The headmistress at Glenhurn
It was in the summer, at the height of the war, when our headmaster, Mister Dickinson, received his call-up papers. Although renowned for his firm guidance, Mister Dickinson was much liked amongst the boys, and was perceived as a great loss. His wife was immediately appointed Headmistress. This was the first major change. The second was when the local girl's school was bombed and it's female pupils arrived to continue their education at Glenhurn. We were moved from the most comfortable dorms, and our beds taken by the girl's. As all but a few of our masters had been sent away to war, it was seen as a stroke of good fortune that along with our new female pupils came a multitude of female staff. Those masters who remained were quite old and decrepit, and Mrs. Dickinson banished them to their cottages to pursue academic trivia.
Mrs. Dickinson was a Scot. She was tall and not of small build. However, that is not to say she was fat. On the contrary, we boys had often espied her in the early morning dew, running ten laps of the field, dressed in tight white gym shirt and brief shorts. Countless times we boys had knelt in a row, peeking over the window sill to observe Mrs. Dickinson's large breasts wobbling up and down in alternation. Our necks had twisted through a hundred and eighty degrees, goggle-eyed and gawking at her firm round bum as it passed by. Sometimes she would stop below our window and touch her toes, twenty or thirty times. Those of us who dared would poke our heads up for a glimpse of her breasts as they swung forward towards us, or her backside thrusting up into the air, depending upon which way she faced. In those days, it was usual for ladies to pin their hair up, but when exercising she never did, running round the field with a thick mass of red hair flowing behind her. As one can imagine, we boys spent a great deal of time spying on Mrs. Dickinson.
Our new Headmistress was, we guessed, about thirty five. It was only when, feeling the loss of her husband at the eastern front, and she sent for her daughters to come and live at Glenhurn that we realised she must be a little older, probably in her early forties. There was much speculation about the two new arrivals, Vanessa who was nineteen, and Vicky who was eighteen. Most of us had joked that they would be fat, or extraordinarily tall, or covered in acne, or would walk with a limp. It came as a great surprise to us when two tall, slim, girls were delivered by taxi one fine spring day. That night every bed in every boy's dorm squeaked and shuddered with ecstasy. I vividly remember dreaming about Vanessa and Vicky stripping me off in the hay and letting me suck their beautiful tits and rub their hairy slits. Unfortunately, I was rudely woken at seven am. for a laundry inspection!.
As we settled into our stride, acclimatising to the female staff and pupils, life seemed very good at Glenhurn. Vicky joined in lessons with the other pupils, whilst Vanessa's mother put her in charge of running the school stables. Every morning, the three Dickinson ladies could be seen riding away across the glen, bouncing excitedly up and down in their saddles. So much did I enjoy this spectacle that I used to make a point of going to the bathroom, standing on the toilet seat and looking out of the window in the direction of the glen so that I might catch a glimpse of them. As I looked, my cock would grow and grow, and I would proceed to rub myself to orgasm. Imagine my surprise when one morning a female voice behind me said, "What do you think your doing?"
I turned and fell off the toilet seat, and sprawled at the feet of Miss Appleby, the senior English Mistress. She looked at me, my pyjamas were open and my Willy was sticking out like a rampant stallion. Stepping over me, she craned to look out of the window. Turning back and looking down at me, she was puzzled at what it was that I was so desperate to catch sight of. Then it seemed to dawn on her. "My office - NOW!" she snapped. And with that, she grabbed me by the ear and lifted me to my feet as I struggled to replace my dwindling cock into my pyjamas.
"Ow!" I cried as Miss Appleby dragged me by the ear along the corridors. As we passed the girl's dorms, heads appeared around the doorways, and what seemed like hundreds of young, giggling females came to watch me being yanked by my ear lobe. I was bent double and my face was almost touching Miss Appleby's bum. This naturally excited me and I could feel my cock rising up once again. Miss Appleby open the door to her office and she deposited me face down upon her desk, "Hands out," she ordered. And she grabbed my hands and stretched my arms out straight across the desk in front of me. I gripped the edge of the desk and lay still, my head twisted sideways. As I watched Miss Appleby striding about, I managed to discreetly rub my willie on the comer of the desk. "Don't move," she commanded.
The moment she had left the room, I stood up and sighed with relief. I walked around, I tried to open the draws and cupboards to see what Miss Appleby kept in them, but they were locked. I sat in her thickly padded leather swivel chair, and twirled round and round. After about ten minutes I was bored. Slumping back in the chair, I sat twiddling my thumbs. My hand almost then automatically moved to my willie. I took it out and gave it a comforting rub, suddenly I spotted a straw basket in the comer, inquisitively I looked inside. On top there was a scarf, I pulled this away and dug deeper. There was a blue tennis skirt, a pair of gym socks, and underneath, the real prize, Miss Appleby's brassier and a pair of French style silk knickers. This was amazing to me. I picked up the panties and slowly put them to my nose. I sniffed them, then gently turned them inside out to see if there was any thing inside. I sniffed the insides, then rubbed them softly against my chin. By now my cock was as stiff as a yard brush, and I took it into my hands and began to masturbate. The door squeaked open, I dropped the knickers, flicked my willie into my pyjamas and stood up.
