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The Guiding Hand6: Lessons to be Learnt

by Andy Latex

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© Copyright 2012 - Andy Latex - Used by permission

Storycodes: F/m; fem; makeup; latex; cd; sissy; maid; corset; heels; service; punish; cons; X

(story continues from )

Continued from part five

Part 6: Lessons to be Learnt.

Andy gazed out of the conservatory window, his fingers massaging his poor, high heel tormented, foot. Not he was intent on the pain, no his mind was elsewhere. To be precise it was on the dream he had that night. Again it was of Jane, the beautiful intoxicating Lady Jane, she was a constant part of his nights now, but this dream was so vivid and so wonderful he wished it true. In fact he had been told as a boy, that if you speak of your dream before breakfast it will come true. So he had, to himself as he showered, he had told himself of the dream.

Yet even now, 3 hours later, having completed his upstairs tasks the dream remained. He could still recall he and his friends seated in the dorm at college, of their games and laughter. He could recall their bewilderment as the sun rose and set around them and of the ‘click’ ‘click’ of heels approaching down the corridor. His mind was clear to the shock of suddenly being alone, of running from the heels behind him and of ducking into the shower room. Not the shower room of his college though, but of this house, of Jane’s house and as he stood there he could see her silhouetted behind the glass.

He felt he had stood there forever before slowly the door opened, to reveal his tormentor in all her stunning glory. She turned to him, her eyes as green as in life, looking him up and down. Slowly she placed both hands on her hips and smiled, it was one of her cool smiles, the one she gave when she knew she was in control. And she was, she knew Andy could not look away, but then, almost pleasurably she closed her eyes and the warm, sparkling water which bathed her, suddenly turned to a glistening black rain and began to settle on her superb body in a single smooth, slick and glossy film of latex.

Andy shook his head, the image was so strong, the image of Janes body, slowly being sealed within a second skin a warm shimmering wet skin, perfect and tight, her every dimple and curve revealed to his young eyes like never before and when it had stopped, when she was ceased and enveloped in wet mirror smooth latex, her eyes opened and without words she beckoned him in

“What the hell is this”

Startled and unbalanced in only one heel, Andy jumped to his feet and turned to the sharp toned voice.

Jane gazed down at him from atop her own stunning patent heels, they were the perfect compliment for the seamless and smooth black leather jacket, which fitted so snugly about her upper body, presenting her full breasts to the eye, within the deep plunge of the jackets neckline. Today the jacket was teamed with a simple yet sexy black satin pencil skirt, which like the jacket fitted perfectly so as to display her womanly curves. However if in that moment Andy had had the nerve to look up from those heels he would have seen a face, immaculately made up, yet displaying a look of clear disappointment and anger.

Jane stepped forward, “Well, answer me”.

“I ….I am sorry Lady Jane”, Andy felt himself tremble, her tone was darker than he had ever heard it before and he did not know how to react. “My….my feet hurt. I only took them off for a second”.

Jane looked him up and down, at the way he tried so hopelessly to find a balance on his one glossy red heel. She placed her hands on her hips. “I have been watching you, you have been sitting there for over 15 minutes, sitting with your heels off dreaming and thinking I was elsewhere”.

Andy raised his eyes, his lips parting in their wet gloss as if to protest, but the look in Janes cool green eyes made it clear any such dissent would be very un-wise. He sighed. “Yes Madam, yes I am sorry”.

For a moment there was a stillness, a pause in which Andy expected sharper chastisement, but none came.

“Put your shoe back on”. As if modified by his soft apology, Janes tone suddenly lowered and so Andy still not daring to look up at his tormentor, swiftly obeyed, fumbling with the buckle on the ankle strap, before straightening before her.

“Sorry Madam”.

“Very good”, Jane sighed, circling him, he sensed her looking him up and down, maybe searching for another failing. But then as she returned to face him, closer than before, there came a brush of his cheek and a soft gentle, red glossed fingertip traced a feather-light line down and across his lips, caressing their moistly painted outline.

“Oh Andrew, you are so silly…..”. It was the first time in days she had used is real name and it’s use seemed to warm the young mans heart. “… are so very pretty, you must learn to accept your role”.

Andy nodded slowly, his heart in his throat.

