#46: Carolyn's Predicament
This is a work of fiction. Names, characters, events, and incidents are the products of the author's imagination. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are consenting adults over the age of 18.
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Carolyn was in the Headmaster's office waiting for her punishment to begin. She was naked, standing with her hands behind her back and her head bowed. She could see some kind of machine with a metal rod extending toward her. She had no idea what it was for, but she could see that it was plugged in and had several dials.
The Headmaster took her breast in one hand and rubbed her nipple until it stiffened. Then he attached a clamp and tightened it until she winced in pain. He attached a second to her other nipple and forced her onto her hands and knees. When he affixed a flexible dildo onto the end of the rod, she began to understand.
"Open your mouth," he commanded. He grabbed a handful of her hair in his fist and pulled her forward forcing the dildo deeper into her mouth. Then he attached a leather cord to one of her nipple clamps, ran it through a hole in the rod, pulled it taut. and fastened it to the other clamp. Her large breasts were pulled toward the machine. Carolyn wanted to move forward to relieve the tension, but the dildo was already making it hard for her to breathe.
The Headmaster adjusted one of the dials and the machine began to hum. The rod - a piston actually - slowly extended, pushing the dildo into her throat. Just when she thought she could take no more, it began to move away from her. She was grateful at first, but as the piston retracted it pulled the cord too, stretching her nipples. Instinctively she leaned forward to ease the pain, but when the cycle started over, the dildo forced her back.
He watched her struggle as he adjusted the dials. One controlled the length the piston traveled; he increased it until each stroke plunged deep into her throat, gagging her. The other controlled the speed. He turned it up high; the rod plunged in and out of her throat faster and faster.
The Headmaster let the machine run on high for several minutes while he retrieved something from his desk. When he returned, tears were running down her cheeks. He turned off the machine and unhooked the nipple clamps. The piston slowly retracted, trailing strands of saliva. Thank goodness she thought.
Then he showed her what he had taken from his desk. It was a large, dark red dildo, but not shaped like a normal human penis. Instead, it looked like a dog's, with a bulbous swelling near the base - the "knot" he called it. He coated the tip in the saliva that was dripping from her mouth. It wasn't especially thick - except for the baseball-sized knot - but it was at least 10 inches long.
"I see you recognize this. I thought it would be a suitable punishment for you. I don't have a problem with what you did, just that you did it on camera. That... could cause problems for the school."
"Please, sir. I promise I won't do it again," she begged.
"Spread your cheeks," he ordered., ignoring her pleas.
She leaned down on her shoulders and reached back to spread her cheeks for him.
"Better. Now bark for me!"
She hesitated too long. SMACK!
"Ouch! I'm sorry! Woof! Woof!"
He moved behind her and forced the tip into her tight asshole. Carolyn whimpered, but there was nothing else she could do. He slowly forced the canine dildo in deeper and deeper until he reached the knot.
SMACK! He slapped her cheek, hard, and then the other one. "It's a shame your brown skin won't turn pink. Perhaps I should get my crop and raise a few welts. Now roll over."
Carolyn rolled onto her back. He straddled her head, letting his balls drag across her face. "Use your tongue."
The young woman licked his hairy balls. He leaned forward and pulled her legs towards him, exposing her bottom. He began to thrust the dildo in and out, fucking her ass.
Shifting forward for a better grip, he felt her tongue licking across his asshole. He spread her brown lips, exposing her pink pussy. Using his fingers, he mimicked what he felt her tongue doing, sliding up and down between her lips. He penetrated her with his fingertip, expecting her tongue to do the same. When she didn't, he slapped her clit, causing her to gasp.
He spread his cheeks and lowered himself onto her mouth. She took the hint. Gingerly at first, she wiggled her tongue into his hole. He returned his finger to her pussy, again, copying her tongue. When he pushed in farther, her tongue did the same. He began finger-fucking her, thrusting as deep as he could; she tried to match his pace and depth, but she only managed an inch or two.
When he used his other hand to rub her clit, she reached up to stroke his cock. The Headmaster was far more experienced; she climaxed in a few minutes. The dildo was still in her stretching her asshole, but her tongue-fucking had stopped as she caught her breath. He backed off her face and guided his hard cock into her mouth.
He fucked her throat as he would a cunt, with long unrelenting strokes. She gagged and struggled to breathe, but he ignored her and thrust faster and harder. When he finally climaxed, he didn't pull out. She felt his cock throb as he spurted into her throat.
She was dizzy from a lack of air, but she felt him twisting and pushing the dildo. Finally, her rectum opened and the huge knot passed her tight ring. She collapsed.
The headmaster left her lying there while he retrieved a leash and collar. He affixed the collar around her neck and attached the leash. "Let's go for a walk." She struggled onto her hands and knees and crawled as quickly as she could to relieve the strain on her throat. With every step, she felt the knot in her ass.
He led her out through his garden door into the cold.
"Now, do your business. I don't want you ruining my carpet."
Reluctantly, she squatted and peed. He captured a picture before petting her head. "That's a good girl. Maybe next time I'll introduce you to Raul's dog. He's been wanting to breed him."
- Carolyn was worried about the punishment that involved rimming, a practice she was unfamiliar with.
- The Headmaster took pleasure in controlling Carolyn's anal performance, using a large, dark red dildo shaped like a dog's with a bulbous swelling.
- Carolyn was surprised when the Headmaster made her perform pet play, barking, and even cattle prodding her to simulate the act.
- The story "#46: Carolyn's Predicament" highlights the Headmaster's unusual use of face-fucking and deep throat techniques as punishment for Carolyn's actions.
- After the intense anal session and pet play punishment, the Headmaster led Carolyn out for a walk, humiliating her further by making her relieve herself on his lawn.