James Steward, Deputy Headmaster

A new deputy headmaster starts a new regime

By Brian Melville

Fifty year old James Steward was a man of five foot eight inches, with grey hair, brown eyes, and a rather big stomach. He entered his study at Sydmore College for Girls on the south coast of England where he transferred to about ten years ago when he was promoted to Deputy Headmaster by the Department of Education. At the time, the only available position was at the all girls school.

He was a formidable, strict but fair, man, and loved by all three hundred and twenty-seven girls at the school, as well as all thirty-six members of staff.

James remembered his first day very well, when the Headmistress asked him to take over the disciplinary duties at the school, and to restore the discipline which had got out of hand due to the headmistress being too busy to deal with it all the time.

During his first week, James had numerous meetings with all the staff members and decided that it was time to bring the cane out of semi-retirement, as the cane has not been used at all during the year and nine months previously.

During the second assembly of the year the headmistress announced the decision to the girls.

“As from today, Mr. Steward, the Deputy Headmaster, will be dealing with those of you girls who really can not behave yourselves properly. If you think you will get off with a scolding or lines like in the past, think again! Those that end up in front of the Deputy Headmaster may well feel the sting of the cane across your bottoms!”

This caused quite a buzz as the words of the Headmistress echoed through the school hall.

The school had a traditional uniform for junior phase, which was years one to four, which consisted of a maroon skirt, white long sleeve blouse, maroon tie, maroon pullover, maroon blazer, white knee socks and black school shoes without a heel that fastened with a small silver buckle across the top of the foot.

As for the senior phase, which was year five, six and upper six, the girls had the option to wear maroon trousers and maroon ankle socks instead of the skirt and knee socks.

The school also had a gym kit for gym class and sports practise sessions after school, which consisted of white gym shorts, ,maroon vest with three horizontal white stripes across the chest, maroon knee socks and white plimsolls.

The following two weeks after the announcement went by without incident, until a cold Monday during the autumn of 1981. James Steward was busy with the endless reams of paperwork until there was a knock on the door.

“Enter!” James snapped, as he looked up.

The door opened and a tall, skinny girl with shoulder length dark brown hair entered the study. From her uniform, James gathered that she was from the junior phase, as she was wearing the skirt and knee socks.

“Close the door behind you, and come stand over there and face me, girl!” The Deputy Headmaster snapped.

The rather nervous looking girl complied and within seconds she stood in front of him with her hands behind her back.

“Full name and form, girl!” Snapped Mr Steward.

“Uh, uhm, Hellen Bates, six B, sir!” The girl stuttered.

“Why are you here, girl?” The headmaster snapped.

The girl didn’t respond, as she just bowed her head and stared at the grey carpet in front of her feet.

“Answer me, Bates!” The Deputy Headmaster snapped.

“Miss Cambridge sent me for disrupting class by talking to my friend, sir. Sorry sir!” The girl mumbled.

The Deputy Headmaster looked at the girl for a few seconds, then he took the punishment book from the drawer on his left and leafed through it, before he snapped: “You will be sorry when you leave my study shortly, girl! Since you have not been in trouble before, according to this punishment book, I will only give you two strokes of the cane, Hellen!”

Hellen just bit her lip nervously, as she realized that her clean record of not being punished at school would no longer exist once she left the study. She watched as the Deputy Headmaster entered her name into the punishment book, on a clean page.

“28 September 1981, 09.45, Bates Hellen, 6B, Disruptive behaviour in class, two strokes of the cane across school skirt.”

He then got up and, after clearing some space on his desk, he moved around his desk, as he made his way to the door where a cane hung from a hook. He flexed it between his hands as he addressed the girl.

“Move that chair out of the way, girl!” He pointed to the black armchair to his right.

Hellen stepped forward, then lifted the chair and moved it about four feet to the right.

As she turned towards the Deputy Headmaster, he snapped: “Bend over the desk, girl!”

Hellen, shocked at the Deputy Headmaster’s instruction, stepped up  to the edge of the desk and forced her upper body over the surface of the large oak desk, gripping the edge on the other side with both hands.

“Right down, girl!” The headmaster snapped again.

