Money Sex Read online

  Contents

  Introduction

  Jane

  Artful Escorting

  Annie | Tonya | Kelly

  Back to School – College Escorting 101

  Rachel

  Escorting the Hedgies

  Juliana

  The Luxury Approach

  Trish

  Mile High Escort

  Sybil

  Lesbian Experience

  Elise

  A month at a time

  Martine

  Playing the Part

  Jasmine | Bree | Candace | Rosy

  Escort Style

  Charlie

  Private Dancer: A stripper and an escort

  Introduction

  In the course of writing Avails: Escorting for the Elegant Woman, Questions for Miss Jay: An Escort's Guide to Style, Dates and Fun and Modern Mistress: Lead the Luxury Life You Deserve I had the good fortune to speak with literally hundreds of women who, for all sorts of reasons, decided to make the link between sex and money.

  Each of these wonderful women approached the money/sex nexus from her own perspective and met her own needs. Some were “kept” in the old fashioned sense of being one man’s exclusive mistress, others escorted very occasionally, still others made a business of pleasure: all of the women I spoke to did, however, share one thing in common, they made their decision themselves.

  When I interviewed escorts and mistresses I kept notes of our conversations. Some of the girls were very coy about “consenting adult activities”, others were deliciously graphic about the services they provided. Because I was focused on the higher end of the market, the women I spoke to tended to be articulate, smart and very savvy. Most were college graduates and many used escorting as a way of financing businesses or art making or lives of interest and value.

  I fear I have no interest at all in the lower reaches of the business. There is nothing glamourous or erotic about a five minute car date or twenty minutes in the dirty sheets of a “no tell motel”. I am interested in the glamour, the illusions and the erotics of an often beautiful young woman selling her favours and herself to a well off gentleman (or lady) caller.

  This is the first of a series of books about the carriage trade of the escorting world. These girls enjoy the so called finer things in life, they stay in shape, they read, cook, dress beautifully and, so far as I can see, are, from all appearances, ladies.

  For their privacy I have used their working names throughout. I have also changed any identifying details – cities, locations within cities, store names – to ensure my reader hears their stories rather than gains clues to their identity.

  It is actually rather sad that these delightful women have to be protected in this way. Escorting, courtesanship, mistresshood are surrounded by a thicket of prohibitions, legal and social, which deny these women the right to choose their profession. In fact, these women are bringing gifts to the men who patronize them. They are leading good lives, building real businesses and bringing a bit of joy into what are often rather dreary worlds. Rather than being scorned, insulted and even arrested, I believe these women should be celebrated for their courage and vitality.

  This book is my celebration.

  Jane

  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 blond 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.

  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 s
ervice 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 Nordstrom. 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. I was delighted to see a pleasingly average cock when it was time to go to work. I actually enjoy blow jobs when the cock in question is not too long and not too thick. Larry’s was just right. I did his first blow job in my chemise, long nude stockings, garter belt and panties. Which Larry seemed to very much enjoy.

  Practice has taught me that a huge part of a great blow job is eye contact. As you are flicking his little head with your tongue, for Heaven’s sake look the lucky man straight in the eye before averting your gaze and taking him all the way in your mouth.

  I’d decided that with an up market clientele, a bare back blow job was a minor risk. But I was not going to swallow. So when Larry was ready to shoot I knelt in front of him and said, “Cover me in your sweet cum Larry.” Words are very powerful and, in two strokes, he was happily squirting a pearl necklace over my face and upper chest. I directed the goo and, having taken the shoulder straps of my chemise off a bit earlier I was able to pull down my top to catch the last delicious drops on my pretty tits.

  And then I remembered something an old boyfriend had liked. After licking the last of his mess off the end of his cock, I began rubbing his cum into my skin wherever it had squirted. I took my time and my eyes never left his as I spread his sticky cum over my cheeks, over my forehead, down my neck and into my already hard nipples. I saw his cock twitching for the second round and said, “Not quite yet Larry…I want to have a nice, warm shower and be ready for you.”

  Which is exactly what I did. All that cum was rinsed off and I scented myself carefully. Before rejoining Larry I lubed my pussy. Not too much, I was already very wet, but a man likes to think he has his little whore really excited and the lube adds to the sensation. I left off my chemise and panties but put my stockings, cinch waist garter belt and heels back on. And I put on a hotel supplied dressing gown. I didn’t bother to do it up. A couple of quick nipple pinches and I walked back into the suite.

  “For a beginner you certainly show a lot of promise.” said Larry as I walked over to the bed. He was naked but under the sheet.

  “Thank you kind sir, I like to try. But I see you are ready to try out the rest of my skills. Did you put your condom on?”

  “Yes.”

  “Wonderful. You know what I just love?” I asked getting onto the bed beside him as I stepped out of my dressing gown.

  “No, what?”

  I knelt on the bed and slipped a couple of the 500 thread count pillows under my hips.

  “I love it when a man takes me from behind, just my pussy. My backdoor is another date. But just push in and fuck me. No reach around. Just my ass up and my head down until you are done.” I put my head on the bed and looked up at Larry.

  He didn’t have to be asked twice and I soon felt his nice, average, cock pounding away at my wet, lubed pussy. He loved not h
aving to pay any attention to my pleasure and, honestly, I loved that too because I had one more trick up my sleeve.

  It didn’t take long for my dripping, clenching pussy to push Larry over his edge and he rolled off me entirely satisfied. I had spotted the tissues and made something of a production of slipping his surprisingly full condom off and licking his cock clean again. Thank heavens for Viagra because, before I was done I could see a little life in what would, under normal circumstances, have been a very limp dick.

  I lay beside Larry, making sure that one of my breasts was resting on his chest and I lifted one of my stockinged legs up onto his thigh. I let him rest a bit whispering how much I loved his perfect cock taking me doggy style. I mentioned my backdoor tingling as he fucked me – and yes, a good girl always says “fuck” and “cunt” in bed – so he would have the possibility for next time. And then, as I spoke I reached down and began to play with my genuinely soaking cunt. Being fucked from behind is something I have always loved. But I never come that way. So, years ago, I realized I would have to bring myself off.

  I think most girls masturbate but I had learned from that same old boyfriend to be very comfortable, excited in fact, to masturbate myself for the man who had just fucked me. Now, if I want to I can snap off an orgasm in a minute or two, or I can take my time. With Larry I took my time. He couldn’t see me when I began touching my little clit which was already nicely engorged from her earlier fucking. He felt my hand against my pussy and, he’s a smart guy. I ground a bit on his thigh. But doggy style really does not get the job done. Which is fine, I like the feeling of being taken. And for me sex is about those sorts of feelings as much as the actual physical contact.

  As I stroked myself I got wetter and I could see Larry realize what I was doing. As soon as he did, to my delight, his lovely, cut, prick began to find strength it never had. I rolled on the second condom of the evening before I got too distracted with my own pleasure.

  “Have you ever watched a girl masturbate Larry. Play with her cunt for you?” I asked as I was beginning to get close. I rolled over on my back and Larry looked as if he was thinking of mounting me. “No, you just lie there and get hard and watch me make myself all wet for you.”