I'm not sure I've sorted out how it finally started
My first time with a garter skirt, stockings, and platforms...and I was modeling it for my wife...I had just turned 55. We had already been married for over 30 years. It really came to a head from a couple of joking comments about how great my legs were, and that I could fit a couple pieces of her lingerie better than she could at that point (I had just lost 30 pounds). I joked back saying that I'd need heels and stockings. She joked back that I should do it.
I did. She couldn't get over my legs in stockings and my 6" platforms. She said we needed to buy me a dress.
That started the snowball down the hill!
Could it have been started before? Were there incidents that I can find earlier in life that show a tendency toward feminine things? Sure, looking back. However, I enjoyed (still do) being a man, so there were no negative issues about that. We had noticed for a long time that I'm very empathetic, and that I have some understanding of how women tend to organize and what their expectations are.
Was it just that I had been a male for so long that these other tendencies, the newness of them, became intriguing? Was I simply ready for that series of jokes that my wife and I traded? Of course, it was critical that she was as curious about my femme side as I became!
I really can't follow the path any better than that, but I'm glad we got here!
tina