...in my teens and early twenties, I had long nightshirts that I'd pretend were dresses.

I hesitate to mention this next part, because it reads so much like cliché TG fiction, but it did indeed happen:

When I was about nine or so, I remember having a red button-down flannel shirt that must have been two sizes too big on me. I wore that thing constantly. Back then, I had a little difficulty with relieving myself the male way (opening my fly and...you know) because I'd always splatter the front of my pants. So I'd pull my pants and underwear down, stand there and go (I didn't sit because that was what girls did, and at the time I didn't want to be caught doing anything girly).

My stepdad got fed up with this and demanded that I do it the "right" way. When I tried to explain why I didn't, he said to me, "OK. For the next week you won't wear pants at all! That'll make it real easy for you!"

The next day I walked around my parents' apartment in nothing but my long red flannel shirt and my leg braces. The shirt just barely reached my thigh, as I recall, and I remember thinking, "is this what a dress feels like?" After that, I felt a lot better (though without fully understanding why) and a great deal less self-conscious. I'd literally forget I had no pants on. Mom more than once had to yell at me to get away from the glass door leading to our balcony. =) (The balcony faced the street, so people could see in).

My mother, bless her heart, put a stop to the punishment after three days. But truth be told, I could have done the week standing on my head--well, maybe not that, since my "dress" would have fallen down over my head. =)