Prissy's Sissies
Drawing by Prissy and storyette by Prim

  The New School Sissies

  Office Sissies

  There is a heart-swooning fragrance of perfume in the Principal's office as Jack Dressiter and Paul Pantswell fuss out their petticoat lace into full circles around them. "Use the very tips of your fingers to hold your lace, Jack," says Miss Morgan, her scarlet lips pursed in the air so that she looks down at him through the bottoms of her spectacles. "See how Paul curls his fingers daintily while fussing and tucking with just his thumb and first finger... like a true girl."
A gush of warm delight floods through Jack and Paul at her words. They would do anything to please Principal Morgan. Unlike other pupils at the Westerton Finishing School, they didn't see her as a pitiless tyrant who picked on boys she didn't like. She was widely regarded as attractive for her age - indeed, her staff and pupils had to pinch themselves to be sure it wasn't Sarah Palin they were talking to, but you had to watch the movement of her smooth, slightly sharp chin: when it began to work a little as if she were chewing, the lash of her tongue was sure to follow. Jack and Paul had dreaded her like everyone else when she took over the school... until last Monday. That was when she summoned them to her study and dropped the bombshell- that she had chosen them, out of the most delicate boys in school to become her two school sissies.
Their training had started immediately, with both boys being fastened into individual desk-and-chair units and a pretty girls' dress being stood in front of each of them, hanging on a dress stand. Their first essay title was: What a lovely dress and why I want to wear it like a girl. Then one by one, Miss Morgan gave her new sissies a hot, sudsy bath.
That steaming, perfumed water was the signal for both boys to regard Principal Morgan as the dominant figure of their lives, since they were overwhelmed by the deep, sweet feelings that were so new to them. Miss Morgan herself was surprised by how quickly her two senior boys had taken to their new role. And now a glossy smile worked on her lips as she watched the boys work their fingers round every ruffle of lace on each of their billowing petticoats - becoming more and more besotted with their lovely, girlish apparel.
"Well done, Jack. The girlishness of your petticoats and dress is changing your nature. You have such dainty hand movements and your dresses are shaping your legs wonderfuly."
A thrill shook Jack Dressiter from his newly permed hair to his lilac dancing shoes. Miss Morgan was pleased with him and he wanted to please her sooo much. Then his friend Paul opened his mouth and spoilt everything.
"Miss Morgan, I know we have dress appreciation work to do with you this afternoon, but... this is Wednesday and we've got a socer match."
Jack's heart dropped like a cannon ball. Oh no! They might have to change!
"Jack and I are in the team, Miss Morgan: its a vital match... against Overmere High! I think we had better get our kit on. The guys will be waiting for us."
Miss Morgan rose to her full height and her lips pursed with authority. "Paul, you look lovely in your Wednesday dress... the result of sitting obediently with your panties on a pink cushion. You know perfectly well that you and Jack are to wear your feminising dresses for three hours each afternoon. That is how boys learn to be sweetly-shy and dainty. Otherwise I will not be able to call you my school sissies."
Both boys went white in the face. It took only three seconds for their minds to be made up. "Jack, we'll have to go out and play the game in our dresses. We must do what Miss Morgan says."
Jack's fingers continued fondling the lovely lace around his petticoats. For a fleeting moment, he wanted to show how lovely his petticoats were to the guys in the football team. When they saw the beautiful lace and the ruffled elastic of his panties, they would surely understand why he loved Miss Morgan to dress him this way. His thoughts were interrupted by the Principal.
"I have two lovely girls' coats for you to wear, boys. Here you are Paul: yours is in white wool with satin collar and cuffs. Isn't it pretty?"
The boy nearly swooned at how gorgeously its satin lining shone as she held it open for him to slot his hands into the sleeves.
"And o you like your coat, Jack? So sweet for one of my special school sissies."
The sting of tears welled at the back of Jack's eyes as he beheld the pale blue silk of his darling little matinee coat, which spread in wide pleats from a high yoke, giving his short dress plenty of movement so that all his petticoat frills would be seen bouncing and twirling as he ran about the field. Were they tears of shame, or the tears of a girl who is blessed with a wonderful new coat to go out in? Perhaps a bit of both.
"We must take care of your hair, Jack. This powder blue bonnet will protect your new perm." The Principal turned him towards her as she fed the satin onto the back of his blonde waves. He felt so delirious, looking at her beautiful lips which were definitely smiling. Oh rapture! She was pleased with him!
"And Paul, for you I've got this frilled bonnet in white taffeta with silk crepe all round the brim." As she fastened the silk ribbons under his chin he swelled with sweetness at how girlish the bonnet was. It stiffened his 'little popsie' into his display panties, spreading apart the sides of his dress and coat.
"I have an Active Feminism lesson with the senior girls now, my dears, but afterwards I'll bring them out to the field to see how girlish you both look while trying to be normal boys playing football."
The boys were walking on air as they left Miss Morgan's study and made their way with tingling hearts towards the sports changing rooms. Every girl they saw stared with disbelief then burst out laughing, and every boy felt their shame and shut up. The male pupils would rather stay out of the way in case Miss Morgan involved them in her 'modern teaching methods'. When Coach Mallins saw them at the door of the changing room he was temporarily lost for words, as the faces of the other members of the team peered past him to see.
"We need you guys," he said, hands on hips. "You'll have to play like that if she says so."
In the bustle and flurry of the game, it wasn't easy seeing what to do round the wide brim of a little- girl bonnet, and Paul lost his dainty slipper twice in the mud. The cheers from the ever-swelling crowd on the touchline gave the home side a huge lift, especially when the wind blew Jack's petticoats over his head and revealed his lilac rhumba panties. When one of the Overmere guys tripped him and stood over him with a mouthful of scorn and laughter, he was soon surrounded by irate players in the navy blue of Westerton... ... so that when play resumed, the bully was revealed in a heap in the mud, his groin apparently suffering severe cramp.
Miss Morgan smiled from the touchline. Her timing had been perfect: the two of them accepted their role completely, and had it in them to bond the boys and girls of Westerton. As the game neared its close, she was not in the least surprised to see her sissy Jack skipping girlishly up to the goal just in time to gently tap the ball into the goal with the lilac patent toe of his Mary Jane shoe?
Victory! Pandemonium! Topped off by feminine hand and arm movements by her two sissies as they tripped across the grass with delight to give each other a dainty sissy kiss.
Perhaps not quite so dainty, for as the team surrounded them with cheers and led them across the field to Miss Morgan, their bright red lipstick was a smudgy mess. "Three cheers for Miss Morgan," came the cry, followed by: "Three cheers for Jackie and Polly".
The names stuck, as did half the mud from the football field, on Jackie's blue silk coat and on Polly's stockings respectively. They would have to be spanked for not taking care of their girly clothes... but the Principal was fond of spanking sissy bottoms, and she would find many more pretexts for spankings as the semester continued to provide stimulating opertunities to practise her 'petticoat theory' of schooling boys.