Escorting the powers that be

“I am not at all an ultra high end girl.” said Jenny in our Skype call. “And my clients are not billionaires. They work for billionaires and they are certainly not hurting for money; but they are in a different niche.”

Escorting is a business about stratification. Super elite girls are more like models than the conventional picture of an escort. In fact, a fair number of the international courtesan set either are or have been exactly that, models.

by Hannah Jay

“Part of my business is going to parties with one or another of my clients. You can spot the girls. The impossibly high cheek boned Russians wearing head to toe couture. And California girls too pretty to be porn stars. There is a circuit and you see the same girls. But it is not my circuit.”

“There are places in America, in England and in France where the rule is that a lady’s name appears in the newspaper only three times in her life: birth, marriage, death. These are places where the kids all have trusts set up by robber baron great grandparents and money is never spoken of because if you are there, you have enough.

It is a funny world because people are born into it, lead lives which outwardly conform to the expectations of that world and, most importantly, stay married. No matter what. A lot of the people in this world are related to each other and a lot of them are in business together, or they serve on the same Boards or their wives work for the same charities. It is very enclosed, very quiet.

At the same time, there is a sort of unspoken agreement that so long as a man is discreet he is more than welcome to make arrangements with the right sort of girl. The big question is what sort, the right sort, is.

Which brings me around to my story. I didn’t grow up in this world at all. Basically I grew up in a suburb of a not very glamorous city in the mid-west and I couldn’t wait to get away to college. Off I went to a good school in Boston. No, not Harvard. Which was lucky as it turns out. In my junior year I spent a bit of time working on a project which meant I had to spend a bit of time researching in a library which one of the big consultancies kept at its downtown head office. I was doing a history degree and this library had, for some reason, a lot of material on certain 19th century tycoons. I had a visitor’s pass and one night, after I finished taking my notes, I was walking to the elevator and I heard what sounded like a party going on in one of the offices. A guy comes out, he’d had a few drinks and he yelled “You can’t go home yet, we’re just getting started.”

I had no idea what was going on but he was a good looking guy in his mid thirties. Sort of a mildly blown out preppy. Probably played lacrosse at Choate or something. Anyway he introduced himself as Charles, “But my friends call me Chas” and took me back into the office where there were two other girls and four guys celebrating some sort of deal. It was actually quite fun and we went out for a really good dinner a bit later. Living on a student budget restaurants, leave aside really good restaurants were not something I was used to.

The other two girls were very attractive, dressed nicely and were friendly. We excused ourselves for the powder room – no really, that was what was on the door – and one of them said, “So how long have you been working.” I completely missed it and started telling them about doing my research. They let me prattle on and we rejoined the party. We finished dinner and over coffee one of the men who I had been talking to leaned in and asked, “So, what are you charging for later?” Again, I really had no idea and I brushed him off. The two girls left, one with the man who had asked me about later the other with the other two men leaving me with Chas. He was actually rather sweet and he apologized for thinking I was one of the girls. Which left me no wiser. So he spelled it out. The two girls were escorts and he thought I was too.

You know how there are moments in your life where you make a sudden choice. Well I did right then, I said, “How do you know I’m not?” He said, “You are?” And I said “Very occasionally and I am very expensive.” And that, as the saying goes, is how a nice girl like me got into a business like this.

It turns out that the two girls who had been at the party had been sent by an agency and Chas didn’t like that at all. “Just about all my work is done with bankers and lawyers and politicians who can’t be too careful. Once you bring an agency in who knows who will have your contact details and your email. But, for the right girl, if she was very quiet about it, there is a lot of work. A lot.”

I left the very pleasant hotel he’d booked us into the next morning with a purse full of cash and Chas’s private number. He had told me that once I had a business phone he’d be happy to share that number with a few of his friends. I got the phone and that was exactly what Chas did.

We met again a couple of weeks later and he said the three friends he had referred all thought I was a lovely girl and would be calling again. He also suggested that I set up a members only website and have a few business cards printed. All word of mouth.

I did exactly that and kept working on this basis right through to the end of my senior year. But then I had to make another choice: did I want to keep going or would I stop escorting when I graduated? I was pretty sure I could make a very good living escorting, just seeing the men Chas referred and the men that they in turn referred, was a very good living.

The only problem I could see is that it was a bit too exclusive. I was relying upon a very small group of men for my entire income. What if they got bored? What if they moved on? So I decided to expand my horizons a little. I did this with a few very discreet ads. Very upmarket, entirely focused on the New York, Boston, Philadelphia, Washington markets.

“Ultra discreet Gentleman’s companion. When only the best will do.”

To that point I had not really worried much about the age of my clients but I thought I should restrict the market a bit by saying “Over 50 preferred” and I also restricted it a bit more by saying “outcalls to executive hotels only”. I figured that this would give me a bit of diversification without causing much stir.

Was I ever wrong. I put the ads up and a day later my private phone rang with a very annoyed Chas on the line. One of his friends had seen my escorting ad, gone to my website and realized that I was the girl Chas had introduced him to. He was not happy and, of course, as he was one of Chas’s more important clients, Chas was not happy.

“Don’t get greedy, Jenny. If you want more clients just tell me. If you are advertising do it under a totally different name with a different website and I don’t want to hear about it.”

He invited me for a drink. The thing about these sorts of people is that they can be entirely furious but it never shows on their face. It was a revealing conversation.

“Do you know what makes you a perfect escort? I’ll tell you. No one has any idea you are an escort. If you keep it that way and work based on referrals you’ll be safer and far better off. The men you are seeing don’t care what you charge as long as it never shows up as a wire transfer or a credit card charge. You’ve taken care of that. You have no law enforcement profile. And, between you and I, you have no security profile to speak of other than a bit which rubs off from a few of your clients.

