Questions for Miss Jay
Author: Hannah Jay
Date: 2014-10-12 04:00:00+00:00

Table of Contents

Introduction

Feelings

Dinner

The Rag Trade

A Mistress

Rates and Value

Agency

Naughty

Video Star

Boyfriend Alert

Threesome

Sugar

Fat

Anticipation

Peep Toe

Ruts

Toys

Cruise

Wardrobe

Anxious

Up Top

Tresses

Foundations

Introduction

I have been writing a book called Avails: Escorting for the Elegant Woman.

As I have written escorts and girls thinking about entering the business have written me asking all sorts of questions. Some are about the business, but a lot are about the sorts of things which escorts – and girls who simply want to be stylish and clever – should know. This is a selection.

The interesting thing about escorting is that it is about the fantasy rather then the mechanics of sex. And even that is to make too much of the “happy ending”. For the higher end girls who I write about, the clients are all about spending time with a feminine, intelligent woman whose attention they command for an hour or three.

What the clients are looking for is, in many ways, what all men are looking for: the chance to be the center of attention. A chance to be listened to. A chance to step away from their day to day lives. Escorts are paid, well paid, to create a world in which their clients feel pampered, relax and, of course, pleasure and be pleasured.

Clients are paying for discretion. The ability to play with their fantasies and fetishes in a safe place. The delights of a woman who is confident in her sexuality and, most importantly, herself.

As I wrote the book and answered the questions I realized that a lot of what I was writing applied to any woman making her way in the world. Creating a lovely environment, taking time with your hair and nails, enjoying fabulous lingerie, shopping for super finds in vintage stores: any young woman can enjoy her femininity and the glorious fact men love glamorous women.

Whether a girl charges for the pleasure of her company is entirely up to her. But before she has anything to sell she needs to embrace the beauty and the elegance which escorts and courtesans have created through the ages.

This book is a little teaser….

Enjoy!

Hannah

Feelings

I have one regular client who I think I may be developing feelings for. When I see his number on my phone my heart skips a beat. I text him if I have not heard from him. What should I do?

Well, that is a rather significant hazard of the business.

From a strictly professional standpoint, you should keep your feelings to yourself. And stop texting, for heaven’s sake. When he wishes to see you, he will call and arrange an appointment. You are the escort; he is the client, remember?

From a personal perspective, my advice depends on a few details you haven’t mentioned. Firstly, what do you WANT? And what do you WANT to do? The fact that you are asking for advice leads me to believe that the situation is tricky or you really haven’t thought it through fully. Ask yourself these questions:

- Is the feeling mutual?

- Is he available? Are you?

- What would be the consequences of acting on your emotions? Personally and professionally.

The best advice is to do nothing. For now. You can always act once you have made a decision; but you can’t undo an impetuous action. Time is also a good sorter-outer. See if you still feel this way in a month.

You may also wish to gauge his reaction to a few offhand questions or subtle remarks that will allow you to determine whether he would be receptive to your advances. This allows you to gain more information without laying all your cards on the table. This saves you from potential embarrassment and the risk of losing him as an escorting client.

Talking

Can you give me a few conversation starters? Most of my bookings are at least an hour and there are a lot of awkward silences.

Ah, the art of conversation. An essential escorting skill; and one that you can learn.

For starters, most people think that conversation is about talking. Actually, it is about listening.  Not every silence is awkward, nor must it be immediately filled with words. A thoughtful pause adds weight to your words, draws the attention to you, and gives a lovely unrushed cadence to the entire exchange. It allows for the natural “one thing leads to another” repartee that makes you such an engaging woman to converse with.

Most people love to talk about themselves, so start there. Of course, you must be careful considering the situation, so keep it general and not an inquisition. Ask him what he loves to do in his spare time and springboard from there. He loves to cook? What type of cuisine? His favourite dish? Dance lightly over the topics to keep him relaxed and entertained, and very likely very flattered that you take a genuine interest in him. A little chat before an intimate encounter is always worthwhile to break the ice.

Dinner

At least twice a month a client wants to take me to dinner. Which is great, but he always chooses the same boring, but expensive restaurant. And the food is really not to my taste. How can I suggest a change?

Either directly, or indirectly. But in either case, the trick is to make the suggestion without seeming ungrateful or presumptuous. Artfully accomplished, he will be delighted with his escort’s splendid idea.

Take note, or simply ask him what he loves about this particular restaurant. Is it the food, a great wine list, the ambience? Perhaps the setting ensures his privacy with his escort, or, conversely, he may be well-known to the owner and staff and loves the personal attention?

Do your research to find other establishments that have the features that so appeal to him. You might, for instance, mention a magazine article about an [new/hip/award-winning] eatery as a topic of conversation and suggest that although this place is great, it might be fun to check out what all the fuss is about.

If he is a man who is eager to please you, the mere suggestion will be all it takes for a change in dining venue. If you already have a favourite restaurant, tell him that you think he would really love it, too, and would so like to go there with him. Bon appetite, you old charmer!

