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(It was late autumn of 1960 and I, David Shaw, was 20 years old and was following my hobby of bird watching. I had unfortunately been detained by Amelia Wiff-Naseford, headmistress, for being an alleged ‘Peeping Tom’ in the grounds of ‘Dentwood Finishing School for Tall Girls aged 18 to 20 years old’ one Friday. There were 120 girls registered at the school. Clearly I was not a so called ‘pervert’ but I could not prove it.
I had decided not to get the local police involved by agreeing to submit myself to the traditional ‘Punishment Rules of the School’ as applied to ‘Peeping Toms’. This involved being stripped naked and spread-eagled on the headmistress’ study carpet, and tethered with ropes and leather straps to metal rings set in floorboards at each corner of the room. I was then required to orally pleasure the ‘whole’ school. This is part twenty of my sorry tale.)
Following a ‘night of passion’ with Celia the school secretary, I woke early on Monday morning with a massive erection. I lay there watching the breathing naked woman lying on her side with her back to me. Her shoulders were only just covered by the duvet and I reached over and kissed her on the neck. She groaned and I slid next to her and eased my huge penis against the dark rounded cleft between her buttocks.
I pulled her heavy cheeks apart and slid my penis between them, and released her fleshy globes so that my manhood became well and truly trapped. She stirred but did not wake. I lay there for a few minutes on my side savouring the exquisite pressure that her cheeks were exerting on my most sensitive part. In the half light of dawn she smelled of dried sweat and perfume; I did too. I once again became intoxicated with this woman who was at least thirty years older than me.
I pushed my penis against her, extracting as much sensation from her given that she was asleep and apparently oblivious of my movements.
I decided that I needed to ‘come’ so started to gentle rub against her, allowing my foreskin to be dragged backwards and forwards over my glans using purely the suction and friction of her skin which held me. I carried on like this for several minutes until she turned slightly and groaned and stuck out her arse even further towards me. I held her hips as I increased the pace of my thrusts. By this stage she was awake and had clenched her buttocks tightly in an attempt to grip me firmly. It worked well as now I could feel an orgasm welling up inside me. I was very close and wanted the millisecond at the brink to last forever. It didn’t and I grasped her waist with both hands and brought myself off in several powerful jerks. The sticky slime filled her buttock cleavage and, as I pulled out, I kissed her smooth silky shoulders and neck.
She rolled over and we kissed, and within half an hour we were making love again.
After breakfast in her flat she called the headmistress on the internal telephone and was told that I, the Peeping Tom, or just plain Tom, should be brought to her study at 10.00am where the rest of Class 2B would be waiting.
At the appointed hour I turned up wearing Celia’s kimono and was greeted by very bad mocking Japanese impersonations from the girls who giggled and tickled me unmercifully as we waited outside the head mistress’s office door.
“Ah so, welly honabell Pleeping Tlom to do honabell service to young Blitish flinishing school girls….”
“Come in girls,” bellowed Miss Wiff-Naseford from behind her desk. She looked incredibly hung-over and wore dark glasses to hide her bloodshot eyes.
“Ah Tom, pleasant night with the school secretary?” she enquired and I replied that it was very comfortable, trying to avoid her gaze.
“Plenty of sex then Tom? Celia’s only working in this school because she has been banned by the British Finishing School Trust from working with men. Her record of previous sexual misdemeanours is as long as your err…very long…very long indeed, ahem.” She continued as the girls laughed and stared at the bulge under my kimono.
“Off with your clothes Tom, we’ve got quite a few to get through today,” she cooed summoning Matron to help her tie me down.
I had not seen Matron for ages and she winked at me as if she knew that I had spent the night with the middle aged nymphomaniac secretary, Celia Raines. She appeared slightly jealous. I was surprised.
“I knew you would end up in bed with her, she’s just dreadful with men. She’s on permanent medication you know, we put it in her tea,” she whispered to me as she adjusted the leather straps and ropes. “Goodness only knows what she would be like if she stopped taking them,” she smirked and winked again. I liked Molly though, I thought.
“They’re not too tight for you are they?” she asked me, tensioning the buckles so that I once more lay on my back, arms and legs outstretched, naked with a rampant erection already seeking sexual relief.
