The Headmaster’s Room Ch. 01


This story is in three parts and begins in 1985 when I was 18 and finally ends last year.

“Miss Simpson! Go straight to the Headmaster’s room now!” Mr. Flanders shouted as he pointed to the Religious Knowledge classroom door. I shrugged my shoulders and slowly made my way to see Mr. Skinner for the third time that week.

With hindsight, at that time of my life I was a bit like a female Marlon Brando in ‘The Wild One’. Q: “What are you rebelling against?” A: “What have you got?”

I was constantly in trouble; smoking, smart-mouthing teachers, fighting, wearing too much make-up and my skirts were always deemed to be ‘too short’.

As I sat outside his office I recognised the voices of a couple of boys from the year below me through the closed door as the Headmaster lectured them. After a short silence he bellowed, “Bend over!” I edged nearer the door and soon heard the ‘swish-swish’ of his cane; each stroke followed by a ‘crack’ as the stick struck teenage flesh then there would be a grunt or a cry from the recipient as Mr. Skinner dealt out our Grammar School’s ritual punishment. Thankfully as a 18 year old girl in the 6th form my reprimand would be no more than another lecture and detention or at worst some form of ‘community service’ where I would have to look after some of the younger kids during morning break or lunch-time.

After a couple of minutes I could hear the boys snivelling as their lecture continued followed by Mr. Skinner brusquely telling them ‘to get back to class and send the next person in.’ I sneered at the so called ‘tough guys’ as they walked past me with tears in their eyes.

Still red-faced from caning the boys, the Headmaster shook his head in despair; “Lisa Simpson; why am I not surprised that you’re back to see me?” he sighed as I sauntered into his study. The room had its own peculiar stale smell which I would never forget; wood polish, musty books, Brylcream and ink. While I explained why Mr. Flanders had sent me out of his class; the Headmaster read my report card; although he must have known it off by heart as he’d read it so many times in the last year.

“Miss Simpson…you were once a good pupil…glorious future…buck my ideas up…yadda, yadda.” He droned on and on so much I began watching some boys playing football out of his window.

“Miss Simpson!” He bellowed, I turned to see him standing beside his desk looking furious in his black gown and mortar-board, “Listen to me when I’m talking to you!”

I nearly shat myself with fright!

“I’ve had enough of your insolence, hold out your hand.” He growled.

Shocked; I did as I was told; holding my arm and hand as straight as possible. The mersin escort tall, fat-faced man stood a couple of feet to my side. As usual the smell of Skinner’s mouldy smoke covered clothing and greasy hair filled my nostrils making me feel slightly nauseous. Without warning he drew his arm above his head and instantaneously brought the end of the bamboo rod down onto my fingers. I squealed as my hand retracted under my arm pit for comfort.

“Again!” He hissed as my fingers throbbed. “Hold your hand back out!” ‘Swish’ the cane stung my fingers a second time. “One more,” He told me as he raised my hand upwards with the cane.

I’d never felt pain like it before, as the cane hit my fingers for a third time making them swell and go bright red. Tears were now streaming down my face as Mr. Skinner returned the cane to a box containing another dozen or so bamboo and willow rods in the corner, then sat behind his large desk.

“Hopefully, Miss Simpson, you’ll have learnt your lesson and will now behave like the rest of the young ladies in this establishment or…if you continue to misbehave like a boy… I will have to punish you like a boy!”

Exactly a week later I was sitting back outside his room with four fifth form boys, as we’d been caught smoking behind the gym by Miss. Bouvier; a wizened old witch from Biology.

“The Usual Suspects I see,” Mr. Skinner sighed as we lined up in front of his desk. Yet again we had the usual lecture about our health and school rules as he slowly and meticulously chose a cane to dole out his punishment with. “I’ve told you all before what would happen to you, if any of you, and I include you…Miss Simpson, were brought before me.” He prattled on as he finally made his selection of a cane by ‘swishing’ it through the cold air. “Every one of you, bend over.”

I turned to look at the boy standing next to me. We were incredulous and couldn’t believe our ears. Surely he only meant the boys. The others all turned around and touched their toes in preparation for the forthcoming punishment. I stood still just staring into space.

“Miss Simpson?” The Headmaster looked at me and pointed the cane towards the boys, “What are you waiting for?”

Bart and Millhouse began sniggering as I blurted out, “But Sir…I’m a…girl!”

“Yes Lisa you are, but as I told you last week, if you continue behaving like a boy you must be punished as a boy. I can’t make exceptions.” The Head told me.

“Yes sir,” I sniffed as I turned away from him and bent forward.

