Escort in Training (Emma Book 1)

by James Grey

  Resourceful…certainly. Against school rules? I’m not sure, come to think of it. What about discretion? I’m so confused. And why couldn’t I do that? Why didn’t I even think of that? And why can’t the one who did do that at least look like she hasn’t been shat upon by a seagull?

  Why does she even want to do this, if she doesn’t want to do this?

  Fuck her. I turn on my heel, walk back down the hallway, jump into Sarah’s bed. I let her have her way with me in the dark. And I make sure I come hard.

  Chapter XXIII

  The weekend is so, so welcome. Even though I come down with a minor cold. This always happens when stress is suddenly lifted from my life. And this week has been nothing if not stressful. But more because the highs have been so high, so intense, and because I’ve had so many new experiences. Not because I’ve had a load of pointless meetings and impossible deadlines.

  Every time I used to go on vacation from work, I’d get ill too. At least that’s one thing that doesn’t seem to have changed in this new life of mine. The other thing is the presence of an evil bitch. I can’t believe it’s taken me this long to realise just why Petra grates me so much. She’s a darn sight better-looking than my former manager though. It makes me shudder. Especially now I’ve had to admit that I must be a little bit bisexual. But I think that after Friday night’s performance, my crush is beginning to fade.

  It feels strange waking up with Sarah in my arms on Saturday morning. But more than anything it feels nice. No group showers, no wakers. Not for two days. We’re both a little fuzzy-headed, and I’ve got a cough that hints at more than just a hangover. With a reluctance that surprises me, I move to the other bed for the rest of the weekend, so she won’t catch anything.

  Only when we’re getting ready for breakfast do I get round to telling her about Petra and the money. The bitch’s mercenary, business-like way hit me hard in my drunken state and made me crave some hot, human sex. It drove me straight to Sarah’s flesh. I wanted to revel in the joy of her touches, and I did exactly that. It was my way of taking a stand of sorts.

  Now Sarah is wide-eyed as I tell her what I saw in my old room. “Wow, so you think they actually did business last night?” she asks.

  I shrug. “It’s what they do, isn’t it? They’re both already working. I guess they know how to spot an opportunity.”

  We’re silent for a moment, pondering.

  “I didn’t even see that conversation begin with the two old guys!” she muses. “I don’t understand how they made it happen. How do you begin a chat like that?”

  “I haven’t got the slightest clue, and I don’t think it’s me,” I answer, dragging on my favourite pair of tracksuit pants, one of the only items I’d brought from home. “I got the impression that if I do this work, it’ll be booked appointments. No touting.”

  She smiles back at me. “You’re gonna do this work, babe. You’re too good not to. You can be honest with me.”

  She’s right. But can I be honest with myself? Maybe not just yet.

  “We’ll see,” I shrug. “What about you?”

  “It’s still a weird thought, you know. I’m like you, Emma. I can’t really do the extroverted thespian thing the whole time. I’m shy and I wasn’t brought up for this kind of thing. I want to get better though. And at least I knew I liked girls before this week!”

  She winks at me, and I go red again.

  “I’ve enjoyed everything so far,” she goes on. “It’s been hot, hasn’t it? Nothing not to like. Okay, we’re very exposed and that’s been weird. I’m not really as confident as I’d like, but I’m getting used to it. I dread the idea of a first assignment in the real world. I think I’ll have shaky knees. It’ll be so tough. But I think I do want to give it a go. I like to see things through. And my acting career…it’s not happening right now.”

  “Ah, well, acting might come in handy,” I grin. “I mean, what if it was you with those two geezers last night? They’d have had to be pretty good...”

  “Yeah, true! Although from what you’ve told me, I can’t imagine our friend down the corridor does much pretending. And she seems to do okay.”

  I think for a moment. “I suppose…but does she really? I mean, if those two are that wonderful, then why are they here for training?”

  “Good question, Em…good question!” Sarah shrugs, slaps me on the bum and steers me towards the doorway. Soon we’re tucking into a superb fry-up thanks to Wilfred and Miss Honeywell. The creamiest scrambled eggs and crispiest, juiciest bacon. Fresh-squeezed orange juice washes it all down a treat.

