The escort’s guide to role play

Many humans have particular desires in and out of the bedroom. These can range from mild experimentation all the way through to psycho-sexual scripts of daunting complexity. Somewhere between being tickled with a feather and building a full scale dungeon, most escorts are asked to assume a role and indulge in a little kink.

by Hannah Jay

Books have been written on the more esoteric reaches of male sexual desire and they are all available at Amazon. But none that I have read answer a much more basic question: how do you, as an escort, get your head into the game? And, more importantly, should you?

The role of the escort

For many girls, escorting itself involves a good deal of role playing. For example, virtually every escort has her escort name and a carefully crafted persona in her advertising and on her website. She steps into this persona when she is working and steps back out into “real life” when she is not.

In her escort persona, a girl will often dress differently, change her makeup, try to be a bit bolder and generally create an alter ego.

Many girls actually have a bit of a ritual. Something as simple as putting on a bra with more than a little oomph and a pair of really sheer stockings matched to a firm garterbelt can be transformative. Or, two steps back, a bubble bath an hour before a date can set a girl up for her encounter.

Making the transition from her real persona to her escort persona is a basic bit of distancing psychology which lets girls do their business without inflicting any damage to their core personalities. The escort’s motto, “It’s business” can transform a potentially fraught situation into a pleasant, if a little distant, interlude.

Part of donning an escort persona is, for many girls, also a way of keeping whatever is going on in their non-escort lives from impinging on their dates. The gentlemen callers do not want to hear about her vet bills or the cost of repairing the air conditioning on her car. They are giving themselves a treat, a little break from their day to day lives, and part of what they are paying for is the fantasy of a willing girl who is, somehow, floating above the day to day.

All of which is a role. An act as it were and one which an escort either masters or flails at. The old joke goes, “Sincerity is vital; if you can fake that you have it made.” Which is a cynical way of recognizing that the most basic psychology of the escort encounter is to create a bubble of trust and acceptance for the men who, you hope, will pay you well for their pleasure.

Expanding the role

Once a girl has her escort persona firmly in place and understands what her clients are basically paying for, there is lots of room to expand her repertoire and range. Nothing kinky, just understanding that there are a lot of different forms escorting itself can take.

Key to expanding the escort role is an appraisal of who you are and what sort of escort you aspire to be. This appraisal can occur at the beginning of your career or after months or years in the business. Because your escort persona is constructed it is also very, very fluid.

Simple questions like, “What sort of dates do I like best?” are a good starting point. Or aspirational questions like, “Where do I want my escorting business to be in six months?” can get the ball rolling. And don’t be afraid to go negative. Asking, “Which dates have I disliked?” can make your own preferences very clear.

At the same time, thinking about how you like to present your escort persona can lead to a lot of useful fine tuning. Do you like to primp and fuss before a date and make sure your in-call environment is “just so”, or do you work on the “what you see is what you get” principle? Both can work. Would you prefer your clients to think of you as a bit aloof or are you all about, “kick back and relax with me”? Who you actually are is a huge determinant of what sort of escort experience you are going to be happiest providing.

However, once you have done your assessment you will have a pretty good idea of where you are aiming. So now you can set about making yourself more comfortable. If your best dates are with out-of- town business men looking for an evening’s high end entertainment, then you can craft your advertising, website, wardrobe and in-call to attract those clients and, to some degree, put off the men who don’t fit your profile. Or you may have preferred the simplicity of “provider” dates where everything is on the table and the nuances of atmosphere and lingerie are simply a distraction from the main event. Every escort has her preferences but the key thing is that those preferences form the basis for her own, deliberate, choices.

Going deeper into your own escort role gives you the opportunity to really explore your possibilities. At one level, being in control of your escorting persona will make you dates easier and more rewarding. At another, having a rock solid core role lets you experiment with that role. If you are doing executive out- calls, you can think about what it would take to set up an executive in-call situation and how that could expand your business. If you are happy in the “girlfriend experience” space, you can begin to think about how that experience can be enhanced to add value for your clients and increase your repeat business.

