Just a "Meh" Experience
 

I was 28 and she was 42. In the late 1980s we met at a local singles group (pre-Internet) that put notices in the free advert sheet that came out every week. We talked while having brunch a couple of times. There wasn't really anyone in my age group- mostly older like her. Eventually she talked me into coming over to her place after dinner. I say that because she wasn't actually very attractive- definitely horse-faced and dumpy body shape. Very nice boobs, actually - not huge but a great handful with large (and quite sensitive) nipples. But, I wasn't getting anything anywhere else and thought what the hell - give it a shot.

Anyway we lay around her living room while we watched a couple of (regular) movies and I drank beer. She steered the conversation toward sex, and to the point of showing me an adult mail-order catalog that she regularly got that had all kinds of toys and sexy things and movies (on VHS, of course). She pointed to a pic of a dildo and said something like, "That one is mine."

Holy crap, it was HUGE. It was supposedly molded from a guy who went by "Jeff Stryker", a porn star of the 80s. The next thing I know she scampered off to her bedroom and brought out "Jeff" to show off. She talked about how sometimes it hurt her to fuck herself with the dildo and I advised her to get the usual lube from the drug store. She was like, "Wow- thanks!" Apparently it never occurred to her?

In time we started kissing and she was grabbing my cock through my shorts. I don't think she was getting much action at the time, either, so she was happy to latch on. We made it to her bedroom and she kept the lights off, with her master bathroom light on to give us a little illumination.

Well, not the most stellar sex ever. Like lovethempuffy told us, lots of enthusiasm but no skills per se. Nice to be in her mouth but couldn't stick with any action long enough. I loved playing with her tits and she definitely enjoyed. I don't recall the 'blow-by-blow', so to speak, too much but when I entered her it quite a disappointment.

I am not small but still was no match for a pussy that had been abused by ole "Jeff" for who knows how long. To be fair, I was more used to the grip of my hand than a pussy at that point in my life, but still. She had a great time because I banged her in every position she wanted to try. She was the first I experienced to actually get on top and pull her legs up into a squat and bounce up and down. Still didn't work. I know she came a few times but I never did.

We got together a few more times with largely equally unsatisfactory results. She came to my place and watched a bit of decent 'couples' porn with me. We got naked and masturbated together on my couch but she wanted the D so after a bit she stood up and turned her back to me and sat on my cock and bounced on me while we both continued to watch the porn. I really gave her nipples attention then and she just about came from that.

The only time I came was with us laying on her living room floor and making out while she tried to suck me off. Just like lovethempuffy related, she was not Ginger Lynn, and in time I just jacked it off while she licked the head and then had me shoot in her mouth.

In retrospect I was at a bad place in life then and not overly thrilled with women in general. She really didn't get a fair shake from me. I wish now that I was paying closer attention and appreciating what she did have to offer rather than just focused on the negative. Both of us definitely would have had more fun. She got married to some pathetic bastard a few years later and if she's still alive I think she's quite happy.

Five years ago we were on vacation at a beachside cottage. The cottages were directly on the Gulf Beach and wrapped in a horseshoe around a pool. We had arranged to meet a local couple on a online swinger site and sat around the pool drinking and grilling. The lady was super hot and sexy and looked maybe 50 but said she was 68. She had pert little breasts with rock hard nipples and an amazing tight ass and great legs. Her hair was colored blonde and below her shoulders. There was a definite attraction and chemistry between she and I.

Her husband looked every bit of his 65 years and there was zero attraction to him on my wife's part.

The lady and I ended up in the pool naked and then fucking in a pool side open cabana bed. She was a fantastic lover and one had one of the tightest pussy's I have ever had. She also had a very fresh and clean smelling pussy when I went down on her and she could suck cock like she really enjoyed it. My wife and the husband sat at a picnic table talking the entire time.

I have not ever met or seen a lady of her age that looked as good as she did but if I found one with her looks her age would not matter.

When my ex and I broke up (at 48), she was fucking a 28 year old. I couldn't figure out why this young guy would want her. We had these late night sex texts, and I asked her why this dude wanted to fuck her like 5 times a day. She told me, "you idiot. 28 year old girls have no experience. They are all 'hot dog hallways'. He knows I have had every shape and size, and work hard to keep my muscles strong and contoured." After we got back together, I knew exactly what she meant!!!

