I awake with Emma in my arms, gazing at me with love in her eyes.
“Good morning,” she smiles, and all the incredible events of yesterday flood back into my mind.
“Yes it is, you gorgeous creature,” I reply, and she giggles. I kiss her, tenderly.
“Nice dream?” she asks. “You were smiling in your sleep.”
“It was wonderful — I was dreaming about you.”
She smiles and kisses me. “Good answer.”
“You were being a naughty girl.”
“Really? That doesn’t sound like me,” she says with a sly grin.
“I was dreaming about all those guys you said you sucked off when you were younger.”
“Ah, that would explain this, then.” She grasps my engorged prick with her delicate hand.
I groan. “Tell me about it. Your first time and all your cock-sucking!”
She squeezes my dick. “It wasn’t that many!”
“Ok. My first time was terrible. It was with my first proper boyfriend. We’d been together about eight months and he was drunk, and it just hurt, and he came inside me so I was panicked thinking I’d get pregnant…”
“How old were you?” I interrupt.
“Fourteen. Nearly fifteen.” She shrugs. “It was a mistake, and it put me right off! After that, I went out with my friends a lot more — like five nights a week — and because they were always hooking up with guys, I kind of did the same. But because I thought I didn’t like sex, I blew them instead.”
“You must have been popular!” I say.
She shrugs, embarrassed. “I don’t know. I stopped doing it when I woke up in some strange guy’s bed with no memory of how I got there. He told me we fucked and I just completely started crying and everything…” She shakes her head at the memory. “I must have still been drunk ‘cos he convinced me to do it again. And that was the first time I liked it.”
She’s still slowly, leisurely stroking my dick. I reach between her legs, finding her moist clam, and I gently play, slipping a finger inside.
“So how many guys have you had sex with?” I breathe.
“You were lucky thirteen,” she says, wiggling her groin on my finger.
“So you’re not so much of a slut after all, then?” I wink.
“Well, I met The Boyfriend fairly soon after, so…” I slide a second finger into her. “I sucked off a lot more.”
“I don’t know exactly…” she whimpers.
“Tell me,” I whisper.
“Forty or fifty, maybe.”
I pull her on top of me and spin her around so we’re in a 69, and I bury my face in her soaking pussy. She keeps stroking my cock, but faster now, and she licks it from base to tip.
“Actually, it was more like seventy,” she mumbles.
I start thrusting up into her mouth as I force three fingers into her tight cunt.
“Oh God,” she screams, “it was over a hundred.”
I hammer my fingers into her. She pumps my pole hard.
“And for most of them,” she pants, “I swallowed their cum.”
“SLUT!” I shout as we orgasm together, my ejaculate filling her mouth, and her’s drenching mine. I enjoy the post-orgasmic bliss, caressing her bum and covering it with little kisses, as she fondles my cock until it softens.
She turns back to lie alongside me, shows me my semen in her mouth, and swallows with a wide grin.
“You’re my naughty, sexy, dirty little slut, aren’t you?” I cuddle her to me.
She sits up, suddenly serious. “Yeah, about that,” she says.
“Listen, you have to know that I love you, I really do…” she begins.
I finish, “…but you don’t want to leave The Boyfriend.”
She smiles sympathetically. “Not yet. I might, I don’t know. I hope you understand it’s a big risk for me. We’ve been together twelve years, we’ve got this house and… I do love him.”
I nod. I don’t know what to say.
“This doesn’t change what we were going to do today. Y’know, if we can spend that week together, I really think I’ll be able to make the right decision. I could make a decision now but it might not be the right one. Do you think you can be patient for me?” she earnestly searches for my eyes, but I don’t want to look at her in case I cry.
“Anything for you,” I whisper.
She smiles and hugs me, and I hold her tight, not wanting to let go.
I’m waiting in the car, around the corner from the emergency clinic, while Emma gets the morning after pill. She’s been gone 45 minutes already, it’ll be lunchtime soon if she doesn’t hurry…
Here she comes, sashaying across the road, and I take a moment to enjoy the view. She’s wearing a summery, flowery, floaty, strapless maxi dress, with a thin belt that emphasises her slim waist and accentuates her bodacious bosom. The dress flows down to the ankle straps of her heeled sandals. Her hair’s clipped back away from her beautiful face and flows loose around her bare shoulders, and fashionable huge sunglasses hide her eyes that I know have a hint of the dark eye-liner that I told her make her grey-blues look extra smoking hot.
And with the morning British summer sun shining from directly behind, her dress is slightly translucent, and I can see what I already knew — no underwear. She’s so fucking sexy, even when in girly-girl cute mode.
I get out of the car and ask, “Everything ok?”
She nods and smiles. “The shop is a couple of streets down, we can walk it.”
“Ok,” I reply, and we set off. I let my hand drift down to her swaying bottom and rest it there, but she swats it away.
“Behave yourself when we’re in public!” she playfully scolds.
I make an act of sulking, which makes her giggle, but I do as she asks.
We reach the shop quicker than I thought. There’s nothing outside to give away what it is — the windows are blacked out and it doesn’t even have a name.
We walk inside, my eyes adjusting to the gloom. It seems we’re the only customers. This front section of the store is mostly magazines and dvds, but it goes back a surprisingly long way, and I can see a plethora of sex toys and kinky clothing. The young student behind the front desk tries to act cool, but I can see him eyeing up Emma.
“How did you know about this place?” I ask her.
“This is where Cathy brought me to look for that bridesmaids dress, remember?”
Cathy is Emma’s firecracker of a friend that I’ve never met — but have heard plenty of dirty tales about. She’s also the girl who wanted Emma to wear a pink latex tube dress to her wedding.
“Is it here? I’m buying you that dress!” I tell her.
She giggles. “I remember the way your eyes boggled when I first told you about that.”
“I’ll be honest,” I say, “the idea of you wearing that dress with your silver high heels has fueled more wanking sessions than anything else.”
She blushes and leads me to the back of the store. “The boots are back here, let’s get what we came here for first.”
I’m pleasantly surprised by the range and variety they’ve got. “Which ones do you like?” she asks.
“They have to be over the knee,” I say. She rolls her eyes with a grin. “Shiny black, pointy toe, not platform, but with a high heel…”
There are a few styles with that description. The question is, what material? I’m vetoing suede, but can’t decide between leather or latex.
“Ok, well these latex ones, I don’t think there’s any time I could ever wear them out. But these,” she picks up a pair of matt leather ones, “I dunno, maybe over a pair of jeans?”
“I said they’ve got to be shiny.”
She shrugs and, as she pushes some to one side to put them back, I spot the perfect pair.
“We have a winner.”
The student from the front desk has shuffled up behind us. “Er, can I help you with anything?” he stutters.
“Yeah, thanks, do you have these in a size 5 please?” I ask.
“I’ll go and have a look.” He trots off.
“Y’know, he looks a little familiar,” says Emma.
“If he knew who you were, he’d probably have said something,” I say, trying to put her mind at rest.
“I dunno, he did kind of stare when I walked in, maybe we know each other.”
“He stared at you because you’re a cute, gorgeous woman walking into a sex shop. It wouldn’t surprise me if he’s back there right now whacking off.”
Emma laughs and swats my arm, just as he returns.
“Do you want any help trying them on?” he asks.
“No,” says Emma, but I immediately over-rule her.
“Yes, that would be great thanks.”
She shoots daggers at me, to which I smile and wink, but she sits down (a little carefully, her bum is still sore from last night) and unties her sandals whilst the student unpacks the boots.
He unzips and holds one open for her, and she slides a petite foot into the sexy leather. She winces.
The student immediately apologises profusely, “I’m sorry, did I hurt you? I’m really…”
“No, no, it’s ok, I’ve just got this problem with my foot. It hurts when I bend it but it’s usually ok once I’ve got them on.”
The student breathes a sigh of relief but is quickly distracted as Emma starts lifting her long dress so he can put the boot on. His eyes are fixed between her legs and, although she’s trying to keep them together as much as possible, he must be getting at least a partial view of her newly-shaven slit.
Her foot is about in, but the student is struggling with the zip. Emma notcies where the student is looking and again scolds me with her eyes, but I’m enjoying watching.
“I think they’re too small,” Emma finally says, “have you got the next size up?”
“I think so, lemme check,” stutters the student, who slips the boot back off, throws it back its box, and hurries away, trying to hide his obvious erection.
“When he comes back, have a quick peek — he’s got wood.” I grin.
“You are so naughty,” Emma tells me, shaking her head but not able to hide her smile.
“Me? You knew we were coming to get these boots, and you chose to go without underwear…”
“That was your idea!” she protests.
I laugh as the student returns with another box strategically carried in front of his groin.
“Genius,” I silently mouth to Emma, pointing at myself, and again she shakes her head.
This time she doesn’t wait, pulls her dress above her knees and halfway up her thighs, and stares at me defiantly, sticking her tongue out.
I’m trying not to laugh at the student as he struggles to get the boot unzipped without tearing his eyes from Emma’s crotch. Amusing as this is, I’m hard too.
He holds the boot out for her, and again she winces as she slides into the leather. The zip goes up much easier this time, and the student runs his hands along the boots to smooth them out, taking a little longer than is really necessary.
“How does that feel?” he asks, and I smile at the double meaning.
“Really nice, actually,” replies Emma, and I’m not sure which question she’s answering. I notice her legs seem to have fallen a little further apart though, and her dress is a little higher up her thighs.
The student quickly helps her with the other boot, zipping it and smoothing it out, and he doesn’t stop until I say: “Why don’t you try walking in them?” and as he stands, disappointed, I whisper to him, “Give us a minute, ok?”
He nods and vanishes, probably to watch Emma on the security monitors.
Emma walks up and down the aisle, the 5-inch heels making her look really tall and slim, sticking out her bum and tightening her tummy.
“In that dress,” I tell her, “they could be ankle boots for all anyone knows.”
“Pretty slutty ankle boots,” she says, “except they’re not, they’re full-on hooker boots.”
The pointy toe, the wet-look material and the thin, high high heel all scream sex. I love them.
“Pull your dress up, let’s see them properly.”
She gathers the dress, easing it up her legs. The boots fit snugly all the way to the top, accentuating the shape of her lovely legs, and reach a good few inches above her knees.
“They are fucking hot. You are fucking hot.” I say. “Do you like them?”
“I don’t know when I’d wear them.” she shrugs.
“Fuck that. Do you like them?”
“Actually, I really do. I’m surprised, but… they feel really sexy.”
I smile. Excellent.
“I swear that kid could see how wet I was getting,” she giggles.
“You gave him quite a treat!” I laugh, picking up her sandles. “Now, let’s see about that bridesmaids dress.”
Emma sighs. “You’re encouragable.”
She quickly leads us to the correct section and finds the dress, but…
“They don’t have it in my size,” she says.
“You’re fucking kidding me.” I’m gutted, but grab one anyway. “We’ll see if they can order one in.”
It does look incredibly fucking hot — a very short, very tight, not-quite translucent pink latex tube, basically. I could easily believe someone could wear it as a skirt. As a dress, it will barely cover anything.
We continue toward the front of the store but Emma stops suddenly. In the butt-plug section.
I slide my spare hand around her waist and over her pert bottom, giving it a little squeeze. “So last night isn’t going to be a one time thing, eh?” I tease.
“Did I tell you about my friend Mandy? We were at lunch at work one day, and she started telling me about this guy she picked up that weekend and, apparently, he fisted her arse!”
“Yeah! Why she felt the need to tell me this, I have no idea, but I always kind of doubted her. But looking at some of these…” she points at some of the larger butt-plugs on display.
“I’ll get you one if you want one.”
She peruses the selection, and picks up a monster that’s 8 inches around at its widest point.
“See, I don’t think there’s any way I could ever fit that up there. You felt huge.”
“I guess you build up to it. Why don’t you get a couple of different sizes and see how you go?”
She nods and, after a couple of seconds of thought, hurriedly picks up a smallish metal plug and decent-sized black inflatible plug. She smiles at me, embarrassed, and totters to the front desk. I grab some lube for her, and follow.
The student’s eyes pop out of his head as Emma puts the anal toys on the counter.
“These, the boots, and this dress in a size 8, if you can get that in please?” I say.
“Um, yeah, we can do that, er, but we can have it made to order if you like, so it, er, fits as you want it?” he stammers.
“Ok, yeah, let’s do that,” I say.
He can’t suppress his glee as he grabs his tape measure.
“Let me just get some measurements.”
Emma rolls her eyes at me but looks amused as the student fumbles around measuring her trim waist and flared hips, then seems really unsure of himself as he does her chest, brushing her breasts more than once. I can see her hard nipples poking through her summer dress.
“Ok,” he says as he runs the tape down from her armpit, “now you’re pretty tall, and the dress would normally be about 24 inches long, which would end here,” and he puts his finger high on her thigh. “Is that ok?”
“Yes,” says Emma.
“No,” says I. “Show us 22 inches.”
“Oh my God,” Emma laughs, “you can’t be serious?”
“You can wear it a little lower at the top too,” I smile.
The student holds his finger at 22 inches, and I like what I see. “How far does it come down at the back?” I ask.
He moves the tape around. “Twenty two inches would be here,” he says, running a finger just below her arse, copping a feel again. I think I hear a slight moan from Emma, and she steps forward.
“I think that’ll do,” she says.
“Ok,” I say, “make it at twenty inches.”
Emma just laughs while the student writes down the details.
“That will be one hundred and forty pounds for the dress…”
“Oh my God, you can’t spend that,” Emma says, “I’ll never even wear it out.”
“It’s worth it,” I tell her. To the student: “Is it ok if she wears the boots now?”
