Escort in Training (Emma Book 1)

by James Grey

  “I suppose I’ve been…well, it’s all been pretty normal I guess. I’ve been pretty careful, and I don’t really do one-night things.”

  I don’t mention the three or four exceptions to that. The times when some guy has caught me in the right mood at the right time. Or the time when it was actually two guys. Why do I feel the need to be modest in front of a whoring teacher? Damn this English repression.

  “Go on,” says Miss Jackson sweetly.

  “So…yeah, I suppose I’ve only had about six or maybe seven partners.”

  I look out of the window, feeling bright crimson, not sure what else to say. Is that a good number? Enough? What is she after? Kinky details? It makes sense that she might be.

  “I guess I’ve been open to suggestions when I’ve been with someone I’m really comfortable with. It hasn’t quite been all missionary position…”

  Dammit, this chick still won’t give me anything. She’s just nodding, waiting for more. I bet this awkwardness is deliberate.

  “I’ve tried a few pages of the Kama Sutra. And I’ve done some dressing up.” I feel the redness rising in my face. “And I kissed a couple of girls at university. Probably did a bit more exploring than that with my friends when we were kids, but I don’t think that really counts.”

  More silence, so I plough on, hoping that means it’ll be over sooner: “I’ve let a couple of boys tie me up. Mostly just silk scarves at home. A little more, once.”

  She looks at me with a twinkle in her eye. She raises an eyebrow, leaving the obvious question hanging in the air.

  “OK, once we tried strapping me to the bed,” I continue, staring at the floor. I notice that I’ve started squeezing my hands between my thighs. I wonder how far down my bare body my flush has travelled. “He added cuffs too. I was okay with it, I trusted him. He wanted to try spanking, and then he used a belt on me.”

  My arms are shaking now. Is it the revelation or the memory? It was just the once. And we were in a serious, steady relationship at the time. Surely it doesn’t make me a bad person.

  But I’m stopping here. No way am I going to tell her how hard I came that morning, or how I couldn’t sit down for the rest of the weekend. How I came even harder when he did me up the ass that night, hips slapping deliciously against my striped, punished cheeks as he pumped. Nice girls don’t….no, I’m not telling her this.

  She’s not getting everything out of me. I’ll keep that thing about having my nipples bitten hard to myself. I can’t speak about how I twist them when fingering my own clit, it’s too weird. Or that other thing I always say yes to...I just can’t talk about that.

  Doing it, maybe. Talking about it with a stranger? I’m not ready for that right now.

  And finally she lets me off the hook.

  “Thank you, Emma. I know that’s not easy, but it’s handy for me.”

  I puff out my cheeks as I exhale for what feels like the first time in several minutes. I don’t bother hiding my relief.

  “You can relax now,” she smiles, switching modes again. “Just a couple more routine things. For now, your schedule will not be revealed very far in advance. But I can tell you that tonight there will be a formal opening event for this class, in the main banqueting room downstairs. Dress is black tie formal, and it starts at nine o’clock. You’ll know your way around by then, as you’ll have a tour of the house and grounds this afternoon.

  “Your medical results from your checkup and tests in London last week have come through to us. You’re all clear, of course. I need to tell you that anyone you encounter here has been through the same process. This is a medically screened environment and no exceptions will be allowed into the house for the duration of your stay. So you needn’t have any worries about...expressing yourself.”

  To be honest I haven’t given that much thought. Probably wouldn’t have done until an inconvenient moment. Good thing someone else did.

  You’re going to be doing an awful lot of fucking this week, Emma Carling.

  “I also need to inform you of your safe word. If there’s one thing you need to remember, it’s this. Your safe word is simply ‘Rex’. It’s the same for all the girls. If ever you are uncomfortable in any situation, say the word. Is that clear?”

  I nod. I’m not really familiar with the concept. But again, they seem to have thought of something potentially useful before I did. This setup is professional. Weird, in every way, but professional.

