Jeffery Self on Sex Work and His Memoir 'Self-Sabotage'

Of particular note, is Self’s reflections on his experience with sex work in his twenties — the same time he was beginning to make a name for himself in entertainment. In “Looking for Generous,” a chapter from Self-Sabotage shared exclusivelywith PAPER, Self unpacks the thrills, banalities and discomforts of the trade.

“Sex work obviously isn’t anything new, and if I had a nickel for every gay guy I know who sold some part of his body as a broke twentysomething, I’d have enough money to hire twenty sex workers of my own,” Self writes. “One wrinkle in the midst of my tenure in the oldest profession that made my experience unique, however, was that while I was a sex worker, I was also on television.”

An exploration of duality, survival and ambition, “Looking For Generous” is an honest, never self-serious account of the realities of getting by. Self chatted with PAPER about delving into his past, sex work in pop culture and advice he’d give to his younger self (no pun intended).

Self-Sabotage is your first book of personal nonfiction. What prompted you to delve into your past and tell these stories?

In 2006 I used to perform a solo show every Friday at midnight in this shitty theater in Hell’s Kitchen (it’s now a church) called “My Life on the Craig’s List” (a nod to Kathy Griffin’s show at the time) where I’d tell stories about all the anonymous sex I’d had on Craig’s List that week. That was my first foray into writing about my personal life, but I could never build the courage to evolve that type of thing into doing stand up comedy. I had a lot of regret and shame about that for a long time, but after years of failed TV pilots and a cavalcade of other rejections I thought it might feel nice to go back to those early roots. I was right, it does.

The excerpt you shared with PAPER, "Looking For Generous," is a really wry, honest reflection on sex work. Was this a time in your life you had thought a lot about prior to writing this book? What surprised you about what came up when you began to write this story?

I’ve always loved to tell my sex work stories at dinner parties, but had never felt compelled to put them into written words. Or maybe I just wasn’t ready to do so yet. Whatever it was, once I started doing so I went through all my journals from back then and I was so overwhelmed with pride in my following in the footsteps of so many before who have depended on sex work to get by. Those stories are the thing I’m proudest of in this book and in the whole decade of my twenties, as well.

The discourse surrounding sex work has changed a lot in recent years. What's the biggest change you've noticed in how sex work is talked about today vs. when this story took place?

Obviously it’s so cool that Anora celebrated sex work in such a loud way at the Oscar’s this year. I loved that brilliant movie, and I loved what Sean Baker and Mikey Madison said on national TV. But the reality is sex work is still illegal and sex workers have no healthcare or protections, and that is quite simply so fucking fucked. So I genuinely mean it when I said, “Yay for celebrities shouting out sex work on TV,” but also we should be fighting for sex workers’ rights, as well.

What's the biggest piece of advice you'd give to the version of yourself in "Looking For Generous"?

Floss.

Do you have a hope for what readers will take away from reading Self-Sabotage?

For young queer readers or any readers, the thing I hope they takeaway is to never let dumb social norms stand in the way of forming one’s own path. Also, not to harp on the previous, but floss.

"Looking For Generous"

He was a regular, he was kinda hot, and he was an investment banker. Or rather, in my mind he was an investment banker. I had no idea what this man did for a living, or what his name was for that matter, but he was always freshly home from work in an expensive-looking suit when I’d arrive. And investment banker was the main type of job I imagined for a person who had to wear a suit. Sure, there are plenty of jobs that require a person to wear a suit, but I would have been hard-pressed to name more than three (beyond funeral attendant, lawyer, and actor playing a lawyer on TV). At the time, my twenty-year-old self had a flimsy job history and little knowledge of working life besides, of course, the one that employed me at the time: having sex for money.

As this gay Gordon Gekko and I traded our assets of bodily fluids, I glanced over at the polished mid-century modern mahogany desk piled with important-looking documents and spotted a copy of that week’s TimeOut New York, opened to the LGBT section. There, smack-dab in the middle of the page amid listings of drag shows and circuit parties, was a large picture of me and my best friend advertising the show we would be performing at Joe’s Pub that night. The john, who really did look like a poor man’s Michael Douglas in his Wall Street era, noticed me staring at it... but neither of us acknowledged it. Besides the embarrassment for us both, we were busy: the stock market was open, and he was IP-ing my O.

Between the ages of twenty and twenty-three, I supported myself by hooking up with cash-wielding strangers I met on Craigslist all over New York City and, on a few particularly desperate and Mann Act–defying days of the month, New Jersey. Sex work obviously isn’t anything new, and if I had a nickel for every gay guy I know who sold some part of his body as a broke twentysomething, I’d have enough money to hire twenty sex workers of my own. One wrinkle in the midst of my tenure in the oldest profession that made my experience unique, however, was that while I was a sex worker, I was also on television.

