Largest age difference?
 

Mine was 37 to 20. Disaster, as the girl got _really_ upset when I did not want to marry her. Met her online, then flew over for a week to fuck her. Very slim, rather beautiful, 100% crazy.

I'm going to assume it was around 40-plus years.

When I was 21 I fucked a woman in her mid-60s. She was actually very good-looking. She looked a lot like Elizabeth Taylor in her younger days.
But earlier this summer I fucked a 21 year old and I am 60 years old now.

Other Chanel
 

Housewife 53 years Toyboy 21 years. x hamster. My Sister-in-Law. But I well remember her complaining about the cost of the Hair-Do ! And that was when she was 32yo ! Of course, since t'was a "Casual fuck", filmed by her (tiny rigged) Husband to both sexually satisfy her, AND bring-in some ready-cash via the sale of the Video, I can neither vouch for Toyboy's age, or where it was filmed.

Before we met, wife was 18 having sex with a mid 80 guy. She had a threesome with him and his friend whom she guessed was around his age. All she would say was they made her feel good and treated her like a princess.

I love seeing the older guys still get it from the young ladies.

Age ain't nothin' but a number.

When I was 40 I fucked a woman who was in her mid-70s. She was still quite attractive: full , thick head of silver-white hair, well kept body, pussy just as snug and wet as an 18-year old. She was awesome.

I think the biggest age gap for me was five years and a few months. I will not say the ages we were when this took place other than to say she was my first and was my best friend's older sister. She is still smoking hot today at 46. I guess it is possible there has been a bigger age gap at one point or another when age was not disclosed later in life but I doubt it was much more than five years in either direction.

I have only been with women who were within 18 months of myself, which is zero age gap, really, but the first time I was casually nude with my mother in law (long, non-sexual story), I was barely 30 and she was mid 60s. Her body looked like a 25yo. We stared at each other like we had never seen a naked person before. It was quite nice.

For a brief time in my early 30s I had a gf 18 years older. And for several years in my late forties I had a gf 24 years younger.

your right lol
as for old guys and my wife who loves to be exposed spanked and put in her place by older authority figures
this one was a bit different for her usual type of older guy ,yeah he was old about 76 at the time this happened but he wasn't strict bossy or domineering like the other old fellas she had been exposed spanked fingered and fucked by had been ,dunno maybe it was a challenge for her or she was so c*nt drunk and just threw herself at him ,

i know she was always wet and ready to fuck after she had been teasing and exposing herself to him and those times were about the only time she didn't have a red sore smacked bum when we fucked ,so he must have got her so worked up that she lost control lol

okay a couple of years into our stay on the holiday park we met this nice old fella about 75 he was,he was on his own every time we saw him and my wife asked him if he wanted to join her and her friends at their table ,there was usually 10 to 15 all owners and all gathered around a couple of the tall type of tables with stools ,turns out he lived about 5 miles from us at home no attachments ,amongst other things in his past

he looked good with a gun and he used to breed and race greyhounds with his much younger girlfriend so he was a bit on the shady side
as we would say "he was one of our own" lol

,anyway me and him got on great did loads of stuff together mucking about ducking and diving with old cars ,car booting , nicking the oil from round the back of the local chippys to run his car on lol all sorts of dodgy stuff we were a great team
so me being me and noticing he and my wife had taken a shine to each other, i tried to get him in on putting her in her place and smacking her bum for me , no luck at all he just didn't respond to my suggestions in that way ,so i left it not wanting to ruin our
friendship
we got pretty close with him ,my wife would hug and kiss him goodnight and i thought of him as a dad /big brother ,we had him over for Sunday dinner and went out for a drink and regularly met up in the closed season back at home ,
he used to stay over as he'd had a drink and sleep on the sofa downstairs

