That One Night I Decided to be a Prostitute Because of JT LeRoy

By Josiah Hesse


Illustration by Lonnie MF Allen


In the church where I grew up, being a prostitute was the ultimate sin. Beyond theft, drug use, Satanism or even murder, selling your body sexually meant you’d hit rock bottom and would never be the same.

So, naturally, when the cab driver propositioned me, I jumped at the opportunity.


I was 22 and had just left Iowa for Denver.

There was nothing to leave behind, and nothing specific to pursue. I’d just met a girl in a bar who was on her way to Denver, didn’t have anything better to do, and agreed to split the cost of gas. In the two decades I’d lived in Iowa I’d accomplished nothing to endear me to my hometown, or my family. I never played sports, dated a girl, or held a job for more than a few weeks. I wasn’t lazy or nihilistic—just not very good at anything. Despite never skipping a day of school, I flunked a majority of my classes and by my senior year had only the credits of a sophomore. This was pointed out to me by my guidance counselor, who said I might as well stop showing up to school.

No one had been paying attention to this dilemma, least of all me.

The youngest in a poorly planned family, I was like the uneaten food on an overambitious buffet plate. It wasn’t my parents’ fault. They were kids when they had me, and developed their own insurmountable problems as adults. Before I left for Denver, it was if I’d spent my whole life in a dissociative state, like The Who’s blind, deaf and dumb Tommy—but without the pinball skills.  

The only time I’d really engaged with the world was in church.

It was a wild, pentecostal church that frightened outsiders with all the shaking, screaming gibberish1, dancing to insanely hypnotic rhythms. It wouldn’t be hyperbolic to say I was addicted, considering I attended some Christian event around nine times a week. I only felt alive when dancing in church (while the rest of the time I mostly thought about Hell and whether or not I would spend eternity there).

My entire identity was wrapped up in being a Christian, which made it so traumatic when my faith disappeared. I won’t get into the details. Suffice it to say there were a lot of things I never understood about God as a child, and always told myself I’d understand when I got older. So when the age of 21 arrived and I had no answers, only an ever-increasing amount of questions, my belief in God collapsed under the weight of them all.

When I left Iowa I was in the depression stage of grief.

By the time I got to Denver I was very angry.


I’d planned to go to college, but went to a bookstore instead.

After taking the GED test I was halfway through enrolling in the University of Colorado, but quit after a few weeks of hanging out with students and constantly asking myself: Are these kids really $200,000 smarter than me?

I decided to head to the Tattered Cover and just read books for free. This was back when the downtown store had two floors, and you could hang out from morning to midnight reading all the books and magazines your eyes could handle2. It was there that I found a new gospel in the biographies of Jane Fonda, David Bowie, Oscar Wilde and Hunter Thompson. My heart swelled from the poetry of Lord Byron, Sylvia Plath and Charles Bukowski. And my atheism and post-faith bitterness were amplified by the ideas of Tom Robbins, Christopher Hitchens and The Marquis De Sade.   

Though I still suffered under the weight of my old identity, the aftershocks of a life spent pondering the eternal torment of Hell kept me up shivering all night. I was desperate to sever the cord of pious devotion and jump groin-first into a life of sin and depravity.  

It was the mask of JT LeRoy that would give me this opportunity.

Androgynous, uneducated and mysteriously stylish in his wigs and sunglasses, LeRoy looked like a shy kindergartener playing dress-up in a Japanese thrift store—but he was a writer. I first encountered him in a Vanity Fair profile, and instantly knew he was everything I wanted to be. He wasn’t a highbrow, upper-class academic writer like the ones I’d met at the university, but the abused child of a truck stop prostitute, a heroin-addicted street urchin sex worker who (I was told) would haul a fax machine into public restrooms to send out his stories—which would wind up in the pages of SPIN, McSweeney’s, Vogue and The New York Times.

And he was only 24 years old, practically the same age as me.  

LeRoy was such a sensation, he was being courted for attention by all of my newfound heroes (Lou Reed, Winona Ryder, Bono, Carrie Fisher, Michael Stipe), many of whom would perform readings of his work at packed bookstores when LeRoy was too scared to appear in public. He was soft, vulnerable and visibly damaged, bucking the trend of the broad-shouldered, testosterone fueled writers who liked to punch and fuck their way through life.

I immediately began reading LeRoy’s books that very night, feeling a dark sexual charge, like a pleasant nausea, from his stories about truck stop johns who wear lacy panties under their wrangler jeans, enemas exchanged for heroin, and BDSM as a surrogate for maternal love. The stories weren’t overtly sexy, often they were abusive and downright unsettling, but they contained a self-loathing eroticism that rests in the hearts of all those with traumatic childhoods.

