Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 27

Coming of Age Sex Story: Chapter 27 - 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  

Dennis told me to write down my individual scores for the girls’ performance from 1-10 in the three categories of creativity, obedience, and willingness to be humiliated in public. It wasn’t an easy decision on my part. I was very critical of all three women and tried to be as objective as I could.

Lori had really amused me today in a lot of ways and she won the final contest. Doris had consistently performed, and she won the first contest.

Ultimately, I gave my highest score to Rachel because I was hoping she would get to spend an entire day with her father. She was often down on herself because she said that Doris or Lori usually won games.

I suppose, I wasn’t very objective after all.

Dennis waited until we got to a red light to jot down his scores for his wife and daughters. He told me he was quick with math and took my scores and averaged them with his.

“I wish Brad was here, he could perform a drum roll on your mother’s tits,” Dennis lamented.

I leaned into the back and began rapidly slapping her tits in drum roll fashion. Doris giggled. I tried to slap nice and hard the way that Brad probably would have.

“Lori with a score of 9.1!” he announced.

“Radical!” Lori seemed pleased.

“Rachel with a score of 8.7!”

“Of course,” Rachel sighed.

“Doris Wagner, coming in with a grand total of 9.7, you are the winner on our Shitcase showdown! Don Pardo tell her what she’s won,” he pointed at me.

“All of your wildest dreams will come true tomorrow!” I assured her.

“You may want to be careful what you promise,” Doris said she had some pretty wild dreams. “Are you going to take me out and let me be Candy for a day?”

“I was planning to drop you off down on Kelly Road!”

Kelly Road was notorious for hookers in Naples around that time. I didn’t know that. I never walked around there during the night. I asked what was so special about Kelly Road.

“That’s where all the hookers hang out,” Lori explained what was common knowledge in Naples at the time.

“My grandparents live in Moorehead Manor,” I said. That was a trailer park right off of Kelly Road.

“It’s called MORE HEAD Manor and you don’t see why it is full of prostitutes?” Rachel snickered.

I was a little incensed that they implied my grandparents would live near prostitutes. I used to assume those kind of women were degenerates and nymphomaniacs. However, considering the present company I was in, I thought I may have misjudged hookers.

It did explain a lot to me though. There was a single store where Kelly Road ends and connects to Rattlesnake Hammock Road. It was called Del’s. They sold everything from food, to live worms, to couches and televisions.

I used to hang out there and read magazines on the rack when I got bored at my grandparent’s house. My grandparents didn’t have much reading material and there were no libraries anywhere close by. The only thing for a boy that liked to read to do was to go stand in a store and read the magazines off the rack.

I remember meeting girls who were around my age walking into Del’s to buy cigarettes or even beer.

At the time, that was technically illegal but it wasn’t very well enforced in rural areas. People routinely sent their kids to the store to buy them cigarettes and beer. My parents never did, but I saw it happen frequently enough at Del’s to know it was a thing.

There was one girl in particular that I liked with very droopy boobs that always wore a tank top and no bra. Her tits pointed straight down, and you could see her nipples through her shirt. She was always really friendly toward me when she saw me at the store.

I wondered if that girl really was a prostitute? I wondered how much prostitutes really charged? I made up the number twenty-dollars because of something I saw on Blazing Saddles. I could have had sex if I had enough money and knew how to ask her to sell her body to me!

(I will be honest. I was probably too shy when I met her to have done more than stand there with my hands in my pockets and ogle her pointy nipples through her tube top).

I wasn’t sure if Doris was even serious about being a hooker.

They eventually renamed Kelly Road. It’s called Bayshore Drive now. Naples gentrified it and built-up exclusive communities out there. It was kind of the wild west back then though.

“How did everyone feel about the speech protocols?” Dennis added. He was pulling into Gulf Gate Plaza. Kelly Road coincidentally happened to the side road that connected to U.S. 41 right there.

“HATED IT!” overwhelmingly Doris, Rachel and Lori panned the idea of having rules. I wanted to defensively make the case that all I really did was make them call Men Sir and women Ma’am. I didn’t even make them do THAT much consistently.

