Sissy Academy Story

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Sissy Academy Story

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The sissy academy is based on 12 sissy rules you have to obey at all times. These rules set a base to your devotion to being a sissy. And breaking the rules means disobedience. Explore the academy there is so much to do for sissies like you!
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As the van moves slowly and anonymously through dense city traffic, its carefully and very tightly restrained cargo struggles angrily and squeals with increasing desperation into his soft but highly effective panty gag. Alan, soon to be Alice, lies face down on a leather bench bolted to the floor of the van. His slender, always girlish frame is sealed from neck to toe in a tight, figure hugging cocoon of pink rubber and thick leather straps hold his body in place at the ankles, thighs, back and neck. Beneath the rubber, he is naked, his arms lashed painfully behind his back at the elbows and wrists, his ankles also tied tightly together. Large, fearful tears trickle from his baby blue eyes, over his flushed, gag-expanded cheeks and across the thick strip of silver masking tape holding the panties firmly in place.
Poor Alan’s useless struggles are hidden from view by carefully blacked out rear windows and a thick metal partition that separates the storage area from the driver and passenger’s seats. He knows that Miss Lord and his Aunt are sitting on the other side of the partition, and he also knows that they are taking him, completely against his will (yet with the absolute agreement of his mother), to the Lacy Academy for Young Ladies. Here, he is to be subject to a strict regime of enforced feminization, to be transformed into a demure, submissive and utterly convincing she-male maidservant.
When his training is complete, he is to be returned to serve his beautiful, long suffering mother, Mary, and his elder sisters, Miriam and Stephanie. Then Alan will truly become Alice; his bold, brash and arrogant male self will be destroyed and replaced with the dainty, ultra-feminine personality of a sissy slave girl.
This strange future had been described to him only an hour before by his gorgeous and very determined Aunt Holly. Awaking from the effects of a drugged cup of tea, he had discovered himself on the living room floor, naked, bound hand and foot and tightly panty gagged. As he had struggled before his Aunt’s high-heeled feet, she had revealed his fate with a cruel smile.
“Put simply, Alan, your mother, your sisters and I have had enough of you. And this business with the police is truly the last straw. How a young man who has had your opportunities and privileges can end up spending a night in a police cell for being drunk and disorderly… well, it defies belief. It also exceeds the limits of your mother’s patience. Since your fifteenth birthday, you’ve brought her nothing but trouble and embarrassment; she’s had to put up with a year of masculine insanity, most of which can be put down to physiological and social conditioning. Well, it’s about time we reserved that conditioning. And it just so happens, I know someone who can do this very effectively.”
As he had struggled, as tears had begun to pour from his eyes, Aunt Holly told him of her close friend Angeline Lacey, the headmistress of a very special and very secret school for wayward young men; a strange, awful place where the delinquent sons of the rich and powerful were sent to undergo a radical and permanent transformation into pretty, subservient she-males, she-males who were in terms of their physical appearance, dress and manner ultra-female, yet who remained, in most cases, biologically male. Petticoated males, who were carefully conditioned to look and act like the most extreme sissies imaginable. As a pupil at Miss Lacey’s school, Alan would be transformed into Alice, a lovely, mincing maidservant whose only desires would be to revel in her extremely delicate and increasingly radical feminization and to serve her mistresses in any way they required.
As Aunt Holly had revealed his terrible fate with a widening smile, Alan had tried to avoid staring at her long, black nylon sheathed legs towering above over him. As this gorgeous, brown eyed brunette, the subject of so may of his teenage fantasies, pronounced his fate like a Greek goddess, he had squealed his outrage and rolled over to face his mother, his eyes pleading uselessly for mercy and release.
His mother was slightly shorter than Aunt Holly, but just as beautiful. His only parent since a bitter divorce ten years previously, Alan had grown up loving her with an almost unnatural passion. Yet in the last year, this love had been ruined by a series of mindless acts, acts inspired by a group of very rowdy, aggressive friends. He had suddenly changed from a mild mannered mother’s boy into a genuine terror, bringing shame and bitter disruption to the family home.
