The Party’s Ripe for Caning Ch. 05


This is a series of stories about the impact of the new female teachers at the traditional school for boys 18 and over, Hamilton Hall, dedicated to preparing them for college but insistent on retaining corporal punishment. The school first hired Linda Crawford and now has both enrolled girls over 18 and brought on two more female teachers. There is some reference to bodily functions and significant physical punishments, so if those things are offensive to you, read no further. All characters are 18 or over.


Annabel Lansing was thoroughly enjoying her first term teaching at Hamilton Hall. Annabel had been a clever student when at university in Britain and had learned how to teach effective while controlling a classroom at two of England’s premier “public” schools (which in the fine English obscurantist tradition, of course means famed private or independent schools).

While Annabel had not gone to a school where girls were disciplined physically—by the time she came along, Britain had pretty much abolished caning and all corporal punishment—she had learned about it from older teachers in the schools where she got her initial pedagogical training there. And the statuesque red-haired Annabel had even had the opportunity to spend a term visiting a renowned private school where teachers were still permitted to use the cane in their best judgment.

Annabel taught both history and world literature courses at the school and was regarded by Mr. Henderson, the headmaster, as a valuable addition to the faculty because of her breadth of subject capability. Pupils soon became aware of her strictness under her smiling countenance.

One girl found out early in the term when Miss Lansing denied her request to go to the girls’ room after several girls had disappeared there and had to be retrieved by a prefect. When this girl who genuinely needed to use the toilet pleaded and was still refused permission by Annabel, she proceeded to pee in her seat and Annabel came by to observe both the tell-tale yellow puddle under her seat as well as the girl’s poop-filled panties. She was now dispatched with another prefect to the girls’ room.

That day, Annabel presided as Duty Mistress for the first time. The Duty Master or Mistress was in charge of the after-school disciplinary session to which other teachers would send misbehaving pupils. Mr. Henderson encouraged use of this procedure to avoid extended interruptions of classes for punishment purposes.

Annabel arrived at the Duty Room, well outfitted with punishment implements and add-ons. The two prefects assigned that day were waiting for her. They were Elaine Winters and Barry Jordan, two third-year students. Both were experienced in serving the Duty teacher so they presented the list of those sent to the room for disciplining.

“First, there’s Deirdre Turner and Ken Nelson, the two who misbehaved in Miss Wortham’s class. She has sent them here for further disciplining. And then there’s Laurence Tisdale, whom Mr. Kent has referred for looking at his neighbor’s test paper. Finally, Miss, there’s Susan Smithwick, the girl who lost control of her functions in your class. We expected you would send her here when we heard how badly she behaved,” Elaine said rather bluntly.

“Sounds like a relatively simple day then here,” Annabel responded with a pleasant smile. “We’ll deal with the pair from Miss Wortham first, but bring everyone in right now at the start.”

Barry and Elaine were surprised since usually pupils were summoned in sequence, but Barry went to the door and motioned to the anxious four to step into the discipline room. They stepped in and Annabel faced them with a stern look.

“All right,” Annabel said, in her sternest tone, as she stood at the desk where her thin cane lay menacingly so all could observe its presence. “I want all of you to line up there facing the wall, then the boys will lower their trousers and shorts, and the girls will lift their skirts and lower their panties. Then bend over toward the wall. You needn’t grasp your ankles but I want to see four bare bottoms facing me.”

All complied quickly, as they realized that the new teacher was going to be doing things differently. Those who had experienced the classroom discipline of the three female teachers were very worried about what would follow, in view of the severe punishments the three had already imposed. Word had spread speedily, as it always does in these school settings.

“You two were sent by Miss Wortham,” she began, meaning Deirdre and Ken. “I gather you were so ill-behaved as to be conversing during her class.”

“Miss, respectfully,” Deirdre, who had never been disciplined by a Duty Master or Mistress before, managed to respond, while remaining bent over, “Miss Wortham punished us quite severely by making us assume that new position—the murga position I believe it is called. Please consider limiting our punishment here. That was an awful way to punish us for just talking, which I admit we shouldn’t have been doing.”

“Turner,” Annabel replied Anadolu Yakası escort crisply, “and this goes for you, too, Nelson,” she quickly added, “those who are sent here in no way are permitted to question the decision of the faculty member who has awarded them this punishment. It is then in my sole discretion to determine the appropriate discipline here and I am not at all pleased by your arguing about Miss Wortham’s imposition.”

