Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 55

Coming of Age Sex Story: Chapter 55 - Join Brian back in 1984 in sunny South Florida. He's obsessed with his babysitter Rachel. She's cute, quirky, big glasses, and a little older than him. She's babysitting him for the entire weekend. He's going to discover that Rachel Wagner and her family live a very different lifestyle than anything he's ever seen before and it is going to blow his mind.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   mt/Fa   Teenagers   Consensual   School   Slut Wife   Incest   BDSM   DomSub   MaleDom   Humiliation   Light Bond   Spanking   Gang Bang   Polygamy/Polyamory   Interracial   Anal Sex   Enema   Exhibitionism   First   Facial   Fisting   Food   Oral Sex   Sex Toys   Squirting   Tit-Fucking   Water Sports   Babysitter   Public Sex   Nudism   Illustrated  

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I told Judith to tell me a little about the book that inspired so much of her desires. In the novel, Beauty was awakened from her hundred-year sleep by the prince, not with a kiss, but through copulation, initiating her into a Satyricon-like world of sexual adventures. After stripping her naked he took her to his kingdom, ruled by his mother Queen Eleanor, where Beauty is trained as a slave and a plaything.

The rest of the naked slaves, dozens of them, in the Queen’s castle are princes and princesses sent by their royal parents from the surrounding kingdoms as tributes. In this castle they spend several years learning to become obedient and submissive sexual property, accepting being spanked and forced to have sex with nobles and slaves of both sexes, being publicly displayed and humiliated, and crawling around on their hands and knees like animals until they return to their own lands “being enhanced in wisdom.

My eyes widened. This story spoke to the very heart of what I wanted to get into with Rachel. I wanted to “enhance her in wisdom” through the application of pain – I just didn’t see it in such grandiose fairy tale terms.

Judith refused to spoil the book for me by telling me any more of the plot. I made a mental note (and did) read the book cover to cover many times. I highly recommend it.

“You understand that you will need to get naked for me on command?” I felt a little more emboldened now that Judith had laid out her inspiration.

“I certainly hope so,” she said. “Shall I do so now, Sir?”

“Yes,” I said. What boy my age would have refused?

She crossed the room and locked her door. Then she began to undress. “I did not tell you to lock the door.”

“William has a tendency to fly into the room unannounced, Sir,” Judith offered with a bemused expression.

I grabbed a hairbrush from her desk and spanked her bottom with it. “I will not tolerate you dictating terms to me. I just informed you that I did not instruct you to lock your door. If William walks in then what will he see?”

“A naked girl?”

“Wrong,” I spanked her ass over her jeans

“A naked piggy,” I reminded her that she asked for this and then told her that I did not want a striptease and she was to get right to undressing.

Judith blushed and couldn’t look at me. I liked making her feel awkward. She unlocked the door and began to step out of her clothes.

“Sluts remove their bottoms first, tops second, everything else last. Give men something to look at,” I said that was a rule.

“I do not own many short skirts. Will I be required to wear those at school, Sir?”

“Yes,” I said.

“I understand that I am not permitted to wear a bra any longer, and while I have very heavy breasts, I am willing to agree to that. However, I have an extensive collection of corsets. Would you be amenable to those as long as the nipples are exposed?”

I soon understood why Judith wore baggy clothes to school. Once she removed her bottoms, I saw she had a wonderfully fat ass, and a very hairy vagina. It wasn’t all that remarkable. However, when she took off her top, her tits looked awesome.

They didn’t just straight out like Rachel. She was wearing a tight leather corset that she had laced up so that she had to suck in her stomach. It forced her tits out and up. When she removed it, they hung down heavy and pendulous.

She showed me a closet full of corsets and told me that she had made them herself. “I am quite the seamstress,” she preened.

“I will very likely not permit you to wear a corset or bra, unless that is all you have on, if you sign our contract. Is that a deal breaker?”

“What about at home? May I wear what I normally do in the common areas of the house?”

“That depends,” I said in a witty reply and added “Is what you normally wear at home tits out, buns out?”

“No sir, it’s what you saw me in today,” she said.

“Then no,” I said.

Judith got quiet and seemed to regard my offer with some thought. I suspected she would tell me that this was already too much to ask. It definitely seemed to me that I might have overstepped with this latest rule. It was a lot to ask her to run around in front of her family in these outfits.

Rachel could do whatever she wanted at home. I didn’t make rules for her at her own house except she had to call me and masturbate at times.

“Having doubts?” I asked.

“I would still be permitted to participate in the cast of Rocky, and that includes wearing costumes even if they include panties, corsets and bras, sir?”

“Yes.”

“Then no, no doubts.”

“Okay, you are also forbidden to play with yourself. That includes tits, asshole, and pussy without permission.”

“Clarify,” Judith said as she stood casually before me in the nude. “Does that mean strictly dildos, or does that rule extend to everything from a casual wipe of a tissue and spreading my legs under the faucet in the bathtub?”

That was a tricky question. I had meant not masturbating with fingers, but Judith had a lot of questions that gave me pause. “Anything that would provide erotic stimulation.”

“What about reading, Sir?”

“Reading is fine,” I said.

“That would be fine. Stand up straight, legs apart, tits out, and chin up,” I put her in a more rigid position. Judith’s tits hung down on her chest so there was no “tits out” but she managed the position rather well despite the heaviness of her boobs.

I encouraged her to throw more questions at me while I adjusted her posture. Judith had a tendency to slouch, and I found myself constantly correcting her. Her skin was incredibly soft and smooth as well. I enjoyed touching her creamy, milk-white body.

“You mentioned that we would be polyamorous. I assume that means other sexual partners, but no others for me then?”

