That One Time I Failed at Sex Work

I almost became a whore once. One late summer evening a couple years ago, I threw on my sluttiest corset, my best pair of ass-hugger jeans, and my crimson pea coat, and hopped the L toward a nightclub known for being frequented by trans women and the kinds of guys who are really into girls like us. I was determined to find some rich bastard and give him the night of his life, in exchange for no less than $1,000. Or maybe $700 or $800…I’ve always been soft when it comes to money, and I despise haggling. Hell, I probably would have spread my legs for $500.

But let’s rewind a few years. I was a good kid growing up. I played by all the rules my parents and schools neatly laid out for me — I went to church three times a week, did all my homework, never lied to my teachers. I was a straight-A student and a reclusive nerd whose only hobbies were playing Nintendo and eating pizza, secure in the meter-thick bubble my parents were raising me in. Most of my “friends” bullied me relentlessly until high school (when I found my first real friends, who loved fast food and gaming as much as me), and I grappled hard with depression and the ominous, creeping feeling that I was a girl stuck in the wrong body. But I continued to excel academically, graduating eighth in my class before moving onto life as a military cadet at Virginia Tech. I was smart, I respected the people who gave the orders, and I had a growing passion for aviation, so I figured I would make a fantastic pilot. Right?

Well. The very first morning, when I woke up alone in the chill darkness of my bunk, my ears picking out the first few riffs of Guns N’ Roses’s “Welcome to the Jungle” blasting out of an amplifer the cadre had dragged into the hallway, just before kicking open every new cadet’s door and screaming at us to get our asses down the hall and into formation — let’s just say the bubble popped. I’d never had sex, never had a puff of weed or even a single sip of alcohol, yet there I was, a chubby, petrified eighteen-year-old kid learning in one horrible moment that the world was a very different place than what I’d been led to believe it was. Worse, I was a completely different person than who I’d been led to believe I was. After all, I was “supposed” to become a pilot, and my whole family was counting on me to succeed — but if I hated the cadets so much, how could I possibly expect to enjoy life in the real military? My already fragile self-image had crumbled to dust before I’d spent a week away from home.

After the longest four months of my life, I got out of the cadets, but I stuck with college. I rediscovered my love for writing, started working for the campus newspaper, and went from making Cs and Ds to As and Bs, my reward from professors who encouraged my creativity, understood my passion, and gave room for my ideas to breathe. I had sex (mostly with my on-again, off-again girlfriend — mostly), went to parties, drank more alcohol than I should have, and tried weed, but I didn’t go crazy, as my parents were terrified I would. And then one day, the ride was suddenly all over, and I had to walk across that stage, grab my diploma, and think about the next step.

The next step turned out to be more panic and denial, in the form of law school. I sure as shit didn’t want to be a lawyer, but career prospects for English majors were (and still are) bleak, and I had no idea what else I was supposed to do with my life. With my GPA, I knew my family was expecting me to attend grad school anyway; why not law? I scored 150-something on the LSAT, and I accepted an offer from a private school in New England. Maybe, after three more years of grueling study, my family would finally consider me a success. Maybe I would finally consider myself a success, too.

What I didn’t realize, of course, was that by choosing to base my life around those sorts of impossible expectations, I was making the same mistake at twenty-three that I’d made at eighteen. Except this mistake ended up costing me about $250,000 (and growing by the year, as unpaid interest continues piling up). I hated law school and the entire state of Rhode Island almost as much as I hated the cadets, but at least I still had my personal freedom, and at least I still had alcohol, which was starting to gain more of a foothold in my life than I was comfortable with. I was miserable, but a year in, the final facade crumbled — and I decided to transition, rather than damn my own future with more fear and self-delusion. The last two years of law school were hell, but I was buoyed by friends who believed in me, and more importantly, by the hope that I would get to truly live my life for the first time, as the real me. No more false expectations, no more lies. Just me. Not surprisingly, my parents shunned this notion — as good Southern Baptists, it was expected of them — and I grew more and more distant from my family.

Back to the ass-hugger jeans. Several years had passed since I received my law degree, and it had been mouldering in the back of my closet since graduation, in the shadowy spot where my gender and sexuality hangups had once gathered dust. I’d been recently fired from my brief job as a publicist in order to save face with a client who’d been disgusted with me, and had started working in the mailroom of a small publishing company, packaging books, monitoring boring social media accounts, writing press releases, and proofreading manuscripts for zero pay. It had taken me months of searching and at least a dozen failed job interviews to land a position on the ground floor of that company, which constantly teased me with the possibility of a career in publishing if I stuck with them long enough. (In early 2016, they sold out to a larger publisher, and no longer have physical offices.) Starbucks wouldn’t even hire me as a barista; during that particular interview, the store manager had grinned ruefully as he explained that I was “overqualified.”

After my six-month “internship” at the publishing company was over, my bosses told me to clear out my stuff to make room for the next crop of indentured servants. But they liked me, and they decided to throw me some freelance editorial work, which usually amounted to somewhere between $500 and $1,000 a month. (For some perspective, I lived on the outskirts of San Francisco, and my rent and utilities alone were about $800 per month.) I scraped by for upwards of two years, and I’m extraordinarily lucky that I’ve always had roommates who were willing to help me. I have to credit my mom and dad, too; they might be intolerant bigots, but the few extra hundred bucks they sent whenever I had to beg would, at least, ensure I didn’t starve (to reprise my father’s words to me shortly before I moved to California). Were it not for the grace of the people who (still, somehow) love me — and who I still love dearly — I have no doubt I would have ended up homeless and destitute.

