Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 52

Coming of Age Sex Story: Chapter 52 - 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 week I was hamstrung by the fact that Rachel and I did not share a schedule. I saw her once or twice throughout the day. She wore a bra when she left the house and changed out of it when she got to school.

I was surprised when Rachel told me more than a few girls did that. She had fat nipples that got hard easily, and I loved seeing them poke through her shirt. She also changed into a short denim skirt. She had a plentiful supply of trashy clothes that she was secretly borrowing from Lori.

I didn’t ask if Lori knew about our arrangement. I didn’t really know WHAT our arrangement actually was?

It mostly consisted of her finding me, begging to piss or shit and then showing me her stained panties were in fact wadded up if I demanded she pull them out from under her skirt.

I remember joking that they were “Wonder wear”.

“Wonder wear, sir?” she asked.

“Yeah, wonder where you shoved them last,” I chuckled over my own wordplay. I wouldn’ t have felt confident making that joke to a girl before this weekend, but I thought nothing of it. I wasn’t trying to make her laugh. I made myself laugh.

Rachel offered a stony expression and a deadpan response. That joke might have killed with her sister though.

That week I kept things very discreet. I had little choice because my time with Rachel was very limited. I rode a bus and there was no time before or after school.

I saw Brad around school. If he knew about what was going on with me and his sister, he didn’t say anything about it. He was warm and gregarious and made it a point to say hello to me. It felt really strange being acknowledged by a popular kid in school.

People noticed and looked at me as if they couldn’t believe it. Brad wasn’t embarrassed to walk up and slap me hard on the back playfully, and then put his arm around me.

I noticed that as a result of that I was experiencing a slight bump in popularity. I wouldn’t say that I was the kid everybody new at this point. I was just a little less of a background character that nobody noticed.

At night, I beat off constantly. That was nothing new for me. I was a chronic masturbator. However, now I had some real spank material to jerk off too. I didn’t look at my Playboy magazines. I didn’t need them.

I have to admit, I felt a little like I was cheating on Ruth Guerri (my go-to centerfold) when I wanted to pop a nut. I was not paying any attention to her any longer. All I could do was reflect on the weekend with the Wagners. Rachel, Lori and Doris were hot in their own ways. The vivacious slightly older former cheerleader, the mature sexy woman with no boundaries, and Rachel the quiet and shy sexpot that secretly wanted to be punished.

I should have opened my own sperm bank because I would have made a fortune with what felt like gallons of cum that I dropped down the sink back then.

My nights were consumed dreaming about the past weekend and glowing.

Judith had always talked to me in French class. She was very polite, and nothing changed about that. I remember one day her asking me what my favorite authors were. I didn’t think anything of it at the time. I responded rather tongue in cheek that I prefer Alfred E. Neuman of Mad Magazine. I told her seriously I was a fan of Ray Bradbury and DC Fontana.”

“At least, you like one female author,” she said. I didn’t know that DC Fontana was a female. That didn’t make any difference to me, but that was news to me.

“What about Anne Rice or John Norman?” she asked.

I didn’t know who Anne Rice was and the only thing I knew John Norman wrote was Tarzan stories. I told her that they didn’t grab me.

“Edgar Rice Burroughs wrote Tarzan,” Judith corrected me politely. She reminded me at times of a font of esoteric trivia.

I shrugged. I had no interest in any of those authors and I assumed perhaps my mind flicked to Tarzan simply because the name Rice was shared between two authors.

Judith explained that Anne Rice wrote under the name “A.N. Roquelaure” as if that would perhaps be familiar to me but it wasn’t.

“Pity,” she seemed disappointed but not angry that I had no interest in discussing their novels. “Will we be seeing you at Rocky Horror again?” she changed the subject.

“I am kind of surprised you go to that,” I said.

“Why?” she genuinely seemed puzzled.

“Well, it can be a little bit naughty,” I said with understatement.

Judith dressed in mostly black and tended to wear two identical tennis shoes of different colors. She had big boobs, but she wore such a confining outfit that you almost didn’t notice how big they were. Today, they shook a little when she chuckled and I noticed!

I think she saw that.

“It does get a little ribald on stage, but if you think that is provocative, you should see what happens backstage,” was all she said by way of explanation. Class was beginning and I did not get to ask her for more details.

I assumed what was wild to Judith would be quite tame compared to the weekend I had, anyway. Judith struck me as one of the most non-sexual people I had ever met. She liked geeky and science things, but she seemed different than boys who liked those things.

I didn’t know what Steampunk or Victorian fashion was at the time, but Judith had a taste for those things and while it might have fascinated me – It wasn’t something I was particularly interested in. I liked Light Sabers and Warp Nacelles.

