What Happens When A Guy Wears A Dress
On October 24th a year or two ago, I grabbed my bag that was filled with a recently purchased black dress, gladiator heels, and a wig and made my way to Chicago’s gayborhood. It was a friend’s birthday and we had decided to wear dresses out to celebrate. Prior to this day we had decided to meet at a coffee shop to get ready, a coffee shop that sat on the edge of the gayborhood. We thought this would be the best place to do our outfit changes and quickly make it to a bar, limit the time we spent on the streets.
When I met my friends at the coffee shop, I noticed that it was packed; this specific coffee shop was home to the many sex workers and homeless youth that occupy the streets at night due to its 24/7 business hours.
All the people made me immediately nervous — I had been planning on getting ready in the single stall bathroom, but never really thought out the fact that I was going to have to walk in as a boy and then out as a “girl,” which gave me an odd feeling of anxiety. When glancing at my friend’s faces, I saw in their eyes that they felt the same, so after a quick deliberation we opted to try the store down the street to change.
But when we got to the store we found that they did not have public restrooms, thus our plan was foiled. After a quick deliberation we decided the parking lot behind the store would be most suitable for changing. We thought it should only take a few minutes.
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Twenty minutes later I was trying to master the art of pulling my dress straps up while balancing on the gladiator heels whose height made me realize that no gladiator would ever wear these abominable contraptions.
My friends were having even worse luck with their outfits; while getting dressed we tried to not expose ourselves too much to one another. After finally getting my dress on correctly came the task of velcroing my shoes. I threw my leg up on the loading dock area to reach them. Pushing my fingers down I was able to capture the cheap plastic beading that embellished the heels and at this moment was a feeling of accomplishment, I thought, all done.
As the Velcro married together I felt a bright light hit my side body and reflect off the beading of my heels; looking up I saw a large police SUV pointing right at my friends and I, my friends still half naked. It was the cops.
The officers approached us and asked for our IDs. They questioned if we had any drugs on us, while simultaneously searching our bags. After this question, they asked us “ladies” if we had been working that night. Working? I thought, why would I work in a dress?
Eventually after 15 minutes of running our IDs and making us shiver in the parking lot, they let us go and we didn’t even consider changing back into our originally clothing, we just needed to get out of there.
When reaching the road in front of the store we were automatically thrust into the public eye, the street was one the busiest in Chicago and all eyes were on the three ladies standing on the sidewalk, bags in hand and dignity in the alley.
Walking down the street my friends laughed and enjoyed all the stares from passing cars and the frequent whistles from people on the other side of the street. I, on the other hand, used my wig as a shield to hide my identity. And I blushed as cabs pulled over asking me to get in — not for a ride in their car, but more for a ride somewhere else, money included.
As we made our way deeper into the gayborhood stares and comments came faster and faster. Friends that I had known for years stumbled past me in drunken dazes, laughing at my bad drag without realizing that it was me.
I was gone, the dress and heels, and even the bad wig, erased my entire identity. Instead I dissolved into my environment and the expectations of that environment, the expectations that a boy in a dress with a bag of his belongings wasn’t out for fun, but probably was a sex worker hustling the streets. This dress made people believe I was a transgendered prostitute — a cheap dress, at that. And I was being treated like one as I stood in those streets.
To walk the one block down street took forever. My ankles gave way many times due to the high heeled shoes, random items were thrown from moving vehicles by drunken men and drunken words, and my heavy bag tugged at my shoulder while I shielded my face with my hands and wig. I felt exposed and I felt attacked and I felt too much.
When finally reaching the end of the block, my friends and I looked like we had just walked through a war zone, we were shaken up — we always thought drag was supposed to make people happy, people laugh, people talk to you. Instead our drag put us under scrutiny, we feared being attacked, the dresses made us scared to be on the streets.
When we took a break at the corner, surrounded by all the gay bars in the gayborhood, a gay couple approached us.
“Hello. Can I ask you a question?” said one of the men as the other comforted him from behind, rubbing his shoulders. I immediately thought these were Johns looking for a good time, so I snapped back with a sharp tongue, “What?!”
“Have you seen our son?” He pulled out a photo of a young boy no more than 16, “he has been missing for a month and we know he hangs around here in your crowd.”
I just stared at the photo mouth agape, saying nothing. This boy looked not so different than me.
“Please, please help us; you have to have seen him!” They both yelled at me, my friends both staring at me, waiting to see how I handled the situation. I began to shake, this was too much, these men were looking for their homeless son who was involved in sex work, and now thought I was in that same group. I needed to change.
“I am sorry, I can’t help you — I don’t know him at all,” I barked back.
“Thanks,” is all the men could say in response while looking at the ground, defeated.
As they walked away, tears rolled down one of the men’s cheeks. This seemed to have been a ritual for them, searching every night for the son they lost to the streets.
Once they were out of sight, I grabbed my bag with my boy clothes in it and said goodbye to my friends. They laughed at me and tried me to convince to come with them into the bars, it will be better in there. The interaction with the two men left me raw, and no alcohol would soothe that, I needed out of that dress and back into my life.
Walking down a side street that had little light I headed back toward the train station that I originally got off at. I threw on a hoodie I had in my bag covering the dress and threw on the jeans I had stored away while slipping off the heels and replacing them with my boots.
My boots clicked and my hips swayed as I approached the train station to go home and a car drove past me, like the cars did before while I was in my dress. The driver rolled down his window, looked at me and yelled “faggot” as my boots clicked, my hips swayed and my hand reached for my train card. It was time for home. 
