Some Decisions can be Delegated. Who You Sleep with Isn’t One of Them


Caroline handed me one of her cell phones. “Leslie, here. You’re making my appointments from now on.”

“Me?” I said. My voice sounded kind of squeaky, so the word “me” wasn’t really a whole word. More like a breath shaped around the letter “m.”

Caroline pursed her lips. “Come on. This is your job. You’re my personal assistant. So you make my appointments.”

True, I was an escort’s personal assistant. I just didn’t think it was a good idea for me to plan who she would have sex with. I had no frame of reference for that duty. It wasn’t like choosing the right scent of Yankee Candles to create the proper “forget you’re paying for this” mood.

At least, I didn’t think it was like that. But if Caroline was picky about who she slept with, she wouldn’t have become an escort in the first place.

She shook the phone in my face, and I took it so she wouldn’t start yelling.


Moral 90: Not everything should be delegated. Decide who you’re going to have sex with your own damn self.


One time, I held a tarantula at an insect exhibit. The tarantula guy’s instructions were to keep my palm very still and flat, and not make any sudden movements. Then he put the tarantula in my hand and I acted like everything was cool.

That’s the way I held Caroline’s phone. I wondered if her phone could smell fear. Maybe it would ring just because it sensed I was nervous. I must not make any sudden movements.

Okay. I took a deep breath. I had been a secretary in the past, and worked in customer service. I knew how to answer the phone. I could answer questions. I could book appointments.

“What kind of clients?” I asked. I just wanted to clarify my new duty.

“What do you mean, ‘What kind of clients?’” Caroline asked. “The kind that can pay to do me!”

“Okay,” I said. Deep breath. Approach this like any other logical problem. What issues might present themselves in a booking call with a john? “Well, what if they ask what services they can get?”

Caroline was not impressed. And she was getting flustered. “You don’t ever describe any services! You don’t ever say I’ll have sex with them. You know that, right?”

“Oh, of course, I know that much. But what if they ask—”



Moral 91: In some conversations, what’s not being said, is what’s actually being said.


I wished there was some kind of training orientation for how to book appointments for a prostitute. But Caroline was never big on giving instructions. (Exhibit A: my job interview, in which she rattled off a list of stuff she wanted me to buy, handed me her credit card, and pushed me out the door. I didn’t remember half the stuff she told me to buy. She hired me anyway.)

“Look,” Caroline sighed, closing her eyes and pressing her red-tipped fingers to her forehead. “Just tell them they’re paying for forty-five minutes of my time. That’s all you say.”

Okay, I could do that.

“And screen them,” she said.

What? Screen them? What the hell kind of questions would I ask to screen someone who wanted to pay for. . .forty-five minutes of Caroline’s time? I must have blinked at her like an owl.

Caroline looked like she might bitch slap me. “LESLIE! You have to make sure they’re not cops! And that they can afford me.”

“Okay. . .What questions do I ask for that?”

“OH MY GOD! YOU ARE SO USELESS SOMETIMES! Seriously, is cleaning floors all you’re good for? Ask about their families, their jobs. Ask about the kind of car they drive and where they live, what kind of neighborhood it is. Get their zip code if you can. Whether they’ll be flying into Chicago first class or economy. Just get information. But don’t grill them. That’s not sexy at all. You have to do it in a sexy way.”

I could just imagine myself trying to interrogate johns with a phone sex voice: “Hi, this is Kira’s secretary.” Kira was Caroline’s favorite fake name. “When are you wanting an appointment?. . .Great, that sounds perfect for her too. Where do you work?. . .Ooo, sounds fun. What tax bracket do you fall into?. . .Mmm, that’s the sexiest tax bracket. . .”

This was never going to work.

If the johns were at just as much risk as she was, wouldn’t they be reluctant to give all this information over the phone? How would they know I wasn’t a cop?

I guessed if all they wanted to pay for was “an hour of time,” that wouldn’t become too big an issue.

How illegal was this? On a scale of 1 to 10, how likely was it that, if the cops came around asking questions, I would be arrested along with Caroline? This was probably a lot more illegal than pouring wine for a john or trying to scam lingerie stores.

Many businesses do illegal things all the time in an effort to get more work out of employees for less money. But this felt different than the time my boss at the movie theater told me to work overtime without pay.

Most of all, I worried that I’d book the wrong guy. Then Caroline would be at risk, and if she didn’t get hurt, arrested, or stiffed, she’d definitely get pissed at me.


Moral 92: If someone asks you to do something illegal, look at their motivations.


The next day, after running errands and enduring the suggestive leers of the manager at the corner store when I went to pick up an entire case of Reddi-Wip, I was walking through the little lobby of Caroline’s apartment building when the cell phone in my pocket rang. My heart went into overdrive. My palms began sweating. I put down the case of Reddi-Wip and fished the phone out of my pocket.

I pressed the glowing green button.

“This is Kira’s assistant,” I said. “Can you please hold for one moment?” Oh god, was that sexy enough?

“Uh. . .sure?” said the guy on the other end.

“Thank you,” I said. I held the phone away from my face and tried to figure out how to put it on hold. I couldn’t, so I just pressed my thumb over the speaker part.

I needed a moment to get myself together. This was very stressful for me. But Caroline had seemed kind of blasé about the whole arrangement.


Moral 93: For some people, it’s really not a big deal. Others freak out. (This applies to a lot of things. Like rollercoasters, eating sushi, and paid sex.)


