I’m making the rounds at a small gathering of urban literary types in a bougie brownstone in Brooklyn, New York. It’s the holiday party for the publication we all work for, some as photographers, others as editors. I’m one of the writers, and currently on my third glass of the social media guy’s homemade margarita concoction. It’s really good, possibly the best margarita I’ve ever tasted. A sudden urge to commend the social media guy on his cocktail-making skills propels me over to where he’s standing with another man in front of the television streaming a fireplace video.
As I join them mid-conversation, one guy is telling the other that when he was in college, his roommate suggested that he try sex work to make some extra cash.
“Why sex work?” the other guy asks. “Do you have a big dick?”
“I don’t know. What’s big?”
“Are you bigger than six inches? I’m sensing a wide girth.”
“I think I’m eight inches.”
“You fucking motherfucker. Okay, continue.”
“There’s not much else to say. I thought about it, but never went through with it, probably because my roommate was pressuring me so much.”
“I’ve done that before,” I blurt out.
They look at me.
“Done what? Suggested someone do sex work?” the first guy asks.
I shake my head.
“Been with a sex worker?” the other guy asks.
I shake my head again.
“I’ve done sex work,” I say, taking another sip of my margarita. Top that! I think for a fleeting second. Followed by Holy shit. Before this moment, I had told no one this information except my therapist, and that was many years ago. I’m not quite sure why I just blurted it out now, except that I feel comfortable and tipsy and confident, like I have nothing to hide. But I think the guys might have been joking around, because they’re looking at me with that look that writers get when they hear something surprising. I’m a 45-year-old single woman, attractive in a big girl kind of way, and I write science and health articles. No one would ever guess that I briefly sold sex for money.
The guys pepper me with rapid-fire questions: “When? How did you get into it? How much did you charge? Did you like it? Were you scared?” I answer them one by one – except how much I charged. My instinct is that disclosing this information will cloud their already mind-blown status, and it’s really none of their business. They concede this point, and convince me to share my story with our boss, the chief editor of the publication we all work for. “How do you feel about it now?” he asks. “I’m not ashamed of it,” I shrug. “I used to be, but I’m not anymore.”
The next morning, I wake up with a jolt. What the fuck did I say at the holiday party?
I imagine the guys sitting around the conference table at the weekly staff meeting laughing about this exact moment – me, lying in bed, hung-over and mortified.
For the rest of the day, insecure “thought bubbles” plague my every move. Does everyone in the office know now? Will they tease me about this forever? Are they imagining me in bed? Will they try to get in my pants? Will they offer to pay me? Will they stop wanting to work with me? Will I stop getting invited to the holiday party?
I mentally swat these thoughts away with repeated mantras of self-assurance. Some people might judge me, but not these guys. Anyway, a two-week sex work gig isn’t that big of a deal. I mean, who cares?
But it was a big deal at the time, and it took me years to admit it, even to my therapist. The fact that I’m telling anyone about it now is a testament to everything I’ve lived through since.
* * *
It happened over ten years ago.
I was living in Los Angeles, in between temp jobs and broke. A friend offered to let me crash with her in New York City for as long as I needed to get back on my feet. I couldn’t afford a plane ticket so I took a Greyhound bus for $99 one way from LA to NYC. I arrived at the Port Authority Bus Terminal three days later and headed straight for my friend’s house in Brooklyn.
Over the next few days, I called temp agencies and perused Help Wanted ads in the newspaper and on craigslist. As I searched the jobs and gigs sections on craigslist, I noticed the personals section, divided up into “strictly platonic, men seeking men, women seeking women, men seeking women…” and so on. Out of curiosity, I clicked on a section called “casual encounters.”
The posts in casual encounters were all about sex. Most of them mentioned money and a combination of phrases that I didn’t understand like BBW, Dom, wfm, sub, top and 420. After clicking on a few posts, I quickly figured out the lingo. BBW means big beautiful woman. BBBW means big beautiful black woman. Dom means dominant. Wfm means woman for man. Sub means submissive. Top means likes to be on top. 420 means smokes marijuana. I was surprised by how frank the posts were. People were very specific about what they were into.
Over the next few days, I sat in several different Brooklyn cafes with my laptop, mostly staring out the window. None of the temp agencies had responded yet, and I was starting to feel tightness in my chest thinking about all the upcoming bills that I had no money to pay. My mind kept drifting back to the craigslist posts.