  “It’s all in this indemnity document, which I need you to sign. It’s only one page, and it’s straight to the point. It really just protects the school from anyone trying it on with rape claims and the like. One or two girls have reacted strangely when they failed to make the grade.”

  She hands me a document typed on thick paper. It’s not your typical business paperwork. There’s no letterhead, the school is referred to simply as Cranleigh House and the other signatory appears to be a lawyer with an impressive list of qualifications following his name.

  It gives little away about who I’m really dealing with, but the contents are as straightforward as Miss Jackson says. Miss Emma Louise Carling authorizes the use of her body for any purposes deemed fit by Cranleigh House, unless she uses the safe word. Miss Emma Louise Carling expects to perform and submit to a wide range of sexual activities, according to the needs of any non-student present in the house, for the next two weeks.

  Seeing my full name all over the document hammers home just what I’m doing here. Oh fuck, what if this lawyer knows my Dad? Where’s this paper going to end up? I hesitate.

  “Take your time,” says Miss Jackson reassuringly. “I only want you to sign when you’re comfortable.”

  No, I really shouldn’t. Too much thinking about the possibilities is only going to scare me off. Instead my thoughts wander to the ‘wide range of sexual activities’. And all that that entails.

  Fuck it, Emma, you only live once.

  I sign away that life of mine.

  I’m back in my school uniform, and I’m outside for the first time. Actually, all of us are. The remaining eleven trainees have just had a light, sunny lunch on the terrace. Now we’re awaiting our tour of the house and grounds. Lunch was pretty much the first time I’ve seen any of them with clothes on. And I still have no idea if I fit in.

  I look around the group. After what Miss Jackson said, I’m not surprised I’m the only one in uniform. But it’s clear our wardrobes are all very different. One girl sports a wispy see-through dress I certainly don’t have in my selection. She wears a dark bra and panties beneath. And I thought I was brave with my choice.

  Most of the others are more modest: tank tops and denim shorts or miniskirts seem the most popular first-day option. Makes sense, in this boiling weather. Needless to say, scanning the terrace is like looking out over a sea of sexiness. This place is so artificial it’s not funny: where in the real world would you find one hundred percent of the women are perfect? And suddenly I’m not surprised I’ve encountered some bitchiness already.

  There wasn’t a lot of chat over lunch. We were left to ourselves, bar Wilfred’s comings and goings to serve us salmon and bruschetta, followed by a fresh, scrumptious Caesar salad. One of the confident ones, exotically beautiful with green eyes, suggested we all stand up and introduce ourselves. I didn’t take in many names, truth be told. I’m looking at their sleek, gleaming bodies, and pinching myself at the thought that I belong in this company. If indeed I do.

  Petra sat at the end of the table with her compatriot Lilia. At least she was ignoring everyone else the same way she ignored me. I made some effort to get to know the girl opposite me. She’s also blonde, but she actually had a smile on her. She’s particularly tall and it turned out she’s Dutch: good, no wonder she’s warm. I like the Dutch. Her name’s Simone and apparently she’s been flown over here by a sponsor. Is this the world’s top whore school or what? I wondered if I was the only English one here, but do hear a couple of home-grown accents further down the long, cloth-cov
ered table.

  Now a dark-haired woman called Miss Jillings is about to show us around. I gather she is another one of the mentors. Like my own, she is not especially attractive but has a certain something about her. It’s not the warmth of Miss Jackson though. This one radiates frigid authority more than anything.

  I’m looking forward to this tour. Hopefully I can just take things in for a change, with nothing being demanded of me. I’ll feel a lot more settled once I know where I am.

  “I hope your lunch was satisfactory, ladies,” Miss Jillings says curtly. “Please follow me.”

  We descend the stairs from the terrace, to the sumptuous kidney-shaped swimming pool. More than generous in size, it’s an outlandish thing to see in England, but this is one of those rare warm spells when it might come in handy. It’s surrounded by elegant stone paving and enough sun loungers for us all: certainly it is more set up for recreation than Olympic training.