Seventeen year old Hellen soon found herself laying on the desk with her legs at an angle down to the floor behind her. Her toes rested on the carpet. The Deputy Headmaster placed the cane across the centre of the girl’s skirt-clad bottom and tapped it a few times. Then, with a firm swish, he let the cane rip through the air before it fell with a resounding thwack, across the centre of the up-turned bottom.

This caused poor Hellen to stomp her feet on the floor as the stinging pain settled across her bottom. James gave the girl a few seconds to recover, then he tapped the cane a few times again against her fleshy, round bottom, before he whipped the cane down hard, with a swwisshh, followed by a resounding tthwacckk,as the cane landed right on target, half way between the first stroke and where bottom meets thigh.

Hellen’s head jerked back, but she managed to stay in position as she yelled: “Oww, ouch, owwie!”

The Deputy Headmaster returned the cane to its place on the hook behind the door and, as he turned, he couldn’t help but see the girl with her feet now next to each other, firmly on the floor, swaying her hips from side to side in an attempt to ease the pain.

After about a minute, the Deputy Headmaster snapped: “Let that be a lesson to you, Hellen! Now get up and put the chair back in its place!”

Hellen got up from the desk and clasped her burning bottom with both hands for a few seconds before giving it a good rub. Then she took the chair and moved it back to its place. She soothed her bottom again with both hands as she stood in front of the Deputy Headmaster.

“You may return to your class, and don’t let it happen again, girl!” James snapped as he sat back down behind his desk.

The poor girl turned and exited the study with one hand firmly clasped to her bottom. She returned to her class where she had to inform the teacher about her punishment. Hellen returned to her desk and sat down rather uncomfortably for the rest of the class.

James Steward continued with his work and, after he enjoyed a nice cup of tea during first break, he returned to his study to find an eighteen year old, short, chubby, redhead, Nancy Jones, who was the Head Girl, waiting for his return. She had with her a fellow upper sixth girl, Kayleigh Smith, a pretty, tall, athletic ash blonde eighteen-year-old who seemed very nervous and close to tears.

“Follow me inside, both of you!” Mr. Steward snapped as he unlocked and opened the door to his study.

Nancy shoved Kayleigh towards the door. The girls entered the study and Kayleigh made her way to stand in front of the Deputy Headmaster.

As he got to his chair he snapped: “Close the door behind you, Nancy!”

As Nancy closed the door, she saw the cane and was very relieved she would not be on the receiving end of it. Then she went and stood to the right of Kayleigh.

“So, Nancy, please tell me why you brought Kayleigh to my study.” The Deputy Headmaster asked.

“Well, sir, I found her smoking behind the bike shed, sir!” The Head Girl  replied as she placed a half smoked cigarette, a lighter and a cigarette packet with only two cigarettes in it on the Deputy Headmaster’s desk.

James Steward looked at the cigarettes and then at Kayleigh, then he snapped: “So, what do you have to say for yourself, young lady?”

“I’m sorry, sir!” The girl meekly replied.

The Deputy Headmaster again paged through the punishment book and saw Kayleigh Smith’s name three times as he reached the page where he made the previous entry, which was also his first.

He looked up at the girl and snapped:  “Smoking at school is a very serious offence, girl, so I have no choice but to give you six strokes with the cane, girl!”

“No, no please, sir! Not six. Please sir! I will never do it again, sir!” The blonde girl pleaded.

“Quiet girl! Hands on your head and stop fidgeting!” The Deputy Headmaster snapped.

The poor teenager complied as she glanced towards a grinning Nancy, who was standing with her hands behind her back while the Deputy Headmaster entered Kayleigh’s details into the punishment book.

“11.10, Smith Kayleigh, Upper 6A, Smoking, Six strokes of the cane, across trousers.”

Kayleigh couldn’t help but notice Hellen Bates’ name just above her own, and found it hard to believe that Hellen could actually disrupt a class, as she was always very quiet and well-behaved.

Mr Steward got up from his chair and, as he removed his jacket, he addressed the Head Girl.

“Please hand me the cane, Nancy!”