Dennis laughed and said consistency was key. “Don’t make a rule that becomes more work for you to enforce than it is for the cunts to have to do. You should also have a goal in mind. Did you really want to teach them respect? Did you want to have an excuse to punish them by piling on unnecessary rules?”

“I wanted them to be more polite to everyone and see themselves as below everyone else.”

“Admirable,” Dennis nodded as if he hadn’t considered that reason before. I was flattered. Dennis told me that he’d like the girls to refer to him as the Judge or “Your Honor” at the judgments in the future. “I think it will make the judgment feel more official and distinguish me from the rest of the audience.”

“CUM ON HER,” Lori chortled a little over her play on words over how “Your Honor” sounded like “Your On Her”.

Her father chuckled as well. “Nice, and if you tell that joke at the judgment, it will be you that they cum on!”

“Don’t threaten me with a good time, Daddy!”

My vision for speech protocols had really been to introduce behavior like well-mannered Maids and Governesses. The girls would have to learn to say “Thank You” instead of “No problem!”. I was picturing teaching them painful lessons with the riding crops from “Miss Manners’ Guide to Excruciatingly Correct Behavior”.

However, I stuck with the easier explanation rather than clarifying my position. I normally just blurted my ideas out without thinking about how they would be received. I was evolving and maturing in ways I didn’t even realize at the time.

Doris could be crass and vulgar and she could be extremely cultured and well-mannered on a dime. I was hoping for elaborate rules that I could summarily punish the girls for breaking.

“Good, then we’ll definitely use those again,” Dennis announced to groans from the girls. “I wasn’t a fan, but the looks on your faces when you had to speak politely while having something shoved up your ass was priceless. You in particular Rachel,” Dennis said.

“Then why didn’t I win?” Rachel pouted.

“You came in very close,” Dennis assured her. She shrugged and sighed.

I began to think about the scores I gave everyone when she asked that question. I was good at math as well. I had scored the girls around 5-7 in most of the categories because I wanted to leave room for improvement. I assumed that 5 was the bar and that they had set that bar today to be exceeded in the future.

Even if Dennis gave his wife a 10 in all three categories, there was no way she could have scored a 9.5 unless I had given her a combined score of 9 or higher. My average for her was around 6. I didn’t want to say anything. I wondered if I was wrong but the math just didn’t add up. I ran the calculations on the other girls and none of it made sense to me.

If he ranked my scores of equal weight to the ones he gave them, then he had either made an error or he was intentionally lying. I decided not to confront Dennis. I was too shy and I didn’t want him to get angry with me if I was wrong.

“So, Mom gets to have you all day tomorrow, and we’ve got the White Gary Coleman to keep us company?” Lori snickered.

“I’ll be home in the morning for the yard sale,” he said.

The girls groaned again.

“You’ve got way too much shit. We’ve got to get rid of it! Things you don’t need anymore.”

“What about some of your tools, dear?” Doris smirked. The other girls smiled too.

“Those are necessary, and some of them are antiques,” Dennis couldn’t stop himself from laughing. “Point well taken, I’ll put some of my less useful things in the sale as well.”

He asked me if I had any plans for the girls tomorrow. I did not. “They scored well over a five. I can try to come up with activities based on their interests,” I suggested.

“You don’t even know our interests, Brian,” Rachel scoffed.

“Don’t undermine him when he babysits you tomorrow. If I find out that you did then I’ll box up everything you cunts own and we’ll have ANOTHER yard sale next week to get rid of it.”

“Yes Daddy,” they whined.

“It should really be not that much different than a normal Sunday when we have a family weekend,” Dennis assured his daughters.

“Except You, Mom, and Brad won’t be there,” Lori pointed out with a frown.

“If you had won, you would be gloating right now and telling Rachel me tough titty and so-sad, too-bad,” Doris reminded her daughter.

“Yeah, that’s IF I won, but I didn’t, so now I am bitching,” Lori said cutely.

Dennis had pulled into the McDonald’s drive-thru. I didn’t’ even realize it. He had three naked women in the back! How was he going to handle this? “20 nuggets, no sauce, a Big Mac, Large Fries, Large Coke with a lot of ice, and what do you normally have, Brian?” he ordered and then asked me what I wanted.

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