The Rag Trade

One of my best clients is in the fashion business - he wholesales a lot of brands. And, of course, he brings me clothes. Which are awful. I know he does carry some nice things but how do I get him to let me make the choices without insulting him.

By being a bit clever, of course. Escorts do their best work when they use their heads.

Why does he keep choosing outfits that you consider mediocre? Most likely because he just doesn’t know your taste. Well then, send a clear fashion message. Pay attention to what you wear when you see him on your dates. If you covet a divine little black dress, stop showing up in round the clock casual wear. Ask him what he wants his escort to wear and work with that.

Does his business have a website, or a catalogue? Pick out what you would actually like him to give you and then engage him in conversation about his business---mention you were looking at the collection online and absolutely adored this particular LBD. Be enthusiastic in your appraisal of how chic it is, and your belief that it would be perfect on you.

A bit of reverse selling, but a strategy that could mean a welcome addition to your closet.

A Mistress

A very good regular of mine wants me to quit escorting and become his mistress. The problem is that the allowance he's offering is exactly a third of what I am making now. My thought is to say yes but keep a few of my other regulars on the side.

You could do that. But you would be wise to clarify the terms of the arrangement with the gentleman first. That way, all these niggly details are out of the way so you can both get on with enjoying the delights of a mistress relationship.

Clarify if he wants you to be his exclusive mistress and if he expects you to give up your escort business entirely. He may have a clear position on this subject, or he may have not even considered it.

Consider whether you would be happy to give up the freedom you have as an escort. Then get very practical.

Assess what your financial needs really are. Are your expectations realistic or are you trying to emulate the Kardashians? Have a number in mind for the allowance and be prepared to negotiate on your own behalf.

Rather than staking everything on an exact number, I suggest be a bit of coy by indicating that although you would really like to accept his proposition, it would depend on the allowance. See what he says to this. If you are genuinely excited and delighted with the prospect of a mistress arrangement, then it is far better to be a bit flexible rather than making money the deal breaker. To a degree, expenses are variable, and you can always find a way to cut back if you need to. Live within your means for now, because means can always change. Sure you have to pay rent, but there is a difference between choosing a penthouse and a character third-floor walkup. Develop a talent for making wherever you are a fabulous and charming environment. If you have little, go for the modern minimalist look. Haunt thrift stores and auctions for awesome décor at a tiny price tag.

Every mistress has to start somewhere! Would you rather be making lattes at Starbucks all day? Right. There are many advantages to being a mistress beyond money. The main one being FREEDOM. You can make your own decisions without the constraints of a job (unless you want one on the side) or the commitments of a husband. Sure your guy will make demands, and if he really becomes too commanding, you can always give him a good spanking to correct him, or advertise to find a more well-deserving man in dire need of the attentions of an excellent---and now, experienced---mistress.

So, before you rush headlong into anything, keep in mind that a mistress’ allowance is often supplemented by perks, gifts, and general ebullient generosity. A little compromise on your part to begin with may well lead your patron to devotedly house, cloth, and be-jewel you, his adored mistress, for years to come. Not a bad deal.

Rates and Value

What's the difference between a $150 an hour service provider and a $1000 an hour courtesan. And how do you get to that high level status?

Thank you for posing such an intriguing question. Let’s try to peel away the layers to this complexity.

So what is a courtesan, anyway? The term, which originated around 1540, literally meant “a woman of the court”. As a paramour to the royal, noble, and wealthy men of European society, she was more educated and charming than the prostitutes of the day who walked the streets, and thus could charge high fees for her companionship and favours. She had many lovers.

A few courtesans became very rich (and very famous, as well.) However, it was not always a candle-lit world of satin, lace, and opulence, however. Prior to the mid-eighteenth century, courtesans were persecuted (ranging from suffering a tarnished reputation and public humiliation, being accused of witchcraft, to imprisonment, and in some cases, even execution). When courtesans were eventually accepted within the higher levels of society, they became, in effect, career girls, selling their body and mind. Paid handsomely for their companionship not only in private chambers, they also accompanied men of influence to public and social functions. Note that a courtesan differed from a mistress. A courtesan could become a mistress, but then she was no longer a courtesan. Since your question pertains to “service-providers”---escorts/courtesans---we will limit our discussion to this.

The most famous courtesans were in France. They lived in the “demi-monde”. Though not necessarily French themselves, a courtesan in France could successfully operate within the laissez faire French social world. In other countries such as England, courtesans caused scandal; in France, they caused excitement. Many men were enticed, and many women were eager to learn their techniques to practice on their own men, while others wanted to become a courtesans themselves.

