Money Sex Page 4

  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.

  Outside the bedroom I am very demure. Prim. But with an edge. I’ll wear a quarter cup bra under a thin cashmere sweater so my client is pretty sure he can see my, often hard, nipples as I serve him tea or fix him a drink. Many of my skirts and dresses have cunning slits where my stockings tops show. In the bedroom I am just as demure and just as proper. My clients almost never see me completely naked and I am more than happy to pretend to be just a little reluctant at first.

  Hedgies tend to be performance driven in bed and out. They want to break down a girl’s resistance and then go all “Master of the Universe” on her. Which is fine with me. I am always well lubricated and, honestly, I like sex a lot and I like being paid to have sex even more. Thinking of a shoe box full of hundred dollar bills gets me wet every time. So, I have no problem lying back and spreading my legs and thinking of the Benjamins.

  But even when I have a millionaire eight inches deep in my pussy I keep up my ladylike persona. No “dirty talk”. No touching my backdoor. And, unless I know a guy really well, I don’t like having my pussy licked. It isn’t that I don’t like the act itself – done right it is lovely – but it is so intimate that I keep it as a treat for special clients. I am very enthusiastic in bed but I have very hard limits.

  Lots of my hedgie clients like to get more than a little kinky. I did mention strap ons? But, like trying to buy a Birkin at Hermes, you have to work up to that. I will not even discuss kinks until I have seen a man at least four times. By then I know him and he’s invested several thousand dollars. On that fifth date I might test the waters a little with a well lubed finger up his backdoor. If he likes it then we can talk. Kinkiness, whether it is my wearing something special, foot worship, golden showers (for him, me never) or a good pegging, is always expensive, very expensive. Basically double or triple my normal rate. But by the time it even comes up I know whether I am dealing with a minnow or a whale.

  My clients really like the fact I fit into their weird, upper class, preppie world so well. They don’t want to date models or girls who lack the refinement a good college education brings. As I said, they like the fact I could easily be their daughter or their, likely second, wife.

  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.

  Juliana

  The Luxury Approach

  There are plenty of escorts out there who promise to pamper, to be luxurious, to spoil their clients. After all, booking an escort is a luxury purchase and in a competitive market some escorts will try to cater to that end of the market.

  At the same time we were amazed to see an escort ad which really sounded more like an ad for a high end spa than a roll in designer sheets.

  We wanted to find out more and reached out to “Juliana” through her very attractive website. A website which looks, for all the world, like a modernist piece of art. All pale, beautifully faded pastel colours.

  “I work in San Francisco.” said Juliana in our Skype call. “My clients are younger, usually very successful, totally driven guys who are pathetically stressed.”

  Juliana had set her Skype up so that she could use a DSLR to shoot her video and this mean we could see both her and, in the background, her astonishing apartment. She didn’t advertise her age and we didn’t ask, but at a guess she was a very well taken care of early thirties something woman. Her honey blond hair was cut in an asymmetrical bob and she was wearing a pretty, pale grey, light knit dress. Very red lipstick and natural, but present, make up.

  Behind her we could see an enviable apartment with sun streaming in through tall windows and modern black leather and chrome furniture. It is a pet theory of mine that the size of a space matters less than how high its ceilings are and Juliana’s apartment looked to have, at minimum, fourteen foot ceilings. All painted a honey taupe with black framed, large, fashion photographs stacked on the walls cleverly.

  Juliana spoke with the sort of assurance one expects to see in a lawyer or doctor. Full sentences, no slang, careful diction: all in a rather soft voice which seemed to come from a very deep, very calm place deep in her chest. A chest one could not help but notice, graced with braless breasts which were larger than one would expect on such a light, lithe, frame.

  “The last thing in the world my clients want is a lot of over the top sexual stimulation. Really just the opposite. But it took me a while to realize that.”

  “I didn’t start escorting in San Francisco. I really started in the alt sex work scene in Portland. You know, Suicide Girls and the only vegan strip joint in America. I’d finished my undergraduate degree at Reed College so I was dug into the whole Portlandia thing. Which was fine and it was a graceful introduction to what the lumberjack shirt wearing girls call “sexwork”. It was all surprisingly innocent and I had my first date with a software executive with a sleeve of tattoos and some sort of complex about wanting to help girls like me. Which was actually pretty funny because, of course, in order to save me he seemed to need to see me once a week and, as he was there anyway, a blow job was not out of the question. Men!

