Sex
Ashley Eskew writes an essay about doing sex work and babysitting to pay off an $8,000 debt.

I Worked As A Babysitter By Day & A Sex Worker By Night

Above Times Square, I was the girl every mother called a role model, and below Times Square, every father just called.

By Jash E.
Getty Images/Guille Faingold - Stocksy/Shutterstock

He pointed towards the unopened box of surgical gloves and dropped his pants. Ever the rule-lover, I followed his lead and snapped on my latex glove à la Nurse Jackie before digging in.

“No!” he cried with a faint Indian accent. “You’ll need the lube.”

Of course. The lube. I smothered my glove in it as my client’s annoyance turned to sympathy.

“First time?” he asked.

I mean… the closest thing to a** play I’d experienced was wiping too hard with single ply. Yes, this was the first time I’d massaged a man’s prostate. As I plunged inside him, I had three thoughts:

  1. I hope this guy is a good tipper.
  2. If I stop by the bodega on 30th Street after this, I can pick up a snack for Noah, and then we won’t have to rush to hockey from pick-up.
  3. This guy moans like Kermit the Frog when he comes.

When I was 24 and living in New York City, I was a sex worker by day and a well-known babysitter by night. I loved being both.

A run-in with a professional squatter had left me $8,000 in debt and on thin ropes with my live-in boyfriend, who was experiencing severe panic attacks from the financial and emotional strain. I needed a quick fix — and after a few Backpage.com searches, I found it at a rub ‘n tug hidden in a quiet apartment building in the Flatiron District.

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I already had a part-time job babysitting for the most wonderful kids on the Upper West Side, Noah and Rebekkah (names have been changed). It provided community, affirmation, and a way to fill my ever-widening financial gaps as I pursued my dream of acting on Broadway. But rent was due and Backpage had a wealth of opportunities that didn’t involve asking anyone else for help. I was educated, capable, and frankly curious if anyone would find me attractive enough to pay to pleasure them. Penetration wouldn’t be an expectation — just a regular massage I performed in lingerie, ending with a handjob.

Handjobs were so innocent, high schoolers did them in their backseats after football games. I was dipping my toe into the murky waters of sex work, not diving in. Also, my clients would be in and out in 30-minute windows, so I wouldn’t be building real relationships with anyone. It was completely anonymous work where I would be solely giving and not receiving, perfect for a natural codependent.

I justified it as an extreme acting job in which I would step into someone else’s identity and bail once I met my financial goal. I thought it would never affect my personal dreams or relationship with my boyfriend, especially since I planned to never tell him. It was practically an off-off-Broadway play... with better compensation.

A no-bullsh*t woman responded to my Backpage.com inquiry, and within a day, I was touring the frill-free apartment where the business was housed. There were three bedrooms: a “treatment room” with a single massage table, a laundry room (which was more essential than you can imagine), and an office where the woman’s daughter colored in pages of Pinkalicious as I visited that first day. She explained that this setup made it so only one woman could work in the apartment at a time, meaning I’d be completely alone with my clients. She told me not to worry because there was a security camera in case any “incidents” arose. It seemed like an imperfect system, but I was at an age where mortality was conceptual and the fear of disappointing someone was more frightening than any of the “incidents” she quickly alluded to.

I had been a “nice girl” my whole life, and I was convinced that once I did this work, I could never be “nice” again. That’s why I chose a stage name (Renée, after a high school frenemy I’d always secretly admired). It would be an easy way to dissociate. Renée would be the one massaging oiled foreskin to climax while I’d reappear (post-hand wash, of course) at Noah and Rebekkah’s pickup, then home to my boyfriend for a cuddle and an episode of How I Met Your Mother.

Both jobs let me channel my need for affirmation into a money-making tool.

The business ran on regulars, but the hope was that my new faceless boudoir photos — like reverse headshots, I had practically trained for this — would bring in fresh blood. Every client would pay a base of $180 for 30 minutes of my time (this was 10 years ago.) The house typically would pocket half of that ($90) while I would take the rest plus a tip (often generous, $100 - $200.) The more clients I’d see in a week, the higher percentage of their payment I would pocket. I calculated how fast I could pay off my debt — it would be a few months, part-time, if not a few weeks. But I was still hesitant.

That evening, back on the Upper West Side, I acted out the entirety of Wicked in full green face paint, then began the nightly ritual of putting the kids to bed. It was the best part of the job: a magical time when we were all sleepy and loose-lipped, sharing cuddles and swapping stories. As Rebekkah splashed around in the tub, I wondered if it would all feel different the next day, once I started working at the rub ‘n tug. Would Rebekkah somehow know that the label “sex worker” would soon be a non-erasable part of my identity next to sister, daughter, actress, and girlfriend? I felt a rush of shame creeping up when she splashed me.

