When you read about escorting there are lots of stories of girls who have become escorts because they have “had to”. The “had to escort” reasons really all come down to one thing: money. Or, more exactly, the absence of money. This is often referred to as “survival sex work” and is a situation very much to be avoided.
The other side of that coin is what I call “escorting by design”. Here a woman makes a conscious and un-coerced choice to escort. Escorting by design lets a woman enter the escorting market in her own way and at her own pace.
A lot of the sex trafficking, sex work-negative information out there suggests that escorting by design either does not happen at all or is very rare. However, my own conversations with escorts makes it clear that for some women, escorting is a positive, lucrative choice.
by Hannah Jay
“Of course I made a choice.” said Lily a twenty seven year old, beautifully dressed, brunette from Toronto. “I had finished a design degree at Ryerson University in Toronto and I had an internship with a design studio. I was all of twenty three and I’d done a little modelling in my teens.”
I am striking rather than pretty. Five nine and a half and I like to wear three or four inch heels. I didn’t make it as a model because, honestly, my figure is too curvy. I am a bit overdeveloped on top and I have a tiny back and a tiny waist with normal tall girl hips. If I want to, I can cause a bit of a sensation with a short skirt and a tight top. But that was not really my style.
My style was that I liked wealthy men. Which meant I kept the short skirts and tight tops for weekend fun times. Wealthy men prefer a much more conservative look. Which I was fine with. Pencil skirts, really crisp white blouses and well cut jackets. Oh, and coats. Toronto is a very cold city seven months a year.
Now, the problem with wealthy men is that they are constantly being hit on by girls like me who want their money. For many of those girls the way they get the money is by becoming the girlfriend and then, if they are really lucky, getting married. But there are two problems with that route. First, you never get any money as a girlfriend. You might get the occasional nice present and lots of dinners and travel; but no actual cash. Second, wealthy men look for different things in a wife than a girlfriend. So a lot of the girls I knew in that world were just kidding themselves.
OK, so I had figured out that much but it took me a while to put together the other side of the equation: these wealthy men were very, very wary. Why wouldn’t they be? The problem from their perspective was that while they enjoyed taking pretty girls out for dinner and then to bed, they were well aware those girls were “on the hunt” for nothing less than all their money. There was literally no limit.
Now I had next to no interest in marrying some investment banker, twenty years older than I was with a first wife hanging around draining his wallet. I wanted to be free to travel, build out my career, and really enjoy my twenties. After about two months of dating a few of the guys who hung out at some of the more expensive clubs and restaurants I realized I was missing something. Or, more exactly, there was something missing.
That something was a girl who wasn’t after all your money, who was a sure thing after dinner and who looked fabulous. A girl who didn’t care if you were married or engaged or seriously seeing someone. A girl who loved to celebrate your successes and was happy to hop on a plane to New York while you did business. And, most importantly, a girl who charged a lot but promised no drama, no demands and no hassles.
I was exactly that girl. The question was how to actually become this high end, high status, escort. Because I realized that an escort was exactly what I had described. I didn’t kid myself about it, I wanted men to pay me for my company instead of thinking a $300 dinner was going to get them into my bed. Add a zero and skip the dinner.
Which gave me the headline for my first ad. “Let’s Skip Dinner”. The ad went on to describe in my snobbiest tone why busy lawyers, bankers and financiers were much better off calling me for their evening’s entertainment. There was nothing explicit in my ad or on the website I whipped together. Just a few demure photographs and my number and the email I had set up for my escorting business.
I looked at the ads and the websites of some of the girls who were escorting at the high end in Toronto before I did my own and it was interesting. No one seemed to specialize. Or at least they were not nearly as specific as I wanted to be. The funny thing was that I wanted my escorting business to be very much like the dating life I was leading except way more lucrative.
Toronto is Canada’s financial center. It likes to think of itself as New York, but it is a much smaller, much clubbier, sort of place. At the same time, it is also a lot straighter laced. Ultimately, most of my clients either work for banks, insurance companies, pension funds or law firms and they can’t survive a lot of gossip. Especially not gossip about being seen with an escort.