  The problem with the sex work scene in Portland is that there was not a whole lot of money in it. Or at least the way I was doing it. And, honestly, I’d been in Portland for nearly a decade and the novelty had worn off. I’d always loved San Francisco. Beautiful, very much a great city and the center of the tech universe. But it was really expensive.

  I did a bit of scouting online and I thought there might be a market for an independent escort who came at the escorting business from a luxury perspective. I had some money saved from my Portland business, not a great deal but enough that I could rent an apartment and buy a bit of decent furniture. I drove down to San Francisco one weekend and looked around at apartments. Wow. I knew it was expensive but this was crazy. I’d wanted a two bedroom apartment, one bedroom for work, the other for my actual life. No chance of that I realized looking through Craigslist.

  I have to admit I got pre
tty depressed looking at $4500 a month 750 square foot boxes. I was staying at an AirBnB spot near downtown and I came home the second day looking pretty glum. My host, a wonderfully festive old queen who had bought back in the 1970’s was waiting with a big glass of chardonnay and some appies. We sat on his roof deck overlooking the city. I told him about my house hunting disaster.

  “Well, do you like where you are staying?” he asked. I told him I did. “Well why not rent it?

  I explained to him that the nature of my work made privacy pretty essential. “And what do you do?” It was a big glass of chardonnay, almost gone and I told him. “Good for you dear. I suspect there is a big market for girls here. There certainly is for boys.”

  We did the deal on the spot. Basically I got the bedroom and living room I was staying in plus the private bath and another room which I am in now which is just off the living room. No strings attached and half the price of the places I’d been looking at. And, the best thing, it was totally furnished with just the sort of modern furniture I was planning on buying. I paid the deposit, drove back up to Portland, had a garage sale and put what was left in the back of my car. I drove back down to San Francisco along the coast highway because I had five days to kill before

  Every escort I have known has a working name. I wanted mine to be a bit romantic, soft and feminine. But I wanted more than that. The girls I knew in Portland who escorted usually were pretty much the same girl escorting as they were in their straight lives. Which is fair enough but not what I wanted to do. Or, more accurately, I wanted “Juliana” to emphasize certain elements of my own persona in an escort setting.

  While it was not a popular position in sex work in Portland, I like to spend my time in a feminine, sleek, expensive environment. I like well tailored clothes, a great hair cut, careful grooming and a sense of gliding into a room. Portland sex work was more feminist than feminine and that always made me uncomfortable. My sense was that there would be a market for a really feminine, stylish girl who went out of her way to create a very safe, very unstressed, environment for her escorting clients.

  Most of all, I wanted my prospective clients to really “get” how luxurious a few hours with me was. And it was that luxury which I thought would sell my escorting services.

  From the very beginning I wanted the consenting adult activities to be a part of a much bigger package. Girls will talk about the “Girlfriend Experience” which I get but it’s not really what I wanted to offer my escorting clients.

  I wanted to give very driven, busy, stressed men a break, a pleasing pause in their lives. To do that I wanted to change up the escorting business model a bit. As economists would put it, escorting is pretty much defined by its “transactional” nature. Bluntly, the client gives the escort money and she gives him a good time. This business model was what I had used in my Portland sex work. Now part of the reason the transactional model is used by escorts is that they see each encounter as, essentially a one off deal. Even with their “regulars” each encounter has to be seen as the last encounter. As I drove down the Coast and into the redwood forests I realized that this was not the only model which would work.

  Wealthy men have had mistresses pretty much since the beginning of wealth and less wealthy men – or cheaper ones – have sugar babies they keep on an allowance. I was very definitely not the sugar baby type largely because I really did not want to see the sorts of men who “kept a side piece”. I had no objections to being kept as a mistress. In fact, in my notebook I had a separate page for “mistress”. But was there something in between being a girlfriend experience escort and a mistress?

  I thought I had a potential solution. Keeping a mistress is a big commitment and one of the reasons men see escorts is to avoid any commitment. But what about what amounted to a time share mistress arrangement. Basically, instead of selling dates one at a time, why not sell a block of time, say three months, with an evening a week and the occasional afternoon of fun as part of the package? Not for every client but as an option.

  The other thing I thought would work in the bigger market of San Francisco was the idea of a flat rate, no time limit, date as the basic way I sold my escorting services. Yes, that would limit the number of clients I could see; but if I set my rates high that would not matter and, in fact, I was a lot more comfortable being a low volume provider.

  Given what the guys in San Francisco were apparently able to pay in rent, my business model assumed six high end clients a month with one or two invited to participate in my “time share” mistress idea. But I left that idea out of my escort advertising.

