The First Time I Got Paid for Sex I Did Everything Wrong
I drove into the parking lot of a cheap motel in the San Fernando Valley—the porn capital of the world. It was the kind of place where the exposed balconies lead to bright orange doors. I remember thinking there was way too much activity for a random Wednesday at lunch time.
I was on high alert—maybe it was the nerves. I noticed people loitering, making deals of the illegal substance kind, and a few who looked to be cruising. I could tell this place was a hotbed of illicit activity—and I was about to add to it.
I took a deep breath and called my booking partner for the room number. “He’s in 103. Be careful. Call me to check in,” she said.
I never would have thought I would do something like this, but there I was taking that brisk walk across a seedy parking lot to a motel room door on that unseasonably warm June day so I could meet a man I didn’t know to pay me for sex. I tried not to think too much about what I was about to do as I knocked softly on that bright orange door and waited for it to open.
I could have never imagined that when the Twin Towers came down on 9/11 it would lead me to become an outlaw. A month after the attack, I was laid off from my fancy job as an art director in advertising as work dried up amid a collective uncertainty about what the future held. I had only recently moved from the Eastside to West Hollywood to be closer to my job. Now my Doberman, Maximo, and I were living off my cashed-in 401k to buy food and pay the rent.
As funds depleted I noticed an ad in the paper that said “Girls with good voices get paid cash daily.” I was a girl, I had a good voice, and I could use cash daily. I figured it was phone sex but the job was actually answering phones for an escort agency. The job sounded simple enough—I would pretend to be the girl in the ad and convince the caller to schedule an appointment. I became what the industry refers to as a ‘booker’. The escort would take 50 percent of the fee plus all the tips, the agency would take 30 percent and the rest was mine.
The phone never stopped ringing and I soon found I was able to comfortably support Maximo and myself in the manner to which we had both become accustomed—food in our stomachs and a roof over our heads.
Eventually, another booker and I branched out. We figured why only make 20 percent of the fee when we can make all of the agency split and provide better support for the escorts. So we started our own service.
The problem we soon found out with booking calls and dealing with escorts is they can be very unreliable. The most popular girl, Kacey, who I booked for, was also the most unreliable. She’d call on to work then disappear for days.
That hot day in June my partner called me in a panic. She had booked Kacey a call and she was nowhere to be found. My partner didn’t want to lose another client because Kacey had disappeared again, she had rent to pay and kids to feed. I don’t know what came over me, but in that moment, and mostly in an effort to stop her crying, I told her I would take Kacey’s place.
We sort of looked alike in that we were both tall brunettes—although that is where the similarities ended. It was going to have to do. I headed out dressed in what I wore all the time—a short black skirt, tank top and my much-loved knee high, lace-up, boots. There wasn’t time to think about clothes. I had to get there in a hurry.
A good-looking black man in his late thirties opened the door and invited me in. The room was dark, the shade was closed and only a beam or two of light was peeking through. He motioned for me to come sit next to him on the bed. I was nervous. Very nervous. I’m sure it showed even though I tried to act cool.
I had booked hundreds of calls for other people. I had hundreds of conversations with sex workers about what to say, what not say, how to stay out of jail and how to keep themselves safe. All that flew right out of my head, and I did everything all wrong.
I started by negotiating sex for money, which is an industry no-no. I just broke Rule #1—never talk sex and money. If my new client had been a cop, I’d have been arrested on the spot. I wouldn’t have passed Go, and I certainly wouldn’t have collected $400. Luckily for me he handed me the money, which I quickly put in my purse.
The sex was fast, it was surprisingly pleasant, and it was easy. Twenty-five minutes later he was happy and I was richer. I’d had worse times with men I’d been on legit dates with. We got quickly dressed and both walked to our cars. Out of the corner of my eye I saw he jumped in a white convertible Mercedes and sped away.
I had no feelings of guilt or shame, but I was excited about the cash. Four hundred dollars cash for 25 minutes work! I started adding up what I could make if I saw one client a day. What if I saw two? Three? Nothing about the sex was exciting for me, but the idea of making rent in one day? That was a huge turn-on. That’s what really got my panties wet.
My phone ringing took me out of my daydreams of paying all my bills with a few hours of work. It was my booking partner. “Why haven’t you called me! Are you ok?!!” I had just broken Rule #2— ALWAYS check in with your booker after you get the money to let them know you are safe and that everything’s OK.
Jenny DeMilo broke Rule #2 of sex work—failing to let her booker know she was ok.
While driving home I considered if this sex-for-money thing was something I wanted to do again. Sure, I did everything wrong. I broke the two cardinal rules and it all could have gone sideways. But it didn’t go sideways. Not even close.
After about a week of mulling it over, I decided to try it again and I put up my own ad. My second time having sex for money I was much more professional. I didn’t make all the rookie mistakes I made the first time. In fact I was learning as I went.
Client No. 2 was unremarkable in as far as he was a middle-aged, overweight, married man but it was during this session that I discovered what most clients want out of you—they want you to be happy to be there. He took longer than 25 minutes but that’s only because he thought he had to seduce me—I think he forgot I was a sure thing. I made sure to laugh at all his jokes and tell him how much I was enjoying our time together. It was a lesson that would keep me in demand as a sex worker.
My new job saw me touring other cities like I was in a band. Even better than touring like a rockstar was a “fly me to you” date. Not because you would see any sites in a new city but because you’d make bank. Overnights in cities across the country were my jam. Even though I’d tend to hide in the bathroom playing games on my phone while my client snored in the other room. Sleeping in beds with strangers isn’t easy—ask any sex worker.
I discovered escorting was just like any other job. It had good days and bad days. Some days I loved my job and couldn’t imagine doing anything else. Other days I hated it and would threaten to quit. I set my own hours, I worked as little or as much as I wanted and I bonded with other sex workers. This misunderstood community became my main support.
No one in my real life knew my secret life as ‘Jenny’—the pay-for-play naughty girl. They would never understand. So I lived a double life. But among my fellow sex workers I found friends who I could share things about our line of work that are usually met with a huge stigma in society.
I started mentoring girls new to the business and became an advocate for sex workers’ rights. My job wasn’t like you see on TV and movies or read about in tawdry romance novels. It was just a job. A job that sometimes meant I’d jump on a plane to D.C. to see a politician or drive to a cheap motel in the valley with ugly orange doors to see a good-looking Black man.
Jenny DeMilo admits she was excited about the money she was making, counting it every night before bed.
I would count my money every night before I went to bed. I had fun, attractive clients where I couldn’t believe I was getting paid to be there and then there were boring clients I forgot the minute I walked out the door. Most of them were easily forgettable and that’s the way I liked it. The price of admission was high. My rates kept going up. By the time I retired from escorting I was charging $1,000 an hour.
I transitioned after a decade of pay-for-play employment to legal sex work. Escorting had run its course and I was getting bored. It was time to try something new. I started to work as an online Dominatrix. Specifically, a hypno-domme which is its own special fetish niche for girls with good voices. It’s a job I still do today.
The whole time I was working as an escort I continued to work as an art director, though it had become more of my side hustle. My hustle was my real hustle. To the outside world it appeared that I was just regular old me with a regular old job. But I was anything but regular—I was an outlaw living a double life.
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