But that particular night, with bills piling up and my back to the wall, I’d had it. I’d had it with my meager pay, with all the embarrassing, failed interviews, with all the sneering and staring and lust-filled gazing I faced every single day on my way to work at a job which barely paid me enough to survive. And I’d had it with groveling for handouts. If American society expected me — a trans woman — to be nothing more than an outcast and a sex object, then that’s exactly what I would be, I reasoned. I planned to excel at it, too, despite being a complete newcomer to the world’s oldest profession. It was honestly a pretty exciting thought. Troll bar for clients, collect cash, go to seedy hotel, spread legs, fucky fucky, kiss goodbye, then do it again. How hard could it be?

I completely whiffed. I flitted around the club all night, chatting and sipping free drinks with anyone I thought looked like a potential mark. Maybe I was coming on a little too strong, but they all knew what I was there for. The closest I got to scoring was with a former CIA employee in his fifties or sixties who told me that, although he wouldn’t engage my services for the evening, he was happy to buy me a drink or two. I spoke with him for about an hour, and he told me the story of how he’d met his wife decades ago in that very same club, in almost the exact spot we were sitting. Tonight happened to be his first night back at his old stomping grounds in about as long, he said, and he couldn’t believe how little it had changed.

When the house lights came on at last call, I got the attention of the bartender — a beautiful trans girl with long, black hair and skin the color of polished bronze, who looked to be about my age — and asked her who I should speak to about getting a job barbacking or serving cocktails. As the other patrons slowly filed out into the night, she walked around the bar and, with tears welling in her eyes, threw her arms around my shoulders in a tight hug.
“Go home,” she said, her voice breaking. “Please. Just go home. You don’t want this.” I nodded and said thanks, blinking back my own tears. On my way out the front door, the club’s manager threw my overcoat at me and told me to get the fuck out. He knew what I was there for, too.

I still had $20 in my bank account, which was enough for a cab ride back to my apartment in the Sunset. I walked a block or two and was preparing to round the corner toward one of the busier streets downtown, when I got stuck at a crosswalk waiting for the light to change. Standing next to me was another young, attractive trans woman who happened to be in the middle of her shift. She was wearing a black mesh tank top which showed off her enormous breasts, fishnets that looked like they’d been through a blender, and a vinyl skirt which barely covered her ass or the bulge in front.

“Hey,” I said, offering her a thin smile as my breath turned to mist, “any luck tonight? God, aren’t you freezing?” I offered her my coat, but she politely declined, explaining that she wouldn’t have much luck finding potential clients if she was wearing one, which made sense. We shared a laugh, then I asked if it would be all right if I accompanied her for a little while, just to talk. I was feeling dejected and I couldn’t wait to get out of my too-tight corset and jeans, but the prospect of sharing even one quiet hour of solidarity with this prostitute compelled me to linger.

“Yeah, sure!” she said, beaming at me. “Come on!” And just like that, we were off trotting down the street together in our high heels, me with my hands stuffed in my pockets and my eyes on the piss-stained sidewalk, her chatting away merrily, stopping only to bend over and push her tits toward any passing group of johns who seemed half interested. She could expect to earn a few hundred bucks on a good night, she said, but some evenings were better than others (ones that didn’t include a random stranger tagging along, I suspected). When I asked her if she had a place to live, she told me no; however, she’d been staying with some supportive friends, and she tended to drift from place to place, with not too many nights spent outdoors or hungry, which was good.

We walked together for a while, just joking and getting to know each other. Around 4:00 a.m., my feet were too sore for me to stand on, and I can’t imagine hers felt much better. I hugged her goodbye and crawled into the back of the cab I’d managed to flag down, gave the driver my address, then burst into tears as soon as he hit the gas. I rode home sobbing in the darkness and feeling like the biggest, most privileged piece of shit to ever somehow grow legs and walk the earth. I’ve never been ashamed to be trans; but in that moment, I was ashamed of who I was. Ashamed that I couldn’t hack it, even as a whore. And ashamed most of all that I had nothing but idle conversation to offer the woman I’d just met, standing out there by herself on some foggy street corner in downtown San Francisco during the wee hours.

I was so scared for her, consumed by the fear that I’d wake up in a day or two and read that she’d died of exposure, or that she’d been stabbed or shot to death like so many other trans women whose names and faces occasionally crop up in the obituaries, before forever becoming heartbreaking statistics. It didn’t take much of a logical leap for me to imagine myself standing there in her shoes, shivering and alone. And before long, death would come for me as well.

The next morning, I woke up, then called my parents and asked them for a little extra cash to help me make it through the month. As always, they begrudgingly assented, saying that they were worried and that they wished I would come back to Virginia to live with them — as their son. I thanked them for the help, told them I love them, then hung up.

These days I still have trouble finding work, and I still lean on my friends and family (which, for over a year now, has included my wonderful partner) more than I want to. But I won’t try to sell my body again, because I know I’m not brave enough to.

And now and again, I still think about that chick I walked the streets with for an hour, wondering if she’s still out there, living her own truth despite it all.