Sloppy Firsts

CW: Sexual Assault

(“Sloppy Firsts” is a reference to the name of the first book in a teen lit series I loved as a kid)

I began my foray into sex work by failing miserably. I was in my early twenties attending an art school in Baltimore that my family could hardly afford or justify affording. I was living modestly and committing petty theft to make up for the difference between what I could afford and what I wanted. I bought into the internship industrial complex and volunteered my free labor to an artist in Brooklyn during one summer, hoping for mentorship and an in to the NYC art community. I had an apartment in Baltimore, but I was homeless in NYC. I agreed to the internship, believing I could get into sugar dating and encounter a daddy who would solve my housing situation. I set up a Seeking Arrangement profile hoping to find a sugar daddy like my friend who I visited one weekend at her invitation. She is a pretty white woman, and she had just moved in with her older tech bro daddy. They lived together in a gorgeous penthouse apartment in Manhattan that was everything I’d ever dreamed of. I wanted that. I wanted to find one of those. At the time I was hesitant to even call her partner her “sugar daddy,” as if it was a derogatory term. I didn’t know how she viewed her relationship, if it was emotional and she was a “kept woman,” or if it was explicitly a financially based partnership. Whatever it was, I wanted it, and seeing her proved to me that it was possible. But I was naive. I knew her world was different from mine, and yet I felt that her reality was accessible for me, a black and indigenous nonbinary person who had recently shaved their head and refused for moral reasons to shave any of their body hair.

The veteran sex worker in me cringes at the level of unpreparedness with which I began this journey, but the reality was that I didn’t have any viable mentors. My friend had happened upon her tech bro daddy at a conference, she hadn’t had to navigate digital sugar dating and didn’t have any tips for me. At that time, there was much more of a clandestine silence around sex work. There weren’t a lot of guides aside from what Seeking Arrangement offered, and that site is notorious for verbally dodging the label “sex work” (for numerous reasons, primarily legality and liability). My first profile was full of misconceptions and language informed by porn. I was black, which translated to “ebony”; I was in college, which translated to “barely legal”; and I was small, which translated to “petite”. I didn’t know what beauty meant for a person like me. I grew up in Oklahoma where black did not equal beautiful. I didn’t know anything about makeup because I’d never cared to learn. I didn’t know what men wanted, I just knew that for whatever reason, they seemed to want me. I’d dealt with sexual advances and overt propositions from men since I hit puberty at eleven. I knew I was an object of lust, the question was how I could harness that for my benefit. How could I turn unwanted attention into a housing situation?

It was brash and poorly researched, but it was also an incisive observation. Even with my queer looks, I was subjected to the male gaze. But I wasn’t asking the right questions. What rate did I expect? What services was I willing to provide? What does a successful profile look like? I had an answer to the latter question: a successful profile began with whiteness. BIPOC like me were not the faces featured on the website. Since there was no blueprint for a person like me. Even now, I feel a pang of sadness that there was nobody I could look to for help because that lack of guidance and support led me into dangerous situations.

I began interning for a black performance artist. She was making edgy work exploring gender and body commodification, wearing masks that made her look like Black Barbie. My professors had suggested I look into her since my portfolio was exploring similar themes. I scheduled a visit to her studio and asked if I could assist her over the summer, and she agreed. I didn’t know where I was going to stay. I knew a lot of people in the city, but none of them well enough to ask if I could crash at their place for a few nights per week. The other problem was that New Yorkers are notoriously stingy with their space. Space is the one commodity nobody has enough of to share. I had hoped I would find a friend who might let me sleep on their floor, but continued pursuing sugar daddies in case that fell through.

I didn’t know how to filter for viable candidates. Instead of focusing on searching for clues to verify my candidates’ financial circumstances, I was primarily concerned with avoiding anybody too old or ugly. Additionally, because I was unfamiliar with the economic geography of NYC, I wasn’t filtering according to burrough. If I was smarter, I would have narrowed my search to affluent areas. If you can’t afford the Upper West Side, you can’t afford me. I chatted with a number of possibilities, labeling them in my phone as “Jay Possible Sugar Daddy” and other irreverent names, but as is the case with all dating sites, the number of people actually willing to meet is a much lower margin than the number of matches you might make.

