SheMale Academy

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.

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-panelled shower unit. Above the washbasin is a very large, mirrored medicine cabinet. On the wall opposite the shower are rows of metal racks over which hang thick pink towels of various sizes.

He is pulled painfully into the centre of the bathroom. Miss Wilding then releases her terrible grip on his sex and turns to face him.

"You will learn that any form of resistance, however minor, will be severely punished. I will administer a more appropriate punishment later, but now Honey will prepare you for your meeting with Miss Lacey and the other senior staff."

With this, Miss Wilding turns and marches from the bathroom, her heels clicking against the gleaming tiled floor, Alan's eyes helplessly following her long, black hosed legs in their confident, sexy stride. Then he finds himself turning back to face the gorgeous spectacle of Honey. The lovely maid unleashes another helplessly sexy, shy smile and minces on her very high heels towards him.

"I better untie you, first, Alice."

Her voice is so sweet and gentle, the beautiful collision of a little girl's high pitched tones with the erotic cadence of a very sexy adult. Now he knows why she is called Honey.

As the gorgeous maid gently removes the bonds securing his body, he suddenly becomes acutely aware of his nakedness. For the first time since his arrival, embarrassment replaces fear and anger. As this beautiful young woman works his arms free, he blushes. As her large breasts press through the soft, teasing fabric of her beautiful, sexy dress against his back, he is overwhelmed with a bizarre mixture of humiliation and sexual excitement. And rather than try to escape once his arms and ankles are untied, he shyly covers his stiff sex with his hands.

"I'm going to remove the gag," Honey says. "If you scream out or try to run away, I will call for a mistress and you will be caught and severely punished. Escape is impossible anyway. We are in a sealed underground chamber, and the door to your room is controlled by a digital lock. Also, as you may have noticed, you’re naked."

He nods his understanding and Honey carefully pulls the thick strip of tape from his lips. She then pulls the panty gag from his mouth and he gasps with relief. She smiles and drops the panties and tape into a plastic bin under the washbasin.

He says nothing as she then orders him to step into the shower. Indeed, he finds himself quite meekly obeying her, his hands still covering his erection, his face covered in a hood of embarrassed crimson. For now, he can see little point in resisting. Also, this beautiful girl has a manner about her that very easily dilutes any thought of resistance.

"Use this to wash," she says, handing him a plastic bottle containing a pink coloured liquid. "Cover every inch of your body, including your face, pubes, under arms and between your buttocks. But don't, under any circumstance, put it on your hair or get it in your eyes."

She leans forward and turns the shower controller clockwise. A gentle stream of warm water splashes against his naked body and, after a moment's hesitation; he pours a puddle of the pink liquid into his hands and begins to rub it carefully over his body. Soon he has worked up a thick lather and, as ordered, proceeds to cover every inch of his body, including his pubes and between his legs. He then stands under the shower and lets the water wash away the thick, pink lather. As it does so, something totally unexpected happens: the thin layers of hair on his chest, arms and legs are washed away as well, and so, to his horror, is his pubic hair! Indeed, within a few very deeply disturbing seconds, Alan's body is completely hair free. Suddenly, his body is as silky smooth as a newborn baby’s, the only memory of his body hair a strange, yet not unpleasant tingling sensation.

Amazed, he turns towards Honey. "What's happened? Where's all my hair gone?"

"Be quiet," Honey snaps. "Now wash your face as ordered and then use the soap in the dish to wash away any lingering cream."

Despite his astonishment, he follows her instructions, quickly discovering that the bar of gold coloured soap gives off a very powerful feminine scent that only serves to increase his sense of humiliation and general emasculation. Yet despite this and despite the fact that every hair on his body and face have now been removed, he remains quite fiercely erect.

Once his body has been thoroughly soaped and soaked, he is given a small glass bottle and told to use the blue liquid within it to wash his hair. When his hair had been washed and rinsed, he is ordered to step from the shower. Sweet scented water trickling down his smooth, hairless body, poor Alan does as Honey instructs. The lovely maid then takes a large pink towel from one of the metal racks and wraps it tightly around his body. She then begins very gently to dry his body, her eyes darting shyly between the task in front of her and Alan's crimson face. As her hands massage him through the thick towel fabric, his eyes are drawn helplessly towards her splendid breasts. The maid's dress has been designed with a particularly plunging neckline and as Honey dries her charge, Alan receives a very fine view of these splendid pale rose orbs.

"You're very beautiful," he mumbles, helplessly brave words that seem to escape his mouth against his will.

She smiles briefly, girlishly, obviously delighted. "You mustn't talk, Alice. No maid can talk without a mistress’s permission."

"But you're talking."

"As a mentor, I am allowed the privilege of free speech, but only with my charge. And you must obey me. Now be quiet or I will gag you."

He obeys her, even as her long, elegant hands reach the part of the towel covering his rigid sex, and even as she quite deliberately caresses his sex through the towel.

"You've got a very big cock, Alice. But Mistress Holly tells me you've probably never used it."

As she teases him with these words, he fights to keep silent, despite the waves of anger and sexual hunger that crash over his body.

The towel is then removed in one swift, cruel gesture and, naked once again, he is led from the bathroom and back into the main bedroom area. Here he is made to stand before the closet doors and watch as Honey takes from inside a bizarre and disturbing collection of feminine attire, laying each item out carefully on the bed with an aroused smile.


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sissychelle

This sissy is with You now for off and on 3-4 years and slowly but surely she gets Your program and discovers her true nature. In the beginning she was just a sissy on occasion and at “certain” times. But… Read more “sissychelle”

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