Naughty secretary stories

Naughty Secretary Stories

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Naughty secretary stories

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His view would be excellent if he had bothered to stay. I leaned back as I began to slowly finger my clit. It was so relaxing to think about Jack doing this, so perfect.

I jerked forward closing my legs and removing my hands from between them in one quick moment. Jack was standing in front of me.

He was smirking. He reached forward and caressed my throat with one hand, I stood frozen in my seat. His seat. He held my face in his hands, silently thinking for a long minute.

He continued to rub my neck with one of his hands while the other traveled to my crotch where he felt how wet I was. That snapped me out of my stupor and I grabbed his hips and pulled him closer.

He smirked again as I unbuckled his pants and found a full on erection waiting for me. I took all of his cock into my mouth and felt the familiar adjustment my throat made to accept it.

I used to think this would make me gag, but practice told me it actually supplied more liquid from the back of my throat, making the whole process easier, and more pleasurable for him.

The hand that suddenly tightened around my hair confirmed this. He grabbed my breasts roughly, bending me forward over the desk. My only thought was, Yessss.

He lifted the small amount of material covering my butt and entered me from behind. His cock was perfect. He thrust into me roughly, but rhythmically.

With that, he gave my ass a hard smack. I screamed in surprise and he chuckled. This was even hotter than I imagined. He began thrusting harder, using one hand to position my hips and the other the massage my breast, occasionally pinching the nipple.

I told him I was about to cum and he moved his hand down to my pussy to finger my clit and guide me along.

I felt his muscles tense up at the same time as mine. Sign up for the Thought Catalog Weekly and get the best stories from the week to your inbox every Friday.

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Remember to visit a dermatologist once you've completed the quiz, and talk to them about your answers. The threat of extra strokes made him comply.

After the full eight strokes had been given, he lay sobbing over my desk, begging for forgiveness.

He was a very sorry boy. Which was what he should be. Pulling up his shorts obviously was uncomfortable for him, and I could see he would have loved to rub his burning backside right now.

But, of course, that was not to be. Instead, he had to stand facing the wall, his hands not on his bottom but folded on his back.

So this it was. Half of the culprits had been dealt with. Old Fliegner caught Jenny with her skirt too short! Patricia Miller was eager to spread the news.

From what I hear, Caro Fletcher from 12A just got a whacking for that last friday. Like Jenny got.

But, of course, Jennys punishment had been a much-discussed topic during the last days. The punishments given by the headmistress were always of special interest for all the pupils at Wilhelmsen Institute.

And especially so when someone from ones own year got it. Miss von Platen-Wilhelms had earned a reputation as a stern disciplinarian.

Suki Watanabe was just passing by. But yes, I saw her shortening her skirt up this morning. Everyone knows that!

Katrin stopped that discussion short. It was a question to which the girls found many answers. Patricia insisted that it would be a severe caning, while Katrin thought that Jenny might just be expelled and sent home.

Anne suggested it might be both, while Suki silently wondered if her lucky streak would continue. She was no angel, but had avoided being caught so far.

The chattering went on for a few minutes, when suddenly Kristina Larsson called from inside the study room:.

Anyway, the one girl who was the most curious was with no doubt Jenny Woods. In less than 24 hours, she would have to walk over the headmistresses doorstep, for the second time in 7 days.

And what would happen there, no one knew for sure…. Sitting at my desk, sipping my tea in silence, I went over the list of pupils that still were outside.

One pupil from year Two pupils from year And two seniors from year Even if she did not know it yet this earned those two the honour of being put to the end of the line.

Wilhelmsen International Institute had a strict non-smoking policy, the girls were in for exemplary and severe punishment. Putting my cup away, I pressed the button on the intercom.

Oh, and remember that Woods and Fletcher will be last, and come in together. This made Lisa Müller next, a 16 year old girl who had been sent here for tardiness and missing homework.

She had been in my office before and certainly knew what to expect. She walked in slowly, her head lowered. Her uniform looked neat.

