Escort in Training (Emma Book 1)

by James Grey

  When our visitors finally leave the room and Miss Jackson takes away our blindfolds, we all have dazed smiles on our faces. She winks at me and leaves us to loll on the rug for a few minutes, giggling as we try without success to work out who might have done what to whom.

  With the intensity of our days seemingly on the rise, so our food gets more indulgent, though not heavy. I try not to overdo it at lunch time, limiting myself to a couple of slices of sourdough and foie gras, followed by a refreshing bowl of fruit salad. It tastes so sweet I’d swear it’s just been flown in from Tahiti.

  In the afternoon I’m joined by the other girls earmarked for extra-naughty stuff, as we’re lectured by Miss Tottingham on anal sex and double penetration. We’re all given stretching aids and advised on how to use them safely before and during client visits. We’re reminded that all but the kinkiest clients will want us ultra clean down there.

  We’re informed that it’s very common for us to have to loosen up a colleague to prepare her for client entry, like I did with Sarah last week. Our anal mentor is full of tips I’d never thought of, and then we try it out on each other. I’m paired with Latifa and I stick a couple of lube-coated fingers up her butt. Miss Tottingham strides around the room, bending over for close looks.

  “We need to be sure you all have the capacity for this kind of act,” she muses as she bends over my Arab friend. “Some women are simply too tight. But as far as I can see, you girls are relaxed enough and accommodating enough. It’s great news for your earnings, not to mention a ton of fun!”

  I think it’s the first serious sexual contact I’ve had with Latifa, and I’ve barely registered it. I must be getting good at this dehumanization thing! She’s certainly purring on her hands and knees as I wiggle my fingers in her. I can almost see her smile bouncing off the floorboards.

  Then Miss Tottingham gives me a strap-on and tells me to fuck Latifa. I do it. She nods approvingly as she sees the Omani’s back hole stretch to a happy gape. Then each pair switches, and I’m on the receiving end. I enjoy it, and that no longer makes me blush. Though I don’t make as much noise as Alyssia, who is clearly thriving on Simone’s anal attentions.

  The first half of the afternoon passes quickly, in a blur of anal and double penetration. I can’t fault the lessons. Solid, useful, practical tips, followed by putting them into practice right away. In ways no warm-blooded girl would be likely to forget. Oh, I guess Petra might be in trouble then.

  We break for afternoon tea and cake, then there’s a more informal seminar for the whole class, which takes place in the drawing room. Miss Ridgewell, the busty, drop-dead gorgeous active hooker amongst the mentors, announces we’ll have a male guest speaker.

  And when I see who it is, I want to melt into the floor.

  Chapter XXIX

  There’s a flash of recognition as he walks into the room. Oh lord, I know this man. I’m just so shocked and dumbstruck that my mind struggles to pick out the right file on him. It feels like someone from my past.

  FUCK!!!

  This cannot be happening. I’m floored.

  No. Please, no. Let this be a dream.

  It’s the CEO of the company I just left. None other than Mark D. Spurring himself. Known as a prize dick to everyone on my floor.

  What are the chances? A million to one? I curse my luck and close my eyes. I hope I’ll open them again to find this awful vision gone. No such joy.

  I try to keep still whilst my heart goes ballistic and I feel the hairs on my forearms rear up. I unfurl the large collar on my blouse and pull it up to my chin, in the vague hope that it will somehow hide my face.

  It’s not the brightest room in the world. We’re scattered around on the antique furniture, and I’m perched with Sarah on a soft and comfortable, white sofa about half way back. We’re just in front of the fireplace, off to one side. Maybe I won’t be noticed?

  He doesn’t do a lot of eye contact as he starts to speak. When his gaze sweeps across the room, it doesn’t particularly rest on me.

  I am paying absolutely no attention to what he’s saying. Something about sleeping with a lot of outstanding escorts, and things a client likes. Instead, I’m racking my brains to figure out if he actually would know me.

  Let’s think about this, Emma. The guy used to strut around our floor roughly once a week. There must have been sixty people on our floor. And our company occupied about ten floors. Six hundred people maybe? Are egomaniac pricks good with faces?

