I believe most all of us that fall somewhere under the transgender umbrella knew we were different. Early on, I was totally unaware that being transgender had a name and thinking I was all alone with these thoughts. Most importantly, I didn't having a clue as to how to cope.
I just compartmentalized my transgender nature. Over the years I have been told story after story about harsh outcomes of being caught and being subjected to treatment "in all the wrong ways". Kids being sent to what is called today, "aversion therapy"; or distraught parents trying to shame/beat this out of the confused child. I was so fortunate to come out of the formative early years unscathed.
I am unaware of anyone in my era, whose parents allowed the son to explore his femininity. E.g. took him shopping, went to the prom, or spent the summer as a girl. Lovely as they are, these beautiful fantasy stories are just what they are - fantasy. If anything like that happened to you, please share. I am sure many would love to hear about your positive real-life cross gender experience as a child/teen.
Back in the 1950's and 1960's, when I was growing up, sex was barely discussed in polite company. So the action of cross dressing would have been one of the ultimate taboos - except on Halloween. Then it was OK because it was a costume. Also the south prided itself on its "woman-less" weddings, and beauty contests. Stana at Femulate has documented many of these.
In my little southern town everyone talked about the assistant chief of our volunteer fire department and how beautiful a woman he made one Halloween. No one even knew who "that woman" was at our annual community party. It was the repeat performance the next year that really set tongues wagging. "You know, he was so much better looking than his wife."
Something deep inside made me feel a kinship with his actions although not wanting to admit to myself how much I would love to participate.
Little by little, I started to understand that I was not alone. Then magic occurred - Puberty kicked in and I was off to the ball game with girls, thinking the cure had arrived. Little did I know?