Origins of Jess the Crossdresser

The earliest moment of me choosing to wear a dress I was really young, perhaps four or five and I put on a frilly dress and walked around.  Of course at that age there were very few social repercussions and it was likely considered cute.  As we age however that changes and we learn that there is a gender line that is not be crossed.  Luckily as kids we are allowed to play dress up and there is always a steady supply of dresses in the dress up box.  At these young ages it is the outerwear that is of note and the idea of different underwear never really occurs to us.

I suppose some could say that if you've read one personal story, you've read them all.  Nevertheless, I never tire of reading the personal childhood stories of those who identify as crossdressers or transsexuals.  For many, the early years were quite similar.   Origins of Jess the Crossdresser, is another one of these childhood stories that may be much like your own.