No Limit :-)

I had wanted to fuck a woman born in the 1800's but never got to & its too late now.

I would love to fuck the crap out of Betty White ( Better rephrase that as at her age I might Literally fuck the crap out of her LMAO)

Old
 

I was 26 and she was 84 and my bosses mother. She was stand reluctant at first but once I was sucking her nipples she turned into a porn star and to this day she was the best sex in my life. So tight wet and made me fuck her over and over. Can not believe 84 year old granny could fuck like a kid. No one ever found out about us but her old saggy body did it for me. Just to give this old woman the last sex in her life was such a thrill for me

My sister's sister in law is early to mid 50s and is HOT! Met her for the first time last year and spent the next few days thinking about her whilst jerking off.

I slept with one who told me she was 65 but I think she was 70 as I looked her up on the electoral roll.

She didnt look her age and I was 40 at the time, I always had a granny fantasy so when I met her i just went for it and she would come over and stay at mine at weekends. She had been married once with two children who were older than me. She had only every been with her ex husband so I was only the second man she had every slept with but she wanted to make up for lost time. She let me shave her pussy which was the first time she had ever been shaven, she did anal, loved giving blowjobs which she had never done before. I would buy her sexy things to wear and she had a great body but it was never more than a sex thing and after a while it just fizzled out and we lost contact.

Good News Young Guys!
 

So far, it was a grandmother, mid 50s. How old will I go?
First...young guys, I get it. I know that for you, anything above 40 is a helluva novelty for ya. Well, here's good news for you. Sex is not an Olympic Event. There is no age at which one must consider retirement. Young women are beautiful. Wonderful. The good news is, the older you get the more you appreciate the beauty and wonder of the older ones. Your brain matures. You'll reach a point where you'll enjoy looking at the young ones and having a fantasy or two...but you won't want to hang out with the vast majority of them. Once they open their mouths and words come out, you'll realize there's nothing there you want beyond pussy. Mentally, they're out of your league. You'll want someone around you that you can relate to. More good news...pussy tastes just as good, be it 20 or 50. Your cock will be just as happy inside a grandma as it would be in a young babe. Take comfort in this, because one day you'll be carrying some extra pounds and wrinkles...a little gray in your beard. You'll become largely invisible to the age group you're focused on now. When that happens, young guys, if you're not an asshole, you'll still find someone to love you, and it will be very enjoyable. Meanwhile, enjoy the young flesh while you can...and if you find a cougar looking for young dick, go for it. She'll make you a better lover and maybe a better man.
How old will I go? It depends on how old I live to be.

In my late 20's and 30's I often went with older married women often with the husband present. On average the age gap was 15 - 20 years. I think one or two might have been 30 years older. They were still fine f***s

My oldest was around 45 when i was around 18+.
And well, any age will do if i find the woman attractive, i have seen stellar 65year old's and unattractive 18year old's and vice versa. It kinda doesn't mater as long as there is a attraction.

New member here and really enjoying reading some of the stories here. I guess I stumbled upon the perfect thread for my first post.

I am 29. Honestly I cannot remember for the life of me the last time I dated a girl who was relative to my age. If I had to guess, I must of been 25 or 26 when I dated a few girls who were around my age and younger. That was the time when I had said screw this and went back to dating up. (At this point I had dated a few older women and had a few one night stands.)

For me, it all started with a family friend who I was strongly attracted to. I have known her personally since I was about 10 or 11 years old. My parents would send me over seas to my home country for the summers where I would stay at their friends house. I remember as a teenager she was very sexually open and always made a lot of sexual innuendos. I doubt she though of anything sexual of me when I was that young but I always found her fascinating, great body and a pair of really great natural boobs. Needless to say, nothing ever manifested of this.

I had a high school sweetheart who was a couple months older than me. By college we had broken up. I didn't really date a whole lot throughout college - just too busy with studies and just had a really bad perception of all the college girls I had met. To remind you, I am European. I was brought up around the European mentality even though I had grown up here in the states.

When I was 21 going onto 22, I was on a study abroad program in my homeland. I met a lot of girls on this program. I mean a lot. I was the guy who went out with a different girl about every other night. All the girls were around my age or younger. All the girls I went out with and had fun, none of them did it for me except for the girl who was 10 years older than me. She was 31 years old and shortly going onto 32.

