Money Sex Page 6

  In the lesbian world things are a bit more complicated and the edges much blurrier. For example, straight female escorts, from time to time, are hired by women. Or couples. While they certainly engage in girl on girl activities, it is not all that clear that these encounters would count as lesbian escorting.

  The emotional and erotic world of women is a more complicated place than the male homosexual world or the heterosexual world. But we were interested in exploring how paid companionship works between women and looked around for escorts who lived in that world.

  “By inclination I prefer sex with women.” said Sybil a very pretty, willowy, brunette in what looked like her early thirties. “When I was younger and just starting out as an escort most of my dates were with men and that was fine. Men are very basic and most will not even notice if you are a bit distant. In fact, most men prefer an escort to be pretty self-contained and for her to simply get on with the business at hand.”

  “But even early on I had a few escort dates with women and they were completely different. Completely. I am what the popular press would call a lipstick lesbian. Very much the Portia de Rossi rather than Ellen. I love dressing up, putting on lots of pretty make up and really sexy shoes. One client of mine calls me her “style queen” which is pretty accurate because I am completely into fashion. I mean one of the reasons I escort is to be able to afford to buy really lovely things. If I want a $7000 “it” bag I don’t want it next year, I want it now.”

  “I lead a sort of nomadic life. I have a house I bought a few miles out into the desert hills near Santa Fe New Mexico. All very arty and Georgia O’Keefe; but I like to spend a few months at a time in decent sized cities on both coasts. Escorting lets me do that.”

  “Over the last few years I have shifted my advertising and my website to be much more lesbian or, more accurately, female friendly. When I was younger I had an escorting clientele which was 80% male, now it is 80% female and, to be honest, I really only see men who have been clients for years.”

  “I could spend a lot of time talking about the differences between male and female expectations for an escort – and they are huge. But the expectations are only one side of the equation, the dates themselves are night and day.”

  “Men appreciate a nicely dressed, well made up, pretty “hair and nails” girl but it is all very much preliminary to the main event which, usually, takes place between the sheets and is, ultimately, what the gentleman thinks he is paying for. Women are completely different.”

  “Most of my women clients come at the whole thing very differently. They are looking for connection.”

  “In my experience, women who want to see an escort come in two very distinct flavours: the first are women who like girls, know they like girls and are pretty open about it. The second group, and they are about half my clients, think they might like girls, or have experimented a bit with girls and liked it, or are married but missing something.

  The women in the first group are usually a lot of fun. They have usually come to a place in their lives where they enjoy other women’s company and the frission of excitement knowing that the evening will end in bed. But, and here is the thing, it is very much an evening. We’ll meet for a glass of wine, perhaps have a light dinner, maybe go to a lesbian club a bit later and then, likely after a nightcap or a dessert, we’ll end up under the covers. Nothing happens quickly. I am not sure it would even be possible to be a high volume lesbian escort.

  The women in the second group – the experimenters, the girls who had an experience in college and want to try it again, the wives who are pretty sure that something in their marriage is not quite right, are wonderful. For some of them simply calling me is a hugely important step in getting their lives in alignment with their sexuality. Now, I hate the whole idea that escorts can or should be therapists. But I think the mere fact I am available to these women is therapeutic. And, frankly, so do my out lesbian clients. In fact, I have had women who were uncertain of their real sexual identity referred to me by those lesbian clients.

  In a very real sense I am the safe place for women to explore the feelings of attraction they may be feeling for other women. If you are a nice Human Resources manager and a soccer mom and you suddenly find yourself really hot for another girl it may be a good idea to see if you even like sex with a woman before you take the risk of opening up to that girl. Along the way you may discover that women’s sexuality is somewhat less binary than male sexuality. Or not.

  Of course some women, whether long term lesbians or experimenters have a real problem with the whole escort thing politically. There is a certain streak of anti-sex feminism which sees escorts as inherently victims of the patriarchy even if they are seeing women almost exclusively. It is really annoying frankly because these women want to see me as some sort of symbol rather than as a woman with her own “agency”. Now, that anti-sex streak of feminism is, mercifully, dying out but I still have heart to heart conversations with some clients where they are trying to convince themselves that I do not lack agency even though I am an escort. It seems very odd.

  On the other end of the spectrum, I escort more than a few women who are, quite frankly, bored to death with the more caring and sharing sexual paradigm embraced by progressive lesbian couples. They want the intensity and the anonymity which often characterized the bar scene when they first came out. Which is a world which I really did not play in, but I can enjoy it if that is what my client is interested in. I will never manage the full on “bull dyke” or various other butch personas but I love getting into skin tight designer leather with my vintage ‘80s Claude Montana short black leather jacket and a pair of sky high heels and do a semiserious domme impression with a client. And, yes, at some point in the evening she probably will be up against a wall with my hands in places nice girls won’t normally want them. And, yes, later I might well tie up my client to “Constant Craving” and leave her gasping.

