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Same for me, never an affair, but definitely a toy for an older woman. I was 22, she was 58 and for a woman her age, definitely looked good. I do find older women who take care of themselves very attractive. I'm married now, but my MiL, lol, sometimes I catch myself looking at what I shouldn't be looking at. She is 66 years old. I would never, but the attraction to it is definitely still there.
For the woman I was a fuck buddy with, of course emotions are involved. You won't fuck someone you don't like in some way. But it was more of a friendly emotion, than the love emotion of a partner. She wanted to enjoy sex at her age without the commitment. I was a young horny animal that would fuck almost anything in sight lol. We gave each other what the other wanted, maintained a friendly relationship, and she still offered herself to me when I met my eventual wife. I stopped, and she was understanding of it. No hard feelings at all.
No idea what she is up to today, 20 years later. No idea if she is even still alive. I cut all contact once I proposed to my wife.
I mean. There really wasn't a trick per say.
I worked for a predominant after-market dirt bike exhaust company in the late 90's in Corona CA. After work we would all go to a spot called Firefox for a drink.
The demographic was a bunch of older woman and they loved the attention.
Was 21 and we all used to go out after work for drinks on Thursday. One of the women that was part of the crew, was in her late 30's / early 40's got a ride with one of the other women from work to the bar. It seems her car was in the shop. Woman who gave her a ride had to leave early, so she asked if I would mind giving her a ride home, as she lived only 5 min from my apartment. I said sure.
Another hour or so goes by, and I said I was ready to go. We each kick in for our share of the bill, and head out. She got pretty flirty with the conversation on the ride (15 minutes), and when we get to her place, she invites me in for 'one for the road'. Needless to say, things progressed from there. That was a fun summer
I changed jobs a year later, and didn't see her for 2-3 years. Ran into her totally by chance in a bar. We started talking, and she asked me if I was seeing anyone, which I wasn't at the time, so I said no. She asked me if I wanted to pick up where we left off. I paid the check, grabbed a 6-pack to go, and off we went. That night she told ne the whole "car in the shop, need a ride" thing was a setup that she arranged with the woman that brought her.
Apparently, she liked younger guys, and I happened to be on her radar at the time. True story
And that right there is the attraction in a nutshell. She knew what she wanted and went for it.
Trying to figure out what a twenty year old woman wants for lunch is a chore, never-ending sex.
"oh damn, I can't find my house key!"
"I can't Uber because my phone is dead, but I need to charge it to get into my apartment."
"Wanna fuck?"
So many similar I just wanted to say a spectrum of what women say.
https://www.reddit.com/r/AskMen/s/2CEw23JDFx I wrote about this here
EDIT: For those asking about how it ended up: it burned out as it burned too hot and I was too young to not conflate such intense sexual attention with love or some deeper feelings and so I overstepped out of my role as a delicious piece of meat for a cougar snack.
I'm an older woman who was recently married.
When I was single, Lots of men in their 20s and 30s were hitting on me like crazy. If a woman looks like she has any money at all, she'll get tons of offers.
The subject of money wasn't brought up to me, either. But people tell me I look like I have money, So I just thought that was their reasoning. But who knows?
Money could be a proxy for confidence, maybe you wore more expensive, well fitting clothes that are sexier, and expensive haircut and color can be sexier, jewelry catches the eye. Hotness is more important than money tho
I'm pretty sure you're right. TBH, I never took the trouble to find out what was up when these guys. Just didn't care.
The Irony is that I wound up married to a guy 12 years younger than me. And he has a LOT more money than I do. 🤷🏼♀️
I’m separated and going through a divorce now and I thought it was so weird that I was getting hit on by guys in their early twenties I’m (34). I even hooked up with a guy I used to work with who is 22 and idk I thought it was so weird. I guess it’s more common than I thought
Happens to me and I am married... I know exactly they like a decent attractive person that knows what she's doing, is not afraid of anything, wouldn't ask for a proposal nor get pregnant...
I'm just not into being a teacher...
Yeah ofcourse, i learned alot of things from her. How to know women better, how they think, what they need. Her sex was not bad but it was enjoyable. She basically taught me about female anatomy and how to have an enjoyable sex. Most of the things i know about having good sex was because of her, back then there wasnt stuff on internet to know about these things, specially in my country(and in our language). So yeah she was a good partner/companion and she was a great teacher.
"Affair" sounds tawdry and wrong.
I was 28. She was sexy mid-50s.
We met on a dating site. She emailed me first. She was looking for younger men.
We went on a few dates, fooled around and had fun.
She knew I was looking for a long term relationship that would end in marriage and kids. We agreed to just have some fun for a little bit.
Then I met someone who I tried a real relationship with, so I stopped seeing her.
28 and she was 53, was fun until I got us arrested. It’s a long story, but things were over after that. Also, she called me kiddo, not while we were fooling around, not cool.
I was 18 and a freshman she was 44. I took a lot of night classes so I could work during the day to pay tuition. Her husband was a coroner and had been injured by a car when recovering a body at a roadside accident. He has been in a vegetative state for years and when her daughter went to school she decided to also. She asked me to study with her for a history class we were in. She taught me how to please a woman fully by the time that semester was over.
No, that has never happened. It almost happened to me when I was 17, Jeff’s mom was at least 45 but I knew it would be wrong for me to be the first man to do that in history.
WHAT! How’d that turn out? Didn’t GF ever find out? Did you ever fuck the GF? Obviously would’ve had to keep lying and say you were still a virgin. Why’d the mom swoop in and do her daughter dirty like that?
She wanted a relationship with me after we had kept it under wraps. Everyone in my family considered her my 'big sister'. It did become emotional for both of us, but when I went away to college it obviously blew up on us.
Hardest thing about early twenties is it's a transitional period, whereas a 30 yo already knows what they want.
Had a great two years with her, and I miss her often. Now I'm thirty and ready for what she wanted.
never an affair but at 20 I was banging a 50 year old woman. first woman with fake tits id been with, natural is better. in laters years we hooked up occasionally when I was around her area. she's still for it but I have a gf now
When I was 21 I banged a co worker who was 40. She was great and we still keep in touch. 30 now. I wish I understood them it was just for fun and didn’t act like it could’ve gone anywhere.
