09 Sister Robertas Collar

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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The Headmaster was up early Sunday morning. He found Sister Roberta waiting for him when he got to his office. "I'm pleased to see you are anxious for your punishment, Sister Roberta."

"Yes, Headmaster. I've come to yearn for your guidance."

"As you should, Sister." He held his hand out. "You brought the hairbrush as I instructed?"

She retrieved it from under her habit and handed it to him. The wooden handle was smooth and polished, perhaps six inches long, tapered at both ends. He was tempted to smell it to see if he could detect any trace of her masturbation, but he knew she would have washed it thoroughly.

"Now I want you to disrobe, and then get on your hands and knees."

"Yes, Sir."

He leaned over to fasten a collar around her neck. "While this is on, you will remain on your hands and knees. You will not speak. And you will obey my commands. If you understand, nod your head."

She looked up at him and nodded.

"Good. Now open your mouth." He placed the hairbrush in her mouth, crosswise like a stick. "Heel, girl," he commanded, leading her out through his patio door into the gardens. She struggled to keep up, crawling after him, holding the brush in her mouth.

It was a beautiful fall morning, though quite cool for the naked dog-woman. "Let's warm you up a bit. How about a nice game of fetch?" He reached down and took the brush from her mouth, and then tossed it about twenty yards away. "Go get it girl!" he urged, smacking her ass.

Roberta obediently crawled off to retrieve the brush. It took her a minute to find it, buried under the freshly fallen leaves. As she picked up the brush, again in her mouth, she noticed one of the gardeners. He was holding his rake, and staring at her. He was an older man, with dark skin and grey stubble. A faded hat covered his mostly bald head.

He was enjoying the view but didn't seem all that surprised to see a naked woman crawling around. She wondered how many other women had been here before her. She tried to ignore the old gardener as she scurried back to the Headmaster.

She dropped the brush at his feet, panting slightly from her exertion. The Headmaster picked up the brush, and threw it again, this time landing it right next to the gardener.

Roberta stopped and looked up at the Headmaster. She didn't want to disobey him, but she didn't want to have to crawl to the gardener, naked.

"Fetch it, girl. Don't make me tell you twice.". She turned back towards the gardener. He was staring at her, not even pretending to rake. Reluctantly, she crawled towards him. When she finally reached him, he was holding the brush in one hand and rubbing his groin with the other.

"Lookin' for this, are ya?" He rasped, waving the brush. She nodded. "Not so fast. Let's see a trick first! Can ya sit up and beg?"

Reluctantly, Roberta sat back on her heels and held her hands up like paws.

"That's a good girl," he told her, petting her hair. "Now, roll over!"

She hesitated, looking back at the Headmaster. He was walking over and smiling. Not wanting to anger him, she performed the trick, rolling over.

"You're good with dogs, Raul. Think you could teach this one a few tricks?"

"Maybe. I've trained a few bitches. Not usually this old though."

"Well, I have some work to do. Why don't you keep this one for a few hours, and see what you can do with her?"

"Will do, sir. I'll bring 'er to your office in a few hours."

Roberta looked up at the Headmaster, her eyes wide open. But he had already turned away and was walking back to his office; he didn't even glance back.

Normally he had mail to read, and other paperwork to attend to, but not on Sundays. Instead, he opened his laptop, leaned back in his leather chair, and scanned some of the camera feeds.

He watched for a few minutes as Sister Anne cleaned her room. He was looking forward to another encounter with her. But then he noticed one of the students - Jennifer Martin - climbing up on her bed. Had she seen the hidden camera? he wondered.

But then she shifted a ceiling tile, took down a small bag, and pulled out a couple of candy bars. Ah, he thought, a clear violation of school rules. And Miss McCoy too, that's perfect. He rubbed his hardening cock absent-mindedly as he thought about the two young girls.

He watched as they took turns brushing each other's hair, and applying makeup - another rule violation he noted, pleased he would get to add another punishment.

He continued to rub as he watched them. Miss Martin was far more developed, with large breasts for her age. But there was something special about Miss McCoy; perhaps it was the way she handled his discipline. The way she accepted the humiliation intrigued him. He knew he would have to come up with a special punishment for her.

Meanwhile, Raul was "training" Roberta. He had fashioned a switch from some garden cuttings and was brutally striking her ass if she made the slightest mistake, or didn't follow his commands quickly enough. Her bottom was already covered with deep red welts.

To give her a "tail", he had tied his bandana to the brush and forced the handle into her asshole. Now, he was teaching her to wag her tail, by repeatedly whacking her already bruised cheeks, alternating each time. She wasn't very good; she simply couldn't wiggle fast enough to make the brush wag. "Oh, never mind," he scolded her. Frustrated, he yanked the brush out and tossed it away.

Trying to please him, she scurried after it, picked it up in her mouth, and carried it back. He took it, and she turned around, presenting her ass to him. "Well, that gives me an idea for a trick you can do," he told her. "I'll hold it, and you push yourself onto it." He held the brush with the handle pointing out. "Come on now girl, get your tail!"

Roberta looked over her shoulder, and then slowly backed towards him. When she felt the brush tip, she moved until it was pressing against her asshole. Raul held it firmly as she pushed herself back, forcing the brush into her tight hole.

"Good girl" he praised her as he pulled it out and tossed it away again. She obediently brought it back, and again pushed herself onto it "That's it," he encouraged her, stroking her back gently. He repeated the trick a handful of times before he was satisfied.

After the last one, she heard him laughing. When she turned to look, she realized he had moved the brush, and she had forced herself onto his hard cock instead. He grabbed her hair with both hands as he pounded into her ass. It didn't take long before she felt his cock throb as it pumped warm cum into her.

Finally satisfied, he pulled out and replaced it with the brush. Then he pulled her around by her collar and ordered her to lick him clean. Roberta hesitated; his cock was coated in slime and smelled as bad as it looked. But a few hard thwacks on her sore butt made her hurry to obey.

She opened her mouth and began to slowly lick his cock -- too slowly for Raul. Impatiently, he grabbed her and forced her head down until her lips were pressed against him. She gagged as his prick filled her throat, repulsed by her degrading behavior as much as by the foul smell and taste.

At first, Roberta was mortified at the humiliation. But with each thrust, her body responded to his demands, until any pretense of resistance faded. She began to suck greedily, using her tongue to lick the sweat from his balls. Finally, he grunted his approval and tucked his soft cock into his trousers. Roberta moved forward and rested her cheek against his crotch.

Raul stroked her hair and smiled at her. "That's a good girl." Grabbing a nearby bucket, he filled it with cold water and set it in front of her. She eagerly lapped as much as she could before he called her to follow. "Come on then, bitch. I better take ya back to the headmaster now, at least you do have one trick to show him."

The Headmaster heard the knock and opened his door. "All finished, sir," Raul informed him. "She's a bit slow,., but she did manage to learn one trick. Would you like to see it?" The Headmaster nodded.

"Well turn around girl, don't keep the headmaster waiting." Sister Roberta twisted around, facing away from the two men. Raul pulled out the hairbrush and tossed it out into the garden. "Fetch your tail!" he commanded. Exhausted after her long day, Roberta crawled as quickly as she could, and returned carrying the brush in her mouth.

Raul took it and held it out as the Headmaster watched. Roberta turn around again and slowly backed up, forcing the brush back into her asshole. The Headmaster smiled. "That is a fine trick, well done Raul. Now, Sister Roberta, I have some instructions for you about Sister Anne's hairbrush..."