“You will fuck, suck or even kiss whoever I tell you to do, as my personal whore. However, you will NEVER be permitted to make the offer yourself?”

“Clarify,” Judith had a tendency to start off a follow up question with that word before asking the question. I kind of liked it when she did that. It added a level of formality to our discussion. “You could tell me to offer my mouth to someone. In that sense, I’d still make an OFFER for sex to someone?”

I thought she was being pedantic, but I appreciated the clarification. I told her that she would not spread, lick, suck, or touch anyone else or herself without my permission. “How often do you play with yourself now?”

“Daily and nightly, Sir” she admitted without shame or hesitation. It was obvious she liked that.

“How often did you have sex with other partners?” I asked.

“You mean beside the gang bang in the cast dressing room after Rocky?” she teased. She clarified that it was a joke when she saw that I took it seriously. “I’ve had fuck buddies, but they have turned out to be rather disappointing. David Quiles and I had an understanding but he can be rather dull.”

“Will it bother you if I never allow you to fuck him again?”

“Not at all, it would be a rather convenient excuse, Sir” she said smartly.

“Would it bother you if I told you to wait for him outside behind the cafeteria dumpster and suck his cock?”

“Is that where you have been going during French class?” Judith seemed pleased that a mystery had been resolved. “No, Sir. It will not bother me if you tell me to offer my mouth for his use – but I would not like to be made to miss class or have my academics suffer in anyway.”

I nodded in agreement.

“May I ask, how many sexual partners am I likely to have in a week, Sir?” Judith seemed nervous, almost apprehensive.

I hadn’t shared Rachel with many people. “One or two, at a minimum,” I said as I tested the waters. I meant different people each time. That’s why I was surprised when Judith’s response was a simple shrug and an acknowledgement.

“How many would you prefer?”

“This is about you defining the boundaries and expectations and not me telling you, Sir.”

“I thought you did not like games,” I countered. “You clearly thought about this before you made the offer. How many did Beauty have?”

“Oh countless, but I know that is a fairy tale and I cannot hope to have what she had?”

“Why not?”

“Well for one, she was trained in the stables, to perform as a beast of burden and pull carts like an animal, to crawl around for the amusement of her master and the stable boy.”

“Is that something you would like?” I probed. It seemed outlandish but not too far out compared to what I had seen.

“I really don’t believe you could visualize it unless you’ve read the books,” Judith warned me. I grabbed a tuft of her pubic hair and yanked hard. I slapped her pussy and told her that it would be shaved bald by tomorrow.

“Do not presume to know what I do know, and I do not know, Piggy. You are a pig, and you will be trained as such. I asked if that is what you want?”

“I mean, I WANT an ice cream sundae and a good book to curl up with. I don’t know if want is the proper word for this,” Judith regained her composure after the hard slap on her pussy rather quickly.

“Do you want to be ENHANCED IN WISDOM, by the proper application of discipline, through training in humility, patience and obedience?”

“Yes, God yes,” Judith nearly pounced on me when I said that.

“Then you will be pony trained,” I said.

“How often?” she asked excitedly and clarified she was looking for an average.

“I would need to find a place that we could do so in privacy,” I said. I hadn’t thought this out and I wasn’t ready to make any commitments.

This time Judith was not disappointed. Instead, she eagerly made a suggestion. “There are some woods near the school. I’ve gone out there by myself. If you do not mind some palmetto bugs and mosquitoes, it would be an ideal place, Master.”

We went from Sir to Master. It felt really good to hear her call me that.

“How often could you be trained in this manner?”

“Every day after school before dinner, and possibly on weekends. I have Rocky on Saturday nights and the cast must be there at 8pm.”

“Have you ever been fucked in the ass?” I changed the subject. I was getting excited, and this sounded a little too fantastic for me.

“No, I assumed most boys find it yucky,” Judith admitted. Her eyes lit up and she asked if she could show me her toys.

I gave her permission, and she opened a drawer. She had a pink massager that was shaped like a penis and another flange like device that was much smaller designed to go into her butthole. She explained that she made it with her father’s bottle opener and showed me how on the end it could still open bottle caps.

“Shove this up your ass,” I said as I handed it back to her.

“Do I get to warm up, Sir?” Judith’s reluctance made me angry at first. I was used to the Wagners, and they were well practiced with anal play. They didn’t need a lot of warm up. I parted Judith’s big ass cheeks and admired the dimpled little purple knot between her cheeks. Then I spit on it and plugged her asshole with it.

“You’ll shove a pair of panties up your asshole every day at school and leave a bit of a tail hanging out.”

“I’ve seen Rachel, do that Sir, would you consider an alternative?”

“Yes,” I said.

I could wear my plug and sew a 3x5 favor to the base. Judith explained that she was a fan of the Middle Ages and that in days of old, Ladies would grant knights a favor to wear into battle on their behalf.

“You can show me tomorrow,” I said. “You must ask my permission to shit or piss at school and that is the only time you can take it out.”

Judith seemed a little reluctant to agree to that. I did not know that most women weren’t practiced enough to keep something in their assholes for as the Wagners did. “What about at home?”

“You don’t have to wear it here” I said and added that I might punish her and make her do it anyway.

“Yes, but how do I obtain permission to use the restroom?”

“You do not use the restroom. You shit and piss like an animal from now on, and you will do that during pony training or at school,” I said. I realized from her expression and from my own common sense that I may have been a little hasty on that decision.

I wasn’t ready to just back down though.

“I don’t want you to take the privilege of using the bathroom like a person for granted. You are a pig, and you have to accept that. If you can just use the bathroom before school, then you won’t need to beg me later and your education will come much more slowly,” I offered.

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