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Secrets of a Hipster Hooker

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“Secrets of a Hipster Hooker”
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The author’s friends are stylish, well-educated, and professionally successful young women in New York City. They also turn tricks on the side for $2,000 an hour. One day she decided to follow in their footsteps
By Jessica Pilot

This article is from the September issue of Radar Magazine.
(Photo: Jessica Craig-Martin, shot on location at the Beatrice Inn)

I meet my madam for the first time at a vegan restaurant in New York’s East Village. Heather, a friend who has worked for her for more than a year, is the connection. She has told the madam that I am researching a story about the history of prostitution in New York City. And that is true—but my involvement in the subject matter seems to be getting more complicated by the day. I can feel myself getting drawn deeper and deeper into Heather’s world.

Is that a bad thing? I look at Heather, a 28-year-old who has a coveted job in fashion media, in her slinky black dress and silver Cartier bracelet. She looks happy, confident, prosperous. The madam does too. She is in her mid-thirties, tall and lanky. She’s wearing black leggings and motorcycle boots and has a vintage Gucci purse looped over her arm. If we met at a party I would peg her as an affluent Ivy League–educated scenester with a media job—and I’d be right. When she isn’t hooking up hot young professional women with lonely (or just horny) rich guys, she works as a consultant for a major news organization. And that MBA from a university whose very name makes peoples’ hearts beat a little bit faster no doubt comes in handy when trying to determine the maximum hourly market value of a romp in the sack.

I’m too nervous to eat, so I sip coffee while the madam tucks into a platter of mock pork. After a few bites, she asks why I’m so interested in writing about prostitution. My mind races. I could answer with references to anything from feminist theory to Belle de Jour. Or I could talk about the fascinating process of getting to know Heather and hearing the intimate details of her lucrative sidelight: selling sex to wealthy, powerful men. But I don’t have a coherent answer, and I let an awkward silence linger at the table. After a while the madam says cryptically, “You’ve got to be careful.”

I stand self-consciously before the madam in my underwear. “You’ve got a great ass, but your tits are too small, frankly,” she observes. Then she adds decisively, “I’m thinking $950 an hour”After dinner she invites me back to her apartment for a drink. Even though I don’t have an appetite, a drink sounds like a damn good idea. The madam lives alone near the restaurant in a rundown railroad apartment furnished with contemporary design pieces. There is an open foldout bed in the living room (friends often crash at her place, she explains). As she hands me a glass of wine, I notice her studying me.

“You know,” she says lightly, “I could totally send you out on calls. You’ve got such a unique look. I mean, you’re obviously no model, but there’s still something totally hot about you.” Before I can respond she says, “Take off your clothes.” Her tone is calm and authoritative. I must look painfully uncomfortable. “It’s not a big deal,” she coos, fixing me with a firm stare. I only now realize why Heather is afraid of her: She is one of those people you cannot say no to.

I pull off my sweater, step out of my jeans, and stand self-consciously before her in my underwear. “You’ve got a great ass, but your tits are too small, frankly,” she observes. “I mean, I’m sure you have no trouble getting dates, but the girls will tell you, men love breasts.” Then she adds decisively, “I’m thinking $950 an hour.” I feel a bit queasy but don’t protest. I am curious and honestly flattered that she is recruiting me. The force of her personality and the journalistic mystery of what will come next both act powerfully on my mind, pushing me forward.

I leave her apartment in a daze. I look at my reflection in the storefront windows and wonder, with a private smile, why she held back on that extra 50 bucks that would have pushed me into four figures.

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(Photo: Jessica Craig-Martin, shot on location at the Beatrice Inn)
Later that evening I meet my on-again, off-again boyfriend for dinner in a shitty Greek diner on the Upper West Side. Over a cup of black tea and a salad I tell him all about my meeting with the madam. I expect him to be freaked out, but to my surprise he loves the idea of me going out on calls. “Do it for your writing!” he says. “It’ll be great material!” He knows I enjoy taking risks and can handle myself well in tough situations. (Also, he’s a method actor and these days is in love with the idea of “material.”) Just as we’re settling the bill, my phone vibrates in my purse. It’s a text from the madam: “Do you have a slip on you?” I text back: “Slip?”