Following her teasing description of his fate, Aunt Holly had, with his mother’s disturbingly eager assistance, forced his bound body into the rubber bag, sealing him inside with a wicked, vengeful smile as had he squealed and cried. Then, to his horror and utter humiliation, as the bag was pulled over his long, girlish legs, his exposed penis had suddenly become erect.
“Well,” Aunt Holly had whispered, “you’re obviously not as upset as you sound. Maybe it’s the taste of my soiled panties.”
Once he had been tightly ‘bagged up’, Aunt Holly had left the living room. His mother had then knelt down at his side and used a scented hanky to swipe the sweat from his flushed, tear soaked face.
“It’s for your own good, Alan. Holly assures me you’ll be far happier as Alice. And it will be so nice to have a sweet, obedient daughter.”
His squeals lessened as his mother had mopped his brow. Dressed in a beautiful cream silk blouse, short black skirt and matching hose, her own high-heeled mules glistening in the bright summer daylight only inches from his tightly bound body, she had been a vision of mature beauty, another striking brunette with a superb figure which his guilty eyes had fought to avoid. Her strong, rose scented perfume had tickled his nostrils and brought back a hundred sinful memories of his helpless attraction to her. Her golden brown eyes had held both a mother’s concern and her own definite arousal. He had felt as his sex strain harder in its sinister rubber prison as his eyes were pulled towards her long, black stockinged legs. As she knelt beside him, her skirt had risen up to reveal the dark tips of her shapely upper thighs and a hint of blood red silk panties. Then he had found his terror and outrage crushed by a very familiar and awful shame, and he knew it was this perverse need that had driven him into the hands of the police, that his behaviour over the past year had not just been the rage of a testosterone fuelled boy, but the reaction of a suddenly sexually aware youth to the simple fact that he desired his own mother. And as this desire had returned, as he had wiggled helplessly before her, he had found himself thinking, if only briefly, that perhaps feminization was the most suitable punishment for such a dark lust.
His eyes had then met hers and she had smiled. He had fallen still. She had taken his head in her hands. Suddenly, his bonds had not felt so terrible and he found himself moaning with a weird girlish pleasure into the inescapable gag, a pleasure in his helplessness and in his intimate, complete possession by his lovely mother. Then, suddenly, Aunt Holly had strolled back into the room and Alan almost immediately resumed his ballet of squeals and wiggles.
Accompanying his Aunt was a very tall and very beautiful blonde woman, a complete stranger who regarded the naked, tormented Alan with a grim smile of contempt. Dressed in a skin tight black sweater, equally tight Lycra leggings and a pair of running shoes, her striking blonde hair bound in a tight bun, she had seemed a particularly athletic figure and very much prepared for physical exercise.
“We’ll get him into the van and be off,” his Aunt had then announced. “It’s best we don’t hang around.”
The blonde had then grabbed his cocooned feet and Aunt Holly had taken his shoulders. Despite his struggles, they had lifted his slight frame into the air with little effort and carried him squealing from the room.
“Say hello to Alice, Beverly,” Aunt Holly had said to the blonde as they marched out into the sheltered forecourt of his mother’s large, suburban house.
“Hello, Alice,” the blonde had responded, her ice blue eyes filled with a wicked amusement. “I’m Beverly Lord, a teacher at Miss Lacey’s establishment.”
Then they had carefully loaded him into the waiting transit van and very tightly strapped him down, his continued wiggles and squeals earning two very hard and painful slaps on his rubber-sheathed backside from Miss Lord. And as the rear doors had been closed and locked, plunging Alan into a shadowy, echoing darkness, a sense of absolute doom had washed over him.
Now, less than sixty minutes later, as the van progresses through city traffic and moves onto the main road out of the city, the taste of Aunt Holly’s soiled panties, the pungent taste of her most intimate regions, fill his mouth and seem to seep as a delicate sex scent from behind the thick tape sealing his lips and flood into his desperately flaring nostrils. Despite his fear and panic, he is still very erect, and visions of his lovely Aunt and her gorgeous sister frame every angry but useless struggle against this awful bondage. Yet despite this bizarre arousal, and maybe because of it, his sense of doom is even stronger.
