35 when I was 24.
It lasted about a month. I found out she was a very sheltered 35, who was desperate to get pregnant and married (the order was unimportant). Fortunately, I managed to extricated myself without fertilizing anything.
The sex was good, though.
Me: 24
She: 37
It was fun, but it got weird pretty fast. She started looking for commitment early on, and then I started doing some math and thinking about ten years down the road. We parted as friends.
As a young lad, I was seriously involved with a woman 18 years my senior for a couple of years. She had some serious mental problems, though, and I let it continue longer than I really should have. I almost had to get a restraining order on her at the end to keep her away.
A friend married a woman 20 years his senior whom he was seeing. They were living together, and the only reason they got married was so she could get the judge to give her child-visitation rights for her son from a previous marriage. They weren’t serious about the marriage, though, and ended up splitting up amicably and divorcing, as they figured they would.
What about older men? I lost my virginity to a man who was 56, and I was 18. Met on the internet, of course. 
And somewhere in the security office is the “private stash” of gonzo cruise porn collected by security cameras.
My stories, lost my virginity at 19 to my 27 year old EMT partner at work, while we were on duty, in the crew quarters when it was just us. 8 years.
My wife is 8 years older than me.
Another one I was 24 to her 39 so 15 years.
Got propositioned by a 58 year old woman about a year ago, but passed…22 year difference.
Cured my sexlexia with a 30 year old woman as a 21 year old. The relationship was very screwed up, but we made it work. Oh memories.
What constitutes “significant”?
Here are my biggest age-gaps. Both were rels, not indiv nights of sheet-sharing &etc.
Sylv: she 36 when I was 21, diff of 15 yrs
Marion: she 52 when I was 35, diff of 17 yrs
Had a brief fling with a 50-year-old woman when I was 29. No regrets.
I was a Mormon missionary (age 21) when a maried female member, age late 30s, developed a crush on me. We had a brief affair after I quit Mormonism and returned to Japan to play around one summer.
It was back when I was young and foolish, (as opposed to being older now, but still foolish) and terribly risky. Her husband was a karate champian with a terrible temper :eek: and she was lonely because of his strings of affairs. God knows if she wouldn’t have told him about me just to piss him off :eek: :eek:
My wife and I are about the same age – I’m two years older – but I know lots of Westerners in their 50s with Thai wives and/or girlfriends in their 20s or even late teens.
Not me, but my husband married a woman 18 years his senior…
[sub]Me! silly![/sub]
I just realized I’m too old to be a boytoy. Another life experience that passed me by.
Me 17, her 28. And then again, me 20, her 36. No regrets, though I didn’t treat the second one very well (the first was a one nighter.)
Yep, my first time was with a 29 year old when I was still a few weeks away from being 18. A year or so later was a smaller age difference 18 or 19 (can’t remember when exactly) and she was 26. There was this hot older lady who I had a thing for the first couple of years I was in Japan. We’d bump into each other every once in a while. The farthest anything got was some (very) heavy petting and serious making out. She was quite literally old enough to be my mom, 47–48 when I was 25–26; my mother had me when she was 21.
So when’s the official cutoff point for that, anyway?
me - just turned 18, her - 47
Best relationship I’ve EVER had. Taught me everything I needed to know. The wife is currently 6 years older. Only dated 1 woman younger than myself. Having a birthday close to the cutoff for for school kind of made my selection older than me growing up, and I tend to hang out with an older crowd.
You never know. More and more people are living to 100. You might still get picked up by some hot (great-great) granny.
I was 21 and she was about, but not much more than, 30. It was my one Penthouse Forum experience. I still think of it from time to time.
My first time was with a 31 year old. I was 20. Then a fling with a 42 year old when I was 21. Then a 38 year old when I was 22.
I slowly started the age decent after that. Next was a girl 4 years older then 2 years older then 1 year younger. Now I’m in a serious relationship (going on our 4th year together) with a woman 8 years younger. I’m 35.
My SO is 18 years older than I am. So significant problems, those who matter don’t mind, those who mind don’t matter. We’re great together. She’ll be the first to admit that I’m often the adult in the relationship.