In the absence of a training manual for booking quality johns, I had attempted to create a de-facto checklist of points a john must meet in order to book an appointment.

Caroline found this checklist hysterical.

He had to be polite.

He had to not ask outright about any services or sex acts he wanted. That signified a lack of understanding about the situation and disrespect for Caroline.

He had to not be pushy about getting to see Caroline at a certain time.

He had to be employed. Bonus points for a lot of business travel.

He had to have seen an escort before. I didn’t want to book a newbie.

He had to readily agree to the price I quoted and not haggle over the phone. That was tasteless. If he wanted to bargain, he could do it with Caroline in person.

He had to not ask questions about me personally.

He had to not try to get sexy on the phone with me.


Moral 94: Whatever you’re looking to acquire in life, it helps to have a set of guidelines for recognizing it.


I flipped hastily through my journal, trying to find the checklist, and geared up to talk to the john again. I just had to approach this like my last secretarial job—when I’d answered phones for the fiction writing department of my college. And I had to sound sexy. Caroline had been very clear on that point.

But I felt more ridiculous than sexy. The best I could do was mimic Alotta Fagina from Austin Powers. “Thank you for holding,” I said, panicking. I found the checklist, but had trouble focusing on it, processing our conversation, and sounding sexy at the same time.

“Uh, no problem, I guess. I’m uh, calling about, uh. . .the ad on—”

“Yes, the ad,” I said. I wanted to prevent him talking about the ad as much as I wanted to shorten this conversation (although it would’ve been helpful to know where he’d seen it). And as Caroline had told me. . .Control the conversation and don’t let anyone say anything illegal.


Moral 95: People appreciate it when they don’t have to confess to crimes.


“The ad’s been very populaar this week,” I said. Alotta Fagina sexy talk tip: Draw out all your adjectives in a suggestive way. “Were you considering booking an appointment sooon?”

“Yeah,” said the guy.

“Grreeaat!” Holy crap. “Have you seen Kira before?”

“Uh, no,” said the guy. He sounded nervous.

“Ohhh, so you’ll have a grreeaat time getting to know each other,” I said. “Have you ever spent an evening with an escort before?”

“Um, yeah. A couple months ago.”

“Okaaay, so Kira works in blocks of forty-five minutes. How many time blocks are you interested in booking, and when do you want them?”

“Uh, Thursday. Anytime Thursday. One block of time.”

“Okay, Thursday, that sounds grreeaat. How about four pm?”

“Uh yeah, sounds good.”

It was clear this guy wanted to get off the phone. So did I. But I couldn’t let either of us off the hook yet. I had to “screen him.” Make sure he wasn’t a cop and. . .stuff. I turned to my checklist.

I had to try to relax him, too. As Caroline said. . .They’re calling me for pleasure. That means no stress. You have to make them feel comfortable.

How could I do that when I was uncomfortable as hell? I tried to conjure my inner sexy Latin American woman in a hot tub. Anything but a nervous white girl in an apartment building lobby with sweaty palms and a case of Reddi-Wip at her feet.

“I know Kira’s going to be looking forward to seeing you,” I heard myself say. “Tell me a little about yourself? Where do you work?”

“Uh, Barnes and Noble,” he said.

“Oh, that sounds fuun. I love to read.”

“Me too,” said the guy.

“So does Kira.” I’d never seen Caroline read anything except the newspaper. Sometimes. “Maybe you could tell her about your faavorite new releases. She’ll be glad to get some recommendations from someone with expeerience.”

“Yeah, yeah,” said the guy. “Um, I mean. Whatever she wants, you know.”

I asked his name and how long he’d worked there. He said Barry, and four years. I asked whether he worked on the floor, or was in management. He was a store manager. I asked whether he lived in Chicago or came from out of town.

“Of course I live in Chicago,” he said. “I work at a store in Chicago.”


“Very true,” I said, trying to sound sexy despite the stupid. But I just couldn’t keep up the adjectives thing after that. “So the appointment’s going to be five hundred. Is that within your. . .price range?”

“Yeah,” the guy said. “Yeah that’s good.”

“Great,” I said. “I’m just going to need the best number to reach you at.”

He rattled off a number and I tried to write it down while squeezing the phone between my shoulder and ear and continuing to talk sexy. When I had the number and had told him Caroline’s address, I ended the call as soon as possible.


Moral 96: Get to the point, then get off the phone.


When I was stocking the Reddi-Wip in the fridge, I told Caroline about the appointment.

“Barnes and Noble!” Caroline said, and burst into laughter. “Leslie! What the hell were you thinking?”

“What do you mean?”

“He works at Barnes and Noble? Can he even afford me?”

“He said he could.”

Caroline sighed and looked at me like I was some cute but misshapen zoo creature. At least she was laughing instead of yelling. “Whatever. Call him back and tell him to bring some beer.”

Barry had the cash, and he brought the beer. But Caroline still took me off appointment booking duty.


Moral 97: If it wasn’t in the job description, don’t be shocked when your employee can’t do it.


This is an except from the author’s book, “Working Girl: Somewhat Moral Values I Learned from a Sex Worker.” You can find it on Amazon.

L. Marrick is an author, ghostwriter and suitcase entrepreneur, which is a hipster way of saying she travels and works from her laptop. She writes about archetypes, spirituality, and history at Mythraeum.com. Follow her on Twitter @LMarrick, and on Facebook.

© Leslie Hedrick 2015. The content of this article, except for quoted or linked source materials, is protected by copyright. Please contact the author at the above links to request usage.

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