Escorting your way to solvency

Writing this column for a while you begin to get a bit weary of the straight escort success stories. Lovely girls who have decided to capitalize on their looks for great money escorting are interesting but are they the reality?

When Angie got in touch we checked out her website and found a buxom blonde on the other side of thirty. The site was pretty similar to the escorting sites we’ve seen. Lots of quite nice pictures of a girl who is obviously not shy. But the copy was a little different.

I escort because I love the kindness of strangers

by Hannah Jay

Quoting a Streetcar Named Desire always gets our attention. So we arranged an interview and, a few days later, sat on Skype with a slightly disheveled looking woman who had a radiant smile.

“I am so sorry I look like the dog brought me in. When I booked our chat I thought I would have the morning off but an old friend wanted to drop by on his way to work and, well, he just left. I never turn down regulars. Not ever.”

“Yes, I do quote Blanche Dubois. You would be surprised how many men of a certain age “get it”. Escorting is a strange business and if you can find an edge you just have to take it. I learned that early on.”

“Early on I had no idea. No clue at all. The fact was I got left by a really nasty man with an apartment to pay for and a part time job and a bunch of debts, which were really his but which I co-signed. Sixty two thousand dollars. I was making about three hundred a week waiting tables in a cocktail lounge. One hundred salary, two hundred having an extra button undone and making nice with the customers. I’d worked the same sort of job since I was eighteen. I graduated high school and everything but there were no jobs except waitressing that I could do. Soon as I turned twenty one I started working at cocktail bars. Better tips, shorter hours. I worked a few different places.

But let’s face it. You are not going to make the money to even make minimum payments on $65,000. The guy and I almost made it because he drove a truck and that paid OK. But on the road he spent a ton of money. I only figured out what on a couple of years later. Hos at truck stops. But it didn’t matter because he left with no forwarding address and all the credit cards got cancelled for non-payment so I guess he paid cash. I had all the collection agencies on my ass and it wasn’t fun I can tell you.

So, one night I am working in the bar and a guy, big spender, big tipper, who I knew pretty well gets me to sit down at his table. It was a quiet night and he was very definitely my best, and very close to only, customer. I don’t like talking about my problems with customers. Bad for business as a cocktail waitress, worse as an escort. But I wasn’t an escort yet and he was a pal. I figured he might give me a bit of a tip. So I told him what I called my “tale of woe”. He listened. Then he said, “I have two hundred bucks and I was going to go from here and pick up one of the girls on Madison. But, if you want the job…”

He left it hanging.

I’ll tell you how green I was. I said, “What job?”

He laughed and said, “Well, for two hundred dollars I usually get a really good blow job or a nice long ride.”

I’ve been propositioned more times than I can count. Part of the cocktail waitress gig I guess. And guys had offered me money but I honestly don’t think they meant it. That fourth drink and all. But this guy was someone I knew. And I knew he was absolutely serious. I also knew I gave a really good blow job. It was the nasty man’s favorite thing.

“Where?” I asked not really knowing what to say.

“My car. I know some quiet spots where the cops never are. And I like it in my car.”

“Another drink?” I asked playing for a little time.

“Better not. I’m driving.” he said with a rather nice smile.

It was that smile which found me bobbing up and down with my blouse unbuttoned all the way and my bra looking more like a scarf. He was a gentleman and used a condom so it was all pretty simple. He had a cigarette when he was done and said.

“So that really was your first time for money. Bit of a waste if you ask me. You have a real talent. Way better than the Madison Street girls.”

I had no idea what he was talking about but I resolved there and then that Madison Street would play no role in my just begun escorting life. We made a date for a couple of weeks later when he was expecting a deal to close whatever that meant. Well, actually, it meant that he’d have more money and wanted me to give him the long ride in a motel which he would book. More money too.

So there it was. I’d done my first escort date. A car date. I decided I didn’t like car dates and other than this one guy who likes getting blow jobs in his car once in a while, since I started escorting I have not done another one. He asked me if I had a phone. Which I did but it was personal. “OK, here’s fifty bucks for a tip. Go get a phone and text me the number. Here’s mine.”