During the program, I got a few blow jobs out of her but never fucked. Not until a year later. We kept in touch through the year and she ended up visiting the US. This turned into a 5 year long, long distance, on off relationship with many ups and downs with a lot of life lessons regarding how manipulative women are - but that is a whole other story. Frankly I was hooked on dating up and older girls. When she and I had broken over (of the 3 or 4 times) I would do online dating and would dating women older than myself. Typical range was 12-20 years older than myself. My ex and I got together again in 2014 and tried to make it work since she had moved to the US permanently. Unfortunately, after 9 months of her bullshit, I got tired of it and we mutually went our own ways.

I went back to school for a semester for a certificate program. Didn't really date but met with some girls for drinks over the course of 4-5 months. It was the perfect remedy for the breakup. Stay busy learning what you love and have fun in a city I love.

When the school program ended, I was heavily looking for a new job in a slightly different field two years ago. I was still at my old job when I met my current gf. She was my client. I kinda assumed she was older than me but I didn't think she was that much older than me. She looked no more than 35-37 years old. Without going into too much detail, there was a mutual click between us. Ended up asking her out. Over the next couple months, I'd ask her age and she would never give me it. Eventually it came out after like 4 months of dating. She is 20 years older than me and doesn't look a year older than me. People actually think I am older than her. We have been together for two years. It has been a tough two years as life is not always perfect but there is something very sweet about her that is hard for me to move on - to be with someone who would be more appropriate in age for me even if she were to be 5-10 years older than me. Very much in love with this one and I'm happy that a year ago I gave myself fully into this relationship. There have been other women with similar age gaps who I was with who just didn't cut it for me.



So...I am curious - has anyone here fallen in love with an older partner where she is/was the older one and the age gap was similar to that of my experience (20 years). What did you do? Did you marry?

62
 

I was 36 and she was 62, one of my customers. Had a dancers body and was a fantastic fuck. Was the only time. I have kept periodic contact through the years hoping for another go. There is not an upper age limit, up for trying them all LOL

63 yo ex dancer
 

To date the oldest is an ex gf 63 and an ex topless dancer. I was with her off/on 10 years and am 8 years younger. She really liked to go at it, anytime, anywhere with multiple Os. She is turning 70 this year and I might get another go at it.
I had a chance with a co worker when I had just turned 21 and she was 62......I really regret not taking advantage of her offer.

My oldest was about 70, when I was in my late 30s. She was still pretty attractive, had a full head of beautiful white hair, and a well-preserved trim body, like a dancer. Loved to fuck. After she wore me out she'd lay there and masturbate herself to another orgasm or two before calling it quits.

I ended up getting with her three or four times and it was great every time. Don't remember the details now, but I somehow lost track of her. Knowing my dumbass, I probably blew her off one time in order to get some younger babe.

71 and counting
 

I have a fairly specialist arrangement with a 71 yr old japanese lady. I am 46. How we met is a long story ... and quite a strange one ... but i have been visiting her on and off for 3 years.

She blows me for an hour or so each time. And it is like nothing else I have ever encountered. She can deepthroat completely while licking your balls ... and I am not small....

Honestly of the countless women who have sucked me, there is none even close to her.

She takes huge pride in her cocksucking skills and tells me she has a range of callers ranging from 20 to 60.

I asked her once how she started this life. She smiled and said 'my husband and i are swingers, and i just love sucking cock'

With a couple. She was early 70s, he was late 70s.
He looked like an Old Guy.
She didn't look anything like 70+... still had "it"

Lessons learned
 

When I was 19, I ended up spending dozens of wild nights, and lots of days, with a 38 year old coworker. We worked a night shift together with a work crew of about 30 in a huge department store.

She was fresh out of a long term relationship, and living alone in a huge house that she was paying little rent for to a family member. She flirted a lot working in close areas together, and over many months, the flirting got pretty sexual-as in her teasing me for being “too young/ couldn’t handle her/ etc. “

She made her hard pass at me one holiday night during a party she hosted with a majority of our coworkers. Lots of heavy drinking between everyone there and she kept telling me through out the night that I could stay if needed since she had several rooms available. Telling me then began to forcing me playfully and pulling on me to have no other option but to stay as the party began to thin out.

