Escorting 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.

by Hannah Jay

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.

As long as there have been hotels there have been escorts going up to guest’s rooms. As long as the girls were discreet and nicely dressed no one blinks an eye. For all we know these girls are business acquaintances or friends and you don’t want to embarrass yourself or the hotel by suggesting that a girl is an escort. Plus, realistically, it is none of the hotel’s business if one of its guests wants some female companionship.

It is the hotel’s business if some gal comes wandering into the lobby with a skirt up to there and down to here, hooker boots and an attitude. Not because she is an escort, rather because she is a security risk. If you are a blatant hooker you are not going to get by the front desk unaccompanied, who knows where you will go in the hotel.

But I did notice that there were a few girls who I would see regularly. Nicely dressed. Usually with expensive shoes and sometimes with a really nice designer bag. Sometimes they would accompany a guest to his room, other times they would stop by the desk and ask for Mr. Smith on the house phone – which I learned was an excellent way to do a final check on a client. But the one thing they all had in common was that they were terrifically discreet. Yes they were glossy or a bit more glamourous than our run of the mill female guest, but they made sure they were perfectly put together.

We used to play a game on slow nights. “Escort or not”. A girl would go up to one of our guest’s rooms. How quickly would she return? If it was more than an hour but less than three, we said “Escort”. Not for any great reason, but that’s how we played.

One night, after an early shift, I went over to our very ritzy bar for a drink and saw one of “the girls” on her own. She nodded to me and smiled so I went over and joined her.

“I see you come in quite often.” I said pretty neutrally I thought.

“Nature of the business. I love this hotel. It’s always so clean.” she replied.

“And your business is?” I asked. Why not? I could always get up and leave.

“What do you think?” she said with a smile, “I entertain many of your gentlemen guests of an evening.”

On that basis we had a chat and, I have to admit, I was amazed. “Lucy”, not her real name of course, worked a day job full time and was entertaining in the evenings for spare cash. But what a lot of spare cash.

“1000 dollars plus tip. But I don’t watch the time. Sometimes I am there for twenty minutes, sometimes two hours; it works out in the end.”

Four nights a week, no more than two dates a night, usually just one. I am good at math but you didn’t need to be, Lucy was making $5000 a week minimum. Little wonder she was carrying a $3000 Prada bag and wearing Jimmy Choos. I was making, net, about $600 a week and was barely scraping by.

Lucy saw her date and excused herself. I went back to my white wine spritzer and began to run the numbers. In a month Lucy would make $20,000. Did she pay tax? Who knew and no one would if she was even a little clever about it.

This was huge for me. My hotel career was going just fine but it would be two years before I got a decent management job which paid more than a pittance. Plus, I had had an idea for the consulting business I now run. The fact was I could see where our hotel was missing revenue and I was pretty sure other hotels would run into the same problems. My idea of “embedding” in the front desk staff at various hotels made a lot of sense and I knew my own manager would be supportive if I went out on my own. The problem was how would I get by while I set up my business and hunted down customers. Lucy gave me a hint.

I had never really considered escorting. I mean I knew, or at least thought I knew what those girls were doing up in our rooms with their clients. But that is not the same as actually doing it. I got to work researching the heck out of the escorting business. Thank you internet. There was an awful lot to learn. Everything from escort advertising through to how best to screen clients to how to manage an escorting date. But there were also terrific online resources like Skipthegames.com for escorts.

The good news for my potentially budding career as an escort was that I have never been at all squeamish about sex. In fact, even before I was an escort I enjoyed sex a lot. And it turns out that the way I enjoy sex, lots of enthusiasm and a fair bit of my being in charge, is a great way to do those consenting adult activities which are at the heart of every escorting date. But there is a lot more to escorting than sex once you start looking at it.

One thing I realized right at the beginning was I wanted to keep my escorting life completely separate from the rest of my life. Which was a bit of a puzzle because I wanted to do outcalls to hotels and, working in the business, I knew that it would only be a matter of time before word got around about my escorting activities. Oddly enough, the solution to the problem arrived when I had to go to a different city, not too far away, for a week long training program. Basically I realized I was an hour by car away from a completely different world. In fact less than that because I actually lived about twenty minutes away from my own downtown right along the freeway towards the other city.

Problem solved. While I was on the training course I arranged a cell phone in the city I was going to work in. And I took a look at some of the better hotels where I thought I would meet my clients. I scouted the various escort advertising sites and made some decisions about how I was going to present myself.

