How to be a companion who escorts hedgies

“As far as I am concerned I think if you are going to escort you should aim to make the most money you can as easily as you can. And that means lots of well off clients.” said Rachel in our call.

We’d found Rachel via a referral from another escort who worked in Boston. This girl told us, “I think Rachel is the smartest escort I’ve ever met. She has the whole thing figured out and you should talk to her.”

Talking to Rachel is not all that straight forward. While she advertises her services online, all of her communication is carried on through her escorting website. So we wrote. And got no answer. We asked our friend in Boston to see if she could persuade Rachel to have a chat. That did the trick.

by Hannah Jay

“I don’t really talk about my business.” said Rachel. “I mean I am an escort. I don’t pretend to be anything else. I sleep with men for money.”

We told her that her escort friend in Boston said she was “the smartest escort” she’d ever met.

“I am not so smart. But I am pretty good at figuring things out. I always begin any project by making a list of the questions I think will make a difference. With escorting the questions I came up with were: #1 what does a successful escort need?

The short answer to that question is a lot of well to do clients. Because there is no point being an escort for small money. Total waste of time really. And way too risky. The more money an escorting client is prepared to spend the less likely he is to be dangerous. Which is not to say wealthy men don’t have their little peccadillos and fetishes and obsessions – thank goodness because that is where the real money is, but I’ll get to that.

The point is that the wealthier your escorting clients the fewer problems you are likely to have and the more money you are likely to make.

Question #2 was a little more interesting. Where are all these wealthy men? Now the obvious answers – New York, Los Angeles, San Jose – think Silicon Valley – San Francisco, Seattle, Dallas, Boston, Palm Beach are all true. But every one of these cities and the others which come to mind have big downsides for an escort. Law Enforcement and competition are the biggest. Yes, usually law enforcement is focused on those poor girls on the street or advertising the $40 blow jobs; but in every major city there will be ambitious cops who will decide they want to take down a few high end girls. No thank you.

Competition is the other huge factor. In places like New York and San Jose and LA you have beautiful girls from all over the world chasing a limited number of rich guys who like escorts. Sure, the escorting rates in those big cities can be huge; but the number of girls working is also huge. Plus you have the “models” and the actresses who are part timing.

When I was looking at setting up my escorting business I quickly realized that the “obvious” place to run the business was not in a big, flashy, city with high rents and huge competition. Which lead to Question #3: If not New York or LA or Seattle then where?

Answering that question took a bit of research. Which was fine because I actually did a lot of research when I was doing my undergraduate degree.

And, I know you are dying to ask. I did go to a private college – I won’t say where – and yes, I did do a little sugaring and escorting in college but really just because I liked to have a fair bit of extra money and it was just so easy to put up a sugar ad or a one off escorting ad. But I really did not see what I was doing in college as a business. That came just a bit later. Which we can talk about.

The trick to setting up a research project is to ask the right question: in this case, where are there concentrations of well to do men? In the summer the year I graduated from college I set about finding out where these guys actually lived. Google is your friend and it was fascinating. Pay attention to Charles Murray’s great book, Coming Apart. Look for the Super Zips. I was living in the Boston area at the time and, given the choice, I really wanted to stay in the North East. But I did fly out to the West Coast to see Silicon Valley up close. No doubt at all that there was a lot of money along Sand Hill Road and I remember reading a great description in USA Today, “Silicon Valley is like a military base: There are very few civilian women and lots of money,” said one Silicon Valley entrepreneur who spoke on the condition of anonymity because of the sensitive nature of the topic.”

Well, yes. The trouble was that the whole Silicon Valley area is stupid expensive to live in and there were a lot of girls who had the same idea. Plus, the San Jose police spent a ridiculous amount of their time trying to catch escorts both in the hotels and bars around Silicon Valley and online. I spent a couple of days there and then up in San Francisco and I realized that while there was a lot of money to be made, the risk reward ratio and the competition from other escorts made the whole place unattractive.

The other thing was I am just not that interested in nerds. I don’t play online games, I find Game of Thrones as unwatchable as the books were unreadable, I know how to use a computer but I don’t love my computer. Escorting is a funny business. You may not love all your clients but it sure helps if you like them or can find something in common with them. I didn’t have anything in common with the guys I met while I was in the Valley and I was not even working.