  My illness is nothing major, but I stay in the room for all of Saturday. I think I’m just tired and run-down more than anything, and something’s attacked me while my defences are down. Sarah takes care of me, bringing me snacks and drinks all day long. I wouldn’t mind a television to flick through, but I must admit watching the news would seem a little odd in this time-travel experience.

  She even brings Miss Honeywell to me at one point. The kindly woman looks concerned, and somehow I feel embarrassed. She could be my mother, but she’s seen me naked and watched us all take part in an outdoor orgy. She’s handled my cream-soaked panties and dealt with the linen from the Lachlan Room.

  None of this seems to trouble her matronly way. She tuts and sticks a thermometer in my mouth.

  “Nothing serious, thank goodness!” she says when she retrieves it. “Rest up, hopefully you’ll be fine by tomorrow evening. Have yourself a couple of these pills after you eat. We need you fit for Monday, so let’s not take chances!”

  I nod and smile at her, and my stomach knots as I wonder what Monday has in store. Despite my state, it’s a good kind of knot.

  It’s still there when I wake up on Sunday morning after a solid ten hours of sleep. My throat’s a little sore but my head’s almost back to normal. As for that knot, it grows and grows throughout the day. At least that probably means my body’s defences are up again.

  It takes most of Sunday to work out what the knot really is. It’s a little thing that’s been nagging at me. Something I don’t want to say out loud to anyone, much less to myself. But as I take a sauna on Sunday evening to sweat out any remaining ugly stuff in my system, I’m forced to come clean with what that thing is.

  Cock.

  Is it an accident that I haven’t had a man since the middle of the week? Probably not. But with everything that went on with Sarah – and Carrie and Miss Jackson – I kind of forgot about that in the midst of all the lesbian firsts. The last time I had a chance at penetration was the chess game. The game in which I was never taken. And that was Thursday.

  Rupert, and the double-penetration session with the other two guys, seem like months ago. I sigh to myself as I own up to my surprising need for a man between my legs. I want to be taken!

  It’s not like I haven’t come several times, and come hard. It’s not like I haven’t had more action this week than I’d normally have in a year. I’m amazed at how strong and insistent my desires have become now that they’ve had a taste of regular feeding.

  Much as I have started to think about tonguing Sarah’s pussy again, I’m pleased that the urge to feel a good length in me is so strong. I really don’t want to turn into a full-on lesbian. Girls are new and fun and good…but it seems I do want the best of both worlds. Probably a good thing for…business.

  I’m alone in the sauna as I start to think about something very substantial pushing roughly in between my legs. I close my eyes and let myself imagine that feeling. I’ve come so much this week that I don’t feel the need to touch myself. I just go for the ride with my mind. It’s amazing what a feeling of fullness I can conjure up with nothing but my thoughts.

  After a few minutes, another odd things hits me. The shaft I’m imagining is attached to nobody in particular. I think that might just be a first. All I’m thinking about is the sensation, not the man. Rupert would have been part of the scene even three days ago…have I forgotten him already?


  I’m confused suddenly. I remember myself flirting with Wilfred as he served me tea and sandwiches this afternoon. Sarah was out walking with Latifa and Alyssia, and I had nobody for company. Wilfred! Our butler must be 65, and he proved entirely professional in deflecting my double entendres. What was I thinking chatting him up?

  Well…at the time, he was the only man in the house. Hmm. The only pair of trousers with something inside them. Clearly something in my subconscious, ravaged by five days without a man, took that on board, and it came out in behaviour utterly alien to me. Has one cock suddenly become as good as any other to Emma Carling?

  Am I turning into a man, ready to fuck anything with the right body parts? Christ almighty! Well, hang on…I didn’t actually fuck Wilfred, after all. That would be ridiculous! Although…perhaps no more ridiculous than what I presume Petra and Lilia did with those two pub regulars. But my mind is doing odd things.

