Bitter Apple

Another erotic story from the FLOGMASTER!

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Bitter Apple

(****, M/Ff, Severe, nc caning)

A teacher returns to the school she attended as a student. (Approximately 3,282 words. Originally published 2006-12.)

Emerging from the taxi, Jill Tully stared at the ivy-covered walls and black iron gate with an overwhelming sense of homecoming. She could scarcely believe she was back. Seven years had passed since she'd last crossed through that gate, and walking through it now, it was as though she'd never left.

"St. Bernard's Academy," read the sign, just as it had for nearly a hundred years.

She spotted old McAndrews, the groundskeeper, pruning a hedge in the south quadrant, and she couldn't suppress a smile. She and Billy Myers had shared their first kiss behind that hedge. McAndrews had caught them, and he should have turned them in for a thrashing, it being after curfew and all, but he'd simply told them to hurry on in before Headmaster Bailey caught them.

Entering the main hall, Jill caught sight of her reflection in the mirror by the door. She paused for a second, studying herself. For a moment she saw her old self, in her navy blue school uniform, a gawky teen with a fierce, determined look. Bright but rebellious, that's how she'd arrived. With a tremendous chip on her shoulder.

She'd lost that quickly, she remembered. St. Bernard's was extremely efficient in that regard.

Then she focused on the present.

She was pretty, she decided. Not beautiful -- she was too young for real beauty, and too conscious of her flaws -- but attractive, in a button-down-lawyer-type manner. She looked neat and proper, with her white blouse and gray vest and black skirt, and black pumps. Earrings were her only token to fashion, gold rings that distracted people from noticing the slight bend in her nose. Her haircut helped with that, too, framing her round head, emphasizing the oval of her face. Her lips were too small, though a touch of Crimson Blush helped with that. Her teeth were even and white, the results of years of being called metalmouth. All in all, she looked the prim and proper schoolteacher, even if she didn't quite feel like it.

Jill turned and continued down the hall, her footsteps echoing along the stone walkway. The main lobby was deserted, which made sense, since it was two weeks until the fall semester started. She continued, heading straight for Headmaster Bailey's office.

"And I certainly know where that is," she giggled to herself. It was strange, but walking up the corridor to his familiar den, she felt like she was back in school. She almost checked her pocket to see what the disciplinary note said.

A doughty white-haired woman sat behind a desk in front of the headmaster's door, typing on a computer terminal. "Yes?" she asked.

Jill grinned. "It's me, Miss Sarah, Jill Tully."

The woman paused, then looked at the young woman over the top of her glasses. "Tully," she said thoughtfully. Then her face broke into a gentle smile. "Why of course! Class of 1994." She clicked her tongue. "I remember you sitting by this desk, waiting to visit the Headmaster, I don't know how many times!"

"Too many," sighed Jill, blushing. She cut short her instinct to rub her backside.

"Are you here for a visit?"

"No, I'm the new English teacher," Jill said.

"You're a teacher? How wonderful!"

"Yes, it is. It's like a dream."

Sarah glanced at her computer screen. "Dennis is on the phone. Long distance. Why don't you have a seat and I'll buzz him when he's off." As Jill took a seat, she apologized, "If you'll excuse me, I'm rushing to get this letter out in today's mail. I've got until eleven o'clock. We can talk more later." She began rapidly typing.

Jill didn't mind. It felt good to sit for a few minutes. She was strangely nervous. Here she was, waiting to see the Headmaster again. She told herself the circumstances were entirely different, but it didn't shake the feeling. Her bottom tingled as though it knew what to expect when she entered that room.

She remembered, as clear as yesterday, her first visit to Headmaster Bailey's office. She was fourteen. Her mother had brought her, saying she needed the discipline of a prep school environment.

"Her grades have plummeted and she's hanging out with the wrong sort of kids," her mother had told the headmaster. "She won't listen to me any more. She does exactly what I tell her not to do. I'm at the end of my rope."

Jill stood there, feeling the strange eyes of the heavyset man with the gray mustache watching her. She tried to act tough, impervious to his stare. Her mother babbled on, but Jill wasn't even listening. She was trying to be far away, in a happier place.

