Special Measures Ch. 02

Story Info
Hayley returns for her second visit to her tutor.
7.2k words
4.72
18.8k
15

Part 2 of the 2 part series

Updated 06/09/2023
Created 09/18/2018
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This is a continuation of a previously submitted story of pure fantasy, and I'd suggest best read after the previous chapter/story. Again, my initial comments from that story still apply, but thank you for reading and thanks for the lovely comments of support and encouragement.

*****

The final bell sounded on Tuesday afternoon and jolted her into action. Today she was quicker than usual to pack, and moved as rapidly as she felt she could without giving her history teacher any reason to make any more complaints. Thursday seemed like such a long time ago, but then memories flooded back with an intensity that still shocked her, and yet here she was again heading off to his office as arranged, albeit at a much quicker pace this time.

Last Thursday she'd arrived home late, barely moments before her parents had from their work, relieved to avoid the awkward explanations, made some excuse and hid in her room. She'd stood and looked at the woman staring back in the mirror, rather than the girl that had left that morning and replayed her visit to his study realising a line had been crossed, even though she'd lost her virginity a year earlier in a rather unsatisfying fumble with a then boyfriend. she'd quickly undressed from her school uniform and with the door locked, she'd stood naked and turned to inspect her sore tushy in the full-length mirror.

She'd surprised herself at how the general redness had faded quickly, but she'd run her fingers over the tramlines that his cane had left, and which were raised and red still, and there were a few other marks that she'd presumed were from the tawse he'd used. Even running her panties down had smarted, and she really didn't want to try sitting. But even as she ran her hands over the marks the ache and warmth returned and she knelt leant over her bed and screwed her eyes tight shut, desperate to summon back the hot excitement of her earlier experience. Her fingers sneaked down between her legs and dipped into her aching wet gash and she rode the heady mixture of the recent history along with her own wicked imagination of him slipping his cock inside her to drive her to a crescendo, and even as she shuddered through her first crashing orgasm, stifling her moans, burying her head into her duvet, she reached for her wooden hairbrush and clumsily spanked herself. The nerves firing on her already sore bottom produced a second orgasm that left her breathless and unable to move until the aftershocks finally subsided.

She'd showered as gently as she could, and had somehow dressed and sat gingerly for dinner, & made it through the evening. School the next day had been difficult, with strange looks from her friends partly due to a more appropriate uniform, but also as she'd struggled to sit. But she'd surprised herself at her own fortitude, and at first merely accepted but then later owned her soreness and the marks. To her they were valuable currency and also proof of concept.

Over the next few days whenever she closed her eyes in her private moments, the hot memories broke over her like a wave on the beach, and then her own imagination jumped right on in there with crazy piquant ideas from the depths of some of her most private fantasies and she found herself tumbling around inside the jumbled mix of hot reality and hotter fantasy, and she'd feasted till she'd come shuddering to her self-induced orgasm.

She felt her breath hitch and her face flush as she recalled her parting comment, and then she'd feel the warmth spread and her labia slip and she'd clench her sex up tight to make it worse, thinking again of the punishment apparatus and being bent over it helplessly as the cane scourged her bottom again and again, excited to know she'd take it all and more.

Monday the nerves returned a little, she flushed as she saw him at a distance, and couldn't suppress the tiniest of shudders at the thought of her fast-approaching appointment. And now Tuesday was here, and here she was again on her way to his office once again with the twisted knots in her tummy and the excited warmth seeping through to her sex, not helped by the purposeful stride of the rapid walk, and the bitter sweet anguish that thrilled her so.

Her footsteps on the tiled floor echoed along the approach to his office, and she turned the left corner into the blind return that contained only the door to his office, plus a bench seat, which she realised this time she'd have to use since the red light above the door indicated he was otherwise engaged.

She sighed at the inconvenience of the delay, wondering how long she might have to wait, and sat on the slatted bench with the tumbling of her own tummy causing her to clench her sex and feeling the warmth of her wet labia contract, knowing her panties were quite damp. Closing her eyes, she forced herself to breathe more deeply trying to calm herself, struggling with the contradicting emotions of thrill and dread that seemed to smash themselves together somewhere in her core.

