Special Measures Ch. 01

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Errant female student gets special measures punishment.
7.7k words
4.64
41.6k
28

Part 1 of the 2 part series

Updated 06/09/2023
Created 09/18/2018
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So, it's been some time since I last wrote. The following story kinda breaks a few of my own "rules". Firstly, I usually work hard to avoid some of the big leaps of faith that some of these stories ask the reader to make, and which often erode the believability of the story. Secondly, I do not condone such action in real life as this clearly is unacceptable. But this was written initially for only 1 person to read, in response to a few comments prompted by some very lovely erotic imagery she shared with me recently. Call it my first role play in the teacher/student genre. So, I may have cut a corner or two since in that fantasy bubble she and I share, such considerations are less important. My apologies for those who may feel let down by this. Thanks for reading this and for any comments you choose to leave.

*****

"Come" came the terse response to her tentative knock on the heavy panelled oak door. With a sigh she summoned the courage and pressed the handle, cringing inside as she pushed the door and entered.

"Ah, miss Dean, good of you to join me! Did you get lost on the way?"

She stood transfixed, barely over the threshold of his office and heard the big door swing shut behind her with an ominous clunk, and the sarcasm of his comment stung as she sneaked a glance at the big clock above the old fireplace, suddenly regretting her trepidatious and sloth-like walk to his study after the last bell of the day.

"Lessons finished 15 minutes ago, and you should really know I really don't like to be kept waiting?"

Eventually she managed to mumble a simple "No Sir" response, no longer sure of which question she was answering, and the queasy feeling in the pit of her stomach seemed to suddenly feel a whole lot worse.

"Please step forward and look at me when I'm talking to you!" His comment made her realise she'd been studiously avoiding looking at him, and stepped forward to stand in front of the desk.

But as reticent as she was to look at him, her eyes darted furtively to the far side of the room and the apparatus that her eyes couldn't seem to resist, and beyond that the closed cupboard, the contents of which were legendary but reserved for senior 6th form students of the all-girl school, such as herself.

With a final effort she dragged her eyes away, swallowed and looked up to meet his gaze as he sat at his desk looking over his monitor at the pensive school girl that stood nervously wringing her hands together.

"So here we are again, Ms. Dean. Do you remember what I told you would happen if you were summoned here again?"

She watched him closely, hating the mild reasonable measured tone of his voice, eyes drawn to the tailored shirt, and the waistcoat of his suit, with the hint of a brightly coloured tie peeking out above the neckline, and his dark eyes and the look that seemed to penetrate her very soul and see her darkest secrets.

"Erm, no Sir!"

"Ms Dean, come come, Please do not play coy with me, You are in enough trouble as it is, and your tardiness and selective amnesia are just making it worse! So please try again."

She wrung her hands again, feeling her stomach flip, her face start to blush, and the strange warmth that was starting to make its presence felt towards the base of her spine. She blushed even more and dropped her eyes to look at the leather pad on his desk, and longingly at the glass of water that her suddenly oh so dry mouth desired so much.

With a blink and dry lips, she finally mumbled "You told me I would be punished Sir!" And she felt her stomach churn and her pussy clamp, and the corresponding warmth spreading at both the humiliation of her statement and her fascination and perverse thrill of the very threat. Her eyes were drawn to glance quickly again at the piece of furniture, which filled her with both dread and thrill at the same time.

His chuckle startled her, and she risked a glance at him. "Actually, I think I told you that since you were now senior 6th you would be strapped or caned." The threat hung there between them and she felt her pussy contracted at the words and for a moment she worried her knees would give way completely.

"And I can see you are somewhat fascinated by the punishment stand Ms Dean. You doubtless had that to look forward to based on the comments from my staff, but I regret other more serious events have overtaken us".

She flinched inside and felt her breath catch at his ominous statement and her eyes followed his movements as he shook the mouse and peered at his monitor screen, clicking the mouse button.

