Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 54

Coming of Age Sex Story: Chapter 54 - 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  

That day I told David to go outside during 5th period and meet Rachel behind the dumpster. I didn’t show up, but she’d be waiting for him. He was reluctant to skip class. I think he was glad he did, because after that he never doubted me again.

I reintroduced Rachel to David the following day in the hallway after computer class.

“Piss-face, I think you met David”

“Piss face?” David grinned.

“Yeah, he calls me whatever he likes,” Rachel admitted coyly.

“Why is that?” I asked.

“Because I am a piss-face, Sir,” she admitted.

“Did you enjoy sucking David’s dick?” I asked.

“Yes Sir, he has a nice cock, thank you David,” she licked her lips.

David adjusted his pants and looked around nervously. There was loud music playing in the hallway and we were talking softly that no one was probably listening to us.

“Why do you do what he tells you?” David seemed confused. I wish he hadn’t asked that question. I had this whole thing in mind where I was going to make Rachel sing her “Milk, Milk, Lemonade” song for us before letting her rush off to the bathroom.

“I guess, I just like being told what to do,” Rachel replied introspectively.

“Wrong answer,” I grabbed her nose and twisted playfully. “You ENJOY being a brat and a cunt, and you NEED discipline and structure. So, you crave consequences for your miserable behavior.”

“Maybe,” Rachel replied coyly. I might have let it drop if she had just agreed with me, but I felt I had to make a point.

“There is NO maybe about it. Bend over and grab your knees, show him your tail,” I insisted. Rachel was very hesitant, but David and I blocked off most people from being able to see. It was still awkward and when she bent over, I saw the tuft of a purple pair of panties hanging out of her asshole like a rag sticking out of a gas can.

“Are those your panties?” David was flummoxed. I let Rachel stand up quickly so as not to cause a scene.

“Well, they aren’t mine. I don’t want to ruin my own. Those are Lori’s panties,” she said. David’s eyes grew wide at the mention of Lori. It was obvious he had a huge crush on her.

“Why do you have them stuffed up your shitter?” I asked.

“Because you told me to do it, Sir” Rachel provided a logical answer, but it wasn’t the one I wanted to hear.

“Technically, true but you have lost the right to wear panties around your waist. You can only stuff them up that huge, gaping fart-hole of yours like a tail to remind you that you are to behave.”

Rachel sighed as if she didn’t fully agree and then nodded yes. She didn’t like “speech protocol roleplay” as she called it. I didn’t know that there was a whole kink focused on protocols and forms of address – I just knew that I DID enjoy these little talks and I felt they reinforced what lesson I intended.

Rachel may have seen the games as a series of distractions and perverse diversions, but I wanted them to mean something – to provide some value in the end. I enjoyed the feeling of punishing the girls for their behavior at the mall, almost like a therapy or an educational course using applied pain and discipline.

“Will Lori do what you tell her at Rocky?” David asked.

“She did last time,” I said.

“Nuh uh, she was out there gabbing with everyone.”

“I’ll let both of them suck your dick and you can tell me who is the better cock sucker.”

“You would be the king if you could do that,” he said.

After he left, Rachel apologized and told me that she was very nervous around him. “You aren’t going to be given that same opportunity when we do Rocky Horror. Did you ask your sister about it?”

“Yes, of course. She is up for anything. We have to ask Daddy to let us go on the next family weekend and it’s in two weeks or next month.”

I patted her ass and gave her permission to take a shit. I wasn’t sure how I would get my parents to let me come over that Saturday night. I exuded confidence though and assured her that it would be two weekends from now.

That next afternoon in French class I asked Judith how she gets her parents to let her participate in the cast of Rocky Horror Picture Show.
“Well, that’s easy for me, my Dad is the director,” she said plainly.

“Your DAD is the director?” I was aghast. Judith was so “normal”, and I assumed anyone who “directed” Rocky Horror was probably some kind of freaky pervert.

“Why does that surprise you? Someone has to direct the chaos,” Judith smiled. I admired her for being such a bookworm and nerd. I had never met a girl who was either of those things before and I really don’t know how to regard Judith.

“What does your mom think about your dad being there?” I blushed just thinking about my mother’s reaction to my father being around the Rocky Horror cast. The cast wore lingerie and flashed the audience at the end. I was sitting so far away that I had barely seen any nipple, but I was positive at least two of the cast members were women.

“She’s the manager,” Judith smiled proudly.

“What? I thought Lady Viking was the manager?”

“That is her nom de plume,” Judith confirmed before adding that to the rest of the world she may be Valerie Scott or Lady Viking, but to Judith she was simply “Mom”.

