Money Sex Read online

  Biggest challenge? OK, this is weird, but way too much money. No, really. When I am not doing exams I can see two or three guys a night five days a week at $250-300 a guy. You do the math. 2000 to 3000 a week is what most of my girlfriends have to live on for a semester. It kinda shows. I try to be cool about it but girls notice a new bag or a really cute dress. I say my parents bought stuff or sent me money. But I really do have to be careful.

  And, of course, there is the damned phone. I keep it turned off in school but if I turn it on and I have an ad running and I’m having coffee with a girlfriend nine calls in ten minutes begins to show. I don’t think they have a clue. But I am sure some of them think I run a giant drug empire or something.

  The only other downside is that this is not that big a city. I see my clients all the time in the same places I like to go to. Most of them are really cool and there is no problem. But some of them feel they have to say Hi. Which is a little awkward if I am out with friends.

  The way I am getting around that is that I keep my hair down on my dates and put it up the rest of the time. I mean I am still me but with my hair up I look just different enough that a client feels ok not recognizing me.

  Long run? Look, I’m twenty, in second year. I don’t really even know what I want to major in. But, seriously, can you think of another business where a girl my age can make 10K a month working pretty part time? I can’t. I have two years of college left and I know I am going to escort through those. Beyond that? I want to travel. Maybe go to Australia where this is totally legal. I mean my main worry is that some cop will go on a crusade and catch me. Which would kill my parents. But I have never had a hassle yet. So, really, I don’t know. The cash is awesome.

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  Two very different approaches and there are hundreds of other college girls each with their own take on escorting. Kelly, who is a twenty one year old art history student, has a radically different take on the escort business.

  “I decided I wanted to have a lot of time to myself so I could really go deep with my studies. That takes money but money that I don’t have to put thirty hours a week into. I looked around and tried being a “sugar baby” for a while. Not my thing at all. I didn’t want to be someone’s pay to play girlfriend and a lot of the guys you meet are very unpleasant. But the idea itself was is not half bad.

  When I came back for third year I had a bit of a plan. The big problem with sugaring is that the “boundaries” are badly defined. You get booty calls at 2 in the morning. On the other hand, very selective escorting when it works, has all the boundaries in place. The problem there is that it is hit and miss. Busy one week, dead the next. Plus, in the city I live in we have a very active “vice squad” and state law which is pretty hard on even higher end girls.

  The solution I came up with was to start looking for several men who would enjoy pampering a pretty young college student in a mistress style relationship. Not sugar, not exactly escorting: rather an evening or an afternoon every couple of weeks for lunch or dinner and then a lovely, sensual, encounter. Which was pretty much what I put in my ad. Because it was not directly escorting I was able to put it in the companionship section of the advertising sites.

  My dates were just that, dates. I always let the gentleman bring up the subject of money and I never set a price directly. Instead I would say that I very much appreciated generosity and I would always say that I liked to see my friends with no time limits and no more than twice a month. Some of my gentlemen pay me each time they see me, others prefer to make a monthly arrangement.

  I entertain at home for the most part although I have seen men at their hotels. But the key thing is that I try to provide a wonderfully luxurious, genuinely non-rushed, encounter. If I see more than one man in a day it is because of an unavoidable scheduling problem. Right now I have a waiting list because I limit myself to six patrons at any one time. I know that restricts my income but seeing more would eat into my time and I don’t think I would provide the same, superior quality service.

  I like older, very married, men. They are so very grateful. I like to tease them a bit and I’ll play with their cocks long before I undress or they do. It is amazing how men react when you reach down there and say, “Are you hard yet?” If they are not hard when you ask, they are thirty seconds later. First dates I go one round, blow job or a good old fashioned missionary style ride with none of the trimmings and a party hat. Once I get to know a guy my horizons expand and I am happy to do BBJs and doggy and reverse cowgirl. I become a porn star date but only when I know they are willing to pay to play.

  I don’t like to talk about my actual income, but I never see a man a second time who does not bring a minimum of $750. Most of them quickly get the hint that $1000 plus a lovely gift and a tip will ensure I am available when next they call. I screen every man I see thoroughly and I never accept random encounters.

  I am a bit snobby. If I was three inches taller I could model. I much prefer wealthy, older men for who a $2000 dress is just the sort of thing a girl like me needs and which does not matter to their wallet. It’s great fun.

  After college? I can’t imagine closing my little business until I get married. Why would I?

  Rachel

  Escorting the 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 Skype 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.

  “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 th
e “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.

  Impossible?

  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.