That is, wife (43) and daughter (12). Told them I was re-evaluating myself and who I wanted to be, and that I wanted to try being "cuter" (didn't quite have the courage to go further), and that perhaps men's clothing didn't suit me.
The wife was mostly "yeah, right" -- seemed happy that I was trying to improve myself but seems to think it's just a phase (maybe it is? idk).
But my daughter was right on board! Came up with a load of outfit and makeup suggestions, and proposed going to an anime convention together, dressed up. I asked her if she'd think it was weird for me to go about dressed as a gothic lolita, and the response was "no, I think it'd be cute."
So next step is maybe cute anime girl cosplay at home, with an ally!
I'm literally shaking with ... excitement? fear? relief? I have no idea. Ohgodohgodohgod what am I doing...
Simply because I needed to meet some women for my perception to switch from "unfathomable sex objects" to "people I like to be around". Which it did, very quickly, and even if I didn't know why it was immediately clear to me that I liked, even preferred, hanging out with women as friends. One of the first times I was able to express, even jokingly, a desire to be more feminine was to a group of girlfriends. My egg exploded soon after.
It's possible social pressures would have kept boys and girls apart like you describe, but otoh I've always been a bit of a deliberate outcast, and I'd probably have quite enjoyed defying those expectations.