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Artful escorting

Do you have an image of an escort? Twenty something, tawny hair, sleek but with mildly oversized breasts and slightly too loud make up? Or brunette and sultry with pouty lips and an attitude? Or a Vegas showgirl with impossibly long legs gone bad. Or Catherine Deneuve in Belle de Jour looking all blonde and French and bewildered?
All these images are right and all are equally wrong. There is no “typical” escort. In fact there is not even a typical escorting business. Some girls are purely service providers catering to hobbyists and hoping for great reviews, others are courtesans with a wealthy clientele who barely advertise much less solicit reviews. It is all about style and presentation and where a girl feels most comfortable. At the same time, an escort is in business and wherever she places herself on the escorting continuum has to create income.
by Hannah Jay
We looked for a few girls who were both committed to escorting but willing to create businesses which suited their distinct needs and styles. We have talked to half a dozen and each is a long way from typical. Here’s Jane.
Jane’s Way
“I live in San Francisco.” Jane told us over Skype. “Which is incredibly expensive if you want a halfway nice place. I make art for a living and I am becoming pretty successful. But I am just starting so “pretty successful” means I sell a piece once in a while and I get into group shows. Unlike a lot of the people I went to art school with I don’t, as the expression goes, come from money. Exactly the opposite in fact. I sometimes have to send my mum money.”
“OK, I can’t live with roommates – they get in the way of art making – and I have a pretty simple one bedroom apartment in a fairly decent neighbourhood. But it is so expensive. And the problem is that even if I got a job all that would happen is I would have less time to make art and still not enough money.”
“All of which I was telling to a friend of mine a few years ago and she, a bit sarcastically, said, “Well, you could escort.” We both laughed. Except I didn’t really. When I went back to my apartment and looked at the piece I was working on I realized that escorting might be a perfect solution. I went online and, wow, what a zoo! I was on a couple of pretty down market sites and I just could not imagine doing this sort of work or being that sort of girl. No offence but some of those girls were plain scary.”
I’m not scary. I’m all of five foot three with short boy cut hair and a very petite figure. I am, as my mother used to tell me, gamine which I swear is French for “boyish”. I spend most of my days in overalls and a t-shirt and a baseball cap covered in paint and glue. And I like doing that. Sure, I had a couple of more girly outfits but nothing at all which really was what I thought I should wear if I wanted to be an escort.
But I am nothing if not resourceful. If I was going to do this I was going to do it my way and that started with an ad saying, “Pretty 20 something girl needs advice and purchasing power of an older man. Getting ready to escort but I don’t have a thing to wear. Can you help?” I put in a selfie of me in my painting clothes. I kept my face out of the shot.
I put the ad up late on a Thursday night and went out to a movie. I was out for maybe four hours and I got 150 separate email response. Yes, several pictures of remarkably unattractive penises; but most of the emails were very nice. I took the ad down and got to work answering emails. What a lot of work.
Eventually I found four men who I thought would be fun to see and fun to shop with. A bit of back and forth on email was incredibly useful. One of them asked how I was “screening”. A term I was unfamiliar with. Believe it or not he walked me through checking out potential clients.
When I had looked at the other girls I barely noticed their rates and that was a question I was getting asked a lot. How much for how long? And did I? Then there were a list of activities. Lots of different activities most of which I had never heard of. What I did know was that I wanted to stay safe so I required a condom no matter what. But those guys were not what I was looking for to start out. I really did want to go out shopping with someone.
Larry was my first ever escort date. In his fifties, he was a lawyer from a big downtown firm where a friend of mine worked reception which made checking him out easy. What a nice man. He suggested we meet for coffee which we did.
“So are you sure you want to do this?” he asked.
I admitted I was not at all sure. “But I would love to have the free time and some money.”
He didn’t try and talk me out of escorting. Quite the opposite.
“Here’s the point. Escorting is just like any other service business. You have clients, you set a fee, you do the job. But, and it is a big but, you don’t have to accept every client and, if anything, being selective makes you seem more valuable. Your fees need to reflect two things: the quality of service and how you want to be seen in the market place. But your fees are also a signal to your potential clients.”
