Amy Price shivered, more due to nervousness than cold. It was 4 o'clock, and she had been about to leave school for the day. Time to go home, relax, catch up with some of her friends. But as she walked alone down the corridor, a heavy, oppressive hand had landed on her shoulder.
"Miss Price, is that make-up?" The voice was stern, unnerving, powerful. It belonged to the headmaster, an imposing man. Amy would guess he was in his late forties, but it was hard to tell. His streaked grey hair contrasted with his youthful, athletic body. "Well?" he asked.
A small part of Amy wanted to tell him to fuck off; that it was bullshit that an eighteen year old girl couldn't wear make-up in the school. But she felt minute, like she was shrinking in the presence of his six-foot form. She managed a tiny, guilty "yes, sir."
"Come with me, Amy" said the headmaster.
She was lead down the corridor, the headmaster's oppressive presence driving her through the deserted halls as she approached his office. The headmaster opened the heavy oak door with ease, and Amy entered. The office was somewhat Victorian, dominated by a heavy wooden desk. The room was darkening in the Autumnal afternoon light, but she was grateful for the small mercy of the electric heater, warming her as she stood in the centre of the room. She gulped.
"Miss Price, are you aware of the severity of breaking the rules in my school?"
Severity? It was fucking make-up. Did he just hate her or something? "Yes, sir."
"Are you aware of the punishment for wearing make-up in school?"
A small warning? That's what most girls seemed to get. Didn't seem wise to point that out, though. It could be interpreted as sarcasm. He didn't like sarcasm.
He slid the lock on the door shut, almost casually. He then looked her straight in the eye. She could have sworn there was a cruel glint in those dark eyes as he said "the maximum punishment is a caning."
Amy gulped again. She had never been caned before. It was rare she got into trouble at all.
"H... how many times, sir?" Amy managed.
She saw a sadistic grin struggle to spread itself across her headmaster's features.
"Until such time as the member of staff delivering the caning considers the punishment fulfilled."
"B... but..." she stammered.
"Bend over, Amy." His tone was authoritative, the result of many years of commanding his obedient staff, although Amy could now testify they may well be more afraid than loyal. Almost in a daze, she bent over the desk. Something was brushing the front of her shins.
"As this is your first time, measures will be taken to ensure the punishment is delivered properly."
With that, the headmaster knelt down next to Amy's legs. She felt belt-like leather straps tighten around her calves, and she found she couldn't move her legs if she tried.
"Do not struggle; it will only make things worse."
A third strap was fastened around her torso, forcing her to remain in position. She then felt her skirt being pulled up, revealing her white panties to the world. Please make him let me keep my panties on, she thought, half-praying. There was no such luck, as they were slowly pulled down. She hung her head in embarrassment, her bright red cheeks mirrored in the polished desk.
Then there was a tap on her arse. A single, light, rear tap. A preparatory, aiming stroke perhaps. Amy didn't know. She didn't care. All she knew was that this was real. She was exposed, completely at his mercy. And about to experience her first caning. She gave a sharp intake of breath and her eyes widened in pure fear.
Then it happened. A single, powerful blow. Her eyes screwed themselves shut, and she bit her lip hard. The cane drew back, but it had left its mark. Burning pain had erupted across its length, stinging, like tiny flames were dancing along the stroke, sadistically licking at her.
A second stroke was delivered with the same deafening crack. Her forearms tensed, nails digging into the palms of tight fists. A gasp escaped her as the blow hit. A third swiftly followed it, bringing more pain, spreading across her arse. Then came the fourth and fifth, even faster. She was sure they were getting harder, too. The sixth caused tears to break loose, smearing her eyeliner, leaving black trails running down her face. She didn't cry out loud. Not yet. Her lip was bloody where she had bitten into it.
"That's six, Amy."
She wished she knew how many more there would be. She didn't think she could take many more. She clenched her fists again, mentally preparing herself for the next blow. Nothing came. Was it... over? She hardly dared believe it. The headmaster was standing in front of her now. He had put down the light wooden cane he was using. Amy sighed in relief. Then he picked up a heavier, darker cane. A cruel-looking thing. "I don't think the punishment is getting through to you just yet, so this cane shall now be the one used." Amy just stared at it, struck dumb by fear. "Do you understand, Miss Price?"
