Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 37

Coming of Age Sex Story: Chapter 37 - 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  

It took Lori a good ten minutes to waddle-run all the way around her house. It was hilarious watching her bare tits jiggling as she tried to hustle with her panties around her knees.

I permitted her to pull up her panties and put her shirt back on before she got back to the driveway. We already had three or four more customers milling around when she got back.

“That was hilarious,” Lori laughed. She dried her eyes. “I can’t say that I have ever been told to do a lap of queefing before!” she seemed totally amused. It wasn’t’ quite the reaction I expected. I thought she’d tell me that I had gone a bit too far.

“Now those guys are going to think you are a chronic masturbator,” I admitted.

“They already think all kinds of shit about me now. No one is going to believe them if they tell the story to their buddies, and even if they do, who gives a shit? I cried so hard from laughing after it was all over that I washed some of your jizz off of my face. Did you have fun?”

“Yeah,” I said.

“Good,” she adjusted herself and adjusted her shirt and panties. I was elated that I had chosen wisely.

She rubbed her buttocks and told me that I was getting better at spanking. “You still hit like a sissy, but you’ve got better technique.”

“Save your hand and use a paddle,” Doris was standing at the table as she offered me the sage advice. People were close by, and they could probably have overheard the conversation. The Wagners didn’t seem to care all that much.

“Didn’t you used to date that boy?” Dennis asked.

“Don’t remind me,” Lori put her finger in her mouth and began to suck it absent mindedly. “I think he was dating a friend of mine. I decided to flirt with him and take him away. I don’t remember why I gave him a second date. I was probably bored,” she shrugged.

I was shocked she was so flippant about relationships but at the same time, it did sound a lot like Lori. Why would she take a good friend’s boyfriend? I didn’t understand that. It seemed like a mean thing to do.

“When we’ve got a lot of customers like this, don’t spank the girls like that in the yard. Take them in the garage,” Dennis explained. He told me to check on Rachel. He handed me a thin wooden rod and implied I should use it on her.

“I know,” I said that I had common sense.

“What you made Lori do was a little more than I would have made her normally do,” he told me under his breath. “I am not mad, and she had fun. We’ve got to live here though and deal with these people outside of family weekend.”

He told me to go check on Rachel again. He handed me a thin wooden dowel that could be used to point to things on a chalk board. It was also a perfect rod to hit someone with.

Rachel was groaning and lamenting her situation when I walked into the garage. Rachel was still tied up to the wooden chair in the garage. It was damp and musty in there. She had sweat dripping down between her sobbing tits. She was truly sulking when I came in.

“Did you come to gloat?”

“No, I was just checking on you,” I said.

“Well, I am still naked, and I am sitting on a joy-buzzer. Go ahead and flick the switch if you want. You know you want to play ‘humiliate the babysitter’.”

I didn’t think of Rachel as my babysitter any longer. It was nice to be reminded that I was the one that had authority over her now though.

She wasn’t asking me because she seemed to enjoy it or was excited by it. She wasn’t even daring me to do it like there would be consequences. She seemed to just be wallowing in her own suffering.

I DID want to flick the switch. I did want to hit her with the rod. I didn’t want to do it like this. She seemed so helpless and vulnerable. That normally turned me on. Rachel often wore a frown or seemed unimpressed. She wasn’t happy-go-lucky or bright and mischievous like Lori. She was more pragmatic and often seemed rather non-plussed about her participation in family weekends.

I was reminded of when she was locking her feet in a wooden pillory. She told me to hurry up and fuck her so that others could have a turn. She was not happy, but she seemed content with her role as a party favor before participating in judgment. I wasn’t so sure now.

“If you don’t like doing this, you can always tell your father you want to stop,” I said.

“You don’t understand,” she rolled her eyes. “Just hit me or flip the switch or stick a broom up my ass. Do anything you want to me but don’t look at me with those puppy dog eyes and talk to me, please.”

