Casual escorting done right

There are lots of ways for a girl to escort. Whether she operates her escorting business as an independent or works through an agency, every girl will run her escorting life according to her own priorities.

For some escorts it is all about making the most money fast. For others, keeping a balance between escorting and the rest of their lives takes priority. But we were amused to see an escort ad which took balance to an extreme.

“Busty redhead Ginger. I might be available. If I am you’ll love the experience. But I am usually busy. Try anyway.”

by Hannah Jay

To our not very great surprise Ginger was hard to reach. It took four emails and a few texts to line up a Skype call with Ginger who works in Boston. Just as her ad promised she had long, wavy, honey red hair and, just lounging in yoga pants and a t-shirt there was no question at all that she was busty. We mentioned that she was a hard girl to get.

“I am. Not deliberately but I have a lot going on in my life and escorting is great but it can drive you crazy if you let it. I did a lot of crazy stuff when I worked in New York in my early twenties. It was all agency work and I worked for a really big agency. They could and would book their girls from eight in the morning until four in the morning and if you were signed on you took the dates you were sent to. It was totally nuts but, to be fair, really, really remunerative. I made bank.

Redheads are always in demand and, honestly, at least half the male population is fixated on large breasts. My boobs are not actually that big, a D-cup; but I have a tiny torso. I wear a 34D bra off the rack but my actual band measurement is 32 and a half and I have half a dozen custom bras which actually fit.

The other thing men like, even when they are not aware of it, is a little thing called “hip spring”. What that means is that you have a small waist but decent sized hips. Again, it is something I am blessed with naturally and a few hours a week in the gym or swimming and my waist stays very small.

New York was lucrative but it was also insanely competitive. All those beautiful girls chasing after all these finance guys. Nuts. And, of course, the agency had steep fees so even when you were doing a date which cost your client $4000 you only saw $2000 if you were lucky. And don’t kid yourself, those big agencies are connected if you know what I mean, and if you think you are going to start building your own escorting business on the side you really quickly learn what a bad idea that would be.

But, more than the muscle, it was the constant hustle and crazy hours which made me decide to get out of New York. I’d originally gone to New York as an intern on a fashion business website, which was crazy in itself, and, unlike the girls I worked with who either had trust funds or rich parents, I was on my own. Hence escorting. I was the only girl they hired after the internship which was great but not very lucrative. But, like the internship, only three days a week. Which left my weekends and two days free for the escort hustle. I scanned the web looking for something else to do somewhere else than New York. And, a couple of years ago, a Boston area accessories, bags and lingerie site needed an editor and I interviewed for the job and got it.

OK, fast forward. Boston is a lot cheaper to live in than New York. Huge plus. I had some savings, actually, quite a few savings, from my New York years. I banked my tips religiously. Still do. The way I see escorting in my own life is as a source of a lot more money than I can earn editing a fashion site. I mean the site I work for pays OK and I am the third employee and I have a lot of options instead of actual money. We’ve grown to fourteen employees and I actually run a whole section of the site; but the cash money is still terrible.

When I moved to Boston I had decided that if I was going to escort again it would be as an independent. Escort rates in Boston, like the rest of the country, are much lower than in New York; but if I cut out the agency I actually ended up making more per date. How much more? I had to figure that out.

I also had to develop a new, not New York, escort persona. Who was “Ginger” going to be? What was her style? Who were her clients? When I first got into town and was looking for a place to stay permanently, I stayed in a cute little one bedroom AirBnB apartment. It was expensive and I didn’t want to touch my savings yet. So I signed up with an agency. I know, I said I wanted to be independent; but the advantage of working with an agency when you come to a new place is that you get all sorts of information. Everything from law enforcement tactics to bad dates lists are necessities for an escort and working for an agency is a quick way to get up to speed about a city.

New York is, no question, the financial center of the universe and the guys there make stupid money; but Boston has a lot of very old money, a lot of trusts and investment funds and a lot of men who simply prefer not to deal with the craziness which is New York. The escort agency I worked with in New York was like a modeling agency constantly pitching its girls for huge prices, the Boston escort agency was much more like a temp agency of the old school finding “situations” for reliable young ladies.