Your escort persona is the most basic role playing you do and you do it every date. So understanding that, what about all those other things men want you to do and will pay for?

A safe place

When a client comes to see you or you go to see him, there are certain, largely unspoken, rules to the game. He is paying for your time. There may be consenting adult activity. Those are the most basic; but there are others. The most basic of these is that what occurs during the encounter is strictly between the escort and her client. (Which is one of the reasons that the whole hobbyist/review thing annoys me.) Equally basic is that while the escort may decline to participate in certain activities she does not judge her client for asking.

Privacy, discretion and non-judgement are as much a part of the escort encounter as the activities between consenting adults and the envelope on the hall table. Most girls understand this from the go but it is worth unpacking a little.

For most men, vulnerability of any sort can be very difficult. Day to day they are expected to conform to various social, and implicitly, sexual norms. Even minor deviations from those norms can cause huge embarrassment, shame and humiliation. Whether at work or at home, many men are deeply constrained by what they believe are the expectations their wives, co-workers and friends put on them.

Within that context, a very limited repertoire of sexual and psycho sexual activity is acceptable. While the menu may be more extensive in some marriages or relationships than in others, asking for things not actually on the menu is seen as a very high risk move. And it actually is for a few reasons. First, with a wife or girlfriend, the “ask” leaves a man very vulnerable for the duration of the relationship. Women can have long memories and can and do tease their husbands and boyfriends with whatever “perverted” thing they disclose. Worse, the mere “ask” can become fodder in divorce litigation or grist for the gossip mill at the end of a relationship. Merely to ask is to risk exposure. Which is often why a man decides to hire an escort.

Not so much because the escort is willing to engage in out of the mainstream activity – she may not be; rather because he can ask without consequence.

The other element of male vulnerability is their own sense of guilt and shame over what, objectively, maybe a completely trivial desire. What an escort needs to know is that what she might see as entirely matter-of –fact, may actually have been haunting her client for thirty years and by expressing his desire he is overcoming all those years of repression.

By hiring an escort a man may very well see himself as buying the right to ask while also ensuring that his identity and privacy are respected. And that may be the only situation in which he feels he can express his forbidden desire. Which sounds awfully melodramatic but in many ways reflects the reality that a nice guy who is a husband, father, baseball coach, pillar of his church and successful businessman is bringing to his escort encounter.

A big responsibility, non?

Well it could be if escorts were trained, registered, psychologists – but generally they are not and their responsibility is limited. The implicit promise of privacy, confidentiality and non-judgement creates the circumstances where a client can, if he wants, express his desires. If an escort can provide a safe psychological space she has kept her end of the bargain.

OK, he’s asked… Now what?

When a client has a specific request, think about it. And tell him you are thinking about it. Even if it is something which you are pretty sure you are not going to be doing, remember that sometimes your client has taken a big risk mentioning his desire at all.

For role play to work at all, the escort needs to be comfortable with the activity and able to actually achieve the fantasy her client is looking for. While you may be perfectly willing to entertain your client’s desire to dress up as a naughty elf, you are not terribly likely to have an elf costume, in his size, handy.

Even if your client’s fantasy is well beyond your hard limits – and only you know what those are – your client may very well be deeply satisfied simply having told someone about his fantasy. (Remember that phone sex is still a money maker for just that reason.)

However, assuming for the moment that your client’s peccadillo is inside your limits and you have some or all of the props required, you still have to make some decisions.

The first is a purely commercial question: your client has hired you for a standard date and this new request is not standard. What to do? Some girls have a flat upcharge for extras, others will suggest that this little extra will take a bit more time and be a bit more expensive, still others suggest that a great tip is expected. All good strategies but, in many cases, shortsighted.

Being a bit cannier can enhance your revenue for literally years. Remember that your client has told you something about himself at some risk and with, possibly, a good deal of courage. Men with kinks don’t stop having those kinks the first time they come close to having them fulfilled. In fact, if they find someone who can scratch their itch, coming back again and again is very attractive because they will not have to go through the trauma of having to work themselves up to revealing their secret to another escort. Done right, a girl can convert a client into a high paying regular with a few smart moves.