A courtesan, when not out cavorting, resided in her own suite of apartments or a grand house. Here, she entertained not only clients, but hosted lavish parties as well. A body guard was often employed to protect her and her vast and valuable possessions. In later life, unless she went to rack-and-ruin by gambling or frivolously spending her entire fortune, these aging but worldly, intelligent, engaging women could still captivate a large clientele. Some even amused themselves by putting ink to paper, penning their memoirs. [Still great reads today are, “Harriette Wilson’s Memoirs: The Greatest Courtesan of Her Age” and “The Memoirs of Cora Pearl: The Erotic Reminiscences of a Flamboyant 19th Century Courtesan.” If the internet is more your mode, check out this wonderful blog: http://scandalouswoman.blogspot.ca ] Courtesans were creatures of fascination in their day (and henceforth evermore), inspiring the imagination of artists, writers, playwrights, musicians, computer game creators et al.

Whew! Sort of changes your perspective on your own escort enterprise, doesn’t it? In keeping with these illustrious French courtesans, we will stay in a French frame of mind (if you don’t know how to speak French, you’ll learn a few phrases along the way). Now lets get on and explore what differentiates the low end from the high end in the escort trade.

First, the obvious: BEAUTY. Not cute or pretty, b e a u t i f u l. The genetic Gods endowed this lucky girl with great bones. (You know, the type that can wash her skin with a bar of Ivory soap and it’s flawless). Mind you, a great face only takes one so far. Taking care of your looks, not taking them for granted, is critical for her, and for you . Shiny healthy hair means not abusing it with heat and chemical processes; age-defying skin needs daily sunblock; and even a predisposition to slenderness cannot withstand the all Twinkie diet. You may not be model perfect, but you can go a long way to enhancing what nature gave you.

Secondly, ATTITUDE. A scowl isn’t flattering on anyone. The kind of woman that draws others to her has a certain “joie de vivre” (a keen or buoyant enjoyment of life). Kindness, compassion, and integrity are also qualities that make her so appealing. Not a Narcissus gazing endless in the pool, but a being interested in others and the world around her. This girl considers her champagne flute half-full rather than half-empty. To improve your own attitude it isn’t necessary to don rose-coloured glasses, simply count your blessings every day.

This positive attitude creates CONFIDENCE. The high level escort/courtesan believes in herself, her abilities, her place in the cosmos. You can tell without even knowing her. She walks with a purposeful stride telling the world she is indeed going places. Her voice is strong, not shrill. She realizes she need not raise her voice to be heard. She is polished and sophisticated and knows how to handle herself. Yes, the French express it best again, a certain “savoir faire” (capacity for appropriate action especially a sureness in social behavior; French; literally, knowing how to do). If you want to cultivate this start by learning and using impeccable manners. Graciousness is a rare commodity in this fast-paced world, so be the calm in the storm.

The fourth attribute is INTELLIGENCE. Beauty is fleeting; intelligence lasts. This doesn’t mean you need a university degree if you want to move to the top of the escort ranks. It does mean focusing on your mind, not merely your makeup. Read books, magazines, brush up on the news, gain some expertise in something that really, really interests you (gardening, woodworking, cooking…whatever.) Then get good at it. Take classes if you can. This is also a stellar way to meet and mingle with interesting people with whom you share something in common. Don’t be afraid if it seems quirky or geeky. If you are passionate about it, then loving it is part of who you are, how you think, and what makes you special.

The final part of the puzzle that elevates the select escorts to a league of their own, is a bit of a mystery in itself. This is known as “je ne sais quoi” (something that cannot adequately be described or expressed; French; literally, I know not what). Even though it may be impossible to define, it is instantly recognizable. For instance, those who have met Angelina Jolie in person have described her as “mesmerizing”. One woman who spoke to her said she literally “glowed”. Star material indeed. Difficult to cultivate, but the above mentioned qualities (see 1-4) contribute to unwittingly acquiring it. In a strange way, it is about radiating your own light. Do so with insouciance. Don’t take yourself, or life, too seriously.

Voila! (French; there it is).

Agency

I am a part-time, independent escort doing quite well. Would it make sense to register with an agency to increase my business?

I would say that if you are doing well on your own, there is no need to join an agency. Indeed there are many good reasons to do so if you are just starting out as an escort, but usually not you have an established business running. Right now you keep all your money, whereas with an agency you are working for someone else and will receive a fraction of the fee for each appointment. In addition, depending on the number of girls the agency represents, your appointments may be significantly fewer than your current rate.  All in all, you have far less control in an agency scenario. A good thing if you just don’t have an entrepreneurial bent; but a disadvantage if you are responsible, good at making decisions and implementing them, and general, like to call the shots.

If you want more business, you would be better advised to look at enhancing your marketing for your existing escort service. You might consider new advertising avenues to increase your number of clients, or create some enticing package rates to encourage regulars, or to establish more expensive offerings such as week-end or out-of-town encounters. Be creative. Think big.

Naughty

One of my regular clients likes to tell me his fantasies. Most of them involve his being tied up or punished in some way. It is pretty obvious that he would like me to do some of the things he is fantasizing about but I really have no idea where to begin. Can you show me the ropes?

Well, no; but he can. I would say, however, that before undertaking any “acting out”, you are very clear with the client about what you are comfortable with and where you draw the line.