“No darling….”. Janes fingertip now slipped beneath his chin raising his face to hers. Andy swallowed, she looked amazing, freshly made up, with smoky eyes and richly glossed lips. “….you must listen, you are so very beautiful, so feminine and sweet and nothing you can do would change that. Is that understood”.

Andy shifted on his heels, a lump in his throat. He nodded, “Ye…Yes Madam”.

Jane stepped back, running her eyes up and down her beautiful maid in his tiny new, brilliant red latex uniform. “I will help you with the problem of your heels Amanda”. She smiled. Turning away, “But this afternoon I will punish you”.

Janes words had chilled him to the bone, never before had she used the term ‘punish’, it had never come up before, never, but then again he had never been so foolish as to remove part of his feminine uniform before.

And so the word rolled round inside his head for the rest of the morning and as he moved from room to room, his duster and polish to hand, his heels clicking on the wood floor, he could barely concentrate. Indeed so distracted was he that when the door bell rang and Jane called for him to answer it, he was at the door and smoothing his skirt, before he even realised.

“Hello, can…….Oh”. Andy stopped and took a tiny step back, his delicately painted eyes widening in surprise.

For a brief moment the young waiter from the restaurant, his arms full of boxes, just smiled at the blushing beauty before him. But then with a faint cough to clear his throat offered his greetings.

“Hello again”. He smiled

Andys reply was little more than an “Um”, of uncertainty, which just seemed to widen the young mans smile.

“What a surprise”.

Again, Andy “Um’d” and glowed a deep red.

“I never ever thought I would see you again”.

Again the young mans polite words could not break the strange trance which seemed to have enveloped the blushing beauty.

The young waiter cocked his head, “Sorry it’s, Will, Will from the….”

“From the restaurant”, Andy finished, his eyes sparkling, with a clear delight.

There was a pause as both took a breath. A heart beatingly nervous pause. As both seemed to struggle to find a voice.

“I’m….I’m delivering” , The young waiter, William Bennet said, hefting the boxes in his arms, “Don’t usually but, well today I….. do you work here?”

Andy shifted his weight on his heels, and took a nervous nibble of his lips, “Sort of”.

Again a pause.

“You look amazing”.

For the briefest of moments Wills heart leapt into his throat and threatened to throttle him for his unguarded comment. But before he could even think of apologising for such forwardness. An uncontrolled smile had spread across Andy's face, a smile which started on his lips, glowed in the dimples of his soft cheeks and finally sparkled in his widened eyes.

“Thank you”

Will, his confidence warmed now by the glow of Andy's smile, straightened his back, “But does that dress come in a smaller size?”.

“Oh god”, Suddenly remembering the rather brief cut of his red uniform, Andy gasped and tried pulling at the hem of the tiny dress, hoping to gain just another inch or to for his thighs. “I know I’m sorry.”

“Sorry?, for what?”, Will said warmly, “You look…. well amazing, what is that?, is that….. Rubber or something?”.

Again Andy blushed, and played with the uncooperative hem. “Yes, well Latex, but yes rubber”.

Will took a tiny step back so as to frame the young beauty before him. His smile unchecked. “Rubber, latex whatever…. I‘m sorry, but I will have to stick with amazing”.

Andy, his heart racing, shifted his weight and lowered his eyes in genuine delight.

“You know, I thought I had imagined those dimples”.

“Oh god what are you like?”, Andy giggled, now literally skipping from heel to heel, “And you know I had imagined you to be more charming”.

Now Will laughed, his smiled never wider, “Oh come on, I am all charm”.

“Oh I would not say that”. Andy giggled, his hand reaching out to rest on the young mans bare arm, “But, you know you could be cute... if you tried. Even with that nose”, Andy's smiled made it clear is comment was meant in the lightest of fun.

“Hey lay off the nose”, Will laughed, holding it’s slightly battered tip, “Got that in a fight……with a wall, well with a wall and a milk crate….. all right and a skateboard”.

“No I like it, it gives your face some charm”

“Now you are trying to be kind”.

“No really, with a little charm and your smile, who knows. You might pass for Very Cute”.

“What are we listening too”.

Jane jumped at the voice and turned to the smiling face of her beautiful neighbour, who stood behind her in the doorway.

“Where the heck did you spring from?”.

“Back door, what is it?”.