Now, it is up to you if you want to step out into the bigger world. I won’t stop you but, seriously, think about it. You have a very good reputation with my sort of people. And there are a lot of my sort of people.”

I didn’t really need to think about it. I pulled my ads and changed my website so it was entirely members only. And Chas was true to his word. He referred a few more clients in Boston but he also took me to New York. We had a lovely time, I was well paid and he arranged for me to meet a half a dozen of his pals from prep school. Nice guys, mainly law and investment banking. We went for drinks or lunch with Chas acting as the perfect host. Not a word about my business. But all of them took my card and gave me safe email addresses to let them know when I was next in New York.

As I said earlier, it is a network. Prep schools, Ivies, banking, law, government work. I am pretty sure at least one of my New York clients works for some sort of intelligence group. They’ve come up together and they trust each other. Most of them are married, some more than once; but it seems to be part of the deal that they “work hard and they play hard”.

Of course most of my dates are pretty similar. I will book anything from two hours to a full evening. If it is an evening we will nearly always have dinner. I intuited that this group of clients wants me to look a certain way. Which is funny because it is all about the sort of sexiness that only a really discerning eye will spot. Really. On the one side these men don’t want you to look like an office drone; but, on the other, they really don’t want you to wear a skirt up to there or a top which is deeply revealing.

What they do want is good company and a girl who is interested in whatever it is they want to talk about. Yes, they will want to spend some quality consenting adult time and I aim to please; but I think what they really want is a girl they can talk to, confidentially, who is not part of their world. And Chas was right, they really don’t care what it costs.

I am very business like. I have my rates and I stick to them. But the tips are amazing. Especially on second encounters. When I see one of these men for the first time they are really just trying me out. But once they are comfortable with me they actually seem to prefer spending more rather than less. I expect that is partly because they have a lot of money but one of my clients put it a bit differently. We were having a drink before dinner in one of those crusty old mahogany and silver bars and he said,

“My grandfather kept an actress as his mistress for nearly twenty years back before WWII. The whole nine yards. Great apartment, charge accounts at all the good stores. She was a secret from his family but all his business associates knew. And most of them kept similar girls. To do that on that sort of scale today would be a million dollar a year proposition. Plus, even if you could afford it, you’d run the risk of making the papers. Just not worth it. And where would you find “an actress” you could trust? And I’d have the same problem with an escort if I didn’t have some sort of reference. Too risky. What you do Jenny is de-risk the encounter.”

I liked that. De-risking sounds like a good thing. Part of my de-risking is that I can be seen pretty much anywhere these guys go. The downtown bars and restaurants are one thing, the receptions and cocktail parties are quite another. With so many more women in the workforce these business/social activities can be a minefield if you don’t have your story straight. If you are with an escorting client it is important to have a simple, bullet proof, cover ready to go when a woman he works with and who probably knows his wife starts, in the nicest possible way, to “get to know you”.

Again, this is a network. These people went to the same schools and the same universities and they are working together. So, first rule, don’t have any connections they can trace. Which is why not going to Harvard is a good thing. That is a very small world. So I have a simple story about being a freelance researcher based in Boston but travelling a lot to New York and Washington. I want to put the travel in simply because the next time I see a person it might well be at the same sort of reception but in a different city. If asked my research is confidential and I am more than happy to leave the impression that there is some government connection. But my business card says nothing more than my name and “historical research”. Which is, as it happens what I am actually doing in my off hours, I am working on a book about tycoon’s restaurants in the age of the Robber Barons.

The other thing about escorting in this group of men is that they are themselves both incredibly discreet and very, very confident. I’ve been in several social situations where I am working as an escort and I run into one of my clients. This might be awkward with other sorts of clients but with these guys it’s actually somewhat fun. Because I am only known as Jenny to all these men it is no big deal for a guy I’d seen the week before to come over and say hi. And because I do talk about my research work with my clients we always have something to chat about.

Obviously I don’t talk about my clients’ consenting adult activities but, frankly, it is all pretty normal. I do get the occasional special request but that mainly for spicy bits of lingerie and I have two wonderful shoe fetishists where the dates always start buying a really nice pair of heels. One of them can never make his mind up on colour so buys two pairs.

I know escorts just love regulars and I have lots of regulars. But with this group of men it is not any particular client who is a regular, it is the whole group in three different cities. It wouldn’t be fair to say they are interchangeable; but they are really very similar.

I’ve been doing this now for a little less than four years. My book is almost finished and then I am not entirely sure what I will do. The truth is that I am young enough that I could keep doing this for five or ten years and really make a lot of money. Which would be fun. I’ve just been socking most of the escorting money away, even paying tax on it. Plus, once in a while, one of my clients will give me an investment tip. There is no surer thing. I have a nice but not luxurious apartment where I never see clients. “Jenny” has a life completely separate from mine.

The one thing which these guys seem to have in common is that they prefer a very understated life. They wear suits which have buttoned cuffs. The buttons actually work on the sleeves. It is a detail that no one can detect. But it matters a lot to them. Many of them have their shoes handmade in London. Again, something you really can’t tell at a distance. They wear wonderful, old, very plain watches which may cost a fortune but look very ordinary. Which is the secret of my success I guess. “Jenny” makes a point of being very expensive, attractive, subtle and very, very understated. A pretty young girl making her way in the world who happens to know more than her fair share of America’s unacknowledged ruling class. That I am paid for my company is not something which is any of anybody’s business. Which is how I like it and how my clients prefer to leave it. It works for me.