“Rubber” is the one-word response. I generally don’t carry them, but in my wallet I happen to have one of the NYC condoms the Department of Health distributes all over the city. When I text the madam back, I know—with a tingle running down my spine—that I am crossing both personal and journalistic boundaries. “I do,” I type. Before I know it I’m dashing home to put on some makeup for a two-hour appointment with one of her clients. For the rest of the evening my name will be Violetta.

I first met Heather—her working name—about a year ago. We were sitting at the same VIP table at a tony New York nightclub called 205 along with some pro hockey players and big-time artists. I had seen her at various parties and recognized her sleek, dark hair and honey-colored skin. I introduced myself, and it turned out we had a lot of friends in common. Heather moves in both fashion and media circles and refers to herself as a “quasi party girl.”

As luck would have it, I ran into her again the following night, at the Beatrice Inn, an ultra-exclusive A-list hangout in the West Village that until his death counted Heath Ledger as a regular. Heather and I started talking again, and after a few very expensive drinks she began confiding in me about her secret “freelance” work.

I was fascinated by everything she told me, and not just as an aspiring journalist. At 22 I had no immediate interest in getting married, and all my dates and hookups hadn’t amounted to much, except to make my life more stressful. In some weird way, what she did made a lot of sense. Heather, who grew up in New York in a wealthy family, seemed to appreciate my nonjudgmental interest in her sideline, and after a while she introduced me to her two “business partners.” She knew Olivia, another homegrown child of privilege, from their days as undergrads at a certain northeastern university. Olivia, who has brown hair and fine features that hint at her Tuscan ancestry, was a women’s studies major.

Heather’s other partner, a blonde with freckled ivory skin with whom she had some common friends, works under the name Kelly. After graduating from an Ivy League college in 2006, Kelly says she was thinking about going to grad school to become an English professor. She’s decided to put that aspiration on hold, though, while she rakes in the equivalent of an investment banker’s salary selling sex.

It was Olivia who planted the idea of high-end hooking in Heather’s and Kelly’s minds. After getting her bachelor’s degree in 2004, she decided to take a year off and live in Paris. Shortly after arriving there, Olivia recalls, she met a smart-looking young woman at a wine bar. “Mirabel was stunning in a very casual way,” she tells me. “No makeup. Blue eyes.”

When Olivia mentioned that she was looking for work and a place to live, Mirabel confided that she had money—and a bedroom—to spare as a result of an arrangement with a wealthy older man. Mirabel even joked about being a “kept woman.” Olivia moved in with her new friend a week later and soon realized that it was not just one man; Mirabel was also turning tricks with guys she met casually at bars, restaurants, and museums.

Olivia admits to being a bit taken by the “romance” she saw in her friend’s life. “It’s not like she was working for a brothel,” Olivia says. “She was content, but like me she had flair and enjoyed being around artistic and intellectual men.” Olivia soon began following her friend’s lead. “In a way it just seemed chivalrous when men would give us money. At the time I never thought of it as prostitution, but I guess I was in denial.”

It’s fitting that Olivia was in Europe when she first found herself exploring the option of selling sex. On the Continent, prostitution is legal or tolerated in most countries and generally carries far less social stigma than it does in the United States. But Olivia, Heather, Kelly, and their clients also seem to be at the forefront of an emerging shift in the nature of the industry here at home.

According to Columbia University sociologist Sudhir Venkatesh, who has spent more than a decade studying the field, high-end prostitutes (and there is an important distinction to be made here between those who choose prostitution and those who are forced into it) are emerging as a professional class more analogous to private yoga instructors or personal chefs than old-school streetwalkers. High-end sex workers tend to build long-term, mutually beneficial relationships with clients very much in line with legitimate service industries—despite the fact that the work is illegal and still occasionally dangerous.

There is an element of irony in the fact that the prostitution scandal that forced Eliot Spitzer to resign as governor of New York has given impetus to the debate in this country about whether our current laws against sex work make sense.

When Olivia returned to New York she told her college friend Heather about her Parisian exploits. Heather was less shocked than intrigued. Soon the discussions included Kelly, who, like the other two, was sexually uninhibited and not especially judgmental. After months of discussing and joking about Olivia’s experiences in Paris, the women moved to real-life hooking unexpectedly one weeknight in 2005, when they were drinking at Employees Only, a speakeasy-themed cocktail lounge in the West Village.