  One thing the majority of my full on lesbian or experimenting clients really enjoy is a degree of glamour when they see me. For some of my clients glamour is part of their business – art directors, women who style or photograph fashion shoots – and they appreciate how I look because they know what it takes to look as glossy as I do. For other women, how I look, walk, dress and even speak is a path they might have followed but didn’t. There they are in their office drone pantsuits or the not terribly flattering outfits women lawyers seem to insist on wearing in order to look serious and across from them is a pretty girl in a dress and stockings and, perhaps, gloves. When I am out with these women I always look like “the girl” because I will be wearing a pretty, low neckline cocktail dress or a full skirted dress with a bustier top. Because, unlike when you are on a date with a male client, with a female client you can look very tarty – in an up market sort of a way – without anyone raising an eyebrow or thinking, “Well there is an escort.” Two women having a drink together, even touching affectionately, does not really arouse any interest at all. Or at least not negative interest.”

  “Ultimately, though, the difference between a lesbian escorting experience and a straight one lies in your client’s need for connection. I am not saying my male clients don’t care who I am. They do, or at least most of them do. But, when it comes down to it, the men are hiring a girl for a particular purpose and “getting to know her” is not that purpose. And men are remarkably oblivious to the things women pick up on just sitting down for a glass of wine.”

  “Remember I said one of the reasons I like escorting is that it lets me buy pretty things like bags. As you might imagine if I carry a Prada or a Celine bag on a date there has never once been a man who has said, “What a lovely bag.” For my female clients my bags are a point of entry. They want to know what bag it is, where I got it, why I picked this colour rather than that one. A male client might take me shopping and spend several hundred or even a couple of thousand dollars on me. But he does not “go shopping with me”. I have a few wealthy female clients who love
nothing more than to go to lunch and then hit the stores. We shop together. Yes, she pays, but often we will buy more for her than we will for me.”

  “Most of my female escorting clients are pretty well off. And most of their money is discretionary. While some have children, the majority don’t so they don’t have college and school and family vacations to worry about. If they are partnered it is often with a woman who makes just as much money as they do. Which means my female clients can afford to book much longer dates. I discount my rates a bit past three hours and a lot of my female clients will book five. Why not, they can afford it.”

  “Not, of course, the experimenters. Those women are often counting every penny and get really worried if we go over time. I never worry. I enjoy my escorting dates and watching the clock is not part of the enjoyment. Letting a shy woman touch places she has kept hidden for twenty years is wonderful and deeply rewarding. For some of them, hiring me was a way of coming out, for others it simply scratched an itch. With my experimenters the escort dates were not usually as long but these ladies would come back, often a couple of times in the first couple of weeks and then somewhat regularly.”

  “My more “out” lesbians have also become regulars more often than not. But, even there, the regular female client is so completely different from the regular male. One of the biggest things for my female dates was the fact they could go out with me and not worry about my becoming emotionally attached. Over a number of dates we’d become “girlfriends”. Girls who liked to spend a few hours together once or twice a month usually over lunch, coffee or drinks and then back to either her place or mine.”

  “The regulars really do become friends. Again, the difference between men and women. Men are delighted to see me but, if I moved to another city tomorrow, they would find another girl. With women after a few dates there is a real connection apart from the escorting. I think a part of that is social. I don’t think it is any secret in parts of the lesbian community in my cities that I am an escort. I also don’t think most of the more successful lesbians care all that much.”

  “For my partnered and now, sometimes, married clients, I am very much a safety valve. A little spice to keep things hot. In fact I have one couple who see me separately every few months. Each knows the other is seeing me and as one of them said, “It’s like a rebirth of our own bedroom lives.” I like that a lot. It is silly to generalize about any group of people and even sillier to generalize about “lesbians”; but I think a lot of lesbians are much more open to the idea of escorting than straight women. They don’t feel threatened by a young, glamourous girl because they have their own really solid relationship.”

  “Probably the thing which I value most about my female escorting business is that openness. I am often invited to client’s parties, not as an escort, but as an interesting woman in my own right. That does not, and cannot, happen with my male escort clients because it is basically impossible to explain a pretty young single woman who you don’t actually work with. Lesbians don’t seem to worry that much.”

  “The part that is hard about lesbian escorting is the same part that makes it easier – the women I see want to actually know me. They want to get past the escort wall and into the hidden garden. Where the men will, literally with a sly grin, ask “How did a girl like you get into a business like this?” and be very happy with, “This and that and then less of this and more of that.” my female clients get a bit obsessive. They really do want to know why I escort. When I tell them “For the money.” they dig deeper.

  I spent one escorting date with a woman who, along with many other accomplishments, was a PhD psychologist. She really, really wanted to know. So I told her. I explained that by escorting I was able to make the money which let me led a very simple, deeply refined life where I could read or go to the Museum or afford tickets to the Opera or indulge in my taste for really pretty clothes and bags, keep my house in the desert and live in two cities. I was telling the truth but she was not buying it.

  “Don’t you get a terrific sense of power, of giving, of intimacy from your work?” she asked.