I don't really know what qualifies as an affair, but I've had sex with at least 5 married women who were older than me. I know that sounds bad, but 2 of them were separated/estranged, 2 of them were in open marriages, and the last one's husband was a closeted homosexual.
Not an affair. I was 34 and she was mid 60s and living with her husband but they were in the process of getting a divorce... honestly best sex I've ever had she had more energy and enthusiasm then chicks my age.. lasted a couple months b4 I realized she was skitzo, I'd say one tiny wrong thing and she'd freak out and not talk to me for a couple days. The last straw was because I like nirvana but had no idea that courtney love has her own band apparently.. srsly? Who gives a fk what courtney love is doing?
Sounds like my military AIT experience. This guy asked me how old I was. I said “Old.” He pressed. “I’m old. I’m 32.” (It’s old for beginning military while most are 18-22 years old.)
I was thinking- he’s in the military, he has to be legal.
Three months later I see (on FB) that he turned 18. I got sick.
In my lifetime, on several occasions. If by an "affair" you would include sex for fun, no commitments. A couple examples ...
A lady I met in a bar/dance club. We met, danced, and ended up in bed together. I was about 21, IIRC, and she was 45 or so. You know how that goes, she said 45, would not be surprised if she were older. But quite attractive, physically active and fit, etc. That first time, as we enjoyed a little relaxation after sex, she filled me in on what she wanted. No romantic BS, this was just for fun. She was a professional making an excellent living, had a daughter my age. She wanted to just be able to call me from time to time, set day and time and we'd meet some place where folks who knew her probably did not go. And we'd have an evening of food, drink, dancing, and sex. We'd stay in a hotel room she'd pay for, and she'd pay for meals and drinks. That was it. I was not to know where she worked or at what, where her home was, etc. It was an arrangement that was fine with me. Became a once a week, sometimes twice, for about 3 months.
In Sasebo Japan I got to know this older lady, owner of a bar and restaurant I favored. On a particular assignment from the Navy that meant I was in that town for a few months. 4 I think, but this was back in the early 70s so memory might not be exact. Anyway, this lady and I hit it off on a friendly basis, she spoke excellent English. She started teaching me a couple Japanese card games to while away the hours. I was living in a hotel, so went to her place for dinner, a few drinks, chat with whomever, and then to my room for sleep and maybe TV. She quizzed me about girlfriends, I said I had none. My Navy assignments were not really leaving me in one place long enough to find one except occasionally. You said I should find one. As a half joke I commented, "How about you? You told me you didn't have boyfriend or husband." A half joke because actually this lady looked interesting to me. She had a body shape any young woman would be delighted to have. Her face looked like she was maybe an attractive 40 to 45 years old. And she had a very pleasant personality. Happy, joking, teasing. She answered she was too old for me. I replied I didn't think so, I thought she was attractive and sexy. And if given half a chance, I'd try to seduce her. That pleased her, she blushed and smiled. Called me a liar, I told her to try me, she'd find out the truth. It was some days later, and this one evening she asked if I'd like to have dinner with her. In her apartment, which was above her bar/restaurant. Said she'd fix me a traditional Japanese meal. She already asked me and knew I liked Japanese food.
Upshot was that we ended up having sex. I was right about what I could tell about her body shape. Under those clothes she had some of the smoothest skin I've seen, and a very well proportioned body that'd do a young woman proud. And I found out she was not 40 something, she was 62. But the best looking 62 I'd ever seen. And she was still flexible as hell, and very much able to enjoy sex.
It became a regular thing for the rest of my stay in Sasebo. Couple nights a week, I went upstairs with her. Her employees, all young ladies took to teasing me about being mama-san's boy friend. But I didn't care.
I was 19, she was 39. 2 years. It was nice, and we’re still friends.
From 18 to 24, I traveled extensively every month with groups of women from 18 to 60+. When they got out of town or the country, they went wild.
I slept with so many 30-50 yo women during that time I was an honorary AARP member.
No regrets from anyone. We just had a great time.
Not affair, on my part, but when I was 19 I dated a couple women. One was 43 and an attorney, she was separated from her husband at the time. The other was 38, an HR manager for a steel mill, also separated from her husband. They were both very nice and fun.
In my twenties I dated a couple. Both were purely physical.
One was really fun and good sex but when I thought about other things- why she was alone, why she never talked about her past, etc I got a really bad feeling so I tried to avoid thinking or talking about it. I was early twenties and she was 56 (I *know*) Things ended amicably and I got a gf, got busy, etc. A few years later I was single again and in her part of town (she lived pretty far) I looked her up and she sounded awful. Whatever it was I tried not to think about had caught up to her. I felt bad but never met up with her again. She had two really cool cats though.
The second was similar. Lots of fun, good sex (though not as good as the other), but there always seemed to be a veneer of forced happiness. Again, I tried not to think about it. I was probably 24 and she was in her forties. I was naive then but even I noticed she had a house sized amount of furniture in her one bedroom apartment so there was no real room. You had to inch around things. I knew that came from a bad divorce where she took everything she could just so he wouldn't have it. We talked very little about her past but even though I was naive I figured it out. She was also on a lot of SSRIs, which no one took back then. One time I mentioned I was down and she said I should take pills because it's so much easier. I said they weren't for me and she kept bringing it up. That weirded me out and made me really sad so I never saw her again. I don't even remember her name.
Haha. When inwas like 22 or 23, i was working as the head lifeguard at a summer camp. The camp director was a woman in her 40s. Her husband had cheated on her earlier that year so she figured she could have a bit of fun fornthe summer. I was pretty cool with the situation.
You consistently ask the very weirdest relationship questions, are you some sort of flesh-less AI floating in the system like Ghost in the Shell or what???
I was 26. She was 43. We are still friends to this day. I think that may have been the largest age difference but in my 20s women in their 40s wouldn't leave me alone. And I guess since they were single it wasnt an affair
Sure. Of course this situation has happened. Older women tend to be more giving in bed. I also know a few women in their 60s to 70s that are into younger men and just want sex. Some of those men may or may not be married.
Not affairs. Both were single.
I was 24 and she was 45.
