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Ross was always very nervous when he reported to Miss Devenish. A caning was inevitable. After all, that's why he went. But he had no reason to be any more nervous as he pressed the doorbell this time, apart that the strange craving inside him seemed stronger than usual. Little was he to know that Miss Devenish was also in an unusual mood. She was always in the mood to wield the cane and place a few colourful stripes across a bare bottom, but today she was in the mood to administer a very severe thrashing.

Ross had reported to Miss Devenish on six previous occasions. She was an elegant and attractive lady in her mid-forties. Well- spoken and educated, she described herself as a professional disciplinarian, and she was exactly the right person to reacquaint her clients with the strict headmistress they so dreaded, but craved. She and Ross had developed what she considered a very enjoyable scenario. Ross reported to her for adult tuition in English Language. The lessons were of an hour in duration and Miss Devenish's mastery of her language made for tuition periods that were genuine in every respect. She would always stress that she expected perfection from Ross and always warned him at the start of the lesson that anything less would result in a caning. Ross always did his best, and he was also well educated, so reasons to cane him were few, but of course, Miss Devenish always found fault somewhere, so Ross's bottom always received a few sound strokes of the cane.

Today, however, something was different. As Ross waited nervously for the door to open his mind was in a bit of a turmoil. He had the insane desire to provoke Miss Devenish a little, perhaps by producing work that was uncharacteristically sloppy. He had never yet been caned on the bare bottom, the worst he had received was six of the best across the taut fabric of his trousers, and while that stung like the devil, today he felt he needed to feel a stroke on the bare. He secretly craved the humiliation of having to bare his bottom to Miss Devenish, then bend over and take the cane. The trouble was, he felt unable to ask. Miss Devenish and he had developed a thoroughly decent relationship. Everything was prim and proper. Bare bottoms seemed most inappropriate.

"Good afternoon, Ross," said Miss Devenish, as she opened the door to see Ross nervously biting his lip. "I trust you've been endeavouring to improve your handwriting, as I suggested when you were last here?"

"Yes Miss Devenish," he replied.
He failed to notice the slight disappointment in her face before she turned to lead him to her study.

Ross took his seat at his student's desk in the now familiar dark oak panelled room, while Miss Devenish took her seat at her own desk, facing him, and began to review his past written work. His eyes drifted from the notepaper in front of him to the umbrella stand in the corner, containing a variety of canes. One of which, he knew, he would be feeling across the seat of his trousers before the hour was over. He shuddered at the thought, but it was why he was here. It's what he craved.

"Looking at your last written essay, Ross," she said, looking up from the paper on her desk to regard him with her cool, blue eyes, "I can see that we need to work hard on your handwriting. It is simply not neat enough."

"Yes, Miss Devenish," he replied.

"Very well. I intend to spend this period concentrating on just that. I want you to write in your very neatest handwriting 'Untidy handwriting can usually be improved with the persuasion of the cane.' You may begin. In your neatest handwriting, please. Bring it to me when you have finished, and don't forget that I will have no hesitation in using the cane if your work is less than satisfactory." "Yes, Miss Devenish."

Ross picked his pen then began to write. Miss Devenish always made him nervous, so it was difficult to write with a steady hand,
but today, with the thoughts of provoking her filling his head, he was even more nervous. The finished result was not particularly neat, but it was probably the best he could do. He rose to his feet, then took the few steps to her desk, then placed the sheet of paper in front of her.
"Not good enough, Ross," she said, after studying his work for several seconds. "In fact it's even worse than the rather sloppy work you produced last time you were here. I think I will have to bring the cane into use earlier than usual."
Ross felt a wave of fear run through him. She normally caned him at the end of his lesson, just before he left. She would usually lecture him, explaining that his progress had been unsatisfactory and that she had no option left to her but to cane him. This time he had been here for less than five minutes, and the cane was already about to be put to use.
"Go and stand at the front of your desk," she said, firmly, as she rose to her feet.

