Escorting the courtesan way

If you have to say you are classy you aren’t.” said Simone in a Skype interview. “At a certain level men actually pay attention and what they are paying attention to are all the cues women of a certain status scatter without even knowing it.”

We had seen Simone’s ad on an escorting website and were struck by how bold it was.

“Seem a Dream, Be Real” is, frankly, a bit over the top for an escort ad. And the rest of the copy was equally forthright. Words like “luxury”, “pampering”, “designer”, “executive” and “penthouse” all evoked an almost impossible standard. No prices were given in the ad or on Simone’s exquisitely modern website. Of course we had to arrange a call.

“I wrote my ad and had my website designed to set really high expectations. I use a very good fashion photographer for my pictures. I don’t quote prices because, frankly, as the man said about the yacht, “if you have to ask you can’t afford it.” said Simone.

We learned that she was twenty nine and had been in the business for four years. She is blonde, quite tall, “5’8” in my stockings but I never wear less than a three inch heel. I’m just a bit enhanced on top, B to a very full C and a narrow back, best $6000 I have ever spent. I work out and I manage to keep my waist tiny.”

“To be blunt, I escort for the money. And, to get the money without working long hours with guys who think a shower is an optional extra, you have to find a way to go up market. My way was to create “Simone” as a courtesan.”

“I suspect, if you asked them, most of my clients would not know what a “courtesan” was or how that tradition stretches back to the court of the Medici. Further in fact. They wouldn’t have a clue about Belle Époque Paris and the demimonde. Nor would they realize that the recently deceased Madame Claude sent her girls to the Crowned Heads of Europe and JFK. But I do.”

“A courtesan is about far more than a wonderful sexual encounter. Of course the bedroom is part of the experience; but it is like a pearl in a setting of diamonds. The setting illuminates and sets off the luster of the pearl.”

“I invented Simone. When I was in college I was a French Literature major – not a hugely in demand subject – and I read Proust and Balzac and Zola. On the one hand I was in love with fin de siecle Paris – Nana, Odette and all the other girls who understood the nexus of cash and beauty. On the other I am a modern girl. A bit of a minimalist.”

“In college I would, to use a rather unfortunate term, “sugar” a bit for a few luxuries. In my fourth year I also saw a few escorting clients referred to me by an agency. All of this was fine but, realistically, I could not see myself sugaring or escorting or both over the long term. The money was nice but, as the expression goes, you earned it.”

“One thing sugaring did give me was my breast enhancement. A rather pleasant man asked if I would like to have my perfectly nice breasts done at his expense. I thought about it and realized that, if I decided I wanted to escort seriously a cup size and a half would be worth literally hundreds of thousands of dollars. And I was right. If anything, I underestimated the male fixation on pretty, large, nicely shaped breasts.”

I have to admit I spent a lot of my fourth year researching and planning what I thought of as my courtesan persona. “Simone” emerged as a matter of careful calculation. I knew I did not want to work for an escort agency. I knew that I wanted to be in a large city. I researched which large city and realized that it came down to a choice between New York, Los Angeles, Chicago, San Francisco, Seattle, Washington, Miami or Dallas. The logic was pretty straightforward, I wanted a city where there were a lot of well to do men and where there would be some who were willing to pay for a premium service. Doing my research I found that there was no question that New York was the center of the courtesan universe but, and it was a big but, the rents and the competition were huge. The same seemed to be true of LA – all those actress wannabes – and Washington.

I was doing all my research online and, while I was looking at Craigslist for an apartment, I saw an ad for a nice, furnished place which directed me to AirBnB.com. Hello.

I had been thinking in terms of setting up my own, modern, gorgeous space and entertaining there. But, as I scanned through the AirBnB listings I realized that with a bit of planning and my impeccable credit rating – which I had been really careful to preserve through college – I could work in any of these cities. I am a smart girl, I know how to work Excel and I realized that, if I flew the cheap flights and booked AirBnB apartments, I could fly in and out of a city for a couple of days. At the rates I was planning on charging the cost of the flight and the accommodation would be easily covered by one date. What if I could book three?

This thought led to the realization that Simone really did need to be an exclusive sort of girl. Which, in turn, lead to the whole idea of offering more than a standard escorting date. Lots of escorts “tour” which is to say they go to a different city, rent a hotel room and see clients. I thought Simone should do more.