So a lot of my escorting business planning was to make my business seamless. I had to be alluring but invisible in my advertising or on my website. It really helped to have the figure I do because I could put up a few lingerie shots with my face out of frame and the alluring part was taken care of. Having an apartment just on the edge of the financial district was helpful too as it mean I could see my clients very discretely. I had not picked the apartment for escorting, but the fact it was at the end of a short hallway in one of those buildings where you never have met you neighbours turned out to be perfect.
I was also a bit lucky because I had got the apartment when I finished my degree with the idea that I would get a nice two bedroom and, if I didn’t get the right job, have a roommate. If my escorting business worked I would not need the roommate. Two bedrooms and a large master bath with a powder room off the hall worked very well. I used the master bedroom as my working bedroom and actually used the second bedroom as my office and design space.
I had read a lot about escorting and I realized that what I was planning was a low volume, high fee service. I also realized that this sort of escorting business would take a while to grow. The real question was whether I could afford to wait. I have to admit I burnt up a credit card I had been saving for emergencies buying a really nice leather couch with matching club chairs for the living room.
I had a lot of striking black and white photographs which friends from design school had taken of me. Some of them were very sexy, others demure. The sexy ones I had blown up big and they went into the bedroom and the master bath, the more demure pictures hung in the soft light of the living and dining rooms.
I spent a bit of money at the Hudson’s Bay on sheets and towels on sale. My theory was that fresh sheets and towels were a must for an up-market escort and having a few sets was worth it. A few Riedel stemless wine glasses and couple of crystal vases from a second hand shop and I was ready to go.
Or at least I thought I was. It is one thing to plan your escorting career, quite another to answer that first phone call. I had read all about screening and I was pretty sure I knew the procedure. What I was not prepared for was a call at 3:00 in the afternoon from an obviously pumped guy who began with, “5:30, Library Bar, Royal York and then gave his name. Dress for dinner.” That was it.
Two minutes on Google and then Linked-In confirmed his identity as one of two guys with the same name who worked in the financial business. Then I looked at the number that came up on my phone and I could narrow it to the right firm. A broker. OK. I liked that I’d be meeting my first escort client in one of the nicest bars in the city. That was a positive. It was ten blocks from my apartment but it was a reasonably nice night and the subway was a block away.
Is there a way to mentally prepare for an escort date? I have no idea. What I do know is that a nice long bath and unhurried dressing is how I like to prepare for any date and that was just what I did. And I washed my hair which let me put a few curlers in and potter around in my robe. I had bought flowers earlier in the day and had a nice bottle of Petit Chablis I had been saving for a special occasion. This was a special occasion so I poured myself a nice big glass. Cheese which I plated before I sat down to do my make up. I didn’t do anything different with my make up. Smokey eye and my trademark Charlotte Tilbury Red Carpet Red lipstick with a light gloss to finish.
When I went out, if I was able to come home after work, I would usually wear a dress. Tonight was no different. I love beautiful lingerie and with my figure know that good, well made, lingerie is an investment. Since I was in my teens, if I am going to wear hose at all, they are always stockings so I have a few pairs on hand. Plus a selection of pretty garter belts. For this date, starting with cocktails meant a little black cocktail dress. Just below the knee in a pretty black jersey, it was discreet but dressy. I had several, some of them had plunge necklines but this one was a simple square neckline which was not revealing at all. It hung beautifully with the tailored full, black satin, slip I decided to wear. Black pumps with a reasonable three and a half inch heel. I wore a single, pretty, gold and black enamel bracelet and a black and gold chain belt at my hips. I don’t think I looked at all like an escort but I did look terrific. It was a five minute subway ride to the hotel and I was ready to go at five o’clock. I didn’t want to be early so I took a few minutes to just make sure the apartment sparkled. I checked to make sure condoms were in their box beside the bed. I put on a wonderful, vintage, long, black shearling coat. Just long enough for the dress. I had a wonderful, vintage, Lucile de Paris crocodile bag which matched the coat and complimented the dress. I was set.