“Shhh”, Jane sighed, moving aside, “look, take a peek”.

Jennifer Keely eased round where Jane hid behind the frame of the kitchen door and peaked her head round. “Oh my god is that him?”.

“That’s him, William. Gorgeous isn’t he”. Jane whispered. “But look at them, they are totally into each other. I knew they would be”.

“Oh my god they are so cute, look at Andy, is that a new dress? God it’s hot and look at his legs, look he dosen’t know what to do with himself. Oh Jane. You were so right.”

“Told you so. Told you Andy was more girly than boy”.

“Totally. I take it all back, He looks amazing. Oh God Jane they are so cute together. What are you going to do?”.

“Well sadly for a start, split them up. Andy is in for a tight afternoon”, Jane purred, a wicked smile on her lips.

“Oh dear has he been a bad sissy?”.

“Shoes off”.

“Oh dear. Poor sticky Andy. Can I come and play?”.

Jane pushed lightly on her friends arm, “No you can not. Now step aside, time I put my bitch face back on”. She stepped into the hallway.

“I was beginning to wonder if I had imagined you”, Will said, seeming not care about the weight of the boxes in his arms, “I mean, no one could be as pretty as you. I had hoped you would come back the next day”.

Andy felt himself blush now, a blush which warmed his entire body, but it did not wipe away his smile. “Do you work there everyday?”

“Pretty much, will you come again?”.

“I don’t know, it all depends I guess”.

“I hope so”.

“So do I”, Andy smiled. His hand still comfortable on the visitors arm.

“That will be all Amanda”, Jane snapped, her hands on her hips, “I will deal with this”.

Andy, suddenly aware of Janes presence stepped back, his hand slipping free at the last moment. “Yes Madam”.

For a moment Jane remained still, she knew Andy had stepped only a few feet back and was still intent on his new friend. She turned. “That will be all Amanda, go to your room and await me”.

Andy jumped at the sharp tone and turned.

“Was it a nice one?”. Will said as Andy turned in a sparkle of polished latex.

“Sorry?”, The feminised boy replied, looking back.

“The surprise, seeing me again, was it a nice one?”.

Andy beamed, his glossed lips straining to contain his brilliant smile. “Yes”. He nodded “ It was, a very nice one”.

With that and a look from Jane, Andy turned and moved up the staircase. Wills eyes following.

Janes eyes now fixed on him, she smiled.

In his room Andy had found a written note, an instruction to remove, clean and talc his little latex maids dress, before stripping and taking a shower. This he did and by the time the door to his room opened and Jane glided in, he was fresh, perfumed and wrapped in a scented bath robe.

She looked him up and down, deliberately not mentioning the previous incident at the front door. She drew he robe away, allowing it to slip from Andy's body and tossed it onto the bed. She circled the silent and clearly rather nervous young man, easing his hands away from where they shield his naked boyhood.

“That is nothing I have not see before”, she purred, moving back before him and taking his hand, “Now come with me”.

It was odd, but after all the high heels, make-up and shiny latex Andy suddenly felt very embarrassed as he was led, naked around the upstairs gallery and into Jane dressing room. She placed him deliberately before the mirrored wardrobes. He blushed and lowered his eyes. Jane smiled.

“Now, as I said Andrew, this afternoon you will be punished for your removal of your heels”.

Andy shifted nervously, his toes curling into the deep carpet. “Yes Madam”.

“There is no need to look so frightened”, Jane added, her tone clearly lighter, “It will not be painful”.

The relaxing of his shoulders, which had been nervously tensed moments before made it clear to Jane, he had been expecting the worst. She turned and with an almost flamboyant movement slid the wardrobe doors open. For a moment she was still, her eyes roaming over the contents within.

“Your punishment today, will be in the form of a lesson”,

She reached in and drew an item out. Placing it on the bed. Andy's eyes widened.

“The lesson will teach you….”.

Another item of dress, slipped from the wardrobe and rippled onto the bed, beside the first. Andy swallowed.

“…that, your day to day, French maids uniform is something of a privilege”.

A third item, emerged and again Andy's eyes fluttered wider still.

“…..and not to be taken lightly”.

