is attractive and still sports a great body! And when you come across one of these rare finds that additionally likes to fuck, it can be one of the best experiences you have ever had..! Let's keep searching...!

Rick you are a lucky guy.
I love older women and wouldn't put an age limit on them.
Have you pics to share of your sexy 70 year old?

I did an 84 year old at a swing club once. I was in my 50s. She was great.

DR

she was 61
 

About ten years ago i had sex with a 61yr old, i was in my 40s, i can't go into to much detail because it was in a work enviroment, and she was married her hubby worked at the same place, but she instigated the whole thing, the 1st time she came on to me in an office where we could lock the door, she sat on my lap just fooling around, she started rubbing me and kissing me, next thing you know i had her tits out and she was sucking my cock, i was so hard it hurt, we got on the floor and fucked, i came inside her and we then attended the same meeting with her hubby there as well, we had a couple of other fondles at different times, and she told me that the 1st time she was only gonna give me a blow job, it fizzled out after out after that. so i would'nt put any upper age limit, there all hot as fuck given the right enviroment

any pics? :)

I am now 81 (82 in July) but when I was 76, I had the last fuck with my then wife who was 9 years my senior. - she was of course 85 - and just as sexy, and wanting it, as ever. When she then (the following week) had another Stroke, and our female doctor came to see her, she came into the kitchen where I was busy cooking, and calling me by my christian name, said, sorry - but you must stop, this coupling with J... - you are now too large for her. needless, to say, I am still pumping for England.

In my 40s, I was in the Middle East in the 80s on bachelor status for about 6 years, in a company flat. I got plenty of fucking when home on frequent visits, the wife 4 years younger than me was hot at Heathrow picking me up , never mind waiting till we got home.

However, I did some babysitting for some close friends, kids about 5 and 7. Occasionally the mum's mother would visit them as she passed through. She was a high powered business lady travelling on her own time and expense but opted to stay with them on the compound to see her grandchildren, rather than a hotel, but in a separate villa for both privacy and to do some work in the city they lived in.

I was still needed on my usual Tuesday night when they had a choir practice and get together afterwards and MIL was out doing business in the evening as usual in the Middle East. She could hold her own with any Arab and was a doughty formidable presence. She came back early that night and called in for a chat and we opened some "illegal" booze. She was no great looker, aged 68, classy gold specs on the end of her nose, short and dumpy but wore classy well fitted suits in Western situations but coverall smock things out there. Her bleached blonde hair was always beautifully coffered - she hated covering it as she had to do out there, her makeup immaculate and she wore bling all the time, painted finger nails, the works. I had never seen her at the pool but I could tell she was stacked and also had a big arse.

The drink flowed, she got raunchy, she was divorced and we fucked out on the patio in the heat of the night. She had enormous saggy knockers with nipples that pointed downwards, a fat roly poly belly, dimpled buttocks but quite nice legs and ankles. Her underwear was all Janet Reger silk. She was dripping when I got inside her knickers and more or less pinned me down to climb aboard and ride me with her shaven sn*tch which was surprisingly tight but very very wet.

She visited them often but we never quite got it together again, but she was amazing.

She was 62
 

... I was 31 or so.

Her daughter was my babysitter - and I knew she was older than I - but had no idea how much older. Since her oldest child was about 8 years older than my oldest - I figured her for early 40's or maybe even late-40's.

We hung out all summer - I slept over at her house a couple of Friday/Saturday nights - when both our kids were with their non-custodial parent.

I knew the relationship was terminal - I was in the Army and there was NO way she would leave that area - ever. Nevertheless, we had some very wild weekends.

She was Cuban - and had very coarse pubic hair on her pussy. I loved going down on her - and she would cum and cum from that. (I'm thinking she might not have ever had that done before - not sure.) She would grab my head and pull me into her pussy as I nibbled on her clit and stuck my tongue up inside her. At that time in my life, I was a little quick on the cum - if you know what I mean - so, I did my best to make sure my partner was happy before I ever put my cock inside her ... because, once I did that, it wouldn't take long before I would shoot my load.

She was multi-orgasmic - and would enjoy my tongue until she would - at some point - pull me up to kiss her neck/face/lips/ears - and fuck her. She was VERY tight - almost virginally tight.

It's been 23 years or so since that first time in her bed - and I can remember it like it was last night.

Towards the end of that summer, her daughter told me her age ... I was shocked.

Not sure if this is going to work or not?

Thanks for the pic Rick.
Loving all the stories, let's have more and more pics!

WOW she's hot rick, too good to keep to yourself, show us more of this hot babe

61
 

I have been fucking my 61 year old widowed neighbour occasionally for about 4 years. I can't think I'll ever want to stop because she's too old. She keeps herself very fit, and is very charming and good fun - so still very attractive. Two years ago, I got to feel the tits of a 68 year old. They were big and lovely.

I was 23 and she was 39. She was a part time model and a MILF. Great fuck she was!!!!

I was 27 and she was a fit 42 year old Filipino mother of one. Dated her for about a year and wow cant say how cool it was being chased after instead of having to do the chasing. She was the one that seduced me and I did not even know what was going on till it was way too late lol.

Italian love
 

I was a few years under 18 and went to Italy on an exchange trip. My host mother, who was divorced, and we had some fun she had to be mid 40s.

Donna
 

The oldest Fuck I have had was my wife Donna. 65 (Her current age).;)
And I hope to be still fucking her when she's 90.:D

Donna is lovely and has great tits. Love them big like hers. Any more pics pls?

just a reminder
 

this thread is who is the OLDEST woman you've been with, not the greatest age gap surley, just a reminder.