“Yes, I just need to get the price and security tags off. They’re on the zip.” Which is, of course, halfway up Emma’s thigh.
Emma grins and, without waiting to be asked, lifts her dress above her waist, far higher than she needs to, her cunt on display to the whole store, red, wet and swollen. I’m slightly disappointed there are no other customers to enjoy it.
The student is frozen, lost in a trance, until Emma’s tinkling giggle wakes him, and he hurriedly cuts the tags off the boots.
“And the boots are one hundred and twenty,” he says, and I nod, nonchalantly.
As I pay, Emma fills out her address details on the form for the dress order, and the student puts her butt-plugs in an unmarked bag.
“Thanks for your help,” I say as we turn to leave.
“Thank you,” he replies, a little too enthusiastically, and then “See ya, Emma.”
She freezes. “How do you know my name?” she asks, puzzled.
“I’m Alan — I went to school with your brother, remember?”
“Oh my God, I knew I knew you!” Her face blushes a fierce shade of red, and I have to push her out of the door.
Outside, she’s all a-fluster.
“Oh no, no, no, what if he tells The Boyfriend? Or my brother?! Oh shit, shit, shit…”
“It’s ok,” I tell her, “if they disown you, I’ll take you in.”
Shocked, she stares at me. “This is serious.”
“It’s alright, honestly…”
“How can you say that? He saw my pussy! Worse, I SHOWED him my pussy! Oh God.” Then, suddenly, a light bulb switches on in her head. “Wait here.”
She disappears back inside. Tempted as I am to follow, she told me to wait and I know better than to disobey her when she’s in this kind of mood.
It’s only three minutes later that Emma hurries back out, grabs my hand and leads me away from the shop, her heels clicking quickly on the pavement.
“Everything ok?” I ask.
“I know this quiet little place around the corner, maybe we can get through lunch without somebody I know seeing me naked.”
Emma drains her glass, her second of the meal, and starts on the third that she’d already ordered. She hasn’t said a word except to order food and drink since we left the shop, and it doesn’t seem like she wants to.
I must admit, she’s brought us to a nice place. We’re on one of three tables outside, but it’s sheltered from the people walking past by a head-height (when you’re sat down) hedge. The waitress clears the dishes from the only other table that was occupied, and leaves us alone.
“Are you ok?” I ask Emma.
“I don’t know,” she says.
“I’m sure he won’t tell anyone we went in there.”
“I’m sure he won’t too, now,” she says.
“What did you say to him?”
“You’ll hate me if I tell you.” Her eyes fill up, and she blinks rapidly, trying to stop from crying.
“Hey,” I say, taking her hand, “nothing could make me hate you. No-thing. I love you and I always will.”
She smiles meekly, takes a deep, wavering breath, and blurts out, “I sucked him off and said if he told anyone, I’d tell his girlfriend.”
My face must have been a picture. A picture of genuine shock.
“And you know the worst thing?” she continues, “It’s not that I blackmailed him, it’s not that I cheated on The Boyfriend again, and it’s not that I feel like I cheated on you…”
She looks me in the eye, and I can see how sorry she is.
“…it’s that I’m still so fucking turned on.”
“That’s a bad thing?” I ask.
“Of course it is!” she cries. “I went behind the back of the people I love, and I enjoyed it!”
She wipes a stray tear from her cheek. I lift her hand and kiss it.
“Emma, I don’t care. In fact, I love that you enjoyed it.”
She looks at me, confused.
“I don’t mind you doing these things. Did you see me trying to stop him from looking up your dress when putting the boots on?” I ask.
She shakes her head. “I don’t understand. Why don’t you mind? The Boyfriend’s always trying to get me to cover up.”
“I reckon he’s just scared that someone else will steal you away from him, so he tries to hide you. But you’re too beautiful and too fucking hot for that.” She blushes. “As far as I’m concerned, as long as you came home to me afterward, you could do anything, or anyone, you wanted.”
Her jaw drops. “You can’t be serious?”
“I swear to you. I just want to see you happy. It’s why I agreed to give you a baby even though it would kill me inside that you were bringing it up with him. You could come home having gangbanged a stadium full of guys, but as long as you actually came home to me…” I shrug. “I find it really very fucking hot.”
“So…” she says, and I feel her booted foot against my hard cock under the table, and she smiles, “…you’re as turned on as I am right now?”
“You have no idea,” I tell her.
She smiles at me wickedly, and it’s so good to see, that I can’t help grinning like an idiot.
“I’m not gonna do any gangbangs or anything, I’m happy just with you,” she says, “but it’s nice to know I have your permission to be naughty occassionally.”
And, as if to celebrate, she pulls the top of her dress down to flash her tits at me, covering herself again quickly.
We both look around, checking there’s no-one around.
The restaurant is empty. We can hear people walking past on the pavement the other side of the hedge — if they stopped and peeked through a gap in the leaves, they’d be able to see us, but…
I reach across the table and pull her dress down again, leaving it below her ridonkulous rack. I hold both her hands, so to a casual observer it would look like we’re gazing lovingly into each other’s eyes, but I don’t want her to cover herself.
“You are hottest fucking woman in the world,” I tell her.
“Are you going under the table again? Because I promise I won’t hit you like I did last night if you do.”
I let go of her hands and am pleased to see she doesn’t adjust her dress, and leaves her breasts free.
“I think your dress needs an alteration, it seems such as shame that no-one can see those fantastic boots,” I say, grabbing a knife from the table. “You don’t mind, do you?”
She eyes me suspiciously, but nevertheless shrugs and smiles.
I move from the chair opposite her to the seat next to her, and reach for the hem of her dress. “I think you should have a slit in this; show a bit of leg.”
I saw at the flimsy material with the knife until the hem gives, and it tears easily now.
“Not too high,” she warns.
“Well,” I say, gently pulling at the fabric, slowly creating a slit that runs up the outside of her right leg, “I think it should at least go as high as the boots. I think an inch or two of thigh above them would be good?”
“That sounds high enough,” she smiles.
The slit lengthens, and more and more of her sexy boots come into view, until I reach the top. I run a finger along her bare thigh, and she shudders and whispers, “I’m so wet right now.”
“Oh God,” I mutter, “I think it would look good if it was another inch or two higher. What do you think?”
“Only another inch,” she breathes.
My trembling hands take hold and I pull, and the slit grows another six inches, up level with her groin. I push the flowery fabric to the side and her glorious pussy is exposed. We both moan.
Suddenly, voices and footsteps from behind as new customers are being shown to the table beside ours. Emma swiftly pulls her dress up to cover her tits and crosses her legs, which hides her cunt but shows an obscene amount of tanned thigh.
“I think it’s time we got back,” I say, and Emma nods in agreement, quickly gathering her things.
I paid the bill and we’re walking briskly back to my car. Emma holds the front of her dress together so it doesn’t fly open so much at the slit — I swat her hand away.
She lowers her head, a little shy, but leaves the dress to float about her leather-clad legs, so nearly showing a lot more.
“You remember what you promised me if I got these boots?” she whispers.
“Yep. I’m looking forward to it,” I tell her.
“I’m looking forward to it, MISTRESS,” she says, encouraging me to repeat after her.
“I’m looking forward to it, Mistress Emma. Anything your ladyship pleases.”
She smiles and speeds up, taking my hand and pulling me along until we’re back in the street I parked on.
We reach my car and she takes a quick look around. It’s deserted.
She leans back against the passenger door and pulls her dress to the side, revealing the inside of her soaking-wet thighs and her dripping slit.
“I need to cum, now.”
She pushes me to my knees, though I don’t need much encouragement, and I go to town on her hairless pussy.
“Oh God yeah, this won’t take long,” she says, and pulls the top of her dress down, displaying her gorgeous globes, pinching her hard nipples.
I lift her leg and put her foot on the wing mirror, opening her up. The dress is in the way so I yank at it, and it rips up past her navel to her sexy butterfly tattoo.
I stuff two, then three fingers inside her cunt, pumping them hard and she moans loud and long, then screams as her pent-up horniness finally finds some release, drenching my face in her orgasm.
I lick up as much as I can, then stand and hold her — I love this when she’s cum, I can feel all the little trembles and aftershocks, it’s like I’m sharing it with her.
She kisses me, tired but happy. “I don’t taste too bad, huh?”
“I fucking love the way you taste,” I say, and I rub my face all over hers, smearing her juices between us until she’s giggling.
“I don’t suppose you could help me out?” I ask, looking down at the tent in my trousers.
She pulls her dress back over her breasts. “Maybe when we get home,” she teases, “Though I’m not promising. You’ll do anything to make me happy, remember? I never said the same!”
We get in the car, and she immediately starts rubbing herself. I laugh. “Still horny?”
“God yes. Now, let’s go — you ruined my dress so I think I’m going to have to teach you a lesson!”
When a teacher tells you she’s going to teach you a lesson, it’s not normally a good thing. But when that teacher is Emma… she can teach me all she wants.
I made a promise. And when she’s finished getting ready, I’m going to keep it.
Not that I’ll have much choice. I’m currently sprawled out naked on the living room floor, my hands cuffed (I love that she already had a pair stashed away!) and my legs tied wide open, each to a foot of the sofa.
And my dick is pointing in the air.
I hear her heels coming down the stairs, painfully slowly. I strain to see, to try to catch a glimpse.
Eventually, she struts into view and strikes a coy pose, biting her fingernail — and my breath catches in my throat. I’ve never seen anything so hot in all my life.
She’s wearing her Little Red Riding Hood costume — a tiny red dress with white lace trim and a black bodice tied so tight around her narrow waist that her fabulous boobs nearly spill out the top; the red hood pulled up over her curled blonde hair; deep-red lipstick and heavy dark eye make-up that’s way over the decency-line and firmly in “prostitute” territory; and the finishing touch — the boots I picked for her.
“Fuck me!” I exclaim.
“I intend to,” she purrs, “but first, a little fun…”
She takes one step closer and pauses again, teasing me. I can now see up the frilly black skirt, and she’s not wearing anything underneath.
“Oh God. I love your pussy shaved like that, Mistress.”
“Thank you, Slave,” she smiles. “I still think it looks a little bare,” as she rubs a finger over it, separating her lips, “but I love the way it feels.”
“I love the way it feels too.”
She grins. “Cheeky.” She steps between my legs, standing near my groin. “You should be more careful what you say when you’re tied up.”
Testingly, teasingly, she rubs the toe of her boots over my balls. It feels so good that I can’t help but moan.
“Did I tell you to make any noise?” she scolds, light-heartedly.
“No Mistress. Sorry Mistress.”
“Do you like my outfit?” she asks.
“Best thing I’ve ever seen,” I blurt out.
“You haven’t even seen it from the back yet.” She pirouettes and it’s all I can do not to cum right there. The dress only covers half her perfect bum and, from my angle, I can see all of it.
Including the metal butt-plug she’s got stuffed up her tight arsehole.
She looks over her shoulder at me. “Is it ok?”
“You’d better not touch my dick or I’ll cum.”
She giggles. “You’ll cum when I tell you to, not before.” She bends at the waist, looking back at me through her straightened legs, and blows at my dick. The gentle breeze is almost enough, and I have to shut my eyes and really concentrate not to cum right now. She giggles again.
Then, without warning, she puts one stilettoed foot onto my stomach and transfers her weight onto it for a couple of seconds, standing on me. It hurts, but I don’t care.
She does it again, but this time steps on so her other foot is on my chest. I thank my lucky stars that she’s so light and trim, but it’s still painful.
And yet somehow enjoyable.
She steps off, examining the red marks left on my chest from her heels. “Oh, poor baby,” she coos, and kisses each of them better. “Again?”
“Yes please, Mistress.”
She smiles and steps onto my chest again, this time digging one of heels into my side. As a reflex, I recoil and nearly throw her off me.
“Keep still bitch,” she spits, really getting into it now, and digs her heel into me again. This time I take it.
She twists her heel and it stings, and burns, but I don’t move. To my own surprise, I groan.
Emma’s surprised too. “Oh, you like that do you?”
Without warning, she kicks my vertical pole. I wince, but it feels good. She kicks me again; and a third time, harder.
She walks up and down my torso. I hope she appreciates the effort this is taking not to spin away from the pain, but I keep telling myself that it doesn’t matter if I like it or not. She’s done so much for me. This is nothing.
She stands on my chest and presses on of her 5-inch heels against my cheek, stabbing it.
“Swallow this, slave.”
I open my mouth and eagerly take the heel inside, sucking on it. She fucks my mouth with it; laughs and takes it away, and walks off me.
“I think you were enjoying that a little too much,” and kicks me in the dick at full force. It hurts like fucking hell and I try to protect myself as best I can considering my bindings. Which is to say, not well, because Emma gives me two more powerful punts with the point of her toe, then jabs her heel into my ball sack.
I cry out in pain.
She kneels beside me, stroking my face, comforting me, “Oh baby, I’m sorry, hush, hush.”
She unties my legs, which I move and stretch, and then uncuffs my hands. I stand, uncomfortable and unsteady.
She takes my hand and leads me to the glass coffee table, using me to keep balance as she steps on top of it. Then she cuffs my hands behind my back and orders: “Kneel.”
I do. She squats, pulls me closer, and lays my dick on the table top. Uh-oh, this can’t be good.
Using the toe of her boot, she presses my somehow-still-hard dick into the hard surface. It hurts, but not as much as I thought, and is actually pretty hot. The sight of her insanely sexy boot on my dick is a major turn-on, as is the click of her heels against the glass.
She puts her hand on my head, steadies herself, and puts all her weight on my dick. Though still sore, it’s so hard, it stands up pretty well. She wiggles back and forward, which feels really good.