She guided me to the furthest back corner room into the dark and said stay in here. I stayed in the room until a few minutes later where she came in, shut the door, and pulled me in to a wild kissing session where she giggled quite a bit and was laughing at what she was doing and our age difference and how I had no idea what I was in for...and gawwwwwdammit, she was right!

She showed me, and coached me into SO much that to this day, I smile back at and appreciate her teaching me things at such a young age. She stood 5’4 with a plump butt from crossfit classes, dark naturally curly hair, and She had the biggest natural boobs I had ever seen in person...and at 19years old, I felt like I hit the jackpot. From her blowjob tricks in the shower, her riding me in the bathtub with surrounding windows, to our marathon nights of multiple positions and orgasms, those were times I will never ever forget.

It is interesting how as we mature older women look better and better. I am 39 and find an in shape 45 year old more attractive than what I would have considered a 10 at 18. I am married and not available but IF I were in an open relationship or single I am not sure how old I would go. At this point in my life there are some women I know in their mid 50's that don't look half bad. The oldest I have been with is my wife at her current age of 37.

The woman I have been with that is older than me with the biggest age gap is about five years older than me (now 44) but she was 23 or 24 the last time we were together. She still looks amazing and I see her from time to time as she is my best friend's older sister.

I wasn’t getting any action so decided to sign up to a dating site made specifically for hooking up, and after a while I came across this woman in her late 60’s close by and thought why not. I replied to one of her blog posts and we got chatting. A while later we met up at her place and fucked her hard. I was in my late 20’s at the time just before COVID hit.

I dunno what it was about her but she knew how to make me hard in my trousers just by rubbing the top of my leg and crutch. I’d grope her tits and kiss her while she rubbed me hard. She’d then take her bra off so I could suck her nipples as I pulled my trousers down for her to wank me off. Sometimes it’ll just be her tossing me until I cum, other times I’d lead her upstairs and fuck her until I cum inside. She loved to be fucked from behind while I held her sexy wide hips. Really need to hit her back up when I’m not at work one day

Possibly my favourite subject!
 

At 13, I really fancied my girlfriend's mother! To me, the original MILF (even though the term didn't exist back then!). Didn't help things when she came down from a bath just wrapped in a white towel. I never got over that!

Before I left school, I was having a thing with a friend of my mother. We never had full sex but we had a lot of fun!

After I left school, I was fortunate to have a very attractive 59 y.o. woman at work let me fondle her tits while she played with my cock (oh to get that hard again!).

My first time was with a woman who was 34 the day before I was 17 - and out little soiree took place in two months before that (completely legal here in the UK!).

At 19, I had a wonderful fling with my ex's 39 y.o. sister-in-law. Hot as hell and 40 years later, I still would!!

When I was 20, I moved in with a woman 13 years older.

At 22, I was having another 'thing' with a 39 y.o. - gorgeous little dark thing with huge tits!

Most of the ladies in my life have been older than me but the most enduring has to be Amelia. She walked into work when I was 36 and she was 53. We've had the most amazing fun whenever we can and I've posted photos of her all over this site.

She still gets as wet as any younger woman I've ever known - even now! She loves cock, cum and what I'd politely describe as 'firm handling'!!

I'm 60 in a few weeks, she's 76 and her latest set of selfies arrived in my email this morning - yum!! There's one with this post.

