Silken Tales

by Christina Shelly

  ‘I’m afraid there’s been an accident…with Chris.’

  Chris had been trying desperately to cover his stained crotch, but Marisa had spotted it immediately and roughly pulled his hands away.

  ‘Oh for god’s sake,’ she had cried out. ‘Not again!’

  Chris had whispered desperate apologies and begun to cry. Marisa had shaken her head in despair.

  ‘This is the final straw, Chris. You know what I said would happen if you did this again.’

  A look of sudden terror had filled Chris’s pretty eyes. Between the sobs he had begged for mercy. Then Marisa had pulled him from the chair.

  ‘We’re going out,’ she had said to Delia, opening the office door. ‘Come to my house…at about seven.’

  Then she had dragged the poor, sobbing boy out of the office and down the corridor to the lift.

  Amazed, Delia had walked out into the office. The ladies had faced her with equally astonished looks. Then they had all burst into loud laughter.

  *

  Now she watched Babs tease Christabel with baby talk and promises of the “fun” they would have that evening. The sissified she-male was no doubt blushing furiously, but it was hard to tell thanks to the thick layer of permanent white foundation that covered her face; this plus two heart pink rouge tattoos (one on each cheek) gave her the appearance of a very pretty china doll.

  Yes, tonight Christabel would spend the evening at Babs’ house and the look of genuine fear in the sissy’s lovely, wide eyes betrayed the particularly perverse power of the plump beauty’s imagination. Babs was a 38 year old divorcee with a very beautiful teenage daughter, Sharon, only a few years younger than Christabel. Although a rotund woman, she was still very attractive, with thick, wavy and perfectly sculpted blonde hair, very full, blood red lips and large dark brown eyes. Today she was wearing a gorgeous white satin blouse that perfectly accentuated her very large bosom, a knee length check skirt, sheer black nylon tights and a pair of very high heeled, open toes mules of gleaming black leather. Her large but deeply sexual form seemed to have been poured into the tight, sexy clothing and Christabel, despite her humiliation and horror, was clearly fighting a furious sexual attraction.

  It had been Babs’s idea to properly sissify the feminised Chris, a proposal made soon after the poor boy had first been “revealed” to the office.

  Delia remembered that first day and the night before, the night following Chris’s swift removal from the office by his angry, stunningly beautiful Aunt Marisa. Delia had arrived at Marisa’s house just a few minutes before seven. Her heart had pounded with excitement as she pressed the door bell with the tip of a carefully manicured, blood red fingernail.

  Marisa had opened the door almost immediately. Delia had been unable to resist a gasp of amazement, for Marisa was dressed to kill in a very tight black dress that barely reached down to the middle of her thighs. The dress had revealed her long, perfectly shaped legs sheathed in the sheerest black nylon and its figure hugging design had further accentuated the still curvaceous essence of her figure, especially her firm, substantial bosom and exquisitely formed backside. Her short blonde hair and long, angular face added, as usual, an ambivalent touch of the masculine, but it had in no way deflected from her essential physical beauty. All of this, plus a pair of 3 or 4 inch heeled stiletto heeled, black leather court shoes, had given the impression of a truly startling Amazonian goddess.

  ‘God,’ Delia had whispered, her voice horse with arousal, ‘you look incredible.’

  Marisa had smiled. ‘Thanks. You too. Come in… I have a surprise for you.’

  Delia, her wide dark brown eyes pinned helplessly to Marisa’s gorgeous backside, had followed her lover into the large living room of the opulent house. Here she had found herself confronting what initially appeared to be a rather lovely teenage girl. Then her mouth had dropped open in amazement. For the pretty creature in front of her was in fact Chris dressed as a girl!

  The teenage boy had been clad in a white blouse with a Victorian style high neck, a short black skirt, very sheer black nylon tights and a pair of very high heeled, black patent leather court shoes. His hair had remained short, yet clip on pearly earrings hung from both ears, his full, always feminine lips had been painted a dark red, a light foundation had been applied to his face and his eyelids had been painted a very pale blue. There had been no sign of any padding: this was Chris in female clothes and nothing else. Yet the impact of the clothes and make up were truly striking: Chris made a convincing, indeed rather beautiful young woman.

