Working Girl: It’s OK to be Awkward when Talking to a John

Just a Regular Working Girl: Moralistic Values Gleaned from My Time in Chicago’s Seedy Underworld

Moral #19: It’s OK to be Awkward when Talking to a John


Just drink the wine.Image by willia4 at Flickr Commons.

Just drink the wine.
Image by willia4 at Flickr Commons.

If you’re not following this series, A) why the hell not? B) here’s a quick recap: My boss Caroline was an escort and I was her personal assistant.

She used to send me out shopping or running errands when she was with clients. This is the story of one of those times . . .


The first thing that struck me about Caroline’s clients—and this took me awhile to get over—was how much they resembled my dad’s friends.

I don’t know what I expected, but they were just regular businessmen. Non-descript suits, bad ties, scuffed Johnston & Murphy shoes. Thinning hair, a little overweight, sometimes a little tired-looking. Most of them were married. Almost all of them were polite.

Caroline would shove a shopping list in my hand. “Go to Jewel, get this stuff. Be back in 45 minutes,” she would say, and shoo me out the door.

But this time, her client was running a little early and called to give her a heads up.

On the phone, her voice was deep and sultry, slow and textured. “Great,” she said, and I couldn’t believe guys actually liked that. It sounded like such fake sexy—like porn sexy—and they already knew they were paying her. It wasn’t like she was convincing them of anything. “See you in a couple minutes.”

Then she hung up and turned to me. “Shit! I’m not ready! I’m not ready!”

“Okay,” I said, ever helpful. “What do you want me to do?”

I’d already lit the candles (Yankee Candles, the sexiest candles in the mall) and straightened the bed and cleaned up all evidence that someone lived there who liked to eat candy in bed and throw the wrappers in the general direction of the trash can in the corner.


Moral #17: Everyone’s putting on a show. A big, shiny, sexy show.


And big candles in jars that smell like apple-cinnamon are the perfect sexy lighting.Image by Neil Conway at Flickr Commons.

And big candles in jars are the perfect sexy lighting.
Image by Neil Conway at Flickr Commons.

(Caroline kept two big shopping bags in the tight space between her bed and the wall. One was full of candy. The other was full of condoms. It was my job to keep both full, and to go through and get rid of anything that looked expired.)

“I have to rinse off in the shower and get dressed!” Caroline said. “You answer the door when he gets here and let him in!”

“You’re just going to let him hang out while you get ready?” I asked.

“Don’t be stupid! You keep him entertained!”

“Me?” I said. I began to feel as though I had swallowed a hamster and it was running circles around in my belly.

“Pour him some wine!”

“I don’t drink,” I said. I was 20, and drinking was against the law. So was aiding and abetting prostitution, probably, but that didn’t bother me so much.


Moral #18: Just because I don’t drink doesn’t mean I’m not abetting a prostitute.

We pick and choose which rules to break.


“Well you know how to pour wine, don’t you? Goddamn it!”

“But what do you want me to say to him?”

“OH MY GOD!” she said. “HE’S JUST A DUDE! And you’re a cute girl, and he’s about to get laid! I promise this will be an easy conversation! Talk about the goddamn weather if you want! Just keep him entertained!”

These instructions issued, Caroline thundered up her spiral staircase. “And remember my name is Kira!” she shouted over her second-floor balcony. “And smile!” Then I heard the shower turn on.

Not thirty seconds later, there was a knock on the door.

Crap, I thought. Before I could think anything else or start to freak out, I answered the door. And smiled.

Caroline’s client looked just like one of my dad’s friends. Not any particular friend—just like he’d fit in their group pretty easily. He was tall and trim, with salt and pepper hair and gentle lines around his eyes.

“Hi,” I said. I used “secretary voice,” which wasn’t as sexy as Caroline’s porn sex voice. “Secretary voice” is what you hear on health insurance commercials. Not phone sex lines. “You must be David,” Secretary Leslie said.

“I am David,” he said, with an interested and slightly amused smile. I was surprised by his British accent.

“Please, come in,” I said. “I’m Kira’s assistant. Kira’s just freshening up. She’ll be down in a minute.” I was proud of myself for remembering Caroline’s fake name and saying things that sounded sane, when I was face-to-face with an amused British john.