  I never loathed him like I loathed my manager, but to me he was the not-particularly-good-looking poster boy for senior management incompetence. Rarely did a day go by on which I didn’t think a caustic thought about him.

  I don’t think I ever spoke to him. I was in a couple of meetings he addressed, maybe thirty of us in the room. I responded to maybe three email threads involving him. Was it really enough to have made any lasting impression on the guy? Right now I’m so desperately hoping that it wasn’t. I’d do anything for that.

  My eyes are firmly fixed on the floor. I’m still hoping against hope that he’ll just go away and not know that his very recent employee is a trainee at the hooker school, where he obviously gets a kick out of sharing his wisdom with the next generation on whom he’ll spend his money.

  At least he’s not married. I’ll give him that. So I suppose he’s entitled.

  And he is, today as always, very tastefully dressed. I steal the briefest of glances, and catch his eye.

  Crap! His gaze lingers just a moment, and I hope that shadow by the fireplace is super-dark. It’s a bright day outside, after all.

  I drop my eyes and watch with my peripheral vision. He’s pausing on a number of us now, while he drones on about attitude or whatever. Is he just checking out the talent, thinking who he’ll want to fuck when we’ve graduated?

  God, there’s a thought I’m not sure I wanted to have.

  I can feel him looking at me again, but I keep looking away, adding nods just to show I’m paying attention. There are two reasons he might look at you. One, he thinks you’re hot. Two…he recognises you. Which is it?

  I pray to God it’s the former. But if he thought I was hot, then wouldn’t he have stared at me when crossing my open-plan office?

  Well, maybe not. He was never the flirty sort during work time. Too busy being demanding, I suppose. Maybe he’s only attracted to hookers, whom he knows he can have any time he wants. My head is starting to hurt.

  Part of me is so deeply curious that I want to run up to him afterwards and ask if my face rings a bell. But that’s total madness. There’s a chance, just a chance, I might get away without being rumbled. Oh, to see inside the man’s head for just one minute!

  His entire lecture passes me by, and he looks my way a couple more times as I ponder the awful possibilities that would go with recognition. The moment he drives back into mobile reception, every one of my former colleagues could know what I’m up to. I feel myself turning a little bit puce at the thought.

  But wait, hang on. Even if he did recognise me, how could he spill the beans on me without having to explain what he was doing at a sordid place like this?

  I suppose he must have one or two trusted lads on the board who could spread a rumour on his behalf. If he were feeling vindictive. I suppose he might have reason to, given the way I left. But would news of my outburst have reached him in his glass office? Was I remotely important enough to his executive existence? Surely she wouldn’t have told him. There’s no way something like that would make her look good. Right?

  I feel completely powerless. If he’s figured out who I am, my mother could know about this whole escort thing by dinner time. I banish the thought as quickly as I can, because I would die of shame. If he hasn’t, then…onwards and upwards. But seriously, I’d have to sidestep any assignments involving the guy.

  My blood runs cold as I begin to think of various other former bosses, professional associates and well-off gentlemen my father knows. Will I not walk into a c
lient sooner or later and come face to face with somebody who knows me as Emma Carling?

  His lecture feels like it drags on for hours. I’m dying to whisper something about this madness to Sarah, but chattering in class would only draw attention to me.

  At last he greets us and leaves. For a moment I fear he might want to demonstrate something on one of us, but thankfully the whole thing is respectable. Miss Ridgewell takes over the talking, and I don’t listen to her either. Instead, it’s with much relief that I hear car wheels spinning on the gravel outside. At least the guy isn’t staying over.

  Then again, he’ll find cell phone reception in a few minutes. I tremble to think what might happen, and I’m overcome with a desperate need to check my Facebook. If horrible rumours are going around – and I have a couple of ‘friends’ who would be only too happy to share them – then I want to know about it.

  But I won’t be able to get online until Friday. And today is only Tuesday. It could drive me crazy.

