Caution: This Sex Story contains strong sexual content, including Reluctant, Blackmail, Heterosexual, Fiction, Spanking, Teacher/Student, School, .
Desc: Sex Story: Chapter 1 - Arthur is headmaster of a school where caning is still performed. A girl is caught smoking by Miss Wilson, a young female teacher new to the school, and Arthur involves her in the girl's punishment. In the process he finds an excuse to cane the teacher while the girl waits outside listening. He discovers that the teacher is submissive and masochistic. He decides to train her as his discipline assistant.
Arthur Ash was having a good day, and very confident it would get better. The school secretary had called to tell him that Miss Wilson, the new history teacher, had caught Sharon Napier smoking. He told the secretary to send Sharon back to her class, and to ask Miss Wilson to come to his office immediately so he could find out exactly what the young teacher had seen.
As he waited, he stroked his cock and watched the screen of the security camera showing the corridor outside his office, and contemplated his many options.
Sharon was one of the prettier girls in the senior class, and so far she had managed to stay enough out of trouble that her file reflected little more than the occasional detention. He wondered if there was a boyfriend leading her astray!
Sharon smoking, oh my god this had to be a caning event! He looked across at the Implement Cupboard on his wall where he kept his canes and straps. A number six, he decided.
He put his cock away as he saw Miss Wilson appear in the screen. She was a very interesting creature, mid twenties, long black hair. Nice big breasts, she was not quite fat but certainly plump. She was apparently single, and definitely very insecure. She had joined Arthur's school straight from teacher training a few months earlier and had been getting good reviews, except that she was considered not to be strict enough with the girls. This was his first opportunity to discuss his ideas on discipline with her. She paused outside his door and adjusted her skirt and her hair, then she knocked softly and stood silently waiting for permission to enter. He was pleased that she didn't try to open the door without permission.
He kept her waiting until she plucked up the courage to knock a bit harder, then called out "Come in" and tried to steady his breathing.
As she walked into his office he admired her breasts moving deliciously inside the loose white blouse, and her short blue and white patterned skirt showing plump but sexy legs. He invited her to sit in a straight backed chair in front of his desk, and was pleased to see the skirt rise to expose her thighs despite her trying to keep her knees tightly together. He could tell that she was very nervous, and he liked that.
"So, Miss Wilson. You caught Sharon Napier smoking, eh? Well done. Please tell me all about it."
She started talking, and he held his hand up for her to be silent. He explained to her that he needed to prepare the paperwork first, and ostentatiously tore a 'punishment report' form from a thick pad on his desk. He filled in Sharon's name under 'culprit' and Miss Alison Wilson under 'Reporting Person". When he was ready he instructed her to go ahead. As the teacher recounted the events of the morning he sat filling in the report form recording Sharon's crime, intermittently looking up and asking Miss Wilson for more details about how she had caught the girl and how the girl had responded.
Each time as he raised and lowered his eyes he took the opportunity to scan her thighs showing under the skirt. As she shuffled on the hard chair trying to get comfortable, he caught glimpses of red panties! He could also see her nipples pushing through the blouse, and that surprised him because he hadn't noticed them before. Were they erecting under his inquisition? How interesting!
At last he put his pen down and sat, idly running his eyes over the attractive woman sitting primly in front of him. After enduring this in silence for a minute or two, Miss Wilson finally broke the tension by speaking.
"Sharon is in her class waiting to be called to see you, headmaster. I had a long talk with her, she is contrite but understands that she deserves to be punished very firmly. Smoking is such a bad habit and it would be awful to see her suffer from all the things that smoking can cause. I understand that you sometimes use a cane on the senior girls? She asked me about it, asked if I thought it was likely that she would get the cane for this. I wasn't sure of your thoughts so I didn't discuss that with her, but I am sure she has heard from other girls caught doing such things in the past and she seems very scared." She must have realised she was babbling because she suddenly stopped talking and sat silently, her face flushing with embarrassment.