Heading downtown on the Toronto subway I practically had a subway car to myself and I whizzed into Union Station across the street from the Royal York at 5:25. Perfect. I hate to be late but never want to be early. If I am meeting a man in a bar I want him waiting for me rather than vice versa. I threw my shoulders back and walked into the lobby of the hotel and on towards the bar. A man was sitting opposite the entrance and, as I walked up, stood up and said, “Lily? I’m…” And we were off. He was obviously a regular in the bar, calling our waiter to “his” table and ordering Kir Royal (7/8 good champagne, 1/8 crème de cassis – drink slowly, they go to your head).
He was brilliant about the money. He had an envelope with him in his breast pocket, when we had our drinks served and were comfortable, he leaned across the table and gave me the unsealed envelope. “I am not sure this is the right amount. It was not on your website and I forgot to ask this afternoon. Slip this in your bag and in a little while you might want to powder your nose and make sure it is about right for the evening.” Judging from the thickness of the envelope I was pretty certain it would be just fine.
We had a second Kir and then walked a block and a half to one of Toronto’s nicer upmarket steak and big Cabernet houses. Very masculine spot. All leather and wood and lots of testosterone oozing from the timbered ceiling. It was loud at the bar and I could see lots of my future clients taking a good look as the hat check girl came round to help me with my coat. “You don’t see shearling very often.” she said handing my client the coat check ticket. This restaurant was antediluvian. So much so that they actually had a “ladies” menu with smaller portions and no prices. I happen to like steak and was thrilled to discover that I could have a “man sized” tenderloin merely by asking. And yes, we did have a big Cabernet. Or, more accurately, I had a lovely glass and a half while my client enjoyed the lion’s share of the bottle.
Like most of my escorting clients, as it turned out, my first had made something of a killing in the market that day. I don’t think it was millions but it might have been. So his idea was to have a great dinner and then, well, me. Having counted the envelopes contents he was certainly willing to pay well for what he wanted. However, through dinner he was a perfect gentleman and I learned more than I actually ever wanted to know about put/call straddles and implied volatility. Which option strategy was, apparently, paying for my first escorting date.
We hopped a cab back to my apartment and it was still quite early. Just after ten. I put on a little jazz, took my bit of cheese and the Chablis out to the living room and, well, even if I had not had an envelope full of cash safely tucked away in my desk drawer, I probably would have slept with this guy.
It was interesting, though: somehow I thought that the consenting adult activities at the end of an escort date would be different than they were are the end of a regular date. They weren’t. I am a girl who likes a good time in bed and I am more than willing to make sure my partner has fun and will want to come back. That was all that was needed.
I must say he was impressed with my slip and even more impressed with the long black stockings and garter belt which he insisted I keep on throughout the festivities. And, perhaps, it was his willingness to insist on what he wanted which made this an escort encounter. Usually, men are so pleased to get a girl like me into bed that they pretty much do as they are told. I guess when a girl like me is an escort she does what her client tells her. Or, more exactly, begs her, to do.
So, all went well and, delightfully, he left me a very nice tip. I was done shortly after eleven and he promised to call again in a few weeks. As I ran a nice, scented, bubble bath I changed the sheets, made a note to find a laundry service and then I checked my messages, two new enquiries, my email, two enquiries there as well. I answered the emails and noted the call back details and then, the last of the Chablis in my glass, I sank into my tub.
That was it. I was an escort. Apparently quite a busy escort. Just in time for my internship to end. There was no job at the end but regular, interesting, freelance gigs.
Now my life has a sort of pattern. I get up fairly early and work on whatever design stuff I have as a freelance. By about one I am a bit stir crazy which is fine because I have either my gym, swimming or a yoga class from 1:30 to 2:45. I have to work out to keep my figure because most of my dates are dinners. Then home, message check and, if I have an escorting date that evening, the routine of a bath, dressing and so on.
When I first started escorting I took every date I was offered where the guy checked out. Linked-In is great because they are all on it. But now, a few years later, I am much more selective. My rates have gone up and I make plenty of money seeing four or five men a week.
The unexpected bonus from financial escorting? I get really good financial advice. Which has let me make quite a bit of money in the stock market. Put/call straddles? You bet. In fact I am studying to take my securities exams. In a couple of years I’ll be a broker.