For escorts, a change is as good as a break

No matter where a girl is on the great wheel of escorting – service provider to courtesan – at some point escorting is going to become a routine. A job. A chore. Now for some girls that is a positive relief. No more worrying about dates, no pressure because everything is predictable: for others it is a huge hint that they need to rethink the whole thing. Somewhere in between is a need to change things up even for a little while.

by Hannah Jay

At the same time, most escorts either cannot or don’t want to give up the delights of escorting cash. So, what to do? We talked to a few girls who have come up with novel ways of taking a break from their daily escorting routine without taking too big a hit in their wallets.


Where ever you live, inexpensive tickets for cruise ships, airfare included, litter the internet. A seven to ten day break in the sun or out of the heat of summer going to Alaska may be just what you need to get away from it all. At least it was for Lisa a 32 year old escort from the mid-West.

“I had had a crazy busy Christmas – lots of clients, lots of family stuff – and it was cold and windy and snowing in the third week of January. In my escorting business I find January and February are slow. Not dead, but slow. Just a few regulars and the occasional random caller.”

“I like to work and I like the income but I needed a break. I am pretty careful about money so I had more than enough to take a trip. I thought of Florida but, honestly, I am just not a beach girl. Too fair to really tan. I was surfing around the net and I kept seeing ads for seven day getaway cruises in the Caribbean.”

“I was really picky. I wanted a nice cabin, to myself, with at least a porthole. What I got was a last minute deal on a really lovely junior suite. I had to shift two regulars to make the sailing but they were sweet about it. So, I got my passport, my little roller suitcase, garment bag and an overnight bag and packed for an informal week of deck walking, great food, time in the gym and lots and lots of reading. On a whim, I packed a couple of mildly naughty dresses. I always wear pretty lingerie so that was not an issue. A couple of nice candles my favorite toy and four thick novels. I was set.”

“I really had not thought about working on the ship. If you google around you can find a few stories about girls who dated on their cruises, but not many. My plan was not to have a plan.”

“Quick flight to Miami and on to the ship. Here’s a tip, by the way, if you book a more expensive cabin, even if it is steeply discounted, the crew treats you like royalty. It’s just like in a hotel where a suite always gets you better treatment than a plain room. Now, my cabin was not terrifically big but it had a seating area and loads of cupboard space as well as a sweet little vanity. And it was all mine. I had my own room attendant and there was a pleasant small, library bar just around the corner where I could read, have an espresso or a light snack. I had a little balcony. Tiny but perfect.”

“I really had no idea what the situation on the ship would be and I was not in a rush to find out. I spent the afternoon exploring and then had a light supper and, as the ship sailed across the Caribbean put on a pretty nightie and tucked into the big, comfortable bed with my novel. I slept beautifully.”

“The next morning, after coffee, orange juice and a croissant delivered to my cabin, I went to the gym/spa for a couple of hours and then came back to dress for lunch. I’ve learned from other cruises that my particular ship was seen as a more formal, adult oriented ship. There was a handy guide to the various restaurants with a graphic from casual to dressy. I like pretty clothes and so tended towards the upper end of the scale. Which was comfortable and, as it turns out, lucrative, for me.

Most of the people on my ship were 50 and up. There were a lot of couples, quite a few older single women and very few older single men. There were also groups. I found myself seated for lunch with another single woman and two couples. None of us knew each other but soon became shipboard friends. Which was lovely. It also provided me with cover as I explored commercial possibilities.

There were a couple of quite upmarket bars on board. One was all about wine and the other was “land of the exotic rum drink with the parasol”. The early afternoon was ideal to sit with my book, a pretty, long but with “a slit up to there” skirt and sleeveless, semi sheer top complete with lacey, semi sheer, bra in a slightly contrasting colour. The ladies tended to be by the pool, in the spa or at the hairdressers and it was a matter of ten minutes before gentlemen found it necessary to sit near me, send over drinks or strike up conversations.