my wife used to go upstairs to get changed for bed ,which was usually one of my old vests that skimmed her arse and shows most of her tits through the arm holes ,she would come into the living room where me and the old fella were sitting on the sofa and she would go to the mirror opposite stand on her tip toes and bend forward and pretend to be engrossed in taking off her makeup ,other than a bit of lipstick and mascara she didn't wear any lol
this gave him a unobstructed view of her bare bum and fanny she would open her legs and wiggle as if she was concentrating ,but she says she was really trying to give him the best show and view of where she wanted his attention his fingers and his knob

after saying goodnight id leave them to it and go up to bed and wait for her to come up all turned on from exposing herself and teasing him and the kiss and cuddle they had had and her wiggling her bare bum at him before she came up to bed
,she always asked me if she was rude or naughty for doing this in front of him and
what would he think of her and about her for exposing herself to him ,we would fuck and id tell her she was doing a nice thing for him and he loved it

anyway this night it went down the same but she was ages down stairs and id fell asleep ,she woke me up and looked mortified i asked her what was wrong and she told me all the usual showing and teasing had gone on but when it came to kiss and cuddle time he had sat down and pulled her to sit on his knee as he kissed her he had one hand stroking her bare bum and one feeling her tits ,she said this got her super aroused and she squirmed and wriggled her bum so his fingers met her wet fanny and he slid a finger between her lips but didn't stick it up her fanny like she wanted him to , she felt for his knob which she said was hard and ready for action so she groped and squeezed it while she wriggled to try to get his finger up her fanny where she wanted it
she said she thought it was then he lost his nerve and she said his dick was softening so in frustration she said she told him she was sorry and it was all her fault and she deserved a smacked bum for being so sl*ty and naughty towards him and lay across his lap and opened her legs and begged him to slap her bum for her for being so naughty
she said he seemed shocked and said he couldn't it might wake me and the kids but next time they were alone he would do it if she still wanted him to ,at that she got up and thanked him and made him promise he would slap her bum as he said he would when they next had a chance and she then straddled his leg and they started kissing and he held her close she said as soon as her fanny touched the rough material of his trousers and he pulled her towards him she knew she needed to cum
and while he kissed and fondled her she said she started at first to slide and rock her fanny on his leg and pushed back and raised her bum to give him easy access to her wet fanny she said he was feeling her bum and seemed surprised to feel her raise her bum so she started to feel his dick she said it felt so good to hold his dick while she rubbed her fanny on his leg and he stroked her bum hole and her fanny lips ,she said him touching her there made her lose control and she started to grind her clit on his leg and begged him to put his finger inside her ,which he did , then she asked him to put another finger in her ,and after a few finger fucks she cum while she was holding his dick and grinding her clit on his leg and he squeezed her tits and fingered her wet hole ,but as soon as she got off his leg she realized she had squirted and wet his trouser leg with her cum ,
she kissed him and said goodnight and ill see you in the morning wiggled her bare bum at him as she always did ,and left him ,she came in and told me about it her face a picture of embarrassed humiliation especially at the parts when she told me about throwing herself across his knee and begging for a spanking , admitting she had lifted her bum to encourage him to finger her and to beg him to stick his fingers in her when he didn't catch on and letting herself get so carried away that he saw her cum and felt it with his fingers as she wet his pants

when telling me about it , it struck her how out of control and submissive she had
been kissing our old mate and a quick tease and grope was fine and usual but to get so carried away as to feel his dick ,throw herself across his knee and beg him to spank her ,and then when he couldn't to beg him to finger fuck her while she rubbed her fanny on his leg until she cum and wet his pants with her cum and then just leave him down stairs with wet pants and a hard on to go tell her husband what she had just done and what a sl*tty prick teaser she had been and how would she be able to face him again after what she had done on his knee

i laughed and slid my knob into her wet fanny and slow fucked her and told her not to worry id make sure she made it up to him at some point lol

it was so cute to watch and listen to her confess to her dirty naughty sl*tty submissive behavior and hear her tell about how she threw herself at the oldest bloke we knew , our friend and how she had tried and so far failed to get him to give her the spanking she deserved for teasing his cock lol

what she teased him with and what she wanted spanking and what got fingered and what wet his pants lol

