Secrets of a Hipster Hooker

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

This article is from the September issue of Radar Magazine. For a risk-free issue, click here.

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(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.

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