I ended up going on two dates. The first one was with a man who owned a carpentry company. He was a tall white man in his mid fifties with a substantial gut. He reminded me a little of Dan Conner from Rosanne. We chatted over beers. I was terrified, and embarrassed to be seen with him. He was easily double my age, and I was young enough looking that I got carded by both the bouncer and the bartender. I felt as if I was a prop child for To Catch A Predator, and Chris Hansen would pop out at any moment. We went for a walk to a park nearby, and he asked if he could kiss me. I didn’t know how to say “no,” so I nodded in agreement and kissed this man in broad daylight without him paying me a dime. I was overwhelmed with repulsion and shame. I felt so visible. We were what we were, and I couldn’t handle the idea of anybody seeing me with him. I made up an excuse to leave and practically ran to the subway.

Ambitious baby heaux that I was, I’d lined up a second date for right after the first one. I was flustered, but undeterred. This round I was meeting a man who from his profile appeared to be at least reasonably decent looking. He was a black man in his early forties. I’d picked him for his looks, even though his profile raised a massive red flag, stating that he wasn’t looking for “someone just out for money”. That’s always the most perplexing flex. Why put up a profile on a sugar dating site if you are not looking to pay a sex worker for their time? But I hoped, contrary to every signal, that I might convince him to pay me for my time. We met at a restaurant on the Upper East Side and he bought me dinner. It was a casual dining spot, nothing that would hurt his wallet. I don’t remember exactly how it came about, but I’d set up our date with the understanding that I would be spending the night at his house. I was desperate. I didn’t have the money to afford a hotel or an Airbnb, and I desperately needed a place to stay. I followed him to his apartment in Harlem. It was a rough area, and his apartment was tiny. As soon as we arrived, I realized with certainty he would not be able to pay me and had never intended to. I hadn’t negotiated payment, so while he was shitty, it was also my fault. I resigned myself to the reality that I was stuck, in a sketchy shoebox of an apartment with a strange man.

He put on a TV show and decided he would make his move. He started kissing me, jamming his tongue down my throat, and he roughly pulled down my shirt, exposing my breasts. He reached under my skirt for my vulva, and I froze. It was too much, and I had at no point consented to any of it. I was a twenty-one-year-old kid just trying to find somewhere to sleep. I somehow managed to articulate that I wasn’t ready. In retrospect, this guy is such a predator for pulling this, but I was also very naive to place all my bets on a man I’d never seen before. When I voiced my “no” he became grumpy. He wasn’t going to have his way with me, and clearly felt entitled to me, like it was his right. He reluctantly assured me that he wouldn’t hurt me-- he wouldn’t do anything I didn’t want. He pulled out a sofa bed for me, and went to his room. I began settling in, grateful for a bed. I was nearly asleep when he came back into the room and laid beside me. He started thrusting against me, reaching into my clothes. I felt utter terror. I started whispering “please don’t,” repeatedly.

“Please don’t. Please don’t. Please don’t.”

Please don’t rape me. He recoiled, realizing the line he nearly crossed, and left my bed, returning to his room. Before he closed his door he said, “I don’t want to see you in the morning.” His hostility was palpable. I couldn’t sleep at that point. I didn’t know if he would come back again. I laid still, trying to take up as little space as possible, trying not to make a sound. As soon as the morning came and the first rays of sunlight peeked in, I grabbed my backpack and left for the bus station.

I don’t know how I managed to develop enough courage for a second foray into the IRL sex industry after such a nightmarish first experience. I think the greatest difference was that when I began stripping, I had a community. A number of my friends from college had gotten into dancing before me. They all worked together at a little club called The Ritz. I’d come to know about their work through the art they were making about it. I was entranced by what they were creating, from a pop-up strip club performance art space; to gritty poetry readings; to an installation chronicling one woman’s journey from early sexualization to sex work. I felt like I was already woven into the narrative, even though I hadn’t had any success.

I began dancing because I needed the money, and one of my partners at the time was an experienced stripper. They patiently taught me everything they knew, and pointed me in the direction of resources like stripperweb.com to research before taking the plunge. They invited me to the club during one of their shifts and let me watch them work. They were in full female drag with a very fake looking blonde wig, and they were killing it. The men were eating it up, and they had a fluidity to their dance style I’d never seen before. Another friend of mine promised she would show me around my first night after I auditioned. The two of them supported me. They told me about Pleasers and helped me pick out my first dance outfit. I was very much a baby stripper, and they protected me. My little community made sure that during my first night at the club, I would be safe.

Now, years later, I am able to provide advice to baby sex workers to keep them safe— to help them avoid the dangers I faced. I’m grateful to be able to facilitate community and share my experiences. It’s not an easy path to take, but you don’t always get to choose an easy path.

***This is a bit of what I wrote for my foreword to How To Build A Hookers’ Army. Stay tuned for the release of this amazing book filled with the combined writings of so many extraordinary sex workers.