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The Headmaster
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Mr Strictland, Headmaster of the Clairemont school for girls did not consider himself a sadist by any means, but he drew a certain satisfaction whenever he was called upon to administer the cane to the bottom of an errant young student. The school had a fine reputation for turning out successful young women, and so, parents were willing to agree to the stipulation that the cane was still an option, and still very much in use for correcting a student's behavior here at Clairemont!
Two such canes hung on the wall behind his desk. One of them was small, to be used only for minor infractions, and the other one a bit larger for more serious offences. They were hung at a height where they would be in clear view of any young lady who might be sitting opposite him, so as to be intimidating, if not threatening. He enjoyed questioning a student and hearing the nervous tone in her voice as her eyes anxiously darted back and forth to the canes and then back to him.
His office was spacious and complete, with its own bathroom facility and a rather large mahogany desk. His desk was large enough to comfortably handle all of his current projects, as well as the occasional young lady who was unfortunately bent over the far side of it for discipline. He marveled at how most of the young women here had to raise up on tiptoes to drape themselves over and grip the far edge as he required. Indeed, the smooth bare backs of a young lady's legs, and presented in this way from ankles to knickers was an enticing view.
He could feel a firmness in his trousers at the mere thought of it. Since his wife had left him for a travelling insurance salesman, he had no one at home to turn too, and these sort of thoughts were coming more often. At such times he would go into his private privey and relieve himself. There was a low register in the wall between the two rooms, and his office door could be locked, but his secretary had a key, and he could hear if she happened to come into his office.
The tension in his loins was becoming unbearable, and he was considering a trip to the bathroom, when his secretary called, and told him that two of the students, Brandy. Mason, and Jennifer Atwell were being sent to him, and that they were suspected of cheating on an exam.
"Oh my!" he thought, looking at his watch and seeing that it was only 10:00 am. He was not looking forward to dealing with Brandy Mason again. She had been sent to him on numerous occasions and he had caned her three times in the past. The last time, he even made her lower her knickers and bare her bottom for it, which was frowned upon by some of the more prudish folks, but still considered an acceptable punishment according to school policy. She was a stubborn and rebellious young woman, shrewd and very athletic, and she would not show any fear or remorse. To her credit, she was one of their best lacrosse players, and she could take a hard caning on her bare bottom, or the backs of her sinewy thighs without a flinch or a tear that might show that he was making an impression on her. Just the thought of having her firm shapely buttocks draped over his desk again for punishment was making his loins ache once more. He could certainly think of other things he would rather be doing to her, and he sighed. Talking to her would just be a waste of time, but in the interest of being thorough he called her into his office anyway.
He grilled her for twenty minutes. At one point he even reached back for the larger of the two canes. He brandished it while she sat across from him with an unwavering expression and a reasonable answer to every question. He finally grew tired of this unfruitful interrogation of her and he told her go.
"Its a ways back to the classroom Sir, may I use the restroom please?" she asked, while holding herself as though she needed to go right away.
"Yes," he said, "just be quick about it.
He wrote down a few notes and called for the other girl, Jennifer Atwell.
Jennifer was a straight A student who had never been sent to him before. She was very shy, and she looked nervous, almost fearful as she sat across from him.
"Were you caught in the act of cheating?" he asked.
"No," she said, "We were on opposite sides of the room during the test."
"I'm told that you both came up with the same answers, word for word," he said, How is that possible?"
She sat there looking down at his desk. Now, she glanced up at him. Her eyes shifted to the canes hanging behind him and she seemed to shiver involunarily. She stammered, "I, I, d-don't know Sir!"
He almost felt sorry for her, but he had to find out the truth. Perhaps a little more fear would make her confess. He reached back and took down the smaller of the two canes, waved it in the air making little whooshing sounds and tapping it on his other hand.
"Is there nothing else you can tell me?" he asked.
"Are y you going to c-cane me Sirr?" She shrunk back in the chair and turned a shade paler than she already was.
"If you tell me the truth," he said, "I'll go easy on you." He felt like he was making progress but still, she remained silent. "Very well then," he said, standing up. "I want you to stand up, raise your skirt to your waist, lower your knickers and bend over the desk."
She hesitated.
"NOW! YOUNG LADY!" He even surprised himself by how loudly and forceful it came out. She quickly obeyed, draping herself across the desk with her pleated school uniform skirt up to her waist, her knickers down and her bottom bare. He walked around behind her for a glimpse of what awaited him. He could not believe what he was seeing. She had the most beautiful young ass he had ever seen. He was now, so torn between getting her to admit to any wrongdoing, and even so much as threatening to cane such a lovely bottom. His cock was leaping in his pants, and getting so hard that he had to reposition it while he was behind her where she could not see him. He was beginning to sweat, but still, he had to persevere!