Rosebud
 

Thanks for sharing the story and the picture of your wife's arse. My hat is off to a woman who will show her rosebud. It's like she has shared her most intimate part. Give her a grateful smack on the bum from me please.

haha will do pal and thanks for the engagement and response ,

yeah its quite humiliating for my wife to have herself displayed like that and shameful to know everyones seen her most private part

she will love /hate you have all seen her exposed like this but will be wet thinking about it

here she is rosebud on show for all to see while waiting and taking cock
and pants down bum pushed out with my finger in her bumhole

message me if you want to see video of her getting her bottom smacked lol

Appreciated
 

Thank you, Red Roberts, for these great photos of your intimacy. I love them and they are a real turn-on. You are a fortunate guy.

Thirty year difference. She was 32 when we first slept together in 2019. Four years later and still enjoying the ride.

I'll guess you weren't two years old.

LOL, I started young but not that young. She is 30 years younger. I can't tell you why it works but it does, lucky me.

65 year old tart
 

I am close to 65 years old and I fuck younger men. They have to have big dicks to fuck me because I've done it all in my life, danced naked, and fucked a lot of men. I keep my husband's tiny dick locked up in a steel chastity cage. I let him watch me fuck the younger men and then I let him lick my pussy clean with his magic tongue. He's the best at eating pussy. All my girlfriends think so too. One of my present lovers is a black man named Jake. He has a huge cock and he's only 35 years old. Sometimes he brings a few friends and hubby really gets a show. Hubby's poor tiny dick tries to get hard in its little cage and can't. Poor baby. Right now Jake is my youngest lover but on a trip recently to the islands I showed off my tits and pussy to a young man and since I rarely wear panties he was able to bend me over the hood of a car and fuck me good from behind. It was night and at the back of a parking lot so I guess only my hubby saw us. The young man looked to be in his 20s but he was packing a nice sized dick. Here is a picture of me and one of me and Jake's 35 year old huge dick he uses on me. Enjoy!

30 -> 19
 

When I was 30 I dated a girl who was at Uni. She was 19. 11 years is quite a gap, but not a huge gap now that I am older. But back then, 30 to 19 was pretty significant.

When it was just the two of us, everything was fine and we had a great time.

But when her housemates were around (she was sharing with a few other girls) it was very clear that I was not part of their group. I was way too old.

But I enjoyed it, while it lasted, and her house mates were super hot.

I guess this isn't exactly the same, but I used to give my wife's mother massages, and one time I took a shower and she took one after me, and we were both naked at the same time for a bit during the passing in and out of the shower. I even stayed and talked to her while she changed over to a bath, followed by semi-dressed massages (for her). I was 30 at the time, and she was almost 70 (but she looked 50 and had the body of a late-20s woman...she still does. It's pretty unreal.)

Going the other way, I had my friend's 19yo daughter hitting on me all the time. Not sure if it was daddy issues or what, but she was very overt to the point that my friend would glare at her daughter all the time. I was cutting her hair for her once, and she even took off her t shirt and sat there topless. She said it was because she didn't want hair clippings caught up in her shirt. I think I disappointed her by not making any moves because she stopped the heavy flirting after that. My friend thanked me for not doing anything with her daughter. I was like, "I am in my 40s and she is 19, even if I weren't married, I wouldn't do anything. Even her teeny boobies didn't make me flinch." Secretly, it was really fun to see a 19yo topless and act like it was nothing, but in the end it really was nothing.

Hen I was 36 I had a 20 yr old GF, IT WAS GREAT!

When I was 20 I went to a friends family bbq. There were dozens of people but I only knew my friend. Over the course of the day this woman who I’d guess was about 50 was constantly flirting with me. She was nothing I’d have considered sexually if not for the many beers consumed and the fact that she was eye fucking me all day. She was a brunette with short hair. I wouldn’t say overweight but she wasn’t fit or skinny either. She had massive tits under her t shirt and as the beer flowed I found myself wanting to fuck her.