She steps off, giggling, then teases my rod with the heel of her boot. She puts some weight on with the point, and the pressure of that stiletto hurts a lot more, pain shooting up my dick. I struggle.
“Stay still,” she orders, and stamps on me.
“Fuck!” I scream out and pull away.
“Hey! Get back here this second!”
Slightly hesitantly, I do.
“We’re going to keep doing this until you can do it without making a noise, ok?” she tells me.
I nod, “Yes Mistress”.
She lines me up, teasing me, running her heel along my length.
Then stamps on me with her heel, suddenly. I can’t help but grunt at the pain.
She sighs. And does it three more times, quick and sharp, and though it hurts more than the others put together, I keep quiet. Or it might be that my scream was so high-pitched it could only have been heard by dogs.
“Ok,” she says, and I collapse onto my side, really struggling to hold back tears. She lands next to me, crouching, consoling.
“How about I kiss it better?” she whispers.
I shift to allow her access and wince as she puts my cock straight to the back of her throat, her saliva initially stinging where the skin has been damaged, but it soon becomes soothing and feels fantastic. I moan.
She purrs: “I’m so wet, I can’t believe you let me do that to you.”
I shift to stare into her eyes. “What will it take until you believe I’ll do anything for you?”
She smiles, slides up and kisses me, tenderly. We make out for a good five minutes until she tears herself away and unlocks my hand-cuffs.
“Do you think you could fuck me now?” she asks, fluttering her long eyelashes.
“I don’t think I’ll last long,” I warn.
“Neither will I!” She sashays to the dining table and leans forward over it, legs straight, arse in the air, inviting me in.
I stand and stretch my stiff limbs properly. She sways her bottom side to side, impatiently.
I move behind her, and rub my cock up and down her slit, bumping her little nub. We both moan. She’s right, she’s soaked. I ease inside, pushing as deep as I can, enjoying being able to feel the plug in her arse from inside her, then pulling back out and stabbing in again hard.
“Stay there!” she tells me, and I do, balls deep. “It feels so amazing, I don’t know how I’ve lived this long without it.” Then she laughs, “Oh God, I’ve become obsessed with sex. It’s your fault!”
“I would apologise, but I think that’s a good thing!”
I twist the butt-plug in her arse, making her buck back against me, groaning loudly. I swat her on the bum, and again. I can control myself no longer and begin pounding into her hard, the table shuffling across the room.
“I’m not gonna stop this time.”
“Don’t stop. I’m so close.” She rubs her clit furiously.
“Where do you want my cum?” I pant.
“On my boots. Cum on my boots,” she blurts between thrusts.
“Oh God,” I mutter, and slam into her, and she screams, one long scream until…
“I’m cumming!” she cries, and her cunt pulsates around my cock as she cums, her ejaculate squirting everywhere and all over her boots; and I lose it, pulling out and firing my hot load to mix with her’s down her leather-clad thighs and calves.
I collapse forward on top of her, and we stay like that for what feels like an age. Eventually, I shift her blonde curls to one side and delicately peck her on the cheek.
“I love you so much,” I tell her.
“I love you too,” she says.
I shift, pick her up, cradling her, and carry her over to the couch. I sit, cuddling her on my lap. Dressed and made-up like a complete slut, metal butt-plug still up her arse, cum-covered fuck-me boots halfway up her thighs — she’s never looked more cute.
“Was that how you wanted it?” I ask.
Her smile is a mile wide. “It was pefect,” she says. “I want to thank you for doing it.”
“You don’t need to. I enjoyed it too.”
“Still, it was my fantasy.” She stares into the eyes, open and full of love. “Let’s go get my pussy pierced.”
She’s said and done some things that have shocked me, but I don’t think anything will ever top that.
“Are you sure?”
“Well, I do prefer it clean-shaven, and it does look a little bare, and Cathy says her’s is amazing… You aren’t going to try to talk me out of it, are you?” she teasingly smiles.
Before she changed, I got some photos of her. I don’t think she liked the idea to begin with, but when I convinced her that I needed something to wack off over until I got to see her again, she got into it, licking our cum off her boots and teasing the butt-plug from her gaping hole.
We shared a quick shower. Knowing we had to hurry if we were going to get her pierced before The Boyfriend came home, we unfortunately had to forgo any playing, but I still enjoyed cleaning her. It was a very sensual experience and, although I’ve fucked and cum in all her holes, I’ve never felt so close to her.
So we’re on our way. I’m driving us to the same place Emma accompanied Cathy to when she got her’s done.
Emma’s wearing the pink Tinkerbell t-shirt she started the weekend in; a short denim mini-skirt; and sparkly pink ballet shoes with a kitten heel. With no make-up and her hair pulled back in a loose ponytail, she looks like a different person from just an hour ago; with the slut hidden away again, the cute girly-girl I’ve always known is back. Except…
I know she isn’t wearing any underwear. And our topic of conversation is a little racier than it used to be.
“If this can take like four weeks to heal… I’m going back to work in a couple of weeks,” she says.
“I don’t know what it’s going to feel like wearing underwear with it.”
“So don’t wear underwear,” I shrug. “I thought you prefered that now anyway.”
“Yeah, but not for work. I’m not sure so it’s a good idea for me to go into a class of horny teenage boys, feeling turned on.”
“Why? What might you do?”
“Send all the under-sixteens out of the room!” she giggles.
“You’re such a slut, I fucking love it.”
“Y’know, anyone else called me a slut, I’d knock their teeth out.”
“That’s because when I do it, it turns you on. You love being a slut for me.”
She pinches her thighs together. “Stop it, I don’t want to go in there all wet.”
We laugh. To think I was worried before the first time that sex might make things awkward between us.
“I suppose I could get some smart trousers that are a little looser…” she ponders.
“Terrible idea,” I say. “Dresses and skirts, definitely. They don’t have to be short. A knee-length leather skirt would still be hot.”
“I’m not supposed to be dressing hot! I’m the teacher!” she giggles.
“Doesn’t mean you can’t look nice.”
“Are you saying I don’t normally look nice?” she teases.
“No, you always look fantastic,” I tell her, “but, I do think you could change up your wardrobe a little. A leather skirt, some low-cut tops, some wet-look leggings…”
“I’m not really sure about those,” she says. “The leggings — they sometimes look like bin-liners.”
“I’m telling you: on you, they’d look amazing. You’ve got the legs and butt for them.”
“And you think the boys would like that?” she smiles.
“Fuck yes!” I exclaim, and she laughs.
“Maybe I’ll do some shopping before our next get together.”
“You should go back to see your brother’s friend; you’ll definitely get good service there!”
She laughs. “God, I don’t know if I could look him in the eye again after I swallowed his cum.”
My eyes pop out my head. She giggles, shaking her head, still a little embarrassed.
“Yep, that was pretty much the look he gave too!”
I love this woman.
“Ok,” she directs, “turn left here and then take the little alley on the right, there’s a car park round back.”
I go as instructed. The car park’s empty but for a Harley Davidson so, out of a new habit I’ve now learned, I pick the darkest, most secluded corner. I catch a slight hint of a smile from Emma.
Emma takes hold of my hand as we walk toward the front door. Nerves seem to have struck her suddenly, and she’s the cute, slightly shy, girly-girl I first met six years ago. I want to look after her, protect her.
I stop her as she’s about to push the door open. “Are you sure you want to do this? I don’t want you to do it just because I’d like it, I want you to do it because you want it.” I ask.
She kisses me and smiles. “I’m sure,” and she leads me into the piercing and tattoo parlour.
There’s only person inside and, from the Harley outside, it isn’t the bearded stereotype I’d expected. It’s a tiny young lady with messy chin-length blonde hair, red vest top, matching red platform ankle boots with a stiletto heel at least 7 inches high, and wet-look leggings in the style I’ve just been trying to convince Emma to get.
She also doesn’t have the plethora of tattoos and piercings you might predict. I can’t see a visible tattoo, and only her ears and nose are pierced.
“Hi guys,” she smiles — oh, and a tongue piercing — “I’m Leah, what can I do for you this afternoon?”
There was little to be seen of the finer detail of her bedlah save for the flashes of bright red diaphanous material that swept by along with the movements of her body. For some the improvised dance in which she was engaged would have been termed belly dancing, but Jemima had always hated that term. It was so typically Western to boil something so ancient and articulate down to a tawdry term that fell so far from the true nature of the thing.
To her the art would always be better called raqs sharqi, the dance of the near east, as it was named in Arabic. And the heart of the style lay not in the stomach, but instead in the movement of the hips and their synchronicity with the rest of the body. She had studied it for a number of years now and to her there was so much more to the form than plain gyration and show.
Jemima thrived on the chance to perform for a receptive audience.
And her most common audience of one in turn never turned down the chance to see her perform.
He had seen her dance many times before and the sight always fascinated him, but tonight there was an added element of anticipation in the air. Tonight Jemima would finally make her skill as a dancer an integral part of their elaborate ventures into playing fantastic roles in the pursuit of sexual exploration.
Sitting in the leather recliner and watching her private dance, he found that he was more entranced by her movements than ever before.
Jemima’s hair had been gathered up atop her head, pinned in place with decorative combs. She wore an embroidered bra and belt that trailed a small skirt of material, both were sewn with a fringe of coins that swung and rattled as she moved. Other than those common trappings of the dancer, she was naked save for a pair of panties and stockings in a red that matched the rest of the outfit, a concession to his fascination with the sight of her in such things.
She had been dancing for perhaps ten minutes before she twisted away from him, crossing the room to where a large basket stood in the middle of the floor. Jemima wove herself around it, making it the centre of her dance as she built to a climax, lifting the lid and slipping first one leg inside and then the other. Standing inside the basket, she continued to dance, taking the restricted space afforded by her position as a cue to concentrate on tighter and more writhing forms of movement.
Slowly Jemima wound herself down and into the basket, ever lower until only the upper half of her body was visible. She waved her arms like branches blown by the wind and began to sink further into the basket until her head was level with the lip. From there she grasped the lid with both hands and pulled it down on top of her, curling her body up inside the basket with all the skill of an amateur contortionist.
He waited for a moment to be sure that she did not intend to make another appearance, then rose from his chair and left the room.
Jemima pushed the lid off the top of the basket and uncurled herself from where she had been resting inside. Stepping out onto the carpeted floor of the simply furnished living room, she stretched the muscles of her body until the effects of her confinement were almost gone.
She was an experienced hand at the art of contortion and a few minutes folded up inside what to her was a fairly generously sized basket was nothing taxing. But what she was about to attempt would make far more demands upon her frame and she hoped that all the practice might finally pay off and prove her equal to the task.
Confident that she was alone and that there was no one able to see in through the blinds, Jemima stripped her dancing clothes off in a matter of seconds as she made her way to a trunk in the corner of the room.
She lifted the lid and pulled out a folded object made of green patterned latex that caught the light as it moved and small box of cosmetics. As she unfolded the latex, it reminded her of the garment she had worn when pretending to be a living flower with her feet sunk in a pot and her face framed by a circle of petals. But there would be no standing, rooted to the spot for her tonight as the nature of her latest costume required far more physical effort than the last.
Jemima sat in the recliner and began to prepare herself for the task ahead by first removing her dancing clothes; something that took next to no time thanks to their scant nature. Once she was naked, she unfolded the latex body stocking and pulled it over her legs, pushing her feet into the end until she felt them slip inside the padding a the base of the costume. Like many of the outfits she had worn in the past, there was no separating her legs and they pressed together as she wriggled into the costume.
Her hands and arms soon followed her legs into the sleeves of the stocking before she pulled the combs from her hair so that only the grips and pins beneath kept it in place. Finally she pulled the hood of the stocking over her head and zipped herself into the garment with a combination of experience and the flexibility of a dancer.
She fussed over the fit of the stocking and the lines of her body beneath its fabric, keen to make sure that the elaborate design upon its surface was aligned correctly. Unlike some of the similar stockings she had worn in the past, this one required Jemima to make sure certain things were in place so as not to spoil the illusion it was supposed to create.
All of which was made harder by the fact that the gloves at the end of its sleeves forced her fingers into the position of three digits rather than the five that she was more used to.
Save for a band of paler colouring that ran from the top of her forehead, along the entire length of her front and ended just before the very tip of the stocking, every inch of the garment had been painted to give the illusion of rich, green scales. They ranged in size from perhaps two inches in the middle of Jemima’s back all the way down to no more than a fraction of that size around her gloved hands. The pigments used were rich and vivid, designed to catch the light as they moved and present the illusion of reptilian skin. But the scales changed colour dramatically from green to a pale cream where they merged into the band upon Jemima’s front. There the detail of the scales became ever less distinct until they merged seamlessly into a tone that was almost a perfect match for her own human skin so that where her face emerged from the centre of the hood, its skin seemed to simply blend with the colours of the stocking itself.
Jemima stretched her three-digit hands and then gave the length of her body an experimental shake, pointing her feet upwards to test her control of the new shape she was forced into. She nodded to herself as a good three feet of the stocking rose into the air beyond the point where her feet were located. But that was all part of the effect, to lengthen her body by two or three feet and create the illusion that rather than ending where her feet lay, her form continued onwards before tapering into nothing at the tip of the stocking.
She smiled at the effect of the padding at the end of the stocking, confident that she could manipulate it to give the impression she twisted away below the waist into a serpentine tail.
After all, that was the idea, to transform her into a fusion of snake and woman so that she was able to perform a dance that fused sensuality with serpentine grace.
Opening the box of cosmetics, Jemima used pale tones to blend the edges of her face into the pale colours that surrounded it before pressing prosthetic caps onto her canine teeth. When she had finished she pulled back her lips to gaze at the sharp fangs they added to her mouth and ran her tongue over them, amused by the predatory quality they gave her smile.
