I know that this was more common many years ago (60's, 70's and 80's) than it is today, especially with the attitudes regarding how it could be construed as child abuse, but how many of you had some guidance or coercion into dressing as the opposite gender? This could also be answered from the standpoint of whether or not you have someone who knows and supports/helps you with it today.
My example was that I was not out of daytime diapers by the time I entered kindergarten. My mother had me wear my sister's old dresses and skirts quite often for two reasons: first, that it was easier to change my diaper when she had direct access to it, second, that the humiliation and embarrassment of being put in my sister's clothes may motivate me to get out of diapers.
Later on, the summer before I started high school, I asked my mother what it was like to be a girl (what do you expect from a curious kid who is almost 14). Her suggestion was for me to dress up to get some understanding. When she found out I didn't mind the clothes, she asked if I would ever wear them again if she made them available for me. I didn't realize that answering 'yes' meant I would have my own girl's clothing.