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Chapter 4 by KizzKizz86
What is Rachel wearing?
Nothing...
For just one moment, Jennys world froze. A single moment immortalized on her retina forever. Underneath Rachels skirt was… pearly white silky-smooth skin, and where her thighs met, her glistening bare fanny.
Rachels world also froze, but for another reason. Her heart jumped up in terror. What felt slightly cheeky and arousing on her way to school was now a nightmare. Utterly exposed. She shrieked and grabbed Mr Robertsons invasive hand.
Mr Robertson on the other hand, did not freeze. His face flushed with anger. How can someone be so stupid! He yanked the skirt higher
“Forget something this morning, did we?” he grinned.
Rachel flailed her hands **** to pull the skirt down. In her efforts she pushed the front firmly against the opposing forceful motion, and with that – a snap was head behind her. The clasp gave out in the fight and Mr Robertson was now holding what remained of Rachels skirt in the air, effectively a rag.
Rachel jumped after it. Her pale bottom bouncing. “PLEASE!” Rachel shrieked once more, only dragging more attention to herself.
Mr Robertson grabbed Rachel by the ear to stop her tantrum. Turning to Jenny “Miss Carpenter is it?”. Jennys eyes dragged reluctantly away from Rachels parted ivory curves, voice cracking “yes.. yes Sir!”.
“Come”. Mr Robertson said firmly. Jenny reached for the rag in the corner, “Leave it!”
Rachels horror escalated, she had failed to notice, in the fight, but the entire corridor was packed with loud snickering students and flashing phone cameras. What’s worse was the intense pain in her ear, she struggled to keep up and had no way of keeping her hands over her exposed delicates. She could hear laughter and see the smiles as she approached the headmaster’s office.
Mr Robertson nearly threw the bottomless girl in the door, motioning for Jenny to enter.
“Now! That was a memorable trip down the corridor, wasn’t it?” He supressed a grin. Rachel stood hunched, hands covering her modesty.
“Needless to say you failed the uniform inspection, given our new regulations that means a suitable punishment at my discretion.” Rachel eyes widened.
“Should I leave sir? Jenny uttered.
“No, you stay put, I need a witness. Make yourself useful and open the cupboard in the corner, extract one of the canes hanging on the door”
“SIR!” Rachel blurted out. “Not the cane! You can’t be serious!?”
“Rachel… you exposed yourself to the school, every student in here knows every crevice of your body, front and back, I dare say it’s even been immortalized by the majority of them, you then proceeded to fight me, and now you are talking back. I assure you, I am quite serious, and I advise you to be silent as to not escalate the amount of strokes your bottom is about to receive”.
He was obviously aware that he was the one that had exposed her, ensured that the moment could be immortalized, and took great pleasure in leering at the attractive woman before him. He was hoping his rather “eloquent” tone would deter her from speaking up to the fact.
Rachel stood meekly, both hands now firmly grasping her sex. Clearly showing that he had achieved his goal. Soon the girl would be spreadeagled over his desk, and her remaining modesty will be exposed to him. He felt a bulge growing at the thought.
“Erhmmmm… Sir?” Jenny spoke from the corner of the room. “Which one should I take? You have 7 different ones here…”. “Pick one you like” he said bluntly.
Jenny was stunned, her choice? Suddenly the situation felt more real than ever, Rachel was to be caned, she would be witnessing it. She glanced over her shoulder, eyes resting on those ivory cheeks and how Rachels bottom would react to each implement.
She decided on the one easiest accessible, a four feet quarter inch rattan cane. Her own bottom twitched as she tested its flexibility, thinking about how it would feel getting a well-placed stroke.
“Good choice miss carpenter” Mr Robertson said pleased.
Rachel sobbed silently, shivering by the cool air that brushed over her shapely bottom.
“Now then Rachel, lets get started, shall we? Jenny, come over here and lay the cane down in front of the desk”. Jenny walked silently past Rachel and knelt down in front of the desk.
