Sore Bottoms for Two

A girl earns herself a visit to the Deputy Headmaster’s study and gets her best friend into trouble as well. By a new writer to us.

By Brian Melville

Ashleigh  Anderssen is an very attractive, tall and slender built, eighteen year old with long blonde hair, blue eyes, long shapely legs and a well toned, tight little round bottom. As a sixth former at The Rose Academy for girls in the east of London, the teachers may use size 12 slippers and the deputy headmaster one of his two trusty canes across the bottoms of the naughty girls. The cane may only be administered across one layer of clothing and at The Rose Academy the girls to be caned have to change into navy blue punishment shorts for it, in a private room just down the corridor from the deputy headmaster’s study, all under the supervision of a female member of staff.

It was a rather chilly Monday morning in the east of London, and the twenty five girls of 6 B at were seated at their desks in their third class of the day, Mathematics, which is a double period. Ashleigh Anderssen hated  Mathematics and decided to write her boyfriend of two years, James Goldberg, a  20 year old law student at Cambridge University, a letter telling him how much she misses and loves him, since they now only get to see each other during holidays when James is back home from university.

As Mrs Lewis explained how to solve the square root maths problems the girls had to finish as homework for today’s class, she noticed Ashleigh being constantly busy with writing something while she was supposed to give attention to what was being explained on the black board.

Mrs Lewis then interrupted her lecture. “Ashleigh Anderssen, would you be so kind as to repeat to the class what I have just explained?”

Ashleigh looked up directly into her teacher’s eyes.

“Well Ashleigh?”

Ashleigh replied: “Uh, uh, uhm, James is at university, uh, uhm.”

The teacher, now rather angered by this, said: “Come to the front of the class, girl, and bring whatever you were writing along!”

The blonde eighteen year old looked at the teacher and blushed.

Then Mrs Lewis snapped. “To the front of the class, right now, girl!”

Ashleigh, now red faced, stood and walked to the front of the class with the piece of paper in her hands. As she came to a halt in front of the teacher, Mrs Lewis took the piece of paper and read only one sentence before looking sternly at the pretty sixth former in front of her.

“Take your little love letter and go to Mr Harrison, the deputy headmaster, and explain to him why you are not paying attention in my class, but rather want to waste not only your time but also mine by writing this rubbish to a boy!”

Ashleigh, now pale faced at the prospect of getting only her second caning in her 6 years at The Rose Academy, took the note  from the teacher and with her head bowed she turned and headed for the deputy headmaster’s study in silence. As she walked swiftly down the corridors to Mr Harrison’s  study she hoped that the deputy head would spare her the cane and instead let Mrs Lewis slipper her across the seat of her skirt.

Reaching the deputy headmaster’s study, Ashleigh Anderssen made sure her uniform, consisting of a navy blue skirt, which was altered to sit precisely at 3 inches above the knee as prescribed in the school rules, crisp white long sleeve blouse, navy blue tie with the school emblem, a red rose embroidered on it, white knee socks, black Mary Jane school shoes and navy blue blazer with the emblem on the chest pocket, was perfect. She even bent down and wiped her shoes with a tissue she had in her pocket.

Ashleigh then took a deep breath and knocked  on the door. There was an awkward moment of silence, then came the stern voice: “ENTER!” from inside.

Ashleigh entered the study and, after closing the door behind her, she turned to face the deputy headmaster.

He snapped: “Come stand there, girl!” pointing to a spot just behind the two chairs in front of his desk.

As she reached the preferred spot, Mr Lewis barked: “Hand me that piece of paper in your hands and then put your hands on your head and face me, girl!”

Ashleigh did as she was told and saw the deputy headmaster read her private letter to her boyfriend. Then Mr Harrison, a short chubby man in his early forties, looked at the six former in front of him and asked: “Name, form and who sent you to me, girl?”

The blonde girl answered swiftly: “Ashleigh  Anderssen,  6 B, Mrs Lewis sent me, Sir!”

Mr Harrison then asked: “Would you be so kind as to explain to me why you were writing this, this silly excuse of a love letter while you should be paying attention to Mrs Lewis.”

Ashleigh just bowed her head and stared at the tips of her shoes, feeling rather silly having to stand there with her hands on her head like a naughty little first form girl. She thought to herself the deputy headmaster was rather rude, regarding her love letter as a ‘silly excuse of a love letter.