I had puppy dog eyes? That seemed like a plus! I was thrilled to hear that she thought that I did. I wasn’t so thrilled that she didn’t want to talk to me. I left the garage and returned to her father without doing anything to her.

I walked out of the garage feeling dejected. Doris and Lori were chatting up potential customers. Dennis was surprised that I returned so early. “Getting bored of Rachel?”

“No, she doesn’t really like being tied up,” I admitted.

“Do you know why people like sad songs?”

“No,” I didn’t know what that had to do with anything.

“Sad songs make you feel sad, right? They can make you feel lonely or think about a lost love.”

“Yeah,” I agreed.

“Why do you think anybody would ever listen to a song that made them feel sad or melancholy?”

I had never thought about it. I tended to like faster songs and I wasn’t into sentimental music. I remembered that Rachel did like Barry Manilow. He was the king of sappy music. He had songs with titles like “Can’t cry without you” and “I write the songs that make the whole world cry.”

I knew there was a connection, but I didn’t understand what point Dennis was making. He put his hand on my shoulders to let me know that he understood my confusion. I felt lucky that he was giving me some sage fatherly advice and I really needed to listen to what he had to say. His advice truly felt like a gift and I was flattered Dennis was taking the time to explain how things worked to me. I knew he didn’t do that for just anybody.

“It’s good to feel happy. If you were happy all of the time though, how would you know it? You’ve got to have the lows to make you appreciate the highs,” he explained. That made sense but I didn’t quite see what that had to do with his daughter feeling miserable in the garage. She didn’t seem like she was going to feel happy just because he untied her.

“One of my favorite candies is a sweet and sour. You’ve got sweet and you’ve got sour all mixed together. You get different sensations,” he started to explain.

Lori couldn’t help being a nosy goose. She told us that her favorite candy was a spicy cinnamon red-hot. She had only overheard the tail end of our conversation and assumed we were talking about candy.

“There you go, and when your tongue is burning it releases endorphins which trigger a happy chemical in your brain, but to get there you have to experience a little pain.”

I didn’t like hot candy. I think he could tell from the look on my face I still didn’t get it. “Some people crave salty, or sweet things and that releases endorphin. These sluts crave danger, humiliation and pain,” he said. He lifted his daughter’s shirt in the back and exposed her ass crack. He patted her butt and sent her away to talk to customers and pretend she didn’t notice.

“Even if you love salty potato chips, you can’t eat them all of the time. You’d get sick of them and wouldn’t want them anymore.”

“So, Rachel is just tired of being tied up?” I asked.

“That could be, but I know her a lot better than you,” Dennis went over to Doris and lifted her shirt as well. He felt her up and then put the shirt back down. No one at the garage sale seemed to notice or if they did they didn’t say anything. He kissed his wife on the neck and took me over to the side where she and Lori could not hear us.

“I told you last night that I think Rachel gets off on things not being fair. She also gets jealous when I show attention to Lori or her mom and not her. She’s never really shown jealousy when I show attention to Brad though. I’ve intentionally left her in the garage and ignored her because I think she secretly likes feeling this way sometimes.”

“Wallowing in her own misery?” I said incredulously. I couldn’t understand why anyone would do that.

“Exactly,” Dennis told me that I was correct. I was being facetious. It dawned on me that the girls liked pain and I didn’t understand that either. “You that said you had common sense earlier today. You understand what works for you. You’ve got a long way to go understanding what works for other people isn’t the same thing. Rachel could tell me she doesn’t want to do family day and it would be over for her. She’s never done that. I don’t think she wants to do that. I think she wants me to go in there and focus all of my attention on her.”

“So why don’t you?”

“I think it’s driving her crazy waiting for it, anticipating it and not getting it,” he explained. I didn’t understand fully why he wouldn’t want to tease her if that was what she wanted. “Just like you marinate a steak so that it grills up better there is some pre-work that has to be done. She is in there stewing. She’ll get her turn soon enough.”

