The Price: My Rise and Fall As Natalia, New York's #1 Escort

by Natalie McLennan

  I read about her screwed up childhood, where she alluded to childhood abuse and her drug addiction. She grew up in a rich suburb of northern New Jersey with her mom and her oral-surgeon stepfather. In the middle of high school, she moved to North Carolina to live with her real dad and showed up in New York not along after graduating. Her family may have had a lot more money than we did, but like me, she was a wild child who’d split town to seek something better.

  I worried that that our shared spirit might mean she was reckless. And in this business, you need to be careful with every move you make.

  “Ash, do you know how to stay safe?”

  She picked a condom up off my dressing table and held it in the air with a “duh!” expression on her face.

  I laughed, “That’s not what I mean. Like, legally?”

  She shook her head no.

  I explained to her the way it had been told to me. As escorts in New York, we existed in a legal grey zone. We weren’t prostitutes soliciting clients on street corners, charging $50 for a blowjob or $75 to go “around the world.” The way it had been explained to me is that we would be hired and paid legally for our time and companionship. Whatever happened between two consenting adults would be their decision. As long as it wasn’t explicitly stated that you were exchanging money for sex, you’d be okay.

  “Think of it like this,” I said. “If you go to your hairdresser, you get a haircut, and then decide to have sex with your stylist, that’s not illegal, right?”

  She nodded.

  “Here’s where you have to watch out: If a client ever mentions or even alludes to sex, or tries to get physical before the financial transaction has taken place, there’s a chance he’s a cop, and you need to get the fuck out of there immediately. If a client tries to offer you more money to have anal sex or sex without a condom, you should leave because cops supposedly are under orders to bust unsafe escorts. And you should never have sex without a condom, or in my opinion, have anal sex with clients. That’s just crazy. You can get really hurt.”

  She just nodded.

  “Any questions?”

  She shook her head.

  “I’ve never met any of your friends. Do they know what you’re doing?” I asked.

  Now that we had gotten through the legal stuff, I was curious to see if she was like me, building a life full of secrets. I was desperate for someone to talk to about it. Part of me hated the double life. But another part of me felt like I had tapped into some secret fast-track to happiness and success—a loophole in system that I wanted to share with someone who was doing the same thing. Everything I was doing was illicit and counter to the mainstream’s norms. But it all came so naturally, and I was having so much fun, I was beginning to think that maybe the whole of western society had it wrong, and we were the ones who had it right.

  “No, they don’t,” Ashley said. “And I’m planning on keeping it that way. It might really fuck me when I get my record deal.”

  “That’s totally cool. I understand,” I said. “So who’s your favorite client so far?”

  “There’s this hedge-fund guy. He’s like twenty-five or something. And he has this sick apartment on the park. The other night he took me out to Quo, and he fucked me in the bathroom. It was incredible. I have no idea what the fuck a hedge fund is, but hedge-fund guys are, like, hot,” she said, in her best mock-Paris Hilton.

  “Totally,” I said, giving her my best skinny, drugged-up Nicole Richie.

  “Are you going to see the guy again? I asked.

  She knew exactly what I was getting at.

  “If he books me again, yeah. I mean, I hope so.”

  As much as Ashley was growing on me, I tried to keep an eye out for girls who were stealing clients from the agency. It happened a lot. I was, after all, Jason’s girlfriend. But this girl knew how to play the game. She knew the better she was to the agency, the more money she would make. I knew part of the reason she was hanging out with me so much was exactly for that reason, and I was okay with that. I think we would have been friends anyway.