The journey to Miss Lacey’s Academy takes maybe another hour. During this time, poor Alan’s struggles are whittled down to helpless, angry breathing through the fat, pungent gag and the odd futile attempt to strain against the straps holding him so tightly in place. Throughout the journey, he finds himself repeatedly recalling his naked, tethered struggles before his lovely, teasing Aunt. Aunt Holly: a woman he has always found it much easier to desire. Her confident, dominant manner has always intimidated; yet it has also secretly excited him. His erection is therefore still in full effect by the time the van suddenly slows and stops. There is the briefest pause and then, after a sharp left turn, the van is moving again, but this time down a much bumpier road. This second part of the journey takes maybe fifteen minutes. The quality of the road worsens and soon poor Alan is shaken uncomfortably in the leather restraints. Then, quite suddenly, the bouncing stops. The van now seems to be on a much smoother roadway, and after only a few minutes it stops again. The front doors are opened and then slammed shut. He hears voices. His heart pounding with terror, he squeals desperately into the gag. The rear doors are unlocked and afternoon sun light suddenly floods the rear compartment.
“Welcome to Miss Lacey’s Academy for Young Ladies, Alice: your new home.”
This is Miss Lord’s voice. He hears her climb into the van and then feels her hands removing the straps. Then somebody else enters the van. As Miss Lord helps free Alan, it becomes clear the second person is Aunt Holly. And with her help, Miss Lord turns a numbed, stunned Alan over and the two women then carry him carefully from the van and into a large stone tiled forecourt which appears surrounded by a huge, ancient wood.
The two women then load him face down onto a leather-backed, hospital style trolley and use more leather straps to hold him in place. He is then wheeled towards a very large, very old house, which rises out of the wood like some strange creation of nature, a vast mansion designed in the Victorian Gothic style with a huge, arched entrance. And standing beneath this entrance he can see three figures.
As they move closer, Alan, now moaning fearfully into the gag, sees that the three figures are women, two dressed in very formal, dark business suits and one in a very striking French maid’s uniform.
One of the women steps forward exactly as Alan is wheeled under the archway. She is a tall, very beautiful redhead, in her early 40s. Her emerald green eyes peer down at helpless, fearful and now deeply embarrassed Alan, eyes filled with a very unsettling hostility towards the rubberised youth.
“She is to be taken to room 20,” the redheaded woman says, her clipped, Celtic voice failing to disguise her contempt for the expertly trussed male.
“Miss Wilding and Honey will deal with him from there.’
The striking woman then turns towards Aunt Holly. “Mistress Angeline would like to talk to you immediately.”
The second suited woman, a smaller, plumper blonde then steps forward and takes control of the trolley. His Aunt and the redheaded woman then begin a whispered and clearly strained conversation. Miss Lord and the blonde, who Alan now realises is Miss Wilding, push Alan into the house, followed very closely by the beautiful, delicately mincing maid, whose own very pale blue eyes remain pinned with an intense fascination on Alan’s tethered, rubberised form.
Soon they are in a huge hallway, and the sound of the women’s high heels echo against the marble floor, striking up a sharp, percussive rhythm that fills the unfortunate youth with an even greater dread. He notices a huge winding staircase to his left, yet the two women, followed by the maid, carry him off down a secluded and very dark corridor, at the end of which appears to be a large black metal doorway. As they approach the door, it suddenly slides open to reveal an elevator car!
Amazed and appalled, Alan squeals fearfully into his fat panty gag as he is carried inside the car. The maid enters behind them and then uses one of her white satin-gloved fingers to press a button on a wall panel and the metal door slides shut. A sickening feeling grips Alan’s stomach as the lift then suddenly begins a sharp descent.
They descend into this unknown abyss for only a few seconds before the car gently glides to a halt. The door slides open and he is wheeled out into a very bright, white walled corridor. Ahead, he can see the ceiling, along which runs a powerful white neon strip light. As he is pushed down the corridor, he also notices that the walls on either side of the corridor are lined with numbered pink doors.
Eventually, they arrive at room 20. His lovely bearers draw to a halt by the door and the maid minces forward to open it. Alan is then wheeled inside.
