Miss Henderson

[RebeccaShaw]

Miss Henderson

I sat sipping my coffee with a little dread at the thought of what delights this new week of teaching at the mundane oakwood academy would bring. Not that it was a bad school as such but like any other city center schools it had its problems. Just as I was considering whether I dare ring in sick my flatmate Ella walked in grinning and handed me a letter.

“Go on, open it, have you seen the name on the envelope, it's from Wolsey hall college,” she exclaimed.

I tore it open and looked in shock as I had been invited to attend an interview for the post of English teacher to year 7 at the prestigious private boys school. Never in a million years did I think with my limited experience would I be selected. Ella was almost as excited as me but then she giggled and reminded me of the urban myth that surrounded that school. Of course I was well aware of it but didn’t think for one moment it was true and even if it was it had no relevance to today.

The urban myth in question surrounded an alleged true account published in The Times newspaper in 1903. It concerned the first time the school had engaged a female teacher and it was said that the boys in her class had refused to show her any respect. The reason was that she had allegedly admonished a boy for crying when he got back to class after getting the cane from the headmaster. She admitted that she had never felt the cane but it could hardly be that bad. To cut the story short it was reported that she then agreed to take the cane herself to earn the back the respect of the class. The myth had continued that it was an established tradition that from then on all new female teachers had to demonstrate they could take a good caning in order to get respect from the boys.

I teased Ella that she was jealous and the urban myth was just that and a load of nonsense, she would give her right arm for the chance to teach at such an establishment. I was delighted and almost convinced myself I had got the job already and the following week at school went so quickly. The morning of the interview I decided to go all out to look as smart as I could but also try and give a little provocative touch. After all, the Headmaster was likely to be quite old and what old guy didnt like a flutter of the eyelashes and maybe a little glimpse of a stocking top and a flick of my hair.

I was nervous in the taxi and looked down thinking maybe the skirt was too short and the blouse a little too sheer as my bra was clearly visible through it. Perhaps I had put too much perfume on and my lipgloss was a little too red but it was too late now. The taxi pulled up outside the grand entrance gate and an old guy who introduced himself as the “Gatekeeper” greeted me. It was like something out of “Game of Thrones,” a Gatekeeper no less. The gravel on the drive made it a little difficult to walk in my high heels but thankfully it wasn’t a long walk. The large oak doors were pulled open by what looked like a butler but he was the senior house master and on duty for the weekend to take care of the requirements of the students outside class time.

“Ah, you must be Miss Henderson or is it Ms” he asked.

I replied that Miss is fine thinking it would fit better with the school heritage and did not want to appear contradictory. He led me through a narrow corridor and into a dimly lit room where an old rotund gray haired man sat behind a large desk. He smiled and instructed me to take a seat and proceeded to ask me all kinds of questions related to my past experience and then out of nowhere looked up and virtually offered me the position. I felt a little numb as he told me I had to undertake what he called a “Pupil Review.” He assured me it was a formality and just a way of engaging the students in the recruitment policy of the school.

With my head still spinning in disbelief and almost shaking at the revelation of how much the salary was, I was given directions to go to a room and ask for Jacob Myles. The place was like a maze and after getting lost a couple of times I found the room and could hear muffled conversations and outbreaks of laughter that was all too familiar when boys of that age got together. I knocked on the door and opened it as the room fell silent, several boys had game consoles and a few others were flicking on their mobile phones and some reading books.

“Er excuse me I am looking for err, Jacob Myles.” I asked rather politely and nervously.

“And who wants to know?” came the reply from a boy sitting by the window.

I stammered who I was and that the Headmaster had told me to come here, I could feel all the boys look at me and knew I was blushing a little for no reason. He calmly announced he was Jacob and I should have introduced myself first, as how were they to know I was a new teacher. For all they knew I could have just walked in off the street and been some foreign assassin and where was my visitor’s pass at least. One of the other boys took pity on me and told him to leave me alone couldn't he see that I was nervous already? They all smiled at my obvious discomfort and Jacob stood up and somewhat inappropriately put his hand on my arm to usher me out of the room.