I was having a hard time processing what I had just been told.

“They don’t let you stay for the ENTIRE show do they?” I asked incredulously.

“They kind of have to since I am in the final scene,” Judith regarded me as if I were being silly now.

“You were just in the opening credits, weren’t you?” I asked.

“Yes, I play Lips in the opening credits. Then I change clothes and transform into Columbia! Didn’t you see me up on stage? I saw you when we did the time warp!”

“Yeah, the girl on stage had red hair!”

“A wig!” Judith held a dramatic pose like Magenta after she performed her tap dance number and exclaimed “Acting!”

“But.”

“Are you freaking out because you saw my boobs when I was on stage?”

I was, but I didn’t want to say that. “Those were fake boobs, right?”

“I can assure you, these are my own milkers,” Judith appeared offended, as she caressed the under part of her bosom. She was wearing a very baggy shirt. The girl I had seen on stage had huge knockers. Judith was a big girl, but I didn’t think she had huge tits.

“I didn’t mean to offend. I am just surprised that your parents permit you to do that?”

“My parents are very bohemian. My father was the one who thought up the gag where Rocky pulls down his bustier and flashes the others, and then we all start flashing each other until we start to angrily flash the audience. Honestly, I did not take you for a prude,” Judith snickered.

I wanted to have a longer conversation about this, but class was beginning. After class, I approached Judith again and assured her that I was no prude.

“I was simply teasing you,” Judith reminded me of Charlotte, the Spider from Charlotte’s web when she talked to me like this. She had a very calm demeanor that wasn’t exactly patronizing but it made me feel like I was a wet behind the ears pig that still knew nothing about the world – which in truth, I kind of was.

“You sure like teasing Rachel Wagner and from what I gather, you’ve seen more than just her boobs.”

“How would you know that?”

Judith regarded me now as if I were insulting her intelligence. “You’ve been giving her little instructions and making her shake her ass and tits around school. I am one of her classes and I watched her sit there with her legs apart like a bimbo. The teacher had a total view of her privates, and boys kept coming up and sharpening their pencil and then dropping it to take a closer look. I’ll give her credit- she never flinched or let on that she noticed.”

I was happy to hear that.

“From what I gather, Rachel isn’t permitted to wear a bra – at least not at school. She has other clothing restrictions. When she bends over, I see a little flash of her undies pop out like a tail. I even understand you had her hand out dirty little cards asking boys to punish her. I never knew you were a misogynist.”

I didn’t consider myself a misogynist and I didn’t want Judith to think I was some kind of woman-hating asshole. I assured her that I wasn’t one and that anything a man could do a woman can do as well.

“Anything a man can do, women can come behind them and fix,” Judith corrected wryly and excused herself apologetically. “I didn’t mean to strike a nerve. It just seemed that you spent all day bossing and teasing those girls at the beach, the mall, and now Rachel at school. If you are embarrassed, then why do it out in public?”

I had assumed that Judith never picked up on what we were doing at the beach or the mall. She had been there that day. She told me that it was fairly obvious that I was the puppet master pulling the strings. “You engineered a catfight between them. I’ve seen real catfights at Rocky. Those girls would have been wanting to pull each other’s heads off if they were really angry. It was all for show. If this is something that you are ashamed of – why do it in public?”

“I am not ashamed,” I corrected and added that I was just being discrete.

“You scrawled some dirty words on their buttocks and made them walk around the mall showing everybody. They even danced with the keyboard player and probably gave him a hand job. It was hilarious, I watched you all afternoon from a distance.”

“Did your brother see?”

“William has his head up his ass, but yes, I think everyone saw the girl’s famously pull each other’s clothes off in the food court. It was quite a day,” she said. We were walking together down the hall, although I wasn’t sure where we were headed. “I have to admit that I was quite jealous,” she said.

“You were?”

“Yes, to have all of that attention. Why do you think I perform on stage? I get a similar rush. I am a bit of an adrenalin junkie,” she said.

I had to smile because Lori had told me the same thing. I assumed it meant something vastly different in the context that Judith was using it. As open minded as she was, I doubted she was ready for the things that the Wagners did.

“Why do you laugh?”

“I just didn’t expect this reaction from you,” I admitted. We were definitely headed the wrong direction for the class that I needed to attend but I didn’t care.

“I do not know whether to be insulted that you thought I was a stick in the mud who wouldn’t understand, or to find it charming,” she admitted. “Frankly, I do not know the nature of your relationship with Rachel. I’ve only seen the manifestation when you flaunt it. Is she your submissive?”

“Yes, she does what I tell her,” I said.

“Do you mind me asking, are you polyamorous with others or is this strictly monogamous?”

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