Silken Tales

by Christina Shelly

  "There's no point in fighting, it Daphne – you're a natural. Your mother should have put you in panties at the first sign of puberty. That would have saved us all a great deal of bother."

  Helen's teasing words had rung like bells of doom across the last few, utterly bizarre weeks, and as soon as the wig was positioned, he had wiggled his way back over to the wardrobe to extract his very finest maid's costume. Today he would serve his mistresses breakfast in bed, a key part of the Sunday ritual, and Daphne had to look her very best.

  He had opened the nearest and largest of the two huge wardrobes and felt the true nature of Helen's determination hit him hard in the gut. No expense had been spared, no ounce of perverse imagination had been wasted. His flat was already up for sale, and she had made it clear the cost of this elaborate transformation would be recouped from the proceeds: he would pay for his own destruction. The darkest and perhaps most wicked part of the plot against him. Yet he could not help but be impressed by the sophistication of the planning that had gone into his feminisation.

  Before him had been a row of incredible dresses: a dozen masterpieces of sissy enslavement that announced in a most spectacular fashion the inescapable reality of his feminine fate.

  Carefully, gently, even fearfully, he had selected a beautiful black silk dress, a work of sissy art with a very high, white lace-frilled, button up neck, elaborately puffed shoulders and sleeves (which were also ringed with deep white lace frilling), and a very short, layered skirt. Sown into the rich fabric of the skirt was an ocean of lace net petticoating, four beautiful, delicate layers, all white with gorgeous strawberry coloured trimmings. He had felt the soft electric silk brush against his hypersensitive shaven form and gasped with an avoidable and quite terrible pleasure. Terrible because so very revealing: after two months, he could not deny that he found so many of his sissy costumes attractive and, without doubt, arousing. At first, of course, he had been utterly disgusted and appalled, but, given the sentence hanging over his head, without a choice. But now, to his deep shame, he could admit the feel of these pretty, sensual feminine materials was becoming more and more pleasant. In that at least, his mistresses were succeeding with their efforts to turn him into a willing she-male slave.

  He had then carefully laid the dress across the dressing table stool and returned to the wardrobe. Beneath the other amazing dresses (six maid's dresses of various colours and designs, a school uniform, a little girl's dress in the Victorian style and two very elaborate and deeply humiliating baby outfits - one of which he would be forced into later that day) were a row of white drawers with elegant silver handles. Resting on top of the drawers was a collection of stunningly feminine shoes. All in his size, all very high heeled and all made from gleaming patent leather. He had selected a pair of gorgeous black court shoes with spectacular five inch heels. He had placed these by his helplessly feminine feet and then began extracting his under things from the drawers. A pair of expensive and very sheer black nylon, seamed tights; a darling cream silk slip and a pair of heavily be-frilled, white silk panties. He had taken these, together with the shoes, back to the dressing table, his heart now pumping with a strange but not unfamiliar mixture of fear and sexual anticipation. Then he had minced over to the second wardrobe. He had pulled back the door with a deep sense of defeat, for here were stored the most sinister and overwhelming tools of his dreadful transformation: the body girdles.

  There were five of them, each reflecting different levels of feminisation or sissification, each designed to provide a certain physical appearance. Each was fitted with thick rubberised padding at the hips and breasts, with very tight, figure shaping side panels. Each had an outer frame of silk-lined elastane which allowed the girdle to be stepped into and pulled up the body, before it contracted to meet and ultimately very firmly shape the torso, especially the waist area. Ingenious and wicked, these kinky girdles were at the very heart of his daily physical transformation.

  As well as the girdles, each of which was a different colour, there were a collection of dainty, pretty and heavily be-frilled white silk pinafores, plus a set of drawers containing more tools of babification: silk booties, rubber lined and fingerless silk mittens, ankle socks, bibs and king-sized dummies. Two pink silk romper suits were also hanging next to the girdles and the pinafores.

