by: Zach Stafford
Note: This is written in response to the rise in youth suicides due to bullying and the ways in which people in our society are facing violence due to how they look in public. This is a personal story of how a dress, a little black dress, can affect some one’s life…and not in the way Carrie Bradshaw always talked about.
It was my friend’s birthday. He had just turned 27 but looked only 23. A few weeks prior to this day, we joked that he and I — with our other friend, Jake — should throw a dress party in celebration of his day of birth. We laughed at first, but then our laughs turned into curiosity, and this curiosity turned into a date: October 24. As the date approached, our plans — like many of our plans — fell through the cracks of our busy lives, and we opted to take the dresses we bought out on the town, specifically to Boystown — the famous Chicago gayborhood.
On October 24, I grabbed my bag filled with my recently purchased Forever21 Black dress, gladiator heels and a wig that looked like I stole it from a circus and made my way to the train station to head towards Boystown. I didn’t have make up with me and hoped one of my friends that I was meeting at a coffee shop would have something that matched my complexion. Makeup wasn’t too important; if anything, I thought: I will just look like a boy in a “skanky” dress.
As the train approached my stop the voice on the train intercom barked, “Doors open on the right at Belmont”. I prepared myself for a night out in a dress on this chilly autumn night. My boots clicked as I walked out of the train and onto the platform, heading towards the stairs to the street, these boots sounded like heels walking which made people around me quickly glance down, making sure I wasn’t in heels…people always give me that look when in those boots.
As 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 of Boystown 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, and so after a quick deliberation, we opted to try the Walgreen’s down the street to change.
Once arriving to Walgreens, we found that they did not have public restrooms, and our plan was foiled. We went to the parking lot and scanned the surrounding businesses to find somewhere to accomplish our gender bending mission; however, the 11 o’clock hour gave us little hope for anything to be open besides bars. With everything closed, we decided the parking lot behind the Walgreens would be most suitable for changing – I mean, 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, and while getting dressed, we tried to not expose ourselves too much to one another, mainly because we were still outside and we didn’t want the wind to blow on our gentials.
After finally getting my dress on correctly came the task of velcroing my shoes — yes, velcroing — and to reach the strap on my shoe, 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 I felt 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. “Shit.”
The cops walked over with ready hands on their pistols. I didn’t shake surprisingly, but instead thought, “Dammit. My dress keeps riding up; this isn’t cute.” My friend, Jake, asked the cop, “Is there a problem,” and I yelled in my head, “Duh, there is a problem, you are half naked in a cheap dress with your sneakers on. You’re not even matching!”
The officers asked for our ID’s and asked if we had any drugs on us, while also 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?”
Then I realized. They thought think we were transgender prostitutes, hence the questions about drugs. Eventually after 15 minutes of running our ID’s and making us shiver in the parking lot, they let us go, and we didn’t even consider changing back into our boy drag. It was time to get out of there.
When reaching the road in front of the Walgreen’s, 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, I mean the dress was so short it should of been a shirt, and I even blushed as cabs pulled over asking me to get in…not for a ride in there car, but more for a ride somewhere else…money included.
As we made our way deeper into Boystown, the 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…Zach.
Zach was gone; the dress, heels and 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, was sinking deep into my being. This dress made me into a trans-prostitute, a cheap dress at that.
To walk the one block down street took forever. Between my ankles giving way do the high heels, the random items being thrown from moving vehicles and my heavy bag that tugged at my shoulder as I shielded my face with my hands and wig, I felt exposed, I felt under attack, I felt too much.
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. Drag we always thought was suppose to make people happy, make people smile, make people talk to you. Instead, our drag put us under extreme scrutiny, and we feared being attacked. The dresses made us scared to be on the streets.
When we took a break at the corner, standing catty-cornered from all the gay bars in Boystown, 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 responded back, whipping out a photo of a black young boy, “he has been missing for a month and we know he hangs around here in your crowd.”
They think I live on the streets.
“Please, 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 thought I was in that same group. I need to get out of this damn dress.
“I am sorry; I can’t help you. I don’t know him at all!” I spouted out.
“Thanks,” the men replied while looking at the ground.
They walked away, tears rolling down one of the men’s cheek. This seemed to have been a ritual for them, searching every night for their 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 me 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 towards 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…the boots that clicked.
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.” My boot clicked, my hips swayed and my hand reached for my train card. It was time for home.
Zach Stafford is a Tennessee writer currently living in Chicago. His work has appeared at places such as: USAToday, Thought Catalog, The New Gay, and Bookforum. Outside of writing and watching Ally McBeal on Netflix, Zach is in the process of applying to PhD programs in the field of Cultural Geography & Urbanization. Also, Zach is the Production Assistant and a Contributor to the 50Faggots.com web series, which explores the lives of effeminate gay men in America. Follow him on Twitter @zachstafford.
