From good girl to prostitute: My path from ultra-Orthodox Judaism to Craigslist sex ad

I was a rabbi's daughter with my own ideas and unforgiving parents. Sex became a very complicated rebellion

Topics: Books, Love and Sex, Religion, Judaism, Orthodox Judaism, Sex Work, Prostitution, Editor's Picks,

From good girl to prostitute: My path from ultra-Orthodox Judaism to Craigslist sex ad

I woke in the middle of the night to the sound of shrieking laughter. Someone was banging on the door across from my apartment.

Shut the fuck up, I seethed, burying my head under the pillow. I had to be at work before eight to prepare for a presentation, which meant getting up at five forty-five. I needed sleep. Stuffing my fingers in my ears, I jealously contemplated my neighbors’ seemingly easy lives.

I had chosen freedom, and I had paid the price: The loss of my family. Too much heartbreak. PID. But where was my delicious free-for-all? Where was all the candy sweetness of sin I had been so direly warned about? Wasn’t that supposed to come along with its toxicity? All I seemed to encounter was rejection and disappointment. What other commandments would I have to break to access the goodies?

The shouting in the hallway continued all night. As light came through my window, I finally fell into a shallow sleep. It seemed only a moment had passed when my alarm went off, a sharp ringing beating into my brain.

I lay in bed, stiff with anger. I was exhausted, but my mind felt oddly clear. I saw everything with new eyes, as if I had wiped foggy glasses clean.

I took in my mattress on the floor. The dried paint running in frozen drips down the pockmarked walls. The wooden fish carving and the broken planter on the windowsill. The dollarstore necklaces hanging from a nail on the back of my door. The heap of dirty clothing on the floor.

I saw my life as if it were spread before me: the strict conventions of my professional job, the modest paycheck that denied me the flirty dresses I craved.

I thought of Tim, the long-haired hipster boy down the hall, who had introduced himself enthusiastically when I had first moved into the building. He had brought over a couple of beers, complimented my ass, and spent the night, but he had subsequently returned my enthusiastic greetings in the hall with grunts. And there had been Thomas, my old classmate, and the Irish bartender, and the one-night stand with a timid investment banker I had met through Craigslist, and Josh, the Star Wars fanatic I had met on the train, who had not been the boyfriend I’d thought he might become, and the hip-hop boys from Bushwick, and the biker boys from Park Slope, and the all too many disappointments I had pursued over the past year, as my liberated sexuality sent me hunting for satisfaction. Men flocked to me, but I was an abject failure at retaining their interest beyond a first or second date. It had been the same with Jacob and Nicholas and Duvi. Magic at first, that evaporated too soon.

My life was a mess, I realized, turning over and hiding my face under my arm. I was trying to create the life of a normal secular young person, but I was not normal. I would not metamorphose into a regular American girl. I was a crazy, broken slut, weighed down by a history that tormented me in nightmares. The life I was trying to craft was doomed to failure. I had to make a move, and there was only one direction in which to go.

I would become a prostitute.

* * *

The choice I made that morning felt inevitable. Girls who left Yeshivish life always became sluts and whores. This had been taught to me all of my life. I could never turn into a healthy irreligious woman. I now saw that this was not because of some divine punishment— no. It was because the journey out of the cloistered community I had been raised in was too difficult. The distance from modest girl to free woman could not be traversed. I would never have the confidence of a woman who’d received parental love regardless of her lifestyle choices. I would never relate to men the way a woman who had safely explored her sexuality in high school or college could. I would be stranded in black space between the world I came from and the world I wanted to enter, always falling short, always hurt, always failing. I might as well give up clawing away in the direction of a future that would never be mine. I might as well embrace my brokenness. I might as well wield it like a sword. I would not fall into the prophecy of doom; I would jump into it, feet first. I would be a smashing success at being bad.

Having rejected the laws of my upbringing, I had adopted few new morals. Sex was not sacred to me. And most importantly, I was good at it. My curves grabbed men’s attention, their interest fueled my confidence, and in the act, my desperation to please left my lovers more than satisfied. I was clueless at relationships but fantastic at attracting eager men and thrilling them that first, magical time. I might as well pursue my strength, I figured. I did not pause over the dangers of prostitution. I did not worry about disease. The PID had probably left my insides dead. I felt I had nothing to lose.

At work, later that day, I opened up the websites for Craigslist and the New York Times. No one could see my computer screen without me knowing, but if someone did barge in, I had a quick decoy at hand.

“SWF seeks Mutually Beneficial Arrangement,” I typed in the subject line. That was how the girls said it. I had seen the ads on desperate nights when my hunger had sent me browsing through the listings.

The cursor blinked as I peered into the mirror taped to my computer. Big brown eyes. Thick, long lashes. Broad, hooked nose. Tan skin.

“I’m petite,” I wrote. “Pretty. Brown eyes, long brown hair.”