Jemima had toyed with the idea of some form of prosthetic to simulate the forked tongue of a snake, but in the end she had reasoned that the combination of her costume and the fangs was enough. Trying to hiss and lash a tongue that was at the same time threatening to choke her might have detracted from the overall impression she hoped to make.
Finally she slipped the bra and belt of her bedlah back on over the top of the stocking and slid out of the recliner and onto the floor. She crawled the few feet back to the basket and slipped inside before using the weight of her body to stand it upright once more.
Then she waited and filled her mind with the thoughts of cold-blooded creatures intent upon catching their prey.
The idea for this encounter had grown from a chance glimpse of an old film late one night, between the end of something that they had wanted to watch and finding something to stare at once it had ended. Neither of them had seen the film in question, but they both recognised the extravagant setting and seemingly obligatory overacting as belonging to the venerable Hollywood outings of Sinbad and his mock-Arabian adventures.
In the scene they happened upon, a wild-eyed sorcerer performed for the amusement of a sultan and his court, his innate villainy betrayed by his black, billowing robes. He might have flicked the remote and left the scene behind, but the sight of a woman being enticed to climb inside a large clay jar made him pause for a moment.
He had always been intrigued by performances of stage magic, hoping that there might one day be a magician who turned his erstwhile volunteer into something fantastical and alluring rather than simply making her vanish or sawing her in two. So he watched with growing interest as the bearded stereotype cast a snake into the jar with the woman, all the time chanting his magical spell over the vessel.
Soon the sorcerer was brandishing an axe with which he smashed the vessel into pieces as his spell reached its climax. The shattering of the clay was replaced by the cries of the assembled court as they saw that the woman and the snake had been replaced by a bizarre amalgamation of both creatures that had entered the jar. In their place was a creature with the head and torso of a woman, but below her waist curled the tail of a snake.
At the command of the sorcerer the creature danced before the awe-struck court, but by that point they had lost interest in the film itself. The stop-motion creature was rendered ridiculous by the proportion of its limbs and the constant cutting between close-ups of the actress daubed in cosmetics and the gyrating model failed to associate one with the other. In the end the creature more resembled a fitting plastic model than an exotic and unnerving fusion of woman and snake.
But by that time they had both lost interest in the film and its preposterous storyline.
They were convinced that they could come up with something far better themselves.
Jemima heard the sound of the door open and followed his progress across the room from his footfalls until he reached the recliner. She almost smiled at the oddly recalled fact that a real snake would have been forced to rely on the vibrations that his passage sent through the floor. But unlike a real serpent, she was not deaf and her prey could not hope to escape her attention in that manner.
She waited no more than a few seconds once she was sure that he was seated in the chair before starting her performance. He had no concept of what was in store as far as the content of her own dance was concerned and she intended to catch him as much off guard as she could.
Jemima pushed the basket over, throwing her weight forwards so that it turned away from the recliner and cast the lid across the floor. Her efforts meant that when the basket came to rest, it was roughly lying at eleven o’clock to his position in the recliner.
From his vantage point, he glimpsed the top of her green-clad head as she slid her arms out of the basket and reared her upper body like a snake uncoiling to scent the air. Jemima turned her head and regarded him from the corner of her eye, her gaze seeming to notice him for the first time and the edge of her mouth rise in a predatory grin of anticipation.
She pulled yet more of her serpentine body from the basket, turning towards him as she did so and keeping her eyes locked with his. Jemima had spent some considerable time preparing for her role and she was able to draw her restricted form behind her and then draw it forward as if preparing to strike, all the time making the motions seem as natural as possible.
By the time the tip of Jemima’s tail emerged from the basket, she had crawled around so that she was laid in front of the recliner, propped upon her arms and regarding him with the same interest that she might have given to a rabbit, petrified by her hypnotic glare. She added to the pose by deftly flicking the end of the tail and parting her lips to reveal her fangs as she did so.
Now that she had her prey entranced, it was time to bend him to her will with the movement of her coils and Jemima reared up to stand in front of him like a serpent ready to strike. But rather than try to rise immediately to her feet, she instead rose up using onto her knees, keeping her balance and moving her tail to create the illusion that she was able to bend and twist herself in any way she chose.
From her kneeling position, Jemima was able to once more resume the dance she had begun before donning her costume. She made ample use of the remainder of her bedlah, shaking the waistband and moving her breast in time with her thighs, buried as they were in her tail. For all the world she looked to have been transformed from the dancer who climbed into the basket to a supple, writhing snake-woman who continued to dance now filled with the deadly instincts of the creature she had been merged with.
Jemima became more and more impassioned as she danced, the need to express the sinuous and fluid movements of a snake seeping into her unconscious mind until the task seemed second nature and the limitations of her costume were replaced by the realities of her form.
She sank back onto her belly and arched her tail over her head, gripping its tip with her three-digit hands before returning to her kneeling position with it curled beneath her. The fingers were still dexterous enough to make the sight of her slowly stripping off the bra and waistband of her bedlah a miniature dance in of itself; a dance that ended with her pulling herself up to the recliner and placing her head mere inches from his groin.
Jemima stared up at him, the look in her eyes far from seeking permission to approach, were instead filled with the same predatory glint that had characterised her performance. He remained as still as a rock, staring back at her with a mixture of what might even have been genuine fear showing in his eyes and excitement showing in his crotch.
There was no way that she was going to wait for permission this time.
Her hands slid to his flies and a moment later they were beyond the zip and cradling his penis, removing it from his trousers and bringing it into the light of the room. Jemima pulled herself forwards, her arms reaching around his thighs and her torso pressing down into the seat of the chair as though she intended to slither over him.
As soon as she was close enough, Jemima teased the head of his penis with her tongue. The points of her fangs were sharp and he let out a strained breath as they grazed the most sensitive part of his member. But she was not doing this simply to torment him, and she soon closed her lips around the head and swallowed him deeply into her mouth.
He looked down at the sight of her body as it twisted away beneath him and swore that the rhythm with which she was twitching the tip of her tail was the same as the one with which she was massaging his penis inside her mouth.
Satisfied that she had aroused her victim to the point she desired, Jemima released his penis from her mouth and reared up so that she could climb up his body. She pulled herself over his naked member, ensuring that the sensation of her body beneath the latex only added to his stimulation.
When they were face to face, she drew her tail up into the recliner and arched her body so that she was able to inch herself down into his lap. A previously concealed opening in the fabric of the costume parted at slightest tug from her hand and she lowered herself onto his erect penis as slowly as she was able. She slid down sit in his lap with all the serpentine grace that she had demonstrated in her dance and once her buttocks reached his thighs, she began to replicate her swaying dance as far as possible, twisting his member inside her body.
At the same time she curled her tail so that it wrapped around his legs, pulling him in to her like a snake crushing its prey in a deadly embrace. His own hands reached around to seize her breasts through the latex, massaging them and pinching her nipples as she rode his penis beneath her. Jemima’s mouth opened in a silent gasp of sensation, her fangs bared as though she was prepared to bite into living flesh and deliver a dose of lethal poison.
Soon he could take no more and his climax saw him grip her serpentine body almost with a strength that caught her by surprise as he pulled her bodily down onto his member.
When he was spent, Jemima pulled herself off his penis and gently reclined the chair, sliding herself on top of him as they came to rest. She guided his hand to the opening in the back of her costume and he understood her intention despite the fact he was falling into a state of relaxation bordering on torpor after her attentions.
As his fingers massaged her towards her own climax, she lay on top of him and allowed his free hand to stroke the smooth curves of her buttocks through the latex, the length of her tail twitching in pleasure at his attentions.
It was a long time until morning, and she found herself enjoying the role of a cold-blooded predator more and more the longer she played it. There were no complications to he had here, she saw what she wanted and she took it.
Wouldn’t life be so more simple, she thought, if all we had to do in life was rear up on our tails and pounce on what we wanted with fangs bared?
Chapter 14 The Finale
I awoke very late, or at least it felt late. Lisa was gone but I could hear the shower running. “Are you OK, darling?” I called but she probably didn’t hear me over the shower. I got up and felt the usual delicious tingle as the sheer fabric dropped over my smooth skin. I padded to the bathroom and was rewarded with the sight of my beautiful Lisa through the shower door. I called again but she didn’t stop washing herself so I popped my head round the shower door only to have my left breast form and my nightie soaked as Lisa splashed. I did fleetingly see her striped arse as I yelled and drew back.
“Sorry,David I didn’t see you there,” said Lisa as she temporarily stopped her ablutions and popped a wet head round the shower door.
” I was just a bit worried about you, baby,” I simpered and Lisa gave me her usual winning smile, “I am as fine as I can be considering…,” she said, “and I am glad that is over for another year. I will have to see if I can get out of it next time.”
I nodded assent and hmmmed as one does when one is not entirely believing but disinclined to challenge.
There seemed little point in standing about in a wet nightie so I promptly took it off and joined Lisa laughing and giggling in the shower. I felt really close to her as I helped her bathe her ravaged body and she soaped me all over. Lisa was really cheerful and only winced when I touched her bum. She exited the shower first and left me in the hot spray to rinse off. Once again, when I had exited the shower we used the usual copious numbers of towels to dry ourselves and then sat in front of our massive bedroom mirror to apply make up and dry our hair.
My own natural hair was growing nicely and I now had enough length for a boyish sort of style but it was a little thin and I had fine hair. As Lisa pointed out, such hair was going to be a trial every morning to get any shape into it. The alternative was to shave it all off and glue a wig on semi permanently like my breastforms. Once a month maintenance rather than every day. It was an attractive prospect and, as Lisa again said, I still needed to do morning maintenance to my hair so still very girly.
The rubber was still where we had left it, in a heap on a chair. Lisa showed me how to rinse it through and dry it off. She also told me that the transparent rubber had been treated so that it didn’t need to be talced like the regular black or coloured rubber as she had worn. I enjoyed handling the rubber.
“Can I keep this stuff here, Lisa,” I asked as I towelled the water spots off the red bra.
“Oh yeah, sure. All the outfits in FemsRace are either in someone’s room or in the store.” Lisa replied,”and that stuff would only fit you or a man of your shape anyway so I doubt there will be much demand for it.” I promptly put the whole outfit on hangers and hung it in my wardrobe. I even stroked it as I closed the door and knew that I would wear the outfit again. I saw Lisa looking at me as I closed the wardrobe door.
“Addictive stuff,” she said and I nodded sagely as I felt the rubber again and imagined it on my skin. Lisa touched my arm.
“It is OK, David,” she said, “to crave all these sensations. I quite like rubber but always associate it with Mistress Amy. When I wear it I become submissive and self conscious so I have to be told to wear it, forced to even so I don’t just put it on to be sexy, if that makes sense.” She laughed nervously and I saw her shudder presumably at the memory of yesterday and I saw her stroke her bum through the towel, “but it is okay for you to wear it because you want to and I think I would like that for myself, you, dressed in rubber…for me, hhmmm.”
With that we giggled and embraced. My towel fell off my breasts and we laughed and started a play fight with me naked except for a towel on my head and she quickly lost her body towel too. I stole a kiss on her lips and my breast forms brushed her real ones. The laughing stopped and we looked at each other, breathing hard. The next kiss was long and passionate and we slowly entwined ourselves as we lost ourselves in the kiss. I ate her mouth and tongue and the kiss became greedy as we ate each other. I felt my cock stiffen and so did she. We parted and I saw the lust in her eyes.
“Save it, tiger,” she breathed,”my arse is not ready for you just now but I want you to fuck me properly tonight and I won’t take no for an answer.” With that she broke off laughing and we play fought lightly for another few minutes.
I think that I fell in love with Lisa at that point. It wasn’t a sudden rush and indeed, this story is a recollection of the events and, in the setting out of the events, it occurs to me that this was the point at which I just knew. I didn’t do anything or say anything at the time but somehow, in the recalling for this story, it was this point at which I realised that my love was actually there. I had been in love before or thought I was, but this was different somehow, stronger, more certain. I was still wary and knew that we had many hurdles to clear but at least I now knew what I wanted and that if anyone could share it, it was Lisa.
We dressed as always in our smart gear. As always my skirt was slightly too short and my suspenders too long but I didn’t care. I was aware that my time at FemsRace was drawing to a close so I could dress how I pleased here for the remainder of the time and I liked feeling sexy and slightly slutty and had no qualms about displaying my underwear and skin in this club. Lisa was only slightly more demure but we had agreed that we would both wear skirts and suspenders for each other. We clattered, giggling to breakfast and were like two schoolgirls as we nibbled out toast and discussed make up, hair and perfume.
We had sat opposite each other for once and during a silence I felt ready to broach the subject.
“Lisa, darling, do you think we should leave FemsRace,” I ventured,
I looked over at Lisa as she poured the tea. Her face was quite calm and I could see she was looking for the right words.
“You took the thought right out of my mind, David,”she said. I felt my heart leap. So this was it! We had launched the ship! No turning back now.
I won’t bore the reader with the logistics of what came next but within a month we had moved into a flat together. I had found a job through Carla working for one of her husband’s companies as a PA to one of his female managers and that was really cool as she knew that I was a T Girl and indulged me as I learnt how to be more demure in appearance, to blend in with the crowd. Both make up and dress were modified for that and she gave me time off to have my beard removed by electrolysis. I had taken Lisa’s advice about the wig being glued on and settled for a really lovely and very expensive shoulder length one in a neutral shade of brown with subtle henna highlights. I was now a full time girl and wore tights at work and regular bra and panties. My heels were only two inches and the shoes sensible, no stilettos at work.
