The ladies’ handbook of heterosexual male escorts

Women are making much more money than they used to. Not all women of course; but at the higher levels we are seeing women CEOs, CFOs, partners in big law firms and as entrepreneurs. So I was curious to see if I could find male escorts who specialized in these well-to-do ladies.

by Hannah Jay

There is a huge asymmetry between the pay to play girls who escort at the higher end or who are kept as mistresses and their male equivalents. While the gay world has had a lively rent-boy scene forever, the heterosexual world has largely run on girls selling while men are buying. Finding a man who actually worked as a heterosexual escort was not that easy.

Which didn’t come as much of a surprise to Kelly, not his real name, who has been working as a male escort in a large Midwestern city for the last eight years.

“Actually, I am surprised you found me.” Kelly said over Skype. “I run my ad for about a week every three months.”

Once we had that sorted out Kelly was happy to talk. “I make art and shoot some film and photographs. I make a fairly decent living with my work but it was pretty tough starting out after college. I guess you could say I was decent looking. I am a little over six feet, I stay in shape but not obsessively. Mainly I have a great barber and I like nice clothes. Suits, jackets, good shoes, really fine sweaters – a lot of Armani. Which is expensive.”

“I did a bit of modelling when I was in college and I got to know a few of the people who run the nicer designer men’s stores and departments in the city. Which is, oddly enough, how I got into the escorting business. I was in a store trying on a really nice jacket which cost a little over a thousand dollars. I couldn’t afford it but it was fun to play. The manager, Jackie, who I knew, was a woman in her late forties. Lots of fun and she knew a certain sort of clientele very, very well. It was a store which had high end women’s designers on one side with the other side devoted to men. Nice espresso machine and, a little later in the day, glasses of champagne for good customers. I had modelled there a couple of times. I told her I loved the jacket but it was out of my reach at the moment.”

“Oh, I’m sure one of my ladies would be delighted to buy it for you.”

“I didn’t quite get it when she said it but I really wanted the jacket and so I asked, “Who are “your ladies”?

“Well, Kelly, you have seen some of the women who are regulars here. Lots and lots of money. I like to make sure they are very, very happy. And so…”

I still wasn’t getting it and I carried on home. A couple of days later a courier arrived at my loft with a box from the store with the jacket I’d been looking at. There was a note. “Kelly, Marcia Williams would love to see your new jacket.” And there was the name of a nice bar and a time the next night. I suppose Marcia Williams would recognize the jacket.

An hour after the jacket arrived Jackie the store manager called. “You got your jacket? Great. Marcia is a wonderful client and a great gal. I’m really hoping you’ll hit it off. Just let her take the lead and you’ll be fine. Take a couple of party hats.”

I know, I sound a bit dense, but I really had no idea what Jackie was talking about and even the tip about “party hats” flew right past me. The next day, after working pretty well in my studio, I had a shower and a nice close shave, put on a cashmere sweater and a great pair of well-cut trousers, black loafers and, of course, the wonderful cashmere silk jacket my benefactress had sent. I don’t wear after shave. But I am pretty well groomed – my nails are always trim and clean, my hair cut and combed and blown dry – nothing elaborate but when I am going out I like to look my best.

I went to the bar and made sure I walked in right at the appointed time. A rather nice looking forty something woman in a dark business suit gestured me to her corner table. I walked over and put out my hand which she took without standing, “I’m Marcia Williams. Sit down Kelly.”

And off we went. She was drinking a French white wine and I ordered a glass of cab. We sat and chatted for well over an hour. She was in investment banking – which I didn’t know a thing about – and spent a lot of her time travelling. She’d been married but wasn’t at the moment and wasn’t planning on marrying again. “Way too expensive.” No kids. I suppose you could say we hit it off. She took me to dinner in a really upmarket hotel restaurant a block away from the bar and then, after another glass of wine, said. “Well, do you like your jacket?”

I said I did.

“Good. You like nice things, I like nice, somewhat gentle, men. I just don’t have time for dating or relationships. What I’d like to be able to do is call you once in a while.”

“Sure Marcia. Any time.” I said still not really getting it.

“Sometimes I’ll take you shopping, other times we’ll work it out. But right now it’s time for a nightcap. I booked a room upstairs.”

“And that is how I got started in the business. She had an envelope with cash which she gave me before telling me to take my jacket off. She was in nice shape and was obviously in the mood. I saw Marcia on and off for nearly three years. The only thing which changed were the hotels because she liked different atmospheres.

Apparently Marcia called Jackie the next day because I got a big bouquet of flowers from Jackie and a note saying, “Thank you for making Marcie so happy. More soon.”

I have absolutely no idea whether Jackie took a commission from the ladies she sent my way. I know I never made any arrangement. And, the longer I was in the business the more sense that made. Because my clients were looking for a particular experience.

Like most cities there are a lot more interesting, attractive, successful women who are single than there are men. But the further up the corporate ladder a woman goes the fewer available men there are and, worse, the less likely it is that she is going to go out to a bar or a nightclub with a few girlfriends with the intention of meeting a guy. These women have way too much to lose. Socially, economically, they simply can’t afford to do what they would have done in college.

In the beginning most of my clients were referred by Jackie. But one of my clients, Elaine, suggested that it was risky to rely on Jackie for all my dates. Elaine ran her own multi-million dollar a year business consultancy, so I took her advice and started placing very discrete ads. “Straight, smart, funny, affectionate – former model and current artist enjoys the company of accomplished women.” Elaine also walked me through a few fashion websites to give me an idea of why my prices were way too low.

“Realistically, Kelly, women at my level think nothing of buying a couple of $3000 dresses at Net-A-Porter or a $5000 Prada suit with $1000 shoes. Your time should not cost less than her outfit.”