  In fact, I left any reference to escorting out of my advertising. Instead I advertised as a stress management consultant. “Experience the healing arts of a beautiful woman in simple, modern space. No time for a girlfriend, driven by your success? Find out what you are missing without the added stress of a relationship. I never text, I never call, I don’t need you to either. I am just here. Ready, beautiful, relaxed when you need me.”

  I had a great picture from a fashion shoot I’d done for a friend a year before. Me in a really pretty jacket, no top, looking side long into the camera. Fashion forward, modern and my favorite picture. And it had the virtue of looking like me, but only from a certain angle. I wanted to keep my escorting very discreet.

  So, I got to San Francisco. My lovely landlord actually baked me a cake with the wonderful line “Welcome Strumpet” in bright red icing which matched a kissy lip print. I settled in and put my ad up. I did use escort advertising sites but I also put the ad in print in a couple of the entertainment guides. Because it was not at all “escort” they were happy to run it under personal services.

  I set it up so that to contact me you had to go to my website. I learned a lot about screening when I worked in Portland and I really wanted to see only escorting clients who were willing to be up front with me. With the internet it is amazing what you can find out and confirm with nothing more than a name and a location.

  I post my “all in” price and a couple more pictures. Plus, I have a couple of really nice shots of my space with some fresh flowers. It is all designed to look really inviting and calm. Again, something which I learned in Portland is that while some men are seeing an escort for the sheer excitement, a lot of men are there for a break. Those were the ones I wanted.

  So, a few hours after I put my ads up I had five or six queries and two of them seemed to be men I would like to see. So I made arrangements and, before I really knew it, I was getting ready for my first appointment as a San Francisco escort.

  I am a girl who likes dressed and skirts and tops. A long high collared lightweight knit dress, like the one I am wearing right now conceals and reveals at the same time. I know I have a small frame and surprisingly large breasts. And yes they are natural. The right knit dress, a clever lacy, unpadded, balconette bra and a silk chemise and I am temptation itself. Switch over to a full cup bra and I look elegant and very much a lady. Which is, frankly, how I always present for my appointments for first time clients. Part, but only part, of my service is sexual and it is not a given on a first encounter. There have been a couple of clients who, frankly, were just not at all plausible for consenting adult activity when it came to the crunch. And I tell my clients up front that this is a possibility. The ones who blow me off when they hear that are doing us both a favour.

  I am also a girl who figured out her make-up, hair cut and skin care years ago. It really does only take me twenty minutes from a standing start to get ready for an incall escorting appointment. But, and this is huge, in fact I take a couple of hours most of the time because I want my space to look wonderful and I always have a few appetizers and some nice, fairly low alcohol, wine to serve. Then I make sure there are fresh really great towels in the en suite and beautiful clean sheets on the bed. Flowers of course. And, if it is evening, candles.

  My clients feel like welcome guests and, eventually, friends, who are stopping by for a bit of conversation and relaxation. N
othing is hurried. When it is time to move things along I’ll usually have my client unzip the back of my dress and lead him to either the en suite where I have run a bath, or directly to the bedroom.

  There is very little about pleasuring a man I don’t know but the actual fact is that most of my clients, after a little gentle teasing, simply enjoy a willing, gentle partner who apparently enjoys herself as much as they do. I suspect that is the real secret to the escort’s art. Bathing a man, with lots of unscented bubble bath, is incredibly relaxing and erotic all at the same time. Once in a while I will actually give a client a soapy hand job and then rinse off his cum. Other times I will strip naked and join my client in the tub.

  In bed I am really all about taking lots of time and really going deep. I don’t mind sucking a client’s cock, on and off, for half an hour and edging him. But I also love it when a client just can’t wait and wants to fuck me immediately and hard. I will urge him on and then, when he has relieved his unbearable urge, I will lie with him and bring him back so he gets hard again and can enjoy my pussy more gently and completely. My clients think it is all up to them but, really, everything I do in bed I control. I often come for real with my clients but I am very good at the minor art of orgasm faking if necessary. Happily, whether I come or not I am a very wet girl naturally so I am able to enjoy being fucked just for the pure sensation.

  I saw three clients in my first full week and one of them became my first “time share” mistress client. He loved the idea. The way I worked it out was that my time share client would pay me monthly for an agreed number of visits, usually four or five. I discounted my time a little for this arrangement but what it really did was remove the whole “transactional” element which makes conventional escorting seem more than a little cold blooded.