Suddenly, for the first time, the man spoke. His voice was low, commanding but oddly gentle, and what he said was so out of place it woke Jill up.

"Do you like dogs?" he asked. His eyes fixed on hers.

Jill stared at him in bewilderment. She'd been all prepared for various threats, stern lectures, and dire pronouncements that she was completely speechless. Finally, she nodded. "Yes sir."

"And do you know how to train a puppy?"

"Not really. I never had a dog of my own."

"I had a dog when I was about your age. He developed a terrible habit. He used to chew everything up. My father's slippers were his favorite. He once went through six pairs in four months!"

Jill smiled and nodded, not really sure what to say.

"My father finally put the burden on me. 'Either train that dog not to chew or he's gone.' I thought would die without Brownie -- that was my dog's name -- and I wept and pleaded but my father was adamant. If the dog couldn't learn, out he went.

"I tried everything. I punished the dog, rewarded the dog, kept him tied up. But nothing worked. He continued to chew up anything he could get his teeth on.

"Finally, I heard of a product called 'Bitter Apple.' Are you familiar with it?"

Jill shook her head.

"It's great stuff: harmless but tastes absolutely horrible. Dogs can't stand it. Makes them foam at the mouth. You spray a little of this on your slippers, for instance, and he'll never try chewing on them again!"

Jill nodded, understanding. "That's good, then. You got to keep your dog."

Slowly, the headmaster shook his head. "No, I didn't. Bitter Apple didn't seem to work on Brownie."


"That's because I found out later I'd made a mistake. I hadn't used it correctly. There's a trick to using Bitter Apple. Do you know what that is?"

"No." Jill was getting tired of this. Where was he going?

"The trick, my dear girl, is to let the dog get a good taste of Bitter Apple _before_ you begin using it. See, you can't get enough of the spray on a pair of slippers to actually annoy a dog. It'd be like finding your coffee slightly bitter -- you wouldn't notice it. It certainly wouldn't change your behavior. But if you fill the dog's mouth with Bitter Apple first, he'll develop an absolute disgust for the stuff: thereafter, if he smells even the slightest hint of Bitter Apple on anything, he'll stay miles away. Guaranteed. Works like a charm."

"Oh," said Jill, nodding.

"Now that first dose of Bitter Apple, when your dog hasn't done the slightest thing wrong, may seem harsh or cruel, but in the long run, it's the best thing for the dog. Do you understand where I'm going?"

Jill felt the hairs at the back of her neck going up in alarm. He was warning her somehow. A blow from left field was heading her direction, she could feel it. She couldn't quite put her finger on it, but she knew he'd gotten her. She looked at the headmaster with a degree of respect. He wasn't as dumb as he seemed.

The man stood, and he was large. Jill felt intimidated by his size. She watched as he crossed the room to a cabinet on the wall. He opened it and her knees went weak. Inside hung four long brown canes, several leather straps, and two wooden paddles. The headmaster selected one of the canes and turned to face her, flexing the stick grimly.

Jill wanted to run, but she felt cornered. She desperately tried to remember her planned speeches and high-minded protests, but her brain was empty. She could only stare and pray she was dreaming.

"This, my dear Jill, is Bitter Apple," said Headmaster Bailey, holding up the cane. "All those who attend St. Bernard's are subject to corporal discipline. But like Bitter Apple, there's no deterrent effect if you haven't tasted it. You must develop a fear for it. You must _not_ want the cane!"

"I-I don't," squeaked Jill frantically, but she already knew she was lost. She glanced at her mother, but there was no help there. Her mother was looking extremely pleased at the idea of her daughter being given a good thrashing.

"Oh please, sir, I understand, and I promise I'll change my ways. You'll never see me in here, honest!"

"I can't take your word for it, my dear. I must give you the taste of Bitter Apple."

Tears glinted in Jill's eyes as she begged, but inside, she knew the battle was lost. It had been lost the moment she walked through the door. The man had seen right through her bravado, and that scared her more than anything.

"Hands on the desk," he ordered, and without wanting to, Jill found herself obeying. She was crying, tears blurring the room around her, but she was obeying.

