Vernon Pollitt was widely viewed as a girlish boy. In the changing rooms the boys gathered round to see how small his cock was, and girls had photo-shopped photos of him wearing ribbons in his hair and hoop earrings dangling at his neck. It didn't help that his mother had his hair cut in a long, girly style, and when it was discovered - from one of his cousins - that he asked his mother every evening if he could wear her panties and slips, his fate was sealed. When the new term started, Jamie 'Pretty-boy' Welsh was released from his service, and it was a shoe-in for Vernon Pollitt to become the new School Sissy at the Lady Graceful Academy.
A letter arrived at the boy's home informing his mother of the Principal's choice. Amelia Pollitt wrote back admitting that she had wanted a daughter and was only too happy to see Vernon happily wearing her lingerie - and occasionally one of her satin blouses, a treat which inevitably saw his true sex betray itself in helpless surrender.
Principal Constance Hardcastle was delighted with Missus Pollitt's cooperative response. His uniforms would be sent home on the first day back, after her son had been dressed and presented to the school as their sissy on Monday Morning.
Meanwhile it would be best not to inform him: it had been known in the past for the new sissy to make a run for it, and was only dressed three days later after being caught and brought back in handcuffs.
Miss Hardcastle wasn't having that happen with Vernon Pollitt. Oh no. She had arranged for two of her most competent senior girls, Andrea Rankin and Head Girl Jennifer Sharpe, to join her in her study from 8 am on Monday morning, where she briefed them about intercepting him as he entered the school campus. They would tell him that Miss Hardcastle wanted to see him right away because he had won an award.
Vernon was accordingly brought to Miss Hardcastle, naturally nervous about being summoned to the Headmistress's office, but excited too. He was told to sit in the chair that faced her as she surveyed him across her desk.
"Good morning, Vernon," she intoned. "Well, what a special boy you are this morning, by popular acclaim."
Vernon had a sudden light-bulb moment. The English essay he had written for Miss Sweetning, whose blouses he dreamt about night and day, had sent her into ecstasy. She must have nominated him as star pupil of the month. His exhilaration was short-lived, though, when the girls seized an arm each and fastened his wrists with ribbons to the back of his chair. Miss Hardcastle watched with nose in the air and pursed lips until the girls were done.
"You know Jamie Welsh?" she said. "Well it seems he has fallen out of favour with our students at Lady Graceful."
The shock of this statement came at Vernon Pollitt like a sledge-hammer and he would have fainted on his chair if it hadn't been for Andrea with smelling salts and Jennifer standing behind him to cushion his face in her blouse sleeves as she cupped his chin in her hands and hugged him into her waist: "Sit still and listen to Miss," she said. "There's nothing you can do about it."
The Principal was calm and measured and kept her announcement brief. "The girls voted you in as School Sissy by seventy-five per cent. The boys voted for you unanimously."
Vernon Pollitt felt sick on realising what the boys would do to him. He remembered that unforgettable day when he'd seen Jamie Welsh held face down over the edge of a desk for four boys to take their pants down one after the other and stick their very stiff cocks into his ass. There was no complaint from that sissy because his face had been gagged and covered in his lacy panties.
"You will be brought into this morning's whole school assembly," explained the Principal, "wearing one of my blouses. You will then be dressed in your sissy uniform, and if I see your penis betraying sissy tendencies you will be punished."
Thereupon the two girls stripped him to the skin and opened the fussy blouse in oyster pink satin that Miss Hardcastle gave them. It buttoned down his back and had a feminine frill all round the shoulders, with pouffy sleeves and frills on the cuffs at his wrists. The new sissy blubbered with shame and fright as he stood between the girls to have his blouse plucked and fussed into shocking femininity. It just managed to cover his cock, which was aching with stiffness under the satin. The time had come for the elected sissy to be taken on stage for the morning assembly.
As he appeared in pink between Jennifer Sharpe and Andrea Rankin, the school burst into uproar. Luckily the smelling salts were still effective in preventing Vernon Pollitt losing all blood supply to his head, but it was a seering shock to him to see 300 students looking up at him and hearing thirty women staff laughing at him from the edges of the stage. Miss Hardcastle lifted her brows in contempt as he sank to her expectations by bursting into tears as she stood on stage in her cream blouse and chocolate pencil skirt, with light brown leather boots and a cane in her hands.