Could I have sex with a stranger for money?
I mentally listed all the reasons why this was the worst idea in the world. I could get arrested, killed, infected, raped, robbed and/or recognized (because you never know). Then I tried to think of why this wasn’t the worst idea in the world. The only thing I could come up with was I need money. And getting paid for sex seemed like a quick and easy way to get it. Well, quick. I wasn’t sure how easy it would be.
I was in my mid-30s and had experienced several sexual encounters, including deliberate one-night stands, and threesomes that sort of just… happened. Sex had a way of finding me, and I had a way of finding it. I liked sex. It satisfied something inside me that was more than physical, though the satisfaction was usually fleeting. I was good at sex, and I was a bit of a thrill-seeker. But I’d never been paid for it. Money made it a job. I wasn’t sure how that would feel, or if I could go through with it.
I decided to post an ad and see what happened. I didn’t tell anyone, partly because I was embarrassed to be this broke, also because I knew friends would tell me, “Don’t do it.” Whatever happened, it would be my decision and my responsibility. Anyway, there was no guarantee I would get a response to my ad.
Hi, I’m a college student trying to make some extra money. Would you like to hang out? I am 5’3”, voluptuous, with brown hair and hazel eyes. I’m drug free, disease free, 420 friendly and open-minded. Hope to hear from you. xxx Cindy.
I figured being a college student sounded more sympathetic and younger than being an unemployed 35-year old woman. Cindy was the name of a girl I disliked in the third grade, and the Brady Bunch kid.
Within 24 hours, a few men did respond. I wrote back to the one who wrote in complete sentences. He wanted to know if I would come over the next afternoon, what I charged, and if I could send a pic. I responded, yes I could come over the next afternoon, my rate was $150/hour (neither as low or as high as what others were charging), and no I wouldn’t send a picture. That was evidence that could be used against me one day.
The following afternoon, a weekday, I was in the back of a taxicab on my way to Client #1. Totally. Freaking. Out.
I kept the window cracked even though it was cold outside, because I needed to breathe fresh air. I had done some crazy shit in my life, but never anything like this. The thought that I might die wasn’t as horrifying as the thought that I might die doing sex work. I had a Master’s degree, for chrissake. I had two passports. What the hell was I doing? I kept reminding myself that I was there because I needed money, and I’d sworn I wouldn’t ask anyone for help this time. I was going to take care of things myself. It was time to man the fuck up, or go home.
The taxi pulled up to a house somewhere in Brooklyn that felt very far away from my friend’s house. I paid the driver, walked up to the front door of a row house and pushed the doorbell. The taxi drove away behind me as the door opened.
Client #1 was an Asian man in his mid-20s, an inch or two shorter than me and with a bit of a belly. He wasn’t my type, but he had a nice voice, and a nice smile. I was pretty sure he wasn’t an ax murderer.
As we walked through the house, he pointed to the cash on the plastic-covered dining room table, and chit-chatted about this and that. I don’t remember anything he said because I was practically having an out-of-body experience. I simply followed his voice until we were in his bedroom, and he closed the door.
The next thing he did was put some Elvis music on. Then he put his arms around my waist and started singing along softly with Elvis. I was so nervous that I found it difficult to focus on anything, so I tried to focus on the music. Was Elvis the perfect music to die to? Or could nothing bad happen to a person while listening to Elvis?
After a couple of songs, he took my hand and swerved me a few inches around to the bed. We got on top of it fully dressed. I noticed his erection through his sweatpants. Did he know that I could see it? Was I supposed to do something now?
The song ended. He lifted my chin and kissed me. I closed my eyes and kissed him back, a little more hesitant than usual (besides the obvious, I was also stone-cold sober, and it was the middle of the day). When he started unbuttoning my jeans, I tensed a little, and he kissed me harder, practically sticking his tongue down my throat. It melted me. Let him do whatever he wants, I thought. Surrender to this moment. Make him feel loved.
From then on, everything flowed in a normal fashion. Once I realized that he was a nice guy just trying to get a little, I wasn’t afraid anymore. I almost felt sorry for him. Where else was he getting laid? He was so appreciative that it was almost endearing. When he came, the look on his face was one of pure gratitude. I was happy for him, and felt a tinge of pride. He was getting a good deal. My pussy was a goldmine.