For the thousandth time since she'd somehow found the brazen courage on her last visit to ask him to fuck her, tied to the punishment stand that had both fascinated and scared her, she'd cycled through a strange and uplifting sense of achievement, partially tempered by the fear of what he might do in reprisal, but with the excitement of recalling the astonished and shocked look on his face further exacerbated by the sudden hungry and predatorial look that flashed into his dark eyes. The line had already been crossed and no matter how inappropriate it might seem to others, it felt so right and so good to her, and she was sure that dangerous flash of something dark and primal she'd captured in his eyes for the briefest of moments, telegraphed his desire loud and clear.

But the sickness she felt sat waiting to enter was still difficult, and she realised again that while she thought she had the measure of him, she was still about to voluntarily enter a room that contained a potentially dangerous animal that she could not control, and yet she had this weird feeling of being content.

A click of the lock at the door snapped her back to here and now of the corridor and she watched as the large oak door opened a few inches and a hand reached around to open it fully. She recognised the girl that the open door revealed as a fellow senior student, and for the briefest of moments their eyes met with an embarrassed look before the eye contact broke.

The other girl seemed flushed and more than a little embarrassed to be witnessed leaving his office, and Hayley couldn't help but wonder what she may have gone through, somewhat piqued at the thought that his attention was shared, a small stab of jealousy pricking at her for the briefest moments until the buzzer announced the green light above his door.

She stood, dropped her arms to her side, took a deep breath, willed her tumbling stomach to steady, and forced her feet to move, and lifted her right hand to knock the door, heard his voice call "Come", and twisted the door knob, pushing hard against the solid wood, somehow finding her voice to say "Good afternoon Sir!"

He was perched on the edge of his desk, arms crossed in front of him, a quizzical smile framed his dark eyes but which did nothing to dull her feeling that the wicked flash of his eyes saw everything. On the desk she spotted a small paddle presumably used on the girl she'd just witnessed leaving his office, and again she felt a jealous pang which she hoped he couldn't see.

"Good afternoon Hayley. And how are we today? It's nice of you to be on time, and wearing something more appropriate, although still not quite strictly to the required skirt length I see" but the smile that accompanied the comment seemed to imply approval rather than being critical.

"Please come and stand here" and he pointed to a spot on the floor in front of his desk and just offset to the right of the spot he occupied. nervously she did as instructed, fighting the urge to wring her hands together.

"Please lift your skirt and turn to face me". The complete surprise of the instruction caught her off guard, and she almost couldn't take it in.

"Wha, what sir?" and she quickly regretted it as she saw his eyes flash and the smile fade.

"Come come Hayley, really? Are you really going to waste my time and prevaricate after last week? You wish to cancel our arrangement? The look on his face turned thunderous, all softness vanished in favour of a hard and disappointed searching look.

"N, no sir, please sir," and she dropped her own eyes to see her hands collect the hem of her plaid skirt and lift it to expose herself to him, feeling the hot flush of shame turning her face red. Eventually she found the courage to look up at his face again, relieved to see a more neutral expression, and following his eyes looking down at the damp tell in the crotch of her panties.

"Disobey me again and we are done. I will not waste my valuable time in telling you again Hayley understood?" The gut churn she felt at the hardness in his voice combined with the threat of some unfathomable loss had her nodding, desperate to convey that she understood.

Without moving from his position, he ordered "Come closer girl, legs apart." and his right hand dropped from across his chest as she shuffled forward until she felt his outstretched cupped hand alight on her damp spot. His touch was light, barely any pressure, but still she shuddered and clenched involuntarily at the promise his middle finger offered. He watched her eyes flutter shut and her head tilt back, and felt a subtle shift in her posture on his fingers.

"So, what's this Hayley hmm?" and watched her flinch as his middle finger lifted and tapped the wet gusset of her panties and felt the hot crimson flush creep over her face.

"Sir?"

"Come come Hayley, don't be shy. Your knickers are quite damp don't you think?" And to emphasise the point he dragged the tip of his finger along the wet line, making her shiver and producing a Throaty moan, and after a pause, an almost imperceptible nod.

