Escort in Training (Emma Book 1)

by James Grey

  “I know…and I think I’m getting there,” I tell her, thinking back to my musings in the sauna last night.

  “I don’t doubt that for a moment, darling! Now, let’s take a look at this DP assignment…”

  “DP?” I give her a blank look.

  “Double penetration! Oh dear, you really are an innocent one aren’t you? Well, maybe uneducated more than innocent…because you made me proud with your attitude that day. Some girls get pretty freaked out when two men enter them for the first time, but you seemed to have a wonderful experience. And it was your first time, right?”

  “Er, definitely! I think I’d remember that if it had happened before!”

  I’m totally transfixed by the screen now. Shame has turned to disbelief. That’s me having my anus penetrated, right there. Oh my.

  I’m beginning to feel a little bit wet.

  “Another thing, Emma. You and Sarah…it was a privilege to watch the chemistry building there. An absolute privilege. It took everything for me not to get up and push in on that kiss, but it would have been very wrong to interfere with something so natural.”

  She shakes her head in a slow, dreamy kind of way.

  “I had a hunch you two would go well together, that’s why I paired you. And I understand you’ve been doing some extra practice with her?”

  Am I in trouble? But the corners of her mouth are turned up in a knowing smile. I think she approves of my extra-curricular activities.

  “Oh! News travels fast around here…”

  “It’s my job to know these things, Emma. By the way, if you’re wondering, your rooms are the one place where there are no cameras. They’re private in that respect. Everywhere else is covered. Soon we’ll see your little fingers doing their magic in that toilet cubicle.”

  “God…” I bury my head in my hands, my fingers clawing at the perspiration around my hairline. But then I come back up smiling.

  “That’s better. Laughing at yourself is the first step in your walk away from cringing at yourself. All this may seem bizarre, but remember your office desk in London was on CCTV as well. And I think you’d be having a lot less fun there, wouldn’t you?”

  Well, she’s one hundred percent right on that. Monday morning is PowerPoint presentations. Yep, they’ll be in the nine-thirty meeting right about now. My smile broadens. “Absolutely! Maybe you should stream this film into conference room 14C. That would wake them up!”

  She laughs out loud. I like how the mood is lightening. “It certainly would, Emma. But remember, at this level we are a very discreet game. Girls like you don’t hang out on street corners or put their cards in telephone booths. You’re exclusive and you’re confidential.”

  We move on to the most intense moment of the week: my thrashing of Rupert and Petra. Miss Jackson goes serious again, but after the laughter I feel relaxed. As I watch events unfold, I expect to feel self-conscious about my swearing and aggression. I expect it will look lame and pathetic. But even I can’t deny…I look pretty convincing. I suppose it helped that the anger wasn’t fake.

  “First things first,” she says as I start hitting Rupert. “You’re a natural at this too! It’s extremely rare to find a lady who can give this kind of thing as well as receive, but you’ve done both extraordinarily well this week. Remember what I said: we don’t look for actors. You’ve done well because you are those roles when you’re in them. Ultimately, your skill set will mean more demand…and top dollar for you.”

  For the first time, I smile at the mention of money. Hell, I’m good at this stuff! Or at least some of it. It’s time I started to feel blessed.

  “Of course, there are aspects to correct. This worked as a trial for you as a dominant, because I engineered a situation in which your emotions bubbled up. It wasn’t hard to see you’d fallen for Rupert, and the coldness between yourself and Petra was obvious. And understandable, I think.”

  Oh, does she think Petra’s a bitch too? But she doesn’t dawdle on the topic. Pity. I’d love to explore it some more.

  “I was pleased with how it worked out. Your emotions took you to places your clients will find sexy. And you find it sexy…I can see your nipples from here! Not to mention the clear arousal on your face. The trick now is to find that sexiness without the need for emotional stimulation.

  “Perspective and a cool head, even when you’re being hot-headed, you understand? You had no right to any of this. It was, in fact, a fine line that you walked, but I’ve let it pass because it was an important moment for you sexually.”