"Are you sure that you have nothing else to say?" he asked, swooshing the cane through the air again."
He held the cane up and rested it against the back of her thighs just below the crease where her shapely buttocks began. She closed her eyes and waited for the inevitable first bite of the cane.
It wasn't working! He had tried everything to make her confess. If she knew anything she would have told by now. Still he could not cane her without being sure that she was guilty!
"Get up!" he said.
"What?" she turned, with a tear running down her cheek. "Y you're letting me go?"
"Yes," he said. "I can't cane you without being sure that you cheated!"
"I I'm sorry Sir! I've disappointed you haven't I?"
"Its alright," he reasured her. "Go back to class, I'll figure it out."
She started to leave, and then turned back to face him. "I did it," she said. "I cheated, and, I lied to you! I'm sorry Mr strictland! I deserve to be punished!"
Now, he was confused.
"I've always admired you Sir! and I was afraid to tell you!" She walked back over to the desk, raised her skirt and lowered her panties to her knees.
"B But...Now you leave me no choice! Now, I have to cane you!" He said.
Standing on tiptoes she stretched herself over the desk again, and gripped the opposite edge, leaving her bare buttocks and the backs of her shapely legs bared to his view and to whatever else was going through his mind. His balls were aching as he held the cane up and reluctantly levelled it across the center of her round bottom.
He saw that her legs were shaking. "Are you afraid?" he asked.
"Yes Sir...I know you don't want too, but please do it! I'll feel better when you are done!"
He took a deep breath, closed his eyes, but he could not bring himself to do it. He dropped the cane, and took her in his arms and held her against his chest.
"I'm sorry!" he said.
"No Sir, it is my place to be sorry. I lied to you again!"
"What do you mean?" he asked.
"I didn't cheat," she said, "But, I have always looked up to you, and admired you. I have seen so many others, sent to you for discipline, and I wondered, what it might feel like, to be punished by you...to be caned by you!" She stared up at him with dreamy eyes, and he could not help himself. He kissed her. It was a long deep sensuous kiss and she melted in his arms. She dropped to her knees with her arms about him and her cheek pressed to his pants.
He was so hard now. He knew that she must be able to feel how hard his cock was against her face. She looked up, smiled, and kissed the front of his pants.
"Punish me!" she begged.
"How?"
"Tell me what to do!" she smiled.
"Unzip my pants!" and she did.
"Unbuckle my belt!" She unbuckled his belt, pulled it free and put it in his hand.
"Punish me!" she begged again, more urgently than before.
"Take my cock out in your hand!" and she did so with a smile, and kissed it, right on the tip where it was wet with pre-cum.
Her white cotton blouse buttoned up the back, and he quickly undid all the buttons. He unhooked her bra in back, and pulled blouse and bra both down, baring her back down to her slim waist. Her pleated skirt was still up around her waist, baring her bottom.
"Is this what you crave? he asked while doubling the strap in his hand.
She smiled, nodded yes, and took his hard cock deep in her mouth.
Her naked back was pale and tender and he started out slow, bringing the strap down almost like love taps all over her bare back, ass and shoulders. As she continued to suck his throbbing cock he began to whip her harder, then harder still, until the belt was leaving red marks on her pale skin.
He was holding back and she knew it. She squeezed his hand. She wanted more! With his other hand, he held her in place by the hair on the back of her head and thrust his hips, shoving his cock deeper while whipping her even harder. Her back was covered with welts now and he was shoving his cock in her mouth until her nose was against his hairy belly.
He fucked her mouth, called her names, saying degrading and nasty things while whipping her naked back and her bare ass with his belt until he exploded in her mouth. She was covered in thick white blobs of cum, all over her face, in her hair, dripping down her small pert breasts.
"I'm sorry!" he apologized and offered to help her to get cleaned up, but she was not bothered by the mess he made of her. She dressed and left.
He couldn't believe what just happened. Just then, the bathroom door opened, and Brandy Mason stepped out!
"Well, That was interesting!" she said. "Are you going to punish me too?"
"You were in there listening the whole time, weren't you? You are really in for it now, young lady!"
"Recording is more like it Mr. Strictland! I got everything, sound and video through the register there."
"Give me your phone!" he demanded.
She handed it to him. "Its ok" she said, "I already sent the file to my computer at home." she smiled.
He sat down holding his head in his hands, knowing that he was fucked! "What do you want?" he asked. "Money"
"We'll talk about that later," she smiled as she picked up the cane. "But for now...You can drop your pants and underwear, and get in position!" She took some practice swings, swooshing the wicked cane through the air as he bent over the desk.
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Posted on : May 30, 2020
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Add Comment
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Commented on May 31, 2020
Brilliant you can be my Brandy anytime
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Commented on May 30, 2020
Nice story with many options to continue. Its a good plot and well written besides the publishing issue. Nicely done.
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