How much money did a hooker make, I wondered. Probably a thousand dollars a night. Maybe two. No income tax. No Social Security. Two thousand bucks for a little flopping around. Two thousand dollars to be all sex. I could imagine myself in a tiny leather miniskirt, full breasts rising out of a glittery tank top, thick hair swirling over my shoulders as if an invisible fan whirled in front of my face. Leah, man, she’s a great lay. What do you do? I’m a prostitute. I envisioned a new apartment, a penthouse in Manhattan: all white carpeting and silk sheets. Sleeping in till ten every morning, accepting wads of cash from men desperate for me. No more “Here’s your reports.” No more pin-striped trousers and button-down shirts and seven a.m. alarms. No more wrecked romances and depressing flings. No more frustration at being a failed good girl. I’d pursue the basest of base callings. I’d be the baddest bad girl around. They pay me to fuck ’em. Sex on a stick.

I clicked Submit.

In minutes, my in-box was crammed with e-mails. I opened the responses, flipping from Craigslist to the New York Times site whenever anybody passed in the hall.

Most of the men had attached photos of their erections. The pictures made my stomach turn. Dumb men. Did they think that’s why I was interested? I wanted the desperation in their fingers, the proof of their want digging into my stomach. I wanted a role that I could be good at.

The longest e-mail got my attention:

“I am a lawyer,” it read. “My name is Stanley. I am 48 years young. I live on the Upper East Side. I have two adorable dogs named Lucy and Spot. I enjoy reading all kinds of mystery novels and going to the Met. I love the idea of a girl wanting a no-strings-attached relationship. So refreshing! Send me an e-mail and let’s get to know each other!”

The guy’s picture was a close-up of his face. He had heavy eyebrows that reached for each other across the bridge of his nose. His lined forehead merged into a bald head.

“Well, not no strings at all,” I wrote. “I am doing this to make money.” I cringed as I typed, afraid I’d sound greedy. Afraid I’d scare him off.

“That’s no problem at all,” Stanley replied, almost instantly. “You’ll meet my needs and I’ll give you what you need. I make a good living. I have no problem with that arrangement. Call me!” He included his number.

I could imagine giving him what he needed. How those eyes in the photograph would widen at the sight of me undressing. I could delight this Upper East Side lawyer. I could open my legs and leave him gasping. I’d had my share of gangster players and cool, hard hipsters. A forty-eight-year-old lawyer with two adorable dogs? Piece of cake. I’ll give you what you need. I could see myself modeling lacy lingerie for him, leaving Saks loaded down with frothy bags, Stanley gushing at my elbow, hailing me a cab, massaging my feet, moaning as I pushed him back onto a new leather sofa.

I found a quarter in my desk and went out to the pay phone in the hallway.

“Hi,” I said when he picked up. “Hi, it’s Leah, the girl from the Craigslist ad.” I cupped my hand around the receiver. There was no one in the hall, but you couldn’t be too careful.

“Oh, hello there, Leah. It’s great to hear from you.” His voice surprised me. It was deep. Velvety. I’d thought it would be more high-pitched.

“Have you ever done this before?” he asked.

“No,” I said with a nervous laugh. “Never.”

“What are you? Hispanic?”

“No,” I said. “I’m Jewish.” It felt odd to wrap my mouth around the word “Jewish.” It hardly seemed true anymore. I hadn’t spoke to my parents in over a year, but they’d stopped considering me really Jewish a long time ago. My three older sisters, who pretended I was dead, and my six younger brothers and sisters, who barely knew I lived, felt the same. Jewish was in the blood, passed down through the mother, but it seemed that a girl could do enough things to wash that legacy away.

“What are you wearing?”

I described my skirt and turtleneck.

“Are you wearing underwear?”

I knew what he wanted to hear. “No,” I lied.

“Mmmm. I would love to see you,” he whispered. “I’m getting hard just imagining you, your skin, touching you. I’m touching myself, thinking about it. Can I see you? Can I come now? I’ll hop in a cab. Can you see me?”

I loved the urgency in his voice. “Okay, fine.” I gave him my address. It did not cross my mind that relaying this information to a stranger might be unsafe. Having rejected my conditioned fear of the stranger, I had never reintroduced the concept of prudent caution.

“Can’t wait to see you in person,” he said.

We said good-bye. I sent my boss an e-mail saying I had a headache and was going home.

* * *

My apartment was a mess, as always. I tugged the sheet over the mattress, scooped books off the floor, folded the bathroom towel, and hid a box of tampons behind the toilet. I grabbed a handful of Band-Aids and stuck them over the patch of crusty scars on my arm.

The doorbell rang, and I went to open the door. There he was. Stanley, wearing a leather jacket over a gray T-shirt, his hands shoved into the pockets of his jeans. He was shorter than I’d expected.