Molly squatted down in front of me and slid the narrow six-inch cushion under my head. I diyarbak─▒r escort stared lecherously up her uniform skirt at her thighs which bulged out above her black stockings. I was drawn to the small damp patch in her satin knickers. She saw me and murmured that I could have her whenever I liked. My penis twitched dramatically at her words and she patted my face before leaving.
The rest of Class 2B were fidgeting and looking restless. I sensed that some of them would rather be somewhere else. I had reached the stage where I felt the same way too. These punishment sessions had been going on far too long. Surely when the punishment had been dreamt up in 1889 there could have only been a couple of dozen tall girls at the Finishing School, if not in the whole of Great Britain. This was taking far too long.
“First girl please,” said Miss Wiff-Naseford from her usual place, behind me on the low leather arm chair.” Ah, yes indeed, Alice Spears isn’t it? And your mother is a painter if I recall, step forward dear.”
A very lively looking suntanned girl with black hair crossed the room and stood by me.
“Now Alice this boy, Tom, here has been caught peeping. In fact he is a Peeping Tom,” she continued, “and we all have to punish him, the whole school, do you see?”
It was plain by the lack of response that Alice did not understand. I looked up at her. Her three-inch high heeled court shoes shone brilliantly in the morning sun, which streamed through the study window. Her smooth black stockings disappeared under her knee-length plaid pleated school skirt, which in turn disappeared under her grey v-neck sweater. She looked young and stunning. I watched her breasts bounce slightly as she asked the headmistress the obvious question.”
“So what are we supposed to do to the Peeping Tom exactly?” “Well sit on his face, of course,” she replied, suddenly remembering that every class had to be told what to do.
“Well how does that punish him? He would clearly enjoy it, surely?” suggested Miss Spears.
“Yes, yes, yes he does enjoy it, don’t you Tom?” she said aiming a kick at my face, “but he becomes very frustrated, very frustrated indeed, because he can’t relieve himself, by…err…you…know, masturbation,” she concluded.
“Oh I see,” said Alice, ” So he pleasures us, but cannot pleasure himself, so as time goes on he feels more and more frustrated,” she nodded in realisation.
“Precisely girl, you’ve got it. I hope all you other girls understand now,” the mad head teacher barked across the room. “Make him feel sexy but don’t touch his willy,” she emphasised curtly.
“Now girls when you sit on the Tom you clearly need to take your knickers off, so when I ask you to step forward you’ll stand next to him, drop your pants, then squat on his face?” she said peering through her dark glasses.
“Now are any of you having a period, no, good heavens this must be a record, remember to let the Tom lick you between your legs. Do not be shy; we are all girls together aren’t we?”
I thought again that I was merely an instrument of pleasure and that this business of them ‘all being girls’ made me feel sexless. I felt as if I was a smooth piece of wood and not a person. ‘All girls together’ indeed.
“Come on Alice, slip off your knickers,” said Miss Wiff-Naseford now clearly raring to go.
Alice waved down at me and smiled, then walked around me staring at my penis which was flaccid at hearing Miss Wiff-Naseford’s previous outburst.
Alice clearly had the right idea as she bent over and shook her pert buttocks over me, flicking her pleats from side to side. As soon as I saw the delicate lace of her petticoat I felt my penis lengthen and become engorged. Her underskirt was so feminine. There were tiny flowers and swirls of foliage as well as flounces along the hem.
She walked over me several times then stood above me staring down into my eyes.
She straddled my waist with her feet and shuffled slowly towards my face. At each step I could see more and more of her legs, first her knees, then her thighs, then her stocking, then her stocking tops then her inner thighs.
Finally she lifted her feet over my shoulders and placed them on each side of my face. I stared up her skirt almost shaking with anticipation. Slowly she squatted on me and immediately the smell of warm vagina swept over me. My nose entered her outer lips which were surprisingly cool and fleshy. I pushed out my tongue and slurped my way into her.
She smelled of musk but there was also a sharp tangy odour too. Soon she was rubbing herself up and down my nose. We quickly established a rhythm which, over many minutes, became a jerking wild mass of thighs, petticoats, shoes, vaginas, pleated skirts with my face somewhere in the middle.
The head teacher was clearly enjoying it as I could hear “Go on girl, wipe yourself all over him, that’s it, lots of juice, go on, go on.”