Begin with something simple like tying his hands behind his back (zip ties are easy and secure), have him lean over the bed, and give him some lashes with your bamboo cane or hairbrush.

Be kind and give him an introductory half a dozen or so strokes with your hand, then switch to your implement of choice and work up the intensity, pausing between strokes to let him recover and to judge his reaction and level of tolerance to various levels.

If this is pleasing to him, you can expand the role by adding dialogue, serious lingerie as attire, or perhaps having him “confess” and be spanked/whipped as punishment. After the enterprise, he is to thank you. You can then give him the attentions he has earned. Done well, this client is going to keep coming back for more because he has trusted you with fantasies he likely is afraid to share with a wife or girlfriend.

Video Star

I’ve been asked to be a “movie star” by a generous and rather nice client---nothing too doubtful, he’d like to use his iPhone camera to record me undressing and, maybe, going down on him. I am uncomfortable with this but he is offering quite a lot of money.

Okay, so what part of this are you uncomfortable with? Being on tape in a compromising position? It’s worked wonders for Ms. Kardashian, but if you are afraid that it might come back to haunt you, make sure that either your face is not filmed full on, and that the lighting is low. With a wig, stage makeup, and a sexy gown, the “starlet” is not recognizably you. The offer of a lot of money is not one to turn down lightly. You might even have fun doing it, and add another, very lucrative element to your escorting business.

Of Course Stockings

I am an escort working in a big city. I read in one of your articles that you hate pantyhose and think stockings are way better. I looked up the Kate Moss ad you mentioned and WOW! they are soooosexy. I think my clients would love them! I  was wondering if you can give me some info and tips on what I need to know about buying and wearing stockings.

Oh, I am so glad to have made a convert! I assure you that once you start wearing stockings, you will want to wear them even when you aren’t working. They are as delightful to the wearer as to the lucky man who gets a glimpse.

Pantyhose, on the other hand, are horribly unflattering and are neither comfortable nor fun to wear. Some women simply give up and opt to go bare-legged instead. But unless you are going to the beach, you need a more polished look with your dresses and skirts. And lets face it, few of us have perfect legs. Stockings provide a smooth, transparent effect while adding a soft shimmer to subtly enhance what you already have. And isn’t “illusion” what great lingerie is really all about anyway?

Some excellent fashion brands, like Donna Karan, offer stockings so check out the hosiery department carefully. In general, stockings can often be rather hard to find, with rather few to choose from when you do. There remains a tiny contingent of manufacturers which still use the few remaining original hosiery machines left in the world.

Thigh-high stay-ups are an excellent option and, if you have never worn stockings before, these are a good introduction. They are worn without a garter and stay put by some sort of gripping system at the top. Check out the many clever modern options here: http://lingerie.about.com/od/HoseCamiSlips/tp/10-Thigh-Highs-That-Will-Stay-Up.htm

Stockings from the 1940s and 50s are what you are really after. Vintage stockings are currently very collectable (especially if in box) and those from the venerable couture houses of old, such as Christian Dior and Schiaparelli, generate fierce bidding and command ever-escalating prices. It is a hosiery style that is unparalleled in quality and beauty.

To gain an education in this world, type in “vintage stockings” at ebay.com and prepare to be fascinated. From expensive, original lingerie posters that you will covet for your boudoir ($1,000 - $2,500), to the cool (Twiggy stockings in a 60s psychedelic package, $160), to the rare (textured hose with the faces and signatures of The Beatles along the welt), to everything in between and beyond. Once you purchase a pair ($20 including shipping for basic seamless nylons), you will want to collect (many, many) more. Unlike the generic $5 pantyhose you pick up at the supermarket, vintage hosiery preserved from a bygone era has a story, a past. It speaks of something quite elegant, sensual, and erotic. Stunning retro stockings come in luxurious options such as silk, seamed, sheer, and shades.

DENIER (how many threads of nylon) differentiates the level of opaqueness in the stocking trade: the higher the denier, the softer and silkier the feel. They range from ultra-sheer –7, 10, and 15 denier, up to a 40 denier which is opaque.  Stockings knitted with a higher denier are less sheer but more durable.

Since stockings were designed to be worn with a garter belt, a reinforced panel at the top of the stocking was knitted separately in a heavier denier yarn and machine-sewn and double folded to give strength for fastening the supports. This is called the WELT. Some have heel and toe reinforcements to prevent runs, others are sandalfoot (all sheer) for wear with open-toed pumps. CUBAN HEEL stockings are the holy grail of stocking aficionados. Also known as FULLY-FASHIONED hose, this refers to a steamed stocking with a line in the back to the thigh up to the KEY HOLE and above to the top of the stocking. A darker colour covers the toes and the bottom of the foot is squared off in the back of the heel. Fully-fashioned stockings were the most popular style until the 1960s. They are, bar none, the sexiest hosiery. Ever.