Wrong woman
 

I was at a small club and there was a drop dead blonde, maybe in her later 30s, slim body, long sexy legs. I managed to join her and her friend, a pleasant 50ish gal, slim, short with a nice ass. I was 23 at the time and a single serviceman that worked until midnight, then would shower change and hit this club to pick off what I could by bar time.
I was making good progress with the blonde, grinding to slow music, feeling her ass on the dance floor with her pushing back against my hardon. Walking back to our table her BF showed up and boom she was gone. Her friend laughed and said too bad. I took her out to the dance floor and started over feeling her ass was even firmer than her friends, and rubbing bellies to the point I almost nutted. We went back to the table and she said she had to get home to pay her babysitter and that she had to get to bed. When she stood up to leave I thought what the hell and gave her my best goodbye kiss. She smiled and said its a shame you're not 20 years older. I kissed her again and she smiled and told me to follow her home. I waited outside her house until the babysitter left.
When I entered she took me by the hand and I followed he to the bedroom and kissed her again passionately before moving on to her ears and neck, while reaching behind her unzipping her dress. The dress fell to the floor and I moved on to her small 34b breasts, playing licking and biting her nipples playfully until it came off. I dropped to my knees and pulled off her red bikini style panties. She had a modest bush that was well trimmed (this was the 80s) she pulled me up and to her bed saying she wanted my now. I quickly stripped and climbed on top of her in the missionary position and started to slowly enter her as she was dry, she wrapped her legs around me and pulled me into her, dry and all, and started to pound herself upwards against me. She began to juice up and moaning like crazy kissing me and continuously shaking. I felt her orgasm with her clenching my penis with her kegel muscles, I continued to try and thrust with still wrapping her legs around me. She finally unwrapped her legs and I began to do deep hard strokes in and out of her amazed at how wet she was, as she came again, and again. I finally could not hold it any longer and thrust in as far as I could feeling my own body shake with my orgasm. I lay on top of her and she told me she had not been with a man in seven years and it was wonderful, now leave. I don't want my children to see you.
I saw her at the same club a few times after that, and when bar time came if I hadn't found anyone else, took her home always to straight missionary, no oral either way. I met my future wife at the same club and Marie talked with her in the club's women's bathroom, telling her I was a 'nice guy.' Much later I told my future wife, Marie and about a dozen other regulars in the club had been intimate with me. Then told her I had no secrets and proposed to her.

How old.
 

Well 10 years on from original post time for an update, we had our last M F M threesom 7 years ago with a 53 year old guy the wife met in a chat room, after that she said enough was enough, no more playing on the side, our sex life carried on normal untill we were 75 then things really slowed down, we are now 80 and have not has sex (as in full on sex) in the last 2-3 years, age and health problems have caught up with us I am sad to say.
But all is still good, we are lucky to have got where we have got and to have survived / enjoyed almost 40 years of swinging, swapping, M F M THREESOMES and hot wifeing, we will celebrate our 60'th wedding annerversy in Febuary next year, which is not part a bad effort in this day and age, and we are still very much in love.
Thank you all for the sexy replys, made for some interesting reading over the last 10 years.
All the best rick181au.

If a Bo Derek opportunity presented itself...I wouldn't care what her age was!

She's 65 now and I couldn't agree more:

Here's some info on her and one of her most famous pictures: https://www.babepedia.com/babe/Bo_Derek

I'm guessing mid to late 70s.

I have no age ceiling as long as the woman is physically able to have sex and mentally sound to consent, if we connect I'm going for it.

when I was 23 I was banging a 32 year old mother of four. She had an abusive husband and out of the blue she asked if she could talk to me in her car. She asked if she could kiss me and I agreed. It took her about 30 seconds to grab my cock and started giving me the best blowjob i've ever had. we hooked up for a few months and then she announced she was pregnant from her husband, which I doubted but certainly went along with.
She is 70 now, with another man, but i wonder about that fifth kid. Could he be mine?

Love this thread
 

I was surprised how much I've enjoyed these stories the last few days. Great thread. I e been noticing much older than usual women since I stated reading here. I think I'd love the chance to have such a different experience with what seem to be surprisingly sexual women. Great stories. Keep them coming!

It has to be my MIL, but she won't say her Age!
 