  I nod, but I need her to piece it together a little better. Fortunately she does.

  “In the context of this school, you can’t beat Rupert because you feel wronged. He owed you no apology for anything. He may have played the guilty one, but if a client does that you must always be aware that he is playing. As a staffer, Rupert would be entitled to turn on a whim and strap you down. You see that, don’t you?”

  Her point of view is starting to come together. Not the sweetest thing to hear, but, as always, I can’t fault her logic.

  “It’s good that you got into the role as you did. That much was perfect. If it helps you to imagine that you’ve been wronged, or to concoct a story, that is perfectly fine. But you must always, always keep in mind that it’s not a real punishment. Live your role, but without delusion. You need to be ready to roll with changing situations and switch roles seamlessly. It will happen.”

  I’m laying into Petra’s peachy little bottom now. Miss Jackson coughs.

  “Similarly, if you’re working with another girl and you feel your client will appreciate such a course of action, you can do this kind of thing within pre-established limits. Again, you can use whatever mental stimulation you need. Again, always enjoy it. No acting, like I said.

  “BUT,” she says, pausing the video and raising a finger in front of her nose, emphasizing the enormousness of the ‘but’, “you have got to remember who you are. No matter how much you get into it, you’re not doing it for you. It’s extremely important, Emma.

  “Bringing personal relationships into play on a client assignment is exceedingly delicate. Many will love to see your passion for Petra or your passion for Sarah, very different though those passions may be. That passion is almost always a plus. But use them positively, and be prepared to switch them on and off, or switch them around. Because there may be a day when you’ll have to make soft love to your Petras and whip your Sarahs.”

  It’s a lot to take in, especially now that we’re moving onto a montage of my shower sessions with Petra.

  “There’s somewhat less positive passion going on here,” she smiles. “You’re getting there. It’s something we’ll work on this week. Enjoying a pretty girl’s body in front of your clients is something you’ll do a lot. You’ll get used to it. You may not like all the girls personally, but – unlike some of the male clients you’ll get – they will invariably be beautiful. One focus this week will be to teach you to love a girl’s body even if you don’t love her soul.”

  She pauses. This Petra thing is becoming an elephant in the room.

  “I can’t discuss another student in detail with you at this stage, Emma, as it wouldn’t be fair. I want you to focus on the constructive criticism I give you this morning, and make of that what you will. And remember you can learn something from everyone. I am okay with your room move, but in keeping with what I’ve just said, be ready for further encounters this week. And you’ll still be shower partners.”

  Further encounters. Fine. It’s just work. There’s no more crush, right? I’ll try and fake it.

  “You can’t try faking it, Emma,” says Miss Jackson, interrupting my thoughts with her eerie mind-reading. “Enjoyers, not actors, remember?”

  “I get it,” I murmur, nodding. “I think. But…then how do I not enjoy it too much sometimes? Like with Rupert?”

  She smiles. “You’ll become an expert at that. It’s about feeling the situation and knowing the client. You’ll u
sually get notes on your clients before an appointment, by the way. Anyway, never suppress your enjoyment unless you’re asked to play something like a rape or kidnapping role. Always enjoy. Control of orgasm is a separate skill, and we’ll work on it this week.”

  I nod and my eyes flick up to the screen again. There I am licking Miss Jackson, in this very room. We’ve gone well beyond the surreal now, and I blush furiously.

  “Good memories,” she murmurs. And then scowls at me when she sees my shocked face. “Gracious, Emma, not that again. Please!”

  “I’m sorry…it’s just…I feel like I’m watching myself in a porn movie!”

  “That’s exactly what you’re watching…and so? Do you know how many girls would kill to be porn stars?” She rolls her eyes quite unashamedly. “I think you’ve still got too much stigma stuff planted in your head. Your parents made you think sex is ugly and bad.

