New Babysitter

By Gerste

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Josh Weisensteing was a slender, blond-haired nine year old American boy of Germanic descent and very attractive. His mother, Martha Weisensteing, announced he would have a new babysitter, while she and his father would be away on his business trip. Josh was an intelligent lad who was very cooperative and submissive. However, when his mother elaborated further, he began to bristle: "She will have absolute authority over you, and you are to do whatever she says, however strange it may seem to you, Josh."

Josh: "Yes, mom, but what could she be telling me to do that is different from all the other times?"

Mrs. Weisensteing: "You'll see." She smiled at him in a way that sent shivers down his spine. He had never seen this expression on his mother's face before. It was uncanny and unnerving. But ever the level headed pragmatist, he decided to take a "wait and see" attitude, and dismissed the strange expression as subjective interpretation, although he would not have used those words.

Josh: "When will this babersitter arrive, mom?"

Mrs. Weisensteing: "Four PM Friday night, which is tomorrow. She should be here right after you get off the bus. She's sixteen and her name is Jill Wounderad. I will leave my number with her, and she will call to inform me if you get 'out of hand.' "

Josh was almost the perfect child, so he was a little surprised that his mother should suddenly turn so disciplinarian on him. He had two sisters: Christy, who was 8, and Alexa, who was fifteen. He wondered why Christy, his younger sibling, should be exempt from any consideration. But he then dismissed the possibility that she would be, since that would be preposterous and counterintuitive. That is, until his mother continued:

"And Christy, who does not need a babysitter, will be staying with friends."

Josh: "Why couldn't Alexa babysit me? She's only one year younger than this Jill person."

Mrs. Weistensteing: "Jill Wounderad is a special kind of babysitter. You'll see."

Josh resigned himself to his fate and didn't think anything more about it until he came home from school the next day, only to find that his parents had already left for their trip, and that his babysitter, who met him at the door, had already arrived.

Josh: "You must be Jill?"

Jill: "And you must be Josh. You're every bit as cute as your mother had said. Come in, Josh, I will be your babysitter until Sunday night, when your mother and father get back."

Josh, shrugging: "OK."

Jill: "Now Josh, you will find that I have different rules, and you will abide by those rules or receive a spanking. Your sister, Christy, will also assist me from time to time. Is that clear?"

Josh: "Yeah, I guess so."

Jill: "Good. Now for starters, you need to take off all your clothes and throw them in the trash."

Josh: "What? You can't be serious!"

Jill: "Not only am I serious, but you will soon be getting used to being naked around me and others. Your mother has agreed to this."

Josh: "I'm not getting naked in front of no one, you god damned weirdo."

Josh seldom swore, but he was beginning to feel the rebel among others. He seemed to sense where this was going, and he would have none of it.

Jill: "You will, and you will do so right this instant."

Josh: "I want to talk to my mom and dad."

Jill: "Very well, I'll dial the number on my cell-phone, and you can talk to them yourself."

True to her word, she did just that, and handed Josh the phone. His mother answered, and he explained what Jill had told him to do. He was shocked to hear his mother confirm the orders: "Now Josh, you are a boy, and a good looking boy at that. You have nothing on your body to hide. Girls have areas for bodily modesty, but boys, not so much. You will do as she ordered and you will do so immediately."

Josh: "Can I talk to dad?" When his father was on the other end, he only echoed his mother's sentiments: "What do you have to hide, son? You're only a boy. Now do it, and stop bothering us. We have a plane to catch." The line went dead, and Josh slowly and deliberately handed the phone back to his intrepid sixteen year old babysitter. He bowed his head, and began to undo his belt, when an overwhelming feeling of distress swept over him like a wave. He began to sob and say, "I can't do it...I can't, I tell you. Who the fuck do you think you are, anyways? What would the police say about this?"

Jill became incensed, and, glaring at him, reached down, yanked his belt from their belt hoops, and began to strip him. Being much bigger and stronger than him, she easily prevailed against his futile resistance. Once naked, he was taken over the knee and strapped with his own belt. The impacts created welts of his buttocks. Jill was merciless, and gave him about thirty whacks, including ten on his anus when she had him part his gluteal cheeks.

She then stood him up and began to explain the new terms to him.

End of part I

(The End)