Miss Appleby stood in the doorway, momentarily dumbfounded. At her side was Mrs. Dickinson, and in the background Vicky and Vanessa. As I stood behind the desk, my heart thumped and I was breathing nervously. The four said nothing, but entered and closed the door behind them. Mrs. Dickinson and her daughters wore jodhpurs that clung tightly to the buttocks. Each was perfectly proportioned according to age, Mrs. Dickinson being the largest, then Vanessa, then down Vicky who was slim and curvy. Not knowing where to look, I stared downwards. My eyes met the sight of three pairs of black shiny knee length riding boots. Slowly I looked upwards, following the line of a thick leather plaited riding crop which was hanging by a loop from Mrs. Dickinson's wrist. She twisted her hand round and gripped the handle of the implement.
"Well," enquired the headmistress, "do you have anything to say for yourself?" My head drooped. "I thought I told you to stay bent over my desk," said Miss Appleby. "And what exactly do you think you were doing rummaging through my waste basket?" I could say nothing. "Well?" she barked. "Nothing," I replied softly, glancing up for a moment.
Vicky was grinning, Vanessa tapped her boot menacingly with a thin swishy schooling crop. "It would seem William," said Mrs. Dickinson calmly, "that you have been spying on myself and my daughters, and that you've also been playing with yourself. You've disobeyed Miss Appleby's instructions, and you've also been looking through her personnel belongings. I think you had better say something in your defence don't you?" I shrugged and smiled. "It's not funny," said Mrs. Dickinson. "Now you had better tell me the truth, have you been masturbating yourself?" Vanessa could hardly control her laughter and snorted into her hands. Mrs. Dickinson flexed her sturdy crop, "Well?" she demanded. "Yyyes, miss," I answered. "And you've disobeyed Miss Appleby?" "Yyyes miss," "And you've been watching myself and my daughters from the toilet?" "Yyyes miss." Mrs. Dickinson sighed deeply, "This is very, very, serious," she commented shaking her head. "I haven't had the need to use corporal punishment on a boy since I took over the head-ship of this school. But now...." She sighed, "I'm going to have to beat you, further more you will apologise to my daughters, and to Miss Appleby, and I think that it is only right that they beat you as well, do you think that is fair William?" I nodded hesitantly. "Do you have anything to say?" I shook my head. "Perhaps as a deterrent, we should beat you in front of the whole school, I will not have boys running amok in my school, upsetting the girl's in this way. From now on, I think we'll have to make sure that you have plenty of exercise in the morning to use up this excess energy of yours. I'll leave Vanessa to organise something appropriate. And perhaps a cold shower first thing will cool off your filthy thoughts. Vicky will supervise." I glanced up abruptly, Vicky, supervise me in the shower! I could hardly believe my ears. My eye caught hers as she gave me a furtive wink. "My daughters have been brought up around horses," stated Mrs. Dickinson. "They've seen it all before, and probably a lot more besides."
As I stood gaping forlornly at the floorboards, the headmistress her two daughters and Miss Appleby discussed details of my punishment. Rather than beat me in front of the whole school as first suggested, they decided as that I had caused an affront to all the female pupils and members of staff, I should receive a retributory thrashing for their eyes only. The boys of the school would hear soon enough about the punishment as a way of a warning. The four ladies e****ted me from the room, down the east corridor and along towards the small hall, which had been designated as the girl's common room. I shifted ashamedly in my pyjamas past some girl's on their way to breakfast. They giggled as I held up the slipping waistband on my winceyette bottom.
The small hall was, at this time still deserted. I appealed to be allowed to go back to my dorm in order that I might dress. My appeal was sternly refused and was followed by a furious lecture about cheekiness, insubordination and discipline. Mrs. Dickinson's face grew scarlet with rage, and I was promised an extra flogging. She cracked her riding crop down the side of her boot and ordered me to fetch up a desk and place it in the middle of the stage. As I walked down the steps, she bellowed at me to put a spring into my step. I hurriedly made my way across to a stack of desks. The women discussed the seriousness of my offences and the severity of the punishment that they believed would benefit them. Six strokes was mentioned and I believe increased to eight by Miss Appleby for disobeying her. This then went up to ten strokes as Vicky reminded the others that I had been caught rummaging in Miss Appleby's personal belongings.