  He had wearily selected the jet black body girdle, which, he had been told, most accurately reflected the body shape he would eventually attain through the hormone treatment and plastic surgery - should he agree to full feminisation. His cock had twitched painfully in its evil, pin-lined re-strainer and once again he had been confronted with the dreadful choice that Helen demanded he make if he was ever to be released from the restrainer and the more severe forms of his silken servitude.

  'The choice is simple: you remain subject to the regime of punishment or you accept your natural trans-sexual personality, including the body and lifestyle that goes with it.'

  Put simply, if he were to accept permanent feminisation, he would be allowed a form of freedom, or rather a less painful and constant form slavery. This was the only deal. He would never be allowed to return to his previous male self, unless of course, he wished to go to prison.

  He had taken the girdle over to the dressing table and set it down on top of the gorgeous black silk dress. Helen referred to the girdle as "the Sex Bomb", and it had been made very clear that she expected him to wear this whenever he was acting as her personal maid, which was most of the time.

  While still looking down at the girdle, he had taken a bottle of very expensive French perfume form the dressing table and proceeded to cover his shaven body in a powerful rose scented mist. Then he had picked up the girdle and very carefully placed it on the floor before gingerly stepping into the upper section. He had slowly drawn the girdle up to his knees, so that he could slip his feet through the leg sections and then began to pull it up his long, silken legs.

  The majority of the girdle's deeply embarrassing padding was at the hips, the crouch and stomach area and, most spectacularly, at the chest. The chest section was in fact a thickly and expertly padded bra which was about to provide him with a particularly impressive and very convincing forty inch chest. The chest padding was made up of two rubber breast forms filled with silicon which had been sown inside the cups, and he had been sarcastically assured by Helen that they provided a very realistic "feel".

  Pulling the girdle into position had required a significant amount of sissy wiggling and straining. The elastane and rubber material almost immediately began to contract against his slender form, and by the time he had managed to pull the surprisingly strong silk shoulder straps over his girlish shoulders, the material was already squeezing the air from his lungs.

  A familiar sensation of complete helplessness washed over him as he had wiggled the girdle into its final, figure shaping position. The weight of the breasts tugged at his slight chest, the rubber panels tightly restrained his already trim waist. Special padding at the hips and backside gave him a set of distinctly feminine curves, and most disturbing of all, his hard, tortured and tightly ringed sex had disappeared completely thanks to ingenious padding around the crotch area.

  He had looked at himself in the dressing table mirror and saw a terrible, soul destroying truth: he made a frighteningly convincing woman, a fact that was, to his increasing astonishment, arousing.

  They are winning, he had thought, taking up the delicate, sexily seamed tights. And they win a little more every day. And as their resolve and its startling manifestation became stronger, his resistance surely weakened. As the painful punishments increased, as the terrible working day seemed to get ever longer and harder and thus ever more exhausting, as his sexual frustration deepened, his will to hold out against complete and permanent feminisation was slowly fading.

  He had taken the lovely dress off the stool and laid it very gently across the dressing table. Then he had lowered his pretty, tightly girdled bottom onto the stool. As he had done so, the rubb
er and silk material of the girdle pressed between his legs and forced the vibrator a little deeper into his back passage. He had fought a moan of pleasure, but quickly submitted to a squeal of helpless delight. They were conditioning him to a fetishistic transvestism and anal sexual servitude. Exhausted and desperate (he had had no form of sexual release for eight weeks), he was surely approaching breaking point.

  His cock had stiffened and the pins and rings dug deeper. He was being punished for his arousal and his fundamentally physical masculinity. Pleasure meant pain, as it always did in this strange and terrible regime of total petticoat punishment.