After a short delay a printer whirred into life and spat out 2 pages onto the return of his desk and as he stood and reached for the papers, revealing the tailored suit pants that matched the waistcoat, and her eyes drew to his rump and lap, suddenly day dreaming about what it would feel like to be draped over it for her punishment, and the warmth now starting to make its presence felt more noticeably at her sex. She squeezed and clenched to try to make it stop but the unmistakable damp feeling just got worse.

He held out one of the sheets for her, and she nervously stepped forward and took the offered sheet.

"Please sit." He instructed and pointed to the single chair set directly in front of his desk. She quickly stepped around and made to sit, pulling the hem of her skirt downwards awkwardly, watching the dark pools of his eyes following her belated attempt at modesty.

"Miss Dean, the school is growing very concerned over your behaviour. You were once a model student, you are intelligent and bright, but your lower 6th year showed a deterioration in behaviour, and while your grades were satisfactory, your teachers have noted a more recent worsening of your behaviour, and our previous conversation seems to have gone unheeded."

He picked up the sheet in front of him and waved it, and drew her attention and she looked at the copy held tightly in the one hand that was not fidgeting with her skirt hem in a futile effort to make the skirt look longer and slightly more decent.

"This litany of complaints just dates from the last week! Continually late for your first period lessons, using your phone to text or e mail in lessons, and wearing increasingly provocative clothing that fails to meet uniform code even for 6th formers.

But as if that wasn't enough and far more seriously I've just this morning received an e mail complaint from the headmaster of the boys boarding school advising that you were caught "in flagrante Delicto" with one of boys Saturday night. He advises that you were found naked and under the influence of alcohol, kneeling and giving the young man in question a blow job. "

As her eyes scanned the document detailing the instances of complaints from her teachers, she flushed in shame and prayed for the floor to open up and swallow her whole at the mention of her weekend exploits that were never supposed to follow her back to school.

"Your behaviour here at school is bad enough, but to add such inappropriate sexual contact to the list makes this much more serious. You are very fortunate that the young man had turned 18 a few days earlier, otherwise this would be a police matter! What is wrong Hayley? Please tell me what is going on, that you are behaving so badly? What do you have to say for yourself?"

The reproach in his voice stung her as if he'd slapped her, but the hot shameful blush just washed over her, and all she could manage was a hoarse "I'm sorry sir, I don't know!"

"The internal school issues I can deal with, but the boys school incident is way beyond my authority. I think that I see no other option but to call your parents in for a notice of expulsion meeting."

The waves of panic hit her and suddenly the queasy feeling turned to full on nausea, while her vision went white like some bad top of the pops music video effect.

"Expelled? Oh no sir, no no no. You can't do that! Please sir?"

"I see no other way, and I certainly can't explain this to your parents in writing or an e-mail can I? So, I'll print the notice and you can give it to them this evening so they can arrange to come in urgently. And besides which it's not like you have offered any explanation, or mitigating circumstances."

The shortness of breath felt like someone was squeezing her heart. The thought of the shame of this being discussed with her parents, with herself present was suddenly too real. She suddenly felt trapped, unable to confess the curiosity that had driven her behaviour.

Her mind span with the conflictions she felt. The hot flush of the memory of her weekend triste just added to the secret she was harbouring and which was utterly impossible to pronounce, even if it might offer some partial justification. "Please sir I really want to be spanked, and I've been playing up more and more to satisfy my curiosity of what it would be like to be over your knee. Yeah right!" No way was she ever going to admit that.

Instead though "Please sir isn't there any other way?" But the look on his face didn't offer much hope, but still she pushed "Not even if I agree to this being handled within school by you? Please sir?"

She watched his face soften a little, seeing the fleeting doubt, and pursued it further. "I'll accept whatever punishments you decide?" She saw the self-doubt again, and in desperation pursued the slim opportunity it offered, and went on the attack with the biggest cheesy gamble she'd seen in some of those movies she'd been secretly browsing, "I'll do anything sir, Please?"

On the other side of the desk he registered her words and phrase by phrase his resolve melted away.

"I don't know Hayley. This is way beyond the scope of appropriate school punishment. I could get into a lot of trouble. You'll have to sign a letter to that intent, that you are requesting special measures."