Except
 

Except, Cornish guy, you are going to get age gap stories (no pun) because for many the answer is not very impressive. As for me the oldest woman I ever fucked was 38, which is nothing - indeed, a
young hottie to many of you old pervs on here.

Except, I was 16 at the time and looked every part of 16 or less. I was playing in a rock band in a pretty big (couple thousand seat) club as part of the opening act for some older "has been" rockers. She was there alone and pretty much seduced me. We watched the headline act together and she bought me drinks (I was not old enough to drink). Other grown men would hit on her as well. She was a nice looking, very fit and very petite woman - just how I liked them at the time.

We danced and made out that night and made a date to meet the next day. I drove to her town, met her at her apartment for our lunch date, and we never left. I fucked her a couple times, we napped with that new lover feeling of bliss (or at least I did), and we woke up and fucked again. Beautiful woman, wonderful experience, great fuck with my first woman and first MILF. The fucked up part was that she had a 13 or 14 year old kid (basically my contemporary) who came home in the afternoon and who kept coming into the bedroom while we were waking up from our nap, and who was in the next room when I was fucking his mom like a rock star. The kid wanted to hang out and be buddies after I fucked his mom. It got really weird in the end. She gave me a pic to remember her by, which my now wife found some 20 years later and made me throw out. I would have totally scanned it and posted it for you guys.

So Cornish, I am 42 now and she remains to be the oldest woman I ever fucked. But a answer of 38 is not very impressive unless one understands that she was twice my age and old enough to have been my mother. I still think of how she adored me and pampered me and treated me like a rare treat. I felt like a rock star . I gained confidence beyond my years, grew out of the ugly duckling phase, and pretty much started a twenty year non stop shag fest for me.

@Crankdingo - you're 42 and haven't EVER fucked anyone over 38?

Dude, you are leaving a lot of sweet, succulent mature pussy on the table!

I'm your age, and even though I get fewer 20 year olds than I used to (though I do nail some!), I have to say that a woman in her 50's can be mind-blowingly confident and uninhibited. Tight flesh is great, but give me enthusiastic sag 9 times out of 10!

Nope, xxxeno, 38 was it. My wife is 35, so in a few years i may top the 38 mark. Aside from a few short lived romps here and there, I have pretty much been hitting the same pussy for the last 13 years. If I had stayed single through that time I surely would have been with more milfs. I see older women in their 50s that I would put the root to if my life circumstances were different. But face it guys, when I was in my twenties and earlier thirties I was tapping the young teen and twenty-something hard bodies, as most of is would prefer to do now if we could.

She was 64 while I was 57. Biggest clit I ever saw in person too. It was as big around as my pinky. Sorry, no pictures of that evening.

More detail would be nice, do tell

I will probably be shot for postin this but hopefully she will never see it I was 31 she was 52

Thanks for the photos!
 

She looks like a lot of fun! Tell us the details!!

Not a lot to tell. It turned out to be a one time affair -- I got busy with work, and then I moved. We met online, but we lived near each other. She was divorced, and from the sounds of it, her ex was a mean jerk. Anyway, when I met her she had made a lot of swinging friends, and she had a few photos to document it too. In one she was getting it on with another lady who was in her late 70s. Our evening started with wine and cheese, then we looked at a bunch of her pictures, then we headed upstairs for the bedroom. It wasn't real eventful, but she had a few toys we played with, including a pussy pump. Her clit was big on it's own, but got really enormous when she pumped it up. It didn't stay engorged like that for very long though. What I also remember is she was a lousy kisser, but she gave an awesome blow job.

Here are a couple pics of her that she gave me. When we fucked she was larger than the picture of her on the beach, but not so large as the one of her on the bed. She said the one was taken earlier, right after she got divorced. After she got divorced she made an effort to get herself into better shape.

I am now in the very early thirties and I recently had a one night fling with a very handsome and strong man in his early 60's. I was traveling alone on business at the time. He had children my age and slightly older. He claim to have bedded other young women and that it not so uncommon for him. He was abnormally handsome so I believe that and a very good lover. He must have the 12 hour viagra as he fuck me with very good mix of tenderness and power and duration at night and wake me up with the mornning wood. I am thiking of him to be a long distance bull in a marriage that has the cuckhold or as you are sayig hot wife features. So now if other things are right I have no age limit I am supposing.

So Ms. Sonal, are you full on swinging now? I have followed just about every post from you. I think of some older handsome brute bedding you and you exploring a new lover and ot makes me jerk off every time. I would relish any additional detail or pic that helps the imagination. I also have sime of you that you first posted when you had an album that I would love to repost.

A few years ago, I must have been late 40's, I met a lady friend, she was 76, on the internet
She lived close by, and we caught up a few times for a coffee
I am married and she didnt want to have sex with a married man
with our cuddles each time I got a bit further
First just accidently touching her tits, to handleing thm firmly thru her clothes
on one visit, I managd to slip my hand inside her bra and felt her tits in the flesh
A few visits later i had her topless
i lost my shirt too

Then each time i had her topless
eventually getting her just in her panties, naturally I dressed the same
A few visits later i had us both naked and finally got to suck on her nipples

I think a couple of visits later i got to bold ,and i finger fucked her, god how i loved making her cum
trouble was, i crossed her boundary and she wouldnt let me back
I think I should have fucked her that day, that was a regret
i love a older woman

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

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.

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.

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.

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!!!

66 when I was 24
 

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

Older woman
 

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.

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

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

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