Dear Ms Jay,

I have a small escorting business which is more of a sideline. I have a good job as a web designer but the extra income from escorting is very welcome.

I'd like to move my escorting business up market a bit. Nothing too high-end, I am not exactly a model, just a bit more exclusive. Right now I mainly do in-calls. I wondered if it would make sense to do some out-calls and, if so, how I can find the right clientele.

Out-calls are certainly an option to consider. You don't have to limit yourself to one or the other. This shift will expand your client base. Just be aware that you will be spending time and money getting to and from your appointments. Increased time and transportation costs mean you must charge more for each escort booking. Factor in your circumstances: do you own a car? Or are there hotels easy for you to get to by public transit or cab? Since you mentioned that you wish to offer a more exclusive escort service, I assume you are thinking of the out of town businessman client. Structure your advertising to target this market. Also, you don't need to necessarily look like a model to move upscale, but you better be extremely well-groomed, well-dressed, and with a polished personality to match. Good luck!

Dear Miss Jay,

My boyfriend is getting suspicious. I have a very lucrative escorting business which I run from my apartment. Lots of regulars and great tips. I also have a wonderful boyfriend who I've been seeing for nearly a year. He thinks I am an interior designer – which I am but it is not my main income. I've been very careful but he is beginning to wonder why I have so many nights a week I can't see him. What to do?

Ah, yes, the suspicious boyfriend. Always a tricky problem for an escort. Well, there are a few courses of action you could take.

Firstly, you could simply tell him the truth. Is that an option? You have known him for a year, so you must be the judge on this one. Would he be accepting of your escorting, or would it destroy your relationship? Since you describe him as "wonderful", you obviously don't want to lose him. However, a little sideline secret is not going to get any less hurtful the longer it goes on, and there is the ever-increasing risk that he is going to discover it on his own. Since trust is a large measure of any coupling, this deception might get harder for you to handle. (One thing to remember, there are men who will actually find your escorting a bit of a turn on. Is he one of them? You might be able to find out simply by bringing up escorting in general in conversation and see his reaction.)

So, secondly, if you decide you can't tell him the truth and you want to continue escorting because it is lucrative, you could just carry on—ie. continue to lie about what you are really up to. Risky, but since you haven't told me how you feel about the situation, a little soul-searching is in order on this score. Also, do you have a time-frame or a goal that you have set for your escorting business—you will continue until you reach a certain sum? or until your design career is stable and generating sufficient income? Or do you even have a plan? If you don't get one. Fast.

Is money the sole motive for escorting? If so, and you feel your relationship is more important than the extra dollars, your third move could involve dropping the sideline business and concentrating on accelerating your interior design career. You would have to adapt to having less money initially, or find a way to replace it more legitimately (a night job; turn a hobby into a home-based business to supplement your wages). Your boyfriend would no longer have a reason to be suspicious. You might be even less available to him, but at least he would know where you were and what you were doing.

And in fourth place, because it is not a great alternative but it is a possibility, you could drop the boyfriend. Since you really like/love him, (and he continues to be wonderful), go for any of the above, not this one. This is not going to make you happy. Or him.

Whatever you choose to do, don't make a hasty decision. Be smart and brave. And let me know how it goes.

Dear Miss Jay,

One of my regular escorting clients would like me to join he and his wife for a threesome. I have two problems with this: first, he wants to "surprise" her – which I think is a terrible idea. Second, even if we could get past the surprise, I am not at all "into girls". In fact I wouldn't know where to start.

You have already raised two objections to the mere idea. This should tell you something. Intuition should always be listened to. Just because you are an escort, doesn't mean you have to do everything. My advice is to decline, and just keep your client as one of your satisfied regulars. If your client is determined to proceed even without you, you might recommend another escort who would be willing to take this on, (after checking with her first, of course). Frankly, I think your client is taking a risky step here, but you, not he, has asked for my opinion.

All of that said, there is always an argument – often involving money – for new experiences. But for this one to work you need to take charge and immediately explain to him that "surprise" is not the way to do this. In fact it is just the wrong way to do it. Instead, suggest that if he really wants this to happen it needs to be in the nature of a seduction rather than a shock.

Dinner and then back to their hotel room or home will be a lot easier to accomplish. But that will require set up and preparation. Will his wife know you are an escort and if so will she know that he has seen you before? You can guess that this will raise issues on its own so you have to have a great story.

Skipping ahead, not being "into girls" is not as much of a barrier as it appears. Your client may have all sorts of fantasies about delightful girls enjoying each other as well as him; but those fantasies can stay in the bottle. When men think of threesomes they tend to place themselves in the middle as the center of attention. Having two women at the same time is a pretty common fantasy and is not at all difficult to do. The main issues are a matter of who is where when and, with a sense of humour, these gymnastic details will resolve themselves.

