When I was very young at around 8 to 11 years old, my crossdressing story began. I liked to wear my sister's clothes, including her dresses, pantynose, and when she entered her puberty and her breasts began to grow, her bras became my favorite objects. O often tried out her bras when she was not home. In fact, I was always a little overweight or quite chubby. My breasts always seemed to be blessed with gynecomastia. I was mocked a lot during my school time. My classmates often made fun of me and said that I should wear a bra. Then I began to wear my sisters', but they laughed at me even more. I remembered it was before my school time, I always liked a girl of my neighbor. She was planning on a party, but only girls were invited. So I put on my sisters dress and asked her to bring me along. I did it and had a good time that night.
When I was over ten years old, my tendency for crossdressing grew increasingly. I tried so hard to tuck my fat into the bra and I even made a cleavage. I also tried her underpants for many times. After that, as long as I was home alone, I would try my sisters' clothes.
But there were a few times that I was caught and luckily escaped the danger. Once I stole a bra of my sisters' and hided it under my pillow. But I did not know that my mom would wash the pillow case. She found the bra and asked me what was going on. I felt embarrassed, but I quickily thought out an answer. I said that my pillow was too short and I needed something to make it higher. Bra is the only thing I could find. I thought it was a perfect excuse. But when I looked back from now, I think there's huge chance that my mom didn't buy it.
Every time when my mother took me out for shopping, I would observe those mature women. What were they wearing? What did their bras and underpants look like? I thought one day I would wear them out on the streets. I would think if she wears a bra or not. I came to a conclusion. If there was one day you don't want to wear a bra but didn't want to be seen through, you should probably wear a loose top. It could easily be figured out if there was a bra on you if you wear a tight shirt.
I often wear bra to school and for a long time there was no problem with it. But there was one time that made me realize the danger of it. It was during my way to school, my friend and me were joking happily and walked along. Then he punched me in my chest. I was pretty sure he touched my bra and the bra was sunken by the punch. But fortunately, he didn't notice that. But it reminded me of a serious issue. From then on, I would only wear bra when I was walking alone, riding bike or other things that did not have to worry about intimate contact.
When I grew older and was able to buy clothes my own, I would buy myself female dresses, including bras, underpants, dresses and so on. I put them in my little case. It was my secret case. I would put it in my car and carry it with me everywhere.