Part of her mystique is that I actually post my itinerary on my website. Potential clients who see it come to the natural conclusion that Simone must be very special indeed as she travels all over the country. Of course, I try to make sure their experience is extraordinary so my clients really do understand that courtesan level service is something wonderful.

I am actually based in a leafy suburb of Chicago – though I never entertain in my home. Chicago because it is pretty much the “hub” of air travel in the US. I have a pretty, modern, apartment twenty minutes from O’Hare in a little village. My neighbours, and it is a neighbourly town, think that I am a merchandising consultant who flies a lot.

Once I realized I could use planes and inexpensive but surprisingly “luxe” AirBnB accommodations I also realized that with the internet I could advertise easily and reasonably in a number of cities at once. Three or, max, four hour direct flight will get you anywhere in the continental US.

Interestingly, most of my clients like to book Thursday, Friday or Saturday. I honestly don’t know why but that is now the pattern of my life. I fly out on Thursday morning, fly back on Sunday. By booking three nights I often get a discount from the AirBnB host.

So that solved Simone’s logistics issues. It also, amusingly, eliminated any serious law enforcement questions. On average I will be in a particular city once every two months. I am rarely staying in the same location. The police have more important things to do than setting up a sting for a girl who will be gone the next day.

The fact I am on planes a lot and I never want to check baggage outbound – coming home is fine because if it is lost it usually is delivered to my door the next day – I developed a very minimalist, modern, look for my trips and my dates.

A man paying my rates wants a girl who looks “finished”. Which means Simone has developed a very sophisticated but easy look. I keep my hair quite long, men like long hair a lot. But I keep my hair up when I travel. I don’t spend a fortune on haircuts but I have a great gal I see twice a month who deep conditions and, if necessary, trims. One necessity is a brilliant aesthetician because plane rides are Hell on your skin. Weekly facial, mani/pedi…wax as needed.

Make-up? I travel with a day and a night lipstick, Tom Ford. Mascara, a smokey eye shadow palette, a set of really good false eyelashes for evening, a bit of concealer and I am pretty much done. If you look at the ladies in first class you’ll see a lot of very minimal make-up. I look carefully.

Clothes. Remember I am going to be away for three nights and I want nothing but carry on. I take three matched sets of lingerie, including good firm garter belts, stockings because men love stockings – I buy mine from Secrets in Lace, fully fashioned, often seamed – two full slips and a couple of Patricia Fieldwalker silk chemises for night wear. Always fully sewn bras with lots of lace detailing. Save the molded bras for t-shirts.

Outerwear is obviously location and season specific but two skirts, one a body con pencil skirt, one a wool or cotton full pleated skirt, a Diane von Furstenberg wrap dress and a couple of really crisp white shirts and a pretty cashmere sweater. I have lots of coats and I wear one onto the plane. Shoes? One pair of three and a half inch Louboutin pumps and a pair of Dior ballet flats. I wear a really nice pair of over the knee Steve Madden heeled black patent leather boots travelling anytime it is even a little cold out. They are just a bit intimidating which is useful in airports. Those are the basics.

Now, often, a client will want to take me somewhere special as part of the date and if that is the case I am delighted but usually insist that we meet earlier in the day so he can buy me a special dress for the evening. I never charge extra for drinks and dinner; but the dress is a given on a first encounter. Over the years I have collected a couple of dozen gorgeous designer pieces. And, of course, because I move from place to place, I can wear these dresses with other clients.

I always pack a pretty vibrator as clients are often enthralled at the sight of their courtesan warming up. Condoms, an old stocking or two for light bondage, my little riding crop, police grade handcuffs – I buy lube when I get to my destination because the TSA gets squirrelly about liquids on planes.

When I get to whichever city I am going to I always have at least five hours before my first date. I take an early flight. If necessary I touch base with the AirBnB host, get the key and then take a look at the space I’ve rented. Pictures are good but you need to see a place.

I try to find locations which are close to, but not on top of, shopping. Because a courtesan is about an entire experience, not just the escorting end. In most cities there are good places to buy cut flowers. I buy lots. One mingy little bouquet screams cheap, five or six? Magic. In a perfect world there is a Costco nearby so I can drop my bags and dash. Costco often has great flowers. It also has excellent cheese, good bread, decent wine, things like scallops in bacon or smoked salmon. Most AirBnB spaces have things like plates and utensils but they rarely have nice napkins. Costco does and it has candles as well. If I have to go anywhere more than walking distance, Uber black cars. That lets me track my ground transport expenses.