Arthur smiled at her, trying to look cool and calm and collected, while inside his heart was pounding and he was very aware that he was sporting a rock hard erection. It wasn't just the prospect of caning Sharon, although that would be glorious. He was also aroused to be discussing the girl's imminent punishment with this attractive and inexperienced young teacher, who seemed to be responding sexually to his probing questions. He sat for a few more moments as though considering what the young teacher had said, then he lent forward with his elbows on the desk and looked earnestly into her nervous eyes.
"Thank you Miss Wilson, yes, I will certainly cane the girl. I see it as my duty to do my best to dissuade her from the repulsive habit, I am as opposed to smoking as you clearly are. Thank you for bringing the girl to my attention. Now, would you mind going to her class and telling her to report to me at one o'clock." It was only just after eleven now, and Arthur loved the idea of Sharon spending her lunch break in drear anticipation. "Make sure everyone in her class hears you tell Sharon the time when she has to report."
As Miss Wilson stood up, ready to walk out, Arthur asked her, "Have you ever witnessed a caning, Miss Wilson?"
"Oh no sir, never!"
"Well perhaps you should. When Sharon reports, why don't you come in with her and you can watch the process."
"Oh my god!" The young woman looked quite flustered at this idea, she gulped then nodded and mumbled, "Well, yes headmaster, if you think that's appropriate."
He watched on the screen of his security camera as Miss Wilson walked off down the corridor. She had a marvellous bottom, and suddenly he knew he wanted to cane that bum even more than he wanted to cane the lovely slim Sharon. He hoped that watching Sharon receive the cane would turn Miss Wilson on, although as yet he had no plan on how to take advantage of any such emotional response.
Arthur knew that a lot of the pupils found it exciting listening to other girls getting punished, so he always opened the office windows letting out onto the quadrangle, to allow them to congregate out there and hear what was happening inside. Fortunately the windows were too high up for anyone outside to actually see inside, so Arthur was able to take his cock out and stroke it slowly as he watched the clock progress inexorably towards Sharon's allotted time. He skipped lunch and sat playing through in his mind exactly what he would do with both the naughty student and the deliciously plump young teacher.
Several minutes before one o'clock, he watched on his security screen as Miss Wilson and Sharon approached the door to his office. The teacher pointed to the sofa placed outside for visitors waiting to see the headmaster, and told Sharon to sit there and wait until she was called in. Then she stepped close in front of the office door motionless, looking at her watch.
Right on time, Miss Wilson knocked on his door, and when summoned to enter she stepped inside and announced that Sharon was outside waiting for her punishment.
"Hands on her head, nose to the wall, I presume?"
"Um well ah not specifically, no, I just told her to wait."
Arthur feigned anger, and snarled at the young teacher, "Don't they teach you anything at teacher training college? Go out there right now and instruct her how to wait for punishment. A submissive posture while a girl waits conditions the girl's mind significantly. Have her stand feet together close up against the wall, actually with her nose touching the wall, and with her hands on her head."
He listened gleefully as Miss Wilson tried to sound stern, and the frightened student apologised and stepped across to the wall and stood as instructed. From the position of the security camera low down, Arthur could see how raising her arms lifted her short skirt!
When Miss Wilson came back in, she stammered, "I'm really sorry about that headmaster, I didn't know," then she asked if he wanted Sharon to come in now, and Arthur decided this was too good a chance to give up.
"No, shut the door, Miss Wilson, we need to talk. I can't believe that you never learnt how girls waiting to be disciplined should stand while waiting. Maybe I should give you a couple of strokes of the cane right now just to brush your attitude up and get you thinking like a teacher not a trainee."
To his delight, the lovely young lady went pale and stood facing him with her mouth open and her hands by her side, no trace of defiance in her attitude. When she didn't yell abuse and storm out, but instead just mumbled again that she was sorry, Arthur snapped, "Take your panties off and hang them on one of the hooks behind you."
She stood facing him for a few moments, and he feared she might refuse, but instead she just muttered, "I'm wearing panty hose sir, do I take them off too?"
"Yes, Miss Wilson, and put them in the bin by my desk. I hate panty hose. In future if it's cold wear stockings, otherwise just bare legs."
As she obeyed, Arthur quietly gave thanks to whoever was up there who made girls like this one so obedient!