"Legs apart. Step back and lean forward." His foot and the tip of the cane guided her into position.

"Mom, please," begged Jill, but her mother was a stone.

Suddenly the man's hands were lifting the back of her skirt. Jill freaked out, reaching back to stop him.

"Hands on the desk!" he roared, and she obeyed instantly, crying and wondering why she was obeying him.

"Today I'm going to cane you over your underwear," he said sternly. "That is a mercy. In the future, if you should ever need another taste of Bitter Apple, I shall cane your bare bottom!"

That horror was too much for fourteen-year-old Jill to contemplate, and she didn't resist as he tucked the bottom of her skirt into her waistband. It left her underwear-covered bottom exposed, which was dreadful, but it wasn't as bad as being naked.

"Listen to me, young Jilly Tully," said the man sternly. "You will take your caning like a Big Girl. You will _not_, I repeat, *not* remove your hands from the desk. You will stay bent over until I tell you to rise. You will not scream or dance or protest or beg for mercy. If you must, you may moan, but keep your mouth shut. Is that understood?"

Jill didn't answer, and suddenly the cane was there, tapping against her bottom, and then there was a slight swish and she felt a sharp sting across the back of her right thigh. She yelped and cried out, "Yes, I understand!"

It was surreal. Until the raw pain began to flood her nether regions, Jill couldn't believe what was happening. The strokes of the cane were pure agony. It felt like someone had branded her bottom with lines of red hot iron. She sobbed, bent over the desk, and bit her lip to keep from screaming. The only thing that kept her in position was her terror of _worse_ -- she couldn't imagine anything worse, but she was positive that Headmaster Bailey could make it even worse if he wanted.

Finally, it was over. It really hadn't taken long, at most a couple minutes, but it had felt like it took forever.

Slowly, Jill raised herself up, and Headmaster Bailey, after a brief lecture, allowed her to lower her skirt and she took advantage of the opportunity to discretely rub her smarting bottom.

"So," asked the headmaster with a bemused expression, "do you like Bitter Apple?"

"No sir!" Jill said quickly.

"Then I trust that I'll have no further need to see you in my office during your attendance?"

"Absolutely sir!" All thoughts of rebellion were gone, and right there Jill resolved to be a good girl, and never give the school any reason to punish her again.

Modern-day Jill laughed softly at the memory of the foolish girl she'd been. Oh yes, Bitter Apple had been successful -- at least in the sense that she feared and hated the cane more than anything. But unfortunately it hadn't been enough to keep her out of the Headmaster's office. That first year she'd been caned twice more, and each time she thought she would die.

As she got older she assumed she'd be thrashed less, but the opposite was true. St. Bernard's was more strict with the older girls, and the slightest transgression merited a stinging bottom. Every few months, despite her honest efforts to the contrary, Jill found herself sitting outside the Headmaster's office, waiting to be caned. The strange thing was that no matter how many times she was striped, the punishment was always horrible. She'd have thought she'd get used to it, be accustomed to the pain. But it was always bad, and she always vowed to never earn another thrashing.

The thought of being beaten made her heart pump vividly. She fidgeted on the bench, nervously rolling her weight from cheek to cheek, her mind telling her she wasn't here for the cane, but her body reacted as though she were. It made her wonder: what would the cane feel like today? It had been seven years since her last thrashing, a dozen of the best. She remembered she had promised herself she wouldn't cry, but by eight she was, and her belly was sick with dread that she still had four agonizing stripes to go.

"Jill? He's ready for you."

Jill looked up, startled. "Oh. Thanks, Miss Sarah!"

Her legs trembled slightly as she stood and headed through the familiar door. It closed solidly behind her, an ominous sound, like the click of a prison gate. There was no escape now!

Inside, the room smelled of wonderful, old-fashioned, cozy smells: leather, wood, hot tea, musty books, and linseed oil. She remembered that oil well, for she'd been forced to use it to polish the Head's canes one time.

Behind the desk sat an old man. At least that was Jill's immediate impression. Headmaster Bailey was heavier, his gray hair white. But then she recognized the familiar bright twinkle in his sharp black eyes and the somber lips bent into a stern frown.