As the size of the party dwindled, she offered for me to come to her place. It was overtly for the purpose of sex. The sex was good. She may still be the best blowjob I’ve ever received. Her tits were surprisingly perky for their size and her age. I was quite drunk but still pretty green in the sex department. I remember coming fairly soon and her making jokes about it. She got me going again about twenty minutes later and that time we were at it for a good 20 minutes in nearly every position imaginable. Both times I finished in her mouth and she swallowed.

My wife also had sex with a man in his 50s when she was early 20s. A similar situation where she got a little too buzzed at a work party. She has said it was the worst sex of her life and a humiliating experience having to se him at work afterwards.

My wife is 58 and had sex with a 23-year-old that we met online. This happened at a hotel while I watched and sipped on scotch. There's not really anything more thrilling than watching some skinny, awkward-looking, college-aged guy who barely knows what he's doing get behind your wife and slide his dick in her.

I convinced my wife to do this because I've always had an "older woman" fantasy when I was younger. I never got to experience that fantasy. So I convinced her to try it so I could experience it vicariously through this younger guy and my wife.

Fifteen years ago my ex-wife who was 47 at the time fucked a 21 year old who was a work study in her office. She had the hots for him and just before he left the position we invited him to have a three way with us, which we had talked about doing for years but never did. So it was the first time for that for both of us and it wasn't awkward at all. She was a BBW and he was a skinny little guy but mature for his age and polite. He had never fucked a woman without a condom before, we took a risk and he came inside her twice. He also come in her mouth early the next morning before he left. I got to experience what sloppy seconds felt like and frankly it was wonderful, I never experienced anything so silky smooth like that. I agree there is nothing more exciting than watching a young guy like that fucking your wife, best porn I have watched. I wished I had taken video of it but I didn't. I did take a few pictures and wish I had taken more.

Maybe two years before I started dating my wife (but we were already friends), she started a thing with a coworker. He was almost 20 years older than her, early 50s I think, and was a supervisor at her job (not her direct supervisor though). He was divorced.

At some point she started banging him regularly. One time as we were fucking I asked her how often he used to do her, she said a lot, at least 3 and as many as 5 or 6 times a week. Apparently, the sex was excellent.

I've gotten different stories about how it ended. At first she said they wanted different things, she wanted a relationship but he didn't want anything too serious, and so they mutually parted ways. I pointed out that it sounded like he got exactly what he wanted in the end. Later she told me that while the sex was good, he only ever gave her one orgasm ... and promptly dumped her the next day. I figure he knew it was the last time and he wanted to make it count. I thought that was really hilarious ... I don't think she finds it nearly as funny however.

Turns out he was hooking up with some other chick on the side at the same time, and actually ended up marrying her. My wife says she should have known the guy was never truly serious about her, since he had a teenage daughter yet never once introduced them to each other.

I guess they kept it quiet at work, but at some point she had loaned him some money and after they broke up she had a hard time getting him to pay her back. She ended up having to tell the boss, who had to step in and make sure the dude paid her back on threat of his job. But that also meant everyone at work found out about the fling, which made for an almost daily walk of shame for her until she got a different gig a few months later.

I find it really hot that she got used as a fuck toy for months and months. I keep trying to get details about the actual sex but she's pretty embarrassed by the whole thing. She only really tells me bits of info when she's slightly tipsy and we're in the middle of sex. I hope to piece it all together over time.

the reveal
 

This is hardly the largest difference from those told here, but the circumstances add something. When we were splitting up, my ex told me about an occasion when she was in her late twenties, and got picked up by an 18 year old sailor in Paris, who then spent the night plowing her before he left to catch his ship the next morning. I arrived at the same hotel a few days later, and knew nothing about it . . . until she years later told me the details. The full account is written up as a message on my profile page.

When I met my wife she was 26 and I was 39. After a few months of hooking up we were at a party and ended up having a threesome with one of my friends who was 51 at that time. Not sure if 25 years was her biggest age gap but it's the one I know for sure.