  I’m starting to get a feel for where we are. This is the back garden, so the road we came in on is away to the right. I only know this because I hear a car in the distance: the hedge is particularly thick and tall all along the edge of the garden. We’re some way below the main house, but the enormous grounds seem to flatten out at this point.

  “I am sure many of you will enjoy the pool if the weather holds during your stay here. I trust you can all swim.”

  She doesn’t wait for an answer, but moves on down the manicured grass. Away to the left I notice a lawn tennis court, and a life-sized chess board. This place really does tick every country house cliché. Croquet too, perhaps? It takes us a couple of minutes to cross the expanse of lawn, and I’m startled to see how far away the house appears when I look over my shoulder.

  I want so badly to tell Mum about this amazing place and the treatment we’re getting. Since I got dressed in Miss Jackson’s office it’s been a thoroughly respectable lunch and walk about the grounds! I have almost forgotten what I’m here for. But of course I can’t tell Mum. She’d flip out. No, actually, she wouldn’t even understand what I was saying. My parents are English decency personified.

  The vegetation thickens now as we move lower down the garden. It grows more haphazard. There are a couple of large elm trees, and a couple of mulberry bushes with reading benches beneath. Away to the left, a couple of magnificent, aged oaks. Suddenly I’m not sure which way to look.

  “That wooden building up against the hedge is a sauna,” announces Miss Jillings. “The fire is always burning and it’s particularly pleasant at night, even in summer. You just need to throw some water on the coals to make them hiss. Please note that swimsuits are not allowed inside, in keeping with European hygienic tradition.”

  “Just like home,” Simone murmurs to me. I’m sure we’re allowed to talk, but nobody seems quite that comfortable yet.

  I raise my eyebrows and give her a genuine smile. Yeah, not surprised to hear Dutch saunas are naked. And naked seems to be a recurring theme around here too. I notice a couple of utterly exposed outdoor showers on a paved area just outside the sauna.

  “Ladies, we do guarantee your privacy here at Cranleigh,” says Miss Jillings in a louder tone. “At least insofar as outsiders are concerned. You will note the high hedges around the garden. They are very thick and nobody can see through them. The outdoor area is totally safe.”

  We pass more medium-sized trees: there are a couple of hammocks strung up between them. I notice a swinging bench hanging from one stout branch. Chris the chauffeur was right: these grounds really do go on forever.

  “This hedge up ahead is not the end of the land here, but it’s the last area you can access,” continues Miss Jillings. I notice how thin her lips are. I think I like my own mentor better. “This is the start of the Cranleigh maze. The entrance is at the end over there. Eventually it backs on to some of the estate’s grazing lands, but I’m sure they’re of no interest.”

  My draw drops just a little. A maze? In this day and age? And this is no miniature either. Its width occupies the entire width of the garden, which is easily a hundred yards. In fact, this far down, all I can see is trimmed hedge. Tall hedge to the right, presumably with the road running beyond it. Tall hedge to the left, presumably with fields beyond it. And, ahead of me, hedge – lower than the boundary fences – marking the front wall of this maze.

  In the far distance – perhaps a couple of hundred yards away – I can see a slightly taller wall of hedge, which I take to be the lower boundary she mentioned.

  “The maze is not to be taken lightly. It has been crafted by experts and is rarely navigated with success by a novice. We do not recommend entering it when you are hungry or impatient, unless instructed to do so. Having said that, the first of you to find the end of it may find the reward pleasantly surprising.”

  She does not elaborate on this. I notice Petra whisper something to Lilia, who chuckles and glances at me. What exactly is their problem?

  The garden tour complete, we move back into the house. The middle of the main wing is dominated by the banquet hall, which gives onto the terrace. The main entrance is from the central hallway inside the front door. To the left of the front door is the kitchen, a WC and a smaller dining room where we’ll be taking our meals on cooler days. There’s a selection of fruit and snacks on the side cabinet, which Miss Jillings says will be left for us at all times. The oranges, grapes and apples look delectable, and I make a note to do a raid later.