I got the phone and started looking around. $250 bucks for twenty minutes not very hard work seemed like it could dig me out of the hole I was in financially. But one guy was not enough was it? I got a cheap phone and I looked around and, eventually, found a couple of online places I could post a picture and my contact details. I took a selfie in my “best earning” push-up bra and my phone started ringing.

I was incredibly stupid and incredibly lucky. If a guy called I would make the date if he sounded sober – more or less – and was willing to wear a party hat. Which meant I was taking really dumb risks. But I was making bank. I didn’t do all that many dates but two hundred here and four hundred there adds up. A month in I had done fourteen dates and I had nearly $3000 to put against my debts. Which was great until I found out the next truth of escorting. Cash is not that easy to work with. I went to my bank and made a $1500 cash deposit and about a week later I made another $1500 deposit. When I made the second deposit a teller I had known for years waved me over.

“Angie, I don’t know where you are getting all this cash but the manager is looking at your account. A couple more cash deposits like this and he’ll close it. Money laundering.”

Well, there you go. They were fine when I deposited $200 in cash after a good night at the bar but more than a thousand and all the red lights had started flashing. Of course the debt collection agencies would, sometimes, take cash but it was a huge hassle because you actually had to go to their office. As it turned out, the one place which was happy to see cash was a cheque cashing place two blocks from my work. I could pay off my debts there for a fee. It was only a couple of bucks a transaction and that was great.

But that was not the same as turning my escorting money into a real income and starting to rebuild my credit score. I was more than a little screwed with my credit score and so I went to see a guy who was a debt counselor – and an escorting client. And a pretty smart guy.

First thing he said: “You don’t charge enough. You could make twice the money seeing two thirds the clients. But the problem is that you are charging the same as a lot of pretty skanky girls. Guys see that and figure you are an escort just like them and they’ll haggle with you. You need to start charging more. I mean, seriously, the biggest difference between a high priced escort and a regular escort is the high priced escort is confident enough to charge a high price. You try it.”

He also gave me a lot of pretty good advice about how to set up an online store and then buy from myself which let me move money up to the store, over to its bank account and then back into mine. Or something like that. The details were a bit fuzzy but I was able to set it up so that I could “process” several thousand dollars a month from cash to electronic funds and cheques which my own bank was happy to see.

He was right about raising my prices. I raised my hourly to four hundred and I actually got more escorting clients. I talked to them and most of them said that if I was priced at nearly double what the regular escorts were charging I had to be something special. I really wasn’t but I did start spending some money on clothes and hair and grooming and I began to look expensive. I was seeing guys in the better hotels now. I figured I had to look a whole lot better.

The thing is that when you are poor you look poor and you think poor. I mean I didn’t have “a look”. I had the clothes I wore cocktail waitressing and then a bunch of athletic wear – yoga pants and t-shirts I wore the rest of the time. Until I started escorting I just didn’t have any money to spend on anything but food and rent. My debt counselor put me on a program where the first $1000 I made escorting was for “business”. Advertising, clothes, hair, nails, personal grooming and, for the first time in my life, a gym membership at my local recreation center which had a pool. “It’s an investment.” said my debt counsellor and he was right. I did exercise cycle or a running machine three days a week, and I did light weights for toning as well. Two days a week I swam lengths. I started with one.

The escorting cash took my mind off my debt problem. If I did ten dates a month I was ok; but my ads worked pretty well and I found myself doing fifteen to twenty escorting out-calls a month. I got a lot smarter. I started screening my escorting clients and because I was not so desperate, if something didn’t check out, I would politely decline the date. I also put a line into my advertising saying “outcalls to executive hotels” which meant that a lot of people who looked at my ad would self-select. They would see that line and my prices and decide not to call from their dive of a motel.

I didn’t realize it at the time but by going a bit up market I was seriously reducing my law enforcement risks. The cops in my city spent eighty percent of their time on street prostitution. The girls on Madison Street and the rest of the time they organized so called sting operations where they would call girls who had ads up and invite them to one of the rat trap motels just off Madison. I am not saying they never went after the higher priced escorts, I know they did because they would, once in a while, bust an escorting agency. But I never worked for an agency. My escorting career sort of jumped over the whole agency game.