“I intend to punish you appropriately,” Annabel then stated quite bluntly.

She then motioned to the two prefects to hand her five of the ginger figs kept in the storage cooler in the Duty Room. Elaine marveled at the clear intent of the request: that Miss Lansing intended to fig all of these misbehaving pupils as an opening imposition.

Annabel now stood first behind Deirdre, who was the furthest at the left end of the lineup.

“I’m now going to fig all of you for the duration of this session,” she said. “For those of you unfamiliar with this imposition, it means you are getting a ginger stick inserted in your anus. The sting will remind you of why you were sent here. Anyone who pleads for its removal will have their regular punishment doubled.”

Annabel took one of the ginger sticks, which Elaine had lubed at the business ends, and gently inserted it and slid it into Deirdre’s cute little anal rosette. Deirdre let out a little cry but otherwise did not move or shout out.

Next, Ken felt the insidious ginger fig pushed into his anal opening and clenched, only to open his cheeks as he felt the ginger begin to sting him inside.

“Yes, boy,” Annabel commented, “the ginger fig usually cuts down on clenching like you just tried.”

Next she placed a ginger stick neatly into Laurence Tisdale’s boyish bottom-hole and he cringed but neither clenched nor made any noise.

Finally, there was Susan Smithwick, who started crying softly the moment Annabel deftly placed the fig into Susan’s petite little anus.

Addressing Deirdre and Ken, Annabel announced, “You will both sit yourselves down over there and wait while I deal with the others.”

“May we be excused while that happens?” Deirdre daringly inquired.

“You absolutely may not,” Annabel, now really annoyed, snapped at her. “Both of you sit down over there right now unless you want added punishment for your effrontery.”

Turning to Laurence, Annabel began, “Tisdale, apparently Mr. Kent caught you cheating. That is a significant offense, of which I’m certain you are fully aware.”

“Yes, Miss,” the boy responded quietly. “I didn’t intend to cheat and I didn’t cheat, Miss. I did glance at Harry’s paper but Mr. Kent caught me before I could see anything. You are right to punish me, but I hope you can recognize that I’ve never done this before and didn’t get anything unfairly as a result.”

“Tisdale,” Annabel now intoned, “you intended to cheat and only Mr. Kent’s speedy intervention stopped you. Now position yourself over the horse over there,” she ordered, pointing to the punishment horse.

Tisdale complied without further argument, and Elaine and Barry quickly secured his hands and feet with the leather straps on the horse.

Annabel then picked up the thin punishment cane, lay it across his thin bottom, and applied three quick strokes to his pale cheeks, quickly and one right beneath the other.

Laurence gasped then screamed at the third stroke.

“Good, Tisdale,” Annabel remarked, “I see I’m having a good effect on you.”

Elaine smiled at Barry that connoted her feeling that Miss Lansing was certainly up to the requirements of an effective Duty Mistress.

Annabel now resumed her caning of the boy, and lay three more strokes, diabolically lower on his bottom near the crease with his thighs and now he screamed at each painful stroke.

“I’m letting you off with a sixer this time, Tisdale,” she now stated, “and you’d better keep your eyes on your own work from now on or you’ll be quite a sorry young man if I see you here again.”

“Yes, Miss,” he quickly acknowledged.

“Winters, remove his fig,” Annabel directed and the senior prefect complied and extracted the ginger stick from Laurence’s anus, watching as it emerged with a slight popping sound.

“Pull up your clothes and you may go,” Annabel said. “Elaine, see that he signs the book; Smithwick, you’re next.”

The surprised Susan Smithwick stood and walked to stand in front of Miss Lansing, close to tears.

“Miss Lansing,” she managed to get out, “I thought that being embarrassed as I was this afternoon in your class was punishment enough. Can’t you let me off after that horror?”

“Smithwick,” Annabel said sternly, “you lost control when you were not allowed to leave the room and you know that you are expected to take care of your personal needs before class.”

The girl gasped at the response and Annabel now told her to bend over the horse so that the prefects could strap her in.” Susan blanched and asked, “Miss, in front of everyone, with Anadolu Yakası escort bayan the boys” she pointed to Barry Jordan and Ken Nelson—”seeing this?”

“Smithwick, get over that horse now or you will be very sorry if I have to have Winters lower them for you. Just for that, you will keep the fig inserted during your punishment,” she said very firmly.

