Escort in Training (Emma Book 1)

by James Grey

  I pull the blouse off her and it falls on my feet. Over her shoulder I can see her black and white bra, all intricate and curly patterns, revealed. From this vantage point I can see right down her cleavage, all the way to where the generous space between her breasts loses itself in sombre shadow. Suddenly I felt an urge to run my hands over her bra. Why not, Emma? What did Latifa say? Going above and beyond is probably going to be good.

  So I do it. I haven’t looked at this girl twice since we arrived, and here I am succumbing to the latest surge of horniness. More than anything, it’s her smell that has me going. It’s like a scent from Eden.

  I’m not even sure I’m doing it for the people watching, but I’m aware they’ll likely approve. They’ll love that you love it. And all men like a bit of girl-girl stuff, right? That’s what the whole shower thing is about, surely? I feel like I’m ready to go with the flow.

  “Stop, Emma.”

  What have I done?

  It’s George who speaks. His tone is kindly and soft. He has an easygoing look about him, though he’s not classically handsome. He is clean-shaven with jet-black hair, and there’s a certain passion in his dark hazel eyes. He’s the kind of man you have no reason to argue with.

  “I want you to kiss. Kiss each other.”

  I feel a massive surge of adrenaline, but I hesitate. What’s this force that wants to hold me back at vital moments?

  You can do this Emma. You want to do this Emma.

  God, it’s been a long time since those drunken student snogs. I barely remember them. They weren’t real kisses. This is going to have to be. And I think I want it to be.

  We turn to face each other and Sarah gives me the demurest of smiles. It melts me. Her sharp face, nose stud and all, has left little impression on me until now, but this smile changes all of that. Her mouth splays a little more on one side than the other, and a dimple surfaces on her cheek as one eyebrow raises.

  Oh! Sarah won’t be short of business with a smile like that. She can charge double. I might pay her myself, the way I feel right now.

  Either she wants this too, or she’s a fucking good actress. Whatever, it’s working on me.

  I’m the taller one, so I feel like it’s up to me to take the lead. One hand on her waist, one softly on her nape, I probe gently with my lips, nibbling at this girl I’ve barely spoken to, much less know.

  My eyes close but I can feel that she’s still got some of that smile as she kisses me back. And my heart skips a beat when I hear a tiny mewl come from her – she does want this! And the fact that I care? I think Latifa would approve.

  From the corner of my eye, I notice the men loosening the belts on their robes.

  My hand roams to the small of her back as my tongue delves between her lips, mingling sensuously with hers. I mewl back at her. Press myself closer. Fuck, I had no idea how good this could be.

  Our tongues wrestle, but it’s mere love-wrestling. It’s soft, lubricated, warm and intimate, this moment. I suck at her salty upper lip, sighing again at the taste of her mouth, her skin. I hear a rustling away to my left, but I’m lost in Sarah.

  I’m surprising myself here. Naked, kissing another girl with abandon, so much so that I’ve forgotten the audience. Yes, Latifa would be thrilled with me.

  Robert’s voice brings me back to the room.

  “Thank you, ladies. We very much enjoyed that.”

  I’m loathe to pull away, but Sarah pushes me gently back. Then she pulls me close again, arm around my waist as we face them.

  My God, their gowns are both open. The bulges are exactly what I thought they were. George is enormous. I’ve never seen…such girth.

  The talk of anal sex comes back to me. I eye his member with apprehension and awe. Robert’s less overwhelming length begins to look as easy to handle as Petra’s finger might have been. Jesus, my thoughts are all over the place.

  “On the rug, both of you. Sarah, you just strip and be done with it.”

  Robert’s voice has taken on an urgent, no-nonsense edge. Clearly things are about to go up a gear.

  “How do you want me, Sirs?” I ask sweetly, feeling the tingle between my legs rise at the words. I’m in some form today, it seems.

  “I want you on your hands and knees, thank you,” says George. “Face away from me, Emma.”

  I do as he instructs, assuming a doggy position as I look across to see Sarah stepping out of her clothes. Why does being told what to do like this get me so hot?

  “Sarah, I want you next to her,” says Robert. “Right up close. Touching.”