We talked about “activities” and Larry suggested I stick to the basics. “If you are looking for older, better off, clients you don’t want to suggest you’ll do practically anything. When they see an escort the sex is part of the experience; but it is a long way from the whole thing and, even with Viagra, acrobatics are not necessarily a turn on. If you do the basics with lots of enthusiasm most men will be thrilled.”
I actually asked him what he thought I should charge. “Well, I bill out at $900 an hour. I don’t see all of that of course, but that gives you a bit of an idea.”
“So, what, $500?” I asked.
“Try $750. It’s not the top of the league in San Francisco, but set a two hour minimum and you’ll do fine.”
Which is, more or less, what I did. Then we went shopping.
I was used to watching every penny. I have the feeling Larry hadn’t worried about less than a thousand dollars in years. But the funniest thing was that when we walked into the downtown Nordstrom – his pick – we were met by a personal shopper he arranged. Now I was wearing one of my “not an artist outfits” and this girl liked it. Nothing complicated, just a long grey cotton skirt, leggings and a white shirt on top of a tank top.
Larry was very smooth. I could see how he earned his money. “Jane would like to look a little less like an art student and a little more like a personal assistant to a venture capitalist. Day and evening, say three outfits for each. I’ll be back in an hour. And shoes, don’t forget shoes. And make sure you buy a couple of good garter belts Jane, I detest pantyhose.”
My personal shopper, who was named Amy, was very professional but she could not help but smile at the garter belts. Which Larry knew she would. “Dad” does not buy lingerie. We were off. Lots of lingerie, a pair of smart low heeled day shoes, a set of “once around the bed” Louboutins, and a pair of quite practical three inch heels.
“Do you want to stick with the boho thing or would you like to dress it up a bit?” asked my personal shopper. “What? How about boho by day, dressy past five?”
“Absolutely. You have nice legs so let’s do a couple of above the knee skirts for day time. Dresses for evening. A jacket or two. Is this one off or will you be shopping again?”
“I don’t know.” I said not knowing what Larry’s plans were.
“Looking at you and how “good” clothes fit you I suspect you’re going to be here quite often. So we won’t go over the top. And three of these items and two pairs of the shoes are on sale. Now, we just have time for Jean down on the Charlotte Tilbury counter for a little makeup and your delightful gentleman will not recognize you.” Off we went and ten minutes later I had a bag of cosmetics, an eyelash curler and cheekbones I never knew existed. “Now, a black tote bag and we’re done.”
“I wish we had time to have your hair cut but here is Harry’s card. Brilliant. And here is mine.” she said as we walked down the main aisle on the fashion floor. There was Larry standing surrounded by beautifully boxed and wrapped clothing, shoes, lingerie, stockings and I honestly don’t know what else.
“You look beautiful.” was all he said and, followed by three rather envious salesgirls we went out the door to an Uber SUV. Smart. The sales girls loaded up the back and we climbed in. Because, Uber, Larry didn’t have to tell the driver where to go.
“Now, I want to see everything you bought and the best way to do that is to enjoy a suite before dinner if that is alright with you. As it happens our firm’s suite is empty tonight so…”
And off we went. Just up the hill, which describes almost anywhere in San Francisco. Larry had an overnight bag and I had half of Nordstroms. My clever personal shopper had even put a pretty, if tiny, silk nightie/chemise in amidst the lingerie. We were whisked – which is how it is always put – to the lovely one bedroom suite.
It was the most natural thing in the world to model my new clothes. One outfit at a time starting with day wear with, of course, flashes of the carefully chosen lingerie, and moving to a scintillating little black dress which was ideal for cocktails which we proceeded to have in the suite.
“Room Service, or should I show you off?” asked Larry. “I think I’ll show you off. Don’t bother to change.” he said laughing. We went to the elevators and, to my surprise, went up, rather than down. Yes, rooftop dining with the city at our feet. I had the feeling Larry had done this before so I asked.
“Well, yes. But this is my first time with a girl who is doing this for the first time. But I think if you are going to escort you might as well start at the top. You are certainly pretty enough. And I thoroughly enjoyed being teased this afternoon. You are a flirt under that artist tomboy exterior.”
So that is where I started. Larry took a little Viagra with his brandy and, a short elevator ride away, I slipped out of my little black dress and into my chemise. All went as expected.