Afterwards, he let me dress in private. When I came out of the bedroom, he offered me a glass of water.
“Do you want me to call you a cab? Or do you want to take the subway?” he asked to my back as I pocketed the cash on the dining room table.
“I don’t know,” I said. I just wanted to get the fuck out of there.
“Well, what train do you need?”
“The A or the F,” I answered.
“Cool. The A is just around the corner. I’ll walk you.”
In the ten-minute walk to the subway station, I learned that he was an aspiring actor who worked a day job and lived with his parents in order to save up enough money to get to Los Angeles. He had called out sick that day because he needed some “alone time.”
When I told him that I lived in Los Angeles and worked in Hollywood, he was like, “No way. Maybe you know my friend _____, light-skinned dude, gap in his teeth. He’s also an actor.”
“_________? Yeah, I know him. We worked on (so and so’s film) together. That’s crazy.”
I suddenly felt nauseous. What were the fucking chances?
“Small world, huh?” he said.
“Yeah.” Too fucking small.
“I won’t mention anything about, you know, this, next time I talk to him.”
“Thanks,” I said. There was nothing I could do but hope to god that he meant it and wouldn’t be on the phone with his buddy as soon he got back to the house.
We got to the subway station.
“I had a great time, Cindy, thank you,” he said.
For a moment, I didn’t understand why he called me Cindy. Then I remembered.
“You’re welcome,” I said, and walked down into the subway station.
I sat on the subway feeling flushed and disgusted, but also relieved. I had conquered my fear and survived. I had enough cash in my purse to pay a couple of bills. What I had to do to get that cash was awkward and weird, but pretty basic. Now that I’d done it once, I knew I could do it again. It was surreal riding that subway back to my friend’s house. I alternated between feeling like everyone could tell that I’d just slept with someone for money, and feeling giddy with my secret.
* * *
Over the course of the next two weeks, I had five more encounters. The second was a white-haired professor who taught at New York University. He lived in Greenwich Village and hired me because his regular girl was unavailable. The third was a man in his 30s who lived in Park Slope. His wife was eight months pregnant and out of the house for some reason. The fourth was another man in his 30s and very handsome. He lived around Union Square, and wouldn’t look me in the face the whole time I was with him.
The fifth encounter was in Bed-Stuy and the only one that happened at night. I didn’t realize there were two men at the apartment until I arrived, and I almost backed out. They agreed to hang out with me individually while the other stayed in the hallway, but I was still nervous. Being with two guys, one after the other, brought back memories of a similar situation when I was sixteen. The night I lost my virginity to a seventeen-year old boy that I liked, his best friend showed up in the middle of everything. Even at that young age, I instinctively knew that they had coordinated this “coincidence.” I felt betrayed, but I didn’t leave.
I didn’t leave the apartment in Bed-Stuy either. But afterwards, I swore I wouldn’t do another encounter. They were too risky, and they weren’t good for me emotionally. I could feel myself being sucked into this world, at the same time as I felt a growing sense of shame. I kept wondering, “Why am I doing this? What’s wrong with me?”
The friend that I was staying with had also started to become suspicious.
“Did you get a job?” she asked me one day.
“Not yet,” I answered, my stomach getting tight.
“So, where are you getting cash from?”
“A check from one of my old temp jobs just cleared,” I answered, avoiding her eyes.
“Are you going on interviews? Where are you going when you go out?” she continued.
“I’m just… going… to cafes,” I stammered.
“Seems weird that you’re going to cafes when you don’t have any money,” she said. “Are you sure you’re okay?”
“I’m fine.” I flashed a quick smile, and ended the conversation by heading into the bathroom.
* * *
A few days later, the NYU professor sent me an email asking me to come back.
Of all the encounters, he had been the one I disliked the least. There was something sexy about him, and I liked his apartment – it smelled faintly of marijuana and was lined with artwork, sculpture and books on philosophy, history and poetry. He kept the heat up so high that it was warm even when we were naked. And what he wanted was pretty straightforward – a blowjob, with the added step of shoving two latex-gloved fingers covered in Vaseline up his ass right before his orgasm. I charged him more than the others.