Fucking Boss
 

Never before thought of these events in this context. I'm strolling along a Southern beach with my Sister-in-Law. She'd fully unzipped her costume, pubes and nipples flashing. Envious glances form the crowds. Suddenly, she started to confess her Pre-Marital Relations. A "Slow Learner", she was an Easter School Leaver. Soon, she was Employed as The Personal Assistant to the Area Manager of a National Company. Apparently, he'd married his then Bosses only, ugly, daughter. Simply for the money. Now a Grandfather aged over 50, with two, 30 something Children, he was desperate for Promotion, via his Improved Sales, to Company Headquarters. He'd a raging temper, so demanded instant action. He allowed her to Double her Wage, by taking a similar amount form Petty Cash, by providing Sexual Services for him, and selected, High-Value Clients. Tea Served Topless. Wank over Tits. BJ Under Desk during Negotiations. Swallow. Anal. Full Unprotected. She even took in a Record Player to drown-out the Noise ! There are some Tunes which, even today, she simply cannot Stand. So the many Age differences must have been well over 40 years ! Sadly, she's no longer with us.

When I was 19 I went on a trip with my best friend and his girlfriend’s family. We stayed at a vacation house near a lake and spent the days on the owners boat and the evenings grilling food and drinking. Each evening the parents and their friends would retire by 10 or so and the rest of the younger crowd would stay up until 1 or 2 and get a little rowdy. One of the nights of the trip one at a time everyone retired to bed until it was just me and my friends girlfriends sister. Again I was 19 and she was 30. She had two kids but was divorced and her ex had the kids for the trip. We got a little flirty and made our way to the dock for privacy. There was a covered area with lounge furniture and before I knew it she was sucking my cock with the cool lake air surrounding us. I stripped her naked and she was hesitant about her shirt because she had c section scars and loose skin on her stomach. I’d never really been with an older gal. Though I’m 42 now and obviously 30 doesn’t seem so old. But the fact that she had kids especially made it seem like she was much older. At first I fucked her missionary until she rearranged us for her to be on top saying she wanted to cum. She was drunk and couldn’t get off until I rubbed her on her clit and sucked her tits. Then she sucked me off and jerked my load onto the floor of the covered area. The next day as we all got into the boat someone remarked about all the bird shit on the dock. There were a few piles for sure but one pile was definitely from me. We had a few giggling moments about our time to ourselves but never hooked up again. She mentioned many times that she’d never done anything like that. Guess I was in the right place at the right time.

great stories from all loved it

I related part of this story earlier. I was mid 50's, dating a hot little 40 year old milf. One day I walked into her 20 year old daughter coming out of the shower, nice view, same body type. That night, heard her daughter fucking her then boyfriend in the next bedroom, quite the turn on. That happened frequently over then next year, both getting to see daughter naked and hearing her fuck. She and her mom were both very noisy, sometimes it because a bit of a contest.
Anyway, mom was out of town, I went by the house to feed the cat. Daughter came home from an overnight at her boyfriends. We got to talking, chemistry was in the air, she mentioned that her mom said I was a good fuck. She said, if you don't tell mom, I think you are sort of hot, I've never done an older guy, would you like to fuck me.....very direct. With that, she took her t shirt off, saying I need a bath, and to wash my bf's cum out of my pussy.
I thought for all of about 5 seconds, and dropped my shorts and took my t shirt off. We spent a lot of time in the shower, soaping each other up. She acted impressed with my tool, it stood up well for her. Wound up fucking her from behind in the shower. She wasn't used to how long an old guy can last, came a couple of times, then I filled her up. This called for more showering, than we would up with my dining on her freshly cleeaned pussy. I must have been better at that than her bf, more very vocal orgasms, just like mom who could cum multiple times too. By then, I was hard again, so she went for a ride on me. I didn't leave until the next morning, by which she was sore, but I think very satisfied. So, 55 to 20. I think I acquited my age group well.

I don't generally ask older women their age when meeting or engaging them because, unlike younger women, there is no need to, these women are obviously of legal age, so I can't pin down an exact gap. So, the largest age difference I can confirm, after thinking about it, is 44 years. I was 28 at the time and the woman in question was 72.

