I suppose the reasons are as varied as, “How did you get your start in cross dressing”? Each journey is individualistic, yet similar at the same time.
The “Why” question has been asked for many years. Perhaps if it is ever answered one day, someone may become a wealthy person.
My earliest memory was getting into my mother’s make up at age three or four. I believe by age five I was dressing completely as a girl, with the assistance of two young ladies who lived across the street from me. This was not full-time but maybe weekly. I matured in the female arts under their guidance and dressed weekly or more often up to age 13, when my family moved away. I mention this, because I believe it was this childhood experience that gave me the strong desire to always present myself as a properly dressed and attractive female. Moreover, the actual strong desire to be a cross dresser, to emulate the two beautiful young women whom I grew up under.