My friend recently told me about how he lost his virginity to a woman in her mid-thirties when he was 16. I guess he met her on AOL (this was in the early nineties) and she was recently divorced and they ended up with this kind of inappropriate friendship and one thing led to another…there’s enough credible details to the story that I have no reason to not believe him.
With all of the sensationalistic news stories of teachers seducing their students and so on, it got me thinking - how common is “Mrs. Robinson” out there in the world?
That is the oldest woman I’ve ever been with, I have a friend who had a three-way with a 38 year old when he was 21, but he really regrets that incident.
When I was young, dumb and full of c*m I was seduced by a 33 year old woman. [Ok fine we both worked at the same restaurant and were both exceedingly horny] I was 21. So not that bad, actually, it was quite good. Mrs.Robinson was very nice to me. Over, and over, and over. Oddly, we live in the same town now and some 15 years later I still see her around from time to time. She always smiles at me, and I smile back. She has a husband and a little boy now.
I was 22, and she was 45. She looked really good for her age, too. I was between college and the army for a few months, and she was a struggling artist. We were kind of at loose ends. We’d known each other for a month or two, but we didn’t really have a long relationship. Call it a week. Still, it was quite a week. After I went into the army, she moved and we lost touch. Sigh. Such is life.
I lost my virginity to a 25-year-old when I was 19.
And Mrs. Fresh is five years older than I am.
I’ve had other younger partners, but with one notable exception, none of them could hold a candle to any of the three relationships I listed above.
What can I say? I’ve always had a thing for older women.
A friend of mine (yes, really, a friend!) married a woman 27 years his senior. He was 21 at the time and she was 48. “Jason”[sup]*[/sup] explained that all the young girls were too immature and not ready to settle down, but I suspect he was seeking an older woman to serve as a mother figure to him as his own mother was quite abusive and negligent. They were married for about ten years and then they got divorced. They fought a lot of the time, usually over money since she wouldn’t lift a finger and get a job to help out with expenses, relying instead on her hard-working hubby to bring home what meager income he could scratch together enough to pay the bills doing blue-collar labor-type work (this doesn’t have anything to do with the age difference, I realize). She was already a grandmother at that age, having a quite promiscuous teenage daughter who already had three children by the time she was 20. Jason didn’t like to be called “grandpa” by his wife’s grandchildren and he often resented their presence as well as his wife’s children and how they often took priority over him. Going places with them, a lot of people thought she was his mother and Jason and I were her sons, so it was rather awkward in many situations to be around them in public. I had a feeling the marriage was doomed from the start, so I was glad to finally see them put each other’s misery to an end.
42 when I was 21. I was the goalie on the intermural soccer team, and she used to hang out behind the goal and chat me up when the ball was on the other side of the pitch. Why was she at my games, you ask? Well, her son was on my team!
I had no idea it was going to happen, when I showed up to the bar on Halloween dressed as Dr. Gonzo from Fear and Loathing. It was pretty funny to wake up in the morning still sporting a fake mustache. I still rate it as one of my top five sexual encounters.
Yeah, had a one-nighter with a 30-year-old when I was 19, long before I met Razorette. I was used for revenge. I’m not proud of it, but hey, I was 19, recently deflowered, and she was the one throwing away a marriage.
I kind of have always dated twenty-something women.
When I was 18-19, I was hanging with 23 year olds. When I was 25, people my age. Now I get to my early 30s, and the 25-year olds are still there.
I imagine that this will have to change when I lock one in
She was 43 and separated, I was 23 and single. We were both on a cruise in the Caribbean. She was with her sister and another friend, I was with some friends. We had been flirting all week and the last night she wore a knockout outfit that did what she intended it to do- got me into a bathroom on the pool deck while most everyone else was at the on-board nightclub, and she rocked my world. I know, the bathroom isn’t the most romantic place, but both of our rooms were occupied at the time, and I wasn’t actually about to turn it down because of the location. She hardly seemed to mind.
Eventually we snuck our way into one of the lounges after the crew had finished cleaning it, and went for round #2 on one of the benches at about 4 a.m. She was a good sport.
Yeah I’ve dated 2 women that were 10 or 11 years older than me. The first one was around 36 when I was 25, she rocked my world and I rocked hers. After 4 or 5 years she wound up marrying her much older live-in boyfriend, who she had been living with the whole time we were dating (I never said it was smart, just so much fun.) Took me a long time to get over that. We’re still friends.
The second was good but not as intense, I was in my early 30’s and she her early 40’s. We’re still friends.
Of course I’ve dated a couple that were 10 or more years younger too, my current live-in GF is 10 years younger than my mid-30’s age.
She was 36 I was 23 we met through work. She was a spacey new-age stoner girl from California. I was attracted to that at first. It got annoying having to hear about energy and crystals and other new-age nonsense all the time. When I began to challenge some of her more outlandish ideas she decided that I “wasn’t as evolved” as she thought. By that time I couldn’t have cared less. She didn’t like that attitude and things just got worse from there. It ended poorly.
Later I met a woman who was 45 when I was 26. Recently divorced, she was renting out a spare bedroom in her house, I happen to be the one to answer her add and rent the room. One thing eventually led to another. She sold her house and we rented an apartment and lived together there for about 6 or 7 months.
The thing that ended it was that she always told me that she wouldn’t care if I brought other women home. You would think that would be great, especially since I wasn’t interested in anything long-term or committed either. At the same time I didn’t see any point in sticking around. We went our separate ways. We kept in touch for a little while, but I assume she met someone else because she stopped contacting me. She was a great person and a fantastic lover. Damn, was she hawt.
When I was 18, my GF’s mother seduced me and we went on for several months. She was a 36-38 year old divorcee. AFAIK my GF never knew. Then when I was about 33 I briefly dated a woman in her late 50’s, until she got too serious. She was a very wealthy widow. I was attracted to her and we had some great times, but I have to admit the money made a difference.
Not dating at all. But one of my girlfriends mothers took a shine to me when I was 17. She was probably mid-forties at that time so call it 25 or so years of difference. That was one hell of a weekend.
Funny thing, though. Lady Chance is less than two months different in age than I am. So it appears not have become a habit.
Oddly, we live in the same town now and some 15 years later I still see her around from time to time. She always smiles at me, and I smile back. She has a husband and a little boy now.