Challenge 1: The Pleasure of Prudence

August 29^th, 1997

You can’t believe he picked you! Out of the two hundred plus girls who worked for the agency you were the one he wanted to spend the night with – how lucky can a working girl get?

It wasn’t a secret within the agency that many a high profile celebrity, business man or politician frequented “The Dollhouse” for their sexual pleasure and gratification. After all, it was one of Copenhagen’s top establishments for such business. But to land this client was a huge honour and no doubt you would be the envy of all the “dolls” for a long time to come.

Your mind wanders back to this afternoon's conversation with you boss. You had sat there in a daze as you listened intently to Madame Vicky’s instructions that had been passed down from the client. They detailed three important stipulations you were to obey this evening:

1.       what you were to wear – a tight fitting red dress which must emphasis your legs and cleavage, adorned with a pearl necklace and your hair left free flowing;

2.       how you were to act – submissive , no kissing but willing to try anything and everything else (something that excited you yet made you slightly anxious – you were never good with pain);

3.       and you are only to speak when spoken to.

Your boss also informed you that the reason you were picked is not only for your good looks and tight body but because he liked your name – Prudence. She went on to explain that caution and discretion is at the top of his priorities and he thought your “name” was fitting for the occasion, seeing as though these qualities were the basis for practising Prudence.

So after three long hours of primping and pampering yourself to suite his liking, you finally get to sit back and relax against the plush leather seat of the limousine he has provided to transport you to his hotel. You mentally start to prepare yourself for this evening, a little ritual you’ve seemingly picked up over the years in order to make this “job” a little easier to swallow – no pun intended.

You sit there anxious, nervous even. You are never nervous; in fact usually you’re quite the opposite – confident, ballsy and brazen even. After all you’ve been doing this kind of thing since you were seventeen, but the thought of being with THE Michel Jackson has your stomach twisting and turning as though elephants were doing acrobatic tricks inside your guts.

But there is no time for second thoughts, the limo has already arrived at your destination and with one quick look in your hand mirror to check your hair and makeup is as perfect as it’ll ever be, the chauffer is swinging the car door open and is politely holding out his hand to escort you out of the car. You actually feel like someone of worth for a change and it feels kind of nice. Usually you are instructed to make your own way to the rendezvous point and looking back, you could probably count on your one hand the amount of times a limo has escorted you to a venue, yes you could get used to this.

“Welcome to the Hotel D'Angleterre,” the bell boy says to you before holding the door open for you to enter.

You take a deep breath and make your way over to the bank of shiny gold coloured elevators that reflect your image just like a mirror would. You scrutinise yourself one more time before you are satisfied that Mr. Jackson will approve of your chosen attire for the evening. The tight red dress clings to every curvature and dip of your body. Your ample breasts are unrestricted as you’ve decided not to wear a bra, instead they are merely being held up by the tight fabric of the dress. Your run your fingers back and forth against the cool strand of pearls that adorns your neck and a tingle of pleasure shoots through your body as you imagine it is his hands that is gliding over your neck right now.

Usually you find no self pleasure in your work – its business after all! But the thought of spending the night with Mr. Smooth Criminal himself has your loins burning ablaze with desire. You’ve always admired his work and that lithe dancer body of his, but never in your wildest dreams did you ever think that one day he would end up being on the long list of clients who have sampled your goodies.

The elevator door pings open breaking you from your reverie; you have arrived at your destination – the presidential suite. You make your way inside and when he comes into view your breathe catches inside the back of your throat. You see him stood staring out of the window looking at the vast city beneath him, his hair is a lot longer and curlier than you had ever seen before and is secured in a loose pony tail which trails to the middle of his back. You imagine what it would feel like to have your fingers tangled up inside that delicious looking mane. Impure thoughts flood your mind, you yearn for his touch, but he merely stands there statuesque, simply admiring the world below.

“Good evening Prudence,” he says in a voice far deeper than you have ever heard him speak in before now. Where was that high pitched squeaky voice of his that you had heard him speak in numerous interviews in the past?

“Would you like some wine?” he says sweetly, now turning to face you, admiring your beauty and seemingly mesmerizing the way your body looks  in your chosen dress. Unashamed he ogles at your body and looks you up and down not once, not twice, but three times.

A small smirk spreads across his face and he shakes his head before saying something underneath his breath, something along the lines of “very nice indeed.”

You drink in his posture as he walks towards you with confidence; he has a slight arrogant gait you notice, but nothing egotistical, he merely displays a confidence you would never have guessed he had.

The shy, quiet Michael Jackson you’ve been witness to over the years on television looks and talks nothing like that version. This version is much more self-assured and somewhere deep down this excites you immensely.

