Escort in Training (Emma Book 1)

by James Grey

  My boss wasn’t gorgeous, though. And the thought of running my hands across her soapy breasts, tripping my fingers over each delicate nipple as they go, is untenable. No, I’ll stick with the original cow as my image for giving beatings. Though Petra will always be a handy backup.

  I’m not actually sure how much I’m up for this giving pain thing, despite all the tips we get from Miss Jillings. I know I can be good at it if I get into the zone, but will I always be able to rely on a made-up image of my ex-boss? Looking at naturals like Miss Jillings and Carrie, I’m not sure I’m nasty enough. Sarah suggests as much later that night when we compare notes on our day’s activities. But part of me is determined to keep it on my skills list.

  After all, it turns out I am the only girl who sits in both the dom and sub classes. Gosh, I must be quite the all-rounder! Sarah, Diane, Jane and Carol join me in the latter session. The quiet ones, I guess: makes sense. And Carrie’s there too, salivating at the chance to practice on us, while Miss Jillings and Miss Ridgewell watch.

  It’s a fun session. We’re all told to find the school uniforms in our closets, as this will be our most common attire in an assignment involving punishment. Carrie makes us pull down each other’s skirts before we all bend over the huge oak desk at the front of the classroom.

  The beating is lighter than the one she gave me in the fireplace. She uses a swish with a single, stinging strand. The turn-on is greater than the pain, especially as there’s a gap between sets as she works her way along her row of five miscreant bottoms. As I knew would happen, I soon ache to come, whimpering as my forehead rests on my elbows.

  Carrie won’t let us touch ourselves, on pain of a serious caning. Then the gigantic Geoffrey takes over from her. Poetic enough, I suppose: he’s the one who caught me eavesdropping. It only makes me wetter and shakier. I’m not sure if the others are as affected as I am. When the punishment ends, and we’re all instructed to lie on the floor with our legs open, and Miss Jillings gives us each a little vibrating bullet to play with, I am the first to come.

  Miss Ridgewell runs a session for the entire group, this time on the art of holding back our orgasms. She impresses upon us the need to see a few steps ahead in a situation. How long is our booking? Are there any specific instructions about how and when a client likes to come? Are we confident we can come more than once? Can our client? Has he requested to see us come in a certain way?

  We’ll constantly need to be weighing these things up, she tells us, and evaluating whether we should let ourselves go or not. There are times, we learn, that we’ll need to switch on the opposite of blindfold mode. When we’ll have to try and dull our senses. Diane suggests we could always fake multiple orgasms if necessary, but that makes Miss Ridgewell turn almost purple.

  “Miss Quinn, we are not street whores!” she growls. “Your clients are paying huge money for a real experience. If they want to see good acting, then believe me they can afford box seats at any West End theatre. They want a good time, and maybe some of the warped ones will want to deny you a good time, but I can guarantee you that not one of them wants to see fake orgasms. Ever. It’s one of very few hard and fast rules in this game.

  Simone, and the rest of aspiring escorts in the room, are in complete silence now.

  “You’re worth as much as you are not just for your skills, but because you love your sex. It’s a turn-on, in fact, that sometimes you have to think of other things to hold yourself back. If these men wanted a diet of grudging, fake enjoyment, they would have gotten married, wouldn’t they? Not nice to say, but still true. So…natural orgasms, ladies, and if the timing of that isn’t going to be right, then you’ll need these holding-on skills, understand?”

  Everybody nods, and she plunges into more mental and physical tricks designed to add control to our climaxes.

  “It’s not like you’re going to be doing this all the time,” she concludes with a smile. “Many clients will want things to happen organically. After a few weeks you’ll find you’re dealing with a lot of repeat clients, and you’ll know which ones want you to let yourself go, and which ones want things just-so. The main thing is that you can adapt.”

  After dinner on Wednesday I’m taken into another evening session, with only Alyssia and Latifa. It’s Miss Tottingham. Could this be ‘associated oral sex’? I’ve been wondering about that all week.