LeRoy’s life as a fashion-forward, gender fluid, drug addicted, San Francisco prostitute was everything the church warned me not to become—and I was desperate to become him.  


Hearing that East Colfax was where the prostitutes hung out, I rented a tiny room in a house across from the Ogden Theater. It was only six by nine feet, with no kitchen and a bathroom down the hall. Violence, crack deals and screaming babies filled the house, while I remained in my room, desperately trying to write stories as debauched as LeRoy’s.

While I’d transformed myself morally, I apparently still lacked the ability to hold down a job. I’d had ten of them in my first six months in Denver, mostly in restaurants and hotels. I was still slipping into these dissociative states several times a day, staring off into space, thinking of JT LeRoy and the story I was writing when I was supposed to be helping vacationers with their suitcases, or serving appetizers to hungry businessmen on their lunchbreak. Whenever the smallest task was completed, I’d sit down and start reading a book, my co-workers busily rushing by, looking at me with disgust and hatred.

I wasn’t a rebel. I was just bad at my job.

Finding a new job once I’d (inevitably) been fired was never difficult, namely because of the abundance of mature gay men in positions of power in Denver, who would often hire me on sight.

This will probably come off as arrogant, but at 22 I was like catnip to old gay men. It came as a surprise to me, namely because there was virtually no demographic that found me attractive in Iowa. Skinny, pale, effeminate boys weren’t a hot commodity in the conservative farm culture of the midwest . . . but in this western city my appearance roused a frightening level of desire in homosexual seniors.

This wasn’t the case with young or middle aged gay men, or women of any age.

Just the silver foxes with their perfectly manicured hands and open-chested shirts, who would shower me with gifts, free dinners, drinks, drugs and trips to the movies. Naturally, I accepted all that they had to give me, feeling a true sense of value for the first time in my life. Though we were always an odd match, since both parties would be terribly nervous.

When Jane Fonda played a sex worker in Klute, she said the johns were “usually nervous, which is good because I’m not.” To be a good prostitute, you had to confidently direct the operation, and I was far too over my head to even carry on a conversation.

“You have such beautiful eyes,” my boss would tell me, stroking my face.

“Uh, thanks, but I didn’t make ‘em,” I’d respond, anxiously biting my cheek. “My parents had sex and made them, so you should really thank them.”

I’d be invited over for dinner, and my host would “accidentally” put some pornography on the TV. “Can we watch The Simpsons instead?” I’d say, completely oblivious to their strategy.

Like a boy-king, I’d been granted a supreme power I had no idea how to wield, and eventually my subjects became wise to this and revolted, stripping me of all amenities and firing me from jobs I had no right to in the first place.

It was after being given the boot from a luxurious downtown hotel—walking home in my bright-red, polyester bellboy uniform—that I encountered a john willing to do all the work for me.   


“Need a ride home?” he asked, leaning his head out the window of his taxi van.

It wasn’t a very long walk to my place, but Colfax was a bit spooky at 2am, and I’d honestly never ridden in a taxi before3, so I agreed and hopped in the van.

He was a large, sweaty man, needing every inch of his seat belt to cover him.

His crew cut hair was thin and gelled, his red face swollen with the signs of alcoholism I’d come to recognize from my restaurant coworkers. A tiny diamond stud flickered in one ear.

“What’s a cute kid like you doing walking home at this hour?” he asked.

We got to talking about all the jobs I’d had, and I told him about how people used to dine and dash on me and I’d be left paying for their dinner. “Often I’d work a ten hour shift and end up with less money than when I started,” I told him.

He sighed and shook his head, watching me through the rearview mirror with small, beady eyes—like tiny chocolate chips in a giant red cookie. “I know a better way for you to make some money,” he said with a squinty smile.


I’d learned from reading books like Hells Angels and Last Exit To Brooklyn, and watching movies like My Own Private Idaho and Basketball Diaries, to know that there were gay men out there who paid money to actually give pleasure to other men—and not ask anything in return.

This concept blew my mind, and I honestly couldn’t understand why Leonardo DiCaprio found it so upsetting. The Hells Angels biker who admitted to being on the receiving end of this deal explained with homophobic defensiveness that, while he enjoyed himself, he wasn’t gay if he charged more than ten dollars.

I didn’t want any orientation qualifiers or moral rationalizations.

I wanted to do something that would horrify teenage Josiah.

I wanted to knowingly and unrepentantly engage in the worst sin I could think of (that wouldn’t hurt anyone else), a theological middle finger toward a god I no longer believed in, and a Hell I was no longer afraid of.   

“Forty dollars,” the cab driver offered, explaining what he wanted to do.

His voice was much higher than when I first got in the taxi. He seemed shaky and out of breath, even though he was strapped into a seat. It amazed me that I could have such an impact on another human being.  

