M 62 here, my biggest surprise came to me a few years ago but before I share that let me give some context.

I grew up in the PNW of the U.S. in a family that had a stay at home mom and a dad that worked his butt off. He had some personal demons that made him insecure to some degree and somewhat introverted. As a he would buy a home and fix it up and sell it, this was before the term "flipping" was even thought of, but basically that is what he would do. When we moved we stayed within the same general location but was always far enough that it wasn't easy, or sometimes possible to go back to the old neighborhood to see what friends we had made in the 1 - 3 years we were at our previous place.

As a result of the moves I was exposed to city, suburb, and rural life, which has helped me tremendously as most jobs I have had over the years required the ability to communicate with a wide group of people.

Due to our moving I and my sister who is 2 years older had to endure the fun of reliving being the "new kid" in school. This basically met that all the idiots had to try you out to see how far they could push you and as a result I ended up in a lot of fights. For a time I would just retreat to the Library of the school and read fantasy fiction, Sci-Fi, or Greek Mythology. By the time I was in 9th grade my reading level was that of a first year University student.

I never really had girlfriends except once in grade 11 which ended up breaking my heart, I have always fell deep when I fell for a woman. So I never really learned the art of dating or how to read signs that someone was interested. Also due to the constant teasing and meanness that I experienced from being the new kid I figured I was not very likeable or attractive to the opposite sex.

I had this self perception challenged as I got older. When I was 16 -17 I worked for a neighbor who owned some horses and her husband would go away on work trips. She was in her late 40's and she would often do some subtle provocative things like live a pair of underwear on the deck of her car inside under the rear window, or answer her door with her pants undone. Once when I went in to get paid she was drinking some wine and said "I'd give you some but I don't want your parents to know." She was a moderately attractive woman and if I had been convinced, at the time, that she was trying to see if I was a potential for her I would have returned the flirts but I did not have the knowledge, skill or courage to do so. It wasn't till much later that I realized she was trying to open the door to seducing me.

There were a few other times that older women played the same game but it never came to anything.

I went to school eventually married someone my age and didn't think much of it all.

At some point I started noticing in my early to mid 30's that sometimes younger women would flirt with me, I always just thought they were playing games and just seeing if I would bite but if I did they would just turn me away as a game. So I never acted upon some of those possible invitations.

Years later after a divorce and on my own I connected in a social app with a 32 year old, I was at this time 58. We texted off and on for about a year, I am the kind of person that can discuss anything and nothing shocks me be it lack of knowing something common or having done or wanting to do something that is considered "taboo" by our culture. She ended up inviting me over to her apartment and initiating an intimate FWB type relationship.

She was Asian and very petite with about size B - c breasts and a nice small ass. For two years it was the most amazing sex I had ever had in my life. Unfortunately her job had to have her move to the middle east and I did not wish to move to the country she was assigned.

Since that encounter I have had a couple more short term Age Gap relationships but have yet to find the woman who would weather the dynamic of a large older younger age gap relationship. I'm pretty traditional and not into these relationships where the woman wants to play princess and basically do nothing and spend her partners money. I know from experience and observation that the best relationships are ones where each party contributes as much as they can in responsibilities be they in or outside of the home, it is after all a partnership.

I'd love to hear of any other men who have had the "Big Surprise" of a younger woman initiating as relationship and you never thought in a million years it could happen and how did it go?