"And What does this tell us Hayley please?"

"Sir? Us? What?" But the flush of heat that coloured her face betrayed her.

"Well it tells me that you're very different from all the other students who I usually have to deal with. It tells me that even before you arrived to sit and wait outside my office that you were already thoroughly turned on does it not?" And to drive home his point she felt his middle finger bend, and the tip stroke itself along the length of the lips of her pussy with the perfect amount of pressure, and then drag forward to her cocooned clit, pushing into the taught gusset of her panties to provoke a shudder and another soft moan.

But his finger pressure increased wickedly at her sweet spot and she felt it start to splay her and search out her hooded bud in such a way that drove the breath from her, and made her weak at the knees and realise she wanted nothing more than him to splay her lips fully and torment her there.

"What it tells us Hayley, is that you're very excited by the very thought of coming here for your special measures, and it tells us that you are submissive, and thoroughly turned on not only by the thought, but indeed also it would seem by the actuality of BDSM based on last week's little happenstance, don't you think?"

"Erm, I really don't know sir? If you say so?" But even as she spoke his finger probe and swirl to reinforce the point.

And his voice softened as he spoke "Hayley it's ok! You can spend the next years of your life fighting this, or I can help you come to terms with it, but I know I'm right. You just don't understand it yet," and his fingers shifted to slip inside the elastic of her panties and slipped into her wet slit with such ease, swooping back along her crack, teasing her soaked entrance and gathering her moisture to swirl forwards to circle and expose her bud. Round and round it twirled and played, teased and incited, flicked and tormented, and she heard herself moaning as if listening to someone else.

He stepped forward till their bodies touched and she dropped her head onto his chest to focus on the delicious movement of his fingers, feeling the first e familiar crave of approaching orgasm, distant but thundering down the track with huge momentum. She felt him lean forward and whisper wickedly closely with hot breath into her ear. "I'm going to cane you Hayley", and the train leapt instantly much closer, "I'm going to show you what you are, I'm going to hurt you, and make you love it and need it worse than you do right now", and she could feel the tremors in her legs, and her knees almost buckle, "And I'm going to do just as you asked me, and tie you up on the punishment stand and fuck you in such a way you'll love it and hate it and crave it, and make you realise you can't live without it".

His words barely cut through the fog that enveloped her, the smell of his aftershave and his scent, like a drug. The urgency of that need that that one finger provoked was all consuming and demanded more and more attention, and she felt it grow, felt its arrival, soon, sooner, sooner still, just one moment more, and she'd be there.

But as if he was hot wired into her brain his finger was gone, and he stepped away.

She willed herself to hold on to that greedy need to cum, heard herself cry out a despairing "No", clamped and clenched in the forlorn hope she'd tip herself over the edge, but barely able to remain standing. But the train just stopped, knee tremblingly close, but just out of reach.

The overwhelming need ached so frustratingly deep inside and with an intensity that made it difficult to breathe before eventually the fog thinned enough that she looked at him sat with crossed arms watching her perched on the edge of his desk as the flames that licked her libido died back a little.

"lift your skirt Hayley!" The command felt like a slap, and she realised she'd dropped the hem of her skirt. "Quickly now, and come here", and without delay she did as he'd commanded.

" Spread your legs Hayley" and again she complied as His hand rummaged at her crotch and she felt his fingers lift the elastic of her panties and pull down on the elastic and gather the gusset, running back and fore. The tension increased as he rearranged the lie of the elastic pulled, and then released it to snap back wickedly directly onto the centre of her aching wet gash, and provoking her to cry out.

And then the same hand reversed, hooked a thumb into the other elastic, gathered it at and re aligned it, slid forward pulling down. She braced for what she knew was coming, tension steadily increasing, and with shock realised the train was again moving towards her, closer, and closer still.