She flushed scarlet as she contemplated his instruction, then slowly turned her back on her headmaster and tugged her skirt up at the sides. She balanced with one hand on a chair as she stepped out of her undies.
After dumping her tights in the bin, and hanging up her panties, the cute black haired teacher turned toward him, her face red with embarrassment. He was amused that her skimpy nylon panties, high on the hook behind her, were red with black lace trimmings, matching her lovely face framed by silky black hair. He could tell that the act of removing her knickers in front of him had caused her significant emotional stress, and he was glad that she had so readily done everything he had ordered. The young lady had potential! How far would she let him go? He knew he had to go slowly, if he wanted to keep her available in the future.
"Are you really going to cane me, headmaster?" Nothing defiant in her voice or tone, just fear and wonder.
"Yes, Miss Wilson. Have you ever had the cane before?"
"You obviously have much to learn. Come over here, let me show you the implements that I have available." He stood up and went to the wall cupboard, and waited until Miss Wilson was standing beside him. She gasped when he opened it to display his large collection of canes and straps and paddles. She watched, biting her lip deliciously, as he reached up and selected a light whippy rattan cane from a hook labelled No 3.
"I'll use just a light cane for your first experience then. Go to the middle of the carpet and touch your toes please."
Miss Wilson groaned then slowly turned and walked across his office then bent at the waist and reached her hands down toward the floor, her skirt rising behind to display a magnificent curvy bum. But she couldn't reach her toes, and apologised! "Well, put your hands on your knees, at least," he instructed, trying to keep his excitement from his voice.
"Feet apart for the cane, Miss Wilson," he said as casually as he could, as though he was just helping her with a problem with her history lesson. "Conventionally, it's feet together for the strap, and of course over the lap for a hand spanking, but always feet apart for the cane."
"Yes headmaster. Sorry, I was never taught about these things."
"Never mind. I'll only give you a couple of strokes. Four maybe. And then you can watch while I give Sharon a proper caning. It will be a good experience for you." As he spoke he lifted her skirt up and laid it over her back.
Looking down at her plump bottom, he thought how delicious it was, and how he would enjoy watching it shudder under the cane. Why had he said only four? He was sure she would take however many he chose! Well, if she wasn't going to get many strokes he would at least make sure she felt every one. He raised the cane high and brought it down hard.
The lovely girl reacted magnificently, squealing and standing up with her hands clenched to her bottom, her wrists preventing her skirt from falling back down.
"I am sure you realise that strokes don't count if you move. That's four more to come."
By the time he had delivered the four strokes originally promised, there were three extras to come! "Stand up, Miss Wilson, I think you should experience the Number six cane that I will be using on Sharon in a few minutes. Go put this cane away and bring me the one off the Number Six hook."
She was panting as she approached him, holding it out horizontally in both hands. "She can't hear this, can she headmaster?"
"Sharon? No, the walls are pretty thick. Let's have you over the desk for these next three, that's the position I will put Sharon in. Feet apart, and just hold yourself off the desk with your elbows."
She obeyed, and again he lifted her skirt over her back. That is the most deliciously cane-able bottom I have ever had at my disposal, he thought, as he raised the heavier cane high. Actually he had lied about the walls being sound-proof, he had always taken pleasure from knowing that those waiting their turn out in the corridor could hear every stroke delivered on those who had gone in before. So yes, Sharon Napier could undoubtedly hear the caning now taking place. Perhaps she assumed there was another girl in the headmaster's study, and Miss Wilson was assisting with that girl's caning.
Rather to Arthur's disappointment, Miss Wilson held her position for all three of the extra strokes with the heavier cane, so he told her to stand, and she did so, her hands again clenched to her bottom, panting.
"Hang the cane up on its hook, Miss Wilson."
He watched as she walked stiffly across the room, hung it up, closed the cupboard doors, and walked back toward him.
"Okay now you can show the girl in."
To his delight she asked if she could have her panties back, clearly implying that she accepted that he might say no. So he did say no, and watched as tears formed in her lovely big blue eyes.
"No, Miss Wilson, you will be more comfortable without them on for a while. Anyway I think it would be rather nice if your panties are left hanging on the hook for Sharon to see. It's good for a girl to know she isn't the only one who experiences corporal punishment in my office. We will pretend to Sharon that they belonged to the last girl who was disciplined in here. Well, that's true of course, but we won't tell her that you are that girl."
