It was around the age of 8 where I started to protect myself from negativity that might come my way. I knew that I would be looked down upon if anyone found out I was wearing girls’ clothes. So I hid it very well. Then I also hid ANYTHING that might make people think I liked to wear girls’ clothes. At age 11 or 12 I made people start calling me James instead of Jamie. I got rid of ALL my stuffed animals (still get weepy about this – what a stupid thing to do – at times they were all I had). I made sure I didn’t ever do anything that a girl would do. Well, as much as I could anyway, I was still a bit of a crier. My sensitive side seemed to always make it past my defences to the surface.
I now call this protector of my ‘self’: James. He, and he is a he because he had to be for the whole thing to work. He was so good at protecting me. Unfortunately, this protecting led to my ‘self’ being buried deep under a weave of lies. Some of those lies were ones he was telling me. I came to believe them, at least on the surface. Or at least, James, believed them. And that was enough for James to fool everyone, even himself. Other than one mess-up with leaving something out in my bedroom at age 14, there was no clue.
So, keeping secrets and lying to yourself can have a profound effect on one’s psyche. I was so incredibly shy and introverted (much different than how I was before age 7) that the thought of asking a girl out was horrifying.
When I reached adulthood I still hadn’t had any girlfriends. On the rare times I did manage to do it, I’d get hurt. Like at grade 12 grad. I had asked a girl to go with me, and she said yes of all things. I was ecstatic. And that lasted a couple days, until she phoned and said she was really hoping some other guy would go with her, and there was still a chance of that, so she’d rather just go without a date just in case.
Then at age 26, I had a really good friend (who was more of an acquaintance at this time) set me up with a friend of her’s. I was smitten, and so in love with her. Everything seemed to be going very smoothly. But, I had zero experience with relationships. And as a result, I went kinda fast (not in wanting sex kind of thing) but just in being in love. It wound up scaring her. She had gotten caught up in it too (she hadn’t had many relationships). It fell apart after 3 months. I had an underlying feeling of keeping secrets from her. Which, of course, I was.
At age 27 I was playing an online MUD. A fairly addictive one, and was playing it quite frequently. I could be a little less introverted and shy online. There was this false sense of anonymity. There was a female character (who I knew was actually played by a female) that I became friends with. For some reason, and I still don’t know what prompted me to do it, I told her that I dressed in women’s clothing.
I was expecting the worst, and hoping for the best. I got the best. She thought it was amazing. Amazing that I had the guts to tell her, amazing that I was a cross dresser. She asked a bunch of questions like what kinds of clothes I liked, when I started, etc… It was a bit liberating (a ‘lot’ I thought at the time, but not so much) to finally have someone to talk to about it, that didn’t think I was evil, or insane.
We actually wound up kinda/sorta going out for 4 months. She was a tall girl, and gave me a bunch of her clothes. I never got up the nerve to dress for her though. I had no wigs, and no idea how to use makeup, and I did not want to look like a guy in women’s clothes in front of her.
After this experience, I decided I needed a confidant. I chose my best friend’s girlfriend (we’ll call her Glenda because that’s SO not her name). One night, I got up my nerve, and wrote a really long email to Glenda. The reply came and she was totally ok with it. I now had someone in my corner, whom I could always talk to, fall back on. It was great.