Biggest Age Difference You've Had With Sexual Partner

steveh9

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I was 19, she was 45 and smoking hot. We fucked over and over all night until I just couldn’t do it again. My dick was literally sore!
And she loved every minute of your young cock fucking her
 

BIGDP

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I had a partner for 16 years. We had a 23 year age difference. When we met, I was 36 and he was 59. He had three sons, the oldest one was just about 1.5 years younger than I. My partner passed away at age 76. We had a lot of fun and accomplished a lot together.

Now I’m 59 and waiting to meet a guy who is 26 and has the hots for me. Fucking COVID. :(
 

indyfrat79

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I'd just turned 18 and discovered the cruising park in my home town. Had a mid 60s guy as my regular cocksucker for the entire summer before I went to college. Good looking guy. Retired teacher. And loved teen cum.
 

NJBearGuy

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When I was a freshman in college, I had a big crush on my advisor. He was probably between 46 - 50 years old and I was 18. He was married and had kids. I never really thought much about it, other than my crush. He was also the head of the theology department and since it was a Catholic university, we were all required to take 6 credits of religion. He was my professor for World Religions.

So cut to about 8 years later. I am out of grad school, working in NYC in the financial district, and living on my own. He messages me on gay.com and it turns out he is divorced and out gay. We spend time chatting, etc. One things leads to another and he becomes my regular fuckbuddy over the years, whenever we were not dating anyone. He was / is a total bottom and used to love for me to pound the hell out of him and shoot loads down his throat. I am now 50 and he is close to 80 and we are friends on FB and chat all the time, but nothing sexual or anything. Just friends and stuff. He is a good guy.
 

libralover4u2

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I was 64 and she was a gorgeous 27-year old dancer in a strip club. When we met there was immediate chemistry and we each realized it. We began by going out for breakfast after the club closed, and I would take her home afterwards. Soon we were having short make out sessions as each date ended. Four weeks later she agreed to go on a weekend trip to New York City. The first night we were there she saw a marque, La Trapeze, as we were driving across town to go to a Broadway theater. She asked, "What is that?" I told her it was a swing club. She asked what is a swing club?" After I told her she said, "That sounds like fun. Let's go after the show."

That night we agreed before we went in that we would just soft swing, no penetration, The club was very nice; the owner showed us around; we took off our clothes and put them into a locker; wrapped a towel around each of us; and went into the group room. It had mattresses on the floor and mirrors on the ceiling. We laid down on my towel, covered ourselves with her towel, and watched and listened to all the sex going on around us. Later we played softly with two other couples. That night back at the hotel both of us were excited from all the sex at the club, like being in the middle of a porn movie.

Two weeks later we came back, and this time we swapped with another couple. My gal had never had children and was so tight the guy came in about 10 strokes. That started our 11-year swinging relationship. Soon we were hosting small swing party about every three weeks. While she could not take large cocks at first, after several years of swinging she began to be able to take large cocks, and soon became a size queen. But, no matter how long she fucked a large cock, within a few minutes her pussy would return to its former tightness. After every session we always had our loving, sex time together.

Soon after we started swinging she stopped dancing, got a regular job in a business, and finished her MBA. But, we were able to take vacations and business trips so we could visit various swing clubs and arrange swing sessions during our domestic and overseas trips.

i enjoyed watching and listening to her have sex with other guys, and she did the same with me and other gals. Because of her, I had sex with a lot of women who were there with their guys that had been lusting over my gal.

After 10 years she began to get restless, and longed to have children. But, I already had four children and did not want any more, so we agree that she should date guy who had potential to get married and have children with her. During that last year, she found a guy that suited her; they fell in love; and decided to marry. Shortly before their engagement, we had our last swing party with several couples we had partied with and several studs that she particularly enjoyed. It was a great way to end the wonderful relationship. She must have cum 10 times that night and I was drained too. The next morning we had one last round and said goodbye.
 

elchippe

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When i was 20 year old i have sex with an ~45 year old gym rat of a woman in really great shape, the best sex ever, very different from the girls at younger age that just lay down and expect you to do all the work. On the other side the youngest one was a 19 year old very cute trans girl at 34 years old.