Modern Mistress

by Hannah Jay

  Never underestimate the allure of a polite, respectful girl asking a man to return and have her again. Especially, when she is wearing little more than a transparent robe. Done well, the little ceremony of leaving will remind a mistress’s patron that he wants to come back.

  For comfort and conversation. Like Joni says.

  Chapter 16| Mistress Style: Travelling Companion: Girl on the Go

  “I’m not really an elite girl.” Sam told us over Skype, “I’m not super model pretty or super busty or anything. Which I think my clients like. But I don’t think my patrons are exactly looking for super models. I mean some of my clients could certainly afford super deluxe escorts and I know some have tried those sorts of girls; but they come back to me because I am offering a lot more than what’s between the sheets.”

  “I’d been doing conventional escorting through an agency for a couple of months and, truth to tell, I wasn’t loving it. It all seemed so impersonal.”

  We had found Sam through an ad on an escort site which was very different indeed.

  “Travelling companion!

  Elegant, educated young lady is looking to expand her horizons and yours. Overnight or around the world, I live to travel and I am very good at it. Business or pleasure, travel can be stressful. Let me make all your arrangements. Bespoke trips, mutually beneficial arrangements.”

  “It is deliberately vague.” said Sam. “I advertise on a couple of escort sites but I also have a full website and social media accounts which are equally vague. Because a few years ago one of my first clients explained to me what I was offering.”

  “We were sitting in a pretty little seaside café in Victoria up in Canada. We’d taken a ferry from Seattle and were waiting to check into this amazing old pile of a hotel, The Empress, where I had found a fabulous off season deal on a suite, and we wanted to have a bit of a walk. I’d arranged for our bags to be sent to the hotel and we’d wandered down the waterfront of Victoria’s Inner Harbour.

  “My patron brought our coffee to the table and without any preliminaries said, “Do you know what you’re actually selling?” I said that I thought I did but would be interested in hearing what he thought. He was off.

  “You’re what, twenty five?” (I was 22 at the time but was not going to contradict him.) “I’m going to be fifty next year. I have a bunch of the toys – you like my Porsche – and I have a very nice, rather expensive, ex and a couple of kids who I see often. And I have a great business. Which I own so I can expense items like this trip up to Canada to look at a new market. So, all that and a lot more. Since the divorce I’ve had friend set me up with dates and a couple of guys I know like to go to places in Seattle where it is pretty easy to meet women. Which is all great. But the women I meet are usually in their thirties, one marriage, with or without kids, down and very hard-nosed. They want “serious” by the third date. I don’t.”

  “What I want is some fun. No expectations. No hassles, no drama. Which is why I was looking in the escort ads. Now, escorts are great. To a point. But you know and they know that it’s business. And so is this of course. A weekend away. With a pretty girl. But with all the business left behind us.”

  “Sam, what you’re selling is illusion. The pleasure of a travelling companion without any of the baggage which normally is dragged along on a trip.” My client was, I thought, telling me much more about what he was buying than what I was selling but it didn’t matter because, to be a successful mistress, you need to have a much more than sex to sell.”

  “I kept running my ad and I thought about how I could make the illusion all the more real. My actual business is to travel with my clients on the Westcoast and into the various ski resorts. Usually two or three nights but I will make exceptions for regular clients. Other than Canada, I stay in the US. Again, with exceptions for regulars.”

  “What I am offering is a whole package of services. I take the whole “companion” idea seriously. My clients want a “get away” and that should be a smooth, easy, relaxing time. And, of course, travel itself, with the airport lineups, crowded planes, lost hotel reservations, crazy cab drivers, crappy rental cars, bad food and money rolling out the door is incredibly stressful. A lot of my clients travel on business and they hate it. Part of the reason why they hate travel is because they don’t have me to organize their trips”

  “Travelling for pleasure is, or should be, entirely different from the heart attack inducing world of business travel. First off, you don’t have to be anywhere are a certain time. Or, more accurately, the world will not end if you are twenty minutes late for your dinner reservation. There are a lot of things which, if you do your research, can turn high stress into total relaxation. And, if you are a bit flexible, you can find amazing deals for transportation, rooms, events, flights which actually make a huge difference to the money stress of the trip.”

  “It’s funny. Most of my clients really do not have to worry about a few hundred dollars in hotel expenses. Realistically, if they can afford my fees, they can certainly afford the best room in the house. But, weirdly, on the road a guy who makes million dollar purchase decisions in five minutes will get bent out of shape wondering whether to book a room or a suite and, if a suite, then which suite. I take care of all of that.”

  “When a client calls me, and after I have thoroughly screened him, I spend a bit of time – usually by email – chatting about what he likes to do, where he would like to go, where he has been. I get an idea of his budget. If we are getting along I’ll suggest that I send him a couple of sample itineraries.”

