The new sissy stood barefoot; naked but for the soft white gown. Though bewildered and a little scared, her little cock poked forward in the gown, partly through fear and partly through excitement as she felt the eyes of the stern woman upon her. Clara Bow rose slowly from the leather chair she sat in, cane in one hand, she wagged a finger summoning Pepper forward. She was accompanied by the buxom Nurse Wykett; her ample buttocks and breast bulging in her white uniform, her black stockings and stilettos a far cry from the usual sensible shoe preferred by most in her profession. Mistress Bow... Continue»
Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his anus tingled and gripped the soft rubber plug she’d also chosen for his first day. His stepmother had allowed his soft ginger hair to grow to shoulder length already, and his dosage of hormones had been already been increased. He had been suitably attired in a gingham dress with pink socks and red sandals; a pink bow in his hair to make him feel extra girly. Stepmother sneered with delight as she saw him adjust his little bra which contained his rudimentary breasts, as the great front door of the house swung open like a prison gate.
“If you think you’re girly now, just wait until you’ve had six months here; I will have seemed like a fairy godmother compared to the treatment you’ll receive here. Clara Bow and her associates will cane the boy from you forever.” Tears welled up as a stern looking woman with hair in a bun, tight pencil skirt, cane in hand, marched out from the house wearing an equally stern expression. She was accompanied by a young lady of about 18 who looked equally strict, and a pretty fluffily dressed girl of about Peter’s age. They stepped out from the car and the assertive looking woman eyed the new internee up and down with contempt before addressing Stepmother.
“You must be Ms Penderton, and this pretty girl must be Peter.” The stern girl giggled audibly as the sissy squirmed in discomfort at this immediate humiliation; now everyone present was assured he would be put firmly in his place. Stepmother smiled wickedly.
“Oh no, from this day onwards, this is ‘Pepper Penderton’; I trust that your academy will ensure she is the perfect lady when I next come to see her.” Pepper’s cock was rigid as she eyed the wicked cane the woman carried; she thought how it would stripe her soft bottom so much easier than Stepmother’s, it was much more vicious than ay cane she’d had used on her. The stern girl gripped Pepper’s hand like a vice as the fluffy girl carried her case from the car; Stepmother smiled and quickly drove off as though she had simply dropped her off at the shopping mall or day school; she would not see Pepper again for several months.
Pepper’s ass tingled about the plug as she watched the car disappear through the gates, which closed with clang as if to confirm entrapment, and the stern girl’s grip tightened on her delicate little hand. Clara Bow smiled with satisfaction and flexed her cane as she saw the bewilderment on the new sissy’s face. She turned to the fluffily dressed girl who held Pepper’s case.
“Lead your new friend to the dorm Tomkins. Grace, ensure our new girl is gowned and brought to see Nurse Wykett and I for inspection as soon as her things are placed.” The stern woman strutted off, her mature pussy swelling at the thought of inspecting the new sissy; it always gave her a thrill, the promise of a new bottom to cane, another male to feminise completely. She so loved to cane sissies to complete submission; the guardians who left their transgendered wards in her keeping, were glad to be shot of them and cared little about their treatment. Clara Bow was very popular woman with certain sections of the community; many a sissy was introduced to extra-curricular activities with such people.
High in a tree overlooking the academy beyond the wall, Bruce Janner grunted with pleasure as his stiff cock sent loops of white semen sailing over the wall. The tree waved precariously in the breeze as he held a branch for dear life whilst working his cock urgently with the other. Bruce loved sissies; especially ginger ones. He gritted his teeth in ecstasy as he shot another pulse of hot semen in honour of the new arrival; he was captivated by her already, even at that distance and after only seeing her for five minutes. Bruce had contacts within the academy and knew how the ‘girls’ were treated; he wanted to comfort the soft ginger sissy as soon as he could.
Pepper was marched inside the staid looking academy, which was richly decorated inside; oak panels gave it a feel of a mansion house, though everywhere there were umbrella stands filled with rattan canes to remind the inhabitants that this was a place of learning, where discipline was no doubt a large part of the agenda. Tomkins minced ahead with the case as the two followed, oblivious to the snivelling sissy who stood naked apart from a white crop top, all too apparent to Pepper. The sissy waited by an office door, her hands above her head which held a cane; her white bottom already striped with red, her little cock in a transparent plastic cage finished with a pink ribbon in a bow. The stern girl tugged at Pepper’s hand as she slowed a little, mouth agape. Grace smiled contentedly.
“Evidence of masturbation without permission no doubt. Disobedient sissies who do so are caned by their respective Head-Girl, caged for one week and caned each day for that week; this sissy is waiting by matron’s office; she’ll have a final caning from her and her pathetic dick will be released. The irony of the punishment is she’ll be aching to come after a week of canings, so Matron will take her to Mistress Bow’s office and she’ll be made to masturbate before her as a final humiliation.”
Pepper’s anus clenched at the plug and her little cock stiffened at Grace’s words; her enjoyment and approval of the scenario was all too evident in her tone, and the thought of a caning, and then being made to masturbate before such a stern woman gave the sissy a submissive thrill as she took in the foreboding atmosphere of her new home Tomkins took them up several flights of stairs until she reached a long corridor in the apex of the roof of this part of the huge building; she opened a door to a room within which were four double beds; Pepper had only a single at home, and wondered why such a luxury would be offered students at such an otherwise austere establishment. On one of the beds was a card; ‘Penderton’ was written across it. Tomkins placed Pepper’s case upon the bed and curtsied to Grace, who then opened a wardrobe and pulled out a white gown which she tossed to the bed also. She crossed her arms in dominant fashion and looked down at Pepper.
“Clothes off; You have an appointment with Mistress Bow and Nurse Wykett, you can sort out your things when you get back” She smiled wickedly as Pepper began to undress in full view of her. She waved the fluffy girl away to her bed.
“I’ll call you to come and fetch her when she’s done Tomkins.” Pepper tried her best, but could not hide her excitement completely; she exposed more of her hairless milky white and freckly flesh as she discarded each item, and fought hard to tame her erection as she removed the tight panties. Grace gave a look of contempt as Peppers little hairless cock and balls poked rigidly out.
“Mistress Bow will be so pleased to see that; she’ll soon have it between your legs. Now get the gown on and follow me.” Pepper followed the strutting girl obediently back down the stairs. As they passed the matron’s office the sissy had gone; Pepper’s cock poked forward in the loose gown as she heard the whoosh of a cane and the cries of the sissy as punishment was served. Grace looked back at Pepper with a broad smile as the cane cut the air again, and the sissy howled anew. She was then led across a large carpeted hallway to a gilded door; the wicked sound of the cane still audible.
Grace knocked, the door opened, and a very timid Pepper was ushered into the room.