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A Visit to the Headmistress

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I was 25 and randy, but I was also curious. Well, they say curiosity killed the cat, but in my case curiosity got me the cat. I’d better explain.

It was about five years ago and I was just coming off a torrid affair with a lovely colleague, who had dumped me for a much older man, the bastard! The older man, not the lovely colleague.

Sandra said that while my eight inches of uncut cock was very nice, she needed more maturity. Pity, because at 30 she was the type of woman I’ve always fancied – a mature, big-busted blonde. I go, you see, for older women – not that much older, but at least five years, preferably 10.

I’d picked up one of those glossy magazines that feature ladies in lovely lingerie, mainly for the pictures but also for the words – the words in the massive section of adult advertisements in the back section.

One really caught my eye. It was of a pretty blonde wearing glasses, and a black latex outfit, which showed she had a full, fabulous figure. It proclaimed: “Visit the headmistress. She’ll correct all your mistakes, you naughty boy, you!” And there was one of those mobile phone numbers.

Well, I was flush, as they say at poker games. I’d had a big win on the football pools – closer to 40,000 pounds than 35,000 – and I was in one of those “money’s no object” moods.

I put the magazine down on my bedside table and stopped whacking off and used my mobile to dial the headmistress’s number. It rang only two or three times, then a deep, husky and extremely sexy voice answered.

“Hello, this is the headmistress – more mistress than head. Leave a number, I’ll call you back. Honest, you can trust me, I’m a dominatrix!”

And since I always do as I’m told, I left my mobile number, thinking at the time “That’s the last I’ll hear of the headmistress”, and opened the magazine up to resume wanking at pictures of a mature, 40-year-old pornstar.

Ten minutes later, as I was nearing the big O with Mrs 40-Year-Old, my mobile rang. “Hi, this is Lee.”

And then the headmistress’s sexy voice replied! “Hi Lee, this is the headmistress returning your call. How can I help you?”

I thought you can offer to sit on my face, that’s how, but then thought better of it and asked: “I’ve seen your advert, you look lovely and I’d like to know about your services and charges.”

There was a pause, and then the headmistress spoke again, only somewhat warily. “You sound nice Lee, but you also sound young. I don’t do young.”

“I’m 25,” I called out, afraid she was going to hang up.

“OK, you scrape into the age parameters,” she said. “Well, I’m a dominatrix, I don’t fuck. You can perform body worship, I may give you a golden shower if I like you. And it’s a headmistress scenario. You’re the schoolboy, you attend class naked and I give you a test.

“Fail the test – and you will fail, promise me, you will fail – and I punish you.”

I was hooked. Then she spoke again: “The charge is 200 pounds for an hour and a half, 300 pounds if I use the head girl as part of the scenario. Oh, and from her you will get head.”

I was doubly hooked. “How old is she – and how old are you, headmistress?” I asked, adding quickly: “You see I’m into older women.”

There was a chuckle. “Most naughty boys are,” she replied. “I’m 40 and my head girl is 35. You’ll like her, great body, huge tease.”

The upshot was that at 10am the following morning – it was a Saturday – I was standing on the doorstep of a rather fancy address not far from Berkeley Square, in Mayfair, with an envelope containing 300 quid.

The door opened slightly and I sneaked in through the small gap to be confronted with a hard-faced woman in her mid-30s. She had long red hair, and sported two ponytails, one of each side, which was obviously an attempt to make her look a lot younger. The smock she was wearing, though, could not hide the fact that she was stacked!

“You must be Lee, the naughty pupil here for his lesson,” she smiled, holding out a strong hand, then pocketing the envelope containing the fee. “I’m Raewyn. Follow me and we’ll get you ready for the headmistress.”

She took me to a small changing room and ordered me to strip. As I did, Raewyn removed the smock to reveal an outfit which would soon have me harder than a length of lead piping.

Her breasts – lovely, lush 36-inch jobs, I later found – were pushed up into mouth-watering uplift in a black satin half cup bra, which did not cover her nipples. Jutting just above the cup line, they were erect.

On her hips was a matching black satin garter belt, which held up shiny black stockings. Her pussy hair was confined to a heart-shaped thatch of redness over her mons. Her shoes were so high heeled it was a wonder she could walk!

When I was nude and stiff-pricked before her, she opened a door on the inside of the changing room and admitted me to the “classroom”. In the middle was a desk and chair, all in one, just as in a school. In front of it stood a blackboard. On it the numbers 1 to 10 had been written in chalk.