Two more items, smaller than the others followed and Jane finally returned her gaze to him. But he only had eyes for the clothing laid out before him. For the pure white, blouse, short sleeved, but high necked. The jet black skirt, calf length, slim and elegant. The pair of smooth black stocking and finally the gloves, the long oprea gloves. All of which, every item made of glistening rippling latex rubber.

Andy swallowed and Jane smiled.

“Head to toe in Latex…. a very sticky lesson on a summer's day”.

Firstly having slipped the beautiful young mans boyhood, into a pair of smoothing black latex panties, Jane had sat him on the bed and instructed him in the art of the latex stocking. Heavily lubricated, they slid up his long feminine legs with ease and with a little time he was able to work the air from out of the toes and smooth the delicate latex up his legs until they formed a perfect, crease free fit.

“Mmmmm”, Jane purred, helping him to his feet, before wiping away the thin bead of lubricant which had risen from the top of the stockings to glisten on his thigh, “Yes, very…. very nice. How do they feel?”.

Andy paused, they felt tight, and weird, but instead he settled on , “Hot, Madam”.

Jane smiled again “Good”.

Now she turned and took up the skirt, quite long, it would clearly fall just below Andy's knees, but it was it’s, sleek cut which, made the future wearer nervous. He knew it would be very, very tight. However it was not until, aided once more by a little lubricant, it had slid up his stocking legs to the wider curve of his thighs, that he realise just how tight.

“Don’t worry daring”, Jane smiled, sensing Andy's uncertainty at the skirts fit, “It will stretch a little. Now wiggle those hips of yours for me”.

Andy did as instructed and slowly, punctuated by the sounds of stretching and snapping latex, the skirt worked its way up and over his slim, boyish hips, finally snapping into place about his waist.

“Phew”, Jane said in mock exhaustion, “There all snug and tight”.

Snug and tight were hardly there words Andy would have chosen, bound and helpless would have been better, for the skirt seemed to squeeze his legs together, from hip to knee in a fashion which even without trying he knew would make walking very tricky indeed.

Jane stepped back, tilting her head in thought as she circled the tightly skirted boy. “I think that is just about perfect”, she purred, letting a light hand drift over his smooth and well defined bottom cheekily cupping his buttocks in her palm. “Mmm yes, perfect”.

Already, as Jane selected the blouse from the bed, Andy could feel the heat building up in the double latex layer which enclosed his thighs and looking up from where she was unbuttoning the flimsy white blouse, she could see him fidgeting under the skirts control.

“Tight?”, she asked.

“Ye.. yes madam”.

“Then cross your knees”, she said looking up to him. Andy once more just fidgeted. Jane sighed and holding the gloss white blouse came behind him. She placed her hands on his smoothly rubberised hips and with gentle pressure, eased one hip down, allowing the opposite knee to slip across. The effect was instant and Andy felt the latex on his thighs relax a little. A very little. For so tight was the skirt, it still stretched between his thighs as smooth as any mirror, leaving only the sleek latex’s tell-tale crease and ripples to reveal its true nature.


Andy nodded.

“You will need to learn a whole new posture for your new uniform”, she held the blouse out, “Now then right arm first”.

Unlike the skirt, the blouse felt quite loose, though well tailored and fitted across the back it was designed to flow and ripple, the delicate puffed sleeves lightly caressing his shoulders and upper arms. With ease and skilled fingers Jane closed each of the tiny, black buttons and as she did she drew the rustling latex together into what was another perfect fit. This was the third item and as Jane's hands smoothed down his body to his hips, he could feel the heat spreading over him.

Happy with the blouse and leaving the top few buttons open, Jane now took up the first glove and instructed Andy to offer his right arm again. If it had not been for the sweetly scented lubricate the gloves would have been an impossibility, such was their perfect fit. Skin-tight would have barely covered it, they were perfect and as she smoothed the air from them, she created a vacuum which almost melted the latex onto his hands revealing even the finest detail of his new long nails.

As he offered up his left hand Jane looked up into his glowing, almost concerned, face. She smiled. “Breath Andrew”.

Andy took a breath, his first for almost 2 minutes and sighed. “Sorry Madam, it’s just that, there is so much of it”.

“And there is more”, Jane said cocking her head, as she eased the second glove up his arm, smoothing the fingers into place, with delicate hands. “I said head to toe and I wasn’t kidding”.