The agency was run by a woman who, I suspect, had relatives on the Mayflower. Miss Adison. She ran the agency with two equally pearls and twin set “bookers” from a rather stuffy office building in downtown Boston. I went in for an interview before I was “taken on the books”. Fortunately I had a reference from my New York agency. When I left there my main agent, hearing I was going to Boston, explained to me that the Boston agency was all about discretion. “If you pass the interview you’ll do well. But the interview is a bitch.”

Indeed the interview would have been a bitch had I been the sort of girl who used that sort of language; but, as I am not, the interview – replete with tea in china cups and the ever challenging scone. (Hint: A scone is first broken in half (not cut) and is eaten piece by piece with first a little butter and then a little jam spread on each piece just before it is eaten. The butter, jam and or cream is always placed on your plate before being spread on the scone. Scones are an excellent test of manners because there are so many ways to make mistakes.) I had, I think wisely, worn a pretty, mid calf, cotton skirt in a tiny grey check, a really rather loose white cotton shirt and a light grey linen jacket. It was late September and still warm but I wore stockings and a pair of black flats. I was trying for a look between business girl and “nicely taken care of” young wife. The only give away was a vintage Hermes black Kelly bag. I was curious as to Miss Adison’s reaction to the bag. It went perfectly with the outfit but, if you knew what you were looking at, was about five price points up from the rest of my clothes.

I needn’t have worried. As I was ushered into Miss Adison’s rather sleek, modern, office she held out her hand and then, looking at my Kelly, said, “I suspect we are going to get along wonderfully. I have that same bag in crocodile.” which was to say, “I like your $12,000 bag because I have the $40,000 version.” In any case I passed the interview. Not unexpectedly, Miss Adison, after tea, had me take off my skirt and shirt. “Real?” she said gesturing towards my breasts. “Yes, ma’am.” I said. “And are you a redhead below as well as above?” “Yes, ma’am. But well groomed.”

I was put on the books. Unlike New York, Miss Adison had no objection to my working independently. Or, for that matter, taking bookings directly from regulars. “Not at all dear. The fact is that every escort I have ever known takes side bookings. However, what I would like you to do is pay us a 15% referral fee on subsequent dates with clients we have sent you. And, with new clients, we are happy to do your screening for you for a simple 15%. And, of course, once one of your gentlemen is in our system, should he make a date with one of our other girls you will receive a 15% referral fee. It is often quite a nice little income over the years.”

The one thing which we did agree upon was that I would be on the agency books as a “casual”. What this meant was that I could book on when I had time but a minimum of one evening a week. As a casual I paid a little more commission per escorting date but my time was pretty much my own. As Miss Adison’s commission structure was 65/35 compared to the New York 50/50 I was more than happy to give up 5% for my freedom.

My one night a week, which was and is Thursday, usually had one and sometimes two dates. Entirely outcalls and all to the nicer downtown hotels. Miss Adison had been running her escort business for years and the hotels were actually happy to accommodate her girls because they were always nicely dressed, polite and completely undramatic. One hint of trouble and a girl would lose Miss Adison and, in Boston, that was not a good thing.

I started running my little ad when I had found a pleasant, if cozy, two bedroom apartment in one of the nicer neighbourhoods near downtown. In fact, Miss Adison had recommended the building as, relatively, escort friendly. “Lovely high ceilings, pre-War construction which means thick walls. Nice neighbourhood, parking. The owner is a friend.” But more than a little expensive. So up went my ad.

My job was good because I only had to be in the office three full days a week. But they were full days, start at eight leave whenever the job was done which was usually eight or even ten in the evening. So those days were out for escorting. Thursday I had my regular engagement with Miss Adison’s escorting agency and I used Thursday to take care of things like hair appointments, an hour and a half at the gym, just the routine things. That left Friday and the weekend.

For the dates I got from my ads I preferred to do them incall. But, truth to tell, I was also very busy on all three days. The company I worked with was willing to pay for classes in things like web design and SEO so I took advantage of that. I also liked to swim a couple of days a week. I had made a few friends and we liked to go out either Friday or Saturday night.