  Then pain became pleasure, a terrible tactile pleasure that betrayed how powerful his transvestite need was becoming. As he carefully eased the soft, teasing tights over his small feet and up his silky smooth legs, he had experienced the most powerful of all the fetishistic pleasures that were being used to train him, to turn David very surely into Daphne. There was nothing as uncontrollably and irresistibly pleasurable as the feel of this so soft nylon on his ultra-sensitised, shaven skin. As he stood up to pull the tights up over his thighs and position them around his tightly girdled waist, he had faced the terrible double pleasure of their feel and the impact they had on his legs. Suddenly, even he believed he was Daphne!

  In between straightening the seams with great care (crooked seams always meant at least a sound paddling on his bare bottom), he had looked into the mirror and watched himself move. Automatically feminine now, graceful, even balletic; as if the tights were possessing him - as if Daphne were possessing him!

  He had moved his hands over his nylon sheathed legs and gasped with a deep, dark pleasure. The pins had bit a little deeper and he was dragged painfully back from this sensual self caress. Then he had taken up the sexy, be-frilled panties, stepped into and then guided them up his teased and tormented legs. And the panties had quickly been followed by the elegant silk slip, with its intricately woven pattern of white silk roses and exquisite lace frilling at the short hem, which barely covered the sexy panties.

  Then it had been the turn of the dress, the most spectacular symbol of his sissy submission. He had taken it from the dressing table and unzipped the long silver zipper that ran from the top of its high neck down to the base of its full, petticoat-filled skirt. Then, swallowing hard, feeling a terribly ambivalent sexual dizziness wash over his feminised form, he had stepped into and pulled the dress up over his reluctant she-male form.

  Guiding the puffed sleeves over his thin, silky soft arms, he had gasped with pleasure, and as he pulled it up around his shoulders and neck, the dreadful sense of inescapable entrapment had reached its erotic height.

  He had carefully and somewhat painfully zipped the dress up, a process that involved considerable contortion without assistance. He had then stepped into the shoes with a careful, deeply feminine ease. It had taken two days and many cuts of the cane to train his body in the art of high heeled balance. But now, like so much of this dreadfully kinky transformational process, he moved with an almost natural elegance and control, feeling his hips wiggle almost instinctively as he had minced back to the wardrobes, taking a series of delightfully dainty and tiny steps, his bottom dancing sweetly, his long, nylon sheathed thighs brushing so teasingly together with each ultra-feminine step, his expertly designed false breasts and padded hips working with the gleaming heels to produce a splendid reproduction of feminine grace, a perfect combination of balance and movement.

  From the second wardrobe he had taken one of the stunning white silk pinafores and held it up before his white, doll-like face. It was a pinafore heavily be-frilled, with two large silk ribbon ties and, stitched in the style of an elegant Victorian handwriting across its chest, the word "Daphne".

  Quickly, he had slipped the pinafore over his head and secured the two silk ribbon ties in a fat bow at the base of his silk sheathed spine. Then, from one of the drawers beneath the dresses, pinafores and baby attire, he had taken a small French maid's cap of white silk, with two lengths of matching ribbon tied to it. He had then carefully pinned this final sissy touch to his thick, blonde hair, making sure the ribbons ran down the back of the wig like two silk ponytails.

  Then he had wiggle-minced back to the bathroom to check his appearance in the full length mirror. As usual, there was a gasp of amazement, a never-ceasing sense of how real, how convincing, how utterly total this transformation was. He was the perfect fetish doll, a male fantasy figure cleverly turned against its creator. He had watched his silicon bosom raise and fall as his chest heaved with a heady mixture of desire, fear and self-disgust. He had felt his cock complain bitterly and his heart pound. The vibrator had twitched so pleasurably in his back passage. He was overwhelmed and utterly subjugated. He had practised the short, sweet curtsey/bob demanded by Mistress Helen, flashing his pretty panties in the process, and knew even this simple act of submission was beginning to turn him on. Then there was his mother's voice still ringing teasingly down the years. 'You really are so pretty, Dave. You should have been a girl.'

  Then he had spun around on his erotically high heels and minced from the bathroom, out of the spare room and downstairs to the kitchen.