The room on the other side is surprisingly large. Each of the four walls is painted the same shade of pink as the door. A thick white carpet is spread across the floor. Against the nearest wall is a very large, very ornate white dressing table with a striking oval mirror. By the dressing table is a further, full sized mirror on a separate wooden stand, and next to the mirror is set of white wooden doors that seem to be the entrance to a walk-in closet. A little further down from the closet is another white door.
Along the far wall there are bookshelves filled with books and magazines and a few feet away from the shelves, there is an exercise bike. Just beyond the exercise bike is a single bed covered in beautiful white silk sheets. The only seat in the room is a pink leather backed stool placed beneath the dressing table.
Alan squeals as the women then release the leather straps and carry him over to the bed, where he is very carefully set down. His hot, flushed, tear stained cheeks press against the soft white silk sheets and his two bearers begin to remove the body bag. Soon, his sweat soaked and totally naked body is exposed to the relatively cool air of the room and a sense of infinite relief washes over him. Numb and aching all over, he is then pulled slowly to his bound feet and made to stand somewhat precariously in front of Miss Wilding.
“I am Miss Wilding,” she announces, as Miss Lord, after exchanging a dark smile with her lovely colleague, leaves the room.
Miss Wilding’s crystal blue eyes sparkle with a cruel amusement, her large, firm breasts rise and fall with a mixture of physical effort and sexual arousal.
“I will be your personal tutor,” she says, “and as such will be in overall charge of your feminization.”
His only response to this strange announcement is an angry squeal into the gag and an equally outraged shake of his head.
“This is Honey,” Miss Wilding continues, turning to the lovely maid, who then minces forward and performs a deep curtsey before Alan. “She is a newly qualified Graduate Maid and will act as my assistant. She will also be your Sissy Mentor.”
It is only now that Alan begins, almost helplessly, to study his captors in more detail. Miss Wilding is maybe 25, of medium height, with a pleasantly plump, yet very shapely figure. Like Miss Lord, she wears her hair in a tight bun. Her suit, which appears to be some kind of instructor’s uniform, consists of a dark blue jacket, a white blouse and a matching, dark blue mini-skirt, which displays her surprisingly long and black hosed legs to perfection. Black patent leather, high-heeled court shoes add a final touch of formal glamour.
Miss Wilding’s assistant, Honey, is younger, surely no more than eighteen. A tall, very buxom blonde, she is simply stunning. Her thick, very long hair has been tied in a pretty ponytail with a gleaming red silk ribbon and travels her perfectly shaped back down to the base of her spine. Her face is carefully and erotically made up. She has very long, curving eyebrows and equally long, helplessly fluttering eyelashes that perfectly complement her large blue eyes. Her full, pouting lips are painted a dark cherry red, which matches exactly her long glistening fingernails. Around her slender, pale neck is a simple, black velvet choker with a glistening emerald centrepiece. Her maid’s dress is cut from the finest black silk and beautifully trimmed with expensive cream lace at the plunging neckline, long sleeves and very short skirt. Her large, pale rose breasts seem to be heaving with some considerable excitement beneath the tight folds of the dress, over which is positioned a lovely cream silk pinafore tied at her back in a huge bow. The very short skirt of the dress rests on a mountain of lace froufrou petticoating, out of which emerge two perfectly shaped and very long legs sheathed in seamed black nylons, which lead down to a pair of stiletto heeled, open toed mules.
Alan stares at her in amazement and his sex is soon very obviously responding to this tremendously sexy dream girl. Miss Lord giggles and Honey smiles shyly. Then her lovely blue eyes meet Alan’s and he recognises an unmistakable look of desire.
“I’m glad you like Honey, Alice,” Miss Wilding teases, suddenly stepping forward and grabbing Alan’s exposed, erect sex, “because she’s responsible for supervising all your dress and make up requirements, and for your body hygiene.”
Alan squeals in horror as Miss Wilding’s cool hand wraps around his sex. He struggles furiously, trying to pull himself free of Miss Wilding’s tight, painful grasp. Her response to this resistance is to administer a very hard slap to his face and pull him forward by his tormented cock.
His ankles still tightly bound, his head spinning from the slap, he is forced to hop pathetically behind Miss Wilding. Honey then steps forward and opens the single white door just beyond the closet to reveal a small, pink tiled bathroom, which consists of a simple marble wash basin, a toilet and a glass-panelle
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