My ad got lots of calls and emails. The “busty redhead” thing is always good for an escort. I had a little business smartphone – well encrypted I might add – but I tended to leave it off a lot. I’d realized in New York that doing a lot of escorting dates was incredibly stressful for me. Other girls have no problem; I found it difficult. So, rather than making myself crazy, I took a really casual approach.

A lot of girls in the escorting business don’t like extended phone calls or emails, I am exactly the opposite. I like to talk to potential clients. Connect with them on the phone. Of course I screen, or, actually, I have Miss Adison screen for her percentage. But my screening is not screening in the conventional escorting sense. It is screening to see if I will be able to relate to my potential date. I hate dates where the guy just wants to get down to the consenting adults activity. I charge a lot for my dates but I don’t watch the clock.

Miss Adison very much approves of my attitude and how I present myself. I have a certain, elegant, casual way of dressing. Mainly skirts for day, dresses for evening. Nothing exaggerated. With my figure I can wear a plain black knit dress with a very demure neckline and still turn heads when I walk into a room. Because of my job I have a lot of access to pretty, modern, lingerie and great things like Hermés bracelets. I can buy it all either wholesale or, often, as a sample which is even cheaper. I wish we did shoes but I have to buy those myself. I leave the towering Louboutins for the trampier escorts and sugar babies. I like a nice heel in the evening but during the day I prefer flats. I am tall enough that I really don’t need heels for day.

I think there is nothing sexier than comfortable. If I am doing an outcall escorting date I will always dress down. What I am wearing underneath my pretty, very conservative, dress is for my client to discover later in the evening; but when we meet in the hotel bar or a restaurant I want him to be able to plausibly introduce me as a business associate if we run into someone he knows. Miss Adison believes that, at the higher end, an escort has a duty to look like a lady and I agree with her.

I had really thought, after New York, that I would be a pure independent escort in Boston but the fact was Miss Adison made the whole casual escorting concept really workable. Miss Adison’s bookers are brilliant at screening and, often, they already have my client in their system which means I am good to go in five minutes. Such a luxury.

I see, perhaps two or three independent dates a week at my apartment which is really all I need or want to see. Where possible I like to see my clients around cocktail hour or in the early evening. I will do an out call escorting date for Miss Adison later on a Thursday but prefer not to. I prefer to see older men, ideally fifty plus because they are usually much more confident and know exactly what they enjoy.

“Ginger” – a name I have been called, like every red head, since I was a little girl – occupies a specific place in my life. My escorting persona can be tucked away when I am at my job. I don’t even take my escort phone. At the same time, Ginger and I share a dress sense in common although I am a little more fashion forward than my escorting other side: Miss Adison’s influence.

I know I go on about Miss Adison but I wish every escort was lucky enough to have this sort of positive female role model in their lives. Ms. Adison – no one knows her first name – makes it a point to get to know her protégées. She will come to tea from time to time and is filled with good advice. “Escorting is not forever, dear.” she said when she told me to start banking at least half of what I made.

When I had worked for her for nearly a year she called me out of the blue on a snowy February day and said, “Could you get a couple of days off your day job?” I asked why and all she would say is that I needed a vacation. I did too. And I could get a couple of days off. It turned out that a long standing and very wealthy client of hers wanted a bit of company in Barbados: fly in, stay a couple of villas over from where the old rogue was vacationing with his family and be available. Expenses paid, large tip, five days in the sun. I only saw Miss Adison’s client twice but I made sure he had a wonderful time. The perks of casual escorting.

The other thing which Miss Adison has told me about escorting is that the girls who succeed realize early on that the business is not all about the sex. “Men like to pretend they hire escorts for sex. To get something which they are not getting at home. And they are half right. They are hiring a girl to get something they do not get at home: enthusiasm, permission, excitement, variety. Escorts are a wife’s best friend if she is wise enough to ignore the signs her husband may be seeing someone from time to time.”

I think Miss Adison is right. Certainly my casual escorting dates are simply fun for the men I see. No drama, no threat to their marriage or their job; just a few hours with a girl who pays close attention to what they say and what they want.

And, of course, for me casual escorting is an opportunity to make quite a lot of money safely and easily: what not to like?