I also started by trying my mother's and older sister's shoes. I can't recall at what age or any particular pair of shoes I tried, but I remember when left home alone, I used to sneak in to closets to find shoes to try on. The same sneaking took a place when I was sometimes allowed to go to my dad's workplace with him, and while he was concentrating to his work, I was wondering around the office and locker rooms to find women shoes to try out. One particular pair I still remember, dark brown greenish knee high, with zipper and block heeled boots. What a sensation it was to try them! Size was perfect, they fit perfectly around ankle and calf, I was in seventh heaven when I put the boots on and pulled up the zipper first time. I think that was a starting point for me liking the heels on me, I can't recall any high heels from home, but those boots had maybe 2 or 3 inch heels and that feeling on my feet was incredible.
At the same time when I had the boots on and was walking around the locker room to get the feeling, my father had finished his work and was looking around for me. I didn't hear him coming, I was still in heaven and didn't pay any attention, but when I saw my father at the door, taking quick look on me, turning around in a way that can tell that he really didn't like what he saw, just mumbling that we are going home now, I think I also generated shame and guilty feelings for wearing the boots based on my father reaction. We never spoke about that later, I think my father just wanted to ignore what he saw. But it might have hit him later when I was openly cross dressing and my parents knew it as well, my mother took it very badly in a first place but my father was cool about it. I didn't realize it earlier, but most probably my father had an idea already. I think I was never caught by my mother and that one time only by my father, and I guess my parent never spoke what my father saw in that locker room... so he was somewhat prepared but my mother was not.
But the starting point was most probably the boots I tried on at the locker room. The sensation of perfect fit on size and everything, the feeling of the lift the heels generated... yeah, I call this event to be the moment when I started to like wearing heels.