I hope it's OK to post this. I would like to tell my story about crossdressing. I'm sure that most of our stories are so similar, at least that's what I've found looking at the web.
I seem to remember a couple of things before I ever put on a article of girl's clothing. One was a dream, where I was wearing a green raincoat, the other was sitting high in the choir area in church looking down, wishing I could dress like some of the girls of my age.
I'm not sure just how old I was, but I think around 6, when friends stayed over at our house. They had a daughter, and I just couldn't resist trying on her embroidered cardigan. From there I 'borrowed' my sisters clothes. I started skipping school occasionally, both my parents worked, and spent the day dressed.
When I was probably 15 I skipped school, dressed up, did my face and took my sisters Lambretta scooter out for a ride. I rode for a couple of hours, stopping at secluded places to just rest and enjoy. When I got home I was about to go inside the house when one of my best friends from school rode into the driveway. I couldn't do anything but hope he didn't recognise me. He actually thought I was my older sister, and I explained, very briefly, that I was not well and staying with a relation. I saw him the next day at school, and he told me he'd popped around and saw my sister.
Obviously I could pass when I was 15.
Hope this is OK, I'd like to tell more later.