  It’s Sarah who calms me down, of course. Once we get back to our room, I tell her the awful truth. She’s wide-eyed, but says she didn’t think Spurring had lavished any obvious extra interest on me. I breathe a little easier.

  She takes me for a sauna before dinner, which calms me a touch more. She tells me there’s no point worrying about it right now, and that, anyway, even if the world did find out, they have every reason to be jealous of me. Tons of sex and cash, remember?

  I’m still pretty sure I don’t want to share my whereabouts with the world all the same, but, surprisingly, she has me convinced enough to settle me for a couple of days. She’s right, there’s no point even thinking about it. She’s rather good at these pep talks.

  We shower and dress for dinner. I’m feeling a little bullish, so I go for a miniskirt with my red tank top. Petra stares at me after I whip it out of our closet and take it back to Sarah’s room. Well, she can please herself.

  I feel that sexy thoughts will do the best job of taking my mind off worldly concerns. If my parents are about to disown me for training as a sex worker, I might as well have all the fun I can now. Luckily, I suppose, I’ve got a solo class scheduled for after dinner. And it’s going to be with the glamorous Miss Ridgewell.

  I squeeze in my evening porn-watching homework before I turn up, rather excited, in Miss Ridgewell’s office. I’ve been told I’ll be learning about sex shows. I forgot that was on my list, and I’m not even entirely sure what it means. But bring it on, I think to myself.

  It’s a fun evening. I’m solo because of a timetable clash earlier in the day, so I’ve got Miss Ridgewell’s expertise all to myself. She tells me how I’ll often be required to masturbate for the viewing pleasure of my clients, explaining that it can be one of the easiest and most fun aspects of

  the job.

  “All you have to do is pleasure your own sweet self to the max, and show how much you enjoy it,” she grins. “Fun money, easy money, and no acting required!”

  She watches with approval as I show her how I play with myself, reminding me only that I can add variety by playing with my nipples and sucking my fingers. I nod, not wanting to tell her that I usually do those things anyway – this shy Emma still surfaces in the strangest of ways!

  Then she shows me another trick I really haven’t ever tried. With the help of some lubricant, she teaches me a couple of ways in which I can penetrate my ass and pussy with the fingers of the same hand. I like thumb and middle finger best, and file it away for future use.

  “That will drive them crazy, youngster,” she cackles. “And you too, by the looks of it!”

  Then she tells me that I’ll need to know how to perform lesbian sex for an audience. “It’s not the same as lesbian sex for yourself, which I know you enjoy,” she winks. “When you’re doing a show, the view must always be factored in. You need to lick a pussy whilst getting your body out of the way, because they’ll want to see. That kind of thing.”

  She pauses, walks across to a camera in the corner of the room, and flicks it on. I know what’s coming. I think vaguely about rogue sex tapes, but shrug to myself. I may have done all the damage in the world already, so whatever.

  “Let me walk you through some of the moves,” she says, turning my body to the camera and then standing behind me, kissing my neck softly. “Your audience is in the camera. See how I’m pleasuring you whilst also letting them see you take that pleasure? Natural pleasure is absolutely essential still, but you just need to tweak your positions a bit.”

  I nod and swallow hard as I feel my heat begin to rise. Miss Ridgewell makes me come twice during our session. There is no way this very tired Emma can bother about her latest worry as she drifts into the deepest of sleeps. I’ve never felt so wanted in all my life.

  Chapter XXX

  The next two days are a whizzing blur of sex. I don’t have much spare time or energy to think about Mark D. Spurring, or Petra, or the Pandora’s Box that I fear my Facebook might be when I get home. No point.

  Sarah is a great help in keeping me on track, my mind fixed on living and learning the sweet pleasures of the flesh. She helps me to stay focused and makes sure I don’t forget my porn-watching homework, which I’m starting to really enjoy. Miss Jackson can start unchecking that guilt box. We’re beginning to watch critically now, looking at how the girls suck cock, and debating which positions look sexiest to an outsider.