Larry left late. “I’ve extended checkout for you so enjoy the suite. I’ve ordered a suitcase for you as well and you can use my Uber account.” He gave me a fatherly peck on the cheek and as he did left a thick ivory envelope on the night table.
I lay in that vast bed with the perfectly crisp, only slightly rumpled, sheets surrounding me and I wondered what the heck I was doing. But I knew. The question was would I do it again?
I woke up, got packed and realized that my first adventure in the escorting trade had gone unbelievably well. Full on “Pretty Woman” which just does not happen. Except it did. Now, would it happen again? Just as I was wondering there was a knock on the door and a bellhop arrived with coffee, croissants, flowers and a note. “I am away for two weeks but will be calling on my return. Thank you, L.”
So, sipping my coffee, I realized that I had two weeks and two thousand dollars and a suitcase full of gorgeous new clothes. Rent was paid. I didn’t have to see anyone else and Larry would be back. Which was all good, but a part of me wanted to see if I could escort and one date, no matter how perfect, is not quite it.
I decided to get in touch with the other men on my short list. It turned out that each of the other men I had screened from that first escorting ad were all interested. Each was older and each was more than willing to play the escorting game my way.
Larry had suggested that I concentrate on developing a very discerning clientele. Older, well off, a bit fatherly, interested in very safe encounters with a very low volume girl. “You’ll make more money and the risks are removed.”
He was right. Instead of coming to escorting from a place where I was desperate for money – which I had been – I came to it as someone who was worth the price she asked her clients to pay. That simple reversal meant that all of a sudden I had the power in my escort dates.
That power began with the fact I screened very hard. Not only did I have to be able to establish a potential client’s identity and contact information, I also decided that I wanted to spend a bit of time on the phone or over coffee before accepting a new client. Yes, this did slow things down at first. But it meant I never saw anyone I was even slightly uncomfortable with.
My two hour minimum rule worked very well and so did my policy of not watching the clock at all. I went over time a few times but what is half an hour to ensure that a gentleman will be coming back again and again.
I realized that if I wanted to have time to make art I needed to be very disciplined about my escorting. I set a basic target of three dates a week which provided me with all the money I needed. I soon learned that most of my clients preferred to see me mid-week. And I discovered that my clients, for one reason or another, liked to see me in one of four or five good hotels. Plus, and this was a bit of a surprise, I had as many mid to late afternoon dates as I did evening encounters. All of which was just fine with me.
I have kept my advertising minimal. Once a month I place a small, discreet ad looking for “discerning gentlemen” and promising “an afternoon or evening of pleasure, laughter and conversation with a sophisticated, gamine, muse”. I have a small picture in black and white and my face remains in shadow. I don’t get quite the rush of business my first escort ad provoked but I usually find three or four gentlemen to add to my roster. Which is all I need really.
I am into my third year escorting. The business is running itself and I am usually booked a couple of weeks in advance. I could see more clients but I think it would get pretty difficult to deliver a really quality service if I saw more than a few a week. I have raised my rates however. Not for my existing clients, just for new clients and that keeps my income very healthy.
My way of escorting is not for everyone. I am lucky. I started very near the top. But I am also lucky because I escort to pay for my art and, because I can devote full time to my art, my work is getting better known and I am selling more.
Larry did indeed return and after our next encounter proposed an arrangement which we have to this day: he sees me twice a month at my normal rates, but with a bit of shopping thrown in and no clock at all. I swear we keep my personal shopper, Amy, in designer clothes just on her commissions. Larry is wonderful and so generous. He likes to tease me about being his mistress but, as he has never proposed an allowance, I tease him right back about not being able to make a commitment.
My own plan is to keep escorting for at least the next two or three years. For me the whole transformation from starving artist to courtesan in the space of an hour is amazing. Being “Jane” takes me entirely away from art for a few hours which I think is actually good for my work. Plus, because “Jane” has a fair bit of cash from escorting I don’t get into the whole self-pity thing which I don’t think is good for artists. The cash plus “Jane’s” persona gives me a lot of self-confidence.
It funny how often I see Jane’s clients at my gallery openings and group shows. Once I have known a client for a while I will tell him my art name – which is also not my real name – and it is pleasing to see the little red dots land on my work. My clients are becoming my patrons which is very close to perfect.
The story continues

Escort Agency Talk Original article found on skipthegames.com