Tens minutes of constant clitoral tonguing brought on a series of frantic jerking diyarbak─▒r escort bayan and finally a shuddering deep orgasm from Alice, who emerged clearly shaken. In fact she was moved to tears and had to be hugged and kissed by her classmates. Once again I felt that I had done my part ingetting through this ghastly punishment.
Cheryl Raven stepped forward and pulled up the back of her school skirt, pushed down her knickers and stepped out of them. She had to be the first of many to drop her urine soiled panties on my face. I could have complained at such rudeness, but smiled up at her and nudged them off me.
Cheryl was another tall, truly big girl.
Everything about her was curvaceous and Rubenesque.
Her thighs appeared inflated, and her bottom was massive. Fortunately she was fairly light on her feet and I initially was wary of her four-inch spike heels which came dangerously close to my face but did not actually touch me. She wobbled her breasts at me in a faintly Burlesque manner which perked up my penis but not sufficient for an erection. I watched her shimmy her hips then step over my face and stand above mewith her legs wide apart. She appeared like an Amazon towering over me and my penis then rose in appreciation. She stared down and I then began to panic. Her pendulous arse seemed as if it would swallow me up, but I had no choice. I told her to sit on me slowly as I did not want to end up hospitalised.
She lowered herself gently onto my face. All around me bulging flesh hung down. Her stockings gripped her flabby thighs so tightly that I thought they would be torn apart by the pressure from her skin. Her thick suspenders appeared to be fully taut and dug into her thighs. It looked as if everything about her was large. She dropped, then rearranged her skirt pleats and petticoat over me so that I couldn’t see her face and only was vaguely aware of Miss Wiff-Naseford behind me. I stared spellbound at a pair of vast fleshy labia surrounded by fine brown curls.
Her inner lips glistened in the darkness under her skirt, and it was like a rare an exotic equatorial fruit. She shuffled forward, opening her legs further, and pressed herself firmly against my face. The stench was incredibly strong. It was a combination of sweat, urine and dribbling cunt slime. Then it began. On her heels and toes she rocked her heavy body over me, sliding her protruding lips over my nose and mouth. Backwards and forwards she slid over and over again. My neck moved with each sweep. She continued slowly but then began to speed things up.
I heard the headmistress tell her that she was ‘delightfully chubby’, but I did not think she appreciated this comment as she slid over me more firmly as if taking it out on me. I felt helpless and pulled and strained at my ties in an attempt to lessen the impact from each sweep. By now her vagina appeared to flood open with sexual secretions and my mouth and nostrils were beginning to fill up with her spendings.
“Have you thought of dieting? Cheryl dear,” said the insensitive old hag.
“No I have not thank you, I am happy with the way I am,” grunted the large schoolgirl sliding across my face more aggressively.
Two fleshy hands held my head as her slidings degenerated to frantic jerkings.
I now was in serious trouble. My face and her vagina were so covered in lubrication that they appeared joined. Suction had been created by her cavernous flaps against my nostrils and I could hardly breathe. I couldn’t cry out either as my head was being jerked from side to side so violently. I watched the loose folds of flesh gripped by the waistbands of her petticoat and suspender belt pulsate above me. Her skirt and petticoat rustled together and the trapped smell was horribly intense. I tried to tell her to stop but her labia prevented it. I couldn’t even move my head to one side because her sweating thigh skin gripped me. I think this was probably the worst experience of the past two days, matched only my being sat upon by the two cleaning women. My penis felt as if it was made of reinforced concrete it felt so hard.
Eventually her jerking slowed down and her movements became little short brutal painful thrusts as she squeezed every ounce of stimulation from me. She grunted and shook, then shuddered and I felt the muscles of her vagina spasm involuntarily over my fully inserted tongue as she ‘came’.
She remained squatting heavily on me struggling for air and struggling to stand up. She clearly found squatting painful, particularly for prolonged lengths of time. She stumbled and stepped over me and Miss Wiff-Naseford congratulated her on her performance. Cheryl gave her a sneer as a parting gesture for the inappropriate remarks regarding her weight.
The headmistress stood up and slid off her long directoire nylon knickers, in a very unlady like manner. She crawled over to me and wiped my face with them, evidently realising that sexual secretions and pubic hair were blocking my nostrils by the way I snorted escort diyarbak─▒r wildly to clear my air passages.