Surprisingly Miss Wilson didn't object. She nodded, biting her lower lip, seeming to be having difficulty talking. She opened the door, and stepped out. Arthur turned to his security camera screen to observe how she handled this. He wished he could hear what was said. He watched as Miss Wilson beckoned to Sharon, who had been waiting hands on her head as instructed, then she followed Sharon in, pushed the door closed, and stood against the wall looking for all the world as though she was about to faint.
He wondered if she would dare to sit down without permission, and contemplated making her stand throughout. But he wanted to make her sit on her welted bottom, and he also wanted to see up her skirt again, now that she had no panties on. So he turned to her and said, "Sharon, come stand in front of my desk. Please take a seat, Miss Wilson."
Arthur was struggling to avoid showing his excitement as Sharon walked nervously across Arthur's large office to stand in front of his desk. She was, of course, wearing her school uniform, pale blue blouse tight across firm young breasts under a black gymslip with pleated skirt so short he knew her panties would be on show if he made her touch her toes while still wearing them. But he had no intention of doing that. Flat shoes with ankle socks, and he pictured her going out partying each evening no doubt wearing high heel platform shoes that would display her calves even more nicely, and probably a skirt so short her knickers would be on show as she danced.
But she wasn't thinking about boys or partying now. She stood biting her lip nervously, hands clasped in front of her, looking down at the floor, while he ran his eyes over her. After a long pause he began. "So, Sharon, I understand Miss Wilson caught you smoking?"
The girl half turned, as though wanting to let Miss Wilson know how much she resented being dobbed in. But then she turned back to Arthur, nodded, and said softly, "Yes sir, sorry sir."
He hoped the trembling girl in front of him didn't realise how much he loved doing this. "You know of course how bad smoking is for your health?"
And so began a lengthy and very one-sided discussion on the evils of the dreadful weed. The girl kept nodding, occasionally responding with whispered "I know sir, I'm sorry", or "I won't do it again sir", a promise that he was pretty sure would be forgotten soon after she left his study unless he did his job thoroughly in the next few minutes. But he would do his best to imprint his beliefs on the girl's mind, by imprinting cane marks across her bottom.
He realised he had been lecturing her for at least five minutes about the perils of smoking, and he knew he was repeating himself, but he was enjoying himself. He suspected that the girl was beginning to hope that the lecture would be her only punishment. He looked forward to disappointing her! At last, realising he had talked enough, he decided it was time to cane her.
When he stopped speaking, the girl stood squirming, glancing up at him to see if he was going to let her go, but clearly aware that this was unlikely. Mr Ash had a reputation in the school, and his long whippy canes were dreaded by all the pupils. Sharon had not been caned before, but she had known since that morning that it was surely going to happen, and now she knew that it was going to happen in just a few minutes. And sure enough Mr Ash finally spoke the dreaded words.
"Now, Sharon, I am sure you know that I am going to cane you."
She nodded reluctantly, her faint hope of a pardon dashed.
"Take your panties off, and hang them on the hook behind you."
He could sense her dismay as she realised she was about to experience pain. He sensed she was contemplating pleading, maybe even wondering if she could bribe him to let her off. Surely all girls knew how readily men accepted offers of sex in return for money, or help with homework, or even a reduction of punishment. But she looked up into his eyes and could see his determination, and she was very aware of Miss Wilson her history teacher standing behind her, perhaps she was there precisely to protect the headmaster from claims of accepting such bribes. So she didn't attempt to change his mind, looked to the floor and obeyed.
Reluctant fingers gripped the hem of the skirt and slowly raised it until she could reach under it for the waist band of her knickers. He wondered what colour they would be. The hanging folds of the front of her skirt hid her panties as she drew them down, hiding them from his view until they were half way down her thighs. White. Conventional, but still delicious.
As she bent to push the panties down her long legs, her long silky brown hair fell forward, and he imagined her kneeling in front of him sucking his cock, his hands buried in that lovely hair as he thrust his cock into her throat. But no, not possible. Even without Miss Wilson sitting behind her watching, it would be far too dangerous. He knew that the closest he had ever dared get to that was to touch a girl's bottom soothingly during a lengthy caning.