Dear Miss Jay,

I know you don't like the word Sugar Daddy but I was wondering how I might find one. I'd like to reduce my escorting activities and concentrate on keeping one man very grateful and satisfied.

That seems like a splendid plan! There is much to be said for this type of arrangement. It has great advantages on both sides. But finding a patron who you could genuinely enjoy spending time with for an extended time, is not always an easy enterprise. Advertising is always a good first step. Place a post, but not an escort post, here is one such approach:

Beautiful, elegant woman seeking to be the mistress to one exceptional man. Offering pleasure, intimacy, and discretion. Able to travel, loves to laugh, adores the finer things in life. If you do too, lets chat over a glass of champagne.

If possible, you should also respond to posts seeking such a relationship. Here you already have a like-minded man trying to find what you are after. In both instances, choose someone whose expectations match up with yours (or close enough to make a few compromises for). Here are a few considerations when mulling over your potential S.D.

• Likely best if he lives in the same city, but this could also be feasible if he travels regularly enough to make it work or is willing to fly you to him at whim. Are you willing to relocate in the future?
• Seems to have the financial means to keep you. Naturally, you are going on trust and instinct here, but once you agree on financial terms, money should change hands before you do anything.
• Does he have some interests that interest you, too? Are you compatible in and out of bed? Do you have things you could do, talk about? Do you find him interesting? Are you comfortable in his company? And do you intrigue/excite him? Sex is a big part of this arrangement, but it is not the only part. Can you imagine having dinner with him? Travelling with him? Do your personalities jive? A mistress relationship is built over time, but there must be a strong foundation if it is going to be successful and last over the longer term.

Be prepared to meet a few frogs. It's sort of a mutual interviewing process. So pick a secluded, quiet bar or café to suggest meeting. Meet for a glass of wine or coffee rather than a meal. You will get a sense of whether or not it would work pretty quickly. Wear something lovely, but not overtly sexy. Be gracious even if you, or he, is not the chosen one.
Dear Miss Jay,

Can escorting make you fat? I've been working for nearly six months and I have gained nearly 18 pounds. What should I do?

Anything can make you fat if you don't watch what you eat and are lax about exercising. For an escort, though, staying fit is part of the job description. Take a daily walk or instead of driving or taking the bus, get a bicycle. You will get legs of steel and a trim physique in no time. And it's a lovely way to get around, see the city. Invest in a basket or some other device to carry your baguette, flowers, and bottle of wine home. And get a cute helmet. Take your cue on attire from the Europeans. Forgo the dreadful spandex for something chic and sportif, instead. For shoes, flats like Keds or Vans, or Converse are the way to go. Wear sunblock and sunglasses and a pretty, broad brimmed hat. Smile. Be happy.

Dear Miss Jay,

I have been doing an increasing number of domina dates. Great fun and a wonderful change of pace from the regular escort experience. My question is whether I should allow my domina clients to ejaculate after I have put them through their paces. They nearly always want to but I am not sure they should. At the same time, I love having them come back again and again and I am worried they will get frustrated and find a more permissive domina.

Oh, predictability is so boring. You must keep them wondering the same thing during the course of the session. Sometimes you do, and sometimes you don't. Anticipation is the best sort of state for the submissive to be in. Denial can be wonderfully thrilling for them, so don't think that they will get frustrated and never be back. It is the exact opposite of an escort encounter. The stricter you are, the better. Punishments should be the norm, rather than rewards. "Putting him through his paces" is a wonderful descriptive for the sort of activities engaged in whether it be bondage, a spanking or whipping, or even making them stand in the corner, naked, with a pair of your panties pressed up against his nose into the wall. It may all seem rather odd to you, but pleasing the client is what your business is about, so you should be creative in your approach, and you will never be accused of being predictable, or gasp, boring.

Dear Miss Jay,

A couple of my escorting clients have fairly major foot or shoe fetishes. I am pretty sure that they would like escort dates devoted to their penchant but I can't imagine what we'd do for an hour. Any suggestions?

Oh, there are hours of fun to be had with shoes. Even before getting them on there is the ritual of putting on a sexy garter belt and stockings, a dress, and then slipping into a lovely pair of sky-high Louboutins while your client sits and watches. If you arrange things properly, he will have had the delightful experience of purchasing them for you, and will leave them as a gift. And you will wear them each and every time you see him, until he arrives with another pair. Oh, and shoes of such fine quality need careful attention such as cleaning and polishing and this of course is the duty of your shoe-fetish gentleman. There is of course, the lovely click clack as you prance about, removing said dress to reveal lingerie, long legs, and shoes, glorious shoes. Shoes can take on many roles, and go many places, so use your imagination and take your cues from your caller. At the end of the session, there is the removal of the shoes, the careful wipe down, and lovingly placing them in the box wrapped with tissue, in a closet, or on a shoe rack with other in assorted arrays of colours and heel heights. You will never look at shoes the same way again, I assure you.