I had some voice coaching and used a throat spray that a doctor gave me. I never got the musical quality that women have but I was much better than before and it gave me more confidence to go out on my own and, in particular to go into clothing stores on my own and ask to try things on.
I also noticed men looking at me and learned the art of avoiding eye contact and dressing to blend rather than to please. Eventually of course, I had to dress up and just go out to wow the men. I had been able to take all my FemsRace clothing with me and I did enjoy putting on a short skirt and suspenders with high heels, full make up and a sheer blouse and just going out on the town.
At home after work I usually stripped off to a nightie and peignoir and wasn’t allowed to put on any sweat pants or scruffy clothes. I had to be immaculately dressed or in lingerie. Only occasionally was I permitted to wear jeans or trousers and they were as feminine as Lisa could find. Only she could buy such items. Everything I bought had to be glamorous and I actually didn’t mind that. I was a T Girl not a woman so I had to be the best T Girl I could be. Lisa insisted and I wasn’t arguing.
I had also worn corsets for days at a time and my waist had reduced and I had the makings of an hour glass figure. My corset maker had warned me that any further reductions would need an industrial strength of corset and would give me sores so I settled for the ones I had and constantly dieted to get my weight down. I certainly lost muscle tone but my broad shoulders necessitated a large breast form. I did eventually have electrolysis and laser treatment on my body hair above the waist and on my bum but was advised that to do the legs would be difficult and costly and to depilate my bum crack would be risky. All are still regularly shaved. Fortunately my fine gauge hair on my head also extends to my body and Lisa has little objection to helping me with these difficult to reach areas. I obviously return the favour when asked.
Lisa was very much her old self and demanded that I fuck her on a regular basis. We both had other liaisons and I now have a regular boyfriend who I see as often as I can which is about once a month and we make love and it is wonderful for me to take his cock in hand or mouth and, after about four really hot dates, he lovingly penetrated me. It was a beautiful experience and I always returned to Lisa in high spirits and she always asked me how it felt and was happy that I was happy as well. We always made sweet and beautiful love afterwards and that also applied to her own lesbian encounters which were more frequent at about once a fortnight although her partners were different every time. Lisa did not want to take a lover as she felt that I was enough for her and that my cock was much better than a strap on and other men were out of the question as other women were to me.
I truly feel that this time with Lisa was the best of my life and I found both myself and the love of my life in Lisa and as a T Girl.
This all came to an end exactly three months ago when my beautiful and precious Lisa died. She was diagnosed with cancer of the pancreas and was dead within six weeks. After the diagnosis I was devastated and wept so much that I couldn’t wear make up. My boss at work was really supportive and gave me loads of slack and time off and made sure that the rest of the office gave me all the room that they could. By this time I think they all knew I was a T Girl but I had been there long enough and made enough friends that when they saw my grief they were touched enough to comfort me as a girl. Even the guys were really solicitous of me and when I saw or felt that I always burst into tears.
Carla, her husband and I buried Lisa with as much grace as we could muster.
My boyfriend was also really good and held my hand at the funeral and held me up when the coffin disappeared and I collapsed, overcome with grief and screaming for my beloved Lisa.
About a month ago I returned to FemsRace at the invitation of Carla but I think I wasn’t really ready for it. I didn’t see anybody I knew and spent the first night in Carla’s arms weeping gently and whispering and shouting about my Lisa and how unfair it was that she had been taken like that. Strangely, I felt better in the morning having been able to grieve with Carla and her eyes were equally red and puffy as mine. We obviously became very close but we didn’t indulge in any sex at all. I still took comfort in the feel of satin and suspenders and all the female clothes I wore but couldn’t bring myself to be in any way slutty or sexy. I think Carla understood and was an absolute brick for me, allowing me to let go like that.
I did manage to visit Gina and Peter and they too were really good. Through her tears Gina said that if it would help, she would gladly put me to work as a pony and I thanked her but declined. Carla left me there and I curled up with Gina and Peter joined us to share all my memories of Lisa and our life together. I don’t recall going to bed but in the morning when I woke I found us all fully dressed and intertwined on a double bed in what I later learned was Gina and Peter’s bedroom. I felt slightly better and Peter drove me back to FemsRace where Carla met me. I embraced Peter and kissed him lightly on the lips and felt him respond to me. As we broke away from each other I looked into his eyes and saw only warmth there. I think we both knew that we would probably never see each other again. My eyes pricked but I managed to stop myself from crying. I was beginning to get a grip.
Carla took me home again and my flat had been cleared of Lisa’s clothes and completely revamped and redecorated. Apparently I had Carla’s husband to thank for that. I had some wonderful memories and quite a few mementoes of her and our life together. Certainly the revamp and new décor made the flat feel brand new and it was and is my home.
When I returned to work my colleagues and boss were really genuinely pleased to see me and that helped enormously.
So that is my story. This was my route to being a successful T Girl.
FemsRace is no more, Carla tells me. It closed shortly after we were there. Perhaps she is just saying that to help me cut the ties.
I want to leave you with a mental picture. A beautiful, mature woman standing in the foreground and looking at you with a steady gaze, a slight smile on her lips, confident, her legs apart clad in stockings and shiny high heels. The swell of her breasts visible under her open jacket and her high neck cerise colour sheer blouse. Is that the hint of a matching bra you can see under the blouse? Is that a stocking top just visible under the hem of her short mini skirt? Her hand on her right hip which is thrust out to meet it, her left hand loose at her thigh. Are those hands a bit big? Look at those dark red nails, just like talons! Your attention is drawn back to her luscious lips painted dark red. Are those shoulders a bit broad? Never mind, look at those legs!
You see a confident poised woman, a MILF if you like. In the background is a man. Her boyfriend? He seems to be a shrinking violet. Why is he so far back with his hands to his face? Is he trying to hide?
My God that is one sexy lady!
So what are you waiting for boys and girls alike? Come and get me!
This story continues on from “Tim Ch 1 — Tim & Jessica are forced to work as submissive sex slaves.”. This chapter works as a stand-alone story.
Miss Christensen sat down to do her monthly reports. Jessica had proved a great success. She was pretty, liked her sex and had adapted well to the discipline, taking her punishment without complaint. Clients loved her. Miss Christensen remembered she had been a call-girl in London, a good start but still some call-girls found it hard to adapt to the beatings and the requirements of being submissive. Mr Cartwright had a soft spot for Jessica; he would be pleased that she was doing well.
Miss Christensen was less sure about Tim. He was handsome, almost pretty, and so far he had served clients well. They liked his innocent androgynous looks and waif like body. But he had resisted initially and she was unsure if he had been properly broken. She felt there was a risk that he would rebel in future. If he did Miss Christensen had a simple plan; immediate and extreme pain. Not subtle but she had to ensure he knew that he was a whore, merely a rich lady’s plaything and had a duty to obey. Miss Christensen vowed to break him, no matter what it took. She was confident that if she could train him, he would make an excellent submissive prostitute.
For the first couple of weeks she had not put Tim ‘on the system’, having decided to sell him as a ‘teenage virgin’ to selected well-heeled clients. She had her stylists go to work on him so as Tim appeared to be an eighteen year old. When a potential client was identified, he was brought into her office in a collar marked ‘virgin’ and some brief black knickers. A member of staff posed as his mother who explained that Tim wanted to work as a prostitute and she was not going to stand in his way. He was fully trained and understood the punishments he would have to endure and the sexual services he would have to provide. She only asked that as his first date, the customer would be gentle with the poor boy and make allowances for his inexperience. She ruffled the hair and patted the thigh of her seemingly nervous (and almost naked) ‘son’. Miss Christensen managed to charge a number of clients super-premium rates for taking his ‘virginity’. Tim seemed to act the enthusiastic, naïve boy extremely well and clients were overjoyed with the experience. Soon he was ‘on the system’ and earning his keep as one of the junior whores.
After Tim and Jessica had been on the island for about a month, Miss Christensen announced, at one of her routine weekly briefings, that the next ‘school’ party would be the following month. This announcement seemed to cause great excitement. They were quickly filled in on the details. The island hosted such parties four times a year. They involved all the whores dressing up as schoolboys and schoolgirls and the whole island being transformed into a school. Most of the whores were in their early twenties and made no attempt to appear younger, the attraction was the outrageously sexy uniforms and the party atmosphere. The events were hugely popular with the clients, which made them very lucrative. The demand was such that Cartwright & Palmer imported whores in from other offices, mainly London and New York, to cater for the demand.
As the date came closer Tim was required to help with the preparations. This mainly involved converting some of the dungeons into school rooms and opening up the bespoke school buildings; these housed the showers, dormitories and changing rooms.
A week before the first guests arrived everyone was issued with their uniforms. Both boys and girls were to wear white satin shirts buttoned at the wrist and neck along with a dark blue striped tie with the colour of the stripe indicating the whore’s grade. Girls wore a very short black satin pleated skirt and the boys tight black satin shorts. The only non-school item of clothing was lingerie, they were all permitted to wear their normal knickers.
Everyone was photographed for the ‘yearbook’ (available on-line or for $85 at the island’s shop). The top of the page was pretty standard; the girl or boy in their school uniform, their age, statistics, grade, orientation (about 95% said bi-sexual) and education (there were a number of degrees and even two doctorates on the staff). The bottom of the page was less conventional as it had photographs of the person naked along with the sexual services they offered.
Tim had already been photographed for his web page. Shots had been taken fully clothed, in swimwear and a couple of shots of him naked lying on a fur rug showing his delectable bottom; all quite tame. For the school photographs Cartwright & Palmer brought in their official photographer, ‘Chiara Salvadori’. Tim dressed in his school uniform and presented himself at one of the dungeons that had been transformed into a studio for a few days. Chiara was a slim beautiful woman, probably in her mid to late thirties, with her dark hair swept back in a pony tail. She certainly had a presence and a natural authority that Tim found slightly surprising in view of her slight physique.
“Tim, let’s start with you leaning against the wall … pull up your shorts I want them to look tight.” Chiara took shots from various angles of him in his uniform. “OK, shirt off … arms across your chest … smile … bend over … kneel … up you get … now take your shorts down … slowly.”
Tim was now down to his brief black knickers, “Good, let’s start with your arms across your chest … now, hands behind your back … turn around, and bend over … kneel down, hands in front of you … eyes down, look embarrassed … lay down on the bed … and pull your pants down just a little … thank you.”
“Up you get, now lower your knickers … hold them mid thigh … strip naked for me … perfect … spread your legs more … look natural … turn around, show me your bottom … on your knees.” All the time Chiara was shooting away.
Chiara handed Tim a pot of cream and told him to cover himself with it. She said it would stop his skin reflecting the bright photographic lights. Initially he rubbed some on his face then his arms, and gradually went down his body, missing his pubic area. Tim began to enjoy massaging himself, although he would have liked some privacy. He did his back and finally his bottom. Chiara warned him he had to do all his body, as any bits he missed would reflect the light. Taking the hint, Tim turned away from Chiara as he rubbed it into his penis and between his legs. Looking down he saw he had a huge erection, the cream made his skin tingle, it was a very erotic feeling. Tim gave himself a last once-over to ensure he was really complete, he was enjoying this. Chiara was enjoying taking the photographs. She knew the cream would get him very aroused, so he would loose any inhibitions he might normally have. It should make it much easier to get him posing in the nude and to agree to some pretty explicit scenes she had in mind.
Chiara took photos of Tim naked from the front, then back. She then had him coyly trying to cover himself with his knickers, bending over, pulling his buttocks apart, in ‘the position’, on his back with his legs spread and finally on all fours. Most of the poses she wanted Tim to be relaxed, but sometimes she had him erect. Tim simply obeyed, smiling depending on Chiara’s instructions. He had been under Cartwright & Palmer discipline long enough to know not to complain, anyway he was rather enjoying it.
“Now for the fun. Get on all fours … let’s start with the dildo … please insert it.” Chiara handed Tim a large black dildo and tub of lube. Tim did as he was told despite the dildo being considerably bigger than he was used to, and eventually he inserted it to Chiara’s satisfaction. Chiara photographed him on his hands and knees then lying on his back playing with the dildo. All the time Chiara was giving Tim instructions, “Come on try harder. Tim I want to see that dildo all the way up.” Tim was sweating as he tried to get the dildo into his anus, it was really huge, he would like to see Chiara do this. “Keep yourself erect … keep pumping … faster … I want a look of ecstasy … legs wider, really spreads those legs … now I want some close ups of you sucking the dildo … deeper … perfect.”
Tim knew things were getting a little heavy but was feeling hugely horny so was happy to follow Chiara’s instructions. “Susan your turn now.” A pretty naked girl walked over. Tim had never met her and it seemed they were going to do a photo shoot without being formally introduced. They started with them in an intimate embrace but quickly moved to sex, first in the missionary position, followed by doggie. Any thought of simulating it had long been forgotten. Chiara wanted it ‘hard and dirty’. She had Tim lie on his back as Susan gave him an (excellent) blow job. Finally she had Tim lick Susan’s pussy. All the time Chiara was taking photos from all angles.
“Tim almost done, we just need you to pose with on the St Andrew’s cross and a few other bits of equipment.” Chiara buckled him onto the cross, and took photographs of him from the front. She then turned him around and secured him. The restraints were tight and Tim couldn’t relax. When fully secure, Chiara picked up an old fashioned cane and hit Tim four hard strokes on the buttocks. “Tim, sorry about that, but the stripes across your arse look wonderful.” Susan returned, now dressed in PVC underwear, suspenders and boots. She posed spanking Tim over her knee, standing on him and whipping him with a riding crop. Lastly Chiara had Tim kneeling licking Susan’s boots.
