One day, a few weeks before I was to turn ten years old, I was climbing the stairs to my bedroom with my younger brother, a year younger than me. We shared the large bedroom upstairs with our youngest brother who had not yet started school. Our older brother had his own bedroom as did our sister. All three bedrooms were upstairs and our parents slept downstairs. “Do you want to hear a secret?” asked my brother. Whether I said yes or not I cannot recall, but he had a secret and he did not want to keep it to himself so he proceeded to share his secret.
“Yesterday I overheard Mom and Dad scolding Mark. They were really mad as they had caught him wearing one of Cheryl’s dresses.” Mark was a year older than me. Bryan was already laughing as he finished up his story so I naturally joined in his amusement. We spent a few moments chuckling over the sight of Mark wearing a dress. Now I have no way to know if this story was true or not. Mark and Bryan did not get along very well and it could have been a fabrication. It is also not entirely unlikely that Bryan had been the one caught in one of Cheryl’s dresses and was trying to plant a seed of confusion in case a story ever came out that he had been the one caught. For my purposes, the veracity of the story is totally inconsequential.
If this had been a scene from a movie, as soon as I heard the words ‘they caught him wearing one of Cheryl’s dresses,’ they might have had fireworks going off in the background. My life had just changed. I truly did find myself wondering why the idea of wearing one of my sister’s dresses had not occurred to me before. Now I am not saying that wearing her clothes was suddenly a solution I had not considered before. That would require there to be a problem I was trying to solve. I knew instantly I wanted to try on some of Cheryl’s clothes. And while I had never really struggled with ways to express myself as a girl before, the thought of dressing up in her clothes was like finding a hidden door and knowing beyond the door were tons of treasures.
Without suggesting that Mark ever actually tried on one of our sister’s dresses, he had one advantage that I did not have. He had a private bedroom. I shared a bedroom with two brothers. With four siblings and my parents it was nearly impossible at a nine year old boy to find the opportunity to sneak into her room and try on some of her clothes. However opportunity was not my biggest obstacle to overcome. I also needed to find the courage. Almost as quickly as I found myself wanting to try on some of her clothes, I became certain that I would love wearing her clothes. I knew that if I did it once I would want to do it again. And again. And again. I was almost ten years old. (I would be ten before I first found the courage and the opportunity to visit her room and try on her clothes.) I was old enough to understand that because I had a penis I was a boy. I accepted this as one of the unchangeable laws of the universe. I did not know why I felt so strongly about dressing up as a girl but I knew it either showed me to be a sinner and destined to spend eternity in hell. Or it proved there was something wrong, terribly wrong with me. It would be several years before I came to understand that I was not alone in my desire, that I was not the only boy in the whole wide world who wanted to be a girl.
If you are attentive to my words, you may have noticed that one moment I am talking about dressing up in my sister’s clothes and the next I am talking about my desire to be a girl. For me it is all but impossible to discern a time when I wanted to dress up as a girl from my desire to live my life as a girl. I did not see myself as the proverbial ‘girl trapped in a boy’s body.’ Society had spent the last ten years instilling in me that boys are boys and girls are girls and that since I had a penis I was a boy. At the same time, I knew how much my parents had wanted me to be a girl. I did not want to be a girl because I was a girl. I wanted to be a girl because my parents would have been happier and wearing dresses would be expected of me.
I spoke of courage and opportunity. It would be several months before I found both at the same time and first tried on a dress. I can recall often standing at my sister’s bedroom door and wanting to turn the knob to open the door. Only to chicken out. I knew that dressing as a girl would change my life and change it in a way that would define me defective, different, sinful. Alone. I also had to be fearful of being caught by my parents as Mark had been caught. I was not concerned so much about being punished with a spanking or getting grounded. I knew that if I caught steps would be taken to ensure that I could never dress up again in Cheryl’s clothes. Dressing up a first time meant I would be placing myself at risk to be caught. I could not risk any caught. No one could ever know. I am not really certain that I saw my future as a future of lies, secrets and scheme before I first tried on a dress. But a part of me knew that if I was ever caught wearing a dress, I would have no true defense. All I could say is that I really, really, really wanted to wear a dress.