“Now come here Rachel, spread your legs equal to the length of the cane and lean over the desk”.
Rachel struggled attempting the proper pose, this was absurdly wide, really pushing her flexibility to the limit, she felt her inner thighs burn with the strain. As she leant over the desk she felt the cool oaken surface against her bare skin and the draft now made her acutely aware of just what she was displaying. She gripped the end of the desk firmly, knuckles turning white, tensing up, trying to beat the emotion of utter humiliation.
Mr Robertson nodded approvingly. Bent over, her cheeks spread obscenely wide, he licked his lips at the sight. Her young body stretched her skin firm, her cheeks spread apart and now gave way to all her femininity. Her pink pussy, her backdoor, it was everything he dared hope for. His raging erection was now pulling firmly against the fabric, but he was way past caring to pretend his intentions were pure. He was itching to touch the exposed young woman, to let his hands glide over her.
Jenny was experiencing a similar effect, she bit her lip, a scorching wave of heat pulsated through her body, building from within and irradiating towards her crotch. She felt her breath becoming heavy, and her face flush. Her trance was broken by a soft voice from the desk.
“Please sir… I am so embarrassed…”
“Rightfully so my dear! Miss Carpenter, pick up the cane if you would”, “we will start with a hand-spanking, just to warm you up properly”.
Jenny walked slowly towards the spreadeagled girl, kneeling down her nose nearly grazed Rachels sex. Her mouth went dry, was that a hint of a wetness building there? There was certainly a distinct smell of musk in the air, but it might be her own….
Mr Robertson let his hands glide over the exposed buttocks in front of him, cool to the touch. Now by all means with all his research he could just pound away relentlessly with his hand for 10 minutes and slash 6 strokes of the cane on her bottom, but he wanted to savoir this moment. It was after all, the first girl spread over his desk, hopefully many more were to come.
He raised his hand..
SMACK! SMACK! SMACK!
Rachel gasped for air, determined not to shout, but god darnit that hurt! She tried to adjust her hips, but the position left little wiggle room.
His first few slaps were unnecessary hard, they were to make a statement. He continued rhythmically, alternating cheeks, and slowly decreased the strength of the impacts. Jenny legs were now nearly shaking, she had to constantly fight the urge to let her fingers drift discreetly into her knickers, the heat irradiating from her slit was approaching unbearable levels.
Mr Robertson felt very much the same, methodically alternating target, and every so often, grabbed hold of both of Rachels throbbing red globes and spreading them even wider.
Rachel was now kicking and yelling for it to stop. Her determination and feeling of shame was long gone, now she just wanted to stop the onslaught on what felt to be a bottom on fire.
Jenny could help herself any longer, the point where Mr Robertson spread Rachels crevice and winked at her pushed her over the edge, and her fingers were now deep in her knickers, moving with a mind of their own.
“I dare say that’s a good warmup, now 6 of the best I believe will suffice. You’ve done very well to maintain the position. Pass me the cane please, Miss Carpenter”.
Rachel was sobbing, the desk now moist with sweat and tears. Her bottom was on fire, it felt utterly broken.
“May I please rub my bottom sir?” Rachel stammered.
“Quickly then” Mr Robertson replied bluntly, taking care to hide his erection.
Rachel sprung from her position and began rubbing her bottom frantically, spreading her brightly red bottom as she lifted her cheeks from her inner thighs.
“Get back over girl! Or you will get extras!” Mr Robertson bellowed.
“Pass me the cane, miss Carpenter”
Jenny reluctantly removed her hand from the warm dampness of her knickers. And passed the cane to Mr Robertson.
He took a test swing through the air, a delightful noise cut through the silence.
“Now steady yourself girl. Count the strokes out loud, if you miss one, or leave your position you will get extras. You’ve done very well so Ill make this quick”
Oh god please don’t. Jenny thought to herself, she had been on the verge of an orgasm when Mr Robertson rudely interrupted her wandering fingers, which had now found their way back to her soaked knickers.