Tim was tired and felt abused when he was finally released. Chiara seemed to enjoy ordering him around stark naked and intentionally humiliating him, by the end she was calling him ‘slut’. He thought she must have taken hundreds of shots; she could produce an entire pornographic book rather than ‘a couple of shots for the website’ as she claimed. Even so, Chiara told Tim she wanted more, he was to be at the ‘Kusiemski pool’ at 11am the next day for the outside shots.
Tim presented himself as ordered. Chiara got Tim to strip and massage his skin with coconut oil so it was glistening. She recorded Tim’s progress. She then took shots of him in his bikini lying down, back and front. She got him to untie the sides and took shots where Tim was covered but only just, he was meant to look very ‘available’. She took some photographs of him walking by the pool, swimming and in particular just getting out of the pool. She repeated this process with Tim wearing a tiny pair of trunks and finally naked. She took a lot of photographs of him naked; lying on his front and back on the lounger, spreading his legs and kneeling on the lounger showing off his pert bottom. Then walking by the pool, casually carrying a bikini and finally more photos of him swimming. By the end of the session Tim had quite an audience that Chiara did nothing to discourage. The next day Tim arranged to see Chiara. He was embarrassed as he felt the first session in particular was very explicit. He shuddered when he remembered some of the poses he had been in. What had he been thinking? He hoped he could persuade Chiara to junk some of the most salacious shots. This said, he knew some good photographs could lead to a great increase in the ‘dates’ he was booked for. Chiara showed Tim the selection she had chosen for his web page with some pride, but declined to remove any, despite Tim’s entreaties. ~ The first yachts started arriving on the Wednesday evening but most of the guests arrived on Thursday when management provided an efficient shuttle service from a couple of private landing stages on the mainland. All guests were met by a whore who carried their luggage and made sure they were comfortable and if they were new to the island showed them around the resort.
Tim had been booked for the initial date by a lady called Christin von Eberstein. He was told she was to be arriving at 11am on Thursday and he should present himself at the marina to greet her. As the booking had been made well in advance Tim had the opportunity to ask around to find out about this Eberstein. He was told she was a beautiful German lady. When she was in a good mood she could be quite charming when irritated she could be a complete bitch, taking great pleasure in humiliating her whore and causing them great pain. She demanded constant attention and respect.
The meet up was easy as Christin had seen Tim’s photographs. Tim was keen to make a good initial impression so immediately dropped to his knees. He then carried Christin’s luggage to the hotel complex.
Whilst Tim unpacked Christin’s things, Christin went out on the balcony to admire the view. Although nothing had been said, Tim could feel the massive sexual tension. When she thought Tim was not looking Christin rubbed herself producing a rather attractive soft pink flush.
“Tim, the position.”
Tim stripped naked and got down on his knees, it was important to get off to a good start especially for these longer dates. After all he had been warned not to take any liberties.
“Tim, I have been to the island on several occasions, but this is the first time I have managed to make one of your Schoolboy parties. We have a school room booked for 3pm, before then I want you to take me around and show me the ‘sights’.”
Tim started his tour with the games rooms. There was a girls’ basketball game being played. The girls wore very revealing outfits. Tim explained that their outfits all had their personal number on them in the same way that girls’ uniform skirts and boys’ shorts did. So if a client liked the look of one of the players they could be booked. Christin was interested and seemed to have eyes for a tall Brazilian playing in defence, her lithe frame hid a formidable physique.
Tim then showed Christin the gym. As well as the normal weights machines and treadmills there was an area where they saw a number of female whores practicing their floor exercises. It always amazed Tim seeing how flexible some of these girls were. He saw one girl doing a slow perfect splits. All the girls had their numbers embroidered on their leotards. Tim showed Christin a keypad so that observers could summon any of the whores they liked the look of. Keying in the number 20 Christin sent for a girl called Nadia. Nadia seeing her number immediately stopped her exercise and rushed over, falling on her knees before Christin. Nadia was a professional athlete before she came to Cartwright & Palmer, representing Russia at the Beijing Olympic Games. She had continued with her punishing exercise schedule and Tim thought she had the most perfect body he had ever seen.
“Yes Miss, what can I do for you?”
“Let me see you in ‘the position’”
Nadia stripped off her leotard and got back to her knees. Christin then asked her to stand up and turn around. Nadia did as asked, moving with her normal air of serenity. After turning around she did a slow back flip, showing her grace and athleticism, after which she returned to ‘the position’. Christin evidently liked what she saw as she left determined to book the girl.
Tim escorted Christin to one of the resort’s restaurants. As they waited to be seated Christin said, “Tim, lick my shoes.” Tim got to his knees and started licking. Christin liked to do this sort of thing for many reasons; the first was the simple pleasure of humiliating Tim in public, then of course it showed Tim that she might treat him as an equal but that he should never forget his real status and lastly she could see how quickly the whore got to their knees. If there was some resistance or hesitation Christin knew that she the whore was probably second rate and she would have to start any session with severe corporal punishment to get the obedience she wanted. Tim passed the test.
When they were seated, Christin wanted to know about life on the island and how Tim found being a prostitute. She had looked at his web page and asked about some of the sexual services he offered, many of which were totally new to her. Tim gave Christin a ‘sugar coated’ version of life. To be truthful he didn’t really know how he felt about his new profession, but he thought the situation called for light banter and a few amusing ‘war stories’ rather than an in depth confession.
As they were drinking their coffee Christin handed Tim a pair of knickers and told him to put them on. Tim went to the back of the restaurant and changed, he struggled out of his shorts and then proceeded to put on the knickers. They were red with some subtle black lace trim. The difficulty was they were made of satin, lovely and smooth but with very little ‘give’, eventually he got himself into them and returned. Christin felt that these knickers were the best mementos of a successful date. She just loved wearing them later, remembering the fun she had had. She was wearing some pink ones that had been worn by a poor girl in London called Marie-Louise. Helen had told her that the girl liked it ‘rough’ and ‘really enjoys pain’. Christin had spent a wonderful afternoon humiliating her. Christin remembered whipping her and forcing her to put ever larger dildos into her pussy and bottom. The girl could barely stand by the end of it. Marie-Louise must have been one of the most depraved tarts on the firm’s books, she seemed to have no limits. Christin smiled as she remembered Marie-Louise dressed just in the knickers drinking from a dog bowl in the bar and how she ordered the poor exhausted slut to go to a neighbouring table and offer herself free of charge. The last Christin saw of the girl was her being led away stark naked by four men, doubtless to be rogered senseless. Oh how she enjoyed wearing these knickers and hoped the red ones would bring back similar memories.
After lunch, Christin sent Tim off to check the school room’s number. She leant back and stared at his bottom, so beautiful in those tight satin shorts. She mused that there were a number of other agencies that could provide boys and girls as attractive as Cartwright & Palmer, but it was a submissiveness and willingness to please that really made these whores stand out. She knew that Tim would comply with any of her orders, no matter what they were, no ifs or buts he would simply do it. She could see that sometimes a whore might be deeply humiliated or in great pain but a Cartwright & Palmer prostitute never refused. Christin loved this obedience and was prepared to pay handsomely for it. The island seemed even better than Regensburg or London.
As she cradled her wine she thought of what she was going to do to Tim. She had read the sexual services he offered and as ever was amazed and the number and variety. Over the past couple of weeks she had filled every waking hour with one erotic idea after the next, the list was endless. Now she had seen that Brazilian and that minx Nadia. What a wonderful thought, these two doing anything she wanted. Which should she take? A lovely dilemma.
After lunch they went to Cartwright & Palmer’s shop. This huge room was in the basement of the hotel and about two thirds of the area was given over to various sexual aides, the rest to DVDs and magazines. Christin bought a couple of DVDs of Tim being tortured and humiliated by two of the in-house dominatrixes. She then looked through the clothes and chose a PVC corset and a tight wet-look skirt for herself. She bought Tim the sweetest little satin sailors outfit and a brief gold spandex bikini. She longed to see his embarrassment as she forced him to wear it by the pool.
They walked to the whips section, the choice was incredible. “OK, Tim bend over I want to test a few of these.” Tim bent over as he was told.
“Oh come on Tim, shorts down.” Tim wriggled out of his shorts and then acknowledging the inevitable took down his knickers. Christin practiced using a paddle then an old fashioned cane. Tim winced as the cane struck his buttocks, looking around he saw he had quite an audience. Eventually Christin decided on a cat and a cane.
Tim, relieved, reached for his knickers but Christin had other ideas. “No you don’t Tim. I will need your bottom again before we are through.” Tim saw one of the shop assistants coming over, he was worried that he was about to be bollocked as although whores were encouraged to dress provocatively they were not meant to be naked in public. It was always the whore rather than the client who was told off. The shirt’s tails only just about covered his modesty. In the end the assistant only wanted to make a few ingratiating comments to Christin.
They came to the dildo section, a selection were on display in sterilising solution. Christin pickled up a huge vibrator. “Tim, spread your legs.” Tim did as he was told he could not believe Christin was going to fuck him in public. He felt the slight sting as the sterilising liquid was wiped along his arse. He felt more pressure as Christin pushed. Tim tried to relax, but he knew this was going to be difficult. Christin eventually inserted the dildo and gave Tim a few hard pumps. The performance had again attracted an audience.
“So Tim what do you think?”
In truth Tim didn’t have much of an opinion, one dildo was pretty much like any other to him but he wanted his humiliation to stop, “It’s great Miss. I think you ought to buy it.” Christin did not fall for this and tried two more dildos in Tim before deciding on a large red gel version as it would match Tim’s knickers (when of course she allowed him to put them back on).
When it came to gags Christin asked for the assistant’s help. The shop assistant asked Christin, “Well Miss, do you want the gag for decorative purposes, to keep your whore silent or to cause maximum discomfort?”
“Well, I hadn’t really thought. I suppose to keep him silent.”
The assistant showed Christin various models explaining that nothing very new had come onto the market recently. She then pointed to a ball gag with a silver rubber ball which she said was quite fashionable.
The assistant picked out a black gag in the shape of a large penis, “This is great for punishing slaves, it also improves a slave’s ability to give blow jobs as they get used to taking the penis all the way down their throat.” Christin picked up the gag, trying to hide her surprise at the size of the penis, could Tim really take this down his throat? There was only one way to find out. She gingerly eased it into Tim’s mouth and eventually got it all the way down; the poor boy looked in great discomfort. Christin buckled the gag securely in place.
The assistant recommended the matching butt plug, “It’s big but your slut looks as if he can take it. It’s a really nice set and being penetrated by two cocks at once can really humiliate a boy.” Christin liked the idea and told the assistant to try it out on Tim. Tim was prepared and now used to being fucked but the plug was huge. He stripped off his shirt and tie and bent over, trying to relax. The assistant lubed the plug and Tim’s rectum with practiced skill, but they both knew it was not going to be easy to insert something this large. The size of the plug and Tim’s efforts to take it increased the size of the crowd. He strained, pulling his buttocks as wide as he could, gyrating his hips to ease the entry of the monster. The assistant was putting huge pressure into forcing the plug in and out, trying to push it deeper with every stroke. It was hard work, but she could see it was worse for Tim, who was sweating profusely and in obvious distress, made worse by the gag. When eventually it was in place Tim was hugely relieved and almost insensible to an enthusiastic round of applause. On the end of the plug was a cute little bunny’s tail, it made Tim’s adorable arse look so sweet. Christin loved the set and bought it without any hesitation.
Christin made Tim keep the plug and gag in for the rest of her visit to the shop. She gazed at Tim walking naked around the shop; she almost felt sorry for inflicting such pain and humiliation on the poor boy, but watching him turned her on terribly. She just loved torturing him, but seeing so many people staring at his nudity eventually she allowed her ‘little bunny’ to put some backless knickers on. His tail was still on display and his arse look beautiful.
Tim had noted that it had become increasingly fashionable for guests to keep their whores on a chain attached to a collar. Christin had also noticed this and her eyes lit up when she saw the collars on display. She had Tim model dozens before she chose a plain stainless steel collar. She decided that she would have, “The property of Christin von Eberstein” engraved on it.
There was some embarrassment when Christin came to pay for her purchases as she could not remember the size of the butt plug. She had her ‘little bunny’ bend over, spread his legs and his clasp his buttocks so the shop assistant could read the bar code on the end of the plug. When this was sorted Christin allowed Tim to put his uniform back on and remove the gag. They then left casually chatting.
Christin sent Tim to one of the school rooms whilst she returned to her room to change. Tim took the opportunity to remove the butt plug, he felt a huge sense of relief. Christin returned dressed as a ‘teacher’, this involved a white satin shirt and a latex micro skirt. She looked fantastic, the get up showing off her figure and particularly her long legs to their best advantage. Tim thought back and admitted he could not remember that number of his teachers wearing such a skirt but it was not his place to comment.
Christin sat down in one of the easy chairs and looked at Tim with a severe expression, “Come on my little bunny, strip down to your collar and panties.”
Tim did as he was told, slowly removing his tie, shirt and shorts. Christin said nothing, just staring at him. Tim hated people watching him undress and Christin’s insistence that he keep his knickers on was almost worse that stripping naked. She had clearly chosen them to humiliate him, they were very brief, being made of red satin with edgings of black lace.
“Bend over the desk.” Tim did so, tensing his buttocks and legs to show himself off to the best advantage. Christin approached and stroked the tight satin, her hand then wandered between Tim’s legs massaging his cock. She did this with a certain languor.
Christin loved seeing Tim bent over like this, the red satin of his panties stretched taught against his buttocks, it gave her such a sense of power. The feeling almost sent an electric shock to her pussy; every step seemed add to her desire as her pussy rubbed against the latex of her skirt. She was feeling so incredibly horny.