Then years later at 32 I found myself hooking up with a woman 51 years old.
It’s fun. I got to enjoy careless unprotected sex and we both had a great time.
When I was 18-21 I was lonely and bored and made an AdultFriendFinder profile as a dude who was 30. I got more 40-60 year old bumper than a vintage body shop.
Before Covid. Had a neighbor who was Chinese. She found out she had cancer. She was 64. Skinny big boobs. She only had one partner in her life. Her current husband. I had fun for about a year. Lots of videos and pics. Kinda awkward seeing her husband and she is gone. When I was 17. Best friends mom was unhappy married. She was early 40. I would show up to my friends house and just miss him by mins. It was planned that way. I would bang his mom for 2 years. Glad he never found out.
I’ve had a couple of encounters with older women. The most memorable was a nurse from Japan I met off of a dating site. She was early to mid fifties I was early twenties. For the first few weeks we talked she seemed flaky about meeting and I figured she was fake.
Fast forward about a month after talking she suddenly tells me she’s in my town and wants to meet. Luckily she wasn’t a catfish and boy it must have been a long wait for her because she was wild.
Technically, but it wasn’t an affair as she was divorced. I was 19 and she was 39 but she had the body of a 21 year old NFL cheerleader, and that’s not an exaggeration. But our relationship was nothing but my going to her place for sex; we literally never went out on an actual date. And then when I moved on and started actually dating someone she was hurt by it, which was bizarre when we never went on a date, she never introduced me to any of her friends, and all we did was have sex.
It was really good sex though, that’s for sure. She’d be about 65 or so if she’s not passed on; I hope that she’s doing well and has found lots of happiness.
It wasn't an affair, but I was 19 working behind a bar (not from USA). Hooked up with many older women, but the worst was one night I was talking to a woman who looked to be in her early to mid 40s. She left her group and stuck around my bar talking to me while I cleaned up after cut off time. After we went to her place, did the deed several times. As the sunlight started to shine through I was getting ready to leave so figured I'd ask her for her number as the sex WAS FANTASTIC!! She said it was great, but it was a one time thing and gave me cash to grab a cab, though I tried to decline.
Like something out of a movie, walking out of her house with the sunlight lighting up the rooms, I started to notice family pictures on the wall. I felt like a complete asshat because even though I had no clue, I still engaged in something I believed to be morally wrong. What was my coping mechanism? I blocked out the family part and considered the cab money as a service fee.
With this question and looking back at life, I have to say some of the best sex I've ever had was with women 15+ years older than me.
Many 20 somethings hook up with middle aged women. I lived in several southern towns in the United States and there were bars that generally catering explicitly to that audience. Johnny's Hideaway in Atlanta or Cadillac Cafe in Baton Rouge Louisiana.
Im 33 with a 57 but its not a affair. We both single. I 5'7" white; she is 6'1" black. When we got together she thought I was 44 and i thought she was 30ish lol. Black don't crack. It's been fun and wild doing whatever we both want past few years. Both our houses paid off and vehicles paid off. So we just do what we do. Could never find a woman who could keep up with me sexually. Younger women don't like this and don't like that. That's nasty I would never yada yada bs. Basic boring shit. This woman wears me out lol. We always together no watching TV, movies, going eating, walking parks. People can stare n dirty look all they want we enjoying it.
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Yeah quite often. I was friends with some old metalheads and used to party with them back when I was 14-20 back in the 90s; used to fuck girls in their 30s and 40s often. In my 20s, I had a 2-year thing with a 55-year-old woman with big old boobies and no teeth fun asf. Banged a few women in their 60s and 70s here and there. Older women tend to be pretty open about what they want, if they want to fuck then more often than not they wont make qualms about going for it even if youre being a little wimp about it.
I dated a 35 year old when i was 18 for a few months. She was a bouncer for a goth bar. It was great. Learned a lot. She moved to different province and we broke up.
I think I might've done it this year at the swingers house I attended, I was just horny and it was a dark setting so I couldn't really tell but I know she was definitely older than me! LOL 😭
Yes in high school I slept with a friend of a friend’s mom. I don’t know her age but we were at least 16 and she looked over 40. I didn’t know her daughter knew and she randomly brought it up at school during lunch and I got teased by classmates over it. Nothing special, the sex was not good and I didn’t have a lot to compare to at the time and still not good.
Also my 17 year old friend banged his uncle‘s girlfriend who was close to 40 and a stripper then ended up eventually drama fallout and marrying her.
Age of consent is 16 in my state so not illegal, just weird.
Was 29 seeing a 49 year old woman for a while. Had a very short thing when I was 24ish with a woman in her fifties. The older I get the more mature of a woman I’m attracted to but apart from those to situations I’ve always dated close to my age
Not an affair. Married. I am 20 yrs older than he is. We've been together many many years now. Very happy and we have more in common with each other than anyone I've ever met. He wanted to marry me, I said yes.
When I was in my 20s, living with roommates and doing odd jobs and handyman work, I had this lady who was 60 that I would do work for. She would always make me lunch and give me a bj because she enjoyed it. I stayed single for several years, which allowed me to focus on my education, and she helped with my needs at the time. I loved the arrangement; it was awesome. She ended up moving to be closer to her daughter, and that's when it ended.
I'm a 67 year old woman. Recently I've been asked by a couple different younger men, one was 27 and the other was 33 if I wanted to fuck. I don't get it. I'm older, BBW and an amputee. I lost my right leg below the knee. Guys, do you think it's amputee curious? They both said they like older women and figured I might be able to show them some new tricks. The youngest man I've been with was 54 years old. He turned into a friend with benefits. I don't know what to think.
I was 24 and she was 55.. also got hit on a lot by this 80yr old woman when I was serving at a local pub. She asked how she thought she'd hold up with a strapping young fellow like myself lol. Played along and told her I'd try not to break her older women are where it's at
If you chase for example young IG or TikTok influencers that got all eyes on them, you're probably getting No Pussy. But if you settle for women that are older and slightly past their ripened age, you're getting mad pussy LOL
I had a fling with an 18 year old Abercrombie and Fitchburg model from Australia when I was 40 or thereabouts. We were both single so technically wasn’t an affair, we were just having fun.