First, get the details. Men with fetishes, kinks and outré desires often have very elaborate fantasies surrounding their obsession. Fantasies which they often have had no one to speak to about ever. You become a listener.

Second, reflect back those details. (What colour is the elf costume? Are pointy ears involved?) Next: Would it be more fun if both of you were dressed as elves? As you listen and reflect think carefully about whether you want to participate and, assuming you do, do you have the necessary props or can you obtain them?

Third, depending on the requirements of your role, it may be a good idea to suggest that you have some fun talking about what you are going to be doing when you have all the items needed to really make this real. For all but the simplest fantasy and role play a bit of preparation is a very good thing.

When it is time for consenting adult activity, even when you have booked the next date for the real deal, you will have all the information you need to talk him through his next encounter while he is enjoying this one. Just a few words here and there will likely push him over the edge and leave him panting for more.

Professional grade

If you are going to play a role for your client you must set up the next date to perfection— take the time to find the right outfit, props and equipment. And, when you are arranging the date, be very clear with your client that you will need some money to buy them. (PayPal is your friend here.)

The last thing in the world you want to waste his money on is the Made in China crap which is the stock in trade of the sex shop business. Getting a real nurse’s uniform or, better still, a vintage nurse’s uniform at a vintage clothing shop will take a bit of hunting around but will be more than worth it come the day of the “naughty nurse” play – and likely cheaper than the see through nylon junk the sex shop sells.

Equestrian supply shops are surprisingly common – though usually located where there are actual horses – and will happily sell you riding crops and dressage whips (look them up, they are beautiful) at a fraction of the price pseudo ones go for at the “fetish” shop. Alternatively, a fine bit of rattan cane can be had in any Chinatown (and most garden shops) for a dollar or two and works exceedingly well.

If you have a little more time and resources, Amazon and E-Bay are huge sources for sex toys, bondage gear and deeply authentic cheerleaders’ outfits.

If your burly client wants to experience the pleasures of cross-dressing, a trip to the larger size section of your local thrift store will produce wisps of lace which might actually fit.

Remember the details of your client’s kink. If he mentioned pink ankle socks or an angora sweater make a serious effort to find those exact things.

At the same time, a professional grade fantasy experience takes into account that realizing a fantasy brings a degree of physical reality to the proceedings. That means that you have to be safety conscious all the way through. While your sixty-five year old client may very well want to be in full suspension bondage for the afternoon, his wise young mistress will decide to tie him carefully to her bed. She will also know that the important thing about being pegged is not the size of the strap-on but rather its enthusiastic use.

The one thing which an escort has to be extremely wary of is her own restraint. There are, unfortunately, too many “bad dates” without willingly increasing your own vulnerability by agreeing to serious bondage under uncontrolled conditions. While you might be game, it is wisest to submit in the safe conditions of a professional domina’s studio with her present…more fun too because you can relax.

The real role

Giving a client a safe place to talk about and, later, explore his desires can build a fantastic client relationship, add to an escort’s income and, in some cases, be quite a lot of fun.

The thing a role playing escort is really selling, though, is permission and enthusiasm. Role play does not work well if an escort is less than committed to her role as an afternoon elf. She will have a not so great time and her client’s itch will remain unscratched. So it is much better to say, “No” than to reluctantly “give it a try”.

Which means that once you have agreed, got the kinky details, and found just the right costume, lingerie and props, you need to bring your best game to the event. If your client’s request is something you have never done before, the internet is your friend. There is nothing the internet has not done before and there are incredibly detailed blogs and forums on every element of the vast universe of male desire. An hour’s research and you’ll know what to expect and have some idea of what to do.

Remember that playing a role means that your client will also be playing his. You may see it as all in a day’s work, he will be seeing himself as taking a huge risk. The very idea that he has found someone he can reveal his mildly exotic tastes to is likely as exciting as the activity itself.

Just by being open, and escort can please her client and gain a loyal regular. And admit it, you’ve always fancied that cute little elf costume.