“Sit istanbul escort at the desk,” Raewyn told me, and I obeyed. Then, before I had hardly settled into the seat, she snapped: “Stand up for the headmistress!”

A side door opened and as I stood to attention, prick swaying before me, the bespectacled headmistress entered. She was a superb sight. Blonde hair pulled back into a severe pony tail, she wore glasses and I can tell you Dorothy Parker got it wrong. Men do make passes at girls who wear glasses. At least, girls, or women, I should say, like the headmistress.

She was wearing a black see-through shirt, and her glorious breasts were revealed in it, with big nipples pressing against the material. Her lush hips and glorious bum were covered by a gleaming black leather miniskirt. She carried a cane, wore high heels, but no stockings.

“Good morning, Lee,” she announced, standing by the blackboard.

“Good morning, headmistress,” I chanted, in schoolboy sing song.

“Nice erection,” she smiled, waving the tip of her cane at me. Then, she snapped into business: “Be seated!

“Right, you’ve got 10 questions to answer, Lee. The questions are each worth 10 strokes. Get them all right and you won’t receive a stroke, it’ll just be body worship and teasing from the head girl, Raewyn, here.

“For every incorrect answer it’s 10 strokes. Understood?”

I nodded and she smiled.

“Good, then we’ll begin. What is ‘gooch’ a slang term for? Raewyn, give him a hint.”

And with that the hard-faced redhead stood in front of my desk, turned her back on me and bent over, feet wide apart, clasping her ankles.

Her hairless quim peeped back at me. Gooch? I’d never heard of it. “Er, I don’t know, headmistress,” I muttered.

“It’s the area between the cunt and the anus, you ignorant little boy, you,” she informed me. She could have told me it was the slang term for the Horn of Africa and I’d have accepted it.

The headmistress turned, giving me a magnificent view of her great arse as she circled the number “1”.

“What is macrophallia?” she asked, glaring at me once more.

“Erm, fucking corpses?” I guessed, which drew a snigger from Raewyn.

The headmistress circled the number “2”. “It’s the condition of having a large penis,” she told me, “and judging by that piece of meat you seem so proud of, I’m surprised you didn’t know.”

The next question was what does the acronym DATY stand for. I didn’t even know what an acronym was, let alone that it was short for “Dining at the Y”. The third number on the board was circled.

“Who did Linda Susan Boreman become famous as?” snapped the headmistress. By now my head was reeling, and I should have guessed, of course. “Linda Lovelace,” said the lovely “school” head after I had guessed Pamela Anderson. The figure “4” was circled.

And so it went, until I was gulping and contemplating the 10th question. Already nine figures on the blackboard had been ringed.

The headmistress eyed me sternly: “And get this wrong and I’m adding 20 strokes for you being the thickest, dumbest, most stupid student all week.” I swallowed at the thought of 120 strokes!

“Who is the president of Ethiopia?” she grinned.

“I haven’t the faintest idea, headmistress,” I answered, completely truthfully.

“Neither have I,” she beamed, “but it’s going to cost you 120 strokes!”

“Raewyn, get him into the frame,” the headmistress snapped, “while I get ready.”

“Yes, madam,” said the hard-faced redhead, who then took me by the hand and led me into another room adjoining the classroom. This room was definitely nothing like anything I had come across at my grammar school!

The focal point of the room was a sturdy steel triangle, bolted to the floor and hanging from a length of chain suspended from the ceiling. Straps were at the top where the two side beams joined. Raewyn stood on a chair and with her quim delightfully close to my face, hooked my wrists into the upper straps.

Then she strapped my ankles to the bottoms of the beams, a move which drew my thighs apart and left me totally vulnerable. A broad strip of leather hung across the beams half-way up them and Raewyn pulled my cock and balls through the aperture in its centre, before lacing cords around the aperture tightly around my shaft and scrotal sac, thus enhancing my erection.

She then pulled up a large leather stool and sat in front of me, her face inches from my jutting hard-on. She had no sooner settled than the door opened and in walked the headmistress, carrying two implements, although I hardly noticed them.

She was now naked, save for gleaming black leather boots which came to half-way up her lovely thighs. Her pussy was shaved, her piss flaps peeping out in their pinkness. She had removed the glasses.

Stepping behind me, the headmistress put her face up to my cheek and began to tell me what was in store for me.

“Now, my darling Lee,” she said, her voice a whisper against my cheek, “I’m going escort bayan to give you 10 strokes across your shoulder blades with this cat o’ nine tails.”

