Monthly Archives: March 2018

Saint Helena High School for Wayward Girls. Chapter Two… ‘The New Member of Staff’

There had been a meeting of the ‘Board of Governors’ at Saint Helena High School for Wayward Girls. The success of my methods here, since we became an Academy of Correction has made it almost full.

I cannot cope, I have asked for help with discipline. I still intend to carry on when I can, but really, the school needs a full time Disciplinarian. Let me tell you about our choice.

The meeting went well, they backed me completely and unaminously decided that a room was needed to be fitted out solely for discipline, and a dedicated member of staff was urgently required to run it. A no nonsense expert in the art of corporal punishment. Interviews were held over the summer holidays, and we had lots of applicants, I feel we made an excellent choice in hiring a young lady named Miss Tamara Kenworthy.

And so it was that on the first day of the new term, that if you walked down the corridor to the reception.

…and looked at the staff notice board, you would see a new photo had been added, just below the photos of Head and Deputy Head, in a line of senior staff, the Heads of Department.

You would see this photograph of Miss Kenworthy, the ‘Head of Discipline’.

Quite an innocent looking photo of an attractive young woman approaching her prime. Tamara looked charming, and gentle.

There were a crowd of girls looking and chattering about  the photo, when all together they stopped, as Miss Kenworthy clip clopped her way to them in her red high heels and black business suit. They parted like the Red Sea as she walked to the notice board and unlocked it. She took the photo (shown above) out, and replaced it with this one of her holding a black, harsh looking punishment stick. Not a cane, but something altogether more sinister.

I was watching from the balcony which runs around the reception quadrangle, looking down. I was stood outside my office, the Headmaster’s Office. I nodded satisfactorily at her first dramatic move in ‘the Game of Discipline’ she had begun. We had chosen well.

The new photograph was better and conveyed the correct image, that of a no nonsense, strict disciplinarian, who knew how to wield a cane, a tawse and a plimsol.

She clip clopped her way back to whence she came, to a corridor, that housed her ‘Room of Discipline’, with its new sign ‘REPORT ROOM’. Because most girls who visited it would be ‘on report’.  A room that now had two chairs outside, and a stack of six more inside,  in case they were needed on a special occassion. On the right hand side of the door was a small stool, the humiliation stool, which would have to be polished by every girl who stood on it.

That little row of seats, and the stool had picked up a new name from the clever, witty, but very naughty girls of this Correctional Institute. From this day on it was referred to as…’Death Row’. In the first week of its existence some unknown girl stuck a piece of paper on the door, with a notice scrawled on, straight  from  Dante’s Inferno, ‘Abandon Hope All Ye Who Enter Here.’

Tamara took it off and had it framed, and kept it at her home, a keepsake she would value for ever, along with many others.

I asked her to come and see me, after her appointment, this was about a month ago. I gave her a budget to spend and a list of suppliers. She spent her time up until today, the day of the photo, setting up her room. I gave her complete freedom, it was her domain. She put desks in, for girls who had lines or essays to write, and an array of implements and apparatus.

Her first act was to go to one of our trusted suppliers, which was in a town just a few miles away. Here she handled the canes to get a feel for them and ordered two dozen of various lengths and diameter. Over the years to come she would make great friends with a Miss Alexander, who as you can see here, made excellent canes.

Slowly but surely her equipment came, including a thick, hard backed, leather bound punishment book.

Much of her time was spent alone, it was after all the summer holidays and the teaching staff were on holiday, she arranged the room to suit her needs.

All alone with the school quiet, she inspected her corporal punishment  equipment

The flexibility of the canes were perfect, and she began to have thoughts of making them wrap around the curves of  naked girl’s buttocks.

The room smelled beautiful, it had a new carpet and the wood had been freshly bees waxed by the caretaker. The radiators ticked, because the same caretaker had sent a memo to her saying  he needed to test the heating system. It was a rainy day, and for summer quite cool. The noise of the rain rattling on the window pains made her feel glad to be cosily settled in her room. She locked the door, and slowly walked around caressing the desks. She imagined the cool shock of the wood on a naked schoolgirls belly as she was draped over, bare bottom presented, knickers around her ankles.

She loved everything about spanking.