"Back for more, are you?" he grunted.


The man stood abruptly, crossing to the cane cabinet in a movement as familiar to her as the man himself. Her knees went weak and her mouth dry. He stood, flexing a long brown cane.

"You haven't changed so much," he mused. "Taller, a little fuller down here," -- the rod poked Jill's tush -- "and you've grown into your face a bit more. Quite lovely, in fact."

"Sir, I--" Jill broke off, her eyes focused on the rod.

"Oh right. Let's get the preliminaries out of the way, shall we. Hands on the desk."

Jill wavered, then found herself obeying. She didn't know why; perhaps it was the force of habit. She stood in front of the desk, her legs two feet apart, terribly self-conscious of her ass in her tight skirt. She bent forward, her hands flat on the desk. The position was so familiar to her yet this couldn't be happening, could it? It was surely a dream. A bizarre nightmare, like dreaming you showed up at school naked and didn't realize until you were in a crowded classroom.

The Headmaster's hand carefully unzipped Jill's skirt at the back. It was too tight to raise, so instead it dropped, leaving Jill with only white panties below the waist. A hand pulled the panties up tight, exposing the lower flesh of each cheek. The cane tapped Jill's butt, warningly. Jill held her breath. Her body was incredibly alive. She could feel the blood pumping through her veins. Her underarms were suddenly sweaty, and she felt an urgent need to pee. Her last rational thought was, "It can't be as bad as I remember."

The first stroke cracked into her like a test car into a crash wall. She gasped, astonished at how much it stung. It was _worse_ than she remembered, much worse. Surely the man was hitting her harder than usual, giving her an adult caning rather than a schoolgirl one. But those ideas blurred as the rod snapped across her haunches again, leaving a stinging weal of fire behind.

"Ah! Oh no, please!"

The cane was relentless. Like a machine, every fifteen seconds, the lithe rod lashed her cheeks. Jill howled and danced, tears watering her eyes.

But somehow, and for some unknown reason, she kept her hands flat on the desk. She did not run away, did not try to protect her flaming buttocks with her hands, did not shout out that this was unfair, that she was a teacher, and he had no right to flog her.

He gave her six cuts, all whipped in as hard as he could. Jill lay gasping over the desk, her buttocks quivering in misery, tears and snot dripping from her face.

"Oh God, oh God," she kept muttering, gasping for air and writhing.

"I see you've remembered your decorum."

Jill stared. Her hands were still on the desk, and though she was wiggling madly at the furious sting assaulting her behind, she had not moved her feet or gotten out of position. "Learn something as a child, never forget it as an adult," she thought grimly.

"You're right, sir," she said, astonishment in her voice.

"Was that tight?"

"Oh yes, sir."

"You felt it?"

"Most definitely!"


She couldn't resist a smile. "The bitterest!"

"But you're a big girl now. Surely it wasn't as bad as all that."

Jill wiggled her bum. The intense burn was now a dull fire, a warmth coursing through her backside. The heat seemed to give her strength, energy. Despite the pain, she felt enriched, alive, good. She gave a deep sigh of relief. "No sir, not that bad."

"You realize that was not a real whipping, of course."

"Sir?" Panic and fear gripped Jill's heart. She didn't know what he was getting at: it had certainly felt real to her ass!

"How are whippings given in my office? Remember what I promised you after that first taste of Bitter Apple?"

Jill slumped forward weakly. "That if you ever had cause to thrash me again, you'd weal my bare bottom."

"That's right. So shall we try another six, properly this time?"

If you'd told her ten minutes earlier that she would be pulling down her panties for a bare bottom caning Jill would have told you were crazy. But here she was, doing exactly that. She didn't understand why, exactly, but it felt right. It felt like a puzzle piece perfect in its slot. It felt like she'd been searching for something for years, not even aware she was looking, and suddenly it had found her, and it was right.

She bared her bottom and bent over for six more cuts. These were juicy, the hard rod driving mercilessly into the fat of her lower orbs. The cane wealed her weals. She wept. But her tears were not of pain but of relief. She was home again.

The End