“Right young lady we can carry out this review in here, in fact this might end up being your classroom” he sounded so amused. The old fashioned classroom was just like you would find in a Dickens novel with 12 individual desks in 3 rows of 4 then a large desk in front of a blackboard. Still feeling indignant about him having the audacity to call me “young lady” and the sheer nerve to lead me in here as if he was in charge I could feel my heart pounding. I stood almost like a rabbit in the headlights as he sat behind the large desk at the front of the class. In all that had happened in the last few seconds anyone watching would think he was the teacher and I the unsure, nervous and confused student. The only thing that contradicted that image was the age of us both, a complete mismatch of the situation.

“So I assume you have heard of the traditions of Wolsey Hall college” he asked.

My face instantly went red and I felt so absurd to be standing in front of the class almost getting admonished by this mere boy. I replied that of course I had heard the rumors and knew all about the “Urban Myth” which made him smile. I could feel my hands clasped in front of me and my palms sticky with perspiration and as I gave the hem of my short skirt a nervous tug down as he smiled again. I followed him with my eyes as he stood up and took a few paces to the black-board then almost gave an audible gasp as right next to it hung a long rattan cane.

“So does this look like an urban myth, or does it look real?” he asked as he placed it on the desk.

I couldn't take my eyes off it and knew he was just teasing me. I mean so what if it was a real cane, they had lots of ancient things in a building this old. I could hardly process what he was saying as he informed me that as part of this “Pupil review” I was to get six strokes and if he was satisfied with my “performance” he would recommend that the Headmaster engage me on a one month probation period. This was insane! The boy was hardly half my age let alone going to be one of my students.

“So take off your skirt and bend over the desk with your rump as high as you can or don’t waste any more time here.” he said in such a matter of fact way.

We looked at each other for a few seconds and I knew my face was bright red. He had an arrogant expression on his face and seemed so assured of himself and I knew I must look the exact opposite. I was praying that at any moment he would announce it was all some kind of joke and burst out laughing or something but no. He kept a solemn, almost focused look into my eyes. I kept flicking my own eyes to the cane and then to his face and all that ran through my head was the more than double salary they were offering and the opportunity to progress my career no end.

This was more than absurd and incomprehensible but I was actually considering going along with this outrageous charade. My hands made the slight movement from the hem of my skirt to the side and fumbled nervously with the two buttons above the zip. His expression changed and he looked satisfied and slightly smug at my actions. The noise of the zip being drawn down my tight skirt seemed to fill the room and I was shocked at how my eyes never left the cane. I was telling myself that five minutes of this torment would be so worth it for the benefits to the rest of my life. With a little wriggle and a fresh blush to my face the skirt was at my ankles. I tried not to look at him and quickly picked it up and placed it on the desk in front of him and put my hands in front of my lacy pink knickers.

He was silent as he looked me up and down and with just a little nod with his head at the desk I remembered the second past of his instructions. Oh god how could he be so calm when I was almost shaking visibly and just wanting to explode inside at the sheer disbelief of it all. I took a small step closer to the desk and leaned forward. My head was now a few inches above the smooth wood and I glanced up to see him smile and push my head right down gently so my face felt the hard surface. He took my arms and spread them to each side of the desk and told me to hold the edges firmly and not to move or we would start all over again. I could sense that this was not the first time he had done this and despite his age his confidence was absolute.

“Well done MIss Henderson. It's nice to see you show some sense and not whine like a baby about a few strokes of the cane on your bottom.” he sounded more amused now.

As he picked up the cane he stood and walked around the desk so I couldn't see him any more. He began to tell me of some of the childish tantrums and pleading some of the candidates have displayed when told to remove their skirt. He told me that the boys were each given turns to conduct a “Pupil review” and it was a badge of honor for them to show they had caned the prospective new member of staff. The word “Show” didn't really register any significance at the moment as I could just imagine the view he now had of my all too brief knickers showing practically all of my bare bottom now. I was then dismayed as he carried on to inform me that actually getting the cane was only a small part of actually being offered a position here.

“You see Miss Henderson, anyone can push their fat bottom up and take a few whacks but we look for more than that at Wolsey College,” he announced.