With his legs feeling a little unsteady under him, Ross took the few steps towards his desk, then turned to see Miss Devenish selecting a cane from the umbrella stand. His pulse began to race as she selected a cane of medium length and diameter. It looked like the one she had used on him last time and it stung like the devil. The colour drained from his face as he saw her replace the cane, then select a longer, heavier cane. She'd never used anything as severe looking as this before!

"Yes," she said, flexing the cane into an arc, "I think I'll use this cane today."
For the first time, Ross saw a sadistic glint in her eye. A slight smile formed on her face when she registered his fear.

"Bend over the desk, grip the seat," she said quietly. "Stay in position until I give you permission to rise."
Dreading what was to come, Ross slowly bent over the old wooden desk, feeling his trousers tighten against his bottom.

"You will receive one stroke on this occasion, Ross, but I warn you, it will be a little harder than you have experienced in the past. You may find it surprisingly painful, but I have decided that this is what you need."

Ross felt Miss Devenish slowly raise the rear vents of his jacket and fold them up over his back, then he felt her gentle hand smoothing the taut fabric covering his upturned bottom. She had never done this before.

"I'm just making sure your clothes are not offering too much protection, Ross. I want to be sure you really feel this."
Now he was really scared. This was not what he was expecting.
He tensed as she took her position to his left. His whole body twitched involuntarily as he felt the cane placed across the centre of his bottom.

"Remember, Ross," she warned, "Stay in that position exactly until I give you permission to rise. Failure to comply will result in the punishment being repeated."
Ross's face screwed up almost as if in pain as he anticipated the cane stroke. The cane was gently tapping across the seat of his taut trousers. Miss Devenish looked down at his offered bottom with a look of determination and concentration.

The cane stroke was like nothing he had ever felt before. As the heavy rattan bit deep into his bottom cheeks, and a puff of dust was expelled from the fabric of his trousers, he felt a searing line of agony eat into his flesh. He gasped and gripped the seat as hard as he could to stop himself rising up. The pain seemed to eat in deeper and intensify as the full effect of the cane made itself felt, before gradually fading to an intense burning.

"You may rise," she said quietly, after about ten seconds.
As he looked briefly into her eyes, through his own shocked and watery eyes, he again saw that sadistic glint. He was terrified, but VERY excited. He knew he needed this. He knew it was going to get worse and he needed it to. Miss Devenish knew it to. Unspoken signals had, in that brief eye contact, passed between them, something special was under way and both parties craved it.
"Let's see if we can do better with exercise two, Ross," she said, as she took her seat, placing the cane on her desk. It was not lost on Ross that she had not returned it to the umbrella stand.
"In your very neatest handwriting, Ross, I want you to write 'For some people, only very hard canings will produce the required result.' I expect a vast improvement on your previous very untidy effort. Be in no doubt, I can and will apply this cane more severely that you imagine."
Her hard eyes left him in no doubt that she meant it. His hand was shaking as he began to write, He could feel her eyes watching his hand and sense her glee at his inability to write neatly. When he looked down at his completed written sentence he was both frightened and excited by what he saw. The handwriting was dreadful. He simply couldn't hand it to her. He tore the sheet off the pad and was about to start again.
"You've had more than enough time, Ross," she said, coolly, "Bring me your exercise."
Cringing inside, he rose to her feet, then took the few steps to her desk. Her face was studying his as he placed the exercise in front of her. She was loving this, he could tell. Slowly, she looked down at the offending hand written text. He felt his legs go weak at the knees as he saw her hand slowly reach for the cane.
"It appears I need to add some venom to your caning, Ross," she said, "Resume your position over the desk, please."
Feeling almost sick with dread, but excited beyond his understanding, he again bent over the desk, then clutched at the seat on the other side. His bottom was still throbbing from the previous stroke. Again, he felt her lift his jacket vents then felt hand gently running over the contours of his upturned bottom cheeks. "Are you wearing anything other than a thin pair of underpants under your trousers, Ross?" she asked, as her hand continued to explore.

"No Miss," he whispered.