There was a time after my wife's dad passed away that her mom went into a slump, she didn't want to go out or do anything like we had always seen her doing!
My wife and I talked to her and tried to take her out and enjoy life to its fullest, cause her hubby would have wanted it that way too!
I guess my wife did some talking to her mom on the side and told her that she is still Hot to Trot! She even went as far as telling her that I get excited over seeing her, besides wanting to enjoy her without her clothing on!
I guess it finally sunk into my MIL head and she came over our house to use the Hot tub, but she asked my wife to go out shopping for a few Hours and that surprised my wife too!
I was watching TV when my MIL called for some trouble with the Hot tub. When I got into the room she said the jets weren't working and the water was still. I could see that my MIL was Nude in the Hot tub and I finally got to see her huge Busty charms as well as her Bushy Beaver!
While it was hard to take my eyes off of her, I seen the jets weren't turned on so I did and they worked fine!
My MIL told me thanks and asked if I wanted to join her in the Hot tub, but I would have to be Nude too!
It didn't take long for me to agree on that, but it was when I started to strip in the same room that I forgot Who was in the Hot tub? Normally I don't care about exposing my growing erection to the other women, but my MIL was a different story! She might have noticed my delay, but told me that I might have a harder cock before we're done or out! I can say that she started the groping and I just followed her actions, now I know how my wife got her training so good! She was willing to do oral on me, but she told me that it'll be another time before we go all the way! It was thrilling for me later to tell my wife that her mom was super huge on top with everything and that she does have a furry Beaver that could use a bit of a trim too! Then my wife knew what her mom had on her mind when she told her to go shopping and came home in a few hours, we both laughed and it was now SEX time with my wife~
I'm not sure on my MIL age, but I wouldn't ask my wife cause she'll tell her and I don't want her to think older!
;)

Granny
 

Been sleeping on/off with a Woman 21 years older then me , last time we slept together she just turned 86, First knew her as we worked in same place, I was shy, other more bold blokes tried and failed , I was always polite and respectful to her and despite the age gap she agreed to a date I was 24 she was 45, and we slept together, my first Milf , despite my willingness and determination, she told me to find someone have some babies and find out what life’s about, she moved away, leaving everybody surprised, tried so hard to find her but failed.After a bad work accident I took early retirement, and I re found her and at her age 77 me 56 we started sleeping together again , but a few years ago she started to refuse my visits and stay overs , and she got so ill , I held her one last time , and she said ‘ It should have been us !’ She turned my proposal Twice back in the day, and she said it was because she couldn’t have any more Children but she always loved me, the family her son knew about me I sat at the back of the church away from everyone, her ashes were scattered in the sea but I managed to wet my fingers dip into the urn , and quickly swallow some of her ashes, so in my mind , at last we are together at last, and what ever happens she is with me forever more 🙏🏻🙏🏻🙏🏻

Role Reversal
 

And the opposite situation ? Our In-Laws, both aged about 40, and stoney broke. Our Father-in-Law was a Taxi Driver aged 75. He was slowly recovering from a serious Traffic Accident, when both his legs had been broken, leaving him walking with a limp. Now, after a Regular Weekly Job, he'd call to see his Son. Realising their plight, he would leave £20 on the coffee table when he left. She no doubt felt "obliged", so now when he called she'd sit him in his "special chair" in the bay window, and Son would vanish up into his Office. Then, she'd slip her top off, giving him "deep thigh massage", his sperm ejaculated into his "Y-Fronts" and causing grief when washed by the Mother-in-Law ! Soon this became £50, and she administered a "Deep Breathing Massage" Blow-Job. This advanced to her sitting knickerless, legs wide apart on the carpet, her tits massaged as he came. Latterly, she stood naked, legs astride over his lap either facing him, or from behind, her tits grappled and kissing with deep tongues as he shot his load wherever he chose. After about 5 years, he gave up driving, and their house was re-possessed.

Right now, 75, but it goes up a little every week or so.

I think when I first became interested in girls and women, my focus was all of those from my age up to about forty.

Half a century later, my focus is about forty up to my age.

The biggest age range in my relationships is from a young woman 24 years my junior to another 18 years my senior.

56 and counting
 

My current partner is the oldest woman I have ever been with…. As far as perspective I’d aim lower or higher next time. The menopause trip can be wearing on everyone involved.

As a 18 ish year old kid my buddy and I got picked up by a couple 40 something cougars at the bar…. That would be an eye opening evening for us both. But that’s the largest spread (both figuratively and physically) I’ve had to date.

Party was interrupted and we had to skat in a hurry…! Lol - story on my life on sexual adventures…. Shootin a little to close to the hip I guess.

Oh Carol
 

The oldest woman I had slept with was to mother of one of my friends - I was 22, and she was 45.

We kept the relationship secret for a few months, but were caught out when a friend of her son saw us together and mentioned it to her son.

After that we were open about the relationship which lasted around 18 months in total.

She is going to be 83 years old and I still want her, we kiss regularly, she always dips her panties and enjoys loudly, I love to hear her moaning.
For photos: PV