Before I go any further, I should tell you that I have a thing for British guys. It’s because I’m obsessed with ancient British history and the Arthurian Legend. I can’t say whether the fascination came from my studies, or my studies came from my fascination. Either way, there you have it.

And there was David, whose accent took him right out of the realm of my dad’s friends.

Okay, I thought, he’s just a dude. (A British dude paying for sex from my boss.) Smile. Talk about the weather.

I asked what he was in the US for (business, of course), and where in the UK he was from.

“Devon,” he said. “Around Exeter. I’m sure you don’t know where that is.”

“I do, actually,” I said.

At least this gave us something to talk about. David, as luck (or some sadistic god who orchestrates these situations) would have it, was a history buff. So we talked about the Roman occupation of Britain.

Then I remembered the wine. Give me five minutes with a john before one paid sex rendezvous, and all my polite party hosting skills go right out the window.

And, apparently, all my wine bottle opening skills. Caroline’s bottle opener was a corkscrew with no lever.

Nooooo!!!!Image by Svadilfari at Flickr Commons

Image by Svadilfari at Flickr Commons

At first I pretended everything was cool, and that I would be able to do it with just a little extra effort. But when my comments about the Romano-British tin mining industry were interrupted with fierce grunts, and then I tried to hold the bottle between my knees and use two hands on the corkscrew, it was clear no amount of effort on my part would be enough.

David, who wasn’t even bothering to hide his amusement anymore, wound up opening the wine. At this point, I decided his amusement was a good thing. I could handle the role of the blushing blonde girl who needed to be saved from opening a bottle of wine. That’s what I was, right? And maybe it would make him feel strong and necessary or something.


Moral #19: It’s OK to be awkward when talking to a john.

Even big shiny sexy shows have room for awkwardness. (That’s called charm, or something.)


Then he offered to pour me a glass.

“Oh no,” I said. “Thanks. I don’t drink.”

His brows raised and he laughed again. “No drinking on the job, is it?”

“Well, there’s that. But I don’t drink anyway.”

“I won’t tell,” David said. This was a man who truly enjoyed secret fun times.

“No, thanks,” I said.


I shrugged.

“Hm,” he said. “I suppose that should have been apparent when you had trouble with the bottle.”

I felt myself turn bright red and David said, “Oh, I’m kidding!” He sipped the wine and said, “So how long have you worked with Kira?”

“Three months,” I said.

“Ah,” he said. “And is she training you for anything more than serving wine? Because that’s not going very well.”

“No,” I said, laughing. “I’m just her assistant.”

“Hm,” he said, a knowing twinkle in his eyes.

I was feeling more comfortable now, for some reason. It was probably our shared interest in history, combined with the horrifying humiliation of the wine incident, that broke the ice. “I don’t even drink!” I said.

“Hm,” he said again. He eyed me up and down.

At that point, Caroline descended the spiral staircase dramatically, like a slutty princess coming to greet her pimpin’ prince. She wore silver lamé short shorts, glittery stilettos, and a black corset.


It was like Jasmine and Aladdin except not at all.Image by Ewen and Donabel at Flickr Commons.

It was like Jasmine and Aladdin except not at all.
Image by Ewen and Donabel at Flickr Commons.

I could finally get out of there. I said a prayer of resentful thanks to that sadistic god who organized this debacle.

“Hi,” she said to David. “It’s been awhile, huh?”

“Too long,” David said. He was a repeat client. He liked history. “Oh, Leslie,” he said, before they went upstairs. He eyed me again. “If you change your mind and decide to get a little more adventurous, have Kira give me a call.”

“Thanks,” I said. “I, uh . . . will. Remember that.”

After they went upstairs, I drank the whole rest of David’s glass without thinking about it, and left quietly to run Caroline’s errands.


Moral #20: Sometimes it’s OK to drink on the job.



L. Marrick is a historical fantasy writer and freelance copywriter. She waxes poetic about swords and the Renaissance Faire at her author blog. She looks all professional-like at her copywriting site. She eats too much chocolate and still doesn’t believe downward dog is supposed to be a restful yoga pose. You can connect with her at either of her websites, and follow her on Twitter @LMarrick.

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