The second time I saw him, after I gave him the blowjob, he asked if I would be willing to let him pleasure me. I could have left at that point, but I was intrigued. He told me to lie down on his bed, and slipped a sleeping mask over my eyes. When I couldn’t see, all my senses were heightened – sound, smell, touch, taste. I felt scared for a moment, but not scared enough to get up and leave. Soon I heard the buzzing sound of a vibrator, which the professor used very slowly and rather expertly to bring me to orgasm.
When I left the professor’s brownstone, it was rush hour. People bustled about. Cars honked. I walked down the street in a daze, again feeling that flushed, “I’ve got a secret” sensation, but also sad. Something about doing it twice with the same client felt different. Before this I could justify these encounters as a fleeting phase, an experiment, something I was just doing for now, but not what I did. Being with the professor again made it more real. I could picture myself seeing him every week, and getting accustomed to, if not, liking it. There was a part of me that wanted to know the professor better. The fact that I was in a city of millions and couldn’t talk to a single person about this, made me feel terribly alone. In that moment, I had no idea what I was doing, where I was going, or what would become of me.
I sat on a bench in a nearby park and burst into tears. I vowed to get my life together and never ever let myself get into this situation again. That was the last time I had sex for money.
* * *
It took me years to stop thinking about this two-week period, and to stop feeling guilty about it. The burden of keeping my secret haunted me especially when, two years later, I started dating the man who would eventually become my husband. At first, I was afraid that he might judge me for being good in bed. Most men I’d known appreciated this, but would only want to sleep with me, not date me. When I realized this man I was falling in love with didn’t judge me or anyone for their sexuality, sexual tastes or past, I felt like I’d finally met my soul mate.
But there were moments when I’d flash back to one of those encounters, especially the professor. The man I loved also happened to like blindfolding me, and sometimes used restraints like handcuffs. We would role-play and pretend to be other people. One time I pretended to be a prostitute who’d been sent to him as a gift from a mysterious friend.
I often wondered if it was wrong in some way to not disclose my secret. Would he still love me if he knew? In the beginning, I was too afraid to find out so I never mentioned it. Later in our relationship, when he fell ill, this dilemma became a moot point. There were a million other matters that were more important, and I knew that he loved me no matter what. My secret had no relevance on our life together, and I thought it would just make him sad. It still weighed heavy on my heart because it was something I held back from him.
After he died, I experienced this overwhelming sense of forgiveness, as if he had either known all along, or he knew everything about me now, and all he felt was compassion and love towards me. With the stress of illness and caregiving no longer a factor, I had the time and space to fully appreciate just how much I had lost – a truly good man, whom I could totally trust, who accepted me for all that I was, who believed in me as an artist, and respected me as a woman.
It was beyond devastating. Yet, as I rose from the ashes of my beloved and the intense pain of losing him, something fortified deep inside me. He was permanently a part of me, and all that love, faith, trust, acceptance and respect now pulsed in my veins. The fact that loving and losing him healed something within me is one of the cruel ironies of life.
Since his death, I have forged a new career as a writer and live a fairly simple but content life as a single woman. I no longer feel shame about what I did in the past, nor do I judge myself or anyone else for doing sex work. I do, however, feel protective of my self and my livelihood. Because I work with corporations and clients that might not be as understanding, I’ve chosen not to use my real name here. My goal is to get my career to the point where I can one day write something like this and use my real name. Even without revealing my identity, writing and publishing this essay is as scary and painful as it is cathartic and empowering.
When I see my younger self, sitting on that park bench in New York City crying, I want to reach out and hug her and tell her that she’s not a bad person, she’s not a slut, there’s nothing wrong with her, and she’s worth so much more than any of these men could imagine. I want to tell her that in the years to come she will meet a good man who will love and accept her for all that she is. I won’t tell her that she’ll lose this man too soon and be a young widow, but I will tell her that in a little over ten years’ time, she’ll be working as a professional writer, making money with her true talent, her ability to write.
Most of all, I want to tell her that, despite the ups and downs that lie ahead, she will eventually love and forgive herself in a way that she never thought possible.
* * *
Leni Loving (a pen name) is a writer living in New York.
Ivy Bradley is a painter whose work explores the sexuality & sexualization of women and the fetishization of the female body. You can find her (NSFW) paintings at www.ivybradley.com.