Travel: The longest escort session

Clients will sometimes ask an escort to accompany them on a trip.  Whether short or extended, travel raises a whole set of new opportunities and challenges.  Navigating travel dates is not always straightforward, but they can be lucrative and fun.

by Hannah Jay

Business First

While your client may think taking you to wine country or to New York will be fun for you, the fact is that a weekend away from your business will cost you money.  Your client actually knows this. So charge accordingly.

A good rule is that your fee for a weekend should be set at what you would normally make over a weekend with, perhaps, a discount if you’re going somewhere you want to go. But, and this is critical, your fee should also reflect what your client expects of you.

Business or Pleasure

Your client is looking for a companion.  Aside from the obvious, you need to know why.  Is he going to a trade show, a wedding, a set of meetings or just to relax? Will you be with him all the time or will you have your days to yourself?

If it’s a business trip are you a secret pleasure or will you be accompanying him to parties and dinners?

Whether it is business or pleasure, you’ll need your client to buy you a travel wardrobe suitable to the requirements. If you are on your own during the day, you’ll need spending money.

So, when he asks what your escort fee will be, be up front about the “extras” you’ll expect.  On a business trip where he’s busy during the day but wants you to accompany him to business functions, hair, grooming and a trip to the spa can all also be added to the package.

On the other hand, a naughty weekend away with just the two of you can be delightfully simple.  You might ask for an outfit for Saturday night but that also might make you look plain greedy.  Never a good look.


Normally your client will book flights, hotels and other reservations. But your client knows you by your escort name.  This is not a problem for dinner, it is a huge problem for planes.

So, two alternatives if you are flying.  First, you book your own ticket and have your client reimburse you (which assumes you have a credit card.) Or you let down your guard and give him your real name.

If you are going away for a weekend or a week, the reality is that you are taking the escort-client relationship to a different level. A car trip to a close by resort requires little disclosure, a week in Paris is going to involve flights and passports.

Realistically, you really should not be thinking of traveling far enough to be flying with a client who you don’t trust with your real name.

What to Pack

As a traveling escort you are being paid to look great.  Schlepping around in comfy clothes maybe fine for a country weekend but a smart day dress will beat jeans every time.

You are also going along for your client’s pleasure.  Which means taking a few escort specific items.  While pretty bra and panty sets are perfect for day, make sure you have evening wear worthy lingerie and lovely bedtime attire. At home you might sleep in a t-shirt and panties; for a trip you should aim to surprise your client every night.  Here the vintage and thrifts are your go-to for everything from sheer little baby dolls to long silk night gowns. Even though they will end up coming off, pretty, seductive, nightwear will keep your client amused.

Bring along a favourite toy for a potential show.  Bring several small candles to set the mood. Pretty scarves are fashion by day; light bondage or blind folds by night.  Of course an escort never travels without condoms and her trusty lube. Some massage oil and a bit of bubble bath can also heighten the pleasure.

The Long Date

Most escort encounters last an hour, with dinner,  perhaps two or three.  A weekend, however, poses challenges you won’t encounter on an average date. The activities of consenting adults – even with Viagra – are not going to keep your client amused for 48 hours.  And a week can be practically forever with someone you barely know.

For the moment, we’ll assume a weekend with no business element.  What are you going to do?

First off, before you go, you are going to do your research on your destination.  What are the fun features? And, as importantly, what do you actually like to do? And what does your client enjoy? Knowledge really is power and an escort who can come up with a great itinerary on the spot is the one asked back again.

Second, figure out who’s in charge.  Are you there to do what he wants or would he be happiest if you set the agenda? Then figure out if he wants a relaxed, kicked back experience or if he is a man of action who wants to pack each day with activities.  Obviously, if he takes you to a ski resort you’ll be skiing, likewise of fishing or golf focused resorts. Those are easy (well, if you ski, fish, and golf).  But a new city or a quaint country town, require a bit of imagination.

If you are arriving Friday, a simple dinner and an early bed time may be a weary travelers’ best move.  But a clever escort will have alternatives beyond bed in case he wants to unwind a bit.  A good jazz club is always fun to find. A cozy bar or a comfortable artisan beer pub can be great as well. Look for what’s available in walking distance and, whatever you do, don’t overindulge. Remember, although you may appear to be on a holiday, you are really working.

For an escort ,there is always the question of how she entices and captivates her client. In public, simple things like his taking your hand, all the way to his sliding his hand up your dress in private can, if handled clumsily, lead to awkwardness. Here, again, it very much depends on the client and how you manage him.

With rare exceptions, it is usually best for the escort to be in control of any erotic element of the date.  For instance, rather than having your client pick the moment to find out if you are wearing stockings, take the initiative and guide his hand to a destination you choose. While you are certainly adventurous and very seductive, in public an escort needs to be every inch the lady.  By taking the erotic lead you’ll actually excite him more than if he has to make all the moves.