“Well, Ashleigh, answer me,” snapped Mr Harrison.

Ashleigh looked at the deputy headmaster and answered: “It was not my intention to write the letter, sir. It was just a lapse of concentration, sir.”

Mr Harrison looked at her with anger in his olive green eyes, then spoke sternly: “A lapse of concentration, you say, girl?”

Mr Harrison stood and picked up one of two canes from a bookshelf behind him. He turned and, whilst swishing the cane through the air a few times, he continued: “Maybe six of the best with the cane will help stop any further sudden lapses of concentration you might get, miss Anderssen!”

Ashleigh, now looking wide eyed at the deputy headmaster, was in shock about the pronounced punishment. With her previous visit to Mr Harrison, she only got two strokes and the six he intended to administer to her bottom now seem rather severe for only a second offence in six years.

“Well girl, anything to say for yourself?”

Ashleigh replied quietly: “I am sorry, sir. It will never happen again, I promise.”

Mr Harrison snapped: “Speak up, girl!”

Ashleigh repeated herself. “I am sorry, sir, it will never happen again, I promise.”

The deputy headmaster looked at the now visibly shaken sixth former in front of him as he said with a smile: “I am sure you will not do it again, Anderssen, and yes, you will be sorry once I have finished caning your bottom!”

Ashleigh cringed at the thought of what was about to happen. Mr Harrison then placed the cane on his desk in plain sight of the attractive blonde girl as he picked up the telephone.

“Mrs Whitecomb, will you be so kind as to assist me with the administration of the cane to a student in my study? Thank you, Mrs Whitecomb.”

Mrs Whitecomb was the school secretary and she had also witnessed Ashleigh’s only previous caning. The sixth former was relieved, knowing it was the secretary that would be witnessing her punishment. She was glad it was not the head girl, Mary Thomas, an attractive and athletic ash blonde girl from 6 A. Ashleigh could just imagine the smile and comments Mary would make in the little office where the girls have to change into the punishment shorts.

The deputy headmaster then took the punishment book from a drawer below his desk and opened it at the last entry. Ashleigh could actually read the last entry in the book from where she was standing with her hands still clasped on her head.

Sarah-Louise Smithfield, 6 E, Disruptive behaviour in class, 3 strokes over punishment shorts.

Sarah-Louise, also known as Louise to her fellow students, was a short, plump redhead with freckles covering her face, who wore glasses. Louise was a real bookworm and always one of the top three achievers at The Rose Academy. It was rather a strange thought as Ashleigh pictured Sarah-Louise being so disruptive in class to merit a visit to the deputy headmaster for the cane. Ashleigh then returned her attention to what the deputy was currently doing, entering her name for the second time in the punishment book.

Ashleigh Anderssen, 6 B, Inattentive behaviour in class, 6 strokes over punishment shorts.

Ashleigh saw the last bit of the entry and shrugged at the thought of having to take off her tiny lace pink knickers and skirt and having to wear those ugly, faded navy blue punishment shorts, which the girls were sure were old gym shorts of some boy from the boys school down the street. Then there was a knock on the door.

“Enter!” Called Mr Harrison.

The school secretary came in.

“Ah Mrs Whitecomb, thank you for always assisting me with these unpleasant formalities.”

The secretary, a short, slender lady in her early fifties with dark blonde hair, smartly dressed in a long grey skirt, pink blouse, stockings and black shoes with a 3 inch heel, smiled at the deputy headmaster and replied: “Don’t mention it, Mr Harrison.”

The deputy headmaster then asked: “Mrs Whitecomb, will you please see to it that Ashleigh Anderssen gets changed into a pair of punishment shorts as required by the school rules?”

The secretary nodded as she turned to the naughty sixth former and, with a comforting smile, she said: “Follow me, Ashleigh.”

She turned and opened the door, beckoning the schoolgirl to leave the study. She then closed the door and Ashleigh followed her to a small room next to the staff bathrooms. Mrs Whitecomb unlocked the door and, once inside, she closed the door and proceeded to a shelf holding a number of faded navy shorts, neatly folded and stacked in piles of ten.

Taking a pair of shorts from it, she turned to face the eighteen year old and spoke gently. “Ok Ashleigh, take your blazer, skirt and knickers off and place them neatly on the table. Then put this on.” She placed the shorts on the table.