I have one business credit card with Airmiles. For taxes I deduct everything charged to that card, Uber, planes, AirBnB, shopping, make-up, hair, everything. Simple.

When I am booking dates in a particular city I am very clear about my requirements. I need to be able to verify identity for screening. I need a deposit on booking and for a first time client, a further deposit 72 hours before our time together. I am firm on price but not on time. My theory is that I charge enough that my clients should not have to worry a moment about how long they have been with me. If I have two dates on a particular day I will explain to my first client that I am engaged several hours later and I have never had a problem.

About half my courtesan dates involve going out for drinks or dinner or both. That gives the date a natural rhythm. I very much encourage clients to take me out and I have a very standard cover story in case we meet his wife’s best friend in the restaurant. I am always a consultant. Because I screen heavily I know what my client does and I can be very convincing on those rare occasions when it is necessary. I also try to make sure that if we are going out we go out early. It is one thing to see a man with a much younger woman at seven o’clock in a restaurant, it is a whole other thing at ten.

If possible, I like to arrange a date or two in the afternoons. I will suggest this to clients and am quite prepared to take a short – two hour – date. But I insist that they take me to lunch and for a little sightseeing. Not to mention shopping. That La Perla lingerie does not buy itself.

The essence of the courtesan experience as opposed to the escort encounter is that I work very hard at getting to know my clients and letting them get to know me. At root a courtesan is much closer to a mistress than she is to an escort. Yes, there are indeed consenting adult activities; but the success of the encounter rests on whether or not my client has actually enjoyed my company.

At every stage of the encounter, even in bed, I present myself very much as a lady. I carry a nice, but not crazy expensive, bag. I wear good, real, jewelry and not too much. I am, if I do say so myself, a good conversationalist but, more importantly, a brilliant listener. I know a date is going well when my client argues with me or opens up about his work or his personal life. At the same time, I can make small talk pretty much forever.

When I started, four years ago, I was a little scared being out on my own in strange cities with strange men. Now it is all routine. I even add resort locations to have a bit of a break in the winter. Chicago is not lovely in February.

The biggest change in my business is that I now have regulars in each of the cities I visit. Instead of hoping to have three dates to make the trip profitable, I usually have three regulars who will book my time as soon as they know I am coming to town. Makes everything much nicer. And some of those regulars will book a weekend a couple of times a year somewhere we can play without having to keep an eye out for business acquaintances or that nice soccer mom from Tim’s school team. Those dates are fun and very lucrative.

The one thing which is tough is staying healthy with all the flying. Where I live there is a great community center and indoor swimming pool. I hit the gym and I try to swim every second day I am home. That helps. So does taking one week a month off. Because I can now be pretty certain to get three if not six dates in each city I travel to, I can afford the downtime.

The point of being a courtesan rather than an escort is I have to make sure I am up for every date. My clients expect a remarkable level of service and I aim to give them just what they want. A few of them want to explore kinkier things and with regulars, to a point, I am up for that. But many of my clients really just want a few hours with a perfectly put together, intelligent, girl who hangs on their every word and just can’t wait to get to bed. It doesn’t matter if they are thirty or seventy – and I have clients in between those ages – most men get a terrific boost out of simply enjoying my company knowing it will end in consenting adult activity.

I plan to keep doing this for at least the next few years. The funny thing is that flying as much as I do I meet a lot of people, men and women, in business. I stick with my merchandizing consultant story and I am amazed at how many people want my card. A year ago I began taking courses on merchandizing and I actually really like the whole thing. Particularly with fashion.

In two weeks I am starting an internship at a pretty interesting fashion forward design and manufacturing house in Chicago. They were willing to work around my schedule and we’ll see where that goes.

Obviously there comes a time where a girl doesn’t want to be living on airplanes behind a cover story. I have to admit I have been tempted a few times to tell people when they ask what I do that “I am a multi-city, AirBnb courtesan, and you?” But I have resisted temptation. I like my work, my nest egg and my privacy. At the same time, I can see transitioning to working for a fashion company in merchandising or even sales. I am already flying around the country, why not look for some sales?