  * * *

  After a civilized brunch at Balthazar—heavy on the mimosas—I found myself in a chauffeured Escalade with Jason and Isabella on our way to the loft. All morning, Jason had been dealing with a Russian girl who used to work for him and Bruce, his former business partner, with whom he’d had that blowout fight over the phone. The split with Bruce created a mess: a bunch of girls didn’t get paid for past appointments. Neither Jason nor Bruce wanted to take responsibility and pay up. This girl in particular was freaking out and screaming into the phone that Jason had to take her pictures down off the New York Confidential Web site. He had been telling her for days that he would take care of it. Just as we were turning onto Worth Street, his cell rang and on the other end was an attorney calling on behalf of the girl. Whatever he said, it must have been effective because Jason went pale for a second, and for the first time I’d ever seen, he went speechless. But he quickly recovered and did what he did best: charm people into his world. Jason turned the tables and starting asking the guy a series of questions and discovered that the lawyer, whose name was Mel Sachs, had been an old friend of his mother.

  Jason flipped out. His mom was everything to him, and anyone who had known her was instantly like family to him.

  The original purpose of the call was forgotten, and Mel agreed to stop by the loft later that day. As an afterthought, Jason reassured him he’d take down the Russian girl’s pics.

  When we got to the loft, Hulbert told me Ashley was on her way over. She knew if she were around, she’d score more work.

  Jason made it known that if you hung out, preferably naked or in lingerie, he was more likely to book you. He liked—check that—loved having beautiful girls around him at all times. It inspired him—motivated him. It’s an instinct as old as the first harem. It was part of Jason’s personal philosophy, which basically boiled down to an obsession with beauty. You could say he was sort of a beauty-Nazi. He would actually argue that beautiful people were smarter and more trustworthy than ugly people. Sometimes it seemed that all he thought about or cared about was making sure he was surrounded by hot chicks. In some ways, it was sort of pathetic. Like he was making up for a personality or physical defect. But on the other hand, you could argue he was just an old-fashioned aesthete. The history of Western culture is full of great artists, thinkers and leaders who wanted to be surrounded by beauty at all times. I’m not saying he was a Degas or Gauguin. Caligula maybe, without the legions.

  Jason’s personal philosophy was an integral part of how he sold the New York Confidential brand to prospective clients: “Splurge on one of my girls, and your whole life will get better—their beauty and sexual energy will make you happier and more productive. Think of it like an investment in your general well-being.”

  I think there’s actually a grain of truth to it. Sex is the ultimate release, and the attention of a beautiful girl lifts any guy’s sense of self, even if it’s temporary and paid for. The thing that Jason didn’t understand is that most people have a conscience. He was so far gone, he couldn’t see that what he sold created a lot of guilt and regret, especially for clients who were married or in a relationship. And, in a second, those negative thoughts could destroy all the happy ones that were supposedly making them so carefree and focused. On the extreme end of the spectrum, many of our clients were as addicted to escorts as they were to drugs or gambling. For them, the “happiness” that Jason was peddling was part and parcel of their road to ruin.

  * * *

  It was one of the rare New York summer nights when the air is warm and clear. Ashley and I both had bookings: hers was an hour long, mine was two. We both managed to extend them for an extra hour, and when I got back to the loft, Jason was on top of the world. He worked hard to book us the best appointments he could, and when we managed to improve on what he had already done and earn more money that was magic in his eyes.

  Mel Sachs, who I later learned was som
ething of a legal legend—he had represented everyone from Mike Tyson to David Copperfield to Derek Jeter—had come by the loft while we were out. Jason couldn’t stop raving about him. Jason loved the fact that Mel had been a friend of his mother’s and knew of his family’s wealth and status—two things that meant everything to Jason.

  Jason’s real name is Jason Sylk. His “sperm” father, as he called him, is a guy named Leonard Sylk, the son of a drug-store magnate who once owned part of the Philadelphia Eagles. Jason’s dad did well with his inheritance, becoming a well-known businessman in his own right. According to Jason, he was famous in the Jewish community for being down with everyone from the bookies to the bagel makers. When Jason was little, he was the only Jew for miles in Philadelphia’s super-WASPy ‘burbs. His family had had an eighteen-car garage and a heliport pad. Jason told me that the prime minister of Israel had once stayed at their house.