His fingers reach up and touches the side of your cheek and you feel yourself start to blush. You look down, slightly ashamed that you’ve let this man turn you into a puddle of liquid with just one caress, but he seems to like that he has this effect over you, as when he lifts your chin and looks straight into your eyes he smirks and you feel yourself beginning to drown.

His deep, dark eyes are hypnotising, they look wise, all knowing and the way they penetrate your own, you have the feeling that he can see into your very soul. After a few seconds you manage to break away from his gaze, if you don’t you may not be able to control yourself for much longer and this would break one his three stipulations – not a good thing if you want to get paid.

“You know Prudence, I don't make a habit of this… but seeing as though it’s my birthday, I thought I’d have a little celebration.”

His birthday? Wow, you can’t believe he chose you of all people to spend his birthday with, how lucky can one girl get?

“Are you hungry?”

“No,” you manage to say. For some reason all of a sudden your voice feels extremely parched.

“Are you thirsty?”

Even though you could drink the ocean dry you simply reply “No.”

“Then shall we get down to business?”

Hallelujah you silently pray as those are the magic words you’ve been waiting to hear since your arrival, “Yes Sir,” you say a little too quickly for your liking.

You know full well that men who like their women to be submissive love being referred to as “Sir” and “Master.” You wonder how long it will be until he asks you to call him the latter, as with all men who prefer this form of coupling it’ll only be a matter of time until he does.

He takes you hand inside his much larger one and silently will’s you to follow him. You both make your way through a long corridor until you come to a stop in front of two huge oak panelled doors which leads into the boudoir.

Once you’re both inside he pulls both doors shut and turns the lock, clearly he doesn’t want anyone interrupting what he has in store for you.

You watch intently as he saunters over to a music system in the corner of the room and pops in a CD. The throaty voice of Trent Reznor starts to seep out of the speakers and you stand there glued to the spot. You would never have guessed that this man stood before you listened to the likes of Nine Inch Nails - another fact about himself that seemingly turns you on.

As the music seeps into your pores you start to inadvertently sway to the beat. Your hips move from side to side as you close your eyes and get lost inside the glorious sound of Trent’s voice.

“You like this band?” You hear Mr. Jackson say and your eyes fling open, your cheeks flushing a hue of pink once more, seemingly for a second or two you forgot who you were in the presence of. Music always did have this effect over you, even when you were a child.

“Dance for me Prudence,” your client says before sitting down on the edge of the bed. He signals for you to come closer to him as he opens his legs wide for you to step between them.

“Dance for me,” he says again before he places his large masculine hands either side of your hips. You do as you are told and begin to get lost inside the rhythm of the music. You close your eyes and sway and twirl your ample hips, to the beat of the song. His hands tighten their grip and dig into your flesh and you hear his breathing begin to pick up.

Your entire body is burning up, even with your eyes closed you feel his gaze travelling up and down your body. You feel the moisture between your legs soak into your panties and you wonder how long it will be until he takes you like you so desperately want him to.

As the first song comes to an end you feel his hands snake upwards, his fingers start to caress your breasts over the fabric of your dress. Your nipples harden underneath his touch and you lick your lips as you throw your head back in ecstasy at his touches.

You feel the zip of your dress being fumbled with and in one swift motion he’s pulled it all the way down and the material pools around your feet. You open your eyes to see his own black orbs drinking in your ample bussom. You watch as he licks his lips, his hands find their way back up to your pert breasts and before long his hot, wet lips have latched themselves onto your right nipple.

Your breath catches in the back of your throat, you hear a moan omit from his mouth and the vibration against your flesh sends chills up and down your spine. His free hand makes its way to the mound between your legs and begins to seek out your slit beneath the fabric of your panties.

You steady yourself by placing your hands on top of his shoulders, afraid that you may collapse into a heap on the floor from all of this glorious teasing he is inflicting upon your body. 

You cry out when without warning you feel a long, thick finger enter your woman hood and your grip on his shoulders tighten. He strokes your insides like a man of experience; he seems intent on finding your spot. His finger curls inside you and you feel it brush up against that special place… you gasp… he found it.

Your head cranes backwards as he enters another finger and before long you’re riding his hand as though it was his cock.

Normally YOU were the pleasure giver, the one who made the other cry out in satisfaction, yet this made for a nice change. You could get used to this; being submissive might just be your favourite role to play from now on.

You hear your moans intermingle with those of the music and as the next song builds to a crescendo so does your imminent orgasm. He lets you reach your peak. In fact, he seems intent on getting you off. You continue to wriggle and squirm against his huge fingers and with one final twist your walls start to contract and your nectar starts to seep out of your slit as you watch it trickle down his hand.