  I can still picture Rupert, and I still know he’s wonderfully handsome. Yeah, of course I want to have him again. He’s had his punishment from me, and, more importantly, the thrashing broke my own bonds with him. I no longer feel worried about what he does. If I can have him, good and well. There’ll be better lookers, worse lookers, dildos. I’ll get my filling one way or another. He’s just one way of many.

  It seems I’m changing rapidly, especially now I’ve had a quiet weekend to take stock of everything. Maybe the illness was a blessing. By all accounts I missed out on a pleasant stroll and a good swim with the girls this warm afternoon, but it would have been non-stop chatter. Maybe more.

  I wonder, too, if Latifa and partner will end up getting her way with me this week, or if they tried it on with Sarah this afternoon. Oddly, I’m not bothered either way. I’m happy with Sarah for now. We’re a personality match and we get each other. It feels good to be taking my fledgling girl-girl steps, not to mention my fledgling hooker steps, with someone that shares a connection with me. But jealousy seems to be a feeling I’m losing.

  The burning need for male anatomy pumping me, though, has gone nowhere. My body feels back to full health by bed-time, but that little knot in my tummy is growing at an alarming rate. Add that to the nerves I feel about the week ahead, and I struggle to sleep on Sunday night.

  Chapter XXIV

  School’s back in session. It’s nine o’clock on Monday morning, and I’m sitting in Miss Jackson’s office once again. This time, though, I am neither naked nor bound. In the absence of specific instructions, I’m wearing a black skirt and white collared tennis shirt. It feels pretty sexy.

  I’m freshly showered. Just went through the motions with Petra again. It’s like a non-experience now. I feel healthy again, and I’m actually looking forward to this briefing. Miss Jackson’s smiling at me, and the vibe is different from the trying circumstances of my last two visits. We were promised more clarity this week, and I hope Miss Jackson is going to be completely open with me about the programme.

  What I really want to know is how I’m doing. I’ve heard mostly good things from the girls, but last week was so tumultuous and secretive that I still feel I don’t know where I’m really at. I’m hoping my mentor will give me some serious feedback. She’s sitting upright in her chair, looking far more professional than she did the last time I was here. So far, so good.

  “I hope you had a good and restful weekend, Emma,” she beams. “It sounds like you didn’t have much choice in any case! Are you feeling better now?”

  “Yep, I think I’m all good, Miss Jackson,” I reply chirpily.

  “Good, because you’re set for another busy week. And a fun one, of course!”

  I nod and smile, trying not to look too enthusiastic. Although that twist of need in my stomach is still pulsing away inside me.

  “So, you’ve made it through the first week, and believe it or not, Emma, you had a good one. I’m very happy with how you’ve come along. There is certainly work to do, but nobody has a perfect first week. We’ve looked for natural aptitudes, and we’ve found plenty with you, young lady!”

  “Thank you, Miss Jackson,” I say, hoping that this is the right answer.

  “Okay, you can relax a little this week, dear. Last week we pushed you in all sorts of ways, and it was important to see how you coped with an element of surprise. Or to put it another way, to see how you reacted without having had time to prepare.

  “This week’s going to be more traditional schooling. You’ll know what you’re working on and why. And where. And when. We’ll be running classes. They will be highly practical. Expect demonstration and participation. I think you know what I mean?

  I know I know what she means.

  “Not all the girls will be in all the classes. The sessions will focus on specific skills, so it all depends on the individual. One of the things we’ll do this morning is map out what you need to work on this week.

  “First, though, I want us to look back on last week in some detail together.”

  I nod. I want that too.

  Then Miss Jackson does something I didn’t expect at all. She reaches into her desk drawer, pulls out a remote control, and flicks on the flat screen television affixed to the wall behind her desk. She swivels her chair around so we’re both facing it.

  Holy fuck.

  The black and white image that first comes onto the screen is someone I know very well. I’m lying on my back, looking up at the camera. I appear to be naked, and there’s a man on top of me. I recognise him straight away. It’s Rupert. I know that scene.

