The Headmaster canes a teacher for the 1st time!

The headmaster heard his secretary buzz him on the intercom and announce that his next appointment had arrived. He looked at his watch and requested that she send Miss Allen in before his secretary left for the day. The Headmaster had sent Miss Mary Allen a text requesting her presence a little after the last class concluded. Miss Mary Allen opened the door and stepped into the study, bidding her boss a good afternoon. Mary was surprised at the terse tone he used to reply, wishing her the same. The Headmaster looked up at the shapely 25-year-old with shoulder length hair framing a pretty face with small attractive features and offered her the same seat that her student, Cindy occupied earlier. Mary, who was a little sweet on her distinguished 50-someting leader, inquired what he wanted to see her about in a cheerful voice. He asked her what had happened to June in her classroom this afternoon? Mary responded by explaining that June had cut her hand with a pair of sizes, so she grabbed the first aid kit and took her to the wash room to clean and bandage her hand. The Headmaster inquired how long did this take? Mary coked her head to the side thinking before replying that she had solved the medical issue in about ten minutes. With a stern look on his face, he told her that her class had become so disruptive in her absence, that Mrs. Anderson from the adjacent class, had to go into her class to quell it. The Headmaster then reminded her that good girls were seldom sent to a privet Bording School. He added that this wouldn't have happened had she followed the procedure outlined in her teacher's manual. He cited the section from memory that required the teacher to administer what care she could in the classroom and then immediately call the staff nurse. The secretary buzzed him and asked if he needed anything before, she left for the day? He responded: "No thank you - have a good evening" with an entirely different tone of voice. Mary sunk down in her chair - this was her first month on the job and she becoming very nerves about this conversation.

He asked her if there was any reason for her not to follow the guidelines? Mary said she knew the wound had to be cleaned. The headmaster reached in his desk and pulled out the same first aid kit. He opened it and pointed to the wet-wipes and the small bottle of alcohol and cotton balls. Her eyes grew wide and she simply responded that it wouldn't happen again. The headmaster told her that he was going to give her a reason to remember this - to assure that it didn't happen again. Mary appeared scared and asked what he intended to do. He responded that the punishment he gave Cindy would be appropriate. Mary then remembered that Cindy returned to class with puffy eyes and sat down very gently. The Headmaster told her that Miss Anderson sent Cindy to him for disrupting Miss Allen's class. He added that Cindy wouldn't have been able to disrupt the class if Mary had followed the teacher's guidelines. Mary's eyes open wide as she realized his intent. But then her face softened and she looked back at him batting her brown eyes in an alluring/puppy dog innocent expression that always worked on the men of her generation. Mary spoke in her most alluring voice: "But I'm a grown women" The headmaster was unmoved; he'd seen this expression before and herd many excuses in his role as disciplinarian. He responded by opening a desk drawer and comely pulling out her signed contract. He placed the document on the desk in front of her and pointed to the provision for: "Corporal Punishment in-Lew of Termination". Mary sunk into her chair, losing her job mid semester would be a disaster. He rose and took a few short steps to his side table while telling her to remove all of her garments. She rose and started to protest, but thought better about it and slowly started to undress. The headmaster took a moment to savior the sight of her lovely shaped C-cups, slender waist and exquisite hips before he handed her restraints. After days of punishing misbehaving pubescent girls, having a woman in her prime to punish for poor judgment was a very welcome diversion for him! He told her to fasten the restraints around her wrists and ankles. She appeared nervous and fumbled with them. He took them from her and quickly ****** the restraints around her limbs.

He took each of Mary's limbs and secured them with cords threaded through the hasps in the restraints. He restrained her by pulling the cords tightly towards the D-rings attached to the sides of the desk. The position spread open her legs to expand her well rounded ass and exposed her cleanly shaved pussy. Mary felt very venerable - a feeling she hadn't felt since she was a school girl herself - but now that she was older, her emotions strangely swung from dread to anticipation? The headmaster admired her lovely young body before he picked up a light leather strap. After a few moderate warm-up swats, he came down on her forcefully with lashes alternating each cheek. Mary exhaled a low mummer with each one of the 24 lashes. Her ass was now a nice shade of red. After a welcome break, he grasped the heavy strap and came down on her with a rude lash across both cheeks. Mary immediately noted the difference in intensity with a louder mummer. Once again, the headmaster alternated striking each of her ass cheeks. Red streaks were crisscrossing her ass. But impressively, unlike her students, Mary's mummers remained relatively subdued as the heavy strap did its work.