  It’s beginning to sound like I’m going to have to handle George and his vast manhood. I hope I can. The challenge makes the dampness rise in my pussy, and the nerves jump in my tummy.

  She settles in next to me, pressing her side against mine as instructed. I feel very, very keyed up. I look across at her as I hear the men rise to their feet. I see Sarah’s plump lips pout, and I steal a kiss with her again. She returns it with passion.

  I am shocking myself deeply now. Where did my reticence go? But fuck, I’m so turned on. I have been all day.

  “Miss Tottingham? We’re ready for you.”

  It’s George who speaks.

  I’m surprised at this turn of events, and watch as the ‘anal specialist’ mentor makes for the drinks cabinet, opens a drawer and fishes out what looks like a container of lube.

  And now, my hands and knees buried in the soft fur of the rug as I await my fate, I begin to quiver.

  Chapter XII

  I don’t remember signing up for this. Oh, sure, yeah, I did sign up for this. But right now, on my hands and knees, naked and trembling, I feel like it’s out of my control. They’re so strong, so uncompromising. Responsibility for any of this is a distant memory.

  And I think I fucking love that.

  I can almost feel the shy, repressed Englishwoman scampering away in horror at what’s being done to her. While the rest of me shrugs, saying ‘so be it, you’re at their mercy. You’re captive. You’re here to serve. It’s not you asking for these things.’

  I wish they’d hurry up. I feel like I’m covered in static, that if I were touched now, an explosive spark would split the room. It’s a feeling I haven’t had for a long time. That job robbed me of a couple of my best years. Who knew I had so much lustful longing stored up?

  Something deeply submissive seems to have come over me since I knelt down. Without even being asked, I drop my elbows to the carpet, pushing my utterly exposed hind quarters high into the air. I bury my head between my forearms as a tiny little growl escapes my throat. Trying to bury the crushing need that threatens to kill me if I don’t get some soon.

  I can hear Miss Tottingham’s pointed shoes cross the hard, polished floor and stop on the rug in front of us. I can smell the leather and feel how she towers above our heads.

  “Sarah, please put out your left hand,” she says, her voice flat and neutral.

  I raise up my head to see what’s happening. The mentor bends down and squeezes some clear, jelly-like lube onto Sarah’s round, rosy fingers. She takes Sarah’s chin gently in her hand. I notice Miss Tottingham has short-cropped nails, and how Sarah closes her eyes and raises her head like a cat does when it wants its throat scratched.

  I think Sarah is spellbound too.

  Miss Tottingham sinks to her knees and whispers into the space between our ears. Her hot breath whirls in that void. It makes a strand of my dewy hair rustle against my temple.

  “I want you to prepare Emma’s anus for a man. You know what to do.”

  I really hope she does.

  I can’t wait for something, anything in there.

  What happened to my trepidation about anal penetration? I’m gagging for it.

  Sarah’s eyes are wide open again. Miss Tottingham releases her chin. There’s a moment’s hesitation on Sarah’s part, so slight that perhaps only I notice it. I’m noticing everything right now. Every sense is on high alert. Her eyes flick to mine for
a fragment of a second. I give her a tiny nod. One that spurs her to action.

  My desperate sense of touch feels a deep loss as her skin pulls away from mine. She crawls around behind me, and I drop my head to the rug again. It feels clean and new. I like the way the fibres feel against my forehead.

  Miss Tottingham’s shoes move away. Then I sense she is also behind me. So are the two men, their tools primed. Oh God, this is it.

  Some of Sarah presses against me again. She’s steadying herself. I feel her forearms resting on my sides.

  There’s a loud thumping. Is it her heart? Or mine? Maybe both. Holy fuck.

  My butt cheeks are being pulled apart, stretched by a pair of hands. I rack my brains: does she have long nails? I just don’t know.

  Fuck, it’s been a good couple of years since…

  I’m so excited.

  But jumpy.

  Please let her have short nails.

  Instinctively I widen my legs a little, push my butt even further up in the air. I am brazen today! But still my heart thumps. For all sorts of reasons.

  Her finger is rubbing at my rim. It’s cold stuff, that lube. I flinch a little at the temperature, but there’s nothing not to like about this gloopy massage.