Whatever you decide to do your first night, upon arrival insist on going up to your hotel room and getting out of your travel clothes and into something pretty and appropriate. By doing do, you can set the erotic mood for the entire adventure.  A bit of tease is in order to keep him guessing and wanting more. A glimpse, or a suggestion is often more seductive than an overt gesture. Anticipation makes the pleasure all the sweeter. Which is not to say you can’t offer him a quick, (but incomplete) bit of oral attention before you have your bath; but, again, as and escort you should try to control the pace. And it is not at all a bad idea to tell him to wait in the lobby or the bar while you take your sweet time bathing, making up and dressing. That way you get to make an entrance and keep him focused on you. Keep your privacy and your mysteries. For your first night, wear something sexy but understated – you want him to have things to look forward to. While alone, unpack anything you don’t want him to see. Place the candles around the bedroom and, depending on his sense of humour,  a condom on his pillow. A little spritz of your scent in the air makes the space yours. Remember the “do not disturb” sign, so you won’t have to later.

On your return, make sure that while he gets a good look at your pretty lingerie you may wish to tease by undressing fully in the privacy of the bathroom. Plan ahead and have your night wear there. Next night, just when he expects the same routine, you surprise him with a strip tease. An escort must be unpredictable. In a good way, of course!

Aside: if he is using Viagra or a similar medication, if possible try to take control of the dosage and the timing. Many men will take 100mg when all they really need is 25mg. And many men will make a big deal out of carefully cutting their little picker upper.  All they need to do is bite a bit off.  Taken on a full stomach it will take at least 20 or so minutes to work.  Viagra can be an escort’s best friend but it’s best in small doses. You want him to run sprints, not marathons.

One other small note: most hotels now have the proverbial mini-bar/fridge. A clever escort will have found a local market and purchased a bit of smoked salmon or charcuterie, a baguette, a chunk of cheese, and perhaps a few chocolates, for grazing in the afterglow. Make this a holiday he is not going to forget.

Assuming all has gone well and the morning wood has been thoughtfully attended to, Saturday stretches before you. Have a mission or two for the day. Men, especially, men successful enough to afford to travel with an escort, are insanely goal-oriented. Nothing makes them happier than setting out to wander around with a particular goal in mind. Taking in a movie or seeing the sights, it doesn’t matter, he is happiest doing something. Wear some comfy flats and be ready to walk miles.

As part of your research on the locale, select a couple of potential eating spots, both the near and the far. As well, make sure you tap into the best cafes for a mid-morning coffee spot. While you can certainly have a little fun looking in shops, remember the fact men see shopping as a chore, not a past time.

Bring your own money. Yes, of course you want him to buy you that silk camisole; but having your own funds means he can offer to or not. If his memory of your weekend is of an escort with her hand out, he is not going to want to repeat the experience any time soon. Part of what he is buying is the fantasy of a beautiful, independent woman who he can have the pleasure of spoiling. (But, note, if you are on a business trip and he’s in meetings all day, you should make sure your travel arrangements include shopping money.) Some clients are more generous than others. Some will focus on the activities of consenting adults as the primary focus of the trip, others will enjoy the please and tease of the company of a pretty woman. It will depend.

Whatever the daily agenda, make sure that he knows you will want an hour or so to yourself before you meet him for cocktails and dinner. While some of that time will be spent wrestling with garter straps and unruly mascara, at least some of it needs to be your own down time. Check your email, relax by just being off escort duty for a while.

Saturday night on a weekend get away is the production number—the highlight of the holiday. This may include a fabulous restaurant, a drop-dead gorgeous dress, really good wine. Once again, before you send him to the lobby, you may very well offer your oral attentions but, once again, to tease not to satisfy. You want him to know that you are planning a delightful evening ahead.

When you are choosing your outfit for the Saturday fireworks it is time to go for the full effect. You’re out of town. No one knows you are an escort and you can be anyone and wear anything you want and you think your client will enjoy. Whatever you choose, it should take his breath away when you come out of the elevator. At the same time, leave lots to his imagination. We will draw a discreet veil over the effects of your dress, the day, your earlier attentions, and your divine negligee. Suffice to say that when you have done “consenting” he’ll be so drained and delighted he may not even want his post-consent snack.

Sunday morning is sleep in time. You might book an early appointment in the hotel spa and leave him a pleasing note suggesting brunch. Let him have a bit of time to himself while you have your exertions of the night before massaged and bathed away.

If at all possible, and on Sundays it almost always is, make sure that you have the room until your planned departure because after a leisurely brunch, unless he is terrifically eager to go shoe shopping, before packing it will be time for the afternoon delight only an escort can provide.

By this point, your client will wonder to himself why he has never taken you away before. You, on the other hand, should be considering if you would go away with this particular man again. Up to you.

Some escort travel dates seem to fly by, with others the time hangs heavy. And, ultimately, this is where your professionalism as an escort kicks in: your weekend trip was not a test run for moving in together or marrying. It was designed for pleasure in the moment. His pleasure. And your profit.