So let me start.
1: Can you recall the very first time that you desired the thought to dress as a girl? Not the first time you did it, but when did you feel a hopeful desire or emotion to want/wish you could play dress up as a girl?
2: Can you recall the very first time that you dressed up as a girl or in various girls/women's clothing items?
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My answers.
1: I can vividly recall a strange feeling to want to dress as girl when I was 6 years old. A girl in my neighborhood who was friends with my sister was outside playing in the neighborhood with my sister and another neighborhood girl who was a friend of my sister's. It was likely a spring, maybe fall day as it was clear and dry. They were skipping rope. This girl was the same age as I was and also in my then grade 1 class. She was wearing a white turtle neck top under a Royal blue short jumper and she had plain white tights on and black patent Mary Jane shoes on. I recall barrets in her not too long, straight blonde hair. Her name was Diana. I was watching her from our front yard and I recall that I loved seeing her in such pretty clothes. I recall so wishing I could wear them all and be so girly as she was jumping rope. At age 6 one does not know why and it was way too young to be sexual. I just wished I could be wearing her clothes, shoes and hair to be so cute and girly. I've never forgotten this moment. I trust I recall it accurately enough though.
2: I can recall my first time dressing in my mother's clothes. My sister and I both got into my mother's stuff. Our parents were out shopping one evening and our older brother was to baby sit us as I recall I was 11 and my sister 10. He was outside likely doing stuff, probably working on his car as he was 7 years older than me. The two of us probably started looking at the Sears catalogue and at girls/ladies clothes and it led us to play dress up. My sister was not bothered by it as we got into first our mother's pantyhose drawer and each of us slipped on some pantyhose. We were obviously giggling as two goofy kids may. I recall getting a white blouse and a bright red pleated skirt of my mother's. My sister selected clothes she wanted to play dress up in. Just like that I had a white blouse on, red pleated skirt and beige pantyhose. At age 11 one begins to feel a bit of sexual feelings but I do not recall being too sexually aroused but liked the feeling and look of these clothes.
We soon were into her shoes. My mother had a pair of blue suede oh, 4+ inch tall wedge heeled sandals. I was able to fit into them well enough and the feeling of doing up the ankle straps for an 11 y.o. boy wearing women's clothes was intoxicating, boys do not normally have buckle up sandals to wear. My sister put on some heels too and we kinda pranced around the house and were having child-like fun. I was ecstatic with pure girly joy. I recall stepping outside on our sundeck. It was growing into the evening and I minced around a bit then came back inside.
A few minutes later we both heard our family car pull into the driveway and I especially panicked. I ran into my bedroom and under my covers, my sister likely went to our parents bedroom to take off the clothes she had on. Of course she was not panicking as I was. Under my covers I pulled off the shoes, clothes and pantyhose and silly-like tossed them out into the hallway, closed my door and put my boy clothes back on.
I stayed in my bedroom alone for a while, but eventually opened the door to see the clothes and shoes were picked up and put away. Not sure who did it? My sister? or my mother? but I said nothing and nothing was said about it.
It was so exciting and fun to play dress up, the panic and fear of being seen in said clothes by my parents was high until I got them all off. Again another moment in my life I will never forget. I trust I recall it well enough as these years have passed by.
After that a number of other times as I aged into teen years being home alone I would put on my mother's clothes and shoes as long as they' d fit. Yes, it probably was wrong to do so but a growing into a teenage boy who had a growing proclivity to crossdress and to express a feminine side did what I had felt I had to do. I had a few other close calls
but it was all as benign as I could at the time being a bit of a confused teenage boy.Well those are my answers to my questions asked, anyone else wish to recall their moments?
Made me think about the good old days. 
Sometimes it's so hard keeping up with the terms and definitions as they seem to be in a constant state of change! 