  And yes, that’s exactly what it turns out to be. That thing. The one thing I didn’t want to tell Miss Jackson about on that first morning.

  Licking ass. Love getting it, love doing it. I shiver as she runs us through the basics, telling us what a select group we are. I think back to that night in the sauna last week, when Latifa told me to let go. Back then, I couldn’t imagine for a second that I’d end up in any kind of select group with her and her liberated friend Alyssia. My, how far I’ve come!

  Chapter XXXI

  By Thursday afternoon, I am beginning to feel ready. Ready for whatever the world wants to throw at me. I’m exhausted. I’ve come about ten times this week. And still I want more orgasms. I never could have guessed I had so much wicked sex in me. I can no longer deny, on any level, what I’ve become.

  I still have this deep loathing of Petra. It’s all I can do not to slap her when I pass her in the hallway. She’s started scattering clothes all over my old bed, which kind of annoys me when I pay visits to my wardrobe. Even though it was me who chose to leave.

  I miss the big bath in that room, but bathing with her in the room would be like bathing in a pool of awkwardness. Luckily Latifa and Alyssia let me use theirs for a Wednesday night wind-down. They shamelessly sit and watch me, but I’m cool with it. These girls have taught me a lot.

  They’re super-excited about their career prospects, though neither is going to be ready to start right away. They’ve got a few work and study things to wind up first, and Latifa’s considering working in Oman rather than London.

  “Do they…have that sort of thing over there?” I gawp, astonished. “Wouldn’t you get executed or something?”

  She chuckles.

  “Course they do, babe! There are hookers in every corner of this world, you innocent little thing. Trust me, those sheikhs and emirs are all at it, and they pay top dollar. As you can imagine, they’re buying silence as much as anything. And as for Oman, our Sultan is gay, so he can’t be too judgemental about bending the rules, can he?”

  A gay sultan?

  “Well…okay…but I’m sure you’d be safer here, wouldn’t you? Come work with me and Alyssia and Sarah!”

  “Who says I don’t want to go and work back in Perth?” grins Alyssia. “Those mine workers are loaded! But yeah, London would be a good experience, I think. Let’s get our shit together and do it ’Tifa!”

  “Alright, alright…London it is!” says Latifa. “Let’s all try get into the same agency, Sarah too. Deal?”

  “Deal!” I grin, excited to think I’ll have my friends with me as I venture into this mad world. “If you guys need a few weeks to tie things up, I’ll wait. I’ll find out which agency Petra’s in and make sure we avoid that one!”

  Everyone laughs at that, though I’m deadly serious.

  “I hope we’re right in assuming we’re going to graduate,” Alyssia muses. “Otherwise we’re all gonna be lining up to work at Starbucks!”

  God, there’s a thought. I really would be a prize fool to let it come to that.

  “Something tells me we’re going to scrape through just fine,” says Latifa, winking at me. I lie back in the luxuriant warm bubbles, delighted with life.

  Thursday lunch is the juiciest, thickest steak I’ve ever eaten, washed down with freshly-squeezed orange juice. I keep having to remind myself I haven’t paid a single penny to be here, living this life.

  After that, it’s into the final formal session of the week. Miss Jackson, my mentor, leads it. The topic is lesbian skills, and nearly all of us are summoned. It seems like girl-girl play is pretty much a non-negotiable in this game. I�
�m thankful I’ve tried it out at length already this week. The likes of Jane look pretty uncomfortable.

  “Don’t think this is only about doing shows and taking part in group sex, class,” says Miss Jackson. “That’s most of it, and it’s key you know how to genuinely pleasure each other in those situations. But there will also be times when you’ll be booked by straight couples.”

  Ooh, really? I hadn’t considered that.

  “Sometimes it may be that the woman wants to live out a lesbian fantasy, and you will have the massive responsibility of making that fantasy as amazing as she has been dreaming since she was a teenager.

  “Very occasionally you will get booked by a solo female, but most often she will bring her partner along. He may just watch her experiencing a woman, or he may want to join in later. This is one situation where you always need to establish the ground rules with both beforehand. I’ve seen people get carried away, and that’s not a good time to have the conversation about boundaries.”