  ‘Seeing he ruined his male clothes, we went shopping for something…more appropriate,’ Marisa had said, her striking blue eyes filled with cruel mischief. ‘He cried like a little baby in the shop, but the female assistant, a pretty teenager about his own age, was very helpful.’

  Large tears of despair and humiliation had welled up in Chris’s eyes as Marisa had detailed the process of his feminisation. Delia had been unable to keep her eyes off of the feminised boy. She was especially impressed by his long, curvaceous legs, so effectively displayed by the sheer hose.

  ‘He’s been quite naughty about it all, I’m afraid. He got particularly upset when I shaved his body hair. But then I demonstrated my physical superiority and he quickly submitted.’

  ‘He’s...lovely.’

  Marisa had smiled and nodded. ‘Yes, and this is only the beginning. With a bit more work, he will make a rather darling niece.’

  ‘You’re going to keep him like this?’

  ‘Oh yes. He’s been giving me trouble ever since he got here. Especially this sex business. He’s completely out of control...he’s even hard now. And the little pervert’s been stealing my panties as well. It can’t go on, Delia. We need to deal with him...properly.’

  ‘We?’

  ‘Yes, me and you...and the office girls.’

  The possibilities had begun to reveal themselves almost immediately.

  ‘You need a new girl in the office to take up the slack,’ Marisa had continued. ‘Well this is her...meet Christabel.’

  Delia had burst out laughing and poor Chris had burst into loud tears.

  ‘No!’ he had suddenly shouted. ‘No, please Auntie, don’t do that! I’ll do anything! I’ll behave myself, I promise!!’

  Marisa had then walked forward and slapped him hard across the face.

  ‘Be quite you little sissy fool!’ she had shouted, before taking him up the ear and leading him begging for mercy from the room, his desperate high heeled totters seconds away from complete loss of balance and collapse.

  There had been more shouting outside then a muffled squeal and a tearing sound. A few minutes later Marisa had returned with a totally subdued Chris. Delia’s eyes had had widened further as she saw that a wide strip of white tape now covered his mouth, and that his cheeks were bulging with some form of fat gag. Also, his wrists had been bound tightly behind his back with what looked like a black nylon stocking.

  ‘Stand with your face to the wall.’

  Fighting to maintain his balance, his beautiful eyes wide with a very fetching mix of girlish fear and anger, poor Chris had tottered over to the far wall and stood facing it, his muffled sobs filling the room, his delicately feminised form shaking with fear, humiliation and despair.

  ‘I’ve gagged him with a pair of the soiled panties he stole,’ Marisa had said. ‘They should keep the little deviant quiet while we talk.’

  He had spent the next two hour facing the wall while Marisa had served a salad and two bottles of wine for dinner. She had explained her plan in detail: to replace sullen, shy and rather useless Chris with pretty, able and more than willing Christabel. She had already agreed with Chris’s long suffering mother that her son should be subject to strict petticoat discipline and withdrawn from university immediately. The sissy would live with his Aunt Marisa and take up full time employment as a clerical assistant at Strickland Publishing. Christabel would report directly to Delia, although all the women would be
involved in her training as both a member of staff and as a sissy slave.

  Delia had soon become enthralled and fascinated by Marisa’s plans. She had also become increasing aroused, both by the prospect of transforming Chris into Christabel and by the great beauty of her lover. And soon they had been kissing and Delia’s hands had been caressing Marisa’s nylon sheathed thighs.

  ‘Let’s deal with the sissy first,’ Marisa had said, her voice hard with desire.

  She had told Delia to wait a few minutes while she put Chris, now Christabel, to bed.

  The pretty, deeply reluctant teenage she-male had then been led from the room moaning with fear and shame into the tight, humiliating gag, but too frightened to resist any further. His tear soaked, frightened eyes met Delia’s as he had tottered past her, the sound of his nylon imprisoned thighs rubbing together, a product of the tiny mincing steps he had been forced to make by the stiletto heeled shoes, and filling the room with the sound of his or rather her ultra-feminised future. Yet even then, as he faced the bizarre prospect of sissy servitude, he had been obviously his aroused: his erect penis had been clearly visible through the tight cotton material of the mini-skirt. And as his eyes had turned to his beautiful aunt, Christabel’s tormented eyes had fallen upon her ample backside with a dreadful, aching lust.