And with that she traced the flogging device’s nine lashes across my bare back.

“After each stroke Raewyn here is going to suck your cock – just once, but you’ll enjoy it. You will then make a decision as to whether you want the next 10 strokes on your back again, in which case you will receive 10 more sucks, or whether you want to colander tawse across your buttocks.”

With that, the headmistress waved a wicked looked black leather tawse, with five circular holes drilled in it.

“After each stroke of this lovely little flogger, you will not get a stroke from Raewyn, but you will get the pencil. Show him, my dear!”

Raewyn held up to my face a long pencil, with a rubber eraser on the tip. “Like the sucks, you will get 10 strokes of the pencil, eraser onto your balls – quite painful, I’m told,” the headmistress informed me.

“Right, that’s quite enough preliminary chatter, let’s get started, shall we?”

I braced myself as I heard the headmistress pace herself off to a position behind and off to my left. She raised the cat o’ nine tails and it went “Whooosh” through the air before cracking with a resounding “Thwaaack” across my shoulder blades. I arched and bucked and heaved in my bonds, but I could not, of course pull free.

The burning sensation of the cat was starting to make itself felt across my defenceless flesh when I felt the ineffable sweetness of Raewyn’s mouth sucking on my cock, deep, deeper, until she was almost at my pubic bone. Then she pulled off, very slowly until, with a little “plop” she released my cock.

“Whooosh” came the cat, “thwaaack” went the sound, onto my cock again came Raewyn’s mouth. The burning increased, then again came “whooosh”, then “thwaaack”, then the delightful fellatio.

At last the headmistress had burned 10 strokes onto my poor back, and then she was by my side, her moist pussy rubbing gently against my upper left thigh.

“Decision time, darling,” she whispered, graunching slowly on my thigh. “Cat and cock suck, or tawse and testicle torture? Pain and pleasure, or pain and pain? Your decision, Lee, take your time, I know it’s not easy.”

Much as I hated the cat, I feared the double dose of tawse and pencil eraser. I made my decision: “Cat, please, headmistress.”

The woman laughed. “No, silly, I’m not the headmistress now,” she said, “in here I’m the mistress.”

And again she stood away from me, this time off to the right, and wielding the cat in her left hand, swept 10 more agonising strokes up against my now screamingly-hot shoulder blades, the fresh angle of attack laying a fresh series of strips across my back.

Each stroke was followed by a delightful mouth suck from Raewyn, but each stroke seemed to be cutting my back in half as the mistress laid it on.

Again she was pressing up against me, her lush full breasts rubbing against my writhing torso, her minge melting on my right thigh this time, as she sought my next decision.

“What’s it to be, sweetie?” she asked, in a kindly, friendly tone. “More of Miss Cat or some of the tawse?”

I knew I couldn’t take another 10 strokes from the nine-tailed flogger – at least, not right now – so I opted for the other implement of torment: “The tawse, please, mistress.”

Off to my left, colander tawse in her right hand, the dominatrix rained down a blow which cut across both buttocks with a searing stroke.

Then I tensed, fearing Raewyn’s assault with the rubber-tipped pencil. But she did not apply it immediately, letting me feel the pain of the tawse sink into me.

But suddenly I arched in my bonds, as the pencil was flicked upwards onto my left testicle, sending a sharply intense shock like a surge of electricity through me. I writhed, then calmed and when I had, the mistress delivered stroke number two with the tawse.

Again Raewyn put me through an agonising period of waiting before punishing my right testicle.

By the time I had received the final blow in the 10-stroke batch, I was sobbing and moaning. The mistress did nothing to alleviate my misery. “There, there, Lee,” she cooed, “you’re doing so well. Only 90 more strokes to go!”

Ninety! I could hardly contemplate nine, let alone 90!

“What’s it to be, Lee, tawse and testicles, or cat and cock?” she asked.

My balls were pounding parcels of pain and I had to have relief, but even so I could hardly believe my ears as I heard myself pleading: “The cat, please mistress!”

Again I suffered 10 excruciating blows from the leather cat, but at least they were interspersed with the sweet sucking of Raewyn, and by the final blow, she had almost succeeded in getting my cock back to semi-stiffness!

The final suck on my cock had hardly stopped, when I again pleaded with my flagellant: “More of the cat, please mistress.”

After the next batch of 10, my mistress informed me: “You’ve Kartal escort had 50 strokes, my dear. Ten more and we’ll find two more targets. That will ease your discomfort, won’t it?”

I seriously doubted that it would, but I mumbled “Yes, mistress” and then heard her ask: “Where’s it to be, Lee?”

