Largest age difference?

[Isurob]

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

[Wdyitc]

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.

[junification]

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.

[snuckalook]

Originally Posted by junification

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.

[mmbt]

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.

[regn]

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.

[Oralpleaser69]

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.

[twowide]

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.

[Htwjw]

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.

[bobmur]

great stories from all loved it