Before I had a moment to even understand what “More” could be I heard the “whoosh” of the cane whistle through the air and then loud crack onto the skin of my bottom and then a micro second later the intense sting and burn sear a line across my cheeks. I let out an audible gasp and felt the cold touch of the cane as this time he ran it up and down my bottom. I gritted my teeth as the cane left my skin and I could sense him draw it back then the familiar whoosh made me know what was coming. My hands gripped the desk tighter and the gasp was almost a muffled yelp this time. I eased my heels off the floor one at a time making my bum cheeks jiggle a little but it had no effect on easing the pain as such and I could hear hum tut in disapproval.

“Stop that Young lady.” He snapped. “What did I tell you about keeping that rump in the air, not shaking it around like some cheap tart.”

The audacity of him addressing me as “Young Lady” was hardly of any significance compared to his total control he had of the situation. Another hard, crisp whack had me sucking in a lung full of air and a concentrated effort to keep my bottom still and up as high as I could. My breathing was more emphasized now and a shudder ran through me as I felt his hand on my bottom. His fingers ran slowly over the hot, straight welts on my bum cheeks. After a minute of tracing the three distinct lines of fire he cupped my cheeks and even gave them a little shake. Oh how much he must be enjoying this, a grown woman at his mercy and a possible future teacher of his no less.

“So what is your first name Miss Henderson, it seems a little formal saying Miss when I am going to take your knickers down.” he said without trying not to laugh.

All I could do was whimper a pathetic sounding “Emma,” with no thought of refusing to answer him.

“Well Emma it hardly seems acceptable for you to call me Jacob when your bare bottom is up in the air like this, does it?” he mused.

His fingers were in the waistband of my tight pink knickers now and without thinking I lifted my hips from the desk to allow him to pull them down to just above my knees. I had my legs together but made even more of an attempt to keep them pressed as tight shut as I could to preserve whatever modesty I might still have. I sensed him step back and closed my eyes knowing what was coming next and the agony of another seering, burning stripe of the cane was not a surprise. My eyes still closed. I sniffed back a sob and knew what I had to say.

“Oh yes Jacob, Please may I address you as Sir from now on. I don't want you to be embarrassed with me not showing you proper respect.” I tried to sound so sincere.

Once again he put his hands on my bare bottom and even jiggled them a little. I thought I was getting the idea of what “More” meant now and I made extra effort to get my bottom high by keeping my head and my breasts pressed into the desk but arching my back to lift my bottom more with even my feet on tip-toes. I even let my legs fall open a little now and felt my knickers stretch between my knees. A sudden “swish” and a thud made me yell out loud but kept my position to the millimeter.

“Excellent Emma, you’re doing very well in this Pupil review, I am sure you can count so what would you like to say now?” he asked.

“Thank you for taking my knickers down Sir and giving me five strokes of the cane but please may I have another one.” I said, as if it was the most normal way to behave in a job interview.

I had gone this far now and if it meant getting the damn job I wasn't going stop this charade any time soon. The cane managed to find a place on my bottom not already burning and left another imprint on my cheeks. Yet again the sting was intense and accompanied by a shrill yelp from me. He gave me permission to stand up and rub if I wanted and didn't need telling twice. I hopped from foot to foot and clutched my bum with both hands. Gasping and walking around the classroom I tried to rub away the horrid sting from my bare bottom. It hardly seemed relevant to stop the boy seeing anything now and my blouse is not long enough to cover my bottom or my pubic hair.

“Right take your knickers off Emma, we can’t have you waddling like a duck when we go and show the boys the marks on your bottom can we?” he smiled.

I could feel my eyes open wide and he just shrugged at my response. I wanted to protest now but would it make any difference. He had already warned me about showing any sign of refusal and all I could think about was the word “More”. With a fresh blush to my face I tugged my knickers down and right off and placed them on top of my skirt on the desk. He seemed more than satisfied and with a curt command to put my hands on my head he walked over to the door and opened it wide. Out in the corridor I felt even more embarrassed and ashamed to parade around like this but the cool air seemed to take the edge off the heat on my bottom and replace it with a lovely warm glow.

It was a short walk along to the room I had introduced myself to the boys less than an hour before. I doubt in my wildest imagination would I have thought about walking into a room of boys with my hands on my head and my skirt and knickers off to show some vivid, sore marks on my bare bottom. I tired some deep breaths and told myself this was all worth it and Jacob could see me try to compose myself and with his hand on my bottom he whispered for me to take a moment and remember that teachers at Wolsey College were capable of “More”.

