The Art of Penelope Pencil Penis
with storyette by Prim

Dressing Time for Mister Dilly

  "You must be merciless with him, Rachael," declared Miss Harridan, the Principal of the Angelina Jayne Finishing School for Arrogant Young Ladies. "Now that he has been appointed as a male member of our teaching staff, he will wear the appropriate dress and he will like it."
Rachael Smirks gave a loud giggle. "No worries, Miss, I will," sang the confident 18-year-old as she fastened his wrists to his knees with powder blue ribbon. "Hear that, Dilly?" and she finished off her task with a slap across the butt of the naked new male teacher who was being left in her care, "you're going to get very girly about wearing your pretty dresses, aren't you pet? Even if I have to WANK you til you show me."
Miss Harridan "Hmm-ed" with a smile. "Be sure to wank him gently, delicately, darling. The trick is to make him become more girlish even as he's be-cumm-ing a sissy," and the two females roared with laughter as they shared the joke.
As soon as the Principal was gone, the Smirks girl lost no time in showing Charles Dilly what he could expect. She stood square to the naked male, his hands tied behind him and ribboned to his knees, and six slaps across the face rang round the room, punctuated with cries of pain from the desperate male.
"Oooowww! He-e-e-elp me, someone! Miss Harridan! Aarrghhh!" and he fell silent as his hair was seized and pulled down into the front of the girl's short, pleated maroon skirt. "Save your breath, you panty-brain. I'm in charge - it's what Miss Harridan wants, and I'll tell you something else: I'm one of the quiet, friendly girls at Angelina Jayne." She delivered another couple of slaps while she held him down there. "You can call me Miss Rachael. In face, ASK me if you can call me Miss Rachael!"
"Ohhhh, please can I c-call you Miss Rachael?"
He found his head brought up again in front of her grinning lipstick. "I think you better had. Now, let's go and see your new dresses." If he had been a sheep being bundled into the sheep dip, he would have been dragged into the next room a lot more gently. He found himself in a dim room, barely upright on his feet, with a sort of hat-stand in front of him holding three little girls' dresses. "Now that you're standing in front of your pretty little dresses, Dilly," his guardian told him as she stooped at his legs and fastened the ribbons round his ankles too, "you're not going anywhere for a while. Not until you've christened them with oodles and oodles of spunk!" she moved a lamp into position and turned it on, flooding the little show of dresses with light. His penis stiffened. Was he really going to wear one of these? Surely n...
A grip of five fingers closed round his shaft, softly, deftly, and worked up and down its length with smooth, inviting squeezes. "They're lovely, aren't they?" she prompted. His hesitation drew her fingers into a fierce claw and he squealed his reply.
"Yes Miss!" As she relaxed her grip, she felt the growing stiffness. So he liked being controlled by a woman.
"You want to wear them don't you?"
The slightest pressure of her hand and he yelped another "Yes Miss!"
"ASK me to let you wear them!"
"Oh please let me wear the dresses, Miss Rachael, please."
His tormentress clutched him in a nice sliding rhythm and turned to the dresses. "What do you like about the pink one, Dilly?"
"Oh, the pretty ruffles round the skirt, ma'am, er, Miss Rachael."
"Mmmm." Her hand had him in a full erection now. "And the floral one?"
A slight tightening of the hand. "Oh, ohhhhhh, everything Miss Rachael."
"You want me to put it on you, don't you, Dilly? To start teaching the girls in?"
A tear ran down each of his cheeks. "Y-Yes Miss Rachael. P-P-Please put me into the little girls' dress."
"There's a good boy," she cooed, and undid the ribbons at his wrists, leaving his knees and ankles tied. "We can't have you going anywhere during our little dress try-on, can we, sweetie?"
Charles Dilly's voice was crying as he bleated: "No Miss Rachael," and she slipped a petticoat over his head, fastening its ribbons at his neck. Then she dresses him in the first of his dresses, just as he began to ejaculate with very submissive, feminine feelings. He knew he was going to be cumming a lot more during his employment at the Angelina Jayne Finishing School for Arrogant Young Ladies.