“These sleazy banker types came up to us and asked if they could join our table,” Heather recalls. At first she told them to get lost, but she relented after the men ordered a cheese plate and some nice wine. One of the guys took a seat next to Heather and, after some small talk, disclosed that he had just left his wife. “I’m looking to spend my money,” he said. He was fiddling with a cash clip stuffed with $100 bills. She accepted his business card and later Googled him. The man turned out to be a honcho at a major investment firm; the New York Times had profiled a charity he had started.

The next morning she called his office. “I got shaky when he answered,” she recalls, “but when he figured out it was me, it was better.” That night she went to his apartment in Trump Tower. “It was pretty straightforward. He offered me $3,000 to let him fuck me. I almost leaped on him.”

Olivia ended up sleeping with another member of the group, and Kelly decided she was game too. Soon the three women were hitting what Heather calls “douchebag spots” in the Meatpacking District—bars and clubs frequented by the kind of guy who’s happy to drop a few grand on bottle service. “A lot of rich men approached us, and we thought, Why the fuck not?” Heather says. The women expanded their client base with other, classier men they met at parties, and discreet referrals from existing customers. With new prospects—especially ones they met at bars—they were always careful to get a full name and an occupation and to do some research online. “If they are Googleable, that’s always a good sign,” Olivia explains. Beyond that, the women generally accept new clients only if the men “feel” right.

The trio’s rates start at $800 an hour on slow days and can range as high as $2,000 on busy weekends. With most dates averaging two to five hours—plus sleepovers once or twice a month—Heather and Olivia both estimate they made around $300,000 last year, tax-free. Kelly reports earning $500,000 in six months, in no small part because one client—a young artist who is receiving a lot of favorable attention—gave her a painting that she sold to an art collector friend for a six-figure sum. Olivia, who initially planned to quit after banking $25,000, says she is still in awe of how lucrative sex work can be.

All three women admit that they’ve worried about getting audited, but Olivia asked a client who was an accountant for advice, and he began doing their taxes. He has tried to keep the IRS at bay, advising the women to keep at least half of their earnings—either in cash or converted into gold bars—stashed away in safes.

Over time their networks of referrals have become somewhat self-reinforcing. These days Heather tends to book with more bankers and Wall Street types, Olivia with a lot of retired hipsters and club owners, and Kelly with men from the art world. During a typical week they each entertain at least three different clients—and sometimes as many as nine. “I don’t mind sleeping with two guys in a night,” Kelly says. “Just as long as the second client isn’t rough with me.”

Following that fateful evening at Employees Only, they worked as a collective for three years, sharing their connections and client lists and covering for one another in case of scheduling conflicts. Then, late last year, the madam came into the picture. She was an acquaintance of Heather’s from the media party circuit, and over the course of a few conversations the two had become friendly. The madam started asking questions about how Heather afforded her rather swank lifestyle on her modest salary. Heather was truthful with the woman, who in turn revealed her own sideline: She ran a boutique call-girl agency that bore some resemblance to the Emperor’s Club VIP that was taken down in the Spitzer scandal. The madam persuaded Heather, Olivia, and Kelly to freelance for her with promises of super-rich clients and more predictable demand for their services. In turn she received a 50 percent commission for every job
she booked.
Although the girls have yet to face violence while working, they are often asked to skirt the line between kink and humiliation. Last year Kelly met a new client, an aging punk rock pioneer who was staying at the London NYC hotel. Kelly was a fan of his music, but wasn’t aware of who he was until after their session. (He had booked under his real name; she knew him only by his stage name.) “He wanted me to force-feed him dog food,” she says disgustedly. “I mean, that was just too much for me.” After she declined, Kelly says, “We sat on his bed and he complained for an hour about how much money he was wasting and how easy it could have been for me to do it.”