I reminded her to wash her “hooey,” the PG word my mother had created when I was a kid to refer to a girl’s private parts. Rebekkah grabbed her sponge, plunged it into the suds, and reminded me flatly that it was called a “vagina.” If this kid could be sex-positive, so could I.

I started the next day with a creeping suspicion that maybe “nice girls” were just “regular girls” with better-kept secrets.

The work felt immediately familiar. While both jobs led to me being literally sh*t on (at least I was safely wearing latex gloves at the rub ‘n tug), they also made me feel needed for skills that I was inherently born with — a stark contrast to my fizzling career as an actress on Broadway. I could anticipate others' needs, whether that meant laughing harder at Noah’s jokes on days he was bullied at school or spending a few lingering moments on my clients' nipples.

By channeling my constant need for affirmation into a money-making tool instead of a point of shame, I began to set healthy boundaries and only accepted jobs that paid what I was worth — a practically impossible ask for a music theater actress just starting out. The lessons even bled into my sex life with my boyfriend. Now that I was a literal professional, I felt I could ask for what I wanted in the bedroom with confidence, even though the man I chose to have in between my legs each night didn’t know the totality of who I was.

Above Times Square, I was the girl every mother called a role model, and below Times Square, every father just called. One man did, however, dip into both worlds. He was the kind of father I dreamed my boyfriend would become someday, creative and successful with a boisterous laugh that only came out when truly earned. One night, I supervised a sleepover with five 6-year-old girls. New York City tends to creak and screech, and no amount of logic would assuage these young ladies’ bedtime fears. So, I leaned into them. The father helped me burn the edges of white printer paper as I wrote an “apology note” from a friendly ghost named Clarence whom I said sometimes visited in me in my apartment, too. I explained he was just there to make sure the girls were safe and hadn’t been sneaking extra sweets.

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I was less than thrilled to see this father pop up in Flatiron ready for a massage and a handy. I am still unsure if he tracked me down or was just looking for a lunchtime release and happened upon my workplace. Either way, I knew it spelled mutually assured destruction. I passed on his business and paid for the half hour out of pocket so my boss would never know I allowed a client to walk. I was grateful for the reminder that amazing fathers aren’t always amazing partners; he was supposed to be in a monogamous relationship, but struggled with the monogamy part.

Not all married men approached me as a secret. Most told me personal details about their partners. One even brought his wife, who suffered from severe arthritis, into the room to guide me through what he liked. Her lavish bracelets and rings clanked together as she demonstrated strokes that caused her too much pain to perform.

It wasn’t glamorous work— the room reeked of cum and Clorox — but I enjoyed meeting the menagerie of men, who ranged from former NFL players to HBO crew members. Their bodies ranged from uncut d*cks covered in raised moles to micropenises that required just my thumb and forefinger to get the job done. When I realized I wasn’t facing these bodies with judgment but curiosity, my own struggles with beauty standards were thrown into perspective. My sexiest clients had one thing in common: they knew who they were and what they needed in order to leave our 30-minute appointments satisfied.

I made the $8,000 I needed in only three weeks before I walked away from the rub ‘n tug for good (an admitted indication of my privilege). When I returned to my (practically) handjob-free world, a lot came into focus. Noah figured out that bullies are usually in pain and invited his to hang out more. Rebekkah turned her biggest fear into her best friend by greeting Clarence the ghost every night before bed. As for me, I realized that if I wanted to keep my relationship, I’d have to strip down for my boyfriend like my clients once did, and share my imperfections and vulnerabilities. I hoped that by owning them, we could both be satisfied. Luckily, my boyfriend also approached the situation with curiosity instead of judgment, and we’re now engaged.

For years, my fear has been that I am not a bright, capable role model who brings light to every room, but am in fact wrong or dirty or bad for having been a sex worker — or honestly, even a sexual person. It’s haunted me for years, and it’s kept me from achieving personal and professional triumphs because I figure the more visible I allow myself to become... the more people might actually see me. But this small chapter of my life was not a shameful mistake. It was a liberation point in my journey. I hope the clients I served feel the same about their time with me.

So today, I’m taking a lesson from Rebekkah and inviting my deepest fear to be my best friend. When I was 24 and living in New York City, I was a sex worker by day and a babysitter by night. I loved being both.

Good night, Clarence.