"Y... yes sir," she stammered.
And then the next blow came. It tore through her skin. She cried out in pain, tears flowing freely. Then the next came, and she began sobbing through her punishment as blow after blow rained down upon her, each one punctuated by her agonised cry. She'd lost count of how many there had been, but the pain was unbearable. Another one landed with an almighty crack and her back unwillingly arched, straining against the restraints.
"P... please Sir. I can't take any more" she whimpered. She felt pathetic. The headmaster moved around to her face. In her current position, her eyes were level with his groin. And she could see that there was a huge erection tugging against those trousers, wanting to be free. He was enjoying this?
"Oh dear Amy, I'm afraid you're only halfway through your punishment."
"I... I can't take any more, Sir. Please, I'll do anything."
Her voice was weak, small. It seemed to spring forth without her trying to make the words. "I could suck you off, sir." She could hardly believe she'd just said that. She'd never given a blowjob in her life, and she didn't particularly want to. Especially not for him.
He reached into a draw on one side of the desk, pulled out some strange device. "Open your mouth, Amy."
She did it, desperate to avoid more pain. The device was forced onto her. It was a bizarre thing, somewhat like a harness. She found she couldn't close her mouth with it on, but there was a large hole in it that she found she could breathe through, and put her tongue through if she wished. She probed it nervously. It seemed quite wide, stretching her mouth uncomfortably. The headmaster smiled. It was a terrifying smile. The sort of smile you'd expect to see a medieval torturer flash just before he took out some ancient, cruel device. The headmaster freed his huge erection. He grabbed both sides of her head, and, without warning, forced his way inside her mouth. She gagged and choked at the rough throatfucking, desperately attempting to move her head away from his cock, but she was still bound in place. The headmaster kept his firm grip on her head as he thrust his way into her mouth. She couldn't breathe. It was too much. She was getting light headed. Starving for oxygeb, despite the meagre scraps of air which managed to find their way inside her through the brutal assault on her throat. Suddenly, the cock was withdrawn, the strange gag removed. Amy attempted to suck in the air, but she spluttered as she recovered from her ordeal.
"My my, Miss Price, it would seem you aren't very experienced." He looked down at her, face fixed in mock disappointment. Amy said nothing, her eyes were fixed downwards and her chest was heaving.
The headmaster walked around behind her again.
Please, God, no more caning, thought Amy. The stinging was starting to subside, she had no desire to have it return. She waited, but no pain came. Then she had another thought. He's not going to...? No, no he can't. Oral is one thing, but he wouldn't actually penetrate her pussy, would he? Surely not. Her question was answered with an unwelcome finger, probing at her arsehole.
She gulped. Anal. She had once watched it online out of pure curiosity. Even thought about it while pleasuring herself, once or twice. But fantasising and doing are different things, and she was not prepared to do it. The finger found its way inside, pushing on regardless of her pleas to let her go. It was soon joined by a second. They felt huge inside her, tearing her open. Then his fingers withdrew. For one brief moment, there was nothing, no pain, no penetration. But then his hands were on her hips. The tip of what could only be his cock pushed at the entrance to her arsehole. She was about to be taken anally, and there was nothing she could do about it. Desperately, she struggled at her restraints, but to no avail. Then she felt it, forcing its way into her. It was huge; it seemed to rip her in half. The tears started to flow again, and she threw her head back and screamed, screamed in agony as he assaulted her, used her tight arse for his own pleasure. He began to speed up, then she felt a hand. It grabbed her hair. Her head was yanked backwards. She had never felt so degraded, so worthless. The tears kept falling. The Headmaster was grunting. He was getting close, she guessed. Her eyes were screwed shut. Then suddenly she felt him withdraw. She felt peculiar, confused. Had he came? She hadn't felt anything. She opened her eyes to see his huge weapon pointed at her. He was stroking it quickly, as if pumping a shotgun before firing it. Too late, she realised what was about to happen, and her eyes widened in fear. She then realised that this was a huge mistake as soon as a huge, sticky load was fired into her face and into those deep brown eyes. His hot jizz ran down her face, mixing with the tears. She couldn't see much, her eyes stinging. She felt the straps around her legs and torso being undone. She stood up shakily. Over. It was all over. And then she collapsed.