Mary enjoyed what relief her endorphins could offer while the headmaster paused to admire the purple streaks forming across her bottom. He then reached for a Lexan paddle with two rows of holes drilled into it. He held it up for her to see. Mary face saddened, but she nodded in response. She whimpered when that paddle came down hard across both ass cheeks. Her eyes were beginning to tear up. The next one struck her right cheek followed by one on her left cheek as Mary pulled against the restraints. The headmaster continued alternating sides with punishing swats marking her red ass with white splotches. Mary was impressive dealing with the pain in-spite of the fact that this was much worse than the heavy strap. The loud thud of Lexan striking flesh followed by her whimpers filled the study. He put the paddle down after 36 painful swats without a break. However, she once again savored the endorphin rush that briefly followed. Her little ass was well spanked and already very sore. Mary didn't understand, but she felt herself becoming aroused. The headmaster noticed her wet pussy glistened in the neon lights. Deep red sores stood out from the redden damaged flesh on her bottom. Mary’s ability to endure pain impressed the headmaster.

The headmaster reached for the rattan cane, raised it up and swished it through the air making Mary cringe. He placed a leather bit in her mouth and stepped back to allow him to step into each stroke – assuring maximum pain. Several moments later, he forcefully swung it into the middle of her sore ass. Mary cried out loudly in response; the pain felt like it split her ass in half. The second stroke fell just below the first stretching another welt across her little bottom. She continued to whimper loudly with each assault of the cane. Tears were running down her face to drop on the desk as the headmaster continued to march the cane down her bottom. She clamped down on the bit hard responding to the very painful experience. A thick white line quickly rose to form a purple welt each time the cane fell on her bottom. After the first dozen strokes, the overwhelming pain of the cane embracing her sore skin caused her whimpers to graduate to loud cries. The headmaster was finely getting the results he wanted. He paused after 18 strokes and Mary was thankful that she could enjoy the little relief her endorphins offered during this brief respite. However, the remaining 18 strokes were incredibly painful. The relentless assault on her ass continued to be punctuated with the fall of the cane ripping into her flesh. Her eyes were getting puffy and her arms were fatigued from pulling at the restraints. Her jaw was sore from clamping down on the bit so hard. Mary was bowling with a study stream of tears dropping down to form a pool on the desk at the conclusion of her caning. She was left restrained, bent over the frame relishing the little relief her endorphins could manage for a several minutes. Her ass was covered with deep welts; but her pussy was now dripping her arousal on the floor. The headmaster smiled looking at her arousal as he attended to her welts with an ointment.

The headmaster unbound her and gently lifted her up. Mary was unsteady on her feet and he had to hold her in an embrace for several moments. As soon as she gathered strength, she pushed her pelvis against his as hard as she could. He told her that she took her punishment well. Mary thanked him for the complement before timidly reaching for his erect member through his robe. Mary asked him if he'd like her to properly thank him for punishing her. In one quick motion the headmaster removed his robe and unzipped his trousers and unclasp his belt. Mary smiled at the sight of his erect member when he dropped his boxer shorts. She bent back over the desk so he could take her from behind. Her right hand went to work on her clit as soon as he was inside of her. The effect of his pelvis striking her sore ass excited both of them and they quickly came in heavy breathing with her body in spasms below him. He withdrew, but Mary continued to finger herself. The headmaster picked up the light strap and applied enough force to inflame her welts as she revealed through one orgasm after another experiencing a seesaw of emotions. When the pain became overwhelming, she'd cum again and then the cycle would repeat. How did he know she'd respond like this? When the last spasm subsided, he put the strap down and finished undressing as she collected herself. Then Mary straitened up, realizing that she'd never been so promiscuous, felt this sore or had this many orgasms. She coked her head to the side again in thought reliving the sensations of afternoon. Suddenly, her face brightened and she ask him if he'd like to do this again in two weeks? As they embraced, he replied: "I'm certainly up to it if you are - You should heal completely over a period of two weeks." Mary nodded her head and responded: " Let's make it date then!? He replied: "My pleasure" and hugged her harder. Both of them fell silent as they enjoyed the skin to skin embrace with Mary's breasts pushed tight against his chest.