  She looks around the room. “I believe all of you have at least got as far as licking a pussy this week. I trust you’ve all liked it, ladies. We’re going to perfect the art this afternoon.”

  It’s anatomical drawing time once again. Miss Jackson takes us through a few technicalities, just like Miss Littlefair did with cocks. I feel like I’m a little past this stage, and exchange knowing glances with Sarah when Miss Littlefair mentions tricks that we recognise from our bedroom.

  “Vaginas are rather harder to generalise about that penises are,” she says, “but learn to embrace that. There’s extra satisfaction in getting it right. When you’re working in a small, exclusive agency, you’ll soon get to learn where and how your colleagues like it. It’s a good idea to familiarise yourselves with each other before you go out on any joint assignments. It’s the best kind of teamwork, I always think.

  “When you’re dealing with a female client, all you can do is follow general principles and then follow her feedback, her cues. And for heaven’s sake, don’t get fixated on pussy play. Whether you’re pleasuring a client, or each other for an audience, foreplay is usually a must. People want to see intimacy, feel intimacy. Kissing. Lips on nipples. Hands running up and down her back.

  “You’re all women and you know what a woman likes, she concludes. It’s actually a lot easier than trying to get inside a man’s head!”

  I’m feeling pretty hot by the time she announces it’s time for a practical. I’m up for playing with any of the girls here, and I’m no longer bothered by the audience. A bed has been brought into the room, and it’s scattered with blue satin pillows. It looks pretty comfortable.

  “I know some of you are quite familiar with certain classmates by this stage in the course,” Miss Jackson smiles, “so I’m going to take you out of your comfort zones. Unfamiliar pairings, by my reckoning.”

  What could that mean?

  “The goal, remember, is to provide an intimate, sexy experience to your partner, whilst at the same time losing yourself in the pleasure. Don’t worry about the audience for this exercise. This is about thrilling your lady and yourself.”

  So Lilia and Carol are called up to play together. Then Jane and Latifa, who makes Jane come in spite of herself. I start to think about the remaining permutations. Sarah goes with Simone, and I smile to myself as I watch her squirm under the Dutch girl’s caresses.

  But when Diane gets paired with Alyssia, I begin to worry. I look around the room. Carrie’s not here. I suppose this isn’t really her department. Maybe she doesn’t do pleasuring people. Anyway, so that leaves…God no!!

  I know it’s coming, but I feel utterly rooted to my seat as Miss Honeywell comes in and changes the sheets after Alyssia left an enormous pleasure puddle before her and Diane even finished kissing.

  My temples pound as I watch the housekeeper bustle. I thought I was ready for anything by this stage in the game, but her? I’d love an emergency phone call to come in for me right about now. I find myself glaring at Miss Jackson, because I think she’s done this deliberately. She, and everyone else here, knows exactly how I feel about Petra.

  I breathe in deeply and close my eyes as Miss Honeywell closes the door behind her. Miss Jackson speaks again. For once I am feeling a long, long way from turned on.

  “Miss Carling, I’m not sure if you know it, but Miss Stoycheva is renowned in the trade for her skills in this department. Please come forward and enjoy.”

  I catch the eyes of my friends as I stand up and make my way to the front, feeling a lot like a lamb to the slaughter. I cannot, and will not, allow myself to catch Petra’s eye. We’ll blunder through this, but…intimacy? That’s going to be hard to pull off.

  I can imagine letting her lick my pussy. I can lie back and pretend it’s someone else. But kissing her? That’s another thing entirely. Oh, boy.

  We kneel on the bed, and I feel we’re going to circle each other like coy boxers in a ring. Which of us is going to make the first move? I suppose the real question is, who is the better professional?

  When I think about it like that, I want it to be me. But before I can bring myself to move a muscle, a funny thing happens. Petra presses go. She crawls over to me like a sexy cat, and starts to take control. She pulls my face to hers, drawing my mouth onto her open lips, and…oh my.