What do you have to say for yourself? She did so. I could see the hand was reddened and a little swollen. Lift up your skirt and bend over the desk.

I am going to give you 8 strokes with the cane. I watched her as she obediently grabbed her skirt and pulled it up above her waist.

She then laid her chest over my desk and grabbed the far side with her hands. I picked up the junior cane and moved into position.

Lisa Müller tried to take her beating with dignity. She stoically refused to make any sound after the first 4 strokes, which I placed over her knicker-clad bottom in one-centimetre intervals.

Number 5 made her gasp sharply as it hit one more centimetre lower, almost there where bottom meets thigh. She knew from experience how I caned, where the next strokes would land.

Tears came with those next two strokes, which made neat double-impacts on her thighs. The last stroke had her digging her fingers in my desk, to prevent herself from jumping up and earning extra.

It was made to be remembered though, as it crossed her bottom diagonally, intersecting with the rest of my handywork. Michelle Smith came from the same class as Lisa Müller.

It was her first visit here, but she had been punished in class on several occaissions. I hope your uniform is correct today! I stood up and walked around her, watching her closely.

However, wearing correct and full uniform is a very important part of school life, so I cannot let you off too easily.

And then, of course, there is the second point on your report. Fliegner about it? I know you probably are sorry, but you will be a lot more sorry when I am done with you.

Wearing non-regulation items is a offence that alone merits punishment, but arguing with a teacher when ordered to change into correct uniform is something I take very seriously.

Fliegner and those two extra strokes you earned just a moment ago. At first, she tried to take her caning bravely.

But after the second stroke she began sobbing. Then, her legs started coming up after each stroke. I told her to stop fidgeting, but after the 6th stroke, she jumped up and rubbed her bottom.

Or you will get another two extra, and I will have you held down for the rest of your punishment! Is that clear? She fought with herself for a moment and then bent back over.

She was a well-chastened girl when she was finally told to stand up. Tears were running across her cheeks as she carefully straightened her skirt.

Her blonde hair was in disarray, and I could hear her sob as she put her nose to the wall like the other pupils. Next came Peter Williams from 12A.

It is a rare occaission that seniors have to report for corporal punishment, but it did happen from time to time.

His infractions were those the most common for pupils his age: Misconduct and Insolence. Translated, that meant acting up in class to impress his classmates and backtalk.

Normally, those offences were dealt with best by the class teachers. Having to hold out your hand for the ruler in front of those you tried to impress often did a fine job.

This case was different, for Peter Williams was a repeat offender. And his last prank had involved him showing of his naked behind out of a classroom window.

As a senior, he wore long trousers along his shirt and blazer. The uniform, at least, was immaculate, the school tie almost bound to perfection.

In a way, he looked more like a young man, not like a schoolboy. But he was a schoolboy, and he would find out what that meant soon enough.

And, befitting your crime, i think it is appropriate to cane you not on your underpants, but on that bare part of your anatomy which you felt you had to show at the window.

So, step out of your trousers and bend over. You should know how it i s done from your visits back when you were a junior. It always looked a little strange if a boy as old as Peter Williams prepared for punishment.

Physically, he really was more man than boy. However, bent over my desk in underpants and argyle socks, he did not anymore look very manly.

I slid my fingers into the waistband of his briefs and pulled them down to his thighs. Bare bottom punishments were allowed by school regulations, of course, but I seldom used them.

I felt that a pair of knickers or underpants did not offer much protection from a cane or slipper, but it allowed the pupil to keep a certain modesty.

In case of Williams, I decided for a bare bottom caning just because he had already lost that modesty when he showed his behind to the world.

I took the senior cane out of the cupboard and whipped it throught the air. Despite its size and thickness, it was still flexible like hell. And it stung like that, too.

Peter Williams could be sure to enjoy his cane-marks for the next weeks. And he tried to take them like a man. I had promised him eight of the best, I delivered them.