I evolved a rule on the spot that no arrangements would be made in these delightful locales. I had taken the precaution of setting up a page on my website – which looks very much like an interior decorator’s if you hit the home page – with the name of the cruise ship. Click on the link and put in “a safe email address” as I put it, and you would be directed to a charming page of shipboard delights.

My other rule was that I was on holiday: no more than one, or at most two, encounters a day and I wanted to be well paid for my time. Believe it or not I was booked solid two days out of port. Apparently salt air and holiday Viagra have a stimulating effect. Very nice men, perfectly delighted to spend quite a lot of money for a pleasant interlude while their wives were shopping or playing bingo or whatever. Shore excursions were the perfect time for a gentleman to enjoy me at his leisure but I was happy to accommodate gentlemen who had only an hour, or even half an hour, at their disposal. Most of my dates were in the afternoon but I had a few late night callers as well. Thank heavens for air conditioning. Fortunately I had quite a large bathroom. Which is not a given on a cruise ship.

I was, of course, very discrete. Because I had my little sitting room entertaining a gentleman caller was not in the least outrageous. And my stewardess, whom I tipped very well, made a point of leaving towels for two in my single room.

I have to say that it was one of the most relaxing vacations I have ever taken. Of course I came home with much more money than I left with. So much more that I decided to book a similar cruise a couple of months later.

It turns out that I am not the only escort to have discovered the delights of cruise ships. In fact I have been on cruises where there are two or three of us. But we’re big girls and there are plenty of men to go around. And we are, after all, on vacation.

I’ve never had any difficulty with the crew. In fact, as I am now a recognized cruise junkie, I am usually upgraded to one of the nicer cabins without asking. I’ve got to know a couple of the bar tenders on ships which I like and they are more than happy to refer customers. Tipping is an art in such situations and I make sure my hand is open.

Plus, along with a very safe, easy escorting existence, I manage to finish three or four good books a cruise. Something I can never seem to manage in the city. I come back refreshed, sun kissed and eager to get back to my regular escorting business.


“Of course I get burned out sometimes” said Jill a twenty seven year old brunette who escorts in San Francisco. “I’ve worked hard to build my escorting business over the last five years and, honestly, while I love my regulars, they can be pretty demanding. I try to be bright and bubbly and enthusiastic but that can be tough when, for safety, you try to only see guys over 40 and screen them hard. One sort of blends into another after a while. Plus I see almost all my clients at my “studio” which is just a tiny apartment close to downtown. I mean, banker, banker, lawyer, banker, lawyer is not much of a mix six days a week.”

“So, once in a while, I pull my ad, text my regulars and take off for a week or ten days. I have a cute little Miata which is fun to drive and really reliable. It’s really too small for the interstates but it is just right for all those old highways.”

“I pick a spot which is, say, a three day slow drive from the Bay Area. Then I pick two other spots going and two coming back. I like driving a circle. A good trip might be Sacramento then up to Boise Idaho and then over to Eugene and back down through Redding and then out to the coast.”

“I’ll put ads up a couple of weeks before I go and I will usually have dates booked in most of the cities I stop over in. Not a lot of dates. I don’t want a lot and if you are working from a hotel you need to be a bit careful.”

“Some escorts call this “touring” which, I guess, it is. But my ads are all about “Escort roadtrip” with dates for each of the cities. I like to do this in the spring and the fall. In the winter I will try to get away skiing or, if I can swing it, either down to LA or San Diego. Or, better still, Maui. But those are not great places to drive.

“If the weather co-operates I flip down the top on the Miata and drive the secondary roads. I like driving with spirit, not much past the speed limit, but really digging into the corners. There are stretches of highway which just make you forget anything but driving.”

“Safety is a big concern when you are on the road. I like the big old hotels downtown. The Citizen in Sacramento for example is just a big old place with a lot of character. I book under my own name and I am always nicely dressed when I check in. These days hotels, as long as you have a credit card, are not nosey. Because I usually drive off peak, I can often get a great deal and an upgrade.