“Hey there,” he said.

I stepped back, and he followed me inside. Stanley, I reminded myself as I gave my cheeks a quick pinch, pinking them up. What does a prostitute say? Hey there— hello. How does a woman sound sexy, mysterious, alluring?

Within seconds of entering my apartment, he stepped up to me, wrapped his arms around my shoulders, and buried his nose in my neck.

“Oh God,” he whispered, pushing his body against mine. His fingers sank into my back and dragged down my body to my behind.

“Ohhh,” he sighed. He fumbled at his waist, watching me as he pulled down his pants, lifted his shirt. I kept my eyes on my own body, yanking off my top and unhooking my bra quickly, so he wouldn’t see the safety pin on the strap. I didn’t want to have to look at him. Up close, it would be fine, but a few feet away, I found men doughy and misshapen. The sight of him would dry up whatever desire I had.

Think of the money, I reminded myself. Think of the hundreds of dollars waiting for you at the end of these few minutes. Think of seeing the boss tomorrow morning and saying, I quit. Think of walking into any store you want, pocket bulging with cash. Think of those black thigh-high boots with the cuffed tops that you saw in Macy’s the other day. Perfect with a pair of fishnets and a little black dress. Imagine that Leah: gorgeous, in charge of a glamorous, badass life.

* * *

Stanley followed me to the bed. I lay down and he climbed on top of me, grabbing my breasts.

“God, you’re beautiful,” he moaned. I kept my eyes squinty, so he was just a fuzzy blur, as I arched my pelvis into him. I wanted it to start so it would end, so I could get to that point where he’d pulse with relief, mission accomplished. Satisfied.


He pushed against me. I separated my thighs.

“You’re wearing a condom, right?” I murmured.

“Yeah, yeah,” he gasped as he plunged into me. His jaw dropped, his eyelids closed as he moaned. He was probably lying, but he was already in. There’d be no point in stopping him now.

“You’re so tight, so hot,” he groaned, thrashing against me. I kissed his cheek, his chin. My mind went blank, as it often did at this point, as we got into the friction, the repetitive back and forth of the thing.

He shoved. He pulled. He moved in and out.

“Yeah, oh yeah,” I moaned, encouraging him along.

“Yeah, oh yeah,” he cried, sinking his face into my shoulder, filling my nose with his smell of clean skin and cologne.

It went on. The thrusting. The rubbing. This was not like other men, engorged with appreciation for me, coming desperately, uncontrollably, as I moaned for them, kissed them, ran my hands over their flesh. Stanley kept going.

I clenched with each push in, tensed with each draw out. My insides were raw and hurting.

“Oh yeah, babe, so good. Oh yeah.”

My jaw was tight, my eyelids squeezed shut. One, two, three, four, I counted in my mind. Thirty-one. Thirty-two. Thirty-three. HaShem, I cried out silently. I had not used that name in so long. HaShem. HaShem. But I did not think God would hear a prayer from a rabbi’s daughter impaled beneath a sweaty stranger.

“Oh, oh, oh.”

And then, with his face buried in my shoulder, he moved his wet lips against my skin.

“Tell me you love me,” he murmured.

I craned my neck to lick his ear. It was just a thing he was saying. He wouldn’t be serious. Love. None of this— the nudity, the intercourse— meant a thing. But love, that was sacred.

I moaned, changing the subject. Sixty-one. Sixty-two.

He lifted his head. I opened my eyes. Drops of perspiration sparkled on his nose. His eyes bored into me.

“Tell me you love me.” His palm framed my head. His body stilled as he stared at me, his thighs pressing into mine.

I reached for his skin with my lips. I loved nobody. I gave that to no one now.

Stanley pushed my face down with a firm hand.

“Tell me you love me,” he repeated. His fingers sank into my cheek.

I swallowed hard.

“I. Love. You.” I managed a smile.

He lifted his chin with a sigh and shuddered. He sat up. I saw that there was no condom.

“I’ve got to get home,” he said, putting on his clothes. “My dogs are going to miss me.”

I rolled up to sit and hugged my legs in.

“Um— what about— the— the money?” My voice was barely a whisper.

Stanley laughed. “Oh, don’t worry,” he said. “As long as you aren’t asking for a black American Express card, I’m sure we’ll work it out. I’ll be in touch soon. Okay then.”

He grabbed his jacket and waved good-bye.

The click of the door rang out in the quiet apartment.

I fell back on the sheets, rolling to face the wall, cupping my burning crotch in my hand, applying pressure to the chafed skin.

“Poor stupid little baby,” I whispered.

Excerpted from “Cut Me Loose: Sin and Salvation After My Ultra-Orthodox Girlhood” by Leah Vincent. Published by Nan A. Talese/Doubleday, a division of Random House. Copyright 2014 by Leah Vincent. Reprinted with permission of the publisher. All rights reserved.

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