He watched as she lifted each foot in turn to slip her panties off, then holding the flimsy garment in her hand she tugged her skirt down with the other hand. As if she didn't yet realise he would be lifting the skirt over her back in just a few minutes. She walked slowly to the wall, looking with surprise at the other pair hanging there, and hung her panties on the next hook. Surely she would realise that red nylon panties with black lace trim would not belong to any student in this school. She glanced sideways at Miss Wilson as she hung her plain white panties up beside what she clearly suspected were the teacher's sexier knickers.
Over the years since becoming headmaster Mr Ash had enjoyed watching a lot of girls hang their knickers on that hook, the girl trembling, sometimes already in tears. He wondered if Sharon would cry during her caning. He hoped so. He would do his best to make her cry.
The lovely girl returned to her allotted place in front of his desk, not yet knowing what position he would put her in for the cane.
"Have you had the cane before, Sharon?" He knew she hadn't had it at school, he was the only teacher authorised to cane, and he kept meticulous records of who he gave it to. But he didn't know what happened at her home. Some parents still tried to enforce discipline by old fashioned methods.
The answer pleased him. He relished introducing her to the agony that a good hard caning could induce in a tightly folded bottom! But for Sharon he wasn't going to make her bend tight, he had a special routine for smokers. But first someone must fetch the cane. Normally he made the unhappy girl do it, but now he had another idea. Miss Wilson would be his Assistant Disciplinarian. Perhaps not just today, perhaps permanently.
"Miss Wilson, please open the window behind my desk." Mr Ash liked to leave the windows of his office open when he caned girls, he loved letting the rest of the school hear the girl's cries. Now it amused him to have Miss Wilson preparing the room for Sharon's caning. Sharon stood watching glumly, well aware of why he wanted the window open.
"Thank you Miss Wilson, now fetch a Number 6 cane please."
The teacher flushed, and muttered, "Yes sir," as she obeyed, showing that she knew where the headmaster kept his canes.
"Give it to Sharon, let her feel the whippiness of it."
The younger girl's hands were trembling as she stood holding it, then in response to a sign from him she brought it to him and reached over his desk to put it down in front of him.
"Step close against my desk, Sharon. Feet wide apart, then bend forward with just your elbows on the desk."
The girl was too scared to ask why, she obeyed and when she was in position he lifted a small bin out from under his desk and gave it to Miss Wilson. Looking inside, she saw a jumble of empty cigarette packets, that Arthur had picked up from around the neighbourhood, each with it's government mandated health warning on the packet. He took one of the packets and showed it to the cringing girl. "I take it you have read these warning messages?"
"Yes sir," she stammered.
"So you know what harm smoking can do to you?"
He left the packet on the desk under her nose, and walked around behind her and slowly lifted the hem of her skirt and laid it down over her back, exposing creamy firm ass cheeks that he yearned to touch. Not yet, though, he thought, only when she was in agony might she accept a consoling stroke. And he wondered how Miss Williams would respond if he did touch the girl inappropriately.
"I am going to cane you and before each stroke Miss Williams will give you one of these packets out of the bin, and you will read out the health message on it. Loudly so anyone in the courtyard can hear, and know why you are being caned. Understood?"
"Yes sir," she moaned, and he realised she was already crying, more from the humiliation than from the fear of the pain to come.
"This will continue until you have read the messages on all the packets in the bin." He guessed she wanted to know how many packets there were in that bin, how many strokes she would receive, but he enjoyed keeping her in suspense. He knew that there were twelve packets. That was his standard punishment for a first smoking offence, although if the girl made too much fuss he happily doubled the penalty, usually applied over two successive days.
But Sharon wasn't protesting, she obediently but reluctantly read the warning on the first packet, "Smoking causes lung cancer."
"Louder, Sharon. Lift your head and call out to your friends outside." This time the girl called out the horrid message loudly and he smiled as he raised the cane. "That's better, let everyone know why you are being punished."