Ashleigh blushed slightly as she took her school skirt off revealing her skimpy, but highly fashionable, little pink lace knickers. Then she slipped them down to and over her shoes. Ashleigh turned her back to the secretary as she struggled to get the thin faded shorts over her shoes, showing her snow white, unblemished, well toned, pert little round bottom to the secretary. Once the shorts were in place, the secretary instructed her to let her white blouse hang over the shorts. Then they made their way back to the deputy headmaster’s study for the looming six of the best.

As Ashleigh followed the secretary down the corridor, they were passed by a few first and fifth form girls who looked at the sixth former, while one of the first form girls made swishing sounds as she passed.

The secretary knocked on Mr Harrison’s door and again was greeted with a stern: “ENTER!”

She opened the door and ushered the blonde girl inside before entering herself and closing the door behind her. Ashleigh saw one of the two chairs in front of the desk had been moved to the corner opposite the door, with its back to the door, ready for her to bend over for her punishment.

The deputy headmaster snapped: “Hands on your head, Anderssen!” To which Ashleigh complied hastily.

Mr Harrison got up from his chair and, after removing his blazer, he rolled up the right sleeve of his light blue shirt and picked up the waiting cane from his desk. As he walked around the desk towards Ashleigh, he snapped again: “Go stand by the back of the chair, facing it, then bend over and hold on to the front legs below the seat, Anderssen!”

Ashleigh Anderssen moved to the chair and, with a soft sigh, she bent over the back of the chair, gripping the crossbar between the front legs and feeling the shorts stretching rather tightly across her up-turned bottom.

The secretary moved forward and lifted the girl’s blouse, folding it over the girl’s lower back. Once the secretary was out of the way, the deputy headmaster took up his position to the right of the bending girl and placed the cane firmly against the presented target, gently tapping it a few times. Mr Harrison then took a full minute to do some practice swings through the air behind Ashleigh, causing her to tense her bottom with every swish of the rattan, not knowing when the first stroke would land across her bottom.

Mr Harrison then held the cane against the well presented target covered in the tightly stretched, faded blue shorts that would offer little protection against the sting of the cane. Without warning, the deputy headmaster drew the cane back and, with a swing and a flick of the wrist, the cane hissed through the air with an swish, coming to an stop with a thwack across the centre of Ashleigh’s bottom, causing the eighteen year old to let out a deep breath followed by an ‘ow’ in an whispered voice.

Mr Harrison waited 15 seconds before he whipped the cane down again with a swish and the all to familiar thwack as it struck its target, causing another ‘ow’ from the blonde six former.

Ashleigh could feel the stinging pain intensifying as the second stroke also had 15 seconds to sink in. Then, with a single tap to her bottom, swish, thwack!

Three strokes had been perfectly administered to her bottom, from the middle up towards her lower back, but all concentrated in a 1 inch band on her now stinging bottom. 15 seconds later, number four landed across Ashleigh’s upturned bottom, just below the first stoke, with a swish, thwack.

“Ouch, sir!” Ashleigh shifted her feet as her bottom was now feeling like it was on fire.

This time Mr Harrison took a full minute, just tapping the beautiful female bottom before he let stroke number 5 find its stinging spot on the young lady’s bottom.

This caused a louder yelp and some quick breathing with she cried: “Ouch! It hurts!”

She swayed her hips and shifted her weight from foot to foot to try and soothe the immense stinging pain now covering her entire bottom.

Another full minute of light taps went by and then a swish through the air, but no stinging contact. Then another few taps and a stern: “Keep still!” from the head before an almighty swishhhh, and a resounding thhwaacckk as the cane struck its target for the final time, just above the crease where bottom turns into thighs.

This caused Ashleigh to almost lose her grip on the cross bar, her head jolting back and her left leg giving an involuntary kick.

“Ow,.ow, ow, it hurts!” She cried, as the tears flowed freely.

The deputy head waited another 20 seconds before speaking. “Let that be a lesson to you, Ashleigh Anderssen! Get up!”

The six former stood and as her blouse fell down covering her now burning bottom, her hands went to her bottom giving it a frantic rub to try and soothe the pain.

The deputy head returned the cane to the shelf before he spoke again.