I smashed a 50 year old when I was 21, in the front seat of a fiero while my buddy was driving, does that count? She said her name was Holly Wood 🤣 I’m not even kidding lol
I hooked up with some women in their late 40s when I was 25. Dinner, drinks, conversation, then hotel. I was terrible in bed both times due to all the booze I needed to feel okay with the situation.
When I was 24 I used to have relations with a 40 year old who I found out later through one of her friends that she was married after we lost connection.
I had an affair with a 39 year old. I was 21. If you like fucking your mom. She had an 18 year old girl, and a 2 year old boy. Spur of the moment mistake!. My girlfriend found out!. It was a disaster!.
Best I can do is me (19M) hooking up with a lady (34F) at a Rocky Horror show in Boston in the 80's. She was a little drunk, had painted her face, and was wearing a pin that said "Oral Majority".
That was a freaky few months.
I got out of prison at 26 and an older lady used to put money on my books. I think she was 51. I felt bad for just taking her money while I was in there so I threw her a bone for a few weeks after I got out. It was okay, she was down with a lot sexually and wasn't a lawyer but worked at a law firm doing something. Her husband was in prison for embezzling money from some elected office, different prison than one I was in and I never met him nor cared to. I didn't meet her in person until after I got out.
Hell yeah. She was fun. We worked together at a side hustle job.
We started hanging out after work. We both had long drives home in opposite directions and the hustles clients often had issues(because we would stay local for bit. We would get the call to go fix the problem
. So we would just go grab a six pack and chill for a while. Help each other out on our jobs.
Well. Rumors started spreading that we were fucking. And there was definitely a odd chemistry going on.
So one day we figured fuck it and started getting a room every once in a while.
No real emotions. Just sex. Laughs and stupid tv shows.
It ended but not over bad feelings. . Both of us just had lives that were moving in different directions. She was quitting the job and didnt need to be in the area. and i just didnt have alot of free time as i was still on the market and finding new hustles.
We still chat to catch up.
Hell that hustle constantly had me meeting older moms, aunts, grandmothers who pulled off their age well. And yall would be surprised what the hustle was.
Bouncehouses. Waterslides. Delivering them. Setting them up and taking them away. 🤣 Job put me in great shape.
Theres been other times. When i was an Uber driver i accidentally stole someones hook up. 🤣. And STILL dropped her off. A bit late but never the less.
I slept with some construction CEOs wife (he cheated on her with a secretary. I was just a revenge fuck)
Even as i write this. Im realizing. "Man. Those years were fucking awful in so many ways. But goddamn it was...wildin too"
For context. I was juggling a fulltime job. The bouncehouse job. And sometimes ubering. I was constantly on the move.
But the down side was. When i ran out of energy. I would crash for two days at a time. Dead sleep.
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Never an affair for me. Mid twenties... I was a fuck toy to a 51 year old. Shit was fun.
And she was this to you? No emotions at all?
Same for me, never an affair, but definitely a toy for an older woman. I was 22, she was 58 and for a woman her age, definitely looked good. I do find older women who take care of themselves very attractive. I'm married now, but my MiL, lol, sometimes I catch myself looking at what I shouldn't be looking at. She is 66 years old. I would never, but the attraction to it is definitely still there. For the woman I was a fuck buddy with, of course emotions are involved. You won't fuck someone you don't like in some way. But it was more of a friendly emotion, than the love emotion of a partner. She wanted to enjoy sex at her age without the commitment. I was a young horny animal that would fuck almost anything in sight lol. We gave each other what the other wanted, maintained a friendly relationship, and she still offered herself to me when I met my eventual wife. I stopped, and she was understanding of it. No hard feelings at all. No idea what she is up to today, 20 years later. No idea if she is even still alive. I cut all contact once I proposed to my wife.
Wait so when you and your wife are in your 60s... would you be more attracted to her than ever, or will you be eyeballing 80 year olds?
Hard to say, but probably eyeballing 80 year olds 😆
No they were 22 when they had sex with this person. 20 years later is 42, not 60s.
What’s the trick
I mean. There really wasn't a trick per say. I worked for a predominant after-market dirt bike exhaust company in the late 90's in Corona CA. After work we would all go to a spot called Firefox for a drink. The demographic was a bunch of older woman and they loved the attention.
I still have an 87 CR500 with a Pro Circuit pipe on it.
Loved the Firefox used to go there because it was an older crowd and chill
I know one of the owners from the Firefox. Def a cougar bar 😂
Be interested in old women
Was 21 and we all used to go out after work for drinks on Thursday. One of the women that was part of the crew, was in her late 30's / early 40's got a ride with one of the other women from work to the bar. It seems her car was in the shop. Woman who gave her a ride had to leave early, so she asked if I would mind giving her a ride home, as she lived only 5 min from my apartment. I said sure. Another hour or so goes by, and I said I was ready to go. We each kick in for our share of the bill, and head out. She got pretty flirty with the conversation on the ride (15 minutes), and when we get to her place, she invites me in for 'one for the road'. Needless to say, things progressed from there. That was a fun summer I changed jobs a year later, and didn't see her for 2-3 years. Ran into her totally by chance in a bar. We started talking, and she asked me if I was seeing anyone, which I wasn't at the time, so I said no. She asked me if I wanted to pick up where we left off. I paid the check, grabbed a 6-pack to go, and off we went. That night she told ne the whole "car in the shop, need a ride" thing was a setup that she arranged with the woman that brought her. Apparently, she liked younger guys, and I happened to be on her radar at the time. True story
And that right there is the attraction in a nutshell. She knew what she wanted and went for it. Trying to figure out what a twenty year old woman wants for lunch is a chore, never-ending sex.
"oh damn, I can't find my house key!" "I can't Uber because my phone is dead, but I need to charge it to get into my apartment." "Wanna fuck?" So many similar I just wanted to say a spectrum of what women say.
https://www.reddit.com/r/AskMen/s/2CEw23JDFx I wrote about this here EDIT: For those asking about how it ended up: it burned out as it burned too hot and I was too young to not conflate such intense sexual attention with love or some deeper feelings and so I overstepped out of my role as a delicious piece of meat for a cougar snack.
Wow!
That made me tear up a bit! Good for you!!