  My heart thuds like a drum as I try desperately to think of a reason why this isn’t what I think it is. There’s a date and time in the corner, and it corresponds pretty much to the moment I first visited the Lachlan Room. The film is rolling, and his powerful hips are thrusting hard. Their rhythm is familiar. I’m running out of ways to explain this away.

  I’m flabbergasted, and fortunately Miss Jackson speaks first. “We couldn’t make it obvious, of course, but we did film everything last week. It’s essential for the purposes of reviewing your performances in a natural way. Don’t you agree, Emma?”

  “Um…I suppose...” But I just want to crawl into a hole. The girl on the screen – me – is making a lot of noise now, even though there’s a distant quality to the sound on this playback. Oh, but that girl is really, really enjoying what’s happening to her. Ouch. Of all the embarrassing moments of the past few days, I think this one is making me reddest. I think I look really silly.

  “We’ll go through your main encounters for the week with a little critique. It’s a really good exercise for you at this point. For a start, I really did love your reaction here! You come across as a girl who is really enjoying her sex. And I don’t think that was acting, was it?”

  “Erm, I don’t think I’m a very good actor…” I mumble.

  “No, and that’s okay, because we are not looking for actors here. We’re looking for enjoyers. And with some work, I think you’re going to be one of the best of them. You can start off by snapping out of this embarrassment.”

  She flicks the pause button and fixes me with the most serious look I’ve seen her wear all week. It’s sterner even than the one she gave me when I was hauled into this room as a guilty spy on Friday.

  “I’ve watched a ton of these, Emma. It’s just sex, and like all sex, it’s beautiful. Beautiful enough to make me jealous, okay? I can’t have you going red at the sight of you getting it on. Blushing is a bad sign in an escort. Nothing makes a quality prostitute blush. And I truly do want you to be a quality prostitute.”

  I nod, and try to look relaxed. I sit back in the chair and try my best to focus on just how much fun that fuck was.

  “I’m going to criticise you now and then as we work through this, Emma, but don’t take it the wrong way. Nobody expected you to be flawless last week. The reason we’re doing this is so that you are clear on what was good and what wasn’t. It’s entirely constructive.

  “Anyway,” she goes on. “I’ve got a fai
r idea of just how much you’ve come along since the week began. I think most of these scenes would be different if we filmed them again this week, wouldn’t they?

  I nod, thankful at the chance to say something more general. “I’m pretty sure of that – I’ve changed a lot. The learning curve has been more like…well, it’s been vertical!”

  She chuckles and rolls the film again. We join the action just as I scream my unforgettable orgasm. Yeah, it’s a good memory. I’m trying really hard to shake off the years of English piety right now.

  “He’s a bit special, isn’t he?” she muses.

  “Well…yes, I suppose he is.”

  “You certainly showed it. There will be times when you won’t want to climax quite so easily in the company of a good-looking client though. That will come with time and experience. Also, be careful with your language – not every client will appreciate the four-letter words. But I’m more concerned about what happens next.”

  We’re coming to the part where Rupert abruptly shoved me out of the room like…well, like a whore whose services were no longer required.

  “You get very upset at this point, Emma, and that’s totally understandable because you come from a normal background,” she remarks. “This was not a test we expected you to pass first time. It’s not something likely to happen all that often in the real world. But you need to be hard-hearted enough for this kind of scenario.

  “The notion of an emotional bond with any client needs to leave your head. Unlikely though it is, you need to be ready to be kicked out of bed like that. You need to be ready for it to happen without you climaxing. This is very important, Emma. Are you with me?”

  I nod, not particularly happy that she’s kicking romance in the guts like this, stabbing it with her high heels. But I know she’s exactly right. This isn’t a flowers and kittens game.

  “Don’t frown, girl,” she laughs. “Remember we’re preparing you for worst-case scenario here. Nine times out of ten you are going to have the most fantastic time. Like you just did on screen. And nobody can really ask you to leave their house naked, I assure you. But you’ve absolutely got to keep what happens with a client in perspective and enjoy it for what it is. Never get ahead of the moment.”