Andy took another breath, his head span ‘head to toe?’.

After a few minutes, Jane had eased the long gloves over the smooth lower edge of the blouses short sleeves, creating a single smooth line of latex from the top of his arm to the tip of his fingers. She stepped back, nodding approvingly.

“Now nearly there”, she said almost to herself, “Lets get you into some heels next”.

As she returned to the wardrobe, Andy remained still. Almost fixed to the spot by the tight latex outfit he dare not move, for any movement would allow a trickle of sweat to pop and flow beneath the smooth material. He stretched his fingers. So tight

“Yes”, Jane said, “Turning back, yes why not”.

Andy now did move, though it was more from shock than intention. The heels Jane held up were simple, ankle strapped, black and glossy. They were also, 6 Inches high, needle thin and fashioned with a one inch platform.

Andy gasped.

“Pretty aren’t they”, Jane said, turning them in her hand, displaying them to him in all their fetishistic glory.

Andy shook his head and with a release of stunned breath said, “Please no”.

Jane's eye widened and a smile of surprise and delight flickered on her glossed lips. “I beg your pardon Andrew”.

“Please, Madam. I don’t think I can wear those”.

“Nonsense, they are perfect”.

“But they are too high”.

Jane paused, slightly taken aback by her young mans boldness. Then stepping closer, much closer until Andy lowered his eyes. “I have higher”, she purred, her breath caressing his cheek, “would you like to try those instead?”.

For a moment Andy remained still, eyes lowered, scared almost. Then with the faintest of movements shook his head.

Now Jane paused and unseen to her submissive young man closed her eyes. She breathed, calming her heart. She did not want to use that tone in her voice again, she did not want to force Andy into anything, but she knew she was so close, so very close. She breathed once more and smiled, “Good boy”.

The latex stretched and complained as she sat Andy on the bed, but sitting him made slipping the heels on easier, doing it standing would have meant a little too much balancing on one heel. Each heel slipped on with a soft sigh, fitting as perfectly as Jane had expected, closing the strap about his slim feminine ankles with a faint click.

Jane straightened, smoothing her own skirt before extending a hand to the young man. “Ready?”.

Andy nodded and with his latex hand in hers, slowly rose to his feet. Jane smiled to herself as she recalled the first time Andy had worn heels and just as then, his grip tightened unable to let go.

“Relax, feel the heels below you, relax onto them, let them hold you. Good, good, just as before, you see”.

Andy nodded, his eyes lowered to his toes.

“Ok?”. Jane slipped her hand free.

To Andy's embarrassment it was history repeating, for, despite the extra inch of heel and there super slim profile, he found himself as sure and confident in them as he had become in his regular heel.

“A natural”, Jane teased, her hand patting his shiny latex bottom. “A natural, now take a step. Be careful”.

For a moment, wobbling slightly, Andy could not raise either foot, “I can’t it is too tight”.

“Don’t worry about your skirt honey”, Jane said, slipping her hand back into his, “It will stretch enough, just keep it tiny and rotate your hips a little”.

She could feel him grip her hand, not tight but enough for her to know he was once more uncertain. Then with a deep breath he placed one foot forward. The latex skirt as promised stretched, but also as promised not much, it gripped and held his legs, unwilling to allow him to move unless he did so at its command. That command was to make him swing his slim hips as if he were a catwalk model whilst placing one foot no more than 6 inches in front of the other. It was a strict and demanding command but one which, after a few wobbles, allowed him to move with a new and shockingly sensual step.

Jane smiled as she gazed at his bottom, moulded to perfection as each buttock rotated and slipped beneath the gloss surface in a sensual dance. She could have watched it all day. But she had one last piece to add.

For a moment, when Jane first slipped it around his waist, he was nor sure what it was, but when she clipped the three tiny buckles together at the front, it became very clear.

Jane smiled at his recognition. “I want to start to train your figure a little Andy, It won’t hurt, all it will be is a little tight.”.

Sensing any form of questioning would be fruitless, Andy, took as deep a calming breath as the already snug, black, moulded rubber corset would allow. Well it was less of a corset and more of a waist-cincher, a very wide belt, which fitted him from the base of his rib cage down to the first outward swell of his hips. But whatever it was called, as the first hiss of the laces that criss-crossed down the back of it, drew the rubber in, Andy knew it would be tight. Then after the second hiss he knew it would be very tight.