  I panic for a moment as I wonder if I’m dirty down there, but I remember this morning’s shower, and Petra’s finger. Fuck, it’s the second time since sunrise that a woman has fingered my asshole. And it’s nothing to what’s coming.

  The thought makes my clit swell. Honestly, I can feel it happen. Another first.

  Now she pushes in. Oh, so gently! Sweet Sarah. If she has long nails, I can’t feel them. I gasp, as I always have. It’s a shock nobody can prepare you for.

  But even as she starts to wiggle a little, I settle. She takes in what’s happening, and goes a little further. She probes deeper. I whimper as she twirls some more. Loosening me, stretching me.

  I open an eye and look back beneath my dangling breasts. Miss Tottingham is knelt close to my rear, vigilant. I feel…like a centrepiece. The star of the show.

  Another finger. She twists them and turns them. My asshole relaxes, gets less taut by the second as she prepares me. Suddenly I feel I could hold her there all day. But I want to kiss her too! Oh, Emma, where are your thoughts running to now?

  After a minute or so of probing inside my increasingly warm back hole, I hear Miss Tottingham murmur approvingly to Sarah, and the fingers withdraw from me.

  “She’s ready, gentlemen.”

  Which one am I getting?

  Beneath my crouched torso I can see Miss Tottingham move away and resume her seat.

  I raise my head now, eager to know what’s going to happen. I’m startled to see both men rise.

  Robert walks around and stops in front of me.

  I crane over my shoulder and I see George kneel down behind me. Robert has lost his robe completely, but George still wears his on his shoulders. It’s open at the waist and his monumental erection is all I can look at.

  Hang on, why is the other one here? What am I expected to do? What would Latifa do? Should I take him in my mouth? Questions are flying at me.

  But before I can do anything, Robert motions me to kneel upright. I do as I’m told, and as I raise my naked front to his full view, that feeling of total powerlessness washes over me again. It makes my pussy gush.

  I feel George’s hands pull my knees apart. His own knees are spread too: I can feel them inside mine. I can also feel his terrifying length resting against my spine. Resting with intent. But I still don’t know quite where this is going.

  “Up,” grunts Robert, grabbing my butt so that I kneel in a higher position. I feel like a meerkat now. But so totally wanted it’s making my eyes water. George is nuzzling my neck with his stubble. Eyes. Watering.

  Now there’s a triangular tunnel formed by my thighs and the floor. As far as I can tell, the man behind me is mimicking the position. Robert slides feet-first into that tunnel and lies flat on his back.

  Oh.

  Wait.

  Now I think I know what’s happening.

  My heart beats with the speed of a butterfly’s wings, but crashes like thunder.

  Stay cool, Emma. Stay cool.

  I’ve never tried this.

  I don’t know if I can do it.

  But now I feel George’s hand push my upper body down towards the floor again. And I remember I don’t have a say in any of this. I signed that paper.

  My face is now right above Robert’s. I’m so turned on. Kissing him feels as natural as not kissing him would feel wrong. I plunge into his lips, no doubt still tasting of Sarah’s sweet mouth. The thought thrills me. The action pushes my ass into the sky again.

  And now George does it. I can feel his dick brushing up and down my crack, probing for that perfect angle. Sweet Lord, yes! Take him, Emma, take him.

  But I yelp, just a little, as he shoves. No amount of Sarah fingers could ready me for this. There’s resistance from my screaming hole. Not because it doesn’t want it. Oh no. It’s just too big. It’s not too big, Emma. Take it like a big whore.

  I’ve stopped kissing Robert for a moment as I wince. He pulls my head back to his.

  “I never told you to stop,” he says, in a tone you don’t argue with.

  I respond by kissing him harder than ever, even as my ass feels set to burst. Suddenly I feel that pop as George muscles past that first line of defence, my tiny pink hole simply giving up the fight. I gasp, suddenly a whole lot happier. I feel him pushing slowly in, as far as he can go. Which is as far as I can take.

  It feels like he’s touching my stomach. He rests there a moment. It feels explosively good. He is hard as a rock and I fucking love that feeling of being filled. His hands come down to my tits, and he pulls me up, away from Robert.