“A hundred,” I said, feeling inflated with self-confidence.

We’d been circling the Capitol Hill neighborhood for a while, but once the haggling was finished he pulled the car over and got into the backseat. He looked even larger up close, unable to sit comfortably despite the mini-van spaciousness. From his shorts sprung giant shiny legs, like angrily swollen sausages, purple veins snaking their way down dry skin. The more unattractive he appeared to me, the more aroused I became.

I wanted to be abused by someone gross.

I wanted it to be someone else’s fault.

I wanted to be interesting, like JT LeRoy.

I wanted to be anything but a good Christian boy from Iowa.  


As soon as he was finished, the taxi driver started to cry.

I was trying to clean the mess I’d made across my bellboy pants, when I suddenly noticed him turned away from me, hands over his face, his gelatinous body heaving with sobs. “What’s the matter?” I asked, and he flinched when my hand touched his shoulder. Hyperventilating with tiny gasps of air, like a child with a skinned knee, he hurriedly grabbed a wad of twenties out of his wallet, threw them at me, and told me to “get out.”

Of all the madness of the last 30 minutes, this felt the most familiar, and the most comforting.  

I opened the car door and had one foot on the ground when I stopped.

He turned and looked at me, the sun rising in the window behind him.

“I’m married,” he said, his voice nasally and weak. “To a woman. Kids, too.”

My heart collapsed, overwhelmed with empathy for this taxi driver and his guilt. Suddenly he wasn’t a disgusting, nefarious symbol of life in a big, sinful city, but a scared little boy who didn’t know what to do with himself.

I went back into the car and wrapped my arms around the man, feeling the weight of his sadness as he hugged me back, his pulsing sobs jolting both of us. I felt his fear, his self-loathing, his confusion. It was enormous and overwhelming, like grabbing a live electrical wire.

He was broken just like I was broken. Maybe even more.

He looked just like anyone else, but had a jungle of torment inside him.

Looking over his shoulder at the horizon of Denver, spiced with morning light, I wondered how many people out there looked as normal as pumpkin pie, but were hiding an ocean of sexual confusion and existential despair behind their American eyes.

Maybe all of them?  


A week later I was working in a Colfax diner, sitting at a barstool reading The New York Times while all my customers’ food grew cold in the pickup window.

There was a story in the paper titled “The Unmasking of JT LeRoy.”

It was an investigative piece revealing that twenty-four-year-old literary prodigy LeRoy was never a child prostitute in a Tennessee truck-stop, or a HIV pos heroin-addict in San Francisco. In fact, he never existed at all. The books and articles had been written by a middle-aged woman named Laura Albert, who hired her sister-in-law to put on a wig and sunglasses and play LeRoy during public appearances.

A lot of people were angry at Albert—namely young gay men in San Francisco who’d found inspiration in LeRoy’s story of overcoming abuse and illness to achieve stardom—but personally I felt nothing but gratitude. The experience of trying on LeRoy’s skin for a night had given me access to a world of wisdom I’d never been able to attempt otherwise. I thought of something Oscar Wilde once said, that “man is least himself when he talks in his own person. Give him a mask, and he will tell you the truth.”


I never returned to sex work after that night.

Instead I began writing humiliating personal stories about myself for money—a kind of prostitution that can be even more invasive than selling your body.

I would go on to befriend a few legitimate sex workers (whose stories go light-years beyond my friendly tickle with a cab driver), and would lose all the dark romanticism I’d held for the game when I was 22. “A lot of the time sex work is just work,” one of them told me, “Sometimes it’s fun, sometimes it’s not, but you gotta go to work like everyone else.”

Personally, I’ve never been a big fan of work.

And feeling the weight of that taxi driver’s sorrow while holding him in the backseat of his van, I realized what sex work entailed: Confidently, expertly, taking on the buried sexual neurosis of adult humans, who’ve spent decades channelling all their fears of death, failure and humiliation into their crotches, and carefully, empathetically removing it without showing the slightest flicker of distaste.

Which always seemed like way too much work for me.


1 Colloquially known to other pentecostals as “speaking in tongues”
2 I was too naive to realize that their generosity should be compensated with a purchase every now and then. Instead I dog-eared my place in their books and restocked their magazines upside down on the wrong shelves. Not because I was a punk-rock troublemaker, but because I was genuinely unaware that there were other people in this world to consider.
3 Taxis were a rare sight in my part of Iowa. Also, this was 2005, long before Uber or Lyft normalized paying strangers to drive you around.



Author of the psychological horror novel Carnality: Dancing on Red Lake, and regular contributor to VICE and The Guardian, Hesse aims to blend journalism and the arts within the pages of Suspect Press, making it both a reflection of our time and an innovative force of creativity.

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