Well, I'll start, duh, hey.
When I was 10 years old a friend of mine, who was a girl, thought I'd look cute as a girl, so she dressed me up, and bam! I looked real for a 10 year old kid, I was a little guy then, and I had longer hair, so I got mistake by substitute teachers every so often. It was fun, and we did it a few more times as we got older. I think it was when I was 12 1/2 when we stopped, because she moved away. At that time it was so much fun, but I was at an alternative school at the time. I was having a lot of problems, being bipolar and all, so I couldn't say anything or I'd get bullied more, and probably get beaten up. So, I had to lay low. I crossdressed once in a while in my freshman and sophomore year of high school, but then, I met a friend who crossdressed during Junior year, and we had a little fun. After graduating from high school, my dressing needed to be fed because it was a good year since I last did it, so this winter I came out to my two closest friends. I was extremely surprised how well they took it. My friend Jo said she wanted to go shopping with me sooner or later, basically when I'm ready. So now I'm working on getting in better shape, my hair is already at a good medium length, so just need to grow it a few more months, and I'm working on getting clothes, so I'm doing a lot better than a week ago. :P My best friend still finds it kinda funny that I'm into crossdressing, but he has no problem with it, and Jo hasn't said much since, but she is really good to me. I love them both. So...how did you start?