  “I like to go to places I have not been, but I am also an efficient girl and I will usually send three different itineraries for three different destinations or “trips”. Two of them I will have done myself previously and one will be new to both of us. For new clients I prefer to have a home base in a city fairly close to where I live. Oh, you noticed that I don’t mention where I am based. Well, it is something of a secret but if you think Oregon you will not be wrong. I know the I-5 just a little too well. I also pretty much know the exact times the commuter planes run to Seattle, San Francisco, Los Angeles and Denver.

  I think nothing of hoping a plane to meet a patron for a couple of hours before a trip. He pays the fare but I am happy to invest the time. It also lets us get the business arrangements either completed or partially completed before we meet for our trip.

  A lot of my success as a travel companion is about creating the situations in which “chemistry” – whatever it is that brings two people closer together has a chance of happening. It is a fine balance. I can see why girls who escort like to keep a professional distance; but I am not going on a two hour date or even an evening with dinner. I am going on a trip and for my patron to have fun I need to really engage with him. Think “acquaintances with benefits” at the start of the trip. Almost always friends at the end.

  Having an itinerary is huge part of the whole thing. I like to try – for a weekend away – to get to our destination fairly early on the Friday. Most of my clients have no trouble at all leaving their office at noon and, if that works, I arrange to pick them up somewhere they are comfortable. If possible, I prefer not to fly to the destination. Obviously, if your client lives in Seattle and wants to go to San Diego there is going to be a plane involved. But an hour or two in a car or a ferry ride can always be pleasant. Here’s a hint – for much less than it will cost for two to fly business class you can usually arrange to have a lovely old Rolls or big Lincoln drive you a couple of hundred miles. A good chauffeur is discreet and there is no end of adult entertainment fun to be had teasing in the back of a big car. Alternatively, I’ll often have clients who would like nothing better than to take their pretty sports cars on a drive other than the morning commute.

  No matter what, I like to make sure we are at our destination at least two hours before our dinner reservation. I also like to make sure that I have a confirmed suite. Now, there is much to be said for grand downtown hotels and I love the l
uxury and the room service; but there are much better deals to be had renting a really lux condo for the weekend. And, yes I am a huge fan of Airbnb.com.

  The most important thing is “no hassles”. I’ve actually found that renting a fabulous downtown loft can turn out to be easier than going through the craziness of a big hotel. And, of course, it is much more private. It does mean having to do a bit more planning and prep. But most of the lofts I have rented for trips come equipped. And they usually have a great internet connection and things like an espresso machine. Bring the champagne and the little treats and you’re set. Plus, and this is key, they are usually a lot bigger than most hotel suites and have at least two bathrooms. No small thing when you are spending the weekend with a comparative stranger.

  “As my early client pointed out, what I am really offering is a few days with a pretty young girl who is paying close attention to all her client’s needs. But a lot of those needs have much more to do with having a companion than a sexual partner. After all, even the most eager man, with more than a little Viagra, will exhaust himself after a couple of rounds. So from where I sit, it is the intimacy and fun of the moment rather than the sheer quantity of adult activity which creates the best memories.”

  “Which is not to say that I don’t pack pretty dresses and sultry lingerie. Of course I do. Part of the mistressy element of the trip. And delicious sheer nighties and silk chemises. Because, if I do one thing very well indeed, it is tease.”

  “One of my clients told me that what he had really enjoyed the first time we travelled together was that I was actually playing quite “hard to get” for most of the trip while, at the same time, being sexually suggestive, as he put it, in a way that what he called “regular” girls just aren’t. I think he is on to something. I have a couple of girlfriends who know what I do on weekends and they maintain that they just couldn’t fake being interested in a guy for a whole weekend. Neither could I.”

  “What my client and my girlfriends were really getting at is a particular thing about how many women deal with sexuality. On my travel dates I play the good, bad girl. To all outward appearances, I dress, walk, speak and have the expectations of a well brought up young lady. But, with a bit of privacy, my client may see my bra peek out of my blouse and, very possibly because I like very low cut bras, my nipple will be on display. For his eyes only. You get the idea. My travelling persona is a very sexual, very brazen young girl who, nonetheless is not going to just rush into bed with the man she’s travelling with.”

  “To really work well my trips need the illusion of erotic tension. My client needs to have a faint sense in the back of his mind that he might not enjoy my favours later in the evening while, at the very same time, he needs to know that I am just dying to end up in bed with him. And I am ruthless in pursuit of that tension. I’ll shoo my client out of the suite or the condo while I change for dinner. I never let him see me naked – not that I have anything to hide but rather because I read somewhere that French women never let their husbands see them naked and it struck me as a very good idea. I’ll demand he run out and get me flowers. I’ll arrange to have him pick me up in a bar as if we are strangers.”

  “Most of all, for the entire weekend everything from our itinerary, the sights we see, our activities, where we eat and drink, our accommodations and our bedtime are all up to me. If I do my job right my client will have spent three days without having to make a single decision about anything. Plus, he’ll be in a state of some erotic excitement for most of those three days.”