  “Perhaps.” I replied, “But I really like the fact that I am an escort. That my time, my body, my skills, my pretty dresses and lovely lingerie are appreciated. That women, and men, pay me for my time and my company. Escorting empowers me.”

  “All she did was smile. Which was as annoying as Hell because her smile implied she “knew”. What she knew I don’t know. I do know that she had a wonderful time and has been back to see me half a dozen times without the “Why do you escort?” question coming up again.

  “Law enforcement? Don’t be silly. My ads and my website are brilliantly vague. Coded for lesbians but interesting to men as well. But they are all designed to leave a police officer wondering if I am a companion, a therapist or just plain friendly. Escorting does not come into it. My ladies and even my gentlemen can read the code. I suspect most police officers can too but the whole gay thing is too politically fraught for them to really want to set me up. Or at least that is what a client and friend of mine who is an assistant DA tells me. So I never worry.”

  I’m not actually sure how long I will keep doing the lesbian, or really anything, escorting thing. Many of my clients at twenty or thirty years older than I am so I suspect I could keep going for years. At the same time I keep getting great job offers from clients. Usually no strings attached. But if I took a job it would mean an end to long lunches and early cocktails and living where I want to. Escorting, at least escorting my way, is a life I am used to and I am good at.

  If I had to guess I suspect that falling in love would end my escorting career. I have dated more than a few women and a couple of men on a non-professional basis. I’ve tried it both ways: where I tell them that I escort and where I am vaguely a consultant. The men seem fine with the escorting thing. Excited even. But it is a huge issue for the women. Not because they are particularly judgmental, they aren’t; but they cannot imagine how a relationship with an escort, even an escort whose clients are mainly women could work.

  Generally, women tend towards monogamy – I have had a number of offers to become another woman’s mistress simply because she does not want me seeing other women. Men are far more laissez faire, prepared to accept the idea of compartmentalization because that is how they think themselves.

  So if I did fall in love with a girl, and I have very nearly several times, I suspect I will hang up my Louboutins and leave escorting behind. Which I will miss.

  Elise

  A month at a time

  An escort friend of ours suggested we get in touch with a friend of hers. “Elise has a totally sweet deal” she told us giving us Elise’s contact details. So we phoned. And emailed. And Skyped. And then we gave up because the one thing escorts are supposed to be is easy to contact.

  Two weeks later we got a very sweet email from Elise. “I am so sorry not to have been available when you were trying to contact me. Let’s chat and I will tell you why.”

  Always game for a challenge we emailed back and set up a time. An elusive escort is interesting.

  Elise duly appeared on Skype and, to be honest, she was one of the prettiest, most vivacious, escorts we’ve ever interviewed. Lovely brunette hair in loose curls frames a wonderfully angular face and the sort of pale blue eyes people from Sweden or Iceland have. She was, so far as we could see, dressed casually in a perfectly ironed white cotton shirt. Again, it was a little tough to tell on Skype, although her lighting was clever, but we were pretty sure her shirt was well darted to ensure that her pretty breasts were accentuated without being flaunted.

  Elise had a nice, well modulated, speaking voice and when she said “Well, as they say on Reddit, ask me anything.” we did.

  First off, why so hard to reach.

  “It is actually pretty simple, I only escort a couple of months a year. The rest of the time I am either travelling or working as a consultant or both.” said Elise as if taking a couple of escorting breaks in
an otherwise busy schedule was the most normal thing in the world.

  “I work as a revenue enhancement consultant for a number of world class hotels. I go to a particular property, spend a couple of months as a reception desk clerk or fill-in night manager and then write up what I see and recommend where improvements can be made. It is a bit like being a secret shopper but way better paid. The fact is that I can usually improve a hotel’s performance by a couple of percent which does not sound like much but really adds up in a three or four hundred room property.”

  At the same time I love the cash I make escorting for a couple of months a year. So I arrange my consulting in three month pieces and leave a month between each one. That’s when I put up my red light as Sting would put it.

  Escorting for me is a pure cash business. I have non-bank safety deposit boxes in a couple of US cities and I really do have one of those super secret Swiss bank accounts. If you know what you are doing you can set up a system where you can automatically route any credit card payments to Switzerland and you can arrange wire transfers as well. Especially if you have a few months in between the high cash escorting months.

  How did I get into escorting? Well, before I was a revenue consultant I worked front desk at one of the best hotels in the city I grew up in. I was going to college and I could do that job a couple of nights a week. I didn’t need much sleep when I was a kid.

  When you work front desk in a hotel you meet a lot of people. I worked during the week and most of the guests in our hotel were businessmen. Of course there were business women too, but say 80% of our guests were in town for a few days to get a deal done or a lawsuit settled. Our rooms were not cheap so we didn’t get a lot of salesmen or guys on training courses. Just a steady stream of executives, lawyers, accountants and the occasional owner – those guys took the best suites.

  Front desk has a security function in a hotel. We are required to keep an eye on our guests but, more importantly, on people who are not our guests. Our guests take clients and friends up to their rooms all the time. No big deal. What we are watching out for are people who don’t belong. If we spot them we alert security and leave it there.