The Head Girl turned and removed the cane from its hook, smiling at her fellow sixth form classmate, who had her long, ash blonde hair tied in a single ponytail rather high up on her head. Nancy handed the cane to the Deputy Headmaster.

The Deputy Headmaster noticed the smile and snapped as he took the cane from the Head Girl: “Thank you, Nancy, and you can wipe that smile off your face unless you want to join Kayleigh for a dose of the cane!”

The redhead immediately stopped smiling as she meekly replied: “Yes, sir! No, please sir, I don’t want to be caned, sir!”

“Good! Now, return to your class, Nancy!” Mr Steward snapped.

Nancy turned and exited the study quickly, closing the door behind her.

Then the Deputy Headmaster snapped again as he made his way towards the sixth form girl: “Right, turn around so that you’re facing the window, with your back facing the door.”

There was a slight pause as he waited for the girl to do as instructed.

“Now, lift your blazer and bend over, girl!”

Kayleigh lifted her blazer and leaned forward, placing her hands on her knees, feeling her maroon trousers tightening across her small, round, firm eighteen-year-old bottom. The Deputy Headmaster took up his position to her left side and slightly behind as he placed the business end of the cane firmly against her up-turned bottom.

“Six strokes! I want you to keep still, girl!” The Deputy Headmaster snapped as he tapped the cane against her bottom.

“Bend over a bit more, girl! Hands below your knees and straighten your back! That’s better!” Mr Steward continued as he tapped her bottom with the cane.

Then with one swift movement the Deputy Headmaster swung the cane down with a swish, followed by a firm thwack, as the cane left a searing line of fire across the centre of the girl’s poor bottom.

Kayleigh’s muscles tensed up. She struggled for breath for a few seconds as she worked through the pain in silence. Ten seconds went by before the cane tapped her bottom again, and swish, thwack, the second stroke landed just above the first, causing the ash blonde girl to moan softly: “Ouch, it stings!”

Again, ten seconds ticked by followed by a single tap and a firm swiishh, followed by a resounding tthwacck, causing Kayleigh to leap up into the air as she yelled: “Ow, ow, ow, ow, my bottom hurts!”

Before the Deputy Headmaster could say anything, the girl assumed the prescribed position as she breathed heavily. This time the Deputy Headmaster waited a full thirty seconds, just swishing the cane through the air a few times behind the bent over girl before he tapped the cane against the lower half of her well-presented bottom. Ten seconds and there was the familiar swissh, thwwackk, as the fourth stroke landed just below stroke number three.

Before the teenager could react to the sting, the cane hissed through the air and the fifth stroke fell just below the previous stroke with the tip of the cane landing across the end of the previous stroke.

This caused the young Miss Smith to jump about a foot into the air and howl in pain. She hopped from foot to foot, clasping her scorched right bum cheek.

“Owwwweee, oww, ow, oowwwee!”

The Deputy Headmaster gave the girl a full minute to compose herself.

“That’s enough, girl! Back into position for your final stroke!” Mr Steward snapped.

Kayleigh sighed as she turned and assumed the position again, for the sixth and final stroke. The Deputy Headmaster did not even touch her bottom with the cane, but after twenty seconds it hissed in its customary ssswwissh, followed by a cracking ttthhwwackk, right on the crease where bottom meets thigh, causing Kayleigh to bend her knees as she gritted her teeth and gasped for air. Then she swayed her hips from side to side in an attempt to ease the intense pain covering her entire bottom.

The Deputy Headmaster returned the cane to its place behind the door and then looked at the cute, well-presented bottom swaying from side to side.

“Right, Smith, get up and get out! Back to class!” The Deputy Headmaster snapped.

Kayleigh straightened and, as her blazer fell back in place over her bottom, she couldn’t resist but give it a frantic rub before making her way to the door. Back in her class, she had to stand in the corner at the back of the class as she was unable to sit.

The day went by without further incident until ten minutes before the end of the day when there was a knock on the door followed by the door being opened and Miss Patricks, the gym teacher, stormed in dragging a girl in gym kit behind her.

As they came to a halt in front of his desk, the Deputy Headmaster saw the girl in tow was none other than the red-headed Head Girl, Nancy Jones.