Susan rapidly complied and was now bare-assed over the horse, the ginger stick looming prominently from her cute anal opening, and the prefects strapped her legs and arms in.

Annabel stepped over and retrieved her cane. She laid it on Smithwick’s bottom and slowly applied six stinging strokes to the girl’s bare cheeks. Susan was stalwart for the first two and then began pleading for the caning to end.

“Smithwick, I’m quite tired of your whining,” Annabel said very crossly. “For your constant complaining, you will be wearing punishment panties for the remainder of the day and all day tomorrow. You will report to me tomorrow after class wearing them.”

Elaine looked amazed at the teacher’s imposing a punishment the prefect had rarely seen imposed in her time at Hamilton Hall. She efficiently walked to the cabinet where supplies were kept and took out a pair of small pink panties that had two small plugs—meant for vaginal and rectal insertion—attached in the proper spots in the gusset. She then handed these to Miss Lansing.

“Take those panties all the way off, Smithwick,” Annabel ordered.

The girl complied, holding her regulation school knickers in her hand.

“Now put these on,” Annabel directed. “Winters, help her pull them up so the…inserts are in the correct openings.”

Elaine smiled at the stricken Susan as she helped the latter step into the little panties and tug them up, carefully aiming the two plugs at Susan’s shaved vaginal opening and her cute little anal rosette.

“Ooh, Miss,” Susan couldn’t stop herself from saying, “those prongs are right inside me and it feels rather strange…and dirty.”

“Well, Smithwick,” Annabel responded with wry flavor in her voice, “you’ve dirtied yourself quite a bit today so I think you deserve to feel somewhat soiled since you clearly have been accustomed to that state.”

“You may lower your skirt, Smithwick, and leave,” Annabel added. “And I expect to see you tomorrow wearing those panties when you arrive to see me after class.”

“Yes, Miss Lansing,” the bereft girl managed to stammer. “Thank you for disciplining me.”

“You’re quite welcome, Smithwick,” Annabel answered as the girl then departed, walking a bit peculiarly with the plugs in her vagina and anus.

“Right then,” Annabel proceeded, “Turner and Nelson, get over here. Bend over the desk.”

When she saw their bare bottoms facing her as they stretched across the desk to grasp the far side, Annabel motioned to Elaine Winters to remove the figs.

As the figs emerged, Annabel stared at them when Elaine showed them to her, grasping each by the far end that had not entered either pupil’s anal opening. Each showed traces of fecal matter that the figs had obviously encountered inside Deirdre’s and Ken’s rectums.

“You two have soiled these sticks with your filthy bottoms,” Annabel announced as the two cringed at the shame of the prefects and teacher observing that they both clearly needed to defecate.

“If I had more time, you would be given punishment enemas,” an annoyed Miss Lansing warned.

Instead, she picked up her two-fingered Lochgelly tawse, the one she had brought with her from England, and began applying snapping strokes to each bared bottom as each began to let out screams of pain almost involuntarily as the tawse marked their pale bottoms with nasty stripes.

“Miss Wortham made an example of the two of you talking in class,” she intoned, “and I intend to make you understand how unacceptable and disrespectful your conduct was. Keep those legs spread, both of you!”

The two hurriedly moved their legs farther apart, so that Annabel as well as the prefects could see Deirdre’s pubic hair and Ken’s scrotum hanging down between his legs.

Annabel now administered one of the most severe punishments known anywhere. She aimed the tawse between Deirdre’s spread legs and when she flicked her wrist, it curled upward, striking the tender flesh between the girls’ legs and the tip snapped right between her labia, smacking the introitus to her vagina.

Deirdre let out a scream and jumped up in abject pain.

“Get back into position right now, Turner, or you will be given extras,” Annabel said very crossly.

Somehow Deirdre managed to re-grasp the other side of the desk and sob softly.

Annabel now began strapping Ken Nelson’s bottom with the tawse and applied nine strong strokes with her strong arm. She decided not to aim for his tender scrotal sac but instead gave him a nasty flick right on his anus, which was still open wider from the recent presence inside it of the ginger fig.

Ken also cried out but managed escort bayan to hold his position.

Now Annabel was getting ready to conclude so she quickly ordered the two to stand and retrieve their underpants and in Nelson’s case, his rousers, while Deirdre was told to let her skirt fall.

