New Style Dresses At St Eleanor's
Art and storyette by Prim

  Charles Mason was hauled into the sissies' dressing room by Marilyn Pinchworth. "Here he is, Miss Gusset. Ready for his new school dress."
  "Ow - Oooowwww!" squeaked the desperate youth, held by his ear. He was the senior of the twelve boys at St Eleanor's, having survived nearly two years of sissying. Miss Gusset knew his weaknesses well.
  "I've got just the dress for you, Mason. If you had been born a girl, your mother would have dressed you in pink satin, I am sure. So since you've lived up to her expectations and become the most girlish of them all, I'll put you in soft satin, only baby blue." She slid the dress off its hanger in sizzles of heavy satin. "You've got him in some lovely petticoats, Marilyn."
  "Thank you, Miss. Hear that, Sissy-Panties: Miss says you're a real little girl. Put your girlie hands into your dress sleeves... NOW!"
  "But it's a little girl's dress," whined their victim. "Please can I wear the same as we had last semester? Ooowww!"
  The wretched youth's ear was twisted another full turn, and he was enveloped in shimmering satin as the dress settled over his wide silk-chiffon petticoats. Marilyn stood behind him to fasten his dress down the back. His shame forced his feelings into words.
  "Please don't make me wear it," he gasped, horrifed at the swirls of pale blue satin that bounced on his petticoats, with frills all round the wide hem. "The girls will laugh at me. They laughed at our pink gingham frocks and white blouses before the vacation, so this will be far worse!"
  Miss Gusset stooped and delivered five or six smacks across his legs under his chiffon petticoats as Marilyn held him immovably for the purpose. "That's for lack of enthusiasm," explained the sissies' wardrobe mistress with tight lips. "I'd keep that mouth shut, if I were you, or I may be deciding to put you all into pretty Easter bonnets instead of satin hair ribbons."
  "Oh yes, Miss. That's a brill idea!" cried Marilyn, doing up the satin bow high on the back of his dress. "What do you think, Davinia?"
  Marilyn spoke to her friend who had arrived behind them with her sissy, Paisley Silcocks, who was dithering and sobbing in a wide set of silk organza petticoats. "That's a must, Miss Gusset," cried Davinia. "They've got to have pretty bonnets to go with these wide dresses, like as if they're all shepherdesses." She shook the wretched boy beside her by his elbow. "You want to be put into a bonnet, don't you, Silcocks?"
  "Well I... er..." and his head went dizzy with the shaking he was getting... "y-yes please, Miss Davinia."
  He was obliged to watch as the lace edged collar was turned up for Mason and fastened with a button and loop to ensure it stayed up round his face.
  "Twirl!" ordered Miss Gusset. "Can we see his ruffled panties all the time, Marilyn?"
  "Yes Miss, he'll do." There were pretty edges of white lace round every ruffle that fluttered round his bottom.
  "He's ready then," said Miss Gusset. She lifted his chin with one finger to speak eye to eye.
 " The girls are waiting in the senior girls' common room, Mason. You can go and show them the new dresses for our sissy boys. I have a feeling they'll want to tease your feminine little bit in those sweet girly panties."
  A big tear rolled down each sweetly made up cheek as Charles held his dress out sideways and gave a grateful curtsey. "Th-Thank you, Miss G-Gusset." As he was pulled towards the door in a sizzle of petticoats, Paisley Silcocks shuddered at the girlishness of Mason's dress. In just a few minutes, he would be dressed the same and taken back into a class of cruel girls who would see how pathetic he was going to look for the new semester. He was shaken from his fears by Miss Gusset's stern voice.

"Silcocks, my little wimp. I always knew who it was who was going to be in pink satin. Won't you be a prissy sissy?" and Davinia burst into giggles as the soft satin caressed his arms. She loved to see him cry when she and Miss Gusset were getting him dressed. Better still, she loved to see his sissy cockette dribbling its cum. Her fingers delved under his petticoats and held it while Miss Gusset pulled his dress together and buttoned him down his back.
  "No wonder you're blubbering, you little sweetie," said Miss Gusset with a giggle. "The girls in Upper Sixth will tell you how sweet and girly you look."
  Paisley's blubbering rose to little cries of helplessness as his cock grew more and more pleasurable, helped towards a long and shuddering climax by the practised fingers of his prefect guardian.
  "Don't overdo it, Davinia dear," said Miss Gusset with an understanding smile, "the other girls will want a turn when they see him in his new dress. I think the little wimp will be quite drained by home time."