I like to meet my road trip dates for a coffee or a drink or even dinner before I make the commitment of taking them back to my hotel. I will have screened them but when I am on the road I don’t have the certainty I have in San Francisco. Besides, I am not on the clock and I like to build a bit of a connection before the fun and frolics.

Getting out of town for a few days really clears my head. My escorting regulars are no longer boring, my nerves relax a bit and I’ve seen a bit of the country. All good.


“One of the biggest downsides of escorting is that you never really spend much time with your clients.” Helen, a thirty one year old escort in Minneapolis told me by Skype, “For some girls, me included, that is sometimes a bonus but month after month it begins to wear you down.”

“I’d thought of taking a break and I did for a couple of weeks, but that cash is seductive. Even with savings, and I have some, when you take a break your income goes to nothing. I didn’t want to get a straight job. But I did want to go to school to take a certificate program in web marketing. Six months. There was just no way I was willing to give up my escorting income for six months.”

“I was talking to one of my best clients, the regular of regulars, and he came up with a really brilliant solution. He said, “Look, you want to take a break. I get that and I think it is really smart to get some training. So, as the expression goes, why not go from retail to wholesale?”

“I asked him what he meant.”

“OK. Escorting retail means you are seeing a lot of different men. You have to advertise. You have to screen. You have to be available twelve or fourteen hours a day. That’s the retail business; but what if you only saw a very few men. Maybe three or four. In the old days a man might keep a mistress. Basically a girl who he paid an allowance to and who saw him exclusively.”

“You mean like a sugar baby.”

“Well sort of.” said my regular. “But here’s the thing: most men have a very hard time coming up with 5 or 10 thousand a month to keep a mistress. On the other hand, I spend at least $2000 a month seeing you. Find three more of me and you’d be set. Do you have any other really, really regular dates?”

“I had one. And I suggested the idea to him and, wonderfully, he said yes. Better still, he said that if I was serious he’d be willing to put $2500 a month into my school fund. Now my living expenses are not huge. Just rent and food and utilities. I am not extravagant but I like to have a really solid cushion. So I figures I needed one more patron. I put an ad up on a couple of escort advertising sites as well as in the local alternative paper. “Looking for a patron to help me complete my studies. Pretty, petite brunette. Mutual pleasure, enquire within.” I put it up with a very pretty picture which keep my face partially hidden. I was amazed at the response. Nearly eighty men were, apparently, eager to enjoy my company. I sorted them out and used basic escort screening techniques to feel safe. Once I quoted my allowance requirements I was down to six gentlemen and I picked two and promised the other four I would stay in touch.”

“Now I have a nearly perfect existence. I have my mornings to myself. Gym or yoga three days a week. A lot of time in front of my computer figuring out how <div> tags work. Then off to class four afternoons a week. I am done by four. I live a few blocks from campus so I usually walk home. Each of my patrons has an evening. Not time limits but I don’t let them sleep over. And, if they would like, I give them each an afternoon on a weekend. Which is also handy if they are out of town during the week.”

“Of course each likes to do different things: my regular of regulars, it turns out, is a huge movie fan. And he likes fairly interesting arty, indy films. So we’ll have a bite to eat, go to a movie and come back to the apartment. One of my other patrons prefers to stay in, sip good wine which he brings and have me serve him, more or less, naked for the entire evening. Another comes in right after he works out and I bathe him and massage him before adjourning to the bedroom. They are all nice men and they all really want the fun of having a much younger woman catering to their pleasure.

On the evenings one of my regular patrons is unable to make his appointment I will call one of the other men who I qualified. While this is a little closer to retail the reality is that I want to have a backup. Men can be so fickle and, while it hasn’t happened yet, I am sure one of my patrons will move on.

I am a month away from finishing the certificate. I’ve thought about going back to regular escorting when I have more time but, honestly, being a mistress to four very decent guys is almost as lucrative without any of the hassles you run into in retail escorting. No law enforcement, no no-shows; but, most of all, I am really connected with my patrons. I know them and they know me. There is a real connection. Which I find I like. A lot.