The first strike of the cane caressed the already glowing curves of Rachels bottom, who let out a sharp yell, swallowing the profanity that was about to escape her. Leaving behind a clear red line in its aftermath. Her legs were now shaking.
“One sir!!”
Jenny peered between Rachels legs, there was unmistakenly a pearly white dampness beginning to seep out from her crevice.
Mr Robertson had had his fun, he really just wanted the girl out of the room so he could relieve himself the way that Jenny was so blazingly doing in front of him.
He prepared three strokes in short succession, each landing perfectly evenly.
“Two, TRHEEE, FOOOORRR!!!!” Rachel screamed at the top of her lungs. Arching her back and flexing her bottom.
Jenny felt her climax approaching, the sight was just too much to bear.
“Last two, these will sting”
Two quick mild taps in quick succession on Rachels throbbing labia.
“GOD FUCKING!!! DAMMIT!!”
She leaped from the desk, hugging her sex. Seemingly trying to numb the pain. Seeing Rachel rub her pussy was the final drop for Jenny, her legs gave out and she fell on the floor dazed in the most intense orgasm she had ever experienced.
“Count?”
“FIVE, SIX!!! You… absolute..” Rachel swallowed the last words she had in her mind. The last thing she wanted was back over that desk.
Mr Robertson raised his eyebrow.
“I am sorry sir, it caught me by surprise is all” Rachel humbly apologized.
“Very well then. Now as per the regulations I am required to document the ordeal, he reached for the polaroid camera.”
“You’re joking?” Rachel said
“I am afraid its necessary, during the trial period any and all punishment must be recorded to prove no excessive **** has been used.”
My bum feels rather bloody excessive at the moment, Rachel thought to herself as she began to rub it once more. The sensation was strange however, what was earlier stinging pain, now turned to a warm glow, seemingly irradiating from her bottom to her inner thighs.
“Up you get, hands on your side, go on be quick about it, or ill add strikes for your outburst earlier” Rachel rose, resisted the urge to hide her pussy in front of the immortal audience peering through the camera lens.
*SNAP*
“Good, now back over the desk, similar position. And before you start ranting I assure you its only for the trial period, afterwards all documents will be destroyed” Mr Robertson lied.
Rachel begrudgingly leaned back across the desk, exposing her labia once more. This time however, it felt as the warm glow was starting to consume her inner thighs. Blushing as she became aware of the distinct feeling juices running down her leg.
*SNAP*
Mr Robertson admired his treasured photos, Rachel, the bombshell of the school, with a runny nose, makeup smeared down her face, tears in her eyes and a ivory pure clear slit in plain view. The second was even better, 4 evenly distributed sharp red stripes over a bright red bottom. And in the cleft a clearly aroused sex exposed by the camera flash.
“Lovely, you two are now excused” He said with a broad smile
“But sir! I don’t have any clothes!” Rachel protested.
“How right you are! Yet Im afraid I don’t have any spare in here, you could go to miss Graves. I’m sure she has some.”
“But… thats the opposite end of the school! And its mid recess!”
“Right again, yet that is hardly my problem now is it?”
“Sir….” Rachel pleaded and felt tears welling up in her throat
“Maybe Miss carpenter here would be so kind as to let you borrow her knickers for instance? That would give you at the very least some cover”
What is Rachels solution?
- No further chapters
Rachel's Bad day
A slice of life of all things gone wrong
Meet Rachel, a popular high school senior eagerly counting down the days until graduation. Join us as she navigates the final months before entering the real world, repeatedly finding herself in a series of humiliating and compromising situations.
Updated on Oct 9, 2025
by KizzKizz86
Created on May 14, 2024
by KizzKizz86
- 94 Likes
- 23,983 Views
- 79 Favorites
- 34 Bookmarks
- 22 Chapters
- 5 Chapters Deep
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