While I was doing this “legwork” I also was trying to figure out how I could best open my consulting business while escorting. Which led to my second “Ah ha” moment. I realized that it would be too frantic to try and escort at the same time as I was doing what I needed to do to build up revenue for a hotel. So I wouldn’t. What I decided to do is escort for a month, then do a consulting contract, then do another month escorting. My contracts were planned to take roughly two months and I had two lined up if I decided to take the plunge.

I gave my notice at my hotel and my manager, who had actually referred my first consulting client, was great and said I was welcome back any time. It was nice to know. The day after I gave my notice I put up my first escorting ad.

Anyone who says that escorting is an easy business is kidding you. Like every other business there is a steep learning curve. My first mistake – of many – was to assume that if I put up an ad I would suddenly have escorting clients. My phone was so silent I tried calling myself just to make sure it was working. It was. The fact was my ad was not getting the response I needed. Why not?

As much as anything it was because I was much too vague. I was all about “dining companion” and “pampering” which was fine as far as it went; but I was naïve enough to think that, along with a slightly sexy picture, would be enough. So I worked on my ad copy and did another, much sexier picture. I got a couple of responses but they were really time wasters who wanted a bargain. It took a while for me to realize that I had to really make clear that I was catering to executives who wanted more than just the “GFE”. Eventually, a week later, I got my first serious response. He was staying in a great hotel and he checked out on my screening.

I put on pretty lingerie, stockings, a great skirt and a semi-sheer white silk blouse. My hair was nice, nails done, make up right for evening and condoms in my cute little clutch. I hoped in my car and drove off to meet my first escorting client. Forty five minutes down the expressway and right into hotel parking. I’d arranged to meet him in the very pleasant hotel bar and I was there right on time. I secured a nice, out of the way, table, sat down and waited. And waited. And waited. An hour later my phone chirped out a text. He was stuck in a meeting and would have to reschedule. Not how this was supposed to go at all, but live and learn.

He was my first, but sadly not last, no show. From then on I didn’t get on the road without a confirming text of email. Happily, a day later, at a different hotel, I had a really delightful, and very lucrative, encounter with a very nice lawyer in his early sixties. He was delighted to be my first client and tipped very generously. He also booked me for the following week. A regular I thought to myself as I drove down the nearly empty expressway home.

That first month I had nine dates after a slow start. Not a lot but more than enough to keep me solvent as I got ready to do my first consulting gig. My idea of escorting a month at a time took a bit of a hit when my lawyer friend called the second week of the next month. Fortunately my first consulting gig was in a suburb of my city so I was not really “on the road”. I made an instant, executive, decision that if they called direct and I could I would see regulars even when I was not officially escorting. Which was, I think, the right decision. What I did do during my months off was stop advertising.

I have been working this system for escorting for nearly four years and, honestly, I can’t imagine not escorting. I could because my consulting business is doing very well; but, realistically, even though I charge a lot for my services as a consultant, the money from escorting is just too good to give up. Plus, and this only occurred to me after I had been escorting for a year, there was no reason I couldn’t combine my escorting months with living in different cities. I was already doing the travel thing with my consulting business and AirBnB knew my credit card off by heart. So, once a year, in the winter, I advertise in places like Tampa or Phoenix or Miami where I can get some sun.

For me escorting is all about the money but that does not mean I don’t actually enjoy the work. As I gained a bit of experience I realized that the sort of men I was seeing really wanted the company of a sleek, well put together, younger woman but they also wanted to be very, very safe. Yes, hiring an escort was a luxury purchase for them; but they were actually very happy to pay a lot of money because they were pretty certain an expensive girl would be much safer. I aimed to please, I was very safe and very expensive.

The other thing I learned is that if you want to be expensive you have to look expensive. Which works in consulting too. My girl Lucy was not wrong carrying a Prada bag or wearing Jimmy Choos. A really good haircut is a must. So are great photographs taken by a professional photographer. The photos I took for my first ads looked like a girl taking her own photographs; the pictures I have on my ads now cost a fortune but they make me look like a movie star. If an escorting client is getting ready to pay top dollar he’ll scan around until he sees a girl who looks like she is worth that top dollar.

Final point: even if I stopped advertising tomorrow, which I won’t, I would still make sure I saw my regulars. I have about twenty men I see often. They understand that I take time off escorting so I can do my consulting but I make it really clear to them that I am available for them if it is at all possible. The reason is simple: those twenty guys pay my full rates four to six times a year. You do the math. Right there I have all the money I need. Keeping my regulars satisfied and interested is great fun. I send them little notes and, if they can receive pictures securely, the occasional naughty snapshot. These guys are clients but they have also become friends. I may stop escorting someday, but I will always have time for my friends.