  As a kid, Jason summered in the Catskills and became part of the Jewish rich-kid mafia. He hiked, swam and ate gefilte fish with guys like Jason Binn, who went on to start the high net-worth targeted magazines, Hamptons and Los Angeles Confidential. Jason worshiped Binn. Although Binn’s dad was a billionaire, he went out and created a booming publishing empire on his own. The New York Confidential name was a sort of homage to Binn’s chutzpah.

  When his parents got divorced, Jason lost connection with his real dad and became almost claustrophobically close to his mom. He talked all the time about how beautiful she was, how she was the original MILF. She married well again—this time to Ron Itzler, a big-time lawyer who lived in a posh part of Jersey. When she died of cancer, Jason was crushed. Jason was still in his twenties, and for all intents and purposes, Ron became his dad.

  Jason always talked about how everything he did was to make his mom proud. New York magazine later summed it up perfectly: his life was “a mini-epic of Jewish-American class longing, a psycho-socio-sexual drama crammed with equal parts genius (occasionally vicious) boychick hustle, heartfelt neo-hippie idealism, and dead-set will to self-destruction.”

  * * *

  Mel had invited us to the opening of uber-promoter Noel Ashman’s new club, NA, so Jason called for our stretch Escalade, his chariot of choice. Jason was toying with the idea of having one on call 24/7. He said it would be cool for the girls and make them feel like movie stars, but I secretly feared he just wanted a floating hotel room to book even more clients. Rooms in Manhattan’s best hotels can be expensive and hard to come by during peak seasons. And there was nothing Jason hated more than having us worker bees not making him money because we couldn’t get a nice room.

  I was so excited to be going out as a regular social person, I couldn’t contain myself. I was bouncing off the walls. I had been working nonstop for weeks. I downed a glass of champagne, did an enormous line and offered one to Ashley. She shook her head, and I offered it to her again. She leaned forward and did it. I realized Ashley probably hadn’t been partying that long. She was only nineteen and couldn’t even drink legally! I felt a twinge of guilt that I was leading her down a dangerous path, but the truth was I was selfish. I desperately wanted a girlfriend who could keep up with me.

  Her faced scrunched up as the powder shot through her sinuses. When your body isn’t used to it, coke can feel like Drano. I had been doing so much, it felt as normal as drinking an espresso. It was my fuel.

  Jason and Isabella were already in the limo. So we dashed out the door, giggling as we burst onto the sidewalk. We jumped in, and Ashley screamed, “Pump this bitch up!”

  Jason told the driver to turn on Hot 97’s Funkmaster Flex. The limo thumped with a heavy hip-hop beat. I could feel my heart flutter from the combination of the bass, the excitement and the coke. I gave everyone a knowing smile. They all smiled back. I felt invincible.

  We pulled up, and the doormen showed us right through. The club was cool, but it had the energy of a party just getting started. Mel greeted us as we walked in and told us to wait as he brought the owner, Noel. He immediately set us up at the first booth, right where everyone could see us. I assumed the New York club stance: I jumped up on the banquette and started dancing, helping Ashley do the same. I could tell she was a little edgy. Edgy feels like this: you aren’t comfortable in your skin, almost to the point where you don’t have total control over your body. The remedy is a drink, or ten. So I played bartender with the bottle of Grey Goose that had magically appeared on our table. She shook her head, again. I put it in her hand, and we drank up. She was beginning to learn the drill.

  We settled in, and I took a look around. As far as club openings go, it was average. It didn’t have the usual crowd of underage models, and, as a result, we were the main attraction.

  Ashley was glowing. I mean literally. I loaned her some shimmery lotion, which we rubbed all over her arms, legs, cleavage, you name it. It went perfectly with her tan. Remember the Versace dress J.Lo wore to the

  Grammys a few years ago? Green, flowy and cut down to her belly button and up to her cootchie? Ashley’s dress was kind of like that but sleeveless. She looked stunning. For a second, I looked down at my own tits and thought maybe I should reevaluate my feelings about implants. I tried to imagine what they would feel like and that’s when my “what if” fantasy dissolved. I liked being small in a Kate Moss way. I’d leave the Carmen Electra look to Ashley.