  “As I mentioned I advertise in the escort sections of a couple of websites. But I also run ads in print media which read much the same way. My marketing is all designed to get potential clients to my website. When I started out I had a pretty standard website with a small gallery and my rates and my availabilities. But when I came up with the travelling idea – inspired by some of the “travel dating” sites which are out there - I changed the whole look. I wanted clients to get that the “sexy” end was just one part of what I was offering. Same with my social media. I take selfies and have my clients photograph me in the places we go and in the suites or lofts we’re staying in. Modest for Instagram and Facebook, a little naughtier for Twitter.”

  “In the winter I usually have five or six “ski dates”. These are wonderful because if you are in Vail or Sun Valley or at Whistler you pretty much know what you are going to be doing during the day. I grew up on skis so it is no big thing to ski 100,000 vertical feet on Blackcomb, have a fabulous dinner in the Village and fall into bed after a little quality adult time in front of the fireplace.”

  “This is very different from escorting. No worries about law enforcement. No hassles at hotels. Just the occasional eyebrow raised when I check in with a man who is thirty five years older. Which I am fine with. But most of the time, if we’re in a hotel, we get fabulous service because we’re in a great suite. Hotels like that.”

  “The nicest part about being a travel companion is I really do have a lot of time for my clients. I get to know them. Of course, if you treat your clients well they will want to see you again. I have half a dozen regulars who I am totally comfortable with. With those clients a week on Maui or a few days in New York is possible and fun. One of my regulars wants to do the whole “spring time in Paris” thing next year which I am really looking forward to.”

  “One other thing about the whole travel companion business is that I don’t worry about keeping what I am doing on the weekends a big secret. Sure, I don’t advertise under my own name; but if you are booking tickets and crossing borders your name is going to be out there. But what I actually do on my trips and the fact that there is a business arrangement is the only part I make any attempt to conceal. Otherwise I am pretty open. I meet nice men who like to go on trips…And I go.”

  Chapter 17 | How Not to Get Caught: A Primer for Men

  Some men really should not be allowed out the door without a minder. The sheer folly which leads to men getting caught keeping a mistress is astonishing. The fact that they are visiting a mistress is entirely up to them; but no matter how you look at it, keeping a mistress counts as cheating on your wife or girlfriend unless you have her permission and, even then, watch out.

  Getting caught cheating - whether with the lovely woman down the street or a mistress, drops a man into a heap of trouble. It can put you on the fast track to divorce with the 50% asset stripping and general expense and overall pain. From the wife’s perspective, cheating with a mistress may or may not be as bad as ending up in bed with your secretary. But let’s leave that for later.

  While keeping a mistress may be the official “crime”, a wife is going to be just as angry at the fact that you were disrespectful enough that she found out about it. In most cases the wife or girlfriend was not actually looking to find out or snooping; she’s found out about your mistress because you were careless enough to let her. And that is deeply insulting. That a man keeps a mistress is one thing, that he lacks the respect for his wife to cover his tracks, is quite another.

  Let’s start with the basics:

  If you are married or have a steady girlfriend it is a good idea to assume that she is paying attention. She notices things. She has learned your patterns, what you do on Tuesday night.

  She knows what you smell like.

  If you arrive home two hours late and freshly showered she’ll notice. “Mistress” might not be her first thought, but the seed of suspicion will be sown.

  What creates suspicion can be pretty minimal: unexplained absences, a change of routine, a change in attitude, being short of money, dressing a bit better, being more attentive, being less attentive. In each case, change triggers suspicion.

  Suspicion, in turn, leads to alertness and that usually means your wife or girlfriend will be looking for signs and evidence. Evidence can be pretty much anything. The obvious – an unexplained card or telephone number in that little pile of stuff which comes out of your pockets at the end of the day. A quick
look at the numbers dialed on your cell phone. Or a look at the browser history on your computer.

  As well, calls to where you say you are going to be to remind you to pick up some milk on the way home are quick and easy. If you are not where you say you are going to be it is not conclusive evidence but it is uncomfortable making.

  There is no recognized point where you are “caught”. It will vary from woman to woman but the point is that at some point she will have assembled enough evidence, circumstantial or otherwise, which will lead to a confrontation which you will not be able to win. Which is exactly what you do not want because if things get to the confrontation stage, your mistress visits are the least of your worries.

  An Ounce of Prevention

  If you are in a relationship but want to keep a mistress, you need to have a plan long before you pay your first visit.

  The first essential is to develop a routine which has fixed, specific, gaps in it where you are both not at home and off your cell. Something which is innocent and, ideally, solitary, and most importantly, true.

  An almost perfect routine is a twice a week swim. Actually going and swimming lengths for an hour and a half twice a week means that you have eight opportunities to visit your mistress every month. It explains why you will look freshly showered coming home from a visit and it means you are off your cell for a minimum of two to two and half hours. If you visit your mistress four times a month it will also have the benefit of sending your fitness level through the roof. Going for a long run and then to the gym will work as well.

  The key thing is to establish the pattern so that your wife fully expects you to be at the pool or the gym a couple of nights a week. Your visits to your mistress don’t raise suspicion because you are expected to be absent.