When I was five to eight years old I took my mom shoes, but that is how far I took crossdressing. When I turn thirteen my cousins (girls) left behind clothes in my house before they left to another state. I used that opportunity to put girls clothes on at night. At that time I almost got caught by my stepdad. I wore skirts, dresses, jeans, blouse, tops, and anything else I can find. Unfortunately, my stepdad throw all those clothes away.
The next time I crossdress was when I was fourteen and fifteen. That was when I slept in my sister room when she was someplace else. I shouldn't have, but I decided to try on some of her jeans, shirts, skirts, dresses, tops, etc...
When I turn nineteen, I got up the courage to inside target, Walmart, Burlington coat factory, to shop for girls clothes. I wasted a lot of money brought clothes that actually fit. Not like the clothes I sneak around and tried on in my past. By that time at age nineteen I let my immediate family know that I was a transsexual and my intentions to one day transition. So it was not a huge surprise to them. However they were shock when I wore girls clothes in public and around the house. they are still getting used to seeing like this. Its been three years and am 22 now.
Not too long ago I decided to go to an all girl department like JC Penny, Macy and so forth. I was afraid to do so because only girls are suppose to go to stores like that. Plus that where they have the most feminine clothes all for themselves. None of the clothes I had was good enough for me. There were a bit of problems shopping, but my positive experience outweighs my negative experience. Now I have good clothing to wear and been crossdressing for some time now.
its too bad that I did not have anyone to shop with me and help me find clothes. I have no friends or family willing to go with me. Although on a side note I feel more confident going into stores and getting what I want. I had a fun time trying on things that I like.