Sissy of the Month
by Prim

Chrissy Phillips sat nervously in the college foyer, thankful that none of the guys or girls were passing through to see him in college with his Mom beside him. There was something worrying about how the message had arrived halfway through a psychology class, to say he was to go home and return immediately with his Mom. What could Miss Evergreen possibly want her at Marion Churning High School for? He was pretty sure he hadn't done anything to win recognition. Winning prizes was not one of his strong points. Then the Principal's secretary appeared. Could they come in and see Miss Evergreen now? Chrissy's knees were like jelly as he followed his Mom and took his place beside her, looking across the desk at the Head. Miss Evergreen, who had been in charge since before most of the staff were born, pursed her crimson lips and peered at him with eyelashes almost closed. Then she lifted a little brass bell on her table and gave it a short ring.
Side doors opened to left and right to admit girls - more and more girls, until the room had twenty girls at least standing all round them, with Chrissy in the middle, feeling as if he had been shaken and stirred. His mom seemed perfectly okay, as if there were to be no big revelations to cause her the slightest concern. Silence fell in the packed office, and all eyes rested on Miss Evergreen. Her voice was filled with authority, yet strangely quiet. It made everyone listen hard.
"I understand you want to be a girl."
Chrissy jumped, as if stabbed in the chest. She was talking to him. His blood drained from his head, making his shake of denial a very weak one. Miss Evergreen turned an inquiring look on his mom, and Chrissy turned to her as well.
"He likes me to put him into little girl panties and petticoats," she said, turning to him, "and sometimes I let him wear my bra, suspenders and stockings." She used a gloved hand to brush his hair softly back from his whitened forehead. "And my high heeled court shoes. He likes those."
Chrissy just caught sight of the gob-smacked surprise on a couple of girls' faces before his eyes rolled up and he passed out.

When he woke, he was lying on the bed in the medical room, with Connie Jenson and Faith Atkins looking down at him, their lipstick and pure white teeth grinning with contempt. And Chelsea Burrows was there too, and Millie Worthington, Anne Watts, Delia Van Delvt and loads of others. They burst out giggling when they saw he was coming round.
They had a mirror, which they held above him to see himself. Ohhhh, what had they done? He was wearing make-up, and his hair - what had they done to it? And what was that all round his head. Millie Worthington got hold of it and pulled it round both sides of his face, in a tall, frilled collar of stiffened organza.
"Do you like your assembly blouse, Sweetie? You're on in two minutes, Miss Evergreen said so."
Chrissy tried to get up but his legs felt constrained - and yet somehow bare and exposed. A dozen girls' hands helped to lift him up and turn him so that his feet could find the floor. He had a frightening feeling that his cock might be erect, and looked down to see. Aaarghhh! It was in girls' white pantyhose, and was growing more and more stiff in front of him. He tried to deliver himself from all these hands, but the girls had other ideas as they parted in front of him and revealed Amanda Bracewell approaching him with - oh no! - with a girls' ballet tutu in her hands, which she opened out with its ribbons. The desperate boy was held still to be put into his dance skirt, amid splutters and raspberries of the girls' derision. It was done into a bow at the back of his waist, and Chrissy burst into loud tears of pleading, begging - imploring the girls to undress him and let him -
Then Miss Netting opened the door with an announcement: "Miss Evergreen is ready for him now. Four of you, bring him onto the stage."
Ahead of him, Chrissy heard tumultuous applause, while he was led through the wings. He saw his mom, beaming with satisfaction, drinking up the applause of the whole school. The Headmistress was with her, then turned to face Chrissy as he was bundled into sight, his stiffened tutu flicking up and down around him on all sides, his legs defenceless and his organza blouse surrounding his crimson cheeks and girlish hair. He saw his mom beaming at him. She was delighted, all smiles. Then Miss Evergreen lifted her gloved hand to establish silence. Her eyes turned to Chrissy, who was held in front of her by four girls, holding him angled to face the hall full of students.
"Chrissy Phillips, your penis shows extreme arousal, as if ready to ejaculate." The boy almost fainted again, then he felt her fingers on the erection in his pantyhose. It focused him on what she went on to say. "Do you feel sweet and girlish in your assembly blouse and dance skirt?"
Chrissy didn't know what he was saying, but it was a mixture of 'yesses' and 'oh pleases'.
"I thought so, Sweetie. I am selecting you as Sissy of the Month for the Marion Churning High School."
Her words were met with torrents of applause from every girl in the hall. The boys clapped too, but only to avoid drawing attention to themselves.
"I can assure you, Miss Evergreen," his mom was announcing, "I will have him as a sissy from now on. How lovely that he will have ballet classes instead of his previous academic course."
The Head smiled, her eyes closed with blissful pleasure. Miss Netting passed her his prize, which Miss Evergreen delivered from its tissue packaging. A storm of girls' laughter erupted, and Chrissy fainted again, this time held up in a half collapsed condition by his four guardians. A phallic plug, larger than a wrestler's, caught the light on its shiny pink rubber helmet, as the Head gave her instructions.

Chrissy was turned over in the grip of the girls, to reveal the stretched white panty of his hose and the access slot between his cheeks. To the amazement of every girl watching, Miss Evergreen herself crouched in her high heels at the boy's feet, to feed one satin loop, then the other, over his ballet pumps. She drew them and their rubber implement up his pantyhose, in spite of his clenched knees, until the loops fitted snugly at the very tops of his legs. Miss Netting administered a slub of jelly, pushing it through the gap in his pantyhose and inside the boy's slot with her fingers - then a hush fell on every soul in Marion Churning as Miss Evergreen carefully planted the helmet at the glistening niche of the upturned bottom.
Every ear in the school heard the wail of sissified submission from the firmly held organza blouse, as inch by inch, the cock sank deep into its home. Then Chrissy Phillips, red and weeping, was turned to face the school as she drew the pink satin belt round his waist and secured it through its buckle, before his tutu was dropped again and fussed by her and her girls until he was properly dressed, in blouse, dancing skirt and sissy cock-plug. It only remained for an enormous bouquet of blooms to be presented to Missus Phillips, and the assembly was then allowed to enjoy quarter of an hour of hilarious laughter and applause as the new sissy was paraded with dainty steps from one side of the stage to the other and back again by his blissfully happy mother.