  “Follow me to the North Wing, ladies,” she says, trotting around the corner into the wing opposite our own. “This is the lounge, which is always open to you.”

  We gather in the doorway and take in the vast room. In the bottom corner of the U-shaped mansion, it looks onto the rose garden next to the terrace. Predictably enough, it’s old school in there. It’s bright near the windows and the one French door connecting to the terrace, but darker at our end of the room. There must be a dozen leather armchairs. A fireplace. Three or four sofas, including one of the longest I’ve ever seen. There’s no television, no concession to modernity. I doubt there’s much point asking for Wi-Fi access. Are we really going to need distractions, anyway?

  She moves on into the wing itself, apparently in quite a hurry now. “Here is the library, whose door is also open. On the right are three classrooms, which you’ll be getting to know next week. You’re free to spend time there whenever they are empty. Beyond these, as you’ll know from this morning’s interviews, are the offices belonging to myself and the other mentors. Miss Honeywell and Wilfred’s quarters are at the end of this wing. All of these are, of course, private and off-limits.”

  She stops suddenly, turns, and clears her throat. “Now,” she says, making stern eye contact with each of us before continuing. “The rules are clear. You may roam the house and grounds as you please. The rooms I have just shown you are common. But rooms with closed doors are absolutely out of bounds, unless you are invited in after knocking, or instructed to visit them. Primarily this means the top floor of the North Wing and the ground floor of the South Wing. Are we clear?”

  All of us nod politely. I notice that even Petra manages it.

  Closed doors. Oh, there’s that curiosity again.

  “Very good. You are dismissed until this evening’s function. Nine o’clock in the ballroom. Dress code is formal. Be prepared for dancing.”

  Chapter VII

  I’m deep into the getting-ready process. I’ve just showered again, this time without company and without the audience. Even the two chairs the men were sitting on this morning were gone. I’m starting to wonder if it was all a dream. I’d ask my room-mate, but she’s just so damn unapproachable. She pretty much acts like I don’t exist. Fine. Two can play at that game.

  She stalks out of the room in her towel. I suppose she’s heading for a shower too. I’m glad she’s out for a while: this room needs a chance to warm up. And I’ve got some thinking to do. What am I going to wear? What exactly is tonight all about, and where is it going? Every answer
seems to lead to another question.

  I’m excited, and intimidated, by all the choice in my wardrobe. And that I’m going to a ball! Time is on my side. The full-length mirror in my corner of the room catches my eye. I have an idea. Show me what you’ve got, Emma.

  I throw my towel down on the bed, turn on the light and step up to the mirror, my hands on my hips. It’s a long time since I’ve been able to check myself out like this: my mirror at home is tiny. I smile, because I do like my reflection. Especially when there’s nobody here to compare it to.

  My eyes are drawn to my breasts. I’ve always thought them my strongest feature. You couldn’t fail to notice ripe, lively nipples like those. They seem darker than the last time I looked. They protrude ever so slightly upwards, like strawberries leaning toward the sun, from bouncy coconut-sized mounds that scream vitality and youth. Any bigger and they’d be trying to droop, but these tits are just right. I cup them in my hands, smile at myself and nod.

  I cock my head to one side, pleased with the naked girl before me. She’s a tiny bit paler than I’d like, but that’s being English for you. The flip side to that is that she doesn’t much in the way of tan lines. Down there, I’ve got my usual landing strip. South of that, I’m freshly waxed. All very tidy, and I assume Miss Jackson approved of my efforts. She certainly seemed rather impressed.

  I turn around and look over my shoulder. Yes, this all looks very nice too. I can’t wait to see longer hair flowing down my back, but we’re looking good. My skin is having a good summer: it’s nearly flawless. My ass isn’t as tiny as, say, Petra’s, but it fits my average proportions well. It melts pleasingly into my thighs, which taper down into knees and calves a little more gently than some of the girls here. I’m not one for the anorexic look: there’s some healthy substance to me. More than one boyfriend has told me he liked that, so I’m okay with me being me.