To escort at this level I had to look the part and the part was not even close to the booty shorts and tank tops you see girls wearing in the ads. I had to look expensive and, even before that, I had to sound expensive on the phone. A lot of my clients have told me that they made their decision to hire me because “I didn’t sound like the other girls.” I have a good but not great voice but I think what they are getting at is I don’t sound rushed. When I answer my phone I always start with the same words, “Hi, this is Angie. How are you?” It’s pretty simple but it gives my prospective client the chance to get the conversation going. I don’t talk prices or services on the phone, ever. And I like to meet my client in a public place. Usually the hotel bar.

There is a fine line between dressing to impress and looking a little sleazy. I avoid sleazy. Most of my dates are in the evenings, sometimes quite late, but I always make sure I am carrying a slim little leather portfolio case for cover as well as my really attractive and usefully large vintage bag. Everything I may need on the date – condoms, lube, a cute toy or two, a couple of old pairs of stockings for the many gentlemen who like to be tied up, even a compact soft suede flogger – is in my bag. I keep it zipped.

I always wear a skirt or dress. Stockings of course – all my gentlemen seem to like those and you can find beautiful old stockings on line or at consignment stores for quite reasonable prices. Three inch stiletto heels. Exactly the opposite from stripper heels. I like to wear a button up top and the only “sexy” thing I really do is have one extra button undone. Pretty, lacy lingerie, of course. Now that I know what’s out there and that it is all an expense for my escorting business, I buy wonderful, sexy, lacy bra and panty sets. It is a little indulgence and it pays for itself in tips.

Even with my escorting income it took nearly two years to pay off my debt. But my debt counsellor, who was delighted to take his fees in the form of a monthly freebie, was right: I could do it and I did. And then, one day, I made the last payment. It was done, all $65,000 plus interest.

Now, along with it being a huge relief not to have that debt, I also had improved my credit score a lot. I paid my bills on time, I had a credit card, two actually, I paid off regularly. I even had about ten thousand dollars in the bank plus, of course, about another ten hidden around my apartment in cash.

Decision time. I no longer had to work as an independent escort.

I thought about it for about an hour. I actually made one of those lists of pros and cons. The plus side was obviously money. But escorting also made me more focused, more disciplined. I was running a business. A successful business. On the con side there was law enforcement and the possibility of bad dates. I had had a couple of dates with guys I would not willingly see again. But they were not life threatening, just unpleasant. And that was before I raised my rates and started screening. Law enforcement did not seem to be a problem.

I finished my last freebie with my debt counsellor and asked him for his last advice. “Angie, you seem to like escorting and you are good at it. While it will mean I can’t afford you, I think you should raise your rates a little more, concentrate on longer dates and keep going. The fact you are even asking means you probably want to keep escorting. Otherwise you would not be asking your most regular customer.”

He was right. I did like escorting and not just for the money. I liked escorting because it gave me my independence. I set my own hours, saw only the men I wanted to.

Five years later here I am in a really nice apartment in a decent part of town. Five dollar cab ride from the hotels where I do out calls; but now my apartment is nice enough that I can entertain at home. I actually prefer doing escort dates in my apartment simply because I am more in control. It’s a two bedroom apartment and I use one bedroom for work and have my life in the other.

I’ve accumulated a whole bunch of pretty clothes – all consignment except my lingerie – and some really wonderful furniture I’ve found at auction. I have the hair and nail appointments weekly and now get facials as well. I have a certain “look” a lot of men like. Call it the “office sexpot” with slightly too tight blouses and skirts which show I work out hard. I don’t pretend to be “educated” on my escort dates, but I am friendly, easy to look at, and I like to ask a lot of questions and enjoy the answers.

80% of my clients are from out of town. But some of them are regulars who visit five or six times a year. Which I like. I like getting to know my escorting clients. As people you know? I suspect I will keep escorting for a few more years. I’m out of debt but I have some financial goals which only escorting is going to make possible. Which suits me.