Full swing, with that little flick of the wrist right before impact. After the eight stroke, he was clearly in grave discomfort, you could hear he was only barely holding back tears.

I want you to serve as an example for the others. Learn from what you see! The 6 pupils took a good look at what was now a very well-caned bottom.

And it felt even more painful than it looked. I watched him getting his trousers on again. Surely he would try to tell his friends how bravely he took his beating.

But he would have to admit then that he had to show his arse in a very undignified manner to 6 pupils from the lower years…. It was time to attend to the last two offenders today.

The two girls who were caught smoking. I placed the senior cane on my desk, right beside the junior cane. The two girls entered my office. Jenny Woods was 15, Caroline Fletcher was She was from the same class that Peter Williams came from.

The two girls stood before me in their school uniforms. Jennys looked neat. So did Carolines, for one grave exception. The normal school skirt for senior girls was longer, reaching down well below the knees.

They were allowed to opt for the shorter skirts the juniors wore, which reached the ground when they kneeled. The one Caroline wore looked shorter, which was easily to bee seen as she stood beside Jenny Woods, whose skirt was regulation length.

You both know why you are here. Let me tell you I am disgusted! Smoking is one of the worst habits there is, and neither the school rules nor I myself have any tolerance for it.

They both flushed a little. Jenny Woods eyes went wide as she saw the two canes resting on my desk. Jenny Woods had once been slippered by me when she was in year 6.

Now, however, she realized she was in for a more severe punishment. But there was that other matter to attend first. Both uniforms looked well.

Jenny Woods had one of her argyles pulled up a little lower than the other. I told her so and she bend to correct it.

Fletcher had the uppermost button of her blouse loosened. She also quickly corrected that. Then I came to the point of my interest.

As they complied, I could easily see that Caroline Fletchers Skirt was non-regulation. Colour and general style matched, but it ended a few centimetres above the floor.

Jenny Woods skirt touched the ground as it should be. Was she lying in my face, despite the fact that clearly her skirt was too short.

Or had she… Even if Fletcher might not believe, her headmistress was a schoolgirl once, and she knew the tricks. Stand up and bend over!

Woods, you may stand up as well! As Fletcher bend over my desk, I lifted her skirt up. At least, the girl had been smart enough to wear a pair of regulation knickers.

I took my slipper and walked around the girl. I took aim, laying the plimsoll on the girls knicker-clad bottom. And then brought it down for four forceful whacks, two across each cheek.

Each stroke was followed by a very girlish sigh, almost silent after the first, well audible after the last stroke. As she did so, she straightened her skirt and brought it down to regulation lenght.

I had both girls stand in front of my desk while I delivered them a good talking to about the evils of smoking.

Woods looked frightened, while Fletcher still tried to look innocent. It was a technique she had probably perfected over the years. With her pouty lips, blue eyes and long blonde hair she looked angelic, and it had probably helped her out of some situations in which she may have deserved punishment.

I knew form a talk with her mother that her father often was persuaded not to punish his daughter just by those innocent looks she threw at him.

Well, it would not work with me. Lift up your skirt and get over my desk again. Six with the junior cane, and two with the senior.

Lift your skirt and assume the position, there, at the side of your fellow smoker! The two girls were now bent over my desk, side by side.

I gave Jenny Woods her six strokes with the junior cane first. She was crying after the third. Then Fletcher got her thrashing. Her attitude was beaten out of her apparently after the first stroke.

After that, she just held on to the desk and let her tears flow. I was sure after she had taken the fourth stroke that she would not smoke again.

After the full eight strokes, she was crying hard. She took those last four strokes, desperately trying not to get up.

When it was over, she, too, was crying hard. You now do know that smoking is not good for you, be it your lungs or bottoms. Each of you will prepare a shor t essay on the dangers of smoking, describing your punishment.

You will read it to the assembly on monday before classes. Adressing all pupils I continued. Now, please form a queue in front of my desk as you will each get your punishment information card that you will bring back next week, with your parents signatures.

