Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 5

Coming of Age Sex Story: Chapter 5 - 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 naked women sitting on the floor, legs spread showing their pussies, and smiling widely

“I beg your pardon?” I trembled. Dennis glared at me like he expected me to get naked in front of him. He seemed to enjoy my fear – almost savor it.

“You heard what my question You don’t have the balls, the money, or the muscle to make me say it again,” Dennis sounded threatening, but he didn’t raise his voice. I have to admit I was afraid he’d reach out and snatch by my neck and strangle me.

“The optimist says the glass is half full. The pessimist says the glass is half empty. Do you like tying people down or being tied up?”

“I don’t know,” I admitted. I certainly enjoyed tying Rachel up because I had the opportunity to touch her and that alone had made it pleasurable. I really hadn’t processed any of this fully yet. His rapid fire questions made me nervous. I believe that was his intention.

“Then why don’t you strip for me, and we’ll find out,” he insisted.

“You really want me to get naked?”

“You got naked for my daughter, didn’t you?”

“That was to take a bath, Mr. Wagner.”

“I’ll give you a bath. I’ll give you a really good one. I’ll wash your tight little hiny-hole for you and everything,” he plucked his thumb from his daughter’s asshole and pushed her belly to the ground.

The way she was tied so that her thighs and calves were bound prevented her from going completely flat.

“I don’t want a bath,” I replied. I was nervous. My lips were parched and I was feeling the heat. Did he expect me to strip and behave like the girls? That seemed like the end of the world to me.

“Oh? I wasn’t asking if you did,” Mr. Wagner said. “I was telling you to get a bath!”

“Would you stop terrorizing him, Dennis?” Doris asked.

“I thought you sluts explained to him how all of this worked?” Dennis seemed annoyed by his wife’s interruption. My Dad would have never spoken to my mom that way. I don’t think my Mom would have let him!

“No, we didn’t get to how the weekend worked. I wasn’t sure if you were even going to let him stay.”

“What am I supposed to do? Put the boy up in the Naples Beach Club? Get him a suite? I planned to take you all to the beach when your brother gets home tomorrow. It was going to be glorious,” he said. “Now, that is on hold. Rachel stuck us with him. I’ll deal with her for that. The boy is my problem now.”

I didn’t want to be anyone’s problem!

“Why can’t you take us, Dear?” Doris seemed inclined to just bring me along.

“Take this little snot-rat with us? So, that he can tie half-ass Boy scout knots?”

That hurt my feelings a lot. I thought I had done really well. Dennis could be brutal with his criticism. I think it was why so many people seemed to seek his approval as well.

“I am so sorry for ruining your weekend, Mr. Wagner. I could probably just stay here while you go to the country with your family?”

“Stay in my house? Without any supervision? Now, I know you are dreaming. You didn’t let me finish. You aren’t very good at tying knots. You seem like you need a whole lot more practice before you might be worth a rat’s tender asshole. I suppose it’s my duty to teach you how to tie up a girl properly. You’ll end up hurting or disappointing somebody somewhere along the line if I don’t.”

“Thank you,” I said.

“I am not doing it for you. I am doing it for the girl that might have a very lackluster experience with you. I don’t want you to say you learned any of this third-rate boy-scout shit from me,” he insisted.

In his curmudgeonly way, Dennis was telling me that I was invited to spend time with his family this weekend. I was absolutely thrilled, and I was flattered that he painted a picture where I’d even have an opportunity to disappoint a woman in the near future. That was better than never having one at all.

I didn’t associate bondage with sex, but he had implied it was involved and I was a pretty fast learner. He could tell from my face that I was more than just a little excited about the offer.

“Don’t thank me just yet! You’ll carry my cameras and unload them. If you damage one of those, I’ll take it out of your ass. You won’t touch my girls without permission from me and if you damage one of those, I’ll take it out of your ass. You will have so little ass left when I am done, that you will be shitting out of your shoe. In fact, I am promising you now that if you fuck up anything of mine or anyone else’s for that matter, you know what I will do?”

“Take it out of my ass, Mr. Wagner?” I had to stop myself from chuckling. His demeanor as an ogre had rapidly decreased in intensity. Rachel’s father still seemed like a hard-ass, but he wasn’t breathing fire and brimstone any longer.

“First of all, I don’t want you to ever call me Mr. Wagner again. I wanted to see if you would haul ass or shit your pants and you didn’t do either. Well done,” he rubbed my head and tussled my hair. I was proud of myself.

“I was mostly bullshitting with you, to see how you responded when I first got home,” he admitted. “I am an ass-hole, but I am an equal opportunity asshole. I hate EVERYBODY equally the same. I have the same level of disgust for everyone. Some people think that just because I hate them that I am prejudiced against a certain race or religion, but I don’t have a prejudiced bone in my body, Brian. I have as little regard for you and your well-being as I would anybody else,” he said.

I assumed Dennis was joking but I really couldn’t tell. Dennis had an intense way of speaking. He often said things and left a pause after he finished what he had to say. I felt the need to respond, but I don’t think he wanted me to say anything at all.

He paused and waited for me to say something, and when I didn’t, he actually seemed to glower a bit less.

“You can call me Dennis or Dad. Everybody does,” he added. His mood lightened some but he still seemed chaffed to have me in his house.

I didn’t want to call him Dad, but I was flattered that he’d make that offer so soon after meeting me.

“Second of all, I meant what I said about spreading rumors. Lori gave herself a reputation. I don’t need YOU giving Rachel one.”

Lori glared at her father and murmured. She was still gagged. Her asshole was still facing me. I couldn’t even look at it for fear that Dennis would catch me staring and say something about it.