  I feel rude and naughty to my very core when we have these conversations, but in a good way, because I know that I’m going to do this. These movies are really about me. I have a growing suspicion that seeing Spurring has pushed me over the edge of not-caring. Though I still don’t want to think about it, the fact is that if my reputation in the outside world is in ruins, then this might be the only career option anyway. I may as well stick at it.

  Once or twice I imagine some of my more immediate ex-colleagues, the ones who obviously had a thing for me. That blonde guy who wore the pink shirts and once walked into the door frame because he was too busy admiring me. I bet he’d be intrigued to hear about all this. Would guys like him try and book sessions with me?

  Hah! But they couldn’t afford me! You really would need a CEO’s salary to have yourself a piece of Emma Carling. Glory, I feel so powerful.

  We’re treated to more lectures and more practical sessions. Miss Ridgewell is prominent, just like her magnificent breasts. Most of us are brought into the sessions on threesomes, where we explore boy-boy-girl and girl-girl-boy possibilities. Latifa and Alyssia lay on a superb demonstration that leaves Jack completely stunned and has me leading a spontaneous round of applause.

  A handful of us – the elite? – are given group sex training. Meaning foursomes and moresomes. Alyssia, Latifa, Simone, Petra, Lilia and me. We watch that scene from Eyes Wide Shut and we talk orgies. We can expect one a week on average, Miss Ridgewell tells us, and they’re terrific fun. Thankfully, given the scary abilities of some of my classmates, there’s no practical. Not yet.

  I’m still soaping up Petra in the shower in the mornings. Every now and then, I still catch myself admiring her. In spite of everything. The attraction is chipping away at my soul as I grow in comfort with my bisexuality, though I really don’t want to let it. What is my type? Surely not a cold, heartless bitch! I like a pretty, wholesome girl who is smiling and sweet.

  And yet, there is still this raw beauty about Petra that occasionally draws me in. Even though she hasn’t spoken to me for a week. Even though she makes another cutting remark during Miss Jillings’ session on beating, suggesting that ‘some people’ here can’t control themselves.

  I redden, because I know everyone knows what happened with me and her and Rupert last week. And I feel gladder than ever that I gave her that thrashing. She’s only justifying it more now. Miss Jillings says anything goes if the situation demands it and the client will like it. I’m not sure the situation quite demanded it last week, but then, it wasn’t a real client situation either. And anyway, those were t
he days of emotional, hung-up Emma.

  We play around with various instruments of pain, practicing on a dummy. Carrie shows she’s way out ahead of us with her high backlifts and a level of passion that’s off-the-scale mean. I watch her and I’m pretty sure my lashes aren’t quite such a turn-on for anyone wishing to be made to feel like a worm.

  “One tip for those of you new to this,” says Miss Jillings. “It’s a huge help if you can have a certain someone in mind when you’re giving punishment. Someone who did something terrible to you. Train your hand to feel like it’s hurting that person. It’ll be better for everyone, trust me.”

  Okay, well that’s easy. My ex-boss. She will be the one I imagine is getting it if I ever have to do this, even if, as will most often be the case, it’s a man I’m hitting. I try it on the second round of practice strokes, and feel my energy for the task skyrocket. It works!

  I’m actually seething about my former manager as I wander back to my seat. It’s a powerful image, somehow made more so by the fact that Spurring turned up. I guess that’s because if my professional life has been destroyed by that twist of fate, I can trace the whole thing back to her.

  I ponder this for a moment as I watch Petra. She’s really not very good. Even I can see that. I’m not sure why she’s been brought into this class. Did she really have thrashing people on her list of aptitudes? I know she can take punishment okay, but this looks like an area where you need to at least manufacture some feeling. And she ain’t strong on feelings. Plus, she isn’t physically strong. Lilia, at least, can get some force into her blows.

  And then I have a lightbulb moment. She. Is. Her. I mean, Petra. She’s my former manager! I’ve finally figured out just how it is that she manages to wind me up so much. Why everything she does gets to me. They’re fucking peas in a pod, apart from the fact that my boss did a fair bit more talking. But that nose-in-the-air haughtiness, that frigid coldness, that sniping way? Oh yes, they’d get on well.