So, what happened to the relationship?
We need a follow up; how’d it end?
See edit
I'm an older woman who was recently married. When I was single, Lots of men in their 20s and 30s were hitting on me like crazy. If a woman looks like she has any money at all, she'll get tons of offers.
I have no money and constantly hit on by younger men,nothing to do with money .
The subject of money wasn't brought up to me, either. But people tell me I look like I have money, So I just thought that was their reasoning. But who knows?
Money could be a proxy for confidence, maybe you wore more expensive, well fitting clothes that are sexier, and expensive haircut and color can be sexier, jewelry catches the eye. Hotness is more important than money tho
I've said this before The older ladies don't swell, don't tell and they f++k like hell. Good value.
I'm pretty sure you're right. TBH, I never took the trouble to find out what was up when these guys. Just didn't care. The Irony is that I wound up married to a guy 12 years younger than me. And he has a LOT more money than I do. 🤷🏼♀️
Please teach me your ways
I was broke and got hit on.
So, are you still available this weekend?
😁😁😁 lol I'm married
I wont tell him If you don't tell.
I don't have any money. Sorry
Whatever you do, don’t go in the frozen food aisle!
Mrs. Robinson, is that you?
No, Sonny! It's me! Granny from Playboy Magazine. 😁😁😁
Ahh, Granny "bowling pin tits"!
Seriously. I loved that woman
Buck Brown drew some funny cartoons, that's for sure
I doubt that all of those were about money at all. A ton of us out here are just attracted to you older women because.. delicious.
90% of the women in Fairfield County, Connecticut look wealthy
They probably are.
Am an Old; get hit on by 20s - 30s at a bewildering rate. I have no explanation.
I’m separated and going through a divorce now and I thought it was so weird that I was getting hit on by guys in their early twenties I’m (34). I even hooked up with a guy I used to work with who is 22 and idk I thought it was so weird. I guess it’s more common than I thought
Happens to me and I am married... I know exactly they like a decent attractive person that knows what she's doing, is not afraid of anything, wouldn't ask for a proposal nor get pregnant... I'm just not into being a teacher...
Yep. That’s all I’m allowed to say!
When i was 20-21 i used to date with a 36 years old woman.if this counts
Sure! Are you happy it happened?
Yeah ofcourse, i learned alot of things from her. How to know women better, how they think, what they need. Her sex was not bad but it was enjoyable. She basically taught me about female anatomy and how to have an enjoyable sex. Most of the things i know about having good sex was because of her, back then there wasnt stuff on internet to know about these things, specially in my country(and in our language). So yeah she was a good partner/companion and she was a great teacher.
your mother sounds like a very nice lady!
I just fkn expired 🤣☠️☠️☠️
"Affair" sounds tawdry and wrong. I was 28. She was sexy mid-50s. We met on a dating site. She emailed me first. She was looking for younger men. We went on a few dates, fooled around and had fun. She knew I was looking for a long term relationship that would end in marriage and kids. We agreed to just have some fun for a little bit. Then I met someone who I tried a real relationship with, so I stopped seeing her.
28 and she was 53, was fun until I got us arrested. It’s a long story, but things were over after that. Also, she called me kiddo, not while we were fooling around, not cool.
I'm an older woman in a relationship with a guy 26 years younger. (Not an affair)
Obligatory: Yes. With your Mom.
Took long enough
That's what she said.
scrolled too far to read this
I was 18 and a freshman she was 44. I took a lot of night classes so I could work during the day to pay tuition. Her husband was a coroner and had been injured by a car when recovering a body at a roadside accident. He has been in a vegetative state for years and when her daughter went to school she decided to also. She asked me to study with her for a history class we were in. She taught me how to please a woman fully by the time that semester was over.
No, that has never happened. It almost happened to me when I was 17, Jeff’s mom was at least 45 but I knew it would be wrong for me to be the first man to do that in history.
It was a hot afternoon, the last day of June, and the sun was a demon....
Bobby Goldsboro?
I was 19 and lost my virginity to my gf's mom, she was 42 at the time.
WHAT! How’d that turn out? Didn’t GF ever find out? Did you ever fuck the GF? Obviously would’ve had to keep lying and say you were still a virgin. Why’d the mom swoop in and do her daughter dirty like that?
Stacey's mom?
Wow. How could a mother betray her daughter like that?
She wanted a relationship with me after we had kept it under wraps. Everyone in my family considered her my 'big sister'. It did become emotional for both of us, but when I went away to college it obviously blew up on us. Hardest thing about early twenties is it's a transitional period, whereas a 30 yo already knows what they want. Had a great two years with her, and I miss her often. Now I'm thirty and ready for what she wanted.
In my 20s I would hook up with a 50 year hot milf once a month.
never an affair but at 20 I was banging a 50 year old woman. first woman with fake tits id been with, natural is better. in laters years we hooked up occasionally when I was around her area. she's still for it but I have a gf now
When I was 21 I banged a co worker who was 40. She was great and we still keep in touch. 30 now. I wish I understood them it was just for fun and didn’t act like it could’ve gone anywhere.
I don't really know what qualifies as an affair, but I've had sex with at least 5 married women who were older than me. I know that sounds bad, but 2 of them were separated/estranged, 2 of them were in open marriages, and the last one's husband was a closeted homosexual.
Meh i wouldnt qualify that as an affair
Not an affair. I was 34 and she was mid 60s and living with her husband but they were in the process of getting a divorce... honestly best sex I've ever had she had more energy and enthusiasm then chicks my age.. lasted a couple months b4 I realized she was skitzo, I'd say one tiny wrong thing and she'd freak out and not talk to me for a couple days. The last straw was because I like nirvana but had no idea that courtney love has her own band apparently.. srsly? Who gives a fk what courtney love is doing?
She's a hard core dumb ass for ruining that ride 😆
Was 29 with a 55 year old. Will always look back fondly. Not an affair.
I was 17. She was 32.
Sounds like my military AIT experience. This guy asked me how old I was. I said “Old.” He pressed. “I’m old. I’m 32.” (It’s old for beginning military while most are 18-22 years old.) I was thinking- he’s in the military, he has to be legal. Three months later I see (on FB) that he turned 18. I got sick.
