Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 21

Coming of Age Sex Story: Chapter 21 - 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  

Two girls on beach with funny looking bikini bottoms

“What are you talking about Brian? Some kind of game?” Rachel folded her arms in front of her body and looked at me skeptically. She was so beautiful, even when she looked at me like I was an imbecile.

I really didn’t have a plan in mind. I had some notes, a general idea and a boundless and perverted imagination.

“There will be winners and losers,” I admitted.

I wasn’t piquing their interest. Dennis wanted to get to the beach and the others did as well. It was hot out and we all needed suntan lotion. “You can tell us about your game on the way to the beach,” Dennis assured me. He told me to pick up something and carry it.

“We carried everything the last time we were at the beach, Dad. We also had to put it away,” I said.

Dennis was hauling a heavy cooler full of ice and beer. He stopped and looked down at me like I was speaking another language.

“You told me to call you Dad if I wanted, right?” I reminded him that after he decided I didn’t have to call him Mr. Wagner, he told me I could call him Dad because everyone did. Doris had said the same thing.

“Okay, here is the game,” I said. He sat down on the cooler under a palm tree by Gulf Shore Boulevard and listened as I outlined what I had in mind. His family gathered around and listened to me. I knew I didn’t have long to pitch the idea and I was taking a huge risk. If they thought it was dumb then I would probably lose the opportunity to pitch any other ideas again for a while.

I decided I simply had to make this idea work.

“It will be like judgment night,” I began. There was immediate laughter as the girl’s theorized I planned to hang them from the Naples Pier and freak out all of the tourists.

I told them that it would be like judgment in that we would be role-playing. Lori scoffed because she thought I was talking about dungeons and dragons. When I explained that role-playing was the ad-lib spontaneous acting that she was doing the night before. “You pretended you pissed in the whiskey because you knew that they’d want to force you to drink it.”

“Who says I was pretending?” she snickered.

“Anyway, you’ll each be responsible for coming up with your character. That includes you Dad,” I said.

Dennis was amused but impatient. He looked down at his wrist as if he were checking the time even though he didn’t wear a wrist watch.

“The last time we were here, you were lazy, ruthless, selfish, and bratty,” I explained to the girls.

“Did we fuck a lot of guys? Because I’d like to fuck a lot of guys this time,” Lori asked in a patronizing-get-to-the point way.

“Yes, you fucked so many and got so drunk that you left us here. Doris took off with the jeep and me and Dad were stuck.”

“I don’t even know how to drive a stick,” Doris chuckled.

“You drove my stick,” I offered back playfully. She blushed a little and smiled broadly. I got across to them that they had been ruthless bitches, and now it was payback time. “You agreed that we get to get even for your disgusting past behavior. You’ll do anything we tell you.”

“Okay, we’d have done that anyway, Brian.” Rachel shrugged and bent over at the waist. She stuck her ass out and her ass crack popped out of her bottoms. She knew a man was walking past and she blushed as she looked over her shoulder and picked up the boombox.

“Hold on, you will tell people like that guy that you agreed to this if he asks. You’ll also tell him that it is a competition.”

“Ooh, I like the sound of that,” Lori whistled. “What do we win? A trip to Bermuda?” she was being sarcastic.

“The winner gets to do family weekend all next week if she wants! You can be caged and hung all by yourself if you want!”

Dennis was the first to put the brakes on that idea, but I could tell that none of them were interested. “We have lives outside of family weekends, Brian. I know it looks like we indulge in constant orgies and gangbangs, but we’ve tried extending the weekends before and it doesn’t work.”

I didn’t want to mention that Brad didn’t follow that timeline. I assumed there was a logical reason they didn’t get to do it.

“Okay, that’s fair. What about this? Tomorrow, the winner gets to spend all day with Dad. They GET all of his attention and don’t have to share him with anybody.”

It felt strange to call Dennis “Dad” but I was getting used to it.

“What do the rest of us get to do on Sunday? Play titty-winks and shits and ladders?” Lori made up some names for dirty board games. I assumed they were board games. They might actually be real games with this family.

“No, I’ll keep an eye on you. You’ll be in the cage most of the day,” I was just making this up as I went, but Dennis didn’t stop me, so I kept talking. “If Dennis wants to hang you then I can be there to watch and make sure you don’t choke. You won’t intrude on the winner’s time. If you don’t like sitting in the cage gagged and bound all day and want to spend time one on one with your father, then you’ll do everything you can to win the game.”

“What is this game called?” Lori arched an eyebrow. She didn’t appear sold.

“The Cunts are Wrong,” I announced the name with the enthusiasm of Don Pardo announcing the real Price is Right. That was a very popular game show back then.

“Well Cunt, Cum on down and we’ll tell you what you have lost!” Dennis thought that was hilarious. I think his laughter helped sell it to the others.

“What do we do to win? Bid on a shit-case showdown and see who can be the biggest cunt without going over?” Lori laughed at her own perverted jokes. She was insanely clever with vulgar wordplay. It made me giggle. I had never heard a woman use vulgarity like her.

People were walking past us on their way to enjoy the beach. The Wagner family didn’t seem to care that people overheard them using vulgarity.

My mom would have lost her mind if she saw me laughing along and joking with them.

“Good idea, but WRONG!” I was smiling when I shouted and waved my arms. “Dad and I will be judges. We’ll grade you on your creativity, obedience, and willingness to be humiliated in public.”