“I do not want to see you here again for the same offence. Are we clear, girl?”

Ashleigh replied while sniffing back the tears and rubbed her bottom. “Yes, sir! Sorry, sir!”

Mr Harrison then spoke to the secretary. “Thank you, Mrs Whitecomb. Will you please see to it that miss Anderssen gets changed back into her school uniform and returns to class?”

Mrs Whitecomb nodded and, with a gentle smile, looked at the blonde girl with the tear stained face, still rubbing her well caned bottom.

“Follow me, and let us get you back into your skirt and blazer.”

As they left the deputy headmaster’s study, Ashleigh just prayed that no one saw her as she followed the secretary to go back to the little room where she’d left her clothes. Once there, Ashleigh took the awful shorts off, but she could not resist looking over her shoulder to see the damage the cane caused to her little bottom. 6 angry looking red tramlines covered three quarters of her bottom, with only the top quarter still its unblemished milky white colour.

The secretary also saw the eighteen year old’s bottom and could not help but stare for a few seconds at how precisely Mr Harrison had delivered the 6 strokes, all perfectly parallel and spaced in such a way that young Ashleigh Anderssen would not be able to sit down without being reminded of the effects of her visit to his study.

Once fully dressed in her school uniform, the secretary dismissed her by saying: “You can go back to your class now, Ashleigh.”

The blonde teenager left the room and made her way back to her mathematics class. She knocked on the door before entering.

Mrs Lewis spoke. “Welcome back, Asleigh. So what did Mr Harrison have to say about that silly love letter?”

Ashleigh blushed and answered: “Mr Harrison caned me for it, Mrs Lewis.”

The maths teacher smiled at the teenager and asked: “How many strokes?”

Ashleigh blushed even more and answered,  while looking at her feet: “6 of the best, miss.”

The teacher said: “Good! Now go back to your desk and get on with your work, girl!”

Ashleigh got back to her desk, all too aware of the rest of the class looking at her, some smiling others with stern faces. She saw her best friend, Hannah Green, a lovely looking girl with long straight black hair and green eyes, about an head shorter than Ashleigh and a rather skinny eighteen year old, smiling at her.

Ashleigh took her seat carefully and winced in pain as her freshly caned bottom made contact with the hard wooden seat of her school desk.

Ashleigh let out a muffled: “Oh my gosh, it hurts more when I sit down!”

This caused Hannah to burst out in a loud laugh. Mrs Lewis looked up, frowned at Hannah Green who was now laughing rather hysterically.

The teacher snapped: “Hannah Green!!!”

The skinny girl stopped her laughing immediately, looking at the teacher.

“Stand up, girl!!!”

Hannah stood with wobbly knees as she realized that she was now in big trouble and might find herself making the trip to the deputy headmaster’s study.

Mrs Lewis snapped: “So you think it is funny seeing Ashleigh struggle to sit after her caning, girl?”

Hannah mumbled: “Uhm, yes. I mean, NO, miss! Sorry, Mrs Whitecomb!”

The teacher took her black slipper from her desk and, as she turned to face the class and the standing Hannah Green, she said: “Come here, girl! I am sure that 8 strokes from my slipper will cause you to also struggle to sit comfortably.”

Hannah walked slowly to the front of the class.

The teacher snapped: “Turn around to face the class with your hands on your knees, girl!”

The naughty girl did as she was told and within seconds, whop, whop, whop, whop, four very hard and stinging smacks of the slipper fell across Hannah Green’s bottom, causing the girl’s eyes to water up.

Then, whop, whop, whop, whop, the last four smacks landed fast and furious across the teenager’s seat of her tightly stretched skirt. Hannah was now crying softly as she stood and her hands went to massage her stinging bottom. The rest of the class were all looking wide eyed.

Mrs Whitecomb spoke again. “Now go sit down and carry on with your work, all of you!

During the first break, Ashleigh and Hannah met in the bathroom and checked each other’s bottoms, after Hannah apologised to Ashleigh for laughing at her in class. The rest of the day went without incident except for the general teasing from a few first formers, who heard about the six form girl getting caned by the deputy headmaster.

Ashleigh finished her school career at The Rose Academy without any further punishment, but Hannah visited the deputy headmaster’s study two more times for a dose of the cane at each visit.

The End

© Brian Melville 2017