Now Servicing Westchester

Prostitution! For some, the word evokes images of seedy, scantily clad women trolling around street corners looking for their next John. But, if that’s how you think prostitutes operate in Westchester and neighboring Fairfield County, boy, are you about to be surprised. Two local escorts come clean about what’s really going on between the local sheets.

It’s not hard to find sex for sale in Westchester. At least it didn’t take me long to find people who offer it. You can try it yourself: log on to,,, or If the number of listings for women who are looking to make a buck with their bodies doesn’t overwhelm you—on alone, there were 15 women available in the Westchester/Fairfield area and many more in New York City—the number of reviews from guys willing to indulge them will. Multiple escorts who serve Westchester and Fairfield had more than 50 reviews. And if you’re confused by what you read, it’s not surprising. Escort sites have a language all their own. “GFE,” for example, means “girlfriend experience,” which means that an escort is willing to do anything a “good” girlfriend would do. But that’s just the most commonly used initials; most of the others cannot be described here.

And for those “newbies” out there, fear not. offers a “Client and Escort Guide” to first-timers with advice such as:
Money exchanged in legal adult personal services is only for time and discreet companionship. It may also be in exchange for certain services such as exotic private dance, modeling, role-playing, or sensual massage.

It gets better…
But, of course, the male expectation/fantasy goes beyond merely meeting with her for an hour. We “expect” a sexual experience, which for most of us includes fondling and embracing, followed by… If this does happen (and there is no guarantee that it will happen given the above parameters), then whatever happens is purely a matter of personal choice and personal preference between two or more consenting adults of a legal age and is not contracted for nor is it requested to be contracted for or compensated for in any manner.

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To learn what I could about upscale prostitution in Westchester, I sent emails to nine escorts servicing men in our county. It wasn’t difficult to do. Many escorts list their email addresses on sex websites, or even create their own promotional sites. (“No sex,” they all proclaim of course.) I received three email responses. The first was a disappointment:

I am a fan of Westchester Magazine and also of your lively and always interesting writing and research for the magazine. I am very flattered to be considered as a source for your article. Nonetheless, I must decline your kind invitation. I and my family have too much at stake. And, although I am confident that you would do everything in your power to protect my privacy and anonymity, I am not prepared to take a risk of any kind…

In another world, at another time, I would have loved to help you. I firmly believe that escorting should be an open and accepted way of life, but I am not prepared to be a pioneer in making it happen.
Then came an email from Jennifer (not her real name), asking if there was a fee for this “fictitious story” and how I planned to protect her anonymity. I wrote back explaining that we don’t pay for editorial content but that I would do everything I could to keep her identity a secret. My phone rang. “Hello,” I said—and then heard a voice that sounded like it belonged to someone pleasuring herself: raspy and deep, with heavy breathing attached to the end of every word. I had found my first prostitute!

Section 230.00 of the New York State Penal Law states that “a person is guilty of prostitution when such person engages or agrees or offers to engage in sexual conduct with another person in return for a fee.” Prostitution is a class B misdemeanor punishable by up to three months in jail. Statistics on prostitution in Westchester County are somewhat scattered, a problem District Attorney Janet DiFiore is working hard to improve, her staff says. However, what is known is that, in 2006, there were 192 cases of prostitution brought in the county (according to the FBI, there were 84,891 in the country in 2005 and 79,673 in 2006). This includes all charges brought against prostitutes, Johns, and pimps. According to the New York State Division of Criminal Justice Services, there were 181 arrests for prostitution in Westchester County in 2006 (some arrests led to multiple cases brought; hence, the higher number of cases than arrests): 72 were for prostitution, 83 for patronizing a prostitute, 25 for promoting prostitution (essentially “pimping,” a more serious crime than prostitution itself), zero for permitting prostitution (knowledge that one’s premises are being used for prostitution and failing to halt or abate such use), and one for loitering for prostitution (loitering or remaining in a public place for the purpose of engaging or agreeing to or offering to engage in prostitution). In total, Westchester arrests made up only 2.8 percent of all prostitution arrests in the state. As a point of reference, New York City police made a whopping 75 percent of the arrests in the state.