The thoughts developed into a little fantasy, a masturbation fantasy. She began to breathe deeply as she pushed her groin to the edge of the desk, rhythmically.

She straightened and her hands ran up her hips, gripping the hem of her skirt.

To reveal her delightful, see through, black knickers.

Which she pulled down. The cool air caressed her bottom.

She pulled her cheeks apart, and the cool air entered the hole of her bottom and made her take a sharp intake of breath as she realized how wet she was.

She christened her room of discipline and shame by self spanking her beautifully curved bottom. As she hoped, the room had near perfect acoustics. The crisp sound of the smacks filled the air. She closed her eyes, and her mind went back to her own school spankings. She recalled how she hoped that one day she would be delivering rattan to a bare bottom as the teacher was delivering it to hers.

And now, here she was, being paid to spank, and cane.

She saw herself, in school uniform, yet at the age she was now. In her mind she was an adult schoolgirl, in black and white, like the images she searches for on-line to aid her masturbation. The knickers she pulled down were not hers, they were her old large white school knickers.

She spoke to herself…”Bare your bottom for a spanking you naughty girl!”

She could see her reflection in the window and looked at herself, as she made a mental note to open the blinds to humiliate a girl. Nobody was around to see today, so she continued to look into her reflected eyes. “Present your bottom Tamara!”

Then she began to spank herself harder…

And harder…

And faster and faster…

Then she leaned back and fingered wet slit to orgasm.

She came hard and loud, not holding back, safe and sound in the knowledge that she was perfectly safe to do as she wished in her room…her beautiful room of pain and punishment.

The next few days saw her trying out various apparatus to punish the girls over. It also saw her to go to a local shopping mall, to buy a school uniform, like in her masturbation fantasy. She wanted to know how it felt, and how high gym-slips would ride up, and, she thought naughtily, behind her locked door she could dress up whenever she liked, to fulfill her private ‘naughty schoolgirl’ fantasies.

And so it was that Miss Kenworthy began to test out her equipment, with her hair in a pony tail like she wore at school, and a gym slip (a little short, but she loved it, and most girls at the school wore short ones anyway. She wanted to look like the girls she punished.)

She put two of the chairs from her stack back to back, which was how pupils at Winchester School were punished, and to this day the position is called the Winchester Position.

She stood before them, imagining how they would feel when she ordered them to kneel and bend, ‘knees and palms must remain on the chairs at all times’ she said out loud as she climbed on.

“Hmmmm, I like it but the bottom should be forced up more, maybe the elbows should touch.” So she tried that.

“Present your bottom higher girl!” She said to herself sternly, and giggled.

“Oh that is much better.”

She had been shopping in all sorts of places and could not resist a little wooden rocking horse. “This will humiliate the older ones when I tell them to get on it and rock, like a little girl, as I crop their naughty bottoms!”

She put the chairs away, and climbed upon the little horse, which she decided to call ‘Neddy the Punishment Pony’.

She placed her palms and toes on the base and rocked. “I think this could work very well indeed.” She said to herself. “Once rocking I could pick up the rhythm, whack their bottoms as they get to the rear end of the rocking and then WHACK! Send them forward again! Oooooh imagine one of those haughty ‘no it all’ types on this, before a group of other girls!”

She had mounted a real saddle on the little horse and as she rocked back and forth it excited her, she pressed down hard and galloped to orgasm. “I can see some submissive types rather likening this!” She gasped.

Also, as she moved, she discovered that her knickers had caught on the saddle. “Oh I say! What a lucky accident! I will use that to hold their knickers down.”

She galloped to a second orgasm, and was so wet that as she slowly rocked to a standstill, the draught created by the movement, blew cool on her sopping wet cunt… “Oooooh, that’s nice!” As she climbed off her love juice stuck slightly, and she looked at it stretching between the saddle and her swollen labia.

Miss Kenworthy decided not to wipe it off, in fact she decided there and then never to wipe any off. How satisfying it would be to rub her cunt to orgasm now and then on a saddle, stained with the pussy juice of young virgins!

Tamara watched it run in a trickle and dry.

The next thing she tried was something her Grandma had left her. An old towel/clothes airing rack. She liked a girl to have something to grip.

“Oh my! I think this will present the bottom well for a caning!” She bent over and gripped a rail.