The door opened and Jacob marched in almost triumphantly, “Boys, Miss Henderson has something to show you all.”

My legs felt like jelly and I stood in the doorway. I could feel every pair of eyes look at me from head to toe and it was almost worse to have my hands on my head like some naughty little girl than to have my neat strip of brown pubic hair on show to them all. A few murmurs of approval and the odd comment on my stockings accompanied my steps to the middle of the room. I looked at Jacob and took another deep breath.

“Please Jacob Sir, may I show the boys my bottom? and how well you have caned it,” I asked politely.

He looked delighted and replied, “Of course Emma, get that fat bottom right up in the air and stay perfectly still.”

With the word “More” ringing in my head, I turned around and bent right over and reached down with my fingertips to touch the toes of my shiny black high heel shoes. My back was a little curved to keep my bottom up. I shuffled my legs wider apart. With a slight hesitation I eased my feet even further apart and then wrapped my thumb and fingers around my ankles and kept my legs straight. The atmosphere was electric as Jacob stood by my side and asked a boy called Sam to go and bring the Headmaster to see my cane marks. His hand was on the small of my back, pressing a little as he cleared his throat to speak.

“Go ahead boys, have a good feel of the new teacher’s bottom while I explain her rules for the next month.” he announced.

I was staring at the floor feeling numb as several hands mauled and squeezed my sore bum cheeks. Several times my cheeks were lewdly pulled apart and I could hardly concentrate on what Jacob was saying to me. Something about getting the cane at least twice a week from various boys. This was excluding a more severe caning in the gym at the weekend in front of boys and other members of staff and even some parents of the boys. Each Monday in class I was to ask if it was ok with the boys if I could teach with my skirt and knickers off. All the time more hands were pinching and even slapping my bottom now and making comments;

“I don't think her arse is that fat Jacob”

“Plenty of room for more lines though”

“Did she squeal much Jake”

“I'm gonna ask her to shave her pussy like Miss Jones”

“Yeah good idea we could do it in class”

This was all followed by mocking laughter and then a sudden silence and the boys stepped back. The familiar voice of the Headmaster gave me the reason and once again hands were on my upturned bottom. The touch was gentler but just as thorough. He evaluated Jacob’s technique and seemed pleased that most of the lines were consistent and well placed. A crisp, resounding slap brought me out of my dreamlike state and he told me to stand up and did I have anything to say for myself. Jacob moved his hand from my back to allow me to stand up and my face was really burning with shame now I had to face everyone.

“I am grateful to be offered the opportunity to teach at Wolsey College Sir, I will abide by all the rules and any requests the boys have for me Sir,” I hesitated.

“I am feeling a little hot Sir, would it be alright if I took my blouse and my bra off and had some more with the cane to help me get used to it. If the boys don’t mind?” I asked meekly.

Oh course the boys looked delighted not say surprised but the Headmaster gave a wry smile and looked down to my wide open legs. I am sure he knew exactly what was going through my mind, which was more than I did. He stepped back and paused before walking over to the blackboard and returning with a piece of chalk. The boys were transfixed as he handed me the chalk.

“I suggest three from each of the boys here should get you used to it, Miss Henderson. But I want you to write on the board what you think you need.” he informed me.

My mind was racing as I tried to quickly count the boys and got to at least eight. What had I got myself into now and how was my poor bottom going to feel after this. I approached the board and without looking behind me I wrote in large letters.

“MORE”

They were loud gasps and a few hoots in delight and as I turned I quickly unbuttoned my blouse and unhooked the clasp of my bra. I have no idea why but I actually climbed up on the large desk at the front of the classroom and on my hands and knees dipped my back to get my bottom up. Jacob walked up and looked into my eyes and grinned. The Headmaster announced he was going to get the employment contract for me to sign. I felt so nervous but at the same time I thought, This has to be the best job in the whole world.

[PhilMarlowe]

I enjoyed this first part and am looking forward to additional kinky adventures for Miss Henderson.

[MaireadM]

Fantastic start.
I am looking forward to more of her adventures