She seized the thin line of rope of the life ring he seemed to be throwing her. " Yes Sir, you can do anything you wish sir. I will sign whatever you need? Please?"

"Let me be very clear Hayley! You will present yourself on time for twice weekly punishment here in this room until I am quite satisfied that your errant behaviour has been sufficiently corrected. Furthermore, the level and type of punishments you will receive will be completely of my choosing and beyond the scope of what is appropriate here at school, and if you fail to show or renege on the agreement I will proceed with the expulsion. Do you understand Ms Dean?"

The relief she felt washed over her and she felt her breathing ease considerably, but her tummy flip flopped and the words thrilled her more than a little as she forced herself to pause, anxious she should not appear too eager and replied "Yes of course sir"!

His dark eyes bore down on her and she met his gaze, as if seeing inside her. She squirmed in her seat, blushing at the sudden doubt that he knew her shameful little secrets, he could tell, just by giving her the look. This look. Suddenly all the day dreams, all the hot scenes she'd fantasised, all the images she'd dreamt up were tumbling around like some primordial soup just below the surface, and she broke his gaze in the fear she was transmitting them to him.

But with the moment broken, he shifted his attention back to his computer, clicked the mouse a few times and started typing rapidly. She sat and stewed waiting for what seemed like an age, but the big old clock on the wall told her only a few minutes passed.

Seemingly satisfied with his typing he clicked the mouse, and the printer whirred to life once again, the sheet of paper it produced was met by his outstretched practiced hand as he tilted the executive chair backwards. He scanned the document quickly, nodded, and reached forward to hand it to her. Her outreaches hand trembled a little as she took the offered page, scanning past the school scroll and letter head to read the contents. Her pussy juddered and she struggled to breathe again just for an instant as the words washed over her, and her predicament became clear.

"Sign it, or I can produce the expulsion notice if you prefer Ms Dean. You are here voluntarily as an adult, so it's entirely your decision."

Unbelievably she cursed the folly that had led her to this point, cringing again that her curiosity had hatched up a plan to get her here, and suddenly quite sick at the thought she was going to get exactly what she'd been hoping for, yet it didn't seem quite so desirable as she'd imagined, and her tummy did another churn.

She leant forward and took the pen from the desk tidy in front of her, placed the A4 sheet onto the jotter pad, and signed and dated the letter. Again, the wave of almost nausea crashed inside her as she realised the commitment she'd just made. Her own self-doubt scolded her. "See, you wanted this, and now you're going to get it. Are you happy now"? And with dread she tasted the bitter sweet irony, but way too late.

She watched, transfixed as he took the signed letter, leant back again and fed it into a tray, to see it disappear and get scanned and a copy spat out caught again by his outstretched hand and placed it on the desk in front of her.

"Yours to keep Miss Dean, you can take it with you when we're done. But now I think it's time to make a start on your punishment. So, have you been caned before? "She shook her head. "Strapped" and again the head shook, "well there's a first time for everything!" Her stomach flip flopped again, and her eyes flicked to the apparatus to her left, before he stood and his movement drew her back to him.

Stand up please, and she watched as he came around the desk as she stood, her knees unwilling at first. He moved the chair away from the desk, and quickly sat on it.

"Turn and face me, and bend over my lap! I'm going to start with a long hard spanking".

She stood looking at the same lap she'd been daydreaming of just a few minutes earlier, but the curiosity was gone, and in its place was a surreal almost out of body unreal feeling as she felt herself take a step towards him, and bent until her weight was distributed on his lap and her hands were on the floor. Now her pussy clenched as he shifted her position, felt his hands reach for the hem of her skirt, grasp it and lift it, revealing the skimpy white panties she'd been foolish enough to wear and which barely covered anything.

She felt the coolness of the air on her bar skin, felt his left-hand reach around over her right flank to steady her, and she jumped as the cool touch of his hand measured his aim point. She felt her pussy jump, and the moist heat of her sex again, then closed her eyes, and waited as his hand lifted before it slapped back down onto her bottom, and her cry more of shock than pain escaped her.