"Two strokes," she said, taking her position. "If you move out of position, there will be consequences. Understood?"
"Yes, Miss," he whimpered in dread.
The gentle tapping of the cane on his bottom began as she adjusted her footing. He could hear her breathing becoming heavier as she concentrated on the cane strokes she was about to administer. He knew it would be worse. Much worse.

A white hot line of fire erupted across his bottom as the cane bit deep into his flesh. Ross cried out in shock at the intensity of the pain. His grip on the seat increased and his knuckles showed white as he fought with the urge to leap up.
The pain was so intense that he didn't think he could stay down, but the fear of more kept him in place. He whimpered as the searing pain seemed to sink deeper into him as the effects of the cane matured.
"You may rise," she said, quietly.
His eyes were moist with tears as he unsteadily rose, grasping his burning, throbbing bottom. As he looked into her clear, bright eyes, he sensed again her sadistic glee. The hint of a wicked smile formed on her lips.
"Take you seat, Ross," she said, as she placed the cane on her desk and sat down.
He lowered his burning bottom onto the hard wooden seat gingerly. "There will need to be a marked improvement in your hand writing, Ross, if you are to avoid some additional very colourful marks across your bottom. Do I make myself clear?"
"Yes, Miss," he replied, finding it hard to look her in the eyes, so looking down at the paper on his desk.
"Very well, to continue. In very neat hand writing please write 'When all else fails, a bare bottom caning may be deemed appropriate'." His face reddened. He looked up to see her smiling with amusement at his discomfort. She was intending to cane his bare bottom. For the first time in his life he was to suffer the humiliation of bending over with his bare bottom exposed for the cane. How agonising would it be? He had already found the cane agonising beyond belief through two layers of clothing. What would it be like on the bare? His mind was in a turmoil. He was both terrified and excited. The power this lady had over him was intoxicating.

"I suggest you make a start, Ross," she said, "Punishment will be more severe if I am kept waiting."
His hand was trembling more than ever as he picked up then pen. "I'm sorry, Miss," he said, weakly. "I've forgotten the exact wording." "Then I shall have to think of a way to help you improve your memory," she replied, smiling. "When all else fails, a bare bottom caning may be deemed appropriate."

Ross did try to write neatly, but it was hopeless. Her eyes were on him, watching every stroke of the pen. She already had her right hand resting on the cane - the cane she intended to use on his bare bottom. As he finished writing the word he looked down at the mess that was the best he could manage. Three of the untidily written words stood out: 'bare bottom caning'. The time had come for him to experience what he had dreaded and yearned.

He thought his legs might fail him as he slowly rose to his feet, then walked to Miss Devenish's desk. His hand was shaking uncontrollable as he placed his written work on her desk. She spent some time looking into his terrified eyes before looking down at his offering. She said nothing for several seconds.

"Have you ever had your bare bottom caned, Ross?" she asked, with a slight smile on her lips.
"No, Miss," he whimpered.
"Then this will be an enlightening experience for you. Take off your jacket please."

Ross was sweating and shaking uncontrollably. He clumsily removed his jacket. Miss Devenish had risen from her seat. She took his jacket, then laid it on her desk before picking up the cane. "Take your position in front of the desk, Ross," she said, firmly, as she flexed the cane.
He was under her spell. He had no choice but to comply. He looked down at the top of the desk, dreading the next instruction.
"Lower your trousers." she commanded.

Fumbling, he reached down, then loosened his belt. With his face red with shame, he lowered his trousers. They slipped down to his ankles.

"I think we'll have your shirt off, Ross," she said, as if an afterthought.

He slowly unbuttoned his shirt, then handed it to her. She put it on the desk with his jacket. He was standing in front of her now in just his underpants. To make matters even worse, he had an erection. "Bend over the desk, Ross," she ordered, quietly, "The reach down to grip the seat. Under no circumstances lose your grip of the seat until I give you permission."