His hot wicked whisper at her ear, "Five,,,,,,,,four,,,,,,,, three,,,,,,,,,, two,,,,,,,,,,,,,," and the elastic impacted upon her throbbing clit in perfect synchronicity with his breathless whisper "One" and her world went white as the orgasm ripped through her. She shook and shuddered and her knees buckled but his arms wrapped around her and held her tightly to him to prevent her fall. Her breathing was racked and she shuddered and bucked for an age until the tremors finally ceased and the greedy hold on her consciousness released. She nestled into his enveloping embrace and waited to regain control of her breathing, revelling in the feeling of safety his body provided, and breathing in the scent of him and the faint whiff of his aftershave.

After an age, he felt her legs firm up to the point she was supporting her own weight again, and her breathing returned to normal as her breasts pressed on his chest, such that he felt it safe to release her. She took a step back from him and when her pupils finally focussed, she watched his eyes feasting on her as she held her skirt up for him to see how he had splayed her.

After an age she heard him finally speak. "Strip naked please Hayley and be quick about it. It's time for your first 2 lessons."

She watched him step towards that cupboard and even as she hurried to unbutton her blouse, she saw him reach inside and select a cane. She shuddered as he inspected it and ran his hands down its length to check it fit for purpose, but she did not slow or prevaricate, Bra shoes and socks followed quickly in a heap to her side, the zip of her skirt went quickly, until she stood there in only panties that now cleaved her uncomfortably, and looked at him. The cane swished wickedly through the air and se flinched at the power of the sound and movement, while her pussy clenched in strange anticipation. She hooked her thumbs into her panties and paused to meet his eyes, almost a challenge, demanding his full attention as she peeled her soaking panties quickly down her legs.

"Well don't just stand there girl. Get up on the stand! The cane swished again, cleaving the air, and she saw the wicked gleam flare in his eyes as she stepped forward, suddenly regretting her demand of last week and feeling the tumbling inside once again. The punishment stand beckoned again.

This time though as she stepped on to the raised dais, she was familiar with its use and assumed the position, tummy once again resting on the top bar, hands reaching down to the T bar and gripped willingly, hyperaware of the swing of her heavy breasts, and her nipples tightened. She watched him come into direct view, minus the cane, and reach down to feed each wrist in turn into the retaining straps that would immobilise them, and watched his fingers slide the retaining loop downward till there was no escape.

He watched the goose bumps rise on her skin as he laid and then buckled the wide heavy waist strap that held her tightly to the top bar, hearing the creak of the leather as it stretched and settled. She tried to follow him as he stepped behind and walked to the cupboard to rummage and produce something, but she couldn't really see, although she soon found out as he knelt and fastened thick leather cuffs to each ankle before passing the rope that was fastened to them to flush retaining rings recessed in each of the side of the dais.

Finally, the penny dropped, and with a sick tumble in her stomach she felt her legs being pulled gradually wider and wider as he pulled on both ropes until her feet were placed as wide as the stand would allow, and splayed wide for him. She stifled the faintest of whimpers, confused by the sudden fear that her position induced, so at odds with her fantasies that had dreamt up how this might feel, as he quickly arranged some quick knot leaving her completely vulnerable and utterly at his mercy.

"So, Hayley, this is your first lesson. B is for bondage! You feel that sick feeling in the pit of your tummy? You feel how completely helpless and vulnerable you are young lady? But do you feel how your body reacts and betrays you? I can see your hairs rise, I can see the tightening of your nipples, your shallow breathing, and I can feel the heat of your slutty wet sex, and that tells me what I already know. You like this! No, you love it, you want it, and you need it! Go ahead and fight it if that's what you want?" But with a jump she felt his hand reach out and cup her soaking mons, the touch of which released her juices to escape.

She'd not realised exactly when she'd shut her eyes, when she'd receded into herself, but she felt his movement rather than saw it. When he returned, she felt him take up his position and then felt the measured tap of the cane address her bottom.

"Arch your back Hayley please, let me see you offer yourself up to my cane like the submissive I know you to be", and somehow, she found the will to comply.

"Repeat after every stroke. B is for bondage, thank you for teaching me sir!" And with that she felt the first impact, followed a micro second delay later the red-hot searing stripe of pain, heard the cry of a stranger, shuddered and without thinking about the futility, tried to bring her hands to protect and rub her exposed nates. The same stranger's breath hissed from between clenched teeth, but after gathering a breath, and without being prompted she croaked

12