  *

  As he struggles so very desperately and uselessly in his tight, punitive sissy bondage, alone in total darkness, his body racked by so many carefully planned and cruelly imposed pains, he continues to remember: to remember how he was trapped by the weakness he had always fought against, and also to recall angrily and painfully how this latest punishment had come to pass.

  He remembers the office, the large open plan office on the third floor of the company headquarters. He remembers his own section manager's office, at the far end of this larger office area, with Helen's slightly smaller office next to his. Helen Bliss, the beautiful, highly intelligence and very capable deputy section manager. He had been against her appointment, because she was all these things, and thus, to him, a very real threat. But the area manager, another strong minded and ultimately frightening woman, had over-ruled him.

  Helen, with her postgraduate degree in philosophy and her cool, calm confidence, had immediately proven very popular with the staff, and - to his surprise - productivity had improved. He had sought to use this to his own benefit, by giving her the primary personnel management function, by allowing her to deal with all the stupid, pointless and petty problems this gaggle of silly females constantly laid on his already overburdened desk.

  He had hoped that would finish her. But no: she addressed all their issues with good humour and reason, and he hated her all the more. He hated her almost as much as he desired her. And while he remained cool, aloof and periodically angry, deep down he had already become her slave.

  She was a gorgeous, plump brunette, with soul melting brown eyes and soft, full lips that were always painted a provocative blood red. As she was also nearly six feet tall, the extra weight she carried was barely noticeable, but it added perfectly to her generous personality. She dressed in tight white silk blouses, long, tight black skirts, black hose and high heeled court shoes of gleaming black patent leather. Now and again she would where spike heeled boots. And her hair was always tied in a tight bun with a glittering diamond clasp.

  He would sit in his office, imprisoned by desire and fear, and stare out at her splendid form with irritated, frustrated eyes. He dreaded standing before or near to her, as she would tower over him and whisper his name with a terrible condescending politeness, her voice pure honey, her perfume powerful and delicately rose scented.

  'Can I help you, David? Is there something I can do to help, David?'

  Outside the two offices were the desks of the secretaries, Sally and Sandra. Sandra, his long suffering personal assistant and Sally, appointed a few weeks after Helen's arrival. Sally, who stopped his tormented heart the first time his tired eyes fell upon her heavenly form. Stunning Sally Glass, Helen's most personal of assistants.

  Sally, even taller than Helen, with her long, golden blonde hair and her
ice blue eyes; with her athlete's figure and her startlingly bold and friendly smile. Sally in her tight sweaters and very short skirts, her long, so very long legs sealed in the sheerest of black hose and resting on the highest of heels. An impossibly beautiful and desirable creature, the perfect match for Helen.

  On some days, it would be unbearable. Seeing the two of them, so gorgeous, so absolutely in control, every black thought about manipulating womanhood would well up in his sad, teased mind, thoughts surrounding a molten core of angrily repressed desire and an increasing sense of helplessness. Then he would slip from his office, so painfully aware of his rock hard erection, a stiff barrel of frustration and need. Then, in a cubicle of the men's toilets, he would masturbate himself to nihilistic orgasm, his come splashing against the cubicle door, tears of despair filling his eyes and his mother's teasing voice ringing in his ears. 'You're far too pretty to be a boy, David.'

  Then something strange happened. Despite his rudeness, his work monomania, his apparent lack of any normal human feeling, Sally had begun to talk to him, to communicate in a gentle, careful manner, to express a very obvious and powerful interest. For the first time in his life, a woman seemed to want him!

  He was 25, a virgin, so terribly lonely and so obviously frustrated. He had even heard one of the office staff refer to his need to be "taken in hand" by a woman for his "own good".

  Then Sandra went on holiday for a fortnight and it was agreed Sally would help him out. There was a big job on. He was working 14 to 16 hours a day. Work was the only thing keeping him sane. She was staying with him after work, sometimes until nine or ten. Always smiling, always so very helpful. Always so unbearably sexy.