I looked at a few other areas but they all seemed to have more negatives than positives. My objective for my escorting business was to make and save as much money as possible. You don’t save money in a big city. The rents are too high and everything you do is expensive. So what I really wanted to find was a concentration of wealthy men somewhere I could get a great space for nearly no money.


It would be if you didn’t do your research. Do you know where the greatest concentration of hedge fund headquarters are in America? You might think New York and you would be close; but, in fact, all those financial engineers can do the math and they don’t like commuting so they started setting up shop in Fairfield County Connecticut. Which is the county closest to New York City and one of the wealthiest counties in the US. It has direct commuter connections to New York City – which is fun and useful for business.

I drove down from Boston. Taking the freeway it is an easy three hour drive. I booked an AirBnB room in the little town of Fairfield itself. Charming and just bursting with money. I spent a few days there just driving around and looking at apartments – pretty dire – and, to my surprise, houses. Here is the strange thing about a place like Fairfield County; there are lots of multi-million dollar houses and fifty million dollar estates, but there are also a lot of very private, out of the way houses, gate houses, boat houses and other small buildings which have been fixed up and then, in many cases, never used. I had not really thought about the potential of a house for an escort business but when I saw a really pretty little white clapboard house on the back of a lakeside property which had originally been the maids’ quarters I got to thinking very hard indeed. I rented it.

So Question #4: what were all those wealthy men wandering around Fairfield looking for in an escort?

When I first started sugaring and escorting in college I had a very simple routine. I knew my clients were looking for sex with a college girl and that is exactly what they got. I didn’t have many daddies and I didn’t see many escorting clients, but I saw enough to realize that there was probably a lot more a girl could do than just a quick blow job or twenty minutes between the sheets. But as I was really doing the college girl escort thing as a bit of a thrill, a hobby, I never went much further. Now I really wanted to figure it out.

My little house had three bedrooms, a very pleasant sitting room, a dining room and a kitchen. It had a small fenced yard and I had run of the 30 acre estate which surrounded the main house. The owners, a lovely older couple, were just fine with my story that I was trying to finish a book I had started in college and actually reduced my rent in exchange for my going up to check on the main house every day when they were away. My maid’s house was invisible to the main house and had a hundred yard gravel road coming in off a secondary road. It was private, not to say isolated. Which suited me. It was also partially furnished and the owners, who had a lot of everything, suggested I might like to take a look at some of the furniture they had in one of the out buildings. It was wonderful. Lovely old fashioned chintzes and nice, real, 19th century landscape paintings. It was easy to furnish the house in a certain style.

The thing I learned being a college girl escort is that men seem to like seeing girls who remind them of who they were in college. Girls like the woman they married but young enough to be their daughters. My suspicion was that there was good money to be made simply by recreating the world as it was twenty or thirty years ago.

Which lead to Question #5: which world? Thirty years back there was a pretty firm distinction between good girls – like their wives and daughters – and naughty girls who might be in the escorting business. Which side of that line did I want to be on? Or should I just offer the GFE and go with that?

It was not an easy question without data and the only way to collect data was to actually advertise and see what happened. I decided to try the good girl vibe. In a way it really was the only way to escort in Fairfield County because, if you walked down the street, they were all good girls. The younger women were nicely dressed and carrying Kate Spade or Tory Burch bags, the older women were really well dressed and carrying Hermes and Dior bags.

So I fitted in. There is no reason an escort has to dress like some sort of sex bomb – pretty lingerie is more than sufficient. My advertising and my website were all about a sort of naughty preppie girl who, in a temporary lapse of judgement, decides to give escorting a whirl. All with a hugely arch sense of humour. I even made a few hedge fund jokes.

Question #6 is the age old problem of what to charge. Charming as it is to say “as much as possible” the fact is that escorts have to set their rates according to the market they are in. But Fairfield County is basically a bedroom community for downtown Manhattan and a lot of the businesses in the area could just as easily be on Wall Street. New York escorts, who are almost always booked through agencies at the upper end, charge more for their time than escorts anywhere in the country. Which meant the men in my little market were used to paying top dollar. The problem was that the local girls seemed to think $400 an hour was top dollar.