Scurrying up to the steps with a desk held aloft above my head, the ladies turned to observe me. Suddenly in an instance the cord to my pyjama trousers gave way and they fell instantly around my ankles. Being in mid-step, my foot found itself caught, I shuffled and tried to hold my balance. I tripped and fell backwards down the steps, trying to keep hold of the desk. There was a great crash as I hit the floor, face first, and the desk landed right on top of me. Moaning in pain, I slowly slid the desk off my back. Aching and bruised, it seemed impossible to move. Without warning I felt an enormous whack across my posterior and instinctively put my hands over it. Looking up, I could see Mrs. Dickinson and the others towering over me, as in slow motion, I saw the headmistress raise up her riding crop, then swish it through the air. I wriggled as it caught me on the bottom. "Get up," she commanded in a controlled deliberate voice. Crawling forwards, a tear rolled down my cheek, I slowly pulled myself up onto my feet. "Pick up that desk and get it on the stage at once," she commanded. Yanking up my trousers, I grabbed the desk and ran onto the stage. A conversation ensued between the ladies about exactly where the flogging desk should be placed in order to give all spectators an adequate view. I picked up the desk and moved it, then moved it again slightly to the right. Then to the left. Then forwards. Then forwards a little more. Mrs. Dickinson took up a suitable position sideways from the desk. She brought her riding crop down onto the desk with such a ferocity that I thought she might break one or the other.
Using Vicky as a model for positioning, Mrs. Dickinson bade her daughter to bend over the desk with her posterior facing the main hall. By way of distancing her strokes, she held out the crop at arms length and rested it on her daughters pert bottom. With slow mechanical swings she moved the crop through the air, up behind her head and placed it down onto the girls bottom. This she repeated several times. Seeing Vicky's backside thrust into the air against her tight cream jodhpurs, set my pulse racing and my willie rising. Mrs. Dickinson made a final judgement on her positioning and brought the leather crop down onto Vicky's posterior with a soft thwack. Vicky yelped and her hand swung round to rub the point of impact. Vanessa smiled, but the younger s****r was not amused.
While the females went off for breakfast I was ordered to stand facing the back of the stage, with my arms outstretched at my sides. Vicky placed a book on my head and I was told that if I dared to move a muscle or talk to anyone, the severity of my punishment would be increased. Three riding crops were left in a row on the desk before me as a reminder of what was going to happen to me. After standing silently alone for what seemed like an age, I heard footsteps approaching and girl's voices. Without moving my head, I glanced to my side and saw a group of about half a dozen senior girls enter the hall. With bemused expressions on their faces, they came up onto the stage to see what I was doing. Having questioned me without response, the young ladies decided that I was either mad or stupid and turned their attentions to the crops on the desk. One of them, Elaine, a tall blonde, picked up Miss Vanessa's long thin schooling crop. She gasped a little as her fingers ran along the length of the delicately plaited black leather, presumably imagining how much pain and damage such a crop was capable of. Very soon Elaine and her chums had surmised the connection between the three crops and me.
"They're going to beat him," announced Elaine. She delighted in taunting me with it while the others looked on and laughed. As I maintained my bolt upright position in order not to dislodge the book from my head, Elaine put her hand down the back of my pyjamas and squeezed my cheeks. My face was red hot with the embarrassment. Her soft hand rubbed my buttocks, then slid slowly round towards the front. Her fingers fondled my testicles and gently squeezed around my now throbbing member. She played and toyed with me, an act that I was totally powerless to stop, my penis bursting free of my pyjama trousers as if in a crazed bid for freedom. Elaine whisked her hand away from my throbbing rod and turned abruptly as she heard the Headmistress approaching , hiding her hand behind her back as if to conceal her guilt. Elaine's sudden movement made me shrink back, and as I did so the book slipped from my head. After all that time, the dammed book had to slip now! I tried to catch it in mid- air but failed.
Mrs. Dickinson, now dressed in her usual blue pleated skirt and austere white blouse, strode briskly towards me. Her daughters and Miss Appleby also changed for school work followed. The second Mrs. Dickinson spotted my stiff cock poking out of my pyjamas, she snatched up the first crop which came to hand and cracked it down across my rigidness, sending paroxysms of agony down my shaft and causing my balls to contract, my penis shrinking immediately, the pain shattering and I gripped the poor thing as it pulsated in my hands, it was hot and glowed like rolled steel. The Headmistress snatched the back of my neck with iron determination and rammed my head down onto the desk with a thud. I lay prone across the desk as she angrily ordered Elaine and her friends to run around and tell all the other girls in the school to congregate immediately in the assembly hall.