One of the objections modern women have to stockings is that they require time and effort, and are fussier than simply pulling on sausage casings (Oh, did I say that? I meant pantyhose, of course!) Yes, this is true, stockings do have delightful and intimate intricacies and accoutrements. The wearer must handle the nylon or silk with care. Putting on one’s stockings is art, and a sensual experience because of its very unrushed nature. Choosing a beautiful garter belt, waist-cincher, garter skirt, girdle, or corset to anchor one’s stockings, adds another dimension to a woman’s lingerie drawer. How, I ask, can anyone be too busy to indulge themselves in such a wonderful way? Perhaps women have become altogether too busy and too darn practical. Not the escort, though. Focusing on the erotic is her forte, and a large measure of her appeal.

Calling Card

I was sitting in my favourite upscale bar, (name of hotel withheld) reading a fashion magazine and waiting to meet a client. A good-looking guy who I had seen a few times, and who is a regular there, (and who had figured out that I’m an escort), came over and asked if he could join me. We chatted for a while and then he said he always wanted to approach me for an escort date, but never had the nerve. Well, I couldn’t accept because I already was booked for the evening, but I told him I’d love to another time. I hope I didn’t lose his business. What is the best way to handle these booking situations?

Oh, you charming and alluring creature! You are the best advertising for your business and you know it. How clever of you to conduct your business ever so discretely yet in public. A regular haunt for a pretty girl on a bar stool is a way to say what you are about to those that are paying attention. And obviously, this man was. You cannot always be available, but that doesn’t mean you have to lose business.

The best solution is to have an elegant card that you can give the gentleman in order to arrange a mutually convenient appointment time. These days, the cost of production is reasonable, and you don’t need to have hundreds made either. If you are creative, you could even design and print them yourself using your own computer. Or, if you don’t have a printer, you can simply send the file to a nearby outlet. Stick to a basic format, and remember that black and white is cheaper and always looks elegant. You need to have your name and number and an email address if that is also a way you book clients. Having an attractive card makes you seem not only professional, but also successful and in high demand. Which you certainly will be if you keep handing out your card!

Twosome

I work as a high end escort in a large American city. Recently, a long-term regular client of mine – a great guy in his early 40’s – asked me if I would be willing to entertain both he and a friend of his at the same time. He is very generous and has said he would make this threesome very worth my while. I don’t know if I should accept his offer because I don’t have any experience with this at all. I must say that the thought of it makes me a bit nervous, but I’m kind of excited with the idea, too.

Think of this new experience as adding to your repertoire as an escort. This is always valuable and usually very lucrative---adding 50% to your normal rate times two is not out of the question. So, if you are comfortable with this proposition(nervous is normal), chat to the client beforehand about what he has in mind and his expectations. You can tailor the session to make it a fun and sensual encounter for everyone.

Your gentlemen, if they truly are, might arrive with a bouquet of flowers, a bottle of bubbly, and a silk garter belt and stockings just to make you feel like the special centre of attention. If you can’t be sure they can come up with such a delightful plan themselves, suggest it. As you are now a rarified woman who wears stockings (see above), this is a thrilling treat for the men in your company.

Taking the time to sit down together with a glass of champagne or prosecco is a wonderful way to meet, break the ice, and make everyone more comfortable. One question which will arise is whether they would like to enjoy your favours one at a time privately or together. While ultimately this is the escort’s own choice, it is a good idea to ensure that all the consenting adults are on the same page. It is also a good idea, before the bedroom hoves into view, to lay out any ground rules or no go areas.

Just as you would with a single gentleman, make sure that you take the erotic lead. Simply by shifting the conversation in an erotic direction you signal the festivities are beginning. Undressing, just a little, down to your slip for example, will ensure they follow where you lead.

Once you move on to the bedroom, the focus can either be on one gentleman and then the next or shift from one participant to another while all are engaged. Things tend to progress fluidly, so you don’t have to have the whole time scripted. Toys are an option that can be entertaining, too. My best advice is just to relax and have fun. If you are, you can be assured that your two callers are, too.

One critical thing about a threesome is that it is very, very, unwise to have one if you don’t know and trust one of the gentlemen from earlier, singular, encounters. Just don’t do it. It is dangerous and, unfortunately, undercover police prefer to travel in pairs.

Out

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

Boyfriend Alert

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.

Threesome

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.

Sugar

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 an ad, but not an escort ad, 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 ads 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.

Fat

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.

Anticipation

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.

Peep Toe

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.

Ruts

I’ve been escorting for about six months on a sort of part time basis. I am very selective and only do three or four dates a week. I love the cash and I like most of my clients. Here’s the thing. I seem to be stuck in a bit of a rut as far as dates go. I do pretty much the same thing, the same way, every time. I’m bored and I am afraid it is beginning to show. Any suggestions?

Well, a rut can befall even the best of us. The first step in getting out of one, is recognizing you’re in one. And you have. So let’s look at what you can do to add some sparkle to your eyes.