I still didn’t understand what he was teaching me.

“Do you know what I like about you?”

“No,” I admitted.

“You are sensitive, and you care about how other people feel. That’s good and it is going to serve you well. The problem is that you don’t truly understand how our weekends work. We aren’t like this all of the time. The rules are different on family weekend. I get to be a complete bastard and I know the girls are having fun because every month they get naked and line up for me so that I can do it all over again. I trust them to know what they enjoy, and they trust me to be in charge of them for a weekend.”

Wow. I understood that! He made it so simple for me. I began to have a revelation. I think he could see that on my face as well.

“Today, you can cage the girls, play with their tits, fuck them, smack their butts and have a good afternoon. I’ll be home at 7pm and take back over. You can hang out and help me with them if that is what you want and that’s all that has to happen.”

I nodded. That sounded REALLY good.

“Or...”

I was intrigued. What was the other option?

“You can take the girls to the Coastland mall and do something with them like we did yesterday.”

Wow!

“You’d let me drive your car?”

“No, not by yourself. You don’t even have a license,” Dennis told me not to get ahead of myself. “Here is what I will do for you. I am going to tell you that you are not to leave the house today while I am gone.”

I didn’t understand.

“Do you remember when we talked about the apple in the garden of Eden?” He could see I didn’t understand him. “Never mind, don’t over think it. Just be yourself today,” he said.

I didn’t really like myself the way I was, and I didn’t think anybody wanted me to be “how I am”.

“I am going to tell the girls that you definitely cannot leave the house. I will leave you my keys and give you a hundred bucks that I am going to tell you is for babysitting my daughters.”

“Thanks!”

“Don’t thank me yet,” Dennis smirked. “After you are sure I am gone you can order Lori to drive you and Rachel to the mall. You don’t have to make them ride naked and obviously you won’t want to handcuff Lori if she is driving. You are to spend that money on them today.”

“That’s really nice of you!” I gushed.

“I am a hell of a guy, what can I say?” Dennis didn’t want to be flattered. “I gave my son twenty bucks for doing nothing. I want you to make the girls really earn it. They deserve something nice though. I am selling all of their old shit, so why not go out and buy new shit?” he chuckled.

“I can make it like a contest!”

“Not everything needs to be a contest,” Dennis warned me.

“Yeah, but the girls got very competitive yesterday.”

“That can be a good thing and a bad thing. What do you have in mind?”

“Well, I’d like to spend some of the money today on them, but I could give the one who is the most obedient and willing to humiliate themselves fifty bucks!”

“Rachel already thinks the games are rigged,” He snickered. “I like that your first thought is to use a reward as an incentive. I am going to do another favor for you!”

He walked over to Lori and pulled her shirt down to cover her ass. She blushed and pretended she hadn’t noticed. There were several guys who had been strategically standing and gawking at her bare-ass that definitely DID notice. He took her into the garage.

“Okay sluts, we’ve got about an hour to finish this garage sale. I do not want you to leave this house today.”

“Awww, Daddy!” Lori and Rachel pouted.

“Don’t aww Daddy me,” he said. “I am giving your babysitter a hundred bucks to kick your asses this afternoon.” Dennis made a show of counting out twenty-dollar bills for me. The girls definitely seemed jealous that I was being paid.

“You can do anything I would do with them except leave this house or hang them by their necks! You can shock the shit out of them on these electric chairs,” he flicked the switch on Rachel and let it buzz in her pussy.

“The one thing that I want done today besides cleaning the house is they are to mow the lawn! I want both the front and back done TODAY.”

“Daddy, I’ll make Brad do it this week, I promise!” Lori begged.

“No, I am making YOU and your cunt sister do it TODAY, and HE is going to see that you do. They have to be street legal on the front yard, but I’ll show you the smallest bathing suits they own. I don’t care if you have them do it together or send one of them out there. That’s your call.”

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