"Students of the Lady Graceful Academy, you see in front of you your own choice of school sissy. "She," and she paused on the word until the school's laughter had subsided, "will be known as Polly Pollitt. Jennifer and Andrea will now dress her in the new sissy uniform, and after that she will be on stage each morning for her sexless confession and to receive the laughter of the school. Girls."
Jennifer stood behind the sissy and undid his blouse, casting grins at the delighted audience below, while Andrea wheeled the sissy uniform in from behind the curtains. There was another roar of laughter at the items that swung from the rail.
They started with his suspender belt, in white satin with pink lace piping all round and six white suspenders with pink bows at the clips. His stockings were white and prettily decorated with lace at the welts, which the girls took some time clipping together with fine adjustments, turning Polly this way and that so that everyone could see that his pink seams were straight down the curves of his legs. They had such a cute pair of high heeled Mary Jane shoes in pink patent, which buttoned across his insteps twice in delicate straps.
Next came his bra: a long-line style in pink satin. "You'll have to move your hands," declared Jennifer in a hard voice. "How else can we put your hands through the straps of your brassiere, little girl?"
Vernon faced up to the inevitable and released his cock to comply with his superiors. Into everyone's view danced his unbelievable erection, bringing universal mayhem to the assembly. The noise shook even Miss Hardcastle, but she decided to let it go. The school had chosen him as their sissy and what was the good if they couldn't hurl mockery at his sexlessness?
Once he stood in his bra with his cock covered again, his breast forms had to be fitted inside. Should he defend himself from being so obviously feminized? Or should he hold onto his cock and protect his manhood from showing his deviant sexuality? The forms were slipped inside. But oh my God! They were so BIG! The school erupted again.
"Hands in!" ordered Andrea, and he had to uncover himself again for his petticoat, the first of three. It left his shoulders uncovered, but did not even reach his waist with the frilly layers that spread widely all round him. There was a second the same, then a third, bobbing and bouncing fluffily on top of each other as his bare arms sank into them. Over them he was to wear a little flared skirt in pink organza, the sort of skirt that would delight a little girl of three who dreamt of becoming a bellerina. The girls passed it round him between them, forming two tiers in a burst of feminine childishness, and it fastened down the back with three gorgeous pink bows in fuchsia pink satin. To the sissy's dismay it failed to cover his petticoat frills or even reach his hips, and rode even higher when they held its matching straps in ruffled satin, which they passed over his shoulders from front to back. They would go over his sissy school blouse.
It was Jennifer who unhooked his blouse from its hanger on the rail. Instead of bringing it to Polly Poppitt she wanted to show it to the whole school and walked along the stage apron to expose its delightful feminine features.
"What pretty puffed sleeves for Polly, what lovely frillies down the front, and what a sweet sissy collar edged with a pink frill. Oh Polly!" she exclaimed in a voice of mock excitement, "you're going to feel EVER so GIRLY wearing your School Sissy blouse."
Her audience loved it and laughed long and loud as she held the blouse high and turned it this way and that. But Andrea had a second treat for her audience, at Polly Poppitt's expense. It was his sissy panties, which she brought to the front too after okaying it with Miss Hardcastle.
"I know sissies," she said, "so I know that this sissy is going to be SO STIFF inside these lovely panties all day long. LOOK at the frills round these wide legs, and LOOK at these pink ribbons and bows. The panty is in the sweetest pink nylon, just like Polly wants them to be, isn't that right, Sweetie?"
Polly did not look enthralled. He was crying bitter tears, his face twisted in deepest misery as he tried his best to cover his reaction to the panties. Jennifer raised her hand, wanting silence in the hall and getting it. "Students," she cried, "it's time for you to be quiet and to listen. Listen to our sissy, who has a duty in front of the school assembly. Each day, while she is being dressed at assembly for the whole school, she will have to beg for some items of his uniform. And today, Polly Poppitt, you must beg us to dress you in your blouse - and in your panties."