Sharon cringed at the thought that her friends, and her enemies, would be out there listening and enjoying her pain and shame. She had, on several occasions, been out in the courtyard listening to the headmaster administering discipline.
After pausing long enough to enjoy her distress, he brought the cane whistling down and the girl howled, no longer concerned that others might hear her. He loved the way her small bottom clenched and relaxed and shuddered as she tried to absorb the awful pain. Was this more fun than caning Miss William's larger bottom? He wasn't sure, they were both great fun.
He waited until she was settled, and then softly prompted, "Next one, please Miss Wilson."
The teacher brought across the next packet, and placed it on the desk where Sharon could read it. After taking a deep breath, the girl cried out, adequately loudly, "Tobacco smoke is toxic."
"Indeed it is." Again after a short pause the cane swished down and landed across her lovely bum cheeks with a loud crack, followed by a howl from the victim.
A few minutes later those listening outside heard the girl read, voice quavering, "Quitting will improve your health." Again the girl yelped as the crack of the cane landing echoed across the school quadrangle.
After the first six strokes, he thought she might not be too upset if he touched. He placed his hand on her bottom and she sighed softly.
"I hope you are learning something from this, Sharon," he said.
"Yes sir," she croaked, obviously trying not to cry and very aware of his hand as it ran softly over the six livid welts. He half expected Miss Wilson to protest, but didn't look her way, just stood over Sharon slowly stroking her bum. Miss Wilson didn't move or speak.
"When it's all over, I can rub cold cream into the welts, if you like."
"That would be nice sir. Please sir, how many more?"
He ignored her question, and waited for her to complain as he ran the flat palm of his hand over her bottom and the insides of her thighs. "Actually your bottom is marking up quite noticeably. I'm wondering if I should postpone the rest of your punishment until tomorrow."
He was sure she was pushing back against his hand, certainly not flinching away from it.
"That would be kind of you sir, I really don't think I can take much more now."
He smiled and decided to toy with her. "If I postpone the rest until same time next week, will you try not to smoke until then?" The finger tips of his hand were now curving down into the crack of her bottom. Her breathing was ragged, and he wondered exactly what she was thinking.
"I'll try sir," she whispered.
"Come to my office same time next week. If you tell me that you haven't smoked at all, then I might let you off the rest of your punishment, if I am sure you are telling me the truth."
"Oh god, yes sir, thank you, sir."
"But if I ever find out that you have lied to me then you will receive the full punishment in one dose, with no credit for the strokes you received today."
"Yes sir, please I won't lie to you sir."
"So would you like that cold cream now?"
"Oh god! Yes please sir."
He opened a drawer and took out the half empty jar of cold cream. Must get some more, he thought cheerfully, anticipating more canings to come. He put a big dollop on her bottom and used both hands to rub it softly and gently into the welts. But not just the welts, he smoothed it all over her lovely bottom and inside her thighs. Noting her acceptance of what he was doing, he allowed his fingers to run in the crack of her bum, gently easing her cheeks apart so he could get access, and then running a finger down under her.
"Oh jesus," he heard her say softly.
"You okay Sharon?"
"Yes sir that's nice, please don't stop."
Soon he was running fingers inside her labia, gently circling her clitoris but not touching it, and he could tell he was driving her wild! Her thighs were clenching and relaxing, and her breathing was ragged. He wanted her to beg! He wished he could see her breasts. He turned his head toward Miss Williams, and was pleased to see she was rubbing one hand against her crotch, the other cupping a breast. He contemplated telling her to join Sharon for cold cream, but guessed that would be pushing the young teacher too far.
Finally he told Sharon to stand, and hang the cane up in the cupboard. He knew she was close to orgasm but didn't want to bring her off in front of her teacher. The girl stood up, took the cane, and walked stiffly across to the implement cupboard and hung the cane on its hook. He told her to put on her panties and go back to her class.
She walked over to the row of hooks, took down her white cotton knickers, and slipped them on. Then she took down the red ones, and took them across to Miss Wilson and held them out to her. "Do you want your knickers, Miss Wilson?"
She turned her head toward Arthur, gave him a crooked smile, said, "Thank you sir," and he knew she was grinning as she left his office.