  “And in spite of your clear enjoyment of the actual sex itself, I feel you’re not always secure about your body, perfect as it is. And there are still moments of hesitation. I saw it when we had you naked around the house, and I saw it again out by the poolside. There’s still the odd moment of doubt, where you’re thinking this is wrong. It’s normal enough for a first week, but we need to get you thinking more like, say, Alyssia. You’ve got to one hundred percent love what you’re doing.

  “The beauty side of things is pretty much a given in this game, up to a point. But it’s not enough. Always remember, it’s your attitude that earns more than half your fee. Not your looks. There are some relatively plain girls out there pulling in the cash because people pay for their spirit. There’s at least one in your group with that potential.”

  She doesn’t mention the name again, but I suppose she’s still alluding to Alyssia.

  “A bored, disinterested prostitute never gets called back, no matter how gorgeous she is. I don’t think you’re going to have that problem, but clients also don’t like traces of guilt or insecurity. They’re clever, successful men and, they can sense those things from a mile off. You’re moving away from such a mindset, certainly, but I think I know what will take you past the point of no return. It will shout down your subconscious angel.”

  She opens her drawer and ferrets around in it for a moment. Then she pulls out a handful of DVDs. Porn.

  She pushes the discs across the desk at me, and I inspect them. Hot Wet Lesbians. Sordid Secrets. Anal Pleasure.

  “It’s quality stuff from one of the world’s best production studios. Absolutely hard and uncensored, yet beautiful – the sexiest porn money can buy. These are going to help you shake off those guilty feelings about sex.

  “I’ll have a television and player brought up to your room. I want you to spend time watching these thrice a day this week. That is your regular homework. And I want you to masturbate while watching.”

  Chapter XXV

  I stare down at the piece of paper in my hand. I think it’s actually been typed on an old-fashioned typewriter! The ink is still fresh on the thick, sweet-smelling paper. It’s a summary from my meeting with Miss Jackson. Sarah and I are lying on her bed, comparing notes.

  Miss Emma Carling

  Aptitudes & Skills you can offer:

  -Straight sex

  -Group sex (MMF, FFM)

  -Fellatio & associated oral sex

  -Subordinate BDSM

  -Dominant BDSM

  -Sex shows including solo masturbation

  -Anal sex

  -Double penetration

  -All role play

  I wonder what ‘associated oral sex’ might mean. Could it be that thing? The thing I can never turn down? I wouldn’t put it past Miss Jackson to read my thoughts.

  This is quite an exciting report card. Yet somehow morbid. And I’m glad there are no instructions to hand it to my parents. We read on:

  Areas for classroom treatment:

  -Basic technical skills in the above areas

  -Reading situations

  -Emotional detachment & focus on physical pleasure only

  -Enjoyment of giving pleasure as much as receiving

  -Control of orgasms

  -Self-esteem

  -Guilt

  Phew. It sounds like I’m going to have quite a week. The ‘school’ part of this whole thing is really coming to life. Although ‘control of orgasms’ definitely wasn’t on the menu at my secondary. And what’s this about giving pleasure?

  “Hmm, do they think I’m selfish in bed?” I muse.

  “Oh Emma,” Sarah sniggers, elbowing me playfully in the ribs, “they might have a point you know!”

  Do they? I guess I do get a little inattentive when I’m enjoying myself. Maybe. I don’t like to hear it. I drop the paper and fold my arms, feeling defiantly apologetic.

  I mumble at Sarah: “Oh, sorry…if I’ve…you know…”

  She kisses me lightly on the cheek.

  “It’s okay, babe. You’re halfway there. You definitely do need to enjoy yourself, and show it. You’ve got that right! And besides,” she pauses, licking her lips. “I could taste you down there all day long. It sure beats ice cream!”

  “Yeah, well, lick Petra out and ice cream is probably what you get!” I chuckle.

  “Ooh, witty!” Sarah laughs. “And bitchy! I like it!”

  I suppose it was a rather clever joke. Maybe I’m relaxing.