As I waited there in that hapless way, awaiting my fate, Vicky made a point of moving in front of me, and lifting her leg up onto the desk, hitching her skirt up around her thigh and adjusting her suspender belt. The effect was electrifying, all pain in my throbbing penis suddenly turning to pleasure, and my stiffness started to return. She raised her other leg and offered me an eyeful of her thigh and suspenders once again, whilst giving me a seductive smile and a wink. Naturally as soon as her mother looked around she stood modestly with both feet firmly placed on the ground, looking as though butter would not melt in her mouth. The bitch, she had made me rampant my cheeks rushed as my pulse raced into my now engorged member. In my growing dilemma I panicked, and desperately tried to quell my lust by pressing my stiffness into the edge of the desk, thinking this would reduce me. Unfortunately the pressure and pain of the desk made me burst as it dug deep into my prick, and in full view of the assembly hall I experienced the most intense pleasure of my life so far, and I shuddered as a warm dampness spread over my belly; unfortunately this did not go unnoticed.
Mrs. Dickinson cringed as her hand gripped my neck and I was hoisted to my feel I thought she was going to explode with rage. My crutch was dark and damp, and there was no hiding the fact that I had experienced pleasure while under discipline and in front of the assembled girls. Mrs. Dickinson flipped and my head was bashed hard down onto the desk top repeatedly and it seemed as though she would pull my hair off by the roots. Mrs. Dickinson's voice was screaming in my ear and I could see stars. Finally it stopped and I lay still, my head spinning.
"Girl's, I am sorry to disturb your breakfast" I heard the headmistress say, "but we have here one extremely naughty and wicked little disgusting worm of a boy." The contempt in her voice was not disguised, "who thinks that spying on ladies is an acceptable pastime. My daughters and I, and Miss Appleby, are here to teach him a most educational lesson in manners and proper behaviour for a young gentleman. I would like you all to think of this lesson as being delivered on behalf of every young female pupil and ladies of the staff in Glenhurn College. This is for you." I braced myself and waited I knew this was not going to be good, I waited..
Nothing happened, I was then aware of slim fingers fumbling about my waist, a titter went around the hall as my pyjama bottoms were lowered from my waist, and across my bottom, then down my thighs and left to settle around my ankles. The humiliation was unbearable, I felt like dying as my cheeks were exposed to the gathered femininity in the large hall, some younger than myself, I was mortified. A crop, the hefty crop which Mrs. Dickinson preferred, was stroked laterally across my tender white virgin buttocks, then pressed firmly into my flesh to give it weight and meaning. It remained for some time; the wait was cruel. Mrs. Dickinson knew how to increase tension, and this was going to have meaning. I felt the crop being drawn and knew that it was on it's journey up, up around Mrs. Dickinson's curvaceous bosom, past her fresh natural complexion, along its arc high above, and back behind her head, the tip mingling with the curls of her shiny red hair. In terror I clenched my cheeks as tightly as I could, then nothing. My fingers twisted hard against the desk top, I tried to swallow but my mouth was dry. I gripped harder but nothing came, the wait was killing me. I thought of stealing a look over my shoulder, then just for a moment I relaxed. Mrs. Dickinson caught her moment THWACK! I'd been hit a peeler. A mass gasp went up from the girls, I screamed with pain, and grabbed at both my cheeks while shooting bolt upright hot fiery pain searing through my white flesh. Mrs. Dickinson grabbed my wrist roughly and f***ed it back across the desk, then likewise with the other wrist, I could hear myself whimpering. "Get your hands down," snapped Mrs. Dickinson. Something inside of me couldn't let her beat me again, and I placed my hands once again across my burning rear. She tried to pull them away but I resisted. The next thing I knew there were sets of hands grabbing at my arms and wrenching them across the desk. I could smell soap and perfume as I grappled. Finally I could struggle no more as a dozen pairs of hands held my arms tightly outstretched. As I shook my head in wild resistance, I could see Vicky hoisting her bum up onto the desk in front of me, she raised her bum up into the air until it was directly above me, then slowly lowered herself. The pressure to the side of my head was dreadful, my whole face was squashed like a tomato under the full weight of her. Elaine then decided to sit on my back. From their point of view I think they must have believed they had me as helpless as a stuffed turkey, but I still had my feet, I let out a fluffy of kicks with both legs. When finally I had inadequate strength to struggle any more, I felt the sturdy crop rubbing once more against my arse.
"You pansy! Take it like a man!" hissed Vicky into my ear, her pert breast rubbing gently against my sweaty shoulder, "you've just made the biggest mistake of your life laddie boy," and she was right. I received ten strokes across the bare arse from Mrs. Dickinson, ten from Vanessa, ten from Vicky and ten, the most horrible, from Miss Appleby. Forty hard strokes administered with riding crops. Apart from the floggings, I also had to face icy cold showers and strenuous exercise, strictly supervised every morning. The Headmistress ran a stern regime at Glenhurn, but we learnt respect and discipline, and respect for the female sex..