His eyes lock with yours; he seems pleased that he has made you cum so quickly. You feel high as a kite, your orgasm so satisfying that you simply want, no crave for more.

You look down to see his fingers slipping out of you. He brings them up to your face and pushes one finger inside your open mouth. You gladly oblige his silent request and within seconds you have licked his digits clean from your juices which surprisingly taste better than you ever imagined.

Slowly he stands up his gaze never leaving yours as he begins to unbutton his shirt. You chew on the inside of your mouth, you’re anxious to see what he looks like naked. You wonder if he’ll be conscious of his body and whether or not the rumours about his skin condition are true, but the more he strips the more excited you become.

If he is embarrassed about his body, he doesn’t show it. In fact he seems extremely comfortable within his skin and when his cock finally springs free from the restraints of his tight pants you understand why. With a member that huge, well he has a reason to be pleased with himself. Why be embarrassed when you’ve got King Cobra nestled between your legs right?

Once again your mouth feels drier than the Sahara desert and you slowly gulp for air as if it is going out of fashion. That must be eight… no nine or so inches… you muse to yourself – wow just how I like them – long, thick and veiny.

He beckons to you in a come hither motion with his index finger and without hesitation you walk towards him.

“Take your panties off,” he commands in a smooth yet direct manner. You obey his command and decide to remove your shoes also—

“No, leave them on,” he instructs, so you stand back up and await his next instruction. Slowly he begins to circle you, reminding you of a Lion circling its prey. You stand there perfectly still and allow him to take in every inch of you.

His fingers trace the outline of your spine, he runs them upwards and downwards… once… twice… three time… goosebumps cover your flesh, a wave of desire washes over you as you feel the moisture begin to seep out of your slit and onto your inner thighs.

“Come,” he commands.

You follow him as he swaggers over to the windows which are covered with a thin, sheer net curtain and you wonder if anyone will be witness to your debauchery tonight. But the truth of the matter is you simply do not care. The whole world could be witness to this coupling and you wouldn’t give a damn, you crave for his touch, you yearn for him to take you how he wants and to abuse your body in ways you’ve never let any man do to you before.

“Turn around, I want you from behind,” his deep voice commands.

You face the wall and await his next instruction. A mirror to your left has been strategically placed by the looks of things, so you tilt your head ever so slightly and out of the corner of your eyes you see him slipping a condom over his thick shaft.

You find yourself gulping down the air as you debate if you are ready or not to take in his entire length with just minutes of foreplay to warm you up. But there’s no time to worry now as his hands have found their way back to your body. One is holding the back of your neck whilst the other grabs onto your hip. He bends you forward and instinctively you rest your palms against the cool wall as you feel him to start to tickle your entrance with the engorged head of his member.

Your ass immediately tilts higher, giving him the access he so desires and without warning he enters you with in one swift forward push.

A strangled cry escapes your throat and tears springs to your eyes. Even though you have been doing this for years, no man has ever stretched you the way this man is doing so right now.

His grip around the back of your neck tightens and he begins to thrust into you faster… harder… deeper… not giving you any time to adjust.

His grunts mix with your cries of pain/pleasure. Before long you relax and offer yourself completely to this amazing creature. His fingers busy themselves between playing with your nipples, clutching at your throat and teasing your swollen nub that tingles each time he strokes it.

He plays your body like a musician would play a fiddle, you’re amazed by how turned on you are right now.

Usually you would have switched off at this point and faked your moans and groans of pleasure. But with him, there doesn’t seem a need to fake anything, he knows exactly which buttons to press and precisely which angle he should stroke your insides. You’re so turned on, that you wouldn’t care if he chose not to pay you, screw it – you may even decide to give him a freebie, call it a birthday present.

When you feel him bite down on your shoulder blade you’re quickly brought back from your incessant daydreaming and slip back into the hypnotic rhythm of his thrusts. You feel his mouth against your ear, his tongue sucks on your lobe whilst his hands ruthlessly pinch and tug at your nipples.

You arch backwards as far as you can, your head now rests against his shoulder and his mouth makes it way towards your neck. You’re dying to kiss him but you know very well that rules are rules and unless he initiates it you are not to go anywhere near his mouth.

His thrusts become frantic and much deeper, you hear a guttural moan escape his lips and this turns you on even more. Your inner walls are being exquisitely tortured with each stab of his length and the familiar ball of fire that burns inside the bottom of your stomach starts to ignite.

But he’s not ready to let you cum, not again so soon. Inwardly you pout when he quickly withdraws from your canal, but you squeal with delight when he picks you up and throws you onto the huge bed just like a barbarian would.