  “But I’m not allowed to take bitchiness into the bedroom,” I groan, running my hands through my hair. “I was told that in no uncertain terms this morning.”

  “You’re gonna be fine, Em! Here, let’s look at mine.”

  Sarah unfolds her little report card.

  Miss Sarah Smith

  Aptitudes & Skills you can offer:

  -Straight sex

  -Group sex (FFM)

  -Fellatio

  -Subordinate BDSM

  -Anal sex

  I can’t help noticing her list is a lot shorter than mine. I put my hand on her thigh, in case she’s upset.

  “See, I told you you were the superstar!” she says. “I guess none of us have ticked all those boxes you have. It looks like you’ve got the full monty.”

  She’s putting a brave face on, but looks a little down. I’m surprised role play isn’t there, or sex shows. I mean, she’s into drama after all! And double penetration is conspicuously absent, which seems odd after our hot session with the boys.

  “I guess they decided I’m too tight or something,” she murmurs, as if thinking about loud. “It was a squeeze, but I didn’t think I showed it. Looks like I’m not down for threesomes with men. I wonder what I did wrong?”

  I put my arm around her, hook my leg in between hers and try to think of something to say.

  “I don’t think you did anything wrong, lovely,” I murmur softly. “Maybe they just don’t want you to hurt yourself. They seem pretty all-knowing around here. Or maybe they just want you to take it slow for now. I’m sure this list isn’t cast in stone forever.

  “As for shows,” I go on. “That seems pretty unfair on you. Do you think they judge that on the showers? You haven’t even had a partner to play with!”

  She says nothing and looks out of the window. Then, “Yeah, but…I was called for a little performance with a toy on Wednesday. I guess…I guess they weren’t impressed.”

  Her eyes are a little cloudy, as if a storm of self-doubt is gathering. Acting is meant to be her thing. Her career, even. But judging from her report card, it looks like she’s failed in exactly that area this week.

  “Come on!” I say, picking up her piece of paper again. “Look how much fun stuff is on here! Never mind what’s missing – you’re still gonna get paid hundreds of Pounds to play in a threesome with a guy and a girl, aren’t you? It’ll beat rehearsals on a Tuesday morning by miles! Who knows…we might even work together some time?”

  I see her face light up considerably at that thought.

  “I’d like that,” she smiles.

  There’s a small gla
ss of gooey white liquid perched in the inkwell holder in front of me. It sits there, layered like cooling lava, patient yet expectant. Like a medicine you know you have to take sooner or later.

  “Miss Carling, please show the way,” says Miss Littlefair, a pretty mentor with a cute, rabbit-like face and blonde curls. “Drink up.”

  My heart pounds. Straight into the deep end in our first classroom session. Up at the front, in large letters on the chalk board, is one simple word: fellatio.

  Every one of us is in this class. As Miss Littlefair, oral sex specialist, explained when we took our places at the scratched, slanted wooden desks after lunch. “This is as fundamental an art as exists in your trade, ladies. At the high end, there is no such thing as a fellatio opt-out. It’s as much a necessity as having a vagina between your legs.

  “Same goes for swallowing. If anyone has a problem with it, I suggest you put up your hand right now and let me know. Because we’ll need to work on some spectacular skills in other areas if you want to have any clients.”

  She looked around the room, and everyone’s hands stayed down. I noticed a few nervous, darting eyes, though. Latifa, of course, was smiling broadly.

  “Before we go into any technical skills,” continued Miss Littlefair. “I want to isolate the taste and swallowing experience for you. It will help those of you who have little experience in this area. Trust me.”

  And so my mouth fell open as Wilfred entered the room bearing a tray of eleven little glasses of…yes, really. They’re double shot glasses, in essence. Gleaming with white.

  Oh God.

  “Our men have been working hard this morning,” she smiles as Wilfred distributes the cocktails, impassive as ever. “This seed is all from the gentlemen of the house, whom you met last week. Whose it is doesn’t matter. It’s important that your default is never to care whose it is. You must simply love the drink itself.”