Olivia recounts the time she was hired by a prominent hedge fund millionaire. “He took out all these large bills and placed them on the bed and said, ‘Don’t touch.’ I was instructed to take my clothes off, everything. No foreplay. So I got on the bed, and he just stood at the edge of the mattress and stared. He told me that all the money was going to be mine by the end of the night. They were all hundreds—maybe 50 of them. Once I got naked, he got on the bed and unzipped his pants and told me to start playing with myself. I kind of just laid there and faked an orgasm. He started jerking off, and he shot all over the money.” She smiles and hesitates for a moment before continuing.

“So then he grabs all of it in a bundle and throws it at me! I think he called me a dirty whore. Then he separated every bill and stuck them to my body. After he puts the last one across my mouth he looks at me and goes, ‘I told you it would be yours.’” As the client watched, Olivia peeled off the bills and put them in a plastic bag. When she got home she let the money soak in the kitchen sink overnight, blow-dried it, and used it to pay her landlady. “I couldn’t keep a straight face,” she recalls. But didn’t she find the experience upsetting? “You know, it was degrading, for sure. But so was cold-calling,” she says, referring to a job she briefly held as a fundraiser for a local political advocacy group.

When I ask Kelly a similar question, she fires back, “How many men have you slept with who have turned out to be assholes? Well, let’s say you could get reimbursed for all the time you spent with them. Would you?” But despite Kelly’s professed belief that dating is a lot of work that yields little emotional benefit, she has a long-term boyfriend—a musician who is usually home composing on the instrument she bought him last year with money she earned from two nights of work.

“Every artist needs a patron,” she laughs. Her boyfriend thinks she’s an event planner. “I feel guilty sometimes when I come home and he’s asleep and I’m still wired from my night, but I always climb into bed next to him and try to fall asleep. When he wakes up he likes to touch me and make love, and that’s when it hits me.” She knows she could stop working—she doesn’t really need the money anymore—but selling sex seems to have a grip on her. “Maybe it’s a power thing. Beyond the money I’m making, it has kind of become an obsession. It’s fast and fun. What we do may be illegal, but honestly I don’t even worry about that.”

Heather estimates that, all told, she has slept with about 20 men who weren’t clients and more than 70 who were. The relationships can sometimes be closer with men in the latter group, especially with customers she has seen regularly for two or three years. “Some of my clients think that we are in love. That’s fine, and I guess in my own way I love them, too,” she says. “These guys are just lonely. And I know it’s hard to believe some of the big names we’ve been with would ever get that way, but believe me, they are. You have to have some sympathy for a man who works so hard to be successful and has no true love in his life. He has to get it by the hour.”

She remembers meeting one of her clients, a CFO at a major investment firm, at his Park Avenue apartment building once. “I’m getting fucked and looking at a photograph in a solid gold frame of his young blonde wife and his children. You get over these things, though. Maybe his wife doesn’t sleep with him anymore. Maybe he just gets bored. But the bottom line is that it really doesn’t matter. It’s between us, and he knows that I can be trusted.”

Olivia puts it this way: “A man with a ring on his finger will pay me to fuck him like his wife did when they fell in love. They fantasize, and that’s healthy.” She continues, “You’ve got to be careful, though. I mean, some girls develop schizophrenia from this work. Remove yourself, but don’t fucking lose it. The reality is that there is a high price to pay, even in high-end hooking. I don’t have a problem sleeping with men in my personal life, but in the back of my mind I know that I will always think about how much easier it is to get compensated.”

For Heather the need to work is almost an addiction. One night last winter I met her for a drink. She hadn’t seen a client in two weeks and was a bit of a wreck. Her freelance night job, she admitted, helped her maintain her mental balance. Without it she starts feeling the compulsion to do something stupid and self-destructive (as she phrases it, “get into some shit”).

Kelly tells me more or less the same thing one day when we’re getting pedicures at a downtown spa. “You know what’s fucked up? When I don’t work I get really depressed,” she says. “And I know that is a sign that the work has an effect on me. I’ll be out with my boyfriend, and out of nowhere I begin calculating in my head how much money I could have made if I were on an appointment. But it’s not even the money that I miss; it’s a closeness that I’ve developed with some of my clients. We’re both hiding a secret about ourselves, and in a very bizarre way that’s totally hot.”