  Later, just before they had retired to Marisa’s large, elegant bedroom for a night of intense and quite astonishing love making, Marisa had taken Delia to the small spare room where Christabel, slept. To Delia’s amusement, the poor sissy had been dressed in a very pretty pink baby doll nightie and a pair of opaque white nylon tights. His, or rather her hands had been tied to the sides of the modest single bed. Her ankles and knees had been tied tightly together with nylon stockings and then his ankles had been tied in place by another length of stocking to the foot of the bed. But the truly startling part of this new bondage was the pair of pink silk panties that had been tied over her head. Still tape and panty gagged, the new panties had been carefully positioned with the gusset spread over her nose and sealed mouth and tied in place with another nylon stocking.

  ‘Fresh from a hard day at the office,’ Marisa had joked, indicating that the panties spread so cruelly and deliberately over Christabel’s face were those she had worn during the day.

  The poor sissy had wriggled and squealed and struggled uselessly against her tight, expertly secured bonds.

  Marisa had then stepped forward and pulled up the front of the pretty nightie to reveal the sissy’s furious erection straining against the material of the white tights.

  ‘Don’t worry,’ she had whispered, ‘she’s enjoying every minute of it.’

  They had left poor Christabel, tormented and so profoundly humiliated, struggling on the bed. As a final demonstration of her absolute power, Marisa had flicked off the light to Christabel's room as they departed, plunging the moaning, helpless sissy into absolute darkness.

  *

  Delia remembered that strange liberating night and the months that followed it. She remembered how Christabel had been introduced to the office in an outfit that had been very similar to the one she had worn on that first exciting evening. The girls had been amazed and delighted. They had spent the day teasing and humiliating their new, very pretty clerical assistant. Despite the close proximity of the women and their determination to tease him to absolute distraction, there had been no more orgasmic outbursts. This was because Marisa had purchased a cock restrainer from a local sex shop on that first afternoon of strange, fateful shopping. The device, a sheath of hot pink latex rubber, covered the cock and balls and was held tightly in place by steel rings fixed around the scrotum, the base of the cock and just beneath its bulging, angry head. It allowed more or less full erection, but made ejaculation quite impossible.

  Over the coming days and weeks, the structure of Christabel’s servitude had taken bizarre and beautiful shape. The girls had quickly made it clear they wanted a much more decorative sissy. The normal female clothing was thus replaced with more intricate sissy attire. Outrageous baby girl costumes had become the norm, purchased from the office’s “staff development fund”. A special online catalogue of sissy clothing had been created using the company’s desktop publishing software. With links to every major supplier of adult baby and sissy clothing, it had become a treasure trove of wonderfully humiliating sissy clothing. Poor Christabel was transformed into a beautiful, outrageous fetish doll, the teasing and tormented plaything of a group of determined and, in their various ways, vengeful women, Yes: the transformation of Christabel into the perfect sissy had undoubtedly been informed by years of bitterness towards the arrogance, cruelty and violence of the male sex.

  Then the girls had agreed the rota: for at least one day a week, poor Christabel would spend a night with one of the five secretaries. At weekends it was agreed the lovely sissy would stay with Marisa and Delia. The humiliations that Christabel experienced during the weekday evenings were varied and many, especially given that two of the girls had boyfriends who had become great admirers of the Office Sissy. But at least tonight Christabel would not face the prospect of meeting the demands of a master as well as a mistress. No, tonight the pretty sissy slave would be with Babs Carter and her lovely teenage daughter. It had been Babs, more than any of the other secretaries, who had pushed for the babification of the sissy: the introduction of the bibs and fingerless mittens, office feeding time, and the anal plug now fitted so tightly into poor Christabel’s arse virtually every hour of every day (a devilish means of ensuring that the sissy was constantly sexually tormented and humiliated in the most intimate way imaginable). Indeed, every tiny, high heeled step the pretty sissy took ensured the teasing movement of the phallic shaped plug and thus that Christabel was constantly quite mad with unfulfilled sexual need.