“You two may leave,” Annabel said, “but woe betide you if I see either of you here again soon.”

The two quickly departed, barely managing, in Deirdre’s case, not to resume crying, now from the fear Annabel’s warning inspired.

After they had gone, Annabel asked Elaine and Barry how they found her approach to punishment.

“You are quite severe, Miss,” Barry said slowly, “but this school does have a reputation for imposing strict discipline.”

Elaine, who had acquired a bit of a sadistic streak in her several terms spent as an aide to the teachers disciplining misbehaving pupils, smiled as she told Annabel that the punishments seemed appropriate to the offenses and the needs of the pupils for discipline.

Annabel told Barry he could leave and the junior prefect thanked her for his opportunity to be of service and departed.

Once he had left, Annabel smiled at Elaine and told her that the female teachers believed they had need to ensure that pupils had proper respect for them, since some might have felt that the women instructors were likely to be easier on pupils who broke the rules.

“Miss,” Elaine said with a face that did not disclose her pleasure at the severity of the discipline in which she participated, “you clearly know quite well what these misbehaving pupils require and I and the other prefects feel you are helping the school mightily in maintaining good order here.”

“Have you been disciplined recently, Winters?” Miss Lansing responded.

“No, Miss,” Elaine said plainly, “because I really try not to incur punishment, as I feel it sets a very bad example for the pupils. But if you feel I would benefit from an imposition, that of course is your decision.”

“Well, I think we all can use a bit of a touch-up now and then,” Annabel said brightly. “So just for that maintenance purpose, please lift your skirt, lower your panties, and bend over.”

Elaine complied with the Duty Mistress’s orders, thinking that it had been some months since she had been disciplined at school. Inside, however, she was pleased that Miss Lansing, for whom she already had major respect, was taking the trouble to apply some punishment to her sensitive bottom.

Annabel stood behind Elaine, enjoying the view of the 20-year-old’s nicely proportioned bottom, now staring at her, complete with winking anal rosette, once the prefect had lifted her uniform skirt and lowered her black panties, an indulgence permitted to senior prefects.

Annabel sat on the armless wooden chair and beckoned Elaine Winters to lie across her lap. Once there, her bottom began to receive Annabel’s hand spanks all across both cheeks. After they reddened, showing reaction to the spanking, Annabel began running her finger down in the furrow and into Elaine’s already sopping vagina.

“Methinks you have found today’s programme quite enervating,” Annabel commented with a lilt in her voice. “Winters, do you get off on disciplining—both others and yourself?”

“Oh, Miss,” Elaine responded in a lower voice, “I’m a bit embarrassed but it does affect me that way.”

Annabel now inserted her finger into the girl’s wide open vagina and moved it expertly in and out, nudging the risen clit now and then with the lightest of touches.

Elaine began to buck and soon experienced a totally recognizable orgasm on her teacher’s lap.

“I hope you feel that today has been worthwhile for you,” Annabel commented.

“Oh, Miss,” Elaine gurgled, “thank you so much. I hope you feel my service merited your kindness.”

“I did,” Annabel answered lightly, “and I hope you will thank me appropriately. You can get up off my lap now, Winters.” The teacher then rucked up her skirt and lowered and removed her panties and sat on the chair with her legs brazenly spread, disclosing her flaming red-haired pussy to the prefect.

Elaine knew Annabel wanted to feel her tongue on the teacher’s needy quim, so she fell to her knees between Annabel’s spread legs and applied her oral talents to the exciting pussy she now faced.

Annabel responded with sighs and began to move her hips slightly in response to Elaine’s nice ministrations. Soon Annabel exploded and squirted the girl in the face with her plentiful juices emerging from her fiery vagina. Annabel realized what had happened and quickly applied her handkerchief to Elaine’s sprayed face and bent forward to give the girl a deep kiss of appreciation.

“Thank you,” she smiled at Elaine. “I will be holding this session Tuesdays. Please make sure with the prefects that you are assigned to me whenever you are available.”

“Oh, yes, Miss,” Elaine responded with alacrity. “I love helping you. Thank you so much for everything, and especially what just occurred.”

She realized it was time for her to depart but was surprised when after she had put everything away, Annabel took her hand as they left the Duty Room. The teacher wisely let the prefect’s hand go when they emerged, but she knew that Elaine understood her special status with Annabel from then on during the school term.

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