“Ooh,” Doris looked like she had suddenly come on board. Rachel still seemed non-plussed over the entire idea.

“You will each be ranked from one to ten in all three areas, and then that score will be aggregated into a single ranking. There can be only one winner!”

“So, even if we score a perfect ten, then you are going to be our babysitter?” Lori scoffed. I liked her choice of words. I would be HER babysitter. I did not like that she had a fair point. I wanted the girls to compete, but I didn’t want to over-complicate things.

“Well now, it is your game, Son,” Dennis chose his words carefully and offered a helpful suggestion. “The score each cunt receives could determine their care and handling tomorrow. That way each cunt has the opportunity to win something.”

“Rice-A-Roni and turtle wax?” Lori quipped. That was a common parting gift for losing contestants of game shows back in those days.

“No, if you score a one, then you are in the doghouse. You need to score at least a five to have a day that probably wouldn’t be that far off from a typical Sunday family weekend.”

“If I score a ten and win then are you going to make all of my fantasies come true?” Doris pushed her body into Dennis’s chest and wrapped her arms around him.

“If you girls would like to spend one-on-one time with me, your mother will be the one to beat. I had carefully laid plans for Sunday for all of your fat asses. I already advertised the yard sale, so we are going to do that early in the morning. I am willing to set the rest of the discipline and training activities aside because I am intrigued. I will custom create a day just to tease and torture the shit out of the winner designed around your fantasies. It is going to be up to you cunts though. I won’t make you play the game.”

I was fascinated with the concept of “Discipline and Training Activities”. I didn’t know exactly what that meant, but I loved the sound of it. I was also flattered he would set aside his plans to accommodate my suggestion if the others wanted to play the game.

“We’re still going to be in a cage even if we score over a five and still don’t win?” Rachel asked.

“If you score higher than five, I’ll find ways to reward you,” I promised.

“No offense, Brian. You don’t even know what our interests are,” Rachel was a no out of the gate.

“You are Daddy’s favorite, so I don’t see why you are so worried about losing. I guess you are chicken,” Lori goaded her sister.

“I know what you are trying to do, Lori and it isn’t going to work,” Rachel insisted she wasn’t going to be easily manipulated.

“What? Get you to try a stupid game? I don’t care about that. You don’t either. What is the worst that would happen? We do a bunch of silly dares and look foolish at the beach? Gosh, that’s never happened before. I think you are just afraid that you’d lose and your little boyfriend would get to babysit you.”

“I am not afraid of losing and stop it, Lori! I just want to enjoy my day at the beach. I’ll obey whatever rules they come up with, but I am not going to play the game.”

“Then you would automatically lose and be in the dog house tomorrow,” Dennis informed her.

“So? It’s fun,” she added “Sometimes.”

“Well, I am intrigued. Can I make up a different name? I’ve always wanted to be called Candy.”

“No, you are Doris, in case anyone you know meets you here. You go by Candy because you are a whore and that is your stage name,” I countered. Keep in mind, that I didn’t know prostitution was really a thing anymore. My only frame of reference was Lili von Shtupp played by Madeline Kahn in Blazing Saddles. The whore with the heart of gold! She had a stage name.

Surprisingly, I didn’t have a crush on Lili t. My crush was the Governor’s side-piece, Miss Stein. If you go back and watch that movie, you’ll see she was hot like Ginger from Gilligan’s Island and wore a collar while showing off her cleavage during the entire movie.

In the 1980s, they used to let kids like me watch raunchy movies like that all the time.

“Oh, I charge money for sex? That is a new one for me! How much?” Doris asked the question like she was a brainless bimbo and down for anything.

In Blazing Saddles, one of my favorite lines is where Sheriff Taggert is talking to Hedley Lamarr (NOT HEDDY) while Hedley takes a bath. He says, “You use your tongue like a twenty dollar whore.”

Well, Doris definitely did that.

“Twenty dollars, but you can’t charge for sex this weekend. You’ve agreed that you were so rotten and inconsiderate the last time that we were at the beach that you’ll do whatever we tell you.”

“Oh,” Doris pouted a little. “I am being punished and can’t have sex?” she batted her pretty blue eyes.

“You are going to get to ad-lib your persona. If someone asks you for sex, you can come up to one of us and ask our permission to let you fuck them for twenty dollars.”

Doris’s response was a big grin. She was down to play.

“I am in like sin,” Lori was also willing to play!

“I’ll follow your rules, but I am not playing,” Rachel said. That was good enough for me.

I told them I would give them rules as we walked to the beach. “You’ll carry everything,” I insisted.

“No way, we can’t do this all-in-one trip by ourselves,” Lori whined.

“You will just have to make two trips! It’s part of the game that you agreed to do whatever we tell you since you were so rotten the last time,” I explained.

“Yeah, I know. I am getting into character,” Lori laughed raucously. I have to admit – she got me on that one. I think everyone understood the basic premise of the game at this point. However, there were still some details to work out.

Lori and Rachel carried the cooler, and Doris carried the umbrella, two chairs, and suntan lotion. We left the rest of the stuff in the jeep.

“I like this game already,” Dennis admitted breezily as we admired the girls struggling to carry the heavy stuff.

I gave them 10 rules. I felt like 10 rules seemed official. I could have made up 9 or 11 but it just felt right to have 10 rules.

1. All men are to be called Sir and all women are to be addressed as Ma’am except the three of them.

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