Immediately he flips you over onto your stomach and positions your head so it’s hanging off the edge of the mattress. You feel his hand press forcefully between your shoulder blades as he thrusts into you once again without any warning whatsoever.

He keeps his grip on your back as his other hand tightens around your hip and the ball of fire starts to ignite all over again.

The next song starts to play and it’s one that you recognise immediately. It’s one that you’ve fantasised about fucking to ever since you heard it play on a late night radio station a few years ago.

“You let me violate you…” the song starts and instinctively you can feel his thrusting move to the pace of the song. He only picks up speed when the song hits its peak and for a second you think you hear him sing along…

“I wanna fuck you like an animal…” your head is spinning as he pounds into you ruthlessly, your wails of pleasure are matched with his own as his grunts and groans fill the room.

You feel one of his hands tangle inside your hair as he begins to tug on it each time he thrusts inside your burning hot pussy. You feel his cock twitch and throb, it stretches you to the hilt and you’re pretty sure it’s growing even bigger by the minute.

His balls slap against your ass the further he buries himself inside and your juices squelch loudly with each of his thrusts. You’re desperate to cum, but each time you feel your walls start to contract and prepare you for a mind blowing orgasm; he seems to sense it and begins to slow down. He’s teasing you. He’s building you up so that when you finally get to explode it’ll be something to remember for the rest of your life. He’s spoiling you. No other man will do you like he’s doing you right now and he’s making sure of that by prolonging your orgasm.

“Please…” you hear yourself beg.

“Please what?” he breathlessly pants.

You know exactly what he wants. He wants you to beg him for it. He’s got you to this point, on the edge of ecstasy so that you’ll finally say those words every dominating man wants to hear.

“Please sir…” you cry out.

“No that’s not what I want to hear,” he’s quick to deadpan.

Unable to play this teasing game for much longer you finally give into his request and blurt out… “Please Master let me cum…”

“Much better,” he pants against your ear.

And just like that he begins to thrust into you with such brute force, you’re pretty sure the bed is only seconds away from breaking. His thrusting is that of lightening speed, you feel his sweat drip onto your back and his cries of pleasure intermingles with those of your own.

You bite down on the pillow beneath you as he fucks you ruthlessly, over and over until finally…

Your walls mercilessly clamp down on his shaft as though they had teeth and all you can hear is the sound of him hissing into your ear. You feel him swell even bigger inside your cunt until he lets out a loud strangled cry before slumping down onto your back. His rocking subsides as you both lie there completely and utterly amazed.

Minutes pass and still you stay locked in this position. That is until you start to feel his lips softly brush against your back and shoulders. You feel his hand reach underneath and with one swift move he’s rolled you over to your side so that he’s spooning you, clearly he enjoying taking women from behind.

With only minutes of rest and a quick change of condom is he back inside you only this time you get to enjoy the show. The mirror that was purposely set off to the side displays yours and his naked form perfectly. Finally you get to see what he looks like as he fucks you for the second time tonight.

You wonder if he’ll ever feel spent, he seems to have the energy of a fifteen year old and secretly you hope this night will never end. Even though you’ve barley spoken two words to him, somehow he understands your body so well. He clearly enjoys having sex and you wonder if in fact his previous statement of “he doesn’t usually do this kind of thing” is true. 

But who cares right? For now you get to enjoy his experience and receive the best mind blowing orgasms of your life.

Seemingly dissatisfied with his view you feel your right leg being lifted and you rest the heel of your stilleto shoe on top of his thigh. This position opens you up further to his gaze and you stare into the mirror and watch in wonderment as his black orbs fix on your entrance and his cock moving slowly in and out of it. The sight of him watching you watching him is too much and before long your eyes are clamped shut and you simply let him fuck your body exactly how he wants.

Slow at first, yet the strokes are always firm and deep, until he picks up momentum and he’s back to long stroking you quickly towards oblivion.

“Let go…” he commands into your ear and as soon as you feel his fingers pinching your folds together so that you become tighter around his length you lose it, both of you do.

You’ve never came simultaneously with a man before and you wonder if he ever has. You’d like to think that this was a first for him too, but you highly doubt it is.

As you continue to ponder about who the lucky ladies were with whom he learnt these amazing “tricks” with, he begins to drift off to sleep and before long only the sound of his light snoring fills the room. You wonder if you should get up and leave, but something is willing you to stay. You decide it best to not let your fantasies fill your head, after all it was only a fuck right? But when you make a move to get up you feel his arms tighten around your torso pulling you back towards his chest.

“Stay with me,” he softly whispers inside your ear and ever the submissive slave you simple reply, “Yes Master, whatever you want.”

The End.

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