  “Come on Jones, your turn now,” says a voice somewhere behind me.

  Shit, here is it. Brace yourself now.

  My quim feels stretched and taut, somehow full, even without anything in it. It’s that huge cock in my butt! But Robert, lying beneath me, is nuzzling its lips with his tip. He, too, is on the prowl for entry. I close my eyes as my head swims with a mix of hot erotic cravings and trepidation.

  Not guilt so much. Not right now.

  George isn’t thrusting yet, but I can feel him twitch and pulse, deep inside me. This is the calm before the storm, surely? He nudges my hips forward with his, to give Robert a better angle.

  Robert brushes my clit with his tip as he fumbles towards my lower lips. I jump at the sensation. George feels it, squeezes my breasts a little. God!

  At last Robert presses into me. It isn’t easy. George has left very, very little room. Everything feels vacuum-packed down there. Now that he’s in, I’m not sure he’s getting out in a hurry.

  I close my eyes again and take a deep breath. I feel like a princess, utterly fucking worshipped.

  Double penetration. You’re actually doing it! Emma, you little porn star!

  Once again I’m being manoeuvred. Pushed down. I’m flat on top of Robert, and George is flat on top of me. I guess this man sandwich is the only way this can work. I spread my legs so access is easy from above and below.

  Holy fuck. Double access. Emma!

  If they start to move, I may not last long.

  I begin to kiss Robert again. I need a distraction, or my head will explode from the filling I’m getting.

  The thrusting starts. Oh boy. One from George. My cheeks fill with air. One from Robert. Fucking weird. Fucking tight.

  George. Robert. George. Robert.

  Ass. Pussy. Ass. Pussy.

  They settle into a rhythm just like that. I begin to enjoy it, this stretched feeling. I’m at my absolute maximum. I can’t tell one man from the other. It just feels like one massive thing inside of me, wanting me.

  I try to keep kissing Robert but it’s difficult. I keep being jerked. But every time I miss his mouth, it gets me off to think of why I missed it. I’m making noise now,
a throaty squeal with every hit. Even as I kiss.

  This is phenomenally fucking sexy.

  It’s almost imperceptible how they up their speed. The pattern remains the same, but the pulses get quicker. Robert’s doing very well: it can’t be easy from underneath. I suspect their balls must be touching. I’m majorly turned on to think they’d do that to have a piece of me.

  It chafes. It fills. It hurts. It has won me. Please don’t stop.

  I don’t scream words like I did with Rupert. But I don’t last long this time either. When I come, my ass is so stretched it feels like you could fit a baseball in there. It makes my cunt feel even more saturated. The thought sends me wild. There is no way I can hide my muffled squeals and tremors as I orgasm in my man sandwich.

  I came before the guys again. I don’t know if this is the right way around. Sarah, whom I’ve forgotten, appears at my side and whispers into my ear. Reminds me to keep going. I nod, suddenly aware of what a mess I must look. The perspiration is gathering on my brow as I’m pressed between their warmth, their movement.

  It’s no trouble, really. I’m still enjoying this. I keep kissing Robert, revelling in the aftershocks as the men pump themselves towards their climax. Sarah’s fondling my hair, and I feel bad for her being left out. Poor naked Sarah. She’s squatting shamelessly next to my head, and there’s no mistaking the creaminess I notice emanating from her denied pussy. She must be gagging for it. I look up at her with punch-drunk eyes.

  I bring my mind back to the job at hand. I’m not convinced I don’t come a second time as the men unleash into me. First a warm spurt of George in my butt, then a hot spray of Robert in my still-convulsing cunt. Alive as my stuffed orifices are to every twitch, I can feel each of their orgasms distinctly, squirming as I listen to their satisfied grunts.

  Hell yeah.

  I’m in a daze as Sarah and I swap roles and the gentlemen swap theirs. I’m sweating, reddened in places and still breathing heavily as I put my finger up her butt. I’m barely aware of what I’m doing. I’ve gone a little slack-jawed, and I’m long past the point of anything shocking me. I find the loosening of her puckered little hole quite therapeutic. A chance to get my breath back.