  Delia rose from her desk and walked out into the main office. It was nearly lunch time. She came up behind the sissy. Christabel turned and automatically performed a deep curtsey before the gorgeous mistress. She placed her mittened hands behind her back and cast her sex soaked gaze submissively down towards Delia’s high heeled court shoes.

  ‘I take it everything is ok?’ she asked Babs.

  ‘Oh yes,’ Babs replied. ‘Just talking to Chrissie about tonight. I’ve managed to find some really comfy adult sized pampers and Sharon has bought our little petal a lovely new romper suit.’

  Christabel whimpered into the inescapable gag. Tears welled up in his pretty eyes. Delia was almost overwhelmed by a sense of absolute power framed by deep satisfaction.

  ‘Good. Sounds like our little sissy angel will have a lot of fun.’

  Babs smiled broadly and patted the sissy on her knickered bottom.

  ‘Isn’t it about feeding time?’ Delia asked.

  Babs’ generous smile broadened. ‘Oh yes, it’s definitely feeding time.’

  From a drawer in her desk, she then took two large baby’s bottles filled with sugared full cream milk and two jars of baby food. The poor sissy’s eyes widened in horror, but she made no move to resist. It had been Babs who had also suggested they buy an adult sized high chair and put it in the storage room, thus creating the daily entertainment of “baby’s feeding time”, when the girls took a cruel and intense delight in feeding their helpless sissy slave like a two year old baby girl.

  Babs got up from her desk and announced in a teasingly sweet voice “feeding time!’ The other girls cheered and clapped. Then Babs, followed by the girls and Delia, led a sobbing, but furiously excited and desperately tottering Christabel towards the large store room and the latest challenge of his role as the Office Sissy.

  6. Mother

  It is just after 7am when I enter Mother’s bedroom carrying a silver tray holding her breakfast: a bowl of fruit salad and a cup of hot black tea. The room is shrouded in darkness and I totter forward on my three inch high stiletto heels with care, although by now I am used now both to the demands of the heels and the geography of Mother’s large bedroom.

&nb
sp; I place the tray on her bedside table with a much practiced and now virtually instinctive feminine grace, bending my knees slightly and pushing my bottom upwards, aware that the short skirt of my dress and the layers of petticoating beneath are now riding up my nylon sheathed legs to reveal my semi-transparent plastic panties and the thick Pampers-style nappy secured beneath. The panties themselves are a constant reminder of my sissified condition, their humiliating rustling and squeaking a perverse accompaniment to my every dainty step.

  Mother stirs as I wiggle mince over to the curtains and then open them just enough to provide light to see. As I totter forward, taking the tiny steps demanded by Mother and my nanny, the fierce and wonderful Miss Madeline Sterling, I feel the anal plug push deeper into my arse and fight back a cry of helpless pleasure. My cock strains against the fiendish embrace of the rubber restrainer and a further moan is consumed by the phallic shaped dummy gag filling my mouth.

  I turn from the curtains to discover Mother sitting up in bed regarding me with a look that betrays cruel amusement, deep maternal love and something close to arousal.

  ‘You look lovely as usual, Daisy,’ she says, before yawning and stretching out her long, tanned arms in a gesture of profound satisfaction.

  I fight to avoid staring at her beautiful form, knowing I will be punished for such an act of naughtiness. I perform a quick bob curtsey which once again reveals my babyish underwear. With my head lowered, I totter back to the edge of the bed, the squeaking of the plastic panties a constant soul crushing accompaniment, the teasing of the plug a source of terrible and inescapable arousal.

  At the bed, I perform another bob curtsey and stand with my hands behind my back before Mother. I stare down at the floor and await instructions.

  I know that Mother is studying me as she pulls the breakfast tray onto her lap. I know she is considering my bizarre, ultra-feminised form with her lovely honey brown eyes. I know that she is wearing a semi-transparent white silk nightgown through which her astonishing body is clearly revealed.