However, two recent prostitution-related cases grabbed headlines in the county. In February, 2007, dominatrix Sandra Chemero was arrested for running a prostitution ring out of her home in Bedford, which, ironically, she rented from a local yeshiva. Last September, six people were arrested for involvement in running a den of prostitution near Iona College in New Rochelle. As of press time, their charges have been dropped to misdemeanors, and five of them are awaiting trial.

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Jennifer is terrified of being caught. But it’s not just the penalties for prostitution that scare her—it’s the fear of the IRS penalizing her for all the unreported money she has made while working as a prostitute. In fact, she recently hired an attorney to have on call should anything happen. But despite her fears, she was willing to talk about her profession.

Jennifer, who wouldn’t reveal her age (except to say she was “older,” and that many young men love that) describes herself as “soft and curvy with a squishy tushy…
resembling either Anne Margaret or Stephanie Powers.” She had been married for 30 years, she says, and has three kids. She says she never once cheated on her husband, a skilled professional who earned a large income. But she did grow bored. “My husband had little room for emotion,” she says. “I needed emotion, needed intimacy, and I thought there was more intimacy in the world to be had.” So she left.

The divorce did not sit well with her husband or her sons, who, she admits, no longer speak to her. But Jennifer, who says she had worked as a corporate executive throughout her marriage, figured that with her salary and her alimony, she could continue to live well. She soon found out she was wrong. “I was accustomed to a certain lifestyle while married and I needed to find a way to continue the way I lived.” She was also lonely. So she tried online dating. “I found no quality men,” she says. “They all think they can buy you dinner and then just sleep with you.”

Three years ago, while living in Manhattan, Jennifer had what she remembers as a “serendipitous” conversation with the doorman of her building. “As these old men walked out of the building with young women on their arms, he would tell me ‘escort, escort, escort.’ I thought, there might be a calling for a chubby Jewish girl with big breasts.” She also thought that if the right guy came around, she could turn it into something more serious—maybe another husband. Intrigued, she put up a listing online. “I got emails—like a billion,” she says, “so I took the first guy who wanted an appointment. I thought we’d just go out to dinner, that I would be just mature eye candy. But as soon as he came over, he started kissing me. He put three hundred dollars on the nightstand and said, ‘Can we —-?’ I paused, awkwardly, and said ‘I’ll have to think about it.’ He went running out the door.” Though surprised, Jennifer was also excited. So she gave it another shot.

Her client list grew, as did her knowledge of what made men happy. “I give men all things their wives should be giving them,” she says. And that is? “Intimacy. I care about these men,” she says, noting that much of what she does is listen. Many guys want to talk about their wives and their problems at home, she says, adding that she serves as a therapist of sorts much of the time. As for specifics, Jennifer explains that “an evening with me starts with smoked salmon, foie gras, expensive cheese, shrimp, sips from a four-hundred-dollar bottle of Scotch, and Champagne. “And I play Rod Stewart. Men tell me that they’ll hear him playing over the speakers in an elevator and they’ll smile and think of me.” Jennifer says she spends $200 on each client, and her investment in her clients has paid off: one of the sites that ranks escorts ranked her the No. 1 escort in the Northeast. Small wonder, then, that she charges “many times” the three-hundred dollar going rate. “I only work twice a week. And I never mention money. The men leave their donations in a box of chocolates or in an envelope on their way out. If they forget, I know they’re good for it.”

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 According to New Rochelle police lieutenant Chris Hearle, who last year helped bring down the prostitution ring running out of the two-story ranch house on North Street in the county’s second biggest city, “Jennifer’s stories ring true. Men who would not pick up street walkers can now go online and make outcalls” for hookers. Indeed, the NRPD actively sets up sting operations in which police officers venture onto sites such as craigslist posing as Johns to lure prostitutes into New Rochelle hotels. Lieutenant Hearle emphasizes that because of the Internet, a new, “less bold” breed of men now has access to sex-for-hire. And whether they are on the street or online, the men he and his police force arrest span the gamut from poor to rich.

Jennifer, who says she has a graduate degree, caters exclusively to the richer side of the John spectrum, noting “most of the men I see are from this area, and most of them are rich and powerful.” Jennifer knows what it means to be rich and powerful: she travels in elite social circles and associates, she says, with some of the most well-known socialites in the county (names, of course, though shockingly well known, were off the record). “I see hedge-fund managers, CEOs, ministers, police, and even police chiefs. Fifty percent of the men I see are in the paper every day.”