Ross lowered himself over the desk. Although dreading what was to come, he had a faint glimmer of hope that she had reconsidered his plight and might now allow him to retain his underpants to save a little of his modesty and offer a little protection from the cane. That hope was lost as he felt her fingers under the elastic waist of his underpants. With his face reddening further in shame, he felt his last remaining garment being tugged down. All he was now aware of was the cool air on his still throbbing bottom. She must now be looking at his exposed bottom, presented in the most humiliating manner, waiting for her cane.

He squeaked with dread as she took her position, then placed the cane across his bare bottom.
"It is quite obvious, Ross, that I have been far too lenient with you. I shall now rectify that. Four strokes."

Ross whimpered, then tensed. He didn't think he could take it. SWISH - CRACK!
He hissed in a lungful of air as the first cane stroke across his bare bottom bit in venomously. White hot agony sank deep into his flesh. It was worse than he could have imagined. He had never known such agony.
He cried out in pain as the cane bit in even harder, just below the previous stroke. He managed to hold on to the seat, but his resolve was being tested by the unbelievable agony that seemed to be blossoming under the skin of his bottom.
This was the hardest stroke so far and it bit into the crease at the very top of his thighs, where they met his bottom cheeks. It was too much. He leapt up, grasping his burning bare bottom. His face was screwed up in agony. Tears welled up in his eyes.

"Resume your position at once," she ordered, coldly. There was no compassion in her voice. "Resume your position at once, or I will double the number of strokes."

Sobbing with pain and fear, Ross slowly lowered himself onto the desk, once again presenting his burning, throbbing bare bottom for the cane.
She was in no hurry. She stood admiring her handiwork, flexing her cane, while he waited in dread.

"The next stroke will be the hardest you have received so far, Ross," she said, quietly, after a long period of silence. "I expect you to remain in position until I give you permission to rise. Is that understood?"
"Yes, Miss," he sobbed.
He braced himself, tightening his grip on the seat, as he felt the cane gently tapping his upturned burning bottom.
It was devastatingly hard. Once again a searing white hot line of fire sank sickeningly deep into the tender flesh of his bottom. He lost control of his hands as he shrieked in pain. They shot back to grasp the burning flesh and he half rose, before he managed to wrestle control of his body. He forced his hands back down, lowering his torso back onto the desk, as he tried to cope with the agony that was still blossoming in the wake of the cane stroke. He prayed she would not penalise him.
"You may rise," she said, after what seemed an eternity.
Gratefully, he lifted his weight off the desk. His hands went to his burning bottom and he was shocked to feel the raised weals left by the cane. He reached down to retrieve his underpants, where they had joined his trousers around his ankles.
"Leave them," she said. "I want you naked, just in case you need further punishment. Take off your shoes and socks, then take your seat."
She took her seat at her desk, where she then sat, waiting for him to comply. Ross slowly untied his shoe laces, then removed his shoes and socks, before stepping out of his trousers and pants. "There's a clothes hanger in the cupboard in the hall," she said, as he stood before her. He was very aware that he was erect. "Fetch it. Neatly fold your clothes, place them on the hanger."

The implication was clear. His ordeal was far from over. Excruciatingly aware of his nakedness and growing erection, he went to the hall cupboard, then returned, folded his clothes and put them on the hanger. He stood, naked apart from his wrist watch, facing her with a huge erection.