“Yes, yes, my precious little Barbie-doll princess, I’ll get to you when I get to you. As you can see, I have an unexpected guest in my house during family weekend. That’s never happened before. I didn’t think any one of my children were that stupid or careless.”

He glanced down at Rachel. Her butt-hole was also sore and puffy and hung open slightly. I could see where she made poopy and that fascinated me. I barely even stared at her pussy. She had one long cunt lip and one short one and that puzzled me, but it didn’t fascinate me the way her ass did.

“You really are an ass, man. Aren’t you?”

“I don’t know, but I think so,” I admitted that I was just learning.

“Well, my house is kind of like a library. You can borrow a book, but you can’t check it out and keep it,” he smiled at me. I didn’t quite get the metaphor, but it sounded promising. “You seem kind of old to need a babysitter. Let me guess, you were starting to outgrow them, and then Rachel came over to babysit and you begged Mommy and Daddy to keep her coming over?”

I didn’t want to admit that was true. I blushed and shook my head yes.

“I was a teenager once, way back in the civil war days,” he chuckled. “The good news is that you will grow out of being an insufferable little asshole and mature into an insufferable old asshole like me one day. This is what you have to look forward to, lad.”

He slapped his fat belly proudly and thumped himself. “If you are lucky, and you work hard, you’ll find a trampy whore like this,” he squeezed Doris’s cheek very hard. She instinctively moved her head away, but she couldn’t move it far enough to prevent him from pinching her. “You’ll fall in love and fuck her a million times. A few of those times she’ll pop out some ungrateful little shit-machines that require constant feeding and care. You’ll spend your life working your ass to the bone so you can come home and crack a beer and a few whips. Then you’ll die, turn to dust and be forgotten,” he added somberly.

“It’s the circle of life,” he added when I didn’t say anything. “Enough with the formalities and introductions,” he announced. “Judgment is going to be delayed,” he didn’t have to step on the stool to reach the women in the cage.

The women groaned as if they were disappointed.

He began to unfasten his wife’s cage first. The cage was very simple, but the locks and bindings were not. There were double locks and restraints I hadn’t noticed at first. It would have likely been impossible for the girls to get out without destroying the cage in the process.

“We are going to watch your brother beat the snot out of Naples High School,” he announced the surprise he had planned for his family. I was apparently going with them.

“Oh, Bradley will love that,” Doris seemed overjoyed. The other girls not so much.

“Then we will do judgment and you girls can hang around while we celebrate Bradley’s victory!”

The girls seemed pleased to hear that. I didn’t know what judgment was but it seemed like the implication would be that they would be the ones judged and they should probably NOT be looking forward to it.

Up was down, and left was right in this family though as far as I could tell. They had an entirely different way of processing the world where pain and constraints seemed pleasurable to them.

I was reminded of the Addams Family or the Munsters. They were two very similar sit-coms and they were some of my favorites. I especially enjoyed the Addams family as the humor seemed a little less slapstick.

The Addams belonged to a rather odd and wealthy aristocratic family that delighted in the macabre and were seemingly unaware or unconcerned that other people find them bizarre or frightening. Morticia Addams was intensely beautiful and sexy and as you may have guessed – I had a crush on her as well.

I could picture Morticia Addams loving the cages and ropes that the Wagner’s used and finding a lot in common with them. In fact, the more I thought about that scenario, the more I could not fantasize about Morticia without including the cages or ropes in them.

“Don’t just stand there with your hands in your pockets playing pocket pool, Son. Make yourself useful,” Dennis snapped me out of my fantasies of Gomez Addams getting turned on while he stretched his naked wife out on an old-timey wooden rack in front of Pugsley and Wednesday.

I was surprised that he called me “Son”. I wasn’t sure if I should read anything into that, but I didn’t question it. I was also surprised that he asked me to do anything at all. He let me untie Rachel who had been patiently waiting on the ground. She had already closed her legs and flipped over onto her butt after her father had finished with her.

It was harder removing the binding than it was putting them on. He reached into his pocket, unfolded a buck knife and handed it to me blunt end first. He held the blade in his hand without fear that I might cut him when I accepted it.

I was extremely careful not to cut him. I kept feeling like he was testing and evaluating me and he probably was now that I think about it. If I had cut him with the knife, it was probably likely I would have cut his daughter when I went to remove the tight rope around her thighs.

Dennis may not have said it, but I strongly suspected that he would have rather found out I was going to be irresponsible with the blade when I sliced his hand than when I cut his daughter.

I felt like I shouldn’t have a sharp object so close to his daughter’s bare skin. However, she didn’t flinch away or appear frightened. “You didn’t make my tits turn purple,” she smiled up at me as I started to free her.

“You didn’t want to kiss me anyway,” I replied. I kept my eyes on what I was doing instead of staring deeply into her adorable brown doe eyes.

“Thank you for trying though,” Rachel offered sweetly. Her mood seemed less dark now that her father was there.

“Move a little faster, talk a little less,” Dennis chided me for taking my time. I was being extremely careful about cutting the binds that held his daughter. I suspected he wanted me to move faster but also keep her safety as the priority.

He helped his wife out of the cage and allowed her to use the stepping stool to get out. She shook her arms and legs and sighed as if she was sad to have to get out.

“Did you shit and piss already?” Dennis bluntly asked her what seemed like an inappropriately vulgar question to ask a woman like Doris (or any woman really).

“I pissed once earlier, but not recently,” she didn’t seem offended by the question at all.

“If you ask permission to take a shit at the game, I am going to drop kick your cunt back to the parking lot,” he insisted. The girls didn’t seem offended by his threat. “Did Rachel feed you?”

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