“My backside, please, mistress,” I gasped and steeled myself for the next 10, which drew shrieks and wails from me as the tawse smashed against my buttocks, and the pencil against my poor, helpless balls.

The mistress then placed the cat and the tawse on a table behind my battle-scarred back and returned waving a much smaller implement in my face.

“Penis tawse, Lee,” she smiled, rubbing her breasts against my chest, and cupping my assailed testes in one hand. “You’ll like this. First, Raewyn here will get you erect, then I’ll give you 25 strokes on the cock.

“After that, Raewyn will give you 25 strokes with her mouth. There, that’ll be nice, won’t it?”

I could only think of the 25 strokes to be inflicted on my cock, but I nodded: “Yes, mistress, thank you, mistress.”

“OK, darling, get him erect,” said the mistress, and Raewyn bent to her task. Sadly for me, the job did not take too long – a minute, two minutes at most and my poor prick was erect and ready for his punishment!

The mistress stood off to my right, placed her by-now drenched pussy onto my upper right thigh and flicked the cock flogger down onto my shaft. Then again, then again, until she was beating a rapid-fire tattoo on my prick. “He’s all yours, Raewyn,” she said, after raining the 25th and final stroke across my shaft.

Raewyn’s experienced mouth worked away on me, long stroke down, long stroke up, a kiss on the helmet, then a repeat of the process.

I was rigid and erect when she had finished and the mistress stepped in front of me, smiling. “Twenty-five more, darling?” she inquired.

“Yes, please, mistress,” I said.

“Oh, sorry, but I forgot to tell you that the second batch of 25 is followed by the pencil. Sorry ’bout that!”

“No,” I nearly shrieked, my body shaking and quivering, “I thought she’d suck me again. Oh please, not the pencil!”

“Sorry, Lee,” smiled my tormentress, “but you’ve made your bed and now you’ve got to lie in it. You requested the penis tawse, and the second batch with the penis tawse is always accompanied with the pencil.”

And then she smilingly delivered another 25 strokes to my cock, which by the final blow, was again completely limp. The mistress then took feeble little prick in her hand and pressed it against my heaving abdomen.

“I’ll keep this pathetic little creature away so you can concentrate on your work, darling,” she informed Raewyn.

Then I went through an agony of waiting as the “head girl” obviously waited for the pain in my prick to subside. When she was finally satisfied that I had recovered, she began to provide me with an entirely different type of pain to endure.

The pencil flicked mercilessly against my hanging ball bag, once twice, three times, then four, five. After the fifth stroke, Raewyn paused for several minutes as I hung, helpless and sobbing before her and her mistress.

Then she resumed – five more strokes, a period for recovery, five more and so on until I had received my full entitlement.

“Now, darling,” said the mistress, letting my little limp prick fall back onto my burning, battered balls. “the final 10 – across those lovely pectorals, eh?”

I, of course, had a question. “Followed by what after each stroke, mistress?”

She grinned. “A sucking stroke from Raewyn, you awfully suspicious little schoolboy, you,” she smiled.

For the final 10 strokes, mistress pulled the leather stool off to one side, and stood on it to inflict the blows. Raewyn stood off to the other side and bent to suck on my cock after each stroke.

At last the pair released me from my bondage and I collapsed onto my knees, body a mass of agonised stripes and burning ball pain.

As I sucked in big breaths and tried to forget my pain, I noticed the pair arranging a large rubber sheet on the floor. When they had done this, my mistress stepped onto the mat, giving me a fine view of her incredible sexy arse, then turned to face me, minge exposed to my gaze.

“Come on Lee,” she said, “time to thank me.”

I crawled towards her, I honestly don’t think walking would have been possible at this stage, and knelt before her fair-haired pussy, her piss flaps pink and moist.

“Lick me, darling,” she whispered, placing an incredibly gentle hand on my neck and pulling me towards her quim.

I tasted a moist and tangy twat, which had a strong but not unpleasant feminine odour. For some minutes I kissed and sucked her pussy until, absolutely without any warning, I felt a strong jet of urine blasting against my face.

The release of her piss was followed by a hissed warning: “Don’t you dare pull away from me, Lee, don’t dare!” And I felt instinctively that my task was either to continue to lick at her pussy or to lap at her salty stream. I chose the latter, then – when the flow had ceased – licked her until she pushed me away.

“He’s all yours, Raewyn,” she informed her “head girl”, “and I may be wrong, but I suspect he likes it.”

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