I steered very clear of her brother over that week. I could still feel the punch that landed on my jaw when I shut my eyes. I think he knew that he intimidated me, and he seemed to like that.

I suppose one unintended consequence of rising popularity was that I used to blend into the background. When Brad started talking to me, that got me noticed. That also meant people bullies like Willy Scott would find me.

I chalked up the fact that I was getting noticed to the two or three times that Brad acknowledged me in front of others at school. I didn’t realize it at the time, but I had grown in maturity and confidence and that was coming across as well.

I walked right up to David Quiles and had a conversation with him over lunch. He was the boy that played “Rocky” in the RHPS show. I knew him as an acquaintance and what I mean by that is we sometimes sat near each other in the computer lab during lunch.

The computer teacher didn’t mind that nerdy boys like me brought our own disks from home and put them into the Apple IIe computers to play video games over lunch. It wasn’t officially sanctioned but we all did it.

We traded games like Zork and Temple of Apshai, and then saved our progress right onto the disks. No hard drives for us back then. When I say trade, I also mean that we gave each other copies of the disk. The only limit was the number of blank disks you had available to you and the copy protection that came with it. That usually consisted of a paper wheel or some codebook that came along with it.

“Hey David, do you want to play my Ultima?” I asked. I knew that he did because he often stared at it. I actually owned a copy. My mom ordered it from California and I was so overjoyed when it arrived. I still hadn’t even beaten it yet.

“Yeah, do you have a cracked version of it?”

“I can let you borrow it,” I shrugged. No one would do that for a passing acquaintance. There was a chance they would ruin your paper copy protection wheel or worse.

David seemed a little confused by my offer. He obviously thought I might expect something in return.

“Dude, I am not gay like Brad if that is what you are suggesting,” David’s response really shocked me.

The word gay had very shameful connotations back then. I told David to keep it down. I was offended that he might think I was gay. I was just being nice.

“Everyone at Rocky knows Brad is a flamer,” David said. I assumed that he had seen me with Brad and assumed that was why Brad was so nice to me.

“I am not gay with Brad,” I whispered angrily.

“Of course not, you aren’t his type. He likes manly men,” David laughed.

“Like you?” I was offended and I meant that as an insult.

“No dude, how do you think I got the part of Rocky?” David wasn’t insulted at all and he didn’t’ keep his voice down even though there were a dozen other students all using computers in the room at the time. They seemed annoyed over the interruption because they were all focused on playing their own game.

“I dunno.”

“No one could follow Brad as Rocky. He is shredded. They picked me as a joke,” David seemed fine with that. He was scrawny and I hadn’t understood why he was cast in the past at the time. David explained that they didn’t even try to replace him when he stopped coming to the show. “The ONLY person who could follow that act is someone who does it for comedic affect. I meant to ask, please don’t tell anyone I run around in my underwear,” he grabbed my arm and implored me to keep his secret.

“Why would I do that?”

“I don’t know, to be a dick?” David suggested.

“I am not a dick,” I clarified.

“I dunno, man. You were like sitting with Lori Wagner at the show. She and Brad are like Rocky Royalty.”

I had never heard that term before. Rocky Royalty did seem like it applied to them.

“You could have like introduced me or something,” David complained.

“You could just go right up and talk to her,” I shrugged.

“Me? Just walk up and talk to LORI Wagner? I mean, I’ve spoken to Brad before, but if he shows up then everyone is going to want him to play the part. What exactly am I supposed to do? Walk up to Lori Wagner and just introduce myself like some kind of asshole?”

“No, not like some kind of asshole. Just introduce yourself,” I advised.

David obviously placed Lori REALLY high on a pedestal. He didn’t argue with me, but I think he assumed that I just told him the secret to getting rich was getting a million dollars and investing wisely. It was basically impossible for most people.

“How did you get to meet her anyway?” David changed the subject.

“I was babysitting her and her sister,” I smirked with pride. David clearly didn’t believe me.

“She has a sister? Is she hot like Lori?”

“Yeah, she was sitting right next to her. She goes to our school,” I said.

“What? LORI WAGNER’S SISTER GOES TO OUR SCHOOL?” David found that incredulous. I might as well have told him that a celebrity like Eddie Van Halen’s sister went to our school. He didn’t believe it.

“Yeah, she usually comes to find me right after lunch and I haven’t seen her today. Come with me to my locker after class and I’ll introduce you.”

“I don’t like to be late for class,” David insisted. I recognized that impulse to follow rules immediately. This week I had been late twice. The first time was an accident, and the second time was just to see if I got in trouble. The teacher gave me a stern look and didn’t do anything when I sat down.

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