Was there one event that started your dressing - like a trigger?
There was with me.
As a boy of 14 I was chosen to perform in the school play at my all boys school. To my embarrassment, I was asked to play the female lead - a young woman in an eighteenth century French farce by Moliere. Everything was going fine and eventually we came to the costume fitting which involved petticoats, stockings, wig etc. Still, everything was normal.
As a finishing touch, the wardrobe mistress fastened a choker around my neck and said: "why, you have such a little neck, just like a girl's."
This remark rang around in my head and I started to look at myself for other feminine features and I realised that my body was very non-masculine and I obviously had a very strong feminine side. I began to borrow my mother's clothes and this started me on a long and pleasurable journey on which I am still travelling.
I still love wearing a choker!