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

[xXroninXx]

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.

[Gin01]

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?

[bladesfan1725]

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

[hereinaz]

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.

[Leviticus59]

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.

[dftemp]

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'

[Timbo]

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"

[Summer120]

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.

[chuckfinly]

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.

[Bigcroydonguy]

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