Christin picked up the riding crop and started to whip Tim, softly to begin with but with gradually increasing force. Although Tim tried to stay silent, he let out involuntary yelps whenever Christin struck a hard blow.
“Bunny, take down your panties, I want to see my handiwork.” Tim slipped down his knickers revealing his buttocks criss-crossed with vivid red stripes. Christin continued to beat the now naked Tim. His cries of pain were so erotic. But despite the punishment he stayed leaning over the desk, just for her entertainment. Christin admired her boy, he was so damned beautiful and he was hers, she had to have him. Christin motioned Tim to her bed and got him to lie down.
“Now let’s have some fun.”
Christin struggled out of her latex skirt and then whipped off her panties. She tied her shirt under her tits and stood in front of Tim to let him admire her. Admire her Tim certainly did, she looked magnificent just dressed in her stockings and shirt, her midriff and partially shaved pussy on show. She had a great body and knew it. Tim was rapidly becoming excited.
Christin crawled onto the bed. Tim knew a good prostitute always responded to their client’s mood, after such a whipping Tim was expecting Christin to want some pretty rough sex. But he was surprised, Christin held him firmly but then kissed him incredibly gently, initially her lips barely brushed his. Tim therefore was careful when he penetrated her, so as to be as gentle as he could. His thrusts were slow and careful. Christin responded, gradually upping the tempo, increasing the pace. Soon he was fucking her with an animal passion. As she reached climax she screamed with pleasure. She had fucked her slave and it had been wonderful.
Tim felt Christin’s head resting on his shoulder as she dozed in a blissful sleep. When she awoke the intoxicating smell of cum aroused her anew. She gave a Tim a gentle blow job, not really to excite him more to taste his cum. She then released him and had him take her in the doggy position. This time Alex clutched her tightly in his arms as they both dozed. Eventually it came time for Tim to leave, he dressed in his uniform and gave the still sleepy Christin a gentle kiss goodbye.
As he left, he kicked himself remembering the Escorts’ rule number one, never fall in love with your client. He knew this but he did so hope that Christin would choose him again. ~
As Tim returned, tired, to his room he was called by one of the ‘teachers’. These were customers who had paid for the privilege of ‘disciplining’ any boy or girl they desired.
“You, come here.”
Tim approached as he was bidden, “Yes, Miss.”
Tim knew the score, he squeezed out of his shorts and let them fall to the ground. He then did the same to his knickers and bent over, legs straight, hands on his knees and awaited the inevitable. He felt the breeze on his exposed cock and buttocks. His nakedness was attracting an audience.
The ‘teacher’ smiled, gently raised Tim’s shirt and proceeded to whip his bare bottom with a riding crop six times. After his punishment Tim pulled up his knickers and shorts and said “Thank you, Miss.” He knew one session was not too bad but he hoped not to get caught too often.
Jessica was thinking the same thing. She had been caught four times in the last half hour and her bottom was now a very rosy shade of red. It was painful even for a reasonably experienced submissive such as herself. She couldn’t keep on getting spanked, the best way of avoiding such regular punishment was to get a half or whole-day date. A date may involve some pain but this was likely to involve one session and be relatively short and sharp.
Management always ensured that there were far more whores on duty than there were guests, this ensured that there was always great competition between the whores. Jessica wondered about how best to get the date she desired. She knew she could always sell herself at the 6 o’clock auction, the difficulty there was that if enough customers did not turn up she might find herself going for 99c. She thought about sitting on the low wall just outside the entrance to the dormitories. When she got there she saw that six girls were already sitting on the wall including one painfully gorgeous grade one. She thought of joining them, but worried the area might be on one of the teachers’ beats. Jessica therefore decided to head for the communal showers. The idea was that girls and boys showered there after playing games, but Jessica knew no one would mind her having an extra shower. She stripped and put on her collar so clients would know she was available and her grade.
Jessica stood under the powerful cascade of water luxuriating in the massage this gave her. The shower seemed to reduce the pain of the spankings and she quickly forgot the reason for originally coming there and started to enjoy herself. She was brought back to the present when she feel a hand gently to massaging her bottom. She began to turn, she knew the next few seconds were important. She wanted to ‘land this date’, in particular she hoped it was not some opportunistic whore or a time waster client. She smiled her most alluring smile and saw her admirer was certainly a client, he looked the CEO type, averagely handsome but well put together with obvious charisma.
Jessica pressed her body lightly against his. He did not pull away so she pressed her pussy against his thigh, knowing he would feel her warmth. He did not say anything, he merely took her hand and steered her out of the shower. She dried herself, put on her shirt and tie and without knickers or skirt started on her hair and make up. When she saw he was ready she wandered over and finished dressing.
“Hi, I’m Simon. Would you be able to keep me company for the next twenty four hours?”
Jessica’s heart jumped, this is exactly what she was hoping for, “Yes sir, that would give me great pleasure. My name is Jessica.”
“OK, Jessica take your knickers off. You won’t need them for a while.”
Jessica quickly took off her panties and handed them over. It was odd, she was so used to being naked in front of customers but walking around without knickers still felt very unnatural and rather decedent. More so because she was so perfectly shaved, she felt cold. As her skirt was so short she suspected her nakedness was not a total secret to those she and Simon passed on the way to the hotel complex. Perhaps Simon was thinking along the same lines and to ensure there was no uncertainty he got Jessica to bend over to pick things up at regular intervals exposing her ever so bare bottom.
On entering his room, Simon immediately told Jessica to open her mouth and pushed her panties in. He sat down and told Jessica to lie on his lap. Simon started by raising her skirt and stroking her beautiful behind, but before long began to spank her. The strokes were getting quicker and harder as Simon got increasingly excited. Being spanked was an inevitable part of being a school girl, but Jessica was in real pain. She screamed but with panties firmly wedged in her mouth only the quietest mumble could be heard, not that Simon was interested he was in “the zone”.
Eventually Simon seemed to get tired and he first slowed then stopped. He then slipped his hand between her legs and started to stroke her pussy. Jessica’s body was in overload, first pain now pleasure. She squirmed as his rubbed her clitoris. He then forced his fingers into her pussy entering her with increasing force. Jessica gasped, her pain forgotten, she was now wild with desire.
“OK, Jessica, put on these wrist and ankle cuffs and sit on the bed.”
Jessica did as she was told, feeling renewed pain as she sat down. She pulled up her skirt, spread her legs as far as she could and awaited Simon’s pleasure. Simon clipped her wrists to a hook above her head and her ankles to the bed board about three feet apart. Jessica was now firmly secured, legs spread and pussy totally exposed and defenceless. Simon surveyed his handiwork then stripped and quickly entered her with the barest minimum of preparation. The fucking was brutal, this was basic and animal sex, no love or gentleness Simon thrust with ever increasing force. Eventually he came with a shout of ecstasy. After his climax Simon slept, leaving Jessica secured, cum all over her.
Jessica was still in her, now ragged and stained, uniform; her was makeup smudged with streaks of sweat, she looked a sight. On waking Simon told Jessica to get some clean stockings, suspenders and panties as they were going to dinner. Simon dressed in an immaculate dinner jacket and waited as Jessica did her make up, she put on her underwear and entered the main bedroom. She hoped Simon would let her wear her evening dress or even her uniform, but she was disappointed.
“Good, Jessica you look wonderful. Let’s go.”
Simon escorted her down to the lifts. Jessica tried to look relaxed as she walked down the corridor. She was proud of her body, in particular her pert tits, but still felt very naked seeing couples in their elegant evening dress. When they arrived at the lifts they met a lady who seemed fascinated by Jessica’s breasts and with Simon’s permission stroked and squeezed Jessica’s nipples. She then asked Simon about Jessica’s sexual prowess as if Jessica wasn’t there. Jessica was very conscious that the livid red stripes on her bottom were very visible; the brief satin panties giving almost no protection. Simon made her bend over and take down her knickers so the lady could examine her bottom in intimate detail.
On arriving on the third floor Jessica tried to quickly pull up her panties. The lady went to the right and Simon guided Jessica to the left. They headed for the ‘Graziani’s’. As they entered Jessica saw a discreet sign ‘All patrons are respectfully asked to wear knickers at all times’, as Jessica looked around she saw this was about all many of her fellow whores had on.
They were steered to a table in the centre of the room. After Simon’s rather brutal treatment of her so far, Jessica was surprised to find he was a delightful dinner companion. She very much enjoyed his light self depreciating wit and laughed, totally forgetting that she was topless and had an aching bottom. After the second cognac Simon said they had better be going.
One of the main attractions of the weekend was the dormitory block. This was a specifically designed building that consisted of four dormitories, one all male, one all female and two mixed, each having about thirty beds. Every dormitory had a wash block attached, in the centre of which was a block of basins, on the right shower cubicles and on the left a communal shower area. Whores were, of course, obliged to wash in the latter.
Simon had booked two beds for the night. Jessica found her single bed and stripped, she then went to the shower and washed carefully making sure Simon had a good view. Returning to her bed she dressed in the standard night shirt. This was pale pink satin for girls and pale blue for boys. It had was short coming down to mid thigh, had long sleeves buttoned at the wrists and was buttoned at the neck with a small delicate collar. Looking in the mirror she knew she looked terribly innocent and vulnerable. Even she could admit that the innocent bit was not a real reflection on her moral character. When she had dressed she joined her fellow whores doing the sort of thing school girls did before bed. She shaved her bikini area, lubed herself then read a romantic novel.
The lights flashed on and off indicating ‘lights out’ would be in five minutes. Jessica looked at her bedside table, with the normal schoolgirl accoutrements; alarm clock, teddy bear and … a dozen condoms, lube and a twelve inch gel vibrator.
Jessica’s mind wandered and she thought back to her time in Diston, how a week after her eighteenth birthday she approached the local brothel asking for a job. Mrs P took her on a probationary basis telling her she should, “Be attentive, willing, available and fuck like a bunny.” When the lights went out Jessica got out of bed, she pulled her nightshirt up to her neck and spread her legs. Jessica then gave her clit a good rub. She felt ready. She thought Mrs P would concede she looked pretty ‘willing and available’.
Simon told her to kneel on all fours on her bed. Jessica did as she was told, spreading her legs as far as she could. This time Simon was more gentle as he took her anally. After Simon had climaxed, he dismissed Jessica. As she got into her bed she felt tired, she felt she had well and truly earned her money that day and had a very sore bottom to prove it. There were still a number of couples hard at their stuff, a tired Jessica went to sleep with her teddy bear to the cries of ecstasy as her colleagues worked into the night.
Jessica woke the next morning to her neighbour’s sighing. Sex at seven am! Jessica got up and got a cup of coffee for Simon. She sat on his bed as he drank it, offering herself to him. Simon thanked her but explained he had to leave on the first flight so declined.
Jessica went back to her room. She felt she could relax for a couple hours and then try to get another date before lunch.
When Tim got back to his room he immediately stripped off, stood in front of his full length mirror and looked at the damage. Christin was a wonderful person but she had given him, quite a beating. He was proud of his body, his bottom was a rosy shade of red and hurt like hell, but there was no blood. All whores hoped only to have one beating a day, but Tim had endured two, three even four without permanent damage. He rubbed some pain relief cream into the worst affected parts and looked to see how long he had until his next booking; three hours, could be worse. Tim grabbed his book and lay down on his balcony, time for some real relaxation whilst his body recovered.
After a light lunch, Tim went to Restaurant Condé situated on the east coast of the island. He had been booked for the afternoon’s game of ‘La Chasse’. When he arrived he was issued with his kit; light Wedgewood blue latex shorts and top. The shorts were short and tight; the top was short sleeved and cropped so his midriff was exposed. The outfit had been modelled on female athletes’ running kit. The girls wore something similar in pale pink.
The changing room had glass walls to allow clients to watch the whores as they changed. When Tim realised a couple of ladies were watching him, he ensured he was naked for as long as possible. This was a great way of attracting a client. Tim slowly stripped out of his uniform before picking up his latex outfit. He didn’t really need to try extend the process as it took an age to get the latex shorts and top on. The things were so tight, but Tim knew it had been worth the effort when he looked at himself in the mirror. He shouldn’t have any difficulty in getting a date dressed like this.
When he had finished he joined the rest of the whores and the clients in the restaurant. The crowd went quiet as Miss Christensen entered the room, “Can I please have your attention. I realise most of you have played ‘La Chasse’ before, but let me go over the rules for any newcomers. In simple terms it is a hunt. Clients, or ‘hunters’, aim to shoot as many whores as they can. Whores obliviously must try to avoid being caught. The game goes on for ninety minutes. Whores can go anywhere in the Condé gardens. If shot, whores must return here and wait for their new owner. Hunters please try not to shoot whores in the face or genitals. If a hunter manages to shoot more than one whore they can sell any they don’t want at the drinks party that we will be having here after then end of the hunt. If a whore avoids being shot they are free to sell themselves at the party. Lastly remember than one of the whores has a Cartwright & Palmer silver sovereign in their knickers. OK, whores off you go you have a five minute start.”
Tim headed for the exit, he thought there were probably about twenty whores. He wished he had thought about tactics in advance. It seemed one could either rely on speed and agility and run from the hunters or one could hide. The Condé gardens were lovely, Tim thought they must be two or three acres set out like an English park with a manicured lawn, decorative lake and a couple of small woods and they provided a fair amount of cover.
Tim always favoured the counter-intuitive so when he saw his fellow whores running down the hill trying to put as much distance between themselves and the hunters as they could, he decided to do the opposite and rushed to find a hiding place close to the restaurant. He quickly found some long grass and laid down. He hoped to have a boring ninety minutes as he could not see if hunters were approaching without giving himself away. After twenty minutes Tim was dozing, all he could hear were a few isolated screams of excitement and sometimes pain. No hunter had been close.