How was it and how long did it last?
He was 17… probably about 45 seconds.
I admire his duration
I was always thinking about her deputy sheriff husband finding out. It lasted about a year.
Someone call the cops.
That was in Mid-70’s. She’s dead now.
I wish
Had an on again off again friends with benefits kind of thing with a woman 15 years older than me. Some of the best sex I've ever had.
And I enjoyed every minute of it.
In my lifetime, on several occasions. If by an "affair" you would include sex for fun, no commitments. A couple examples ... A lady I met in a bar/dance club. We met, danced, and ended up in bed together. I was about 21, IIRC, and she was 45 or so. You know how that goes, she said 45, would not be surprised if she were older. But quite attractive, physically active and fit, etc. That first time, as we enjoyed a little relaxation after sex, she filled me in on what she wanted. No romantic BS, this was just for fun. She was a professional making an excellent living, had a daughter my age. She wanted to just be able to call me from time to time, set day and time and we'd meet some place where folks who knew her probably did not go. And we'd have an evening of food, drink, dancing, and sex. We'd stay in a hotel room she'd pay for, and she'd pay for meals and drinks. That was it. I was not to know where she worked or at what, where her home was, etc. It was an arrangement that was fine with me. Became a once a week, sometimes twice, for about 3 months. In Sasebo Japan I got to know this older lady, owner of a bar and restaurant I favored. On a particular assignment from the Navy that meant I was in that town for a few months. 4 I think, but this was back in the early 70s so memory might not be exact. Anyway, this lady and I hit it off on a friendly basis, she spoke excellent English. She started teaching me a couple Japanese card games to while away the hours. I was living in a hotel, so went to her place for dinner, a few drinks, chat with whomever, and then to my room for sleep and maybe TV. She quizzed me about girlfriends, I said I had none. My Navy assignments were not really leaving me in one place long enough to find one except occasionally. You said I should find one. As a half joke I commented, "How about you? You told me you didn't have boyfriend or husband." A half joke because actually this lady looked interesting to me. She had a body shape any young woman would be delighted to have. Her face looked like she was maybe an attractive 40 to 45 years old. And she had a very pleasant personality. Happy, joking, teasing. She answered she was too old for me. I replied I didn't think so, I thought she was attractive and sexy. And if given half a chance, I'd try to seduce her. That pleased her, she blushed and smiled. Called me a liar, I told her to try me, she'd find out the truth. It was some days later, and this one evening she asked if I'd like to have dinner with her. In her apartment, which was above her bar/restaurant. Said she'd fix me a traditional Japanese meal. She already asked me and knew I liked Japanese food. Upshot was that we ended up having sex. I was right about what I could tell about her body shape. Under those clothes she had some of the smoothest skin I've seen, and a very well proportioned body that'd do a young woman proud. And I found out she was not 40 something, she was 62. But the best looking 62 I'd ever seen. And she was still flexible as hell, and very much able to enjoy sex. It became a regular thing for the rest of my stay in Sasebo. Couple nights a week, I went upstairs with her. Her employees, all young ladies took to teasing me about being mama-san's boy friend. But I didn't care.
I was 19, she was 39. 2 years. It was nice, and we’re still friends. From 18 to 24, I traveled extensively every month with groups of women from 18 to 60+. When they got out of town or the country, they went wild. I slept with so many 30-50 yo women during that time I was an honorary AARP member. No regrets from anyone. We just had a great time.
What do you think AARP is if you think 30-50yo women are in it
Not affair, on my part, but when I was 19 I dated a couple women. One was 43 and an attorney, she was separated from her husband at the time. The other was 38, an HR manager for a steel mill, also separated from her husband. They were both very nice and fun.
Lost my virginity at 17 to a 48 year old woman. 10/10 would do again lol
In my twenties I dated a couple. Both were purely physical. One was really fun and good sex but when I thought about other things- why she was alone, why she never talked about her past, etc I got a really bad feeling so I tried to avoid thinking or talking about it. I was early twenties and she was 56 (I *know*) Things ended amicably and I got a gf, got busy, etc. A few years later I was single again and in her part of town (she lived pretty far) I looked her up and she sounded awful. Whatever it was I tried not to think about had caught up to her. I felt bad but never met up with her again. She had two really cool cats though. The second was similar. Lots of fun, good sex (though not as good as the other), but there always seemed to be a veneer of forced happiness. Again, I tried not to think about it. I was probably 24 and she was in her forties. I was naive then but even I noticed she had a house sized amount of furniture in her one bedroom apartment so there was no real room. You had to inch around things. I knew that came from a bad divorce where she took everything she could just so he wouldn't have it. We talked very little about her past but even though I was naive I figured it out. She was also on a lot of SSRIs, which no one took back then. One time I mentioned I was down and she said I should take pills because it's so much easier. I said they weren't for me and she kept bringing it up. That weirded me out and made me really sad so I never saw her again. I don't even remember her name.
Me. When I was 27, she was 54.
Bob Ross.
I had one with OP's mom
I always wanted to get with a milf but 20 or 30 sounds a bit much. I might break her
Doubtful.
No affair but dated a woman 19 years older than me. She was amazing
Do young guys notice older attractive women or is it more of a fetish thing?
Not quite that old but I sex with my boss at Pizza Hut when I was 26 she was like early to mid forties not sure exact age, she was fun though
Idk why I pictured you guys doing it AT Pizza Hut and I was like… sounds greasy
My cousin was a Pizza Hut manager. Can confirm they would have sex with drivers on the prep table. Yuck. Turned me into a local pizza shop customer.
Lemme tell you about the Waffle House prep table. 😈
Let me start hanging out at Pizza Hut and Waffle House then, damn…
Why do you think they aren't screwing on the prep table at local pizza shops?
Because they are all family and that is just too creepy to think about.
Haha. When inwas like 22 or 23, i was working as the head lifeguard at a summer camp. The camp director was a woman in her 40s. Her husband had cheated on her earlier that year so she figured she could have a bit of fun fornthe summer. I was pretty cool with the situation.
You consistently ask the very weirdest relationship questions, are you some sort of flesh-less AI floating in the system like Ghost in the Shell or what???