For the hedge fund guys I wanted as clients, $400 was what they might spend on a tie. Just as importantly, setting a high price, but one which was lower than the agency prices in New York, meant I was signaling I was not like the other girls. It was a high risk, high reward strategy I thought would make my escorting business stand out for the right reasons.

I also decided to only do in-calls for first time clients. I loved my little house and I had decorated it in a very warm, very welcoming way. Because the house is very private we can enjoy ourselves pretty much anywhere which is great fun on those hot summer afternoons. I dress seasonally, pretty cotton dresses, usually front buttoning, in the spring and summer, knits, also front buttoning, in the fall and winter. But I will also just wear jeans and a sweater.

Hair and makeup are miles away from the more standard escort fare of slightly over the top. For day I wear a little lipstick and a bit of mascara, evenings some light eye shadow and a tiny hint of a bronzing foundation to set off my cheekbones. The lipstick is a little redder. I have my hair in a short, rather clever, bob which I can slick back if the client likes a bit of a dramatic, boyish, look but usually it is just wash and wear straight from the shower. No perfume. No scented anything.

My clients have a certain pattern. Saturday and Sunday afternoons are almost always booked with a client coming over for the length of a round of golf. We’ll usually have lunch and then adjourn to my really very sweet, very French country style, bedroom. I also see quite a few men between four and seven weekdays. They leave New York a little early and arrive home a little late. I do, at most three evening dates a week.

In an average week I will see between seven and ten clients. No rush. I charge by the date rather than the hour and most of the dates are a couple of hours long.

As I hoped, my advertising and website appeal to very affluent men. I joke about being a hooker to the hedgies but that is not far wrong. At least half my clients are in the hedge fund business. Which is great because, while they will buy their wives a Birkin to celebrate a killing, they will buy themselves an evening or two with me. Although one sweet man got confused and bought a Birkin for his wife and a Kelly for me. I know which Birkin he got her and I have seen her carrying it.

So, question, #7 as I recall – what do these wealthy men like? Well while there are certainly some hedgies with a few kinks – I have a nice selection of toys and strap-ons in a few, moderate, sizes – most are really looking for the thrill of a slightly illicit time with a girl they can trust completely. I stress discretion and my clients very much appreciate that.

Back in John Cheever and John Updike’s day these men would probably be having affairs with their secretaries or with the wife of a friend. Men who make 100 million dollar bets for a living tend to have very high sex drives but they also tend to marry smart, rather sexless, women. Perfectly turned out but sort of dry, brittle. My escorting world reminds them of the girls they enjoyed in college but, mainly for social reasons, never really thought of marrying.

I am very much prim and proper walking down the street in Fairfield or Southport. I look very much like my clients wonderfully polished daughters. After all, I went to the same sort of school and the same sort of college they do.

I don’t think my escorting clients have an incest fantasy going. Not specifically. It’s more about a sense of wanting the attentions of a pretty, well mannered, young girl who is delighted to accommodate their rutty desires in exchange for the one thing they have far too much of: money.

Which, of course, leads to question #8, how long will I keep escorting. When I first started in Fairfield, my plan was to work for a couple of years, build a nest egg and move on. Well, that was three years ago and my nest egg is growing fast. But I really have no intention of quitting a great, hassle free, escorting business. Maybe when I am thirty and look more like my clients’ wives than their daughters.

However, I do have one plan which I am working on: if I can keep a couple of dozen hedge fund managers happy I am pretty certain I could keep one delighted. So, very quietly, I have started looking around in Boston for a real live hedgie husband. And I do know that I would find more in New York, but just like escorting, the New York marriage market is stupidly competitive. Plus, almost all my Fairfield clients either work in New York or work with guys who do. Boston is a world away but there are still plenty of nice, wealthy, guys who are, though they may not know it, in need of a wife.

I am taking my time. Escorting in Fairfield, seeing my regulars, taking little shopping sprees to Manhattan, reading fills my days. I have created a little personal consulting business for cover and, soon, I’ll be escorting in Fairfield and consulting in Boston. Hedging my bets as it were.