Actually, start with your lips. March yourself to the cosmetics counter and buy a fabulous tube of red lipstick. There is a shade that suits every complexion and it is an instant pick-me-up. The sales clerk can help if you aren’t sure what to choose, and will allow you to try it on from a (cleaned) tester. On the way out of the department, spritz on some expensive fragrance. Feeling better already? I knew you would.

Then off to the thrift store for a swoon-worthy vintage dress. Doesn’t need to look like what you typically wear; in fact, it’s better if it doesn’t. Take your time, have some fun, try on lots and only buy if you are madly, truly in love with the garment. If your budget allows, complete the look with shoes, pretty retro lingerie, and accessories like great earrings or an eye-catching cocktail ring (a perfect choice for an escort, actually, because it will really accentuate your every movement). Now you will be looking forward to your next appointment. Tada.

But before you model the new you, consider a new routine. Shake up your usual date scenario by adding something special or unexpected. It doesn’t have to be champagne and caviar (although it could be!), it might be as simple as a bubble bath for two, or giving or asking for a spanking. If you are usually submissive, explore a more dominant side of you, and vise versa. Use your imagination to come up with something that interests you because your new-found enthusiasm will surely excite him.

Toys

A rather nice, and very generous, regular client of mine has asked if I would be willing to do a “toy show”. I’m game(I think), but I don’t have a clue what is involved. How long should it last? One toy? Many toys? And, I’m wondering why he asked for this. I mean, what’s in it for my client?

Well, I surely can’t speak for your client, but you should certainly ask what he wants to get out of it so you can be sure to tailor the experience to meet his expectations. At a guess, a bit of intrigue and exhilaration is probably at play. Unless you have a tickle trunk of toys, I would suggest that the gentleman called bring (and pay for) the booty. Alternatively, he could reimburse you and you could do the shopping. Look for vibrators, dildos, cock rings, nipple clips, and the one you will want to keep for yourself: http://www.amazon.com/Njoy-Pure-Wand/dp/B000QUYT6A/ref=cm_cr_pr_product_top?ie=UTF8

The length of the show depends entirely on the depth of your client’s pockets. Pull out your sexiest lingerie, jazz tunes, and light some candles, because he is in for a treat.

Cruise

I’ve been escorting for a couple of years and have a nicely up-market group of regulars. One of my best escorting clients wants to take me on an Alaska Cruise. Separate cabins, all expenses and a very generous fee. The problem is he really is old enough to be my grandfather. I suppose I could brazen it out but I wondered if you had any more creative solutions.

Does age really matter so much? Ask yourself if you like him as a person? Do you connect on a physical and non-physical level? Can you imagine engaging in conversation with him over dinner?

A cruise might be more of a commitment than you want to take right now. Perhaps you should suggest an overnighter or a week-end away. Work up to the cruise, if it happens at all.

Wardrobe

I escort in a big city on the West Coast. I’d like to move towards the more lucrative end of the market but, I’m afraid, my entire wardrobe is Lululemon yoga pants, jeans, leggings and T-shirts. The escort clients I am seeing now don’t seem to care but if I want some “Suits”, I know I have to raise my fashion game. Of course I don’t have a lot of money.

The good news is that all that athletic wear has paid off and I am in great shape, 5’8” with a nicely full bust and, if I do say so, really great legs. I’d like to make the most of all this. So, how to I get my wardrobe in shape?

Casual wear seems to have taken hold everywhere, and particularly on the west coast. It is the casual beach wear look run rampant. Lululemon pants were designed for the yoga studio, and in my opinion, that is where they belong and should stay. I can’t say how many times I have seen women wearing them as daywear and wanted to advert my eyes. It is akin to wearing tights without a skirt. Ugggh! And sadly, worn by women who have never been on a yoga mat, or even in a gym. As the former CEO himself was lambasted for saying, they are not for every woman. Amen.

I have written many articles on style and fashion so look them up, but suffice it to say that I am in favour of clean, simple lines, and classic silhouettes. Add bits of fashiony whimsy with colour, accessories, and non-major investment pieces. If animal prints are hot this season, add a scarf in a leopard print to look au current.

To build a workable wardrobe that will span the seasons and the years, start by deciding on a colour palette before you set foot in a store. Then stick to it. Shop sales and wisely, and soon you will have a closet that coordinates effortlessly. If, for instance, you adore yellow, but it makes you look like an escapee from the jaundice ward, then ban it from your key pieces collection and buy a lemon-toned handbag instead. Your clothes are closest to you face, so make sure they are flattering.

Clothing at the retail level is exorbitantly expensive. And unless you have pin money with many, many digits, it severely curtails your expenditure. To get around this, shop consignment and thrift, but be picky…don’t purchase anything that isn’t in nearly new condition. No snags, tears, stains, moth holes. However, I once scored a full-skirted, vintage white and black polka dot dress for $10 because the buttons were missing. An easy fix with minimal cost required. I don my Karl Lagerfield sunglasses (also pre-worn) and feel like a movie star.