  Seriously, I forgot that I quite fancy this girl. So consumed was I with desire not to do this with her, I almost convinced myself I didn’t want to. But now…oh she is good…

  I know Miss Jackson said to forget the audience, but there’s no way I can be anything but aware of their rapture. They must be enthralled by this, like you get drawn into an unexpected twist in a soap opera. Right now, I suppose, the episode would end, and they’d have to wait until Monday to see where it went.

  But it doesn’t end, of course. She deftly unbuttons my blouse whilst sucking in my top lip, as if she’s known all along what that can do to me. I feel my nipples tightening, but with fierce concentration I stop myself from moaning. Because I’m not going to let the class see that she is pleasuring me. That would make her a winner, wouldn’t it?

  I feel like a helpless dummy. I’m too proud to respond, or to try and pleasure her. Maybe it would be a good idea. Maybe it would take my mind off this insane pleasure, especially now she’s chewing my nipple, oh so just-rightly.

  But I can’t. I’m spellbound, caught like a statue, in a no-man’s land between surrendering to delight and trying to remain as cold as her. Maybe that’s why she’s taken the initiative. She knows her technical skills are good, but she might not do so well at conveying intimacy if I do things to her. She’s playing to her strengths, the bitch.

  And yet moving isn’t possible. It’s too good, when she pulls off my blouse, rolls me onto my stomach – thank God my face is off show for a moment – and drags off my jeans and panties in one. I can feel her stripping off her top somewhere above me, and then lying down on my back, in her miniskirt only.

  Her tongue is in my ear, loud and warm and erotic, and then it’s on my neck, and I can’t hold back that tell-tale breathing. She goes lower, biting my ass cheeks and then parting my legs with her hand, rubbing me in that place. Face down like this, I can’t see her, and it’s easier to forget just who it is doing this to me. It almost brings tears to my eyes to try and stop myself groaning.

  But…I...Will...Not...Let…Her.

  And then my respite is over, because she pulls me up onto my knees, facing the class. Oh fuck. I couldn’t ask for a more exposed position as Petra – yes Petra! – lies on her back and wriggles underneath me, her head right beneath my melting, throbbing, begging centre.

  It’s like ice and sparks all in one as I feel her tongue below me. She’s working in an awkward position, with her feet away from me, and I have no idea how she’s getting this right. But getting it right she most definitely is.

  Like this, my chances of staying sober are about as good as an alcoholic’s in a vodka distillery. If I look down, I see her slen
der, petite body snaking away from me with that healthy glow of hers, all the way down to her perfect little toes, and I am reminded of what a sexy animal it is that’s doing this to me. I can even see half her face, and it awakens the uncomfortable, unwanted thought that she is the most beautiful woman in the house.

  I don’t want that thought. It will make me come.

  But if I look up, I will see my classmates. Alyssia. Sarah. Latifa. Everyone! Even Miss Jackson has moved to that side of the room. The thought of catching their eyes…I honestly have no idea what that would do to me. But I don’t like it. I know what they must be thinking. Nothing bad about me, just…wow, being the centre of attention, you know? Like, nobody in this room is thinking about anything other than what’s going to happen next.

  Anyone else, and I’d just let myself explode right now. But pride has me ensnared, no matter how luscious that roaming tongue is. No matter how…oh!...beautiful it feels as it tickles my clit. Fuck, does she have to get it so right? I’m tightening all over. Nipples and hairs stand on end. But I keep my breathing zen. And not a sound passes my lips.

  Is this a matter of professional pride for her? Is making me come the kind of thing she thinks will make her graduate, if she even needs to graduate? I still don’t even get why she’s here, if she’s this good and she’s already working. Yes, this good. Fuck, yeah, right there…Petra.

  I’m on a knife edge. I’ve been holding on for a few minutes. Actually, some of the tricks from that delay-your-orgasm class come back to me, and I clench everything. I know this is not the assignment for those skills. I’m letting my feud get the better of me. I’m being unprofessional. Why not just come? You’ve got a thousand volts in your vagina right now.