The follow-on rhythm of his hand shanking her bottom stung, although not as much as she'd been expecting, and at first, she felt lulled into believing her ordeal might be very easy, but soon she began to realise her predicament as each successive blow followed quickly adding more and more heat, with no time to absorb or deal with the previous blow. Her cries soon grew to accompany each slap, and she felt the heat build steadily as his hand moved at will to fire her entire bottom and tops of her thighs, covered or uncovered.

Without slowing his pace, he began to increase the intensity of each slap, and her cries became more anguished. Soon her legs kicked and her toes frequently left the floor and she bucked and writhed. But the heat in her arse was spreading and coalescing with the heat of her sex, and she felt the wet slip of her labia as she kicked realising she was now quite wet, and trying to keep her legs together in the hope it would hide the fact from him.

But he paused, and rubbed his hand over the heat of her bottom as if to test his handiwork.

With shock she felt his thumbs hook into the waistband elastic of her panties, and produce an involuntary cry "Nooo" as his thumbs started their migration down her legs feeling her panties invert and roll to follow even with her legs jammed together, until the damp crotch of the material started to lift from the glaze of her wet sex, and parted company.

She shuddered as he yanked her panties below her knees, the humiliation of being bared, and the shame of her obvious excitement causing her to clench again. But all too soon his hand started down again on her bare skin, hot, hard and unyielding. Soon she was kicking and writhing, her right-hand whipping around to try to gain some relief from the heat, but he quickly pulled it up into her shoulder blade with his left hand, and responded with harder spanks.

She no longer was in control, her legs scissoring as far as the panties at her knees would allow, and split far enough that all modesty was gone, and felt the first itchy tremors down at the heat of her sex, and recognised the first warning signs. Inside she cringed, screwed her eyes tight and tried to stop the feeling from taking a hold, it would be just too embarrassing to cum bent over his leg as he spanked her, but his blows now seemed to zone in at the base of her tushy at the worst best spot and deny her the escape she prayed for. The tremors grew stronger, the white-hot craving with them, and his pace quickened sending her mind spinning, until the shudders hit and she became a passenger, coming hard and keeping on coming as the spanks continued to land.

No longer caring she shuddered and writhed, hands clenched in balls of desire, unable to stifle the moans as the second wave of orgasms crashed down on her. "N n no no" came the strangled cry as she jerked through her nerves firing uncontrollably.

It took a while until she'd eventually noticed he'd actually stopped spanking, and opened her eyes as he'd released her trapped hand until it flopped to the floor, slowly awareness returned. Her hip could feel something hard grinding into her, radiating heat and when it throbbed as she shifted, the aftershock came and she came again flushed hot with embarrassment as there was no way to hide what had happened, and the realisation of his excitement registering through her scrambled thoughts and racked breathing, slowly recovering her composure.

His right hand lay still spooned to the shape of her scorched naked butt, fingers slightly splayed and she suddenly felt the confliction of the intimacy of his contact, and the comfort of its presence, even after the pain and the pleasure it had dispensed. And then his left hand made itself register, hooked around over the top of her waist and fingers tasting the skin of her left hip.

She just lay there listening to the silence, wondering how he would break the spell, wishing she had the courage to wiggle and grind her hip to feel his heat and hardness again.

"Get up please Hayley" came his croaky instruction, and she felt his hands reach for her panties and pull them back up, pull her skirt down and got a pat on her rump for her trouble, prompting her to comply and wriggle to slide off his lap and stand with shaking legs.

Her eyes risked a quick darting look at the lap she'd just vacated and the bulge of the tailored suit pants, and then up to his eyes and the dark pools that seemed to be quizzically searching her own for something. He stood and the moment was gone, although she sensed an uneasy feeling from him, wondering if he maybe didn't notice what had happened, trying to hang on to that thin veil of denial.

" You will undress down to your panties and bra, fold your clothes neatly and place them on the chair" he said pointing to where he'd just been sitting. "And be quick about it!"

At first it barely registered, and the "it can't be happening" feeling returned. But he perched on the edge of his desk, and crossed his arms, and met her unsure gaze with such an intensely forceful look that her moment of hesitation evaporated although she surprised herself with the presence of mind to worry about what order to undress.