"Give me them to me, then take your seat," she said, as soon as he had finished.
He handed her the hanger, then gingerly lowered his very sore bare bottom onto the hard wooden seat.
"For your final exercise today, Ross, you will write a neat and concise account of what you have learned today and what steps you will take to improve your failings. I will allow you ten minutes," she said, looking at her watch, then rising to her feet. "When I return I expect to find your completed, neatly written exercise on my desk." With that she left with his clothes. He looked at his watch, then at the blank paper. His bottom was still burning and throbbing. His erection stubbornly refused to die. His mind was in a turmoil of conflicting sensations and urges
With just one minute to go before she was due to return, the paper he was looking down at still blank. In a moment of madness, driven by a mad yearning somewhere inside him, he began to scribble down his offering. As he finished his brief essay, he heard her footsteps in the hall. He just managed to place the essay on her desk, then return to his seat, before she entered the room. He whimpered in dread as she took her seat, then looked down at his completed work. Her face showed no expression as she read his very untidy offering and short:
I haven't learned anything because you've been too lenient with me, far too lenient.
"It will be an absolute pleasure to rectify this situation, Ross," she said, rising from her seat with a sadistic smile on her face.
"I'm sorry, Miss Devenish," he said, cowering in his seat, shaking with dread. "I don't know what came over me. It was a mad thing to write. I didn't mean it."
Ignoring him, Miss Devenish walked to her umbrella stand, where she selected the longest of the canes. It was over a metre long and made of a darker, thicker rattan than the others.
"I shall be using this, Ross," she said, flexing the evil looking cane as he looked on in horror. "It has far more weight the lenient cane I have just used on you, so it will bite in far deeper."

She walked to the door, cane in hand.

"Follow me please," she said.
Quaking with fear, Ross had to comply. He rose unsteadily to his feet, then followed her in dread. He knew he was about to endure agony beyond his worst nightmare, but it was what he craved.
She led him to another room off the hall. As she opened the door he saw it was empty apart from just one piece of furniture, and ominous heavy dark wooden structure, with leather upper surfaces and fitted with numerous leather straps with buckles. It was a whipping bench, and it stood in the centre of the large, bare room, on bare floor boards.
"This is a larger room, Ross. More room to swing a cane. You will find no leniency here."
Ross felt his legs might give way as she grasped him firmly by the arm to lead him to the whipping bench. He allowed her to guide him over it. Even as she began to buckle up the restraining straps around his thighs, he knew he could still escape, but her intoxicating power over him prevented any attempt. Within seconds, she had buckled leather straps around his wrists and over his back. Now it was too late. He was totally helpless and entirely at her mercy. The upper surface of the bench was concave and sloped down towards his head, raising his gaping bare bottom high. The leather straps around his thighs kept them well apart. The strap across the small of his back kept his back hollowed, exposing his uplifted bare bottom in the most humiliating manner. Whoever had designed this sinister structure had done so with just one objective - to render its 'guest' in the most exposed and helpless position for a serious thrashing of his or her bottom.
"You will never believe what I thought when I rose from my bed this morning, Ross," she said, as she took her position to his left, then placed the heavy cane across the centre of his bottom. "I thought 'I'm really in the mood to administer a very severe judicial caning'. I had no idea that you might behave so badly as to deserve one." Ross, absolutely terrified, opened his mouth to plead, then changed his mind. He needed the caning. She wanted to cane him severely and he craved to please her.
"You will receive twenty-four strokes," she said, as she adjusted her footing, with her eyes locked on his gaping, wealed and perfectly presented bare bottom. "Do you have anything to say before your caning begins?"

In a voice he didn't recognise as his own, he replied, "Very hard, please, Miss."

"Good boy," she purred, tapping the cane across his bare cheeks. A few seconds later her face turned into a grimace as she raised the cane.

The hysterical shrieking of agony began less than a second after the first, devastating stroke. A symphony of screams that rose in pitch and volume filled the room as the twenty-four strokes of the dragon cane lay a lattice of purple weals across his bottom and took Ross to a world of agony that made his earlier caning seem mild. They were both panting when the caning had been completed. Miss Devenish, face flushed with excitement and fatigue, wiped sweat from her brow with the back of her hand. She still held the cane. Ross, glistening with sweat, his shrieking now faded to a gentle groan, was still in another place.

Miss Devenish reached down to gently stroke Ross's cheek with her left hand.
"Another six, to please your Mistress, Ross?" she whispered in his ear.

"Only if you promise to make them harder," he panted in the voice he didn't recognise.
"I promise, Ross," she whispered dreamily, still stroking his face. She continued to gently stroke his face for a few more moments, before rising to her feet.

"Better make it another dozen," she said quietly, as she took her position.


You can find another free story "Always on the Bare" by Annie Bee on Literotica