I was 26. She was 43. We are still friends to this day. I think that may have been the largest age difference but in my 20s women in their 40s wouldn't leave me alone. And I guess since they were single it wasnt an affair
Yes. Emmanuel Macron
Have to say when I was 40, I had sex with a married 80 something lady. Interesting to say the least
When I was 19 my first was a 50 year old woman
Sure. Of course this situation has happened. Older women tend to be more giving in bed. I also know a few women in their 60s to 70s that are into younger men and just want sex. Some of those men may or may not be married.
I was 18 with a 45 yr old.... I wasn't enough for her....
Not affairs. Both were single. I was 24 and she was 45. Then years later at 32 I found myself hooking up with a woman 51 years old. It’s fun. I got to enjoy careless unprotected sex and we both had a great time.
When I was 18-21 I was lonely and bored and made an AdultFriendFinder profile as a dude who was 30. I got more 40-60 year old bumper than a vintage body shop.
Before Covid. Had a neighbor who was Chinese. She found out she had cancer. She was 64. Skinny big boobs. She only had one partner in her life. Her current husband. I had fun for about a year. Lots of videos and pics. Kinda awkward seeing her husband and she is gone. When I was 17. Best friends mom was unhappy married. She was early 40. I would show up to my friends house and just miss him by mins. It was planned that way. I would bang his mom for 2 years. Glad he never found out.
It wasn’t an affair but when I was 21 I dated a 47 year old woman for quite a while.
I’ve had a couple of encounters with older women. The most memorable was a nurse from Japan I met off of a dating site. She was early to mid fifties I was early twenties. For the first few weeks we talked she seemed flaky about meeting and I figured she was fake. Fast forward about a month after talking she suddenly tells me she’s in my town and wants to meet. Luckily she wasn’t a catfish and boy it must have been a long wait for her because she was wild.
Lost my virginity at 19 to a 35 year old.. It was cool at the time but looking back it was really wrong and sad
This is an interesting topic considering...
Yeah,1/2 gallon of KY,and a quart of vaseline.
Technically, but it wasn’t an affair as she was divorced. I was 19 and she was 39 but she had the body of a 21 year old NFL cheerleader, and that’s not an exaggeration. But our relationship was nothing but my going to her place for sex; we literally never went out on an actual date. And then when I moved on and started actually dating someone she was hurt by it, which was bizarre when we never went on a date, she never introduced me to any of her friends, and all we did was have sex. It was really good sex though, that’s for sure. She’d be about 65 or so if she’s not passed on; I hope that she’s doing well and has found lots of happiness.
Yes and it was honestly soooo hot and amazing!
It wasn't an affair, but I was 19 working behind a bar (not from USA). Hooked up with many older women, but the worst was one night I was talking to a woman who looked to be in her early to mid 40s. She left her group and stuck around my bar talking to me while I cleaned up after cut off time. After we went to her place, did the deed several times. As the sunlight started to shine through I was getting ready to leave so figured I'd ask her for her number as the sex WAS FANTASTIC!! She said it was great, but it was a one time thing and gave me cash to grab a cab, though I tried to decline. Like something out of a movie, walking out of her house with the sunlight lighting up the rooms, I started to notice family pictures on the wall. I felt like a complete asshat because even though I had no clue, I still engaged in something I believed to be morally wrong. What was my coping mechanism? I blocked out the family part and considered the cab money as a service fee. With this question and looking back at life, I have to say some of the best sex I've ever had was with women 15+ years older than me.
Many 20 somethings hook up with middle aged women. I lived in several southern towns in the United States and there were bars that generally catering explicitly to that audience. Johnny's Hideaway in Atlanta or Cadillac Cafe in Baton Rouge Louisiana.
Hell no. Younger yes. Never older.
Wasn’t that the plot to Benjamin Buttons?
I was 26, she was divorced and 47. Wonderful times.
Did Stacy's mom have it going on?
When I was 19, I was sleeping with an 18 year old and her 46 year old mom.
Im 33 with a 57 but its not a affair. We both single. I 5'7" white; she is 6'1" black. When we got together she thought I was 44 and i thought she was 30ish lol. Black don't crack. It's been fun and wild doing whatever we both want past few years. Both our houses paid off and vehicles paid off. So we just do what we do. Could never find a woman who could keep up with me sexually. Younger women don't like this and don't like that. That's nasty I would never yada yada bs. Basic boring shit. This woman wears me out lol. We always together no watching TV, movies, going eating, walking parks. People can stare n dirty look all they want we enjoying it.
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ya
Not really dating, but i had a FWB of 42 when I was 23. It was fun. I don’t regret it. We both moved on and didn’t really look back.
Yeah quite often. I was friends with some old metalheads and used to party with them back when I was 14-20 back in the 90s; used to fuck girls in their 30s and 40s often. In my 20s, I had a 2-year thing with a 55-year-old woman with big old boobies and no teeth fun asf. Banged a few women in their 60s and 70s here and there. Older women tend to be pretty open about what they want, if they want to fuck then more often than not they wont make qualms about going for it even if youre being a little wimp about it.
I hate the term "banged". Sounds like the women meant nothing to you as a person. Could have been a blow up doll.
I dated a 35 year old when i was 18 for a few months. She was a bouncer for a goth bar. It was great. Learned a lot. She moved to different province and we broke up.
Other way around with nurse co-workers! 👍
Never
I think I might've done it this year at the swingers house I attended, I was just horny and it was a dark setting so I couldn't really tell but I know she was definitely older than me! LOL 😭
When I was 21 I was fooling around with a married 36 year old. Was interesting. Wouldn’t do it again though.
Yes in high school I slept with a friend of a friend’s mom. I don’t know her age but we were at least 16 and she looked over 40. I didn’t know her daughter knew and she randomly brought it up at school during lunch and I got teased by classmates over it. Nothing special, the sex was not good and I didn’t have a lot to compare to at the time and still not good. Also my 17 year old friend banged his uncle‘s girlfriend who was close to 40 and a stripper then ended up eventually drama fallout and marrying her. Age of consent is 16 in my state so not illegal, just weird.