Eventually Tim heard the footsteps of an approaching hunter. He wondered if he could risk raising his head to see if the hunter was coming in his direction and if they were, making a break for it before it was too late. Tim knew he had a decent turn of speed but a paintball travelled at about 300 mph, rather more than Tim’s best. As he was close to the fence he could only run left or right making him an easy target. There was nothing to be done but hope and wait. Tim tried to flatten himself in the unresponsive earth, he held his breath and prayed.
But it was no good, as Tim looked up he saw a hunter staring down. Tim was about to surrender when he felt intense pain in his buttocks and back as the bastard shot him a dozen or so times.
“OK, up you get you whore. Shorts down.” Tim got to his feet and automatically dropped his shorts, not that easy as they were latex but he managed it. The hunter felt Tim’s penis and looked inside his shorts. Tim realised he was looking for the sovereign, but without success.
“Right, go back to the restaurant. Tell them you were shot by Olivier, number eight.” With that the guy ran off clearly determined to add to his haul. As Tim wandered back he felt the yellow paint ooze down his shorts and thighs.
Tim was gratified to find that he was not the first to have been shot. Miss Christensen met him, and after asking him how he enjoyed the game told him to shower and put his uniform back on. He was given a tag to wear that had Olivier’s name and he assumed his telephone number stamped on it.
The siren went off, indicating the end of the game. The hunters and the whores who had not been caught gradually returned. When Olivier entered the room, Tim and Angel, who he had also shot (this time aiming for her pussy), approached and knelt before him.
Olivier read their names from the tags, “Tim, you are the first boy I have shot. What can you do for me?”
“Master, everyone should try a boy. I am very willing and enthusiastic. I will give you a great time I promise. I give a great blow job.”
Olivier smiled and started to stroke the front of Tim’s satin shorts. Tim quickly became erect, “Thank you Tim. You make it sound very inviting. As you say I really should sample a willing boy. But I am afraid Angel can do things no boy can rival. So Angel, you will be my guest for the rest of my stay. Tim, I propose to sell you.”
Tim felt strangely humiliated by this rejection, but quickly got to his feet and scurried away. Whores who were for sale were told to help serving the drinks. The idea being to give as many of the clients a chance to see them (and potentially make Olivier an offer) as possible. Tim put on an apron and got to work. He had no idea if anyone was bidding for his services as lots of clients seemed to be on the phone. Tim suspected the hard bargaining was not for cash per se, but it allowed the sellers to play the pimp, an erotic and unfamiliar experience for most, if not all, of them. Tim looked with envy at those whores who had avoided being shot. They looked so damned sexy in their tight latex shorts and cropped tops, they would have little difficulty in selling themselves again. Tim looked round and saw Claudia laughing with a potential client, she was struggling out of her top and shaking her beautiful breasts, who could resist that?
After Tim had been serving for about half an hour, Olivier called him over. “Tim, come here. I have sold you to Jinx.”
Tim looked at his new Mistress. A well proportioned lady in her mid forties with blond hair in a pony tail. She was wearing a short black latex skirt and a white roll neck that showed of her breasts to good advantage. She was clearly making some efforts to look younger with some success. She was toying with a riding crop, gently tapping her thigh. Tim wondered what she would want from him. “Hello, Miss. How can I serve you?”
Jinx smiled wickedly, “You will find out, my boy.”
When they got back to Jinx’s room she immediately turned to Tim and said, “The position, now.”
Tim stripped naked, put on his slave collar and knelt on the floor. He was worried about the harsh tone of his Mistress’s voice.
“Tim, I am going through a very nasty divorce from a very nasty man. The thought of having a handsome boy willing to comply with my every whim is simply bliss. Astrid showed me the list of your sexual services, but said I could do pretty well anything I wanted with you. You seem to be a slut even by this place’s standards. She said whipping and humiliating a young slave was amazingly cathartic and she recommended it to any lady in my position.”
Jinx had read the literature and looked at the photos on the website but she still could not really believe she had Tim kneeling naked in front of her. She had expected a whore to be loud and coarse; some ‘Good Time Charlie’ forever laughing and making crude jokes. Tim was the opposite, he appeared shy and reserved, being embarrassed that someone was seeing him naked. She thought of Astrid’s advice, “Jinx, we have the most beautiful, best trained and disciplined escorts on the planet. Never since the age of the Caesars have such willing and submissive slaves been available. They’ll satisfy your every desire, be creative, enjoy yourself.” Jinx wondered how Tim had come to be in the job. Was he really a slave? Bought and sold, providing sexual services for his owner?
Jinx ordered Tim to stand. She walked around him admiring his pert buttocks, she then took his balls. They felt so perfectly smooth. She had asked Astrid about this, and knew that all the boys had to apply some concentrated Imac type cream on a daily basis. Astrid said it harked back to ancient Greece when all prostitutes had to be shaved.
Jinx told Tim to bend over the table and prepare himself for a caning. Tim bent over tensing his legs and buttocks to present himself to the best advantage. Jinx hit him in the centre of his bottom, hard but not excessively so. Tim squealed. Jinx struck him again slightly above the first stroke. She then followed this with a regular strikes up and down his buttocks. The strokes had a gradually cumulative effect. Tim bit his lips trying to stop himself crying out. Every so often Jinx would strike him particularly hard or in a very sensitive area and Tim squealed with pain. Tim did not know it but this gave Jinx real pleasure and she started aiming for the reddest portion of his now very rosy backside. Jinx then struck him on his thighs, initially this seemed a blessed relief but after a dozen strokes his thighs were agony. As Jinx continued her beating she became more and more aroused. She loved Tim’s muffled cries and his tears as they fell on the table.
Jinx knew she could torture Tim all day but had other plans for the boy. She told him to stand and handcuffed him. She caressed the inside of Tim’s thighs gently touching him with her forefinger, so lightly there was almost no contact. She felt his balls and penis with the same incredibly light touch, only allowing the tips of her fingers to brush against him. She then started to massage his balls. Tim rapidly became erect. Jinx had always been submissive in the bedroom and had long wanted to reverse her role, she had long fantasised about raping a boy. Now she had a chance. She wasn’t sure if you could rape a slave but she wasn’t worried. Jinx pushed Tim back until he fell onto the bed. She knelt over him and manoeuvred his penis into her pussy. Jinx slowly lowered herself so as to take the full length of his cock. Tim was now very hard and Jinx was similarly excited. She rose slowly and then plunged down trying to get Tim even deeper inside her. Jinx gradually increased the pace fucking Tim with greater and greater speed and ardour. The poor boy was nothing but an erect penis to her. She rammed her body down on his with a passion that bordered on violence. It was fantastic, wonderful. She shouted with pleasure as she neared climax. She had never cum with anything like this intensity. He was her first fucktoy; this is what men were made for.
Even after she had cum her pussy was on fire. After what seemed like only a few minutes she was busy getting Tim erect again. She then mounted him and fucked him again. This second time was almost as good. But this time there was to be no quick recover, she was spent. It was a blissfully satisfied Jinx who pulled the satin sheets over Tim and herself and went to sleep almost immediately.
Jinx slept soundly having blissful dreams of taking Tim against his will in ever more extreme situations. Tim’s night was less comfortable, as the handcuffs dug into his wrists. They both woke as one of the off-duty whores knocked on the door and served breakfast. Tim recognised her as Olivia, she was wearing a maids outfit with a microscopic skirt, evidently hoping for an early date.
Jinx luxuriated in the huge bed, still terribly turned-on. She picked at the croissants and sipped her coffee, taking pleasure in feeding her captive. After their breakfast Jinx positioned Tim in the middle of the bed and fucked him, again. She knew she would never tire of raping Tim. It was divine. The power, the ability to humiliate the poor boy. He really was her toy. He looked so vulnerable, he was so vulnerable! Jinx could not bear to release Tim and left him handcuffed on the bed as she showered.
After Jinx had finished she freed Tim and told him to shower (with the door open), shave and do his hair. When he finished he knelt before her. Jinx then replaced the handcuffs and put a heavy metal collar around his neck, this was attached to a chain which in turn was bolted to the bed. Jinx said she needed some air and told Tim to kneel until her return.
Jinx spent a relaxing few hours at the Kusiemski pool and just before lunch returned. This time she dispensed with the formalities and simply pushed Tim onto the bed and raped him again. When Jinx was fully satisfied, she released Tim and told him to dress. She lay on the bed naked as she watched as Tim got dressed in a clean uniform. Tim winced as he put on his knickers and tight shorts, feeling the evidence of Jinx’s beating the previous night. Once he was back in uniform Jinx gave him a huge hug and said she looked forward to taking him regularly from now on.
Jinx watched as Tim left, marvelling at his pert bottom in his satin shorts. She still felt a huge sexual buzz, but she knew the real pleasure was psychological; she had beaten and raped a man. She felt great, her power over Tim had been so liberating. Her husband would have a much tougher fight from now on.
Jessica was sunbathing when she got a call summoning her to Miss Christensen’s office. She curtseyed as she entered the room and was about to get to her knees when she saw Miss Christensen was talking to two ladies, both pretty, one in her mid-forties the other in late teens or early twenties. The resemblance was striking and Jessica immediately assumed they were mother and daughter. Miss Christensen motioned Jessica to an empty chair.
“Jessica, thank you for coming. I have a little job for you.”
The older lady interrupted, “Astrid is one of my oldest friends, we worked together when we were younger and for old times sake she has offered to give me, or really my daughter, Holly, a helping hand. As you see Holly is extremely attractive, the trouble is she is complete idiot, so her career prospects are not all they might be. We have narrowed her future down to either marrying a rich chap who doesn’t over value intelligent conversation, being a model or being a whore. She has already done a bit of modelling and things are going quite well; the trouble is that it is a very tough business, so I thought she should find out how she likes escorting. I loved it, but everyone is different.”
“So Jessica can you look after Holly for the next day or so. I will organise your dates and don’t worry I will ensure you are alright financially.”
Jessica consented, “Of course, I would be more than happy to show Holly the ropes.”
The Holly’s mother turned to her daughter, “You have a day under Jessica’s wing as ‘work experience’. Your clients will be real punters so obey everything Jessica tells you. But have fun, I will see you for lunch tomorrow.”
Holly followed Jessica from the room. “Your mother seemed a bit harsh.”
“Oh she is only being realistic. There is no way I could spend my life behind a desk. As she says I am none too bright and have the concentration span of a goldfish with a low IQ. It genuinely is modelling or whoring. Listening to their conversation I am pretty sure Astrid and my mother met when they were both ‘on the game’.”
“OK, as long as you are doing this of your own free will. First, we had better get you kitted out.”
Jessica took Holly to the ‘Wardrobe’ suite. “Right go and choose yourself some kit. You will need underwear, a white shirt and a black skirt like I am wearing. Remember we are meant to be ‘schoolgirls’. When you have found things that fit, change and come and see me.”
Jessica was sure Holly was ignorant over many things but suspected she knew her way around a clothes store. She picked out a grade six’s tie and gossiped to Mrs Nasi, the Wardrobe manager.
After about half an hour, Holly came back in her uniform. She looked great. Jessica noticed that Holly had chosen the very shortest of skirts on offer. Daring, but Jessica had to admit it showed off her long legs to a T. The shirt seemed to be the right size i.e. rather too small so Holly’s tits looked as if they were straining to get out. Jessica lifted Holly’s skirt and saw Holly had gone for some lacy black knickers, suspenders and stockings.
“Holly you look very sexy indeed. You need two skirts, two shirts and half a dozen sets off of lingerie. You should also pick up a couple of pairs of bikini bottoms.”
“Six pairs, I am only here for a day.”
“Jessica, you are now a ‘working girl’ and these are your work clothes.”
Mrs Nasi folded the clothes and bagged them. Holly was about to pick up the bag when Mrs Nasi gave her a large tub of gel and a two dozen condoms, this time Holly did not ask for an explanation.
Jessica hoped she would have an hour to explain the basics to Holly before Miss Christensen ordered them on their first date. “Now Holly tell be about yourself. First basic question, are you prepared to sleep with a man you find unattractive?”
“Jessica, I may be new to this but I am not that naive. I came here to work as a prostitute, of course I can deal with that.”
“Good, have you any experience of anal or lesbian sex.”
“I have messed around with girls in the dormitory but nothing serious. I have never done anal, but I am keen to try. In fact I am rather looking forward to it.”
“OK, what about pain, have you ever been whipped?”
“No, mum warned me that S&M was this place’s selling point and the reason you are paid so much. I am happy to try, but can we have a code word if the pain gets too much?”
“Holly, I want you to do a lot more than try, but yes we can have a ‘safe word’. I’ll ensure no one hurts you too badly.”
“The most important thing to remember when whoring is that you are trying to give your client a good time, that means being enthusiastic no matter how tired or sore you are. It also means lots of kissing, realistic moans of pleasure and passionate sex. Let’s start with some practical advice.”
Jessica stripped off and told Holly to do the same. She started the demonstration with an explanation of how to put a condom on a client then went on to how to ‘lube up’, how to give a blow job, kissing techniques and how to prepare yourself if the client wants virginal or anal sex. She then explained the basics of S&M and how a client could hurt and humiliate her.
Holly was visibly shocked at some of the advice, but to give her her due she didn’t try to pull out or say she would refuse to do anything. Jessica was sure she had dispelled some of Holly’s romantic notions but was at pains to say how much fun it could be as well. She explained that there were days and clients where she returned to her room on ‘cloud 9′ amazed that she could be so highly paid for having so much fun.