Elaine also pointed out something about my female clients which I really hadn’t thought about. “If you pay attention you’ll start noticing that your clients will rarely book you more than once a month. I mean they will call you to go for coffee, maybe, but they will really only want a full evening or maybe weekend once a month. Escorting women is totally different from escorting men. A wealthy guy will want to see a girl – and often a different girl – a few times a week. Men are like that. But women are biologically very different. We don’t like to admit it but we are totally on cycles, monthly cycles, and the days when we are horny are the only days we’d think of spending serious money on an escort.”

As I worked I realized just how right Elaine was. Some of my clients were absolutely regular – a monthly date and no more. Others were a bit more flexible but there was a bit of a pattern there too.

After a couple of dates with Marcia we went shopping together for a suit. “I love suits and I have a thing coming up I want you to take me to. I got my first Armani suit and wore it to a reception Marcia had to attend for work. It turns out that a lot of the work I do as an escort has a social component to it. In fact, Jacki, the store manager, would often call me to “walk” one of her better customers to a charity gala or benefit or yearend party. “Dress, bag, shoes…man. The perfect evening.” For those dates I had a rate which included consenting adult activity and one where I simply dropped the lady off at her door.

Now, the funny part about heterosexual male escorting is that I have found I am much more in demand as I get a little older than I was when I was in my mid-twenties. I suspect this is because, while I think I still look good, I have just a hint of grey at my temples and my face looks a little more lived in. Marcia told me she would get kidded about her “toy boy”. However, as I get older I look less obviously out of place with a powerful, wealthy woman in her 40’s, 50’s or 60’s. And, with a more mature look my rates have bumped up.

I don’t think I could do this if I had a conventional 9-5 job. Because part of the service is that I take my ladies’ calls, chat on email and text. Plus, as I mentioned, they will often want to go for a quick coffee in the midafternoon. Which may or may not be a code word for a quickie. Usually not. As one of my ladies said, “It is so nice to have the option of sleeping with a man but not the obligation.” I am always paid for my time although the calls and texts are very informal and are usually just rolled into my regular fees.

I know a few female escorts and they tell me that they often have a hard time converting clients into regulars; I have exactly the opposite experience. It is quite hard to get the first date but after that, once a female client realizes that she can trust you, that you are not a creep, that you are good fun and can keep up with her, she will want to see you regularly. But that is all about communication. It is also about creating a particular illusion.

I owe Elaine a lot for explaining some of this to me. But there are a bunch of things I now do which keeps my ladies happy and coming back. For example: I send flowers the next day. Nothing huge, just a pretty bouquet. Of course I ask first – but in general about gifts and calls and discretion. And once I have an idea of their “style” I will send them pretty little gifts. These don’t have to cost a lot but they have to be right. Something as simple as a fountain pen or a charming Deco desk clock gives just the right sense of being remembered.

My ladies tend to be emotionally pretty competent. That is one of the reasons they see me. They don’t want to lose emotional control. Which is a possibility if they go on real dates. It would be wrong to say my ladies, in general, are lonely; it would be more accurate to say that as they drove to the top of their fields they had to close off a fair number of possibilities and, now that they have arrived, they want to explore some of those possibilities.

A few of my ladies have suggested that they hire me on an exclusive basis. The money sounds great but, honestly, I don’t think it would work. Drinks, dinner and a frolic between the sheets is not an emotionally draining experience. An exclusive commitment would be and that is not at all what I want and, I suspect, not actually what my ladies want either.

I keep my business entirely private. No one knows that I am well paid to squire these often interesting and occasionally quite beautiful women around town. Well, obviously the ladies themselves and Jackie; but I like to keep my business quiet. The one downside is that a fair number of my clients, because of their business profiles, are covered in the gossip columns and online.

It turns out that my own activities as an artist, photographer and film maker are the perfect cover. I am well outside the corporate or legal or financial worlds which means I am non-competitive. But it makes perfect sense for an accomplished woman to be seen on the arm of a “young artist and man about town”. I make a point of taking interesting girls on non-professional dates to places I am known. My picture will be in the paper and my email will light up with my ladies kidding me about whether I’m getting ready to settle down.

As I get a bit older I am also going on more travel dates. Often as “arm candy” but also to provide a lady with a convenient out in awkward social or even sexual situations. Having a man along on a business trip can make it very clear to the other side that the lady is there strictly for business. I get to spend the day in the galleries and the shops and have lovely food and enjoy the best suites in great hotels.

The consenting adult thing is a bit different for a male escort in the sense that where a female escort can combine lube and a good attitude to get past any lack of sexual desire, a male escort cannot fall back on the spirit being willing but the flesh weak. Thank God for Viagra I say. The little blue pill, in relatively low doses, is more than sufficient to ensure that my clients are left in no doubt as to their physical allure. Which is often very important to them. At the same time, honing really excellent oral skills is a real asset.

What I think keeps my clients coming back is a deep sense of safety and security combined with a sense of fun and a lot of flirtation. One woman told me she used to have a really delightful interior decorator who was so much fun, albeit gay, that she kept a decorating project on the go pretty much full time for three years. It was hugely expensive and she was sexually climbing the walls, but at least she had a male friend she could enjoy. A guy who was not after her job or her clients or her body.

So, last point, making my ladies laugh and flirting with them is a huge part of my job. But the other side of my job is to let them feel safe and very comfortable exploring their own sexuality. My ladies may have been very successful but that has often come with a price. Sometimes that price is sexual inexperience, other times it is sexual experiences where they were uncomfortable, not in control.

It usually takes a couple of dates for a client to realize that my job is her pleasure. I am very good at my job and I often say to my clients that their only job is to lie back and enjoy. Or, if they find they are not in the mood, to send me to make them a sandwich.

I make a very good sandwich.