“Miss Patricks, what on earth are you doing?”

“I caught this little madam in the gym bathrooms, hiding in one of the toilet cubicles, skipping class!”  The six foot tall teacher replied.

“Is that true, Nancy?” The Deputy Headmaster snapped.

Nancy Jones lowered her head in shame as she replied in a whisper: “Yes, sir.”

“Thank you, Miss Patricks, I will deal with Nancy. You may return and attend to your class.” Mr Steward addressed the teacher.

Miss Patricks turned and made her way out of the study as she said: “Thank you, Deputy Headmaster.”

James Steward could not believe the Head Girl would actually skip class and decided to deal with her appropriately.

“Nancy, you are NOT a first year girl and you know that this kind of behaviour is unacceptable, especially as you are Head Girl of the school. So, before I decide on a suitable punishment, do you have anything to say for yourself, young lady?”

“No excuse sir! Sorry sir!” The Head Girl replied meekly.

Mr. Steward took a full minute to decide on the punishment while he just stared at the short, chubby redhead eighteen-year-old dressed in her gym kit.

Eventually he addressed the girl again. “I will be lenient on you, young lady, since it is your first offence as Head Girl. I will give you only four strokes across the seat of your gym shorts. You can count yourself lucky, as it should have been six of the best!” The Deputy Headmaster snapped.

“Yes sir! Thank you, sir!” Nancy replied relieved that she was spared the maximum punishment.

Mr Steward opened the punishment book and entered the Head Girl’s details into the book, below that of Hellen and Kayleigh.

“Jones, Nancy, Upper 6A, Skipping gym class, four strokes of the cane, across gym shorts.”

The Deputy Headmaster got up and took the cane from its hook. Then he addressed the girl sternly. “Turn around so you face the window and bend over!”

Nancy turned and leaned forward, placing her hands just below her knees, as the Deputy Headmaster took up his position on her left side.

“Touch your toes, Jones!” Mr Steward snapped as he pressed the cane firmly against centre of the four foot nine inch tall girl’s bigger, fleshier bottom, covered in drum tight, thin, maroon gym shorts.

The Deputy Headmaster tapped the up-turned bottom a few times, followed by a swish, thwack as the first stroke landed just above the centre of her bottom. The redhead did not move or utter a sound, but Mr Steward could see how her bottom muscles tensed and relaxed as the sting spread along its red welt of  fire.

Ten seconds, and tap, tap, swissh, tthwackk, the second stroke fell just below the centre of the girl’s bottom, causing the girl to breath heavily for a few seconds and move her weight from foot to foot.

Twenty seconds went by as the Deputy Headmaster just stared at the girl’s bottom before there were three taps followed by a resounding sswwisshh, tthhwackk! The third stroke fell halfway down the bottom half of the girl’s chubby bottom, followed immediately with the final stroke; sswwiisshh, tthwaackkk!

Nancy straightened like a spring for a few seconds as she frantically rubbed her scorched bottom, then she forced herself back into position, with her fingers placed firmly on the tips of her white plimsolls.

The Deputy Headmaster waited a full minute before addressing the girl as he placed the cane back on the hook behind the door.

“Right, Jones, up you get and compose yourself!”

The bell rang to announce the end of the school day as the Deputy Headmaster sat back in his chair watching the poor eighteen-year-old Head Girl rubbing her stinging bottom.

“Back to the changing rooms and get dressed,” the Deputy Headmaster instructed.

Nancy turned and quickly made her way back to the changing rooms where she found she was all alone. She looked in the mirror and saw her bottom had four angry red welts covering the lower half of her bottom.

Late that afternoon, Hellen and Kayleigh met up at Kayleigh’s house and compared their marks in the bathroom. Hellen sported two red welts, while Kayleigh’s bottom was covered with six very angry looking red welts, with a bruise forming where the two strokes had crossed.

As James Steward drove through the school gates at 4.30 that afternoon, he was quite shocked at the thought he had to administer three canings that day, but also he felt a sense of accomplishment as he knew that word would get round the school that getting the cane was no joke.

The End

© Brian Melville 2019