Sissies must learn the pleasures and pain of being spanked across Mistress’s skirt.
Miss Fussy took an early morning phone call in the school office. “Hello, The Pretty Dress Sissy School. Miss Fussy speaking.”
“Good morning, Miss Fussy. It’s Grandma Wilkes. I sent Brendan to sissy school today in my blouse and skirt, knowing he would be punished.”
“Well yes, Grandma Wilkes. Sissies must arrive at school wearing their sissy dress. I’m afraid Brendan will have to be spanked across his bare ass.”
“Very good. I was hoping you would say that. I want Brendan to learn the importance of wearing his school dress. I’m also keen for him to be spanked as often as possible to make his bottom cheeks more tender and girlish.”
Moments later there was a second call from Grandma Rachel Jones. “Please give Rupert a good spanking in my blouse and skirt. I like to dress him in my most feminine things – all as part of his home sissy training.”
“He will certainly have to be spanked, Grandma Rachel,” replied Miss Darling. “The boy must learn that only his sissy school dress is acceptable for when he is travelling to and from The Pretty Dress Sissy School.”
When Brendan and Rupert got to school and were brought into the humiliation centre, they could see at once they were in trouble from the cross looks on the faces of Miss Fussy and Miss Darling. The boys stood, one in front of each Mistress, to have their coats removed and shrank with worry as the women tutted and stood with their hands on their hips in indignation.
“Well. What have we here. A pair of disobedient sissies who are not wearing their sissy dresses when they arrive at sissy school. This will not be tolerated.”
“B-But Miss Fussy,” said Brendan, hanging his head with shame in front of Miss Fussy who looked so severe with her short, black, glossy hair, wearing a blouse with a big white pointed collar that made her look so strict, “Grandma dressed me in her blouse and skirt for breakfast, and there wasn’t time for me to change into my dress before setting out to walk to sissy school.”
Miss Fussy surveyed the miscreant. He drooped with self-pity under her glare in an evening blouse of rose pink satin with billowing sleeves and an enormous rounded collar edged with white lace. He held his hands together to hide the stiffness of his cock behind the pink pleats of his grandmother’s long, wide skirt.
“And what is your excuse, Rupert Willoughby?”
“Please Miss Darling, Grandma made me wear one of her best silk blouses today and her black pleated skirt nearly down to my ankles. She said it would remind me that tonight she is going to have me in her silkiest lingerie while she sits me on her knee to tell her all about my lessons at sissy school today.”
“That is no excuse. The rule is you wear a dress – a sissy dress – to school each morning, and go home in one at tea time. As always, we spank the bottoms of sissies who are naughty. Miss Fussy, please smack your sissy over your knee while I smack mine across my skirt.”
Her words were the signal for an outpouring of girls’ anxious fears. “Please don’t spank my bottie, Miss Fussy,” cried Brendan. “Please don’t spank me,” cried Rupert trying to keep his bottom and legs away from Miss Darling as she took her place on a chair.
As the Mistresses held the boys in front of them to undo the waist of their skirts and slip them down to their legs, followed by their grandmothers’ waist-slips and full-cut silk panties, the boys’ fright overtook them and their sobs soon changed into an outpouring of tears. Their horror redoubled as they were pulled downwards until their cocks and thighs settled into their Mistresses’ laps. Their hands had to reach forward to the floor to stop themselves from sliding off.
“Please don’t – sob-sob – Miss Fussy!” cried Brendan as his teacher’s hand smoothed across his globes to measure the soft area of sissy flesh to be smacked.
“Ohhh! - I didn’t mean to be naughty, Miss Darling, ohhhh!” cried Rupert, waiting for that first horribly painful slap. He felt his hand being removed from his ass and held out of the way, then: SMACK! WHACK! SLAP!
The sting of each smack left a searing patch of pain across each boy’s bottom, to be smacked again on exactly the same spot, and again and again and again. It was natural for teenage boys to struggle in this position, their cocks sliding and squeezing into the skirts of their schoolmistresses. And it was equally to be expected that the length of the spanking – almost ten minutes – meant the arousal felt by two girly boys when their silky blouses slide forward to surround their faces in very feminine silk collars and their bare legs are caressed in the silky pleats of their grandmothers’ skirts, should feel more and more feminized and desperate.
So it was that before the spanking finished, their genitals were feeling so overcome by their feminine surroundings that Brendan lost all his control and he began to ejaculate onto the silky knee of Miss Fussy, while Rupert lost it altogether and squirted so much into Miss Darling’s skirt that he slid to and fro across her legs in a growing puddle of sissy cum with each smack that she rained onto his burning ass cheeks. Their Mistresses were cross of course at having to change their messy skirts while the sissies stood in opposite corners of the room with their noses right in the corner, quietly sobbing as their cocks continued to dribble at the memory of sliding in those lovely skirted knees.
“Come here, Miss Brendan,” cried Miss Fussy when she had wiped herself clean and put on another skirt and more perfume. “It’s high time you were dressed in the panties and petticoats that a little girl would wear, so that you can wear a sweet dress for your lessons at sissy school today.”
Rupert was cleaned up too and stripped of his grandma’s underwear, so that he could be dressed in frilly sissy panties over his tender half-stiffened penis and fastened into a frilly tiered petticoat. His dress was in white silk-chiffon with extra flounces of pink satin round the lower half of the skirt, while his little puffed sleeves were in pink satin too, as well as his delicate Peter Pan collar.
Brendan was dressed in a ruffled party dress in peach-pink organza for a four-year-old, which buttoned down the back and had large puffed sleeves edged with organza frills. The sash of white satin was very deep and done into a huge bow at the back of his waist.
“Now you girls are ready for sissy school,” declared Miss Fussy. “But just to emphasise the lesson you have learnt today, we are going to send you both home in your Grandma’s lingerie again with their blouses and skirts, with a message that your bottoms are to be smacked again for wearing the wrong things while you are going home from sissy school.” Both the sissies started to sob again, this time in their rustling, frilly dresses. “We want you to associate wearing Grandma’s lovely clothes,” went on their schoolmistress, “with having your bottoms smacked, because that is what sissies need every day. How else would their asses become as tender and girly as we require at The Pretty Dress Sissy School.
***
There are ten new Prim pics on the first of the month every month in the Penelope Room at www.primspetticoatwendyhouse.com/feminization.htm