I told her that I couldn’t take much more of this punishment and asked her if we could try a different position. She seemed responsive to my suggestion and agreed to give it a go.
“Mr Tom here requires untying, I need four girls to give me a hand,” she said to the bored looking nineteen year olds standing in a huddle.
They untied me and I stood up and stretched every muscle in my body. I felt weary and worn out. and had only pleasured two girls. They pulled up a long leather settee and I knelt in front of it with my hands behind my back. One girl tied my wrists together and another one strapped by knees together so that I could not get up, only fall sideways. Yet another girl strapped my wrists to my ankles with a long loose leather belt, so that I was able to kneel forward and kneel on my heels.
Miss Wiff-Naseford confirmed that my ‘fettered frame’ followed the ‘spirit’ of the 1889 punishment if not to the letter. We both agreed that it would be more comfortable for the girls as they would not be forced to squat.
I knelt there naked on a cushion, to protect my knees, staring at the empty sofa in front of me. I hoped that this new position was going to work.
* The New Position
“Glenda Ash please step forward and remove your underpants,” said Miss Wiff- Naseford having pulled her chair up to the edge of the settee. I was aware of a tall girl smelling strongly of scent walking across the room and standing next to me. I watched her out of the corner of my eye and saw her take off a pair of silky lacy pure white knickers. She pulled them over my face and everyone laughed, except me.
She adjusted them so my nose was pulled into the crotch. As soon as I breathed in the intoxicating smell I felt amazingly aroused and my penis stiffened into a near horizontal position. When the giggling had died down she looked towards Miss Wiff-Naseford for further instructions.
“Stand in front of him and say ‘Head up skirt Tom’ and he’ll know what to do. Won’t you Tom,” she said, now too far away to aim a kick.
Miss Ash stepped around me and removed her knickers from my now upturned face and threw them to one side. I knelt back on my heels and leant forward. She shuffled up to me and parted her legs so that my head nestled against her skirt covered thighs.
“Head up skirt Tom,” she said smirking, I peered into her big blue eyes and ducked slowly under her skirt and petticoat.
She lifted both garments over me and shook them down around me so that I was covered from the shoulders up. The coolness of her nylon slip contrasted with the heavy scratchiness of her woollen tartan skirt hem. I allowed her to move further forward until I was able to tilt my head back and feel her hairy vagina on my mouth.
I felt relatively comfortable except that my balls were a little short of space. I held this position until I thought she was ready then began licking her as firmly and rhythmically as fast as I could. She shivered when I touched her clitoris and I felt her body loosen then tighten then loosen again. She was clearly very sensitive to me being under her skirt. My naked shoulders rubbed against the slippery smoothness of her black nylon stockings and the ruched elasticated lace of her white suspenders. Beneath me I was able to glance at her black high heeled shoes which she’d positioned on each side of my knees.
I felt her hands hold my head through her skirt as she manoeuvred my face into are more pleasurable position. I drove my tongue into her and licked her solidly for many, many minutes, flicking at her clitoris at the top of every lick.
All of a sudden she appeared to be at the point of no return and made a ‘dash along the home straight’, as it were.
I merely made sure my nose was held in a fixed position as she jerked herself off on me to the screams of ” Yes, yes, yes, oooh yes.” Quickly she jerked herself again, then again then one last time. She achieved her orgasm and drooled her spendings over me, so much so that it dripped over my chin. My face stank of vagina.
She pulled up her uniform and I leant back on my heels as she stepped away. After retrieving her knickers she returned to the line. I turned and saw the headmistress beaming with pride. It had been so quick and effortless. Glenda had done most of the work. The smooth contours of my face were enough to stimulate her to orgasm, but I still remained frustrated, which unfortunately was the main ethos of the punishment.
Barbara Bunning was a very slim, extremely tall elegant girl. She had shoulder length chestnut brown hair tied back with an Alice band. She walked up to me and shuffled forward and pushed her stomach into my face. Her school skirt pleats were coarse fibred and rough textured.
She lifted first her skirt, then her wide flounced petticoat, and draped them over my head. I watched entranced as she reached up inside them and slid her panties down to her knees. The pungent musky smell hit me as I stared at the stains in her crotch. She moved further forward over me so that my head was pushed firmly between her thighs facing downwards. She held me there. I could feel her pubic hair on the nape of my neck. My penis felt as if it was ten times it’s usual length.
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