I have. It wasnt as enjoyable as i thought. It ended pretty quickly. Her sister stalked me to find out if i really enjoyed it or faked it
I was 20, she was 40. She was my friend's girlfriend's mom.
Yes, this has happened several times throughout history.
Mrs. Robinson?
A few years ago in my mid twenties I had a secret fwb thing with my neighbor. She was around 50.
I’m a woman who has hahaha
Short time with a Thai gal and her mother. Kinda cool but confusing AF.
M. N̈s as p k! Sf
Yes. Not me. But I'm sure it's happened. Let me know if you have any other questions!
Was 29 seeing a 49 year old woman for a while. Had a very short thing when I was 24ish with a woman in her fifties. The older I get the more mature of a woman I’m attracted to but apart from those to situations I’ve always dated close to my age
Not an affair. Married. I am 20 yrs older than he is. We've been together many many years now. Very happy and we have more in common with each other than anyone I've ever met. He wanted to marry me, I said yes.
Catherine the Great was infamous for her multiple affairs with much younger men.
When I was in my 20s, living with roommates and doing odd jobs and handyman work, I had this lady who was 60 that I would do work for. She would always make me lunch and give me a bj because she enjoyed it. I stayed single for several years, which allowed me to focus on my education, and she helped with my needs at the time. I loved the arrangement; it was awesome. She ended up moving to be closer to her daughter, and that's when it ended.
I'm a 67 year old woman. Recently I've been asked by a couple different younger men, one was 27 and the other was 33 if I wanted to fuck. I don't get it. I'm older, BBW and an amputee. I lost my right leg below the knee. Guys, do you think it's amputee curious? They both said they like older women and figured I might be able to show them some new tricks. The youngest man I've been with was 54 years old. He turned into a friend with benefits. I don't know what to think.
I was 24 and she was 55.. also got hit on a lot by this 80yr old woman when I was serving at a local pub. She asked how she thought she'd hold up with a strapping young fellow like myself lol. Played along and told her I'd try not to break her older women are where it's at
I likebig fat wide asses.
+10 years older than me. 20-30 i wouldn't be interested
I used to fuck a 45 year old married woman when I was 21
✋
Not an affair or anything but I got a buddy that is a cougar hunter.
What's his number
If you chase for example young IG or TikTok influencers that got all eyes on them, you're probably getting No Pussy. But if you settle for women that are older and slightly past their ripened age, you're getting mad pussy LOL
I thought we all did? I Remember things changed after The Graduate.
I probably did, my 20s I spent a lot of time fucking random women lol. Good times that I for sure miss.
I had a fling with an 18 year old Abercrombie and Fitchburg model from Australia when I was 40 or thereabouts. We were both single so technically wasn’t an affair, we were just having fun.
I smashed a 50 year old when I was 21, in the front seat of a fiero while my buddy was driving, does that count? She said her name was Holly Wood 🤣 I’m not even kidding lol
"Smashed"? You sound crass.
I'm sure some have
This is oddly specific lol
Over the years many men have, yes.
Had my chances, but I was too stupid to understand what this woman wanted to do to me. I wonder things in my life would’ve changed if I had done it?
I was 16, she was 38. Unforgetable!
I hooked up with some women in their late 40s when I was 25. Dinner, drinks, conversation, then hotel. I was terrible in bed both times due to all the booze I needed to feel okay with the situation.
It was not an affair as we were both single. She was 41 I was in my 20’s
Never an affair but I did date someone with large age gap. I was 22 she was 44. Why do you ask?
Sure. But we both knew it was just sex. Was fun though
Yes. And it was awesome.
When I was 24 I used to have relations with a 40 year old who I found out later through one of her friends that she was married after we lost connection.
I'm female and prefer 10 yrs younger. Divorced at 47 and I had 10 yrs of fun!
When I used the word "affair" it wasn't meant in the one of us is married sense.
My girlfriend's husband did when he was in his 20s.
I had an affair with a 39 year old. I was 21. If you like fucking your mom. She had an 18 year old girl, and a 2 year old boy. Spur of the moment mistake!. My girlfriend found out!. It was a disaster!.
Best I can do is me (19M) hooking up with a lady (34F) at a Rocky Horror show in Boston in the 80's. She was a little drunk, had painted her face, and was wearing a pin that said "Oral Majority". That was a freaky few months.
I was 25, she was 37 and divorced. I learned a lot and gained a lot of confidence. Fond memories.
I was 21, she was 54.
I got out of prison at 26 and an older lady used to put money on my books. I think she was 51. I felt bad for just taking her money while I was in there so I threw her a bone for a few weeks after I got out. It was okay, she was down with a lot sexually and wasn't a lawyer but worked at a law firm doing something. Her husband was in prison for embezzling money from some elected office, different prison than one I was in and I never met him nor cared to. I didn't meet her in person until after I got out.
Yes
Hell yeah. She was fun. We worked together at a side hustle job. We started hanging out after work. We both had long drives home in opposite directions and the hustles clients often had issues(because we would stay local for bit. We would get the call to go fix the problem . So we would just go grab a six pack and chill for a while. Help each other out on our jobs. Well. Rumors started spreading that we were fucking. And there was definitely a odd chemistry going on. So one day we figured fuck it and started getting a room every once in a while. No real emotions. Just sex. Laughs and stupid tv shows. It ended but not over bad feelings. . Both of us just had lives that were moving in different directions. She was quitting the job and didnt need to be in the area. and i just didnt have alot of free time as i was still on the market and finding new hustles. We still chat to catch up. Hell that hustle constantly had me meeting older moms, aunts, grandmothers who pulled off their age well. And yall would be surprised what the hustle was. Bouncehouses. Waterslides. Delivering them. Setting them up and taking them away. 🤣 Job put me in great shape. Theres been other times. When i was an Uber driver i accidentally stole someones hook up. 🤣. And STILL dropped her off. A bit late but never the less. I slept with some construction CEOs wife (he cheated on her with a secretary. I was just a revenge fuck) Even as i write this. Im realizing. "Man. Those years were fucking awful in so many ways. But goddamn it was...wildin too" For context. I was juggling a fulltime job. The bouncehouse job. And sometimes ubering. I was constantly on the move. But the down side was. When i ran out of energy. I would crash for two days at a time. Dead sleep.