“Relax, Andy”, Jane purred, as she worked the laces down his spine, “Deep breath, deep breath”.

Deep breath, that was easy for her to say, for within a minute the waist cincher, had begun its main task, of squeezing his slim boyish waist into that of a young woman’s.

“Up straight dear”, Jane instructed, her right hand momentarily resting on his shoulders, “Up right, let your abdomen relax, Good. That looks good. How does it feel?”.

Andy, took a breath, not a deep one, that privilege had gone a few lace pulls ago. “Tight” He sighed.

With the laces in one hand she drew the other down and over the new contours of her young mans body, she smiled. “Very nice. But a little more I think”.

Andy, if he had had the nerve or indeed the breath, would have complained, but before he could, the ‘hiss’ of the laces once more filled the air. He gasped and felt sure his eyes must have popped, he definitely felt them widen with surprise.

Again, the laces whispered their movement as she worked them down his spine and again they drew a gasp and a panted breath passed his glossed lips.

“That’s it Andy, relax, Little breaths now, little breaths”. Jane placed her hand, gently on his latex dressed shoulder. “Good boy….. now shall have one more?”.

Andy lips parted, but no sound emerged. Not that Jane would have taken notice but it would have been nice to be able to voice his, discomfort.

Jane patted his bottom, “Very well, one more it is, now relax”.

‘Hiss….hiss…..hiss…..hiss’, went the laces down his spine and for a moment Andy, his eyes closed and his breath clenched in his lung, thought he must have been split in two. However after a long moment, his breath, demanding release, drifted from his body and to his surprise, the next was drawn in with ease. It was not a deep breath, but a soft, half breath, but still it filled his head and relaxed his body.

Jane, smiled to herself as she sensed Andy's body, succumb to the control of the now very tight garment. So after tying off the laces into a sweet, but unseen bow at the base of his spine she allowed her hands to caress down his body, to rest on his now, clear and very femininely curved hips. Gently she turned him toward the mirror which adorned the far wardrobe door. Andy gasped.

He had every right to gasp, for the effect of the mini corset was clear to see, where once he had a slim boyishly feminine figure, now he had genuine curves and a waist as slim as any catwalk model.

Jane let him stare for a moment before turning him into profile, again the effect was clear. His stomach, not ever a problem, was now perfectly flat whist his bottom, naturally cute and girly, now seemed to curve outward with a new sensual roundness.

Again Jane's hands slipped over his body, a gentle reassuring caress. She smiled into the mirror, “Doesn’t hurt does it?”, she asked with genuine affection.

Andy, shook his head. If he had said yes it did, she would have most certainly relaxed its grip, but, it did not hurt, it felt, odd, tight yes, but odd, almost….. comforting like an embrace. Whatever it was Andy liked it. “N…. no. It’s fine”.

Jane smiled and patted his bottom. The tight latex rippling to her touch. “Good boy, now lets get you polished and no more surprises. I promise”.

Andy's fingers, flexed nervously in their tight latex gloves as Jane completed the now familiar ritual of his polishing and, as before, it left the once muted and dull latex glistening wetly like warm syrup in the summer sun and making its wearers every movement a sensual and erotic delight.

Indeed it was a delight which Jane drank in all that afternoon. From wherever she was in the house she would either listen to the click of his heels, their step restricted by the clinging latex pencil skirt or best of all watch his exquisitely feminised figure, moving within its new sensual uniform as he went about his duties. For it was still very much a uniform, however the addition of the delicate cap, with its trailed ribbons, the tiny apron about his now moulded waist and the bowed ribbon closing the blouse about his throat, only added to the effect and nothing, nothing could possibly detract from the way the warm summer sun, shone and reflected from his every curve to highlight and emphasise, his now impossible to deny femininity.

It was also femininity reflected clearly in his every movement. For in the next few hours, as he went about his well planned duties, his body learned to sway, compensating for the tight, yet lovingly yielding skirt, as well as developing a new higher elegance required to balance atop those heels. However if the uniform, had been a punishment, a tight, hot, sticky punishment, for his transgressions with his heels, it was also, unknown to Andy, a hint of things to come, and of plans Jane had already laid in place.


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