For your shapely, hour-glass figure, I would suggest fitted garments like pencil skirts, well-cut dresses, knit two-piece ensembles, and long line trousers. Since you are tall, you can carry off colour, prints, belts, stripes, shoulder details, and many runway looks that many shorter others cannot. You don’t want to look like a beanpole, but nor do you want to de-emphasize your stature. Since tall women often have large sized feet, avoid flats and just go crazy and wear heels. Walk tall; think Amazonian wonder; don’t slouch. And for heaven’s sake, don’t try to be shorter than the men in your life. Let them look up to you. It does wonders for your morale and his humility.

Anxious

As an escort, most of the time I have very little trouble moving from A to B during an escort date. But lately I have found myself reluctant to get down to business. I make conversation last longer than it needs to, I find excuses not to go to the bedroom. I seem to have lost my edge or something. I have been getting the job done but not without a lot of anxiety. Any thoughts on how I can get past this?

As an escort you are expected, and paid for, being on -- even when you really are not so into it. If this is an occasional problem---you stayed up too late watching “Suits” for instance, and you’re just tired, then the remedy is easy: sleep. If however, you feel kind of permanently lackluster about everything, the issue may be more complex.

So look at the obvious first. Are you getting enough rest? Is your diet adequate? Do you exercise daily, ideally in the fresh air? Have you had a check-up lately? Best to rule out a medical condition or an iron deficiency if this is draining your vitality. Do you have an enjoyable and fulfilling personal life? Do you have at least one friend with whom you can chat and laugh with? Is stress a factor in your attitude? Why do you suppose that sex is now a source of anxiety---have you had a shift in feelings, or a bad experience?

If you run through the above list and still can’t put your finger on the problem, I would suggest speaking to a counsellor or therapist. Depression is a serious affliction that is not to be taken lightly. If financially possible, it might also be beneficial to take a break from escorting and focus on other career or personal goals. Go for long walks, read, meditate or take up yoga (wear your Lululemons!!), or whatever relaxes you and recharges your inner battery.

Thanks for writing. Hope this helps.

Up Top

I’m a 24 year old escort in Toronto. I have a pretty good business but, of course, I would like to have a few more dates and charge a bit more money. I think my problem is that I have sort of medium sized breasts. B+ really. I’ve thought about getting them done but that’s expensive and I don’t really feel comfortable with something plastic in me. Any suggestions?

Well, if plastic surgery isn’t an option for you, then you are going to have to resort to the art of illusion.

Here are a few clever tricks to give your figure more definition and make your breasts appear larger and curvier than they really are.

Posture & Exercise

Good posture not only makes you look taller and slimmer, it also can make your breasts look bigger. Stand sideways in front of a mirror and draw an imaginary line down from your earlobe to your shoulder, hips, knee, to mid-ankle. Practice this a couple of times a day if your posture needs correcting. This is immediate, easy, and free.

Exercises to build the upper pectoral muscles (the muscles under the breasts) make them look firmer and rounder. Push-ups (yes, the ones you did in gym class) as beneficial and a great place to begin.

Focus also on slimming and shaping the waist—the breasts will appear larger by comparison. Yoga and pilates are good choices. You want to tone your body not lose weight— which will make your breasts smaller.

Enhancing Lingerie

An ill-fitting bra will thwart your efforts at adding oomph. Make sure you are wearing the correct size (get measured by a professional in the lingerie department or learn how to do it yourself), and make sure they fit properly.

A push-up bra will give your bust a boost. They push the breasts up and closer together to give you more cleavage. Virtually all bra manufacturers carry a few in their lines. The Victoria Secret Boomshell push-up bra promises to add two cup sizes: https://www.victoriassecret.com/bras/bombshell

Padded bras have foam padding in the cups to make small breasts look fuller. No lift or realignment, though. Those padded with gel or air, although a bit more expensive, give a more noticeable effect.

Stuffing your bra with socks or wearing two bras makes you look lumpy, fake, and silly (especially since you are very likely taking it off in company). Leave such juvenile measures for young school girls.

A corset is a wonderful and beautiful addition to an escorts wardrobe and its figure flattering capabilities are unparalleled. Buy the real deal (try Ebay for true vintage).

Other retro lingerie with serious affect are waist cinchers, girdles, and bullet bras. Paired with stockings, you will feel absolutely sexy and seductive. At this point, the focus on the size of your breasts will likely of little import because you look so fabulous in every way.

Wardrobe Choices

A few tricks to fool the eye:

Neckline details such as gathers, pleats, tucks, twists, ruffles and lace all add dimension to the bust-line. Opt for crew, gathered, asymmetrical. Mid-rather than low-cuts also make the breasts look larger.

Colours and patterns can also alter the visual proportions of your body. Light/bright/ colours or pattern on top; darker on the bottom is a good rule. Small horizontal stripes can work wonders, too.

Make-up

Yes, bigger looking breasts can be obtained through the artful application of make-up. Hollywood is on to this trick in a big way. See how Kiera Knightly goes from flat-chested to buxom in the Pirates of the Caribbean movies with a lot of help from the make-up department. Copy the techniques to get the benefits:

http://www.sheknows.com/beauty-and-style/articles/803403/make-your-breasts-look-bigger-enhance-your-cleavage-with-makeup

All right, there are a few tips for you. Enhance what you have, by all means, but also realize that small breasts are beautiful, too.