He began at the far end of the line; each slow deliberate ‘swish’ of his cane bringing an agonized groan from the kocaeli escort boy on the receiving end. It seemed to take a lifetime as he calculatingly lined the rod up against each teenage backside so as not to hit the same spot twice. I was sweating with anticipation and my stomach was turning somersaults as each boy received six painful strokes of the rod before being sent out of the room until I was left alone still bending at a 90 degree angle.

As Millhouse, who had been standing next to me, stood up he winked at me through tear stained eyes and mouthed, “you’ll not really get caned – he wouldn’t dare.”

“I’m sure your little friends will presume that I will relent and give you a softer punishment; don’t you think?” He twirled the three foot cane between his fingers, “But you and I both know that you must be punished in exactly the same manner. Don’t we, Miss Simpson?”

“Yes sir.” I sighed at the thought of my impending chastisement.

“Stay where you are Miss Simpson.” Mr Skinner said sternly as I began fidgeting because my back was aching as the Headmaster changed the thin cane for a thicker one. I soon realised that my grey pleated skirt, which earlier in the day had been hiked about 4 or 5 inches above my knees, probably wasn’t covering my modesty anymore and he was now getting a good view of my pink flowery, non-regulation, knickers.

I sensed that his breathing was getting heavier as he tapped my ample backside through my knickers with the bamboo rod. “Now, it wouldn’t be fare if your punishment was less severe than the boys; would it Miss Simpson?” He whispered as he slowly ran the cane along my quivering buttocks.

“No sir,” I replied as I gripped my knees in readiness.

“Touch your toes then,” he coughed.

“Surely the dirty bastard won’t really do it because he’s getting his kicks looking at my arse!” I thought as I gripped my ankles knowing full well that my skirt must be nearly around my waist by now and my thin cotton knickers would be stretched tightly over my ample arse.

You have to remember that at 18 I was now in the first flush of womanhood and my teenage body was beginning to soften and fill out. I was quite tall for my age (5ft 6ins) with short brown hair and a ‘moon-face’ and had a 32b bust. All of the hockey and netball that I played had given me a bit of an athletic physique with a flat stomach and long thick legs but I was also ‘pear shaped’ – meaning that I had (and still have!) a big arse!

The tension was becoming unbearable as he lined the three foot, thick bamboo rod up along my generous bottom, slowly and gently sliding it along the white frilly samsun escort elastic on the legs of my knickers like a violin bow. My heart was now thumping and I soon realised that I was getting ‘hot and tingly’ between my legs as my Headmaster’s eyes lustily viewed my knickers and arse.

“Are you ready Miss Simpson?” The Headmaster finally asked as he pulled the cane behind his back.

“Yes Sir!” I whispered through gritted teeth as I braced myself for the impending pain. ‘Whoosh…CRACK!’

“SHIT!” I squealed as the cane struck my thinly covered arse making it shake.

As he drew his hand behind his back a second time I told myself that it hadn’t hurt as much as I’d expected.

“You can have another three for using foul language!” He grunted as the cane landed again – ‘WHOOSH…CRACK’. It bloody did hurt this time and the third and the fourth times. Tears were now filling my eyes and I made whistling noises through gritted teeth each time the cane had made contact with my arse but I wasn’t going to break down in front of him. Never – ever.

“You can …stand up now…that…should be…enough…to teach you…a lesson.. for today.” The Headmaster panted when he pulled his flowing cape tightly closed in front of him as he dropped the cane on the floor and swiftly walked back behind his desk. “Off you go now,” he waved me out of the room, his face now so red I thought that he was going to burst as he muttered, “come back on Friday lunchtime and we’ll finish …your punishment…then.”

Thankfully there wasn’t anyone in the corridor as I ran crying to the girls’ toilet to inspect my burning flesh. Once inside the cold tiled room I pulled my knickers down and half sat on a wash basin to inspect the damage in the cracked mirror. Both cheeks were red raw and you could see the four separate lines that his cane had made. My whole arse was throbbing but I couldn’t resist touching the sore welts. I didn’t know why but the pain was absolutely delicious as I ran my finger tip then the nail along the thin lines making them hurt even more than before.

Even now, 30 years later, I can’t remember making a conscious decision to do what I did next, but I quickly found myself locking a cubicle door and pulling my knickers down to my ankles and viciously rubbing my sticky inflamed clit as I rubbed the stinging lines on my chubby cheeks with my other hand. Within seconds I had the most powerful orgasm of my young life!

I leant trembling and gasping for air against the graffiti covered wall as I heard the school bell ring for a change of lessons. I was in a daze for the rest of the afternoon – and struggled to get comfortable on the hard wooden chairs as my arse was still so sore! As the day progressed, my friends all wanted to know what had happened as I had been a long time and obviously been crying; but for some inexplicable reason I didn’t tell anyone that I had actually been caned. I made up a story about being threatened with being expelled, which they all believed.

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