“On television” is a generous term, but technically it was true. It’s not like I was starring on Murphy Brown circa 1991 (God, how I wish). Instead I was on the wildly unpopular gay cable network called Logo doing our show Jeffery and Cole Casserole, for which we were being paid historically little.

The original idea for my new day job came to me when I was on the train home from a trip to Fire Island. Not only had I had a Herculean amount of anonymous sex, including a memorable experience atop the steering wheel of one of those giant Bobcat machines someone had left on the beach, but I’d spent the remaining crumbs of my checking account on an overpriced drink (or twelve) that I was too young to have legally ordered in the first place. I was sitting in the train car watching Long Island pass by, getting closer and closer to the city I couldn’t afford to be living in. While I should have been wondering how the hell I’d pay my rent the following week, I was as usual ignoring the problem and flipping through the pages of the beach read I’d never once opened during my trip. The train was crammed with the usual crowd of brain-fried and bloodshot-eyed gay men returning home like soldiers from a Speedo-clad war of muscles and narcotics. There happened to be two boys around my age across the aisle from me who were cute enough for me to be eavesdropping on their conversation.

One of them was telling the other about how he’d been making money by posting ads on Craigslist’s “Men Seeking Men” section and indicating that he was “looking for generous.” Apparently, there were all these rich men on Craigslist who would click on the profile of a “generous seeker” and pay them to hook up. Seeing as the number of online hookups I was having at the time could have been submitted to Guinness World Records, I figured, Why not starting charging for admission? The boy telling the story was cute but not much cuter than I was, plus in comparison to my twenty-year-old self he was basically ancient, by which I mean twenty-six at most.

Not even two hours after the train had pulled into Penn Station, I had rushed home, posted an ad, gone to an apartment on the Upper West Side, and was one hundred dollars closer to paying that month’s rent.

My first time was with a bald man in his midforties who told me he was a news producer for a popular cable network. He seemed exhausted and like he had just been smoking crystal meth. Both things were undoubtedly true. The whole thing must have lasted no more than half an hour, as quick and clinical as getting a flu shot, with none of the side effects. That is... if your flu shot was being administered by a soporific man in ratty-looking gym shorts and flip-flops with hard-core porn playing on a TV in the corner. We lay down on his unmade bed with sheets reeking of the unslept and started to simply jerk off next to each other. His phone kept ringing and beeping with text notifications the whole time before he eventually got up, stormed across the room, shut off his phone, slammed it down in frustration, and shouted, “I fucking hate election years!”

Mere minutes later I finished, and the mere visual of my doing so was enough for him to follow suit before he sent me on my way without my ever once having to so much as touch him. Nothing about that first experience was difficult. It didn’t feel seedy or immoral or wrong. In fact, it was a little disappointing. I’d psyched myself up into thinking what I was doing was so punk, so rock-and-roll, so shocking that by the time I finished, I would be such a new, more badass version of myself that people wouldn’t even recognize me. However, as I walked back home past Lincoln Center, my dried cum gluing my American Apparel V-neck T-shirt to my stomach, I thought, Is that all there is?

The eventual answer: no, Peggy Lee, it isn’t.

I dove headfirst into this new day job for which I suspected I might actually be skilled. Nearly everyone who hired me was nice enough and as respectful as you can be when you’re naked and erect with a stranger. There was a friendly man who owned a dance shoe store in a sleepy part of Brooklyn, who would hire me to come over after closing. The store lights would be out, and the metal security gate would be pulled down with just enough room for me to crawl underneath it. Once inside the cramped store, surrounded by leotards and Capezio tap shoes, we would hook up on one of those short, old-fashioned stools with the built-in device to measure your foot while I stared at a poster of a male ballerina jetéing at the bar, the paper yellowing with age but the man’s face as handsome as the day it was taped to the water-stained wall.

There was a doctor who smelled distinctly like the onions at Subway who only wanted to blindfold me and give me a blow job. He lived in an upscale high rise, and one time I saw a very well-known movie star in the lobby getting his mail, so every time I went over I would fantasize that I was actually there to meet the movie star instead. I still can’t watch that actor’s movies without thinking about the onions at Subway.

Another man lived in a dollhouse-size West Village studio containing more potted plants than I have ever seen in my life. It was like being paid to have sex with Audrey II from Little Shop of Horrors, endlessly being poked and prodded by vines and branches in one or both of our orifices.

Excerpted from SELF-SABOTAGE: And Other Ways I've Spent My Time. Reprinted with the permission of the publisher, HarperOne, an imprint of HarperCollins. Copyrighted © 2025 by Jeffery Self.

Photography: Chad Benson