Her name was Gloria, and she was married to a guy named Bill, Bill was terminally ill and Bill very quietly permitted Gloria to start a relationship with his friend Hank after his death, Bill did this because he knew his time was short, and he saw Gloria growing closer to Hank and he wanted Gloria to be able to move on without any guilt. Whether or not Hank and Gloria hooked up before Bill gave permission or before Bill's death is unknown as all three are now deceased.

Eventually, Hank passed and Gloria and I grew closer, at 28 (at the time) I was younger than her daughter, which added to the taboo of the relationship but I was also old enough to understand why discretion was necessary, which is why I had no issue coming and going at night or keeping things quiet.

While Gloria was one of my first older woman experiences she was not my very first.

Sexually, Gloria loved getting her pussy eaten, which was surprising as many of the older women I have encountered were not used to having it done or having it done regularly, according to Gloria, Bill and Hank gave her oral sex with no argument. Anal sex was off-limits but her blowjob skills were amazing, she could easily put these young sl*ts to shame. She was rather deliberate in her style, she loved to use her tongue to tease you and was amazing at locking her lips around the head, it felt like she was french kissing your penis, also for an older woman she had gorgeous hands and always had a well-done and very sex manicure, either the classic red or french tips and knew how to use the tips of her nails to edge you close to exploding then bringing you back down. Sexually she was rather vanilla, doggy and missionary were most comfortable for her but don't take vanilla for boring, the sex was always pleasurable and her vagina felt great and we never used condoms.

Eventually, her health began to take a downturn and she was frequently in the hospital and which effectively ended our sexual relationship, our last sexual experience was me gently sucking her nipples and gently fingering her in the hospital room, which I was trying to do very carefully because she had a catheter in. I did manage to make her giggle by pulling out my penis and wagging it back and forth. I gave her soft kiss and left and that was one of the last times I saw her.

Her friend, who probably knew about us but never confirmed either way, gave me updates on her until she was gone.

So Gloria is the largest age difference that I can confirm, although I suspect there might be a larger gap but maybe not, I have had sex with a few women who were over 70, but I was in my mid-30s at the time and the age difference may have been around 35 to 40 years in those cases.

Physically. Pink (ac1601's wife) Jeanne (dirtyharry11's wife) KaCee (kacshadow's wife) and Reba (RebaandMac's wife) remind me of her and she kept her strawberry hair even into her older age. KaCee's breasts and Gloria's breasts are nearly identical.

Mrs. Itionthat's blowjob style is also quite similar.

Breast of Memories
 

So happy KaCee can generate fond memories of your youth, Ghetto.

So gorgeous, big smile, bigger boobs and being bold in a hallway!

Sounds like us. My wife was 48 when I found her a 23 yo on Craigslist. Amazing to watch. I did have experiences with mature women when I was 18-19, now that I am older, I wanted my wife to be the mature woman.

I have a 20-year age difference with my wife. I had known her for a while but never thought about anything sexual or romantic happening. Our stars aligned during the early part of covid, and she made her move on me, more or less, haha.

I was very aware of our age difference early on, but I rarely think about it anymore. We get the occasional "your dad" or "your daughter" comment, as well as some looks, but I guess I'm desensitized to it now.

It's wonderful to hear that Pink and the other beautiful ladies mentioned can all take you back to a time and place in your younger days that I'm sure we would all like to visit if we could. Memories and the minds eye are truly a wonderful thing...... especially as we age.

Age gap
 

I’m 61 my wife 38 same age as my daughter. She is beautiful body of a twenty year old. Every time she undresses I can’t believe she’s my wife also a sweet girl

I am 67 and she is 36. Very shy and led a sheltered life. I took her virginity 4 years ago. She now enjoys watching porn, she is fascinated and very turned on by FF and MFM scenes. She just started to let me play with a camera. My goal is to eventually be able to watch her with another woman and fuck another guy. Who is in? 😁