  Although she wasn’t my type, Isabella looked hot in an all-white outfit right out of Miami or Caracas. I never liked her super-long, French-manicured nails and flashy, South American look. Jason and I were big on the New York Confidential image. Remember how he made me stop and buy Manolos the day I got my first review? I didn’t buy it then. But over the weeks, I’d become a believer: clients were paying so much to see me, I made sure I delivered the whole package.

  Isabella’s style was definitely on my radar. I complimented her when she got it right and loaned her stuff when she didn’t. She didn’t mind, but she also didn’t seem to get it, which made her an ongoing project. There was more than just the agency’s image at stake. I was worried her skin-baring Latin look would draw too much attention, specifically the law enforcement kind. I loaned her a dress and helped her tone down her makeup, but I couldn’t do anything about her long, French-manicured acrylic nails.

  I decided to go a little extreme myself, Carrie Bradshaw-style, and wore a dark, silver metal, backless top, a super-soft, black leather skirt and my new present from Jason: the most expensive Manolos ever made. They were full of Swarovski crystals and made me feel like a rock star. Beyonce wore them that year when she performed at the Grammys. Between my sparkling

  Beyonce shoes and million-dollar strut, Ashley’s cleavage and J.Lo dress, Isabella’s Colombian accent and oscillating ass, the Escalade limo and our “manager” Jason with his diamond Cartier watch and 10K in cash folded in his pocket, we were on fire—the sex industry’s version of Charlie’s Angels. The whole vibe made me really horny. I was secretly praying for a late-night booking.

  I looked over at Jason. He was beaming. Mel brought over a well-dressed guy in his early thirties and introduced him as Andrew, a designer and owner of a high-end boutique on Madison in the Seventies. Well, that’s what Jason told me when I asked him later that night. I couldn’t hear a thing between the music blasting through my head and the coke flowing through my veins.

  Ashley started dancing with me, and I pulled her in close, and we started making out. I was making Jason proud, and I was having fun. Jason had become the most important person in my life, and I liked making him smile. Ashley knew how to play the part just as well as I did. Our session started to draw a crowd, entirely male, eager to become part of our circle. Jason stepped in like P. T. Barnum , introducing each of us to the throng as he helped us down off the banquette. The guys swarmed around Ashley. She really knew how to get guys into a frenzy. She definitely made me feel a little threatened, but I liked the challenge. She was exactly what I had hoped she would be.

  Soon, though, the club
got boring. You can only dance on a banquette for so long before it gets old. Without anything to look at, or anyone else to meet or talk to, we lost interest. We made a move to our waiting chariot with Mel and Andrew in tow, and Jason told the driver to take us back down to Worth Street. I looked Mel over. He was wearing a custom-tailored suit, shirt and a bow tie—apparently his signature look. Andrew wasn’t the best-looking guy, but he was super well-groomed and immaculately dressed. I jumped onto Jason’s lap, and Mel focused in on me, complimenting me on my beauty and energy. His voice was like raspy velvet. Jason whispered the name of Mel’s most recent client.

  “Whoa! You represent Lil’ Kim!” I’d had quite a bit to drink and couldn’t hold back.

  “Natalia, you have to come meet her Thursday night. She’s performing at Marquee. I’ll introduce you. It’ll be fabulous.”

  I’d never heard a straight man say fabulous and make it sound so good. We arrived at the loft, and Ashley, Isabella and I floated into my closet and checked ourselves out in the mirror. We each did a line, and I thought to myself: Okay, maybe that’s enough for tonight. I need to sleep sometime.

  “NATALIA!” Jason’s familiar call for me drifted into the closet.

  Ashley and Isabella went back to the men, leaving me alone in my closet.

  “NATALIA! Get out here! I have a booking for you!”

  My smile dropped, and I looked into my eyes in the mirror, then squeezed them shut. I touched up my make-up, grabbed some condoms and a credit card imprint form and slipped them in my purse. I stood up tall and put my smile back on. I went into the living room and waited for Jason to give me the details.