An hour after the news broke that Eliot Spitzer had been busted as an Emperor’s Club john, Heather called me to stress the importance of being discreet about everything she’d talked about. Over the course of that day a slew of influential clients (including hedge fund players, a prominent politician, and an exec at a major investment bank) had contacted her to request that she lose their numbers. Heather didn’t seem concerned. “Whatever. … They’ll all call me by next week to book.”

Not long afterward I meet Heather for a late dinner at Veselka, an all-night Ukrainian diner in the East Village. Her prediction was correct: In the week after Spitzer’s arrest the three women did just fine, collectively grossing $15,000. She spent five hours with a client at the London, Kelly was booked at the St. Regis for three, and Olivia had an hour-long session with a celebrity magician who is one of her regulars.

As we sip our drinks, Heather begins reflecting on the scandal that brought Spitzer down. The only thing she is sure of is that Ashley Dupré never said a word. “Working girls are the only professionals left that you can trust,” she says with a touch of bitterness. She is mulling over the idea of quitting her media job and opening a jewelry store. A longtime client gave her his ex-wife’s collection of gold Hermès pieces for her birthday last month, and that seems to have sparked a fascination. She also wants to travel around the world, to volunteer at Planned Parenthood, and to develop her own sex-positive program with other women in the industry. “I don’t want to encourage young women to become prostitutes,” she says. “But they should know that being objectified is not all that bad.” (Heather, Kelly, and Olivia are all dues-paying members of the International Sex Worker Foundation for Art, Culture, and Education.)

Kelly, I find out a few days later, has ramped down her work schedule and is taking some classes. “I don’t feel as though I am making a conscious decision about leaving the industry,” she says. “I just feel like I have the freedom to utilize my time for more than I have been doing. I have no regrets. I’m not damaged. I was never forced into doing this. It’s very easy, and that is why it is hard to fathom quitting entirely. It’s no big deal either way,” she says.

Just a few hours after meeting the madam at the vegan restaurant, I am walking through the lobby of Manhattan’s swanky Palace Hotel. I avoid making eye contact with anyone as I head for the elevator. On the ride up I open my handbag for the hundredth time to make sure I’ve got everything: mace, condoms (I bought more), and lip gloss. The mace is not likely to be required, and the madam would freak if she knew I had it, but I don’t care. I get out on the 11th floor, find the room, and knock, my heart beating furiously. A pudgy man with dark hair opens the door wearing a loose hotel bathrobe. “Violetta!” he says, extending his short, bushy arms and putting a hand on each side of my face. He looks at me for a moment, then gives me a kiss on both cheeks. “Come in, bella!”

I see that the covers are pulled back on the bed. A bottle of expensive champagne is nestled on the pillows. The man looks at me expectantly. I think about Kelly and try to imagine myself possessing her nerve and bravery. But it’s not there.

“I have to go,” I tell him. He looks confused—even a bit hurt. Hoping to change my mind, he hands me an envelope with his cash “gift” inside. It feels gloriously heavy. But I can’t take it. I’m not even sure why, but I know I have to leave. I quickly turn and walk out while the john sputters a few words of protest. I switch off my phone, get a cab, go home, and run a bath.

An hour later, when I turn my phone back on, it is flooded with text messages from the madam. Most are blank or contain only a question mark. The portly, hirsute gentleman in the Palace Hotel called her to complain. After a brief, tense conversation, I agree to go to her apartment to discuss things. She is livid and yells at me for a long time.

“You really shot yourself in the foot,” she says. “You realize that, don’t you? All the girls that work for me are normal. I don’t even know you and I can already tell something’s not right. Maybe it’s that you’re just not professional.”

Then she informs me that I owe her $2,000. I may have cost her more than that, really, because I probably blew her relationship with a great client, but she definitely wants the two grand. I don’t even argue. I give her the $300 in cash that I have on me and walk to an ATM, where I withdraw the maximum of $600. After more browbeating she makes me promise to pay her the rest the next day.

In the morning I roll out of bed, feeling dreadful, and go the nearest Chase branch. I ask the teller for $1,100 in twenties, in accordance with the madam’s instructions. Later I hand her the envelope, which she places in her freezer next to a box of Tofutti Cuties. Then she tells me to leave. I am not to contact her again. That will be for the best, I think.

This article is from the September issue of Radar Magazine.

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