Recently, she says, a 60-year-old executive drove from Boston to her apartment. He said that he had been married for 40 years and had never once cheated on his wife. But lately, he couldn’t get aroused. That was not a problem during his time with Jennifer. “I was happy for him,” she says. “It meant nothing was physically wrong.” His marriage—that’s another story.

“Most of my guests are married and sexually repressed. They cheat because there is stress in their marriage.” Or serious issues. For example, the wife of one of her clients was suffering with cancer. Says Jennifer: “We live too long to be monogamous.”

“Wouldn’t it hurt, though, if someone you loved went to a prostitute?” I asked. Jennifer paused. “Well, I guess it always hurts when someone cheats, but this would hurt far less. I could get over it. I would feel bad for the wives if they found out, but I think the wives would feel worse if their husbands were having a love affair. At least here they don’t get emotionally involved like when they are having affairs. Many of these guys are doing the best they can under the circumstances. They really think they are not cheating.” She adds, “Once money passes between us, it doesn’t feel so bad.”

“And other women can get jealous too,” she says. “Hookers don’t like it when their men see other hookers.”

Jennifer admits that she has to “lie all the time. I can’t trust other ladies. I can’t talk to my friends. No one knows. It makes me very lonely.” She has had moments when she thought her life was about to crumble. One of her guests showed up one night, whipped out a badge, and told her she was under arrest. “He turned out to be a U.S. Marshall,” she recalls. Fortunately for Jennifer, he was just kidding.
“I make men feel good, and that shouldn’t be illegal.”

Michelle, the third respondent to my mass email, was more than willing to talk to me. Indeed, she sent me her phone number without even checking to see who I was (if only I had so much luck in the bars of White Plains). Michelle differed from Jennifer in one major way: she is married—for three years—and has one daughter.

She has a corporate job (she won’t divulge more about her day job) and is planning to retire from the escorting business in a year. Having started a little under a year ago while browsing craigslist, she stumbled upon an “adult” section listing girls who were escorting to make a little money on the side. “Why couldn’t I do this?” she thought. She had a comfortable job with flexible hours, but she had debts that she wanted to pay off and a husband who just didn’t take much of an interest in the family’s finances. She also carried a belief that men weren’t meant to be with one woman their entire lives. “If you look in the animal kingdom, that’s not the way it’s done,” she says.

So Michelle began escorting. She began to see multiple men per day between one to four times per week. And she did it without getting caught by either her boss or her husband. How? “It’s just like a guy who is cheating on his wife,” she answers. “You say you’re meeting with friends or you do it on your lunch break.” Like a cheating man, Michelle lives in fear that her family might one day discover her secret. It doesn’t help that she has a website. “I came close once,” she said. “I was updating my website and my husband caught me. I deleted the file I was working on immediately and had to tell him what he saw was a description of a friend.” But despite the close call, Michelle believes that she’s safe, even though she has an online presence. “To find me, you have to go searching for me on a site I’m affiliated with. My husband doesn’t use those sites.”

Michelle maintains that her marriage is a happy one, even in the bedroom. If she caught her husband cheating she would be truly hurt, though not “upset.” That would be “hypocritical.” With her husband, she says, “sex is a truly emotional connection. With clients, it’s just physical. If I weren’t so happy in my marriage, I could see getting attached to my clients. Depending on the chemistry, the sex can be amazingly passionate.”

Clients can retain Michelle’s services for $400 an hour or $700 for two hours. They can also purchase an “overnight indulgence” for $2,500. Michelle will meet them wherever they choose, whether it’s in their homes, or hotels they are staying in (not Motel 6, she says), or their yachts. And Michelle insists that clients need not be interested in just sex. “I had one guy—he was married and he worked—who drove over six hours to meet me for brunch. We just talked about family, life, hobbies. Sex only came up at the end for about ten minutes.”

How lucrative is Michelle’s second career? “I make way more in a day as an escort than I do in a week at my job,” she says.

W. Dyer Halpern is a former staff writer for Westchester Magazine and a current Assistant District Attorney in the Bronx. His law degree provided him with the information-gathering skills necessary to expose (pun intended) the previously unexplored world of prostitution in Westchester.


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