“Oh yes Tamara, there will be a few wetting their knickers before their panties are yanked down on this!”

She told herself to get on tip toe.

“Oh my word, what a position, ooooh just imagine, waiting for that first whack, trembling, and your bum hole twitching away in fear!” She thought.

“Present your naughty bottom for twelve of the very, very best young lady!” She said to herself.

She tensed the muscles around her anus to make it twitch as if in fear. “Oh I hope I get some doing this!”

Then she pulled out a piano stool which she thought would be perfect for the kiss of a tawse. She had two, one broad supple one, and one thick, inflexible strap. “God I am going to make some of you squeal and beg for mercy!”

“Oh wow! If they try to grip their scorching cheek they’ll drop over! Same if they try to resist a blow. Ohhhhh Miss Kenworthy! You could bring blistters to a fine upturned rump on here!”

Her bottom had never been presented so well, she could feel the lips on her pussy open, she was so stretched!

Over the next days she tried out most of her apparatus, and also various places in the room to simply bend over, so she could find the place to stand for maximum swing.

She loved just bending over, she excited herself and her quivering quim time and time again, often giving herself a spanking and blushing cheeks.

The first day of term was approaching, she was getting excited, in more ways than one.

Something, alluded her. She needed the ultimate way of shaming and humiliating a girl. It was the Friday before the new term when she found it, a large mirror. To be known as ‘The Mirror of Shame’, she would punish girls before it so they could see themselves ‘get it’, and afterwards stand before it as she wrote a record of their punishment in her book of shame, the punishment record of ‘The Report Room’.

She placed it next to her store room, a simplistic minimalist place for the ultimate punishment and shame.

The first day of term arrived, she got in early, dressed in her favorite red and black.

Everything was in place, she caressed her implements.

She kissed her crop, for ‘good look’ and strode to assembly. On the way she stopped at the notice board and put a different photo in. She saw Mr.Jones the Headmaster looking down from the balcony outside his office, and smiled. He smiled back and nodded satisfaction.

Within days a steady stream of naughty bottoms found their way to her ‘Report Room’ to be dealt with. She was both surprised and excited at how quickly her punishment book was filling up.

By the end of the first week she was on the third page, as girl after girl came nervously to her door with a report card, and sat on the two chairs outside.

To be punished…

Some harshly, like Charlotte, on the left here, and her friend Sarah. Miss Kenworthy gave them both a real thrashing, Charlotte in particular making a huge fuss, screaming ‘I’m sorry Miss Kenworthy! Owwwwww please stop Miss Kenworthy, no more, please please!” But Tamara thrashed her bottom as she wriggled, as she did with them all, begging or not.

Tamara was in punishment heaven, bottom after bottom came through the door, to be bent over in any way she wished, to be punished by whatever implement she liked. How many girls she deterred she never would know, but one thing for certain, was that like all the other schools, most girls did not learn. The queue for punishment just kept the same, day after glorious day.

The two girls we saw just now, had to come back three days later, and again no mercy was shown, no matter how much they screamed and begged Miss Kenworthy to stop caning them on their already tender bottoms. This was her way, if they needed to be punished, they were punished… Simple!

The girls just kept coming…

Sometimes groups of them came, all bent over in a row.  To have their buttocks reddened!

Danielle here was a frequent visitor and spent a lot of time facing the wall, a projection screen, or a corner.

Or over a stool.

Girls soon learned to fear Miss Kenworthy, and being told they were being put on report,  meant something painful.

Yet it has to be remembered that these girls were at the extreme end of naughtiness, they were the wayward girls of Saint Helena High School, they were sent here because other schools could not cope with them. So all 878 of them, were naughty to the core…cheeky and defiant, rude and full of bratty behavior. Many were petty criminals, they were here to be sorted, and educated. Miss Tamara Kenworthy was at the ‘sorted’ end, paid to punish their naughty bottoms, in a much more severe way than main stream schools.

Her first week came to a satisfactory end. She loved it here!

And now some specific girls…see chapter three, and where they end up! A lot of the photos for this huge story are taken, as you will see in these further instalments…

….Saint Helena High School for Wayward Girls ~ Charlotte and Kate’s Stories.