Tresses

I’ve been reading that escorts with long hair can charge more than escorts who have short hair. I have a rather cute little bob which I want to keep. But, could I wear a wig? Or maybe extensions?

Yes, you could! And it might be fun to try out a new look, and see if indeed long-haired escorts make more money. Let me know you findings, I’m curious, too!

A wig is an easy way to instantly, temporarily change your look without altering or damaging your existing hair. Today, many women wear wigs as fashion statements rather than for hair loss or medical issues. The better ones are well made and aren’t noticeably artificial. They come many styles and shades, in either synthetic fibers or natural, human hair. If cared for properly, wigs can last a very long time.

Those made of human hair can be straightened, curled, and dyed just like your own hair. Although more expensive than synthetic, if you are planning to wear a wig regularly, it is worth the investment for the luxurious look and feel.

Synthetic allows you to have an entire wardrobe of wigs! They are cheap and easy to care for.

Hair pieces can be used for complicated hair styles such as intricate updos that are difficult to achieve with your own hair. They are versatile for special occasions or for when you don’t have the time, or inclination, to attend to your hair. You just pop it in for instant volume, length, chignons, even temporary bangs. These hair pieces are also a great solution for thinning hair.

Wigs and hair pieces can be easily found online in all price points. Department stores and some salons also carry them and will consult with you and allow you to try them on until you find something that suits you.

Hair extensions are a great way to add length or volume to your existing hair. Extensions can be clipped in and blend seamlessly with your own hair. Clip on extensions are quick, easy, and simple. They are temporary and don’t damage your own hair. They come in synthetic or human hair, and many colours, lengths, and weights. They can be purchased online or in retail stores. There are many online video tutorials to teach you how to put them in properly.

Hair extensions can also be done in a salon for a longer-lasting solution (from six weeks to eight months). There are many options here, but you for this option, you are looking at a high cost. This is popular with Hollywood stars, like Lindsay Lohan, Jessica Simpson, and Victoria Beckham who want to change their hairstyle overnight.

Extensions can be braided in, glued in, woven in, attached using a micro ring, as well as other methods exclusive to certain salons. You may also have your stylist put in the clip-on type if you can’t do it yourself. The attached ones must be applied by a technician trained specifically in hair extensions.

After an initial consultation, the hair is special ordered for you once the stylist determines how many strands or bundles of extensions can be applied, as well as the desired length and colour. All these factors affect the cost. The more extensions added, the more time it takes, and the higher the price. A lengthy appointment – of four to six hours -- is required to apply them. After care is crucial if they are to be comfortable and last as long as possible. An hours appointment every six weeks is recommended. And once your hair has grown to the maximum point, you have to go back to get the hair extensions removed. Some types may be reapplied, or you may choose go back to your natural hair.

Hair extensions require a commitment of time, money, and maintenance. They may also damage your own hair.

Think carefully when deciding how best to accomplish the mission of longer hair, and hence higher prices. My bottom line advice, start with the cheapest option, see how it works, and how you like it. Move on, or stay with what works and reap the rewards.

Foundations

I am a fairly successful escort in a middle sized town in the South. I have what you might call an “average” body. Not over weight but a bit less than firm. Can you give me some suggestions as to how to move from average to hot – or at least warm? As well, do foundation garments work? I’ve looked at Spanx but I don’t want to make the investment if they are all show and no go.

Incorporate a daily exercise routine into your life to tone your body. This can be walking, cycling, weight training, Pilates, or whatever you will enjoy, do, and stick to.

As regular readers will already know, I am a big fan of retro lingerie in general, and foundation garments in particular. These include corsets; girdles; control panties, slips, camisoles; bodysuits; waist cinchers; leg-shapers; bras; and garter belts. Also called “shapewear”, foundation garments are lovely AND effective. They provide a smooth, sleek look. Designed to reduce, flatten, shape, and control, these contour garments are categorized according to level of shaping power —light, medium, or firm. Girdles have the most Lycra spandex and are the most effective way to alter your shape.

But Spanx is an inspiring success story (okay, let’s just say it upfront; the founder, Sarah Blakely, is a billionaire). Founded in 2000, in Atlanta, Georgia (I kid you not), the company is the Queen of modern shapewear and hosiery. Spanx specializes in foundation garments and is the darling of the Hollywood red-carpet set.

To quote the “Daily News”,

“She invested just $5,000 to start Spanx at age 29 and has grown the shapewear company into a global megabrand with annual revenues of over $250 million and celebrity fans like Kim Kardashian, Kristin Chenoweth and Lily Allen.”

Forbes pegs her individual net worth at $1.1 billion.

So vintage, or inspired by vintage, add foundation garments to your wardrobe to make your body, and your clothes, look better.