I filled out each card and gave it to the respective pupil. Finally, the days work was almost done. I called in Linde-Louise, for there were still some things to attend to.

A headmistresses work, it sometimes seems, is never done. It was a rainy afternoon. The clock slowly advanced towards half past three, at which time the school bell would ring one last time for the pupils at Wilhelmsen International Boarding School.

But while most of those pupils were already looking forward to a nice and enjoyable weekend, a few had other thoughts on their minds.

Wilhelmsen Institute was one of the few schools that kept on using corporal punishment. Located on an island, just off the north german coast, it housed pupils from countries all around the world whose parents cherished the old-fashioned approach to discipline.

In the classroom, teachers made use of a wooden ruler, applied to the pupils palms, to deal with minor infractions. For more serious things, pupils could be slippered by their form masters — or, for repeated or very serious offences, got sent to the headmistress.

So there I was again, waiting for my secretary, to inform me that all those who had been ordered to report for punishment were waiting.

I had their files on my desk already: there were nine of them this friday. There were the usual cases of repeated tardiness, misconduct and insolence.

More shocking, there were two girls who had been sent to me for smoking. I intended to deliver a very clear and sharp message to them.

Seven of the pupils were from secondary school classes, two were sent up from the primary school attached to the institute.

There were 4 boys and 5 girls, the age range was from 9 to 18 years. I took the punishment book out of my desk and placed it on top of it.

Then I turned to the implements that were traditionally used at my office. The three canes, junior, senior and a straight-ended, short nursery cane, were at their place in a cupboard.

My heavy, rubber-soled plimsoll resided in its desk drawer, from where I took it and placed it on my desk.

The wooden ruler already lay there. The secretary knew I always took the youngest first. So, after a few seconds, there was a feeble knock on my door.

A nine-year old boy entered. Slim in appearance, with blond hair and pale skin, he slowly walked up to my desk. I noticed that his uniform was neat and tidy.

I have. I see from your file that you are generally well-behaved. It is your first time here, but know that I cannot be lenient with you. You have to learn once and for all to respect your teachers.

What did Miss Williams give you? I turned the chair that stood before it around and sat down, reaching for the plimsoll waiting on the desk.

If you struggle or in any other way interfere with your punishment, you will receive extra. I opened the boys trousers and slid them down to his knees.

Then I guided him into position over my knees. And with those words, I started slippering him. I dealt out the strokes slow and methodically, alternating cheeks.

By the fourth one, the boy was already sobbing, but he took his thrashing without interference. Then stand there, facing the wall, hands behind your back.

The crying boy did as he was told, slowly pulling up his trousers and his kneesocks, which had slipped down a little. Then he stood facing the wall, while I completed his entry in the punishment book.

Ten years old, sent for repeated tardiness. As she entered, she already looked terrified. I could see it was not only her first time here, in her four years at the institute, she had never been punished.

Of course, she feared what lay ahead. As I told her she would be punished now she whinced silently. However, she fully understood what i told her about the importance of being on time.

Little Florence complied immediately. Tears were already flowing. A light, but sharp, reminder would be enough for her.

I took her arm while standing at her side and then raised my palm. Six slaps on her legs. Now, stand there, nose to the wall, hand on your back, just right beside Mr.

I let the next one enter the room. Martin Goodwyn was 13, and sent here for incorrect uniform and untidy behavior. As he entered the room, I could see what the reporting teacher meant.

He looked outright untidy. His socks hung around his ankles, his trousers were a little dirty. In fact, your so called uniform would not even be appropriate for the classroom.

I took the junior cane out of the cupboard and held it in my hands. I clearly had the boys attention. Each pupil has to wear full and clean uniform. And you will, too.

When I have dealt with you. Now, step out of your trousers and bend over my desk. Four for your untidyness, and two for your impertinent behavior.

Now, you shall not get up before I say so, and you will in neither way interfere with your punishment — or it will be a lot worse.

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