By Rikki Dubois

When I found out that this edition of the Cockroach was about disguises, I decided to to tell you a story about my own masquerade. As a woman who was raised as a boy, I did my share of cross-dressing. But all these times I cross-dressed, I was in the safety of my own home. One day, I decided that the time was right for me to venture out into the public dressed as my true self.

On a particular Saturday, when everyone was out of the house, I decided that this was the day I would go out. I made sure I had shaved everything closely and completely. I went to my closet and took out my favourite black satin skirt. I matched it with a white blouse, black pantyhose and black pumps. I did not have a lot of make-up at that time, so I had to make do with some red lipstick. At this time in my life, I carried a messenger bag instead of a purse. This was where I kept my wallet, iPod, book and cellphone. No iPhones back then. So in my messenger bag, I also put a pair jeans and a T-shirt for me to change into before I came home.

I looked in the mirror and I liked what I saw. So now I was ready to go out. But where do I go? I thought that someplace in the Osborne Village would be good because I figured that with all the odd people who hang out down there, I would blend in. But where should I go? I had heard that the Second Cup on Corydon Avenue was trans-friendly, so I decided to start there.

I wasn’t sure exactly where the Second Cup was, but I drove west down Corydon until I found one. I don’t know if this was the right one, but I went in anyway. I was very nervous, but this was something I needed to do. I parked my car and I sat there for a couple minutes taking deep breaths and getting up my courage to go in. I got out of my car, walked to the door, went in and walked up to the counter. I acted very nonchalant, like I do this every day. I figured that would be important so that I wouldn’t stand out. I ordered my coffee and then went and sat down by the window.

While I sat there, I took out my book and started to read while I slowly sipped my coffee. Once in a while I would look up to see the people in the place. A woman who was older than I was came in with her husband and when she looked at me, she smiled. At the time I figured she knew who I was and smiled because she approved of the way I looked. But since I’ve changed my gender to a woman, I’ve discovered that women tend to smile to each other on a regular basis.

I finished my coffee and with the thoughts of the smile from that woman on my mind, I felt brave enough to attempt a visit to someplace else. I thought I would try a little bit of shopping, so I went to the Giant Tiger on Ellice Avenue. I chose this place because I figured there was no way that anybody I work with, or who knows me, would come out this way. Well, I parked my car behind it and, feeling a little bit braver than I was earlier, I just jumped out, walked to the door and walked right in. I walked around the store and looked at female garments in case I wanted to buy something nice for myself. But after strolling around the store for about 10 minutes or so, I found that there was nothing that I really needed at the time, and so I decided to leave.

At that point, I decided it was time to go home. I got in my car and started driving outside the city. I stopped on a side road to change out of my skirt, blouse and bra and put on my jeans and T-shirt. I took a wet nap out of my messenger bag and wiped the lipstick off my lips. When I had everything cleaned up and was back in my drab clothing, I went home.

As I went home, I was feeling sad for myself. The elation that I felt from walking around in a skirt was gone now. I was back in my male clothes and it brought me down. However, this first foray into the public dressed as a woman proved to me that I can do it. That I will be accepted as the woman I was born to be.

When I started this story, I said that I was writing about a masquerade. But looking back, I find that my masquerade started the day I was born and carried over for 48 years.  I only removed the mask in June 2010 when I started my real life as a woman.


Article by Rikki Dubois, a transgendered writer from Winnipeg. Her book Muffy was Fluffy helps children understand what it means to be transgendered. Order it today from McNally RobinsonMcNally Robinson.

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