Unlike most of the members here, I came late to crossdressing. As is well documented elsewhere on the site and many times in the chat room, I only started crossdressing in my early fifties. So what happened? Why did this happen "out of the blue"? The whole experience has caused me to ponder these and similar questions on numerous occasions and, whilst I have no definitive answers, I realize that perhaps this late onset was not as sudden or unexpected as it seemed. When I think back on my life so far, there are several subtle hints that individually mean nothing, but collectively perhaps suggest that there was more to me than met the eye.
I vaguely recall that when I was very young, (pre-school age) when getting ready to go somewhere, my grandmother would always lick her middle and index fingers before scrunching my hair into a "wave". Almost without fail she would comment to my mother "With hair like this, he should have been a girl." I never thought anything of it except that I had nice hair.
During my primary school years, I did all the usual boy things: played footy and cricket (neither all that well), marbles, cowboys & indians, Robin Hood, William Tell etc. I had a collection of Matchbox cars, the usual boy comics and a good collection of Biggles books. At the same time, I had no difficulty playing tea parties with my sisters and cousins (most of whom were girls). I never played dress ups and I'm sure I didn't play with dolls by myself but occasionally joined them when that's what they were doing. I also read The Magic Faraway Tree and many Secret Seven and Famous Five books.
Apart from being one of only a few boy cousins in a sea of girls, I was also the oldest of the kids in our neighborhood. I used to take the younger kids under my wing so to speak and when we were playing organized games, I always made sure that no one was left out. At one stage the adults of the area used to refer to me as The Pied Piper. Whilst it would be incorrect to say that this empathy & nurturing behavior is absent in the masculine, they are characteristics more usually associated with the feminine. I never thought anything of it, it just seemed natural and the right thing to do.
I was never jealous of my sisters although, from my perspective at least, they had it easier than me. At the time I attributed this to expectations for the eldest son that was so common in the '60s and the usual economic situation that exists in most families where life becomes less arduous as time goes on and the mortgage shrinks. However, I do now believe that overall, girls have it easier in the early years, at least from the point of view of more freedom to express themselves and often less expectation. Not that this is necessarily right, it's just the way it is in most cases.
Into adolescence, I had long hair (didn't everyone?), wore V-knee jeans, flairs or baggies & platform shoes with pastel colored or paisley body shirts. Hey, it was the 70s and I didn't stand out at all. However, thinking back on it, I did pay probably more attention to my appearance than many of my mates.
Fast forward 40 years and I sit now fully waxed, with painted toenails, earrings, anklet & toe rings, wondering whether these early tendencies were perhaps indicators of something more that was successfully suppressed by prevailing social norms.