The misery burst from his throat with twice the force as before as he grimaced with humiliation. There were some guffaws from the floor but they stopped and the whole school sat in wrapt attention, waiting for the School Sissy to ask the girls to complete his shame.
Vernon Pollitt struggled over the space of thirty seconds to control the sobs and choking that prevented his words. He was met with thinly disguised impatience from Jennifer Sharpe, who held his blouse across her skirt with a hand on each hip - but she could see he was trying to speak, desperately, since his only route to leaving this stage was to get himself fully dressed in his shocking uniform.
He overcame the convulsions in his stomach and lungs and mumbled what he had to in a hoarse, struggling voice.
"What's that, Polly? We can't hear you."
"P-Please Jennifer, will you d-d-dress me in my blouse?" he whimpered.
Jennifer snorted, dissatisfied. "Do you mean this little girl's blouse, with pretty frills, and the cutest pouffy sleeves at the shoulders?"
"Y-Yes, Miss Jennifer."
"Then SAY so and stop trying to annoy me!"
Vernon was so alarmed he forgot about his erection and clutched his cheeks in both hands. A ripple of laughter crossed the hall but fell away so that everyone could hear the crimson-faced sissy.
"Oh please - please Miss Jennifer, I want to wear my little girl blouse, with lovely frillies, and I want to have pretty pouffy blouse sleeves at my shoulders. Pleeeease!"
More laughter burst out, but it was mixed with ironic "Aaahhhhhs!" of sympathy for a sissy who so wanted to look like a sweet little girl.
"So now you need to ask for your panties," announced Andrea on the other side of the sissy. "I know you want to wear them - because your mother has told Miss Hardcastle that you ask her every night if you can wear her panties and feel like a girl. Isn't that right?"
Vernon Pollitt squirmed on the spot, boring the toe of one Mary Jane shoe into the stage.
"WELL?" demanded Andrea. "What do you ask her each night?"
Everyone could see how Vernon Pollitt wilted before their eyes, his hands over his aching erection, and summoned the courage to spit it out. "I - ohhhhh! - I ask Mommy - oh dear! - I ask Mommy if I can wear a selection of her prettiest silk and satin panties, Miss Andrea. Ohhh" boo - hoo - hoooo!"
The audience was inclined to stay silent, hardly believing their ears but enjoying every moment of the interrogation. Andrea dropped her chin onto her school tie and eyed the sissy, clearly expecting the obvious. "So what should you ask me now, Sissy?"
His voice was more sniffles and sobs than words, but his meaning was clear. "I want to wear my lovely sissy panties, Miss Andrea. They are so sweet and sissy - in pink satin and lace - with the cutest ribbons and frills round - round - all round the legs, ohhh! Boo - hoo - hoooo!"
"What we need then," said Jennifer, "is for you to reach out to your sweet little girl blouse and your frilly panties - with all your heart for us." She and her friend held the items in the air inviting him to get them.
The two girls suspected what was inevitable. As Vernon reached for his uniform - and as the girls held them just near enough for him to feel how silky and girly they were - his uncovered stiffie did everything that was expected of it, and to the squeals of his audience, Polly Poppitt shot uncontrolled squirts of his sissy jism high into the air above the school stage.
The pandemonium lasted as long as his ejaculations shot up and rained down, which was a long time, and by then, Miss Hardcastle was on her feet with her cane in her hands.
"Girls," she cried, motioning the school to calm down as all eyes watched the shameful crying and squirming of their well-chosen sissy. "Before I punish this boy for his dis-GRACE-ful exhibition of sexlessness, is there anything you want to add about this sissy?"
"Yes," said Andrea: "If any girls want to help do his hair with Jen and me at morning break they're welcome to join us: we'd love a hand and a good audience too."
"I think," said Jennifer, "he's got a pretty face and such lovely - succulent - lips: don't you agree, boys? It wouldn't be right to let them go to waste!"
There was no answer from the boys, but all round the hall trouser flies were already straining with the pressure of pounding hard-ons. The new school sissy, once he was wearing his full School Sissy uniform, had better stay amongst the girls, no matter how pitilessly they teased him, because otherwise he would not be able to keep hold of his pink nylon frilly sissy panties.
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