Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 25

Coming of Age Sex Story: Chapter 25 - 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  

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“How long was I out?” I woke up face down in the salty water with my head in the sand. It felt like I had just been struck with the combined force of Thor’s mighty hammer as it struck 1,000 suns and caused them to explode.

I am being overly dramatic, but my jaw definitely hurt like a motherfucker!

“Quick, someone give him mouth to dick resuscitation! OH, he’s already up,” Lori’s snarky tone was unmistakable. The Wagner women had their bikini bottoms back on and were standing around under the pier.

Dennis was squatting down by my side. He helped me up and dusted me off.

Willy and the other skid-boarding surf-rats he hung out with had disappeared immediately after I hit the ground.

Judith was still perched up on a jagged rock. She looked concerned for my well-being.

“You are alright, walk it off, Son.” Dennis got me to my feet. Doris comforted me and wiped my chin.

Judith seemed perplexed and a little amused. “You didn’t have to do that for me. My notebook contained just some random.”

“Is this your GIRLFRIEND, Brian?” Lori’s playful snark was not at all welcome. I felt humiliated and defeated because I had just been clocked with one punch. I genuinely felt embarrassed because I had only moments ago realized that Judith was a girl that I might like to get to know better.

She was quirky, and I felt like a fool for not realizing that was the perfect type of girl for me. I was quirky as fuck!

“No, I do not have romantic feelings for Brian. We share an introductory French class together and he was gallant enough to face down my brother for my honor. Alas, it was but a forlorn hope for victory against the mighty Guillaume this day. The effort is what matters most, and you have my gratitude.”

My jaw felt shattered, but my dick immediately got harder when I heard her eloquent summary of what happened. She made it sound almost cool that I just got my ass kicked with one punch. I loved her flowery speech. I was a massive fan of movies like Ivanhoe and Camelot.

I’d never heard anyone speak in Pidgin Shakespeare before. Her speech was dotted with old English phraseology that sounded like something straight out of a renne faire. Modern medieval fairs were something that I didn’t know existed at the time. If I had, I would have realized they were quite similar to the Wagners gatherings on a larger scale. People played characters and ad-libbed little stories while eating smoked turkey legs and watching men joust on horseback.

“Why are you hanging out with the Worthington clan, on this day, Rachel?” Judith asked. She recognized Rachel from school. I didn’t know how well they knew each other, but Rachel obviously recognized Judith as well.

“Worthington?” Lori pursed her lips in confusion. Rachel seemed puzzled at first as well.

“This is my Uncle Dennis,” I introduced Dennis and said that Rachel was my cousin. That was a decent lie and a quick solution to Judith’s confusion about me telling her that they were my family. I felt pretty good about that. It seemed unlikely she’d ever meet my parents and the topic of my Uncle and cousins would come up.

Judith accepted the explanation without further clarification required. She was shy in class, but now that her brother was gone, she seemed more animated when speaking to the Wagner family. Judith spoke rapidly and always used very large words when smaller ones would do. It made her seem impossibly clever and perceptive (to me) but I think it annoyed the Wagners.

“Settle something for me,” she said. “Were you simply indulging in naturist activities by swimming as nature intended without the earthly restrictions of these clothes that society requires us to wear,” she lifted the sides of her own rather bulky black bathing suit to emphasize her question. Judith continued, “Or were you as Brian contended required to run with your bottoms around your ankles because you had misbehaved?”

Judith’s tone was inquisitive and not judgmental. She remained aloof and almost scientific about her question. I wasn’t sure if she could tell I was l was lying. Judith seemed quite innocent but was clearly quite book smart.

“The bottoms were around our knees, and yeah, we got in trouble,” Lori admitted. “I keep writing checks with my mouth, that my ass has to cash.”

Judith paused for a moment as if she were filing away what Lori said in to the massive mental databank inside of her brain. “Your family openly advocates female submission and male dominance through the practical application of domestic discipline as a relational approach to family dynamics?”

Dennis wasn’t dumb either. He understood her completely. He told her that was one way to put it and left out the details.

Judith’s eyes twinkled when she had new information. She didn’t blush or seem at all flustered. “I’ve read about systems of male dominance established by systemically historical cultural norms. What would you say to the application of discipline with the goal of establishing a matriarchy and norms were reversed, so that men had no say in the day-to-day dealings economically and socially, but simply existed to serve a functional purpose?”

Judith had rattled off so many big words and concepts that I think most of us were a little flustered.

“Don’t feel that you must answer the question. I was simply curious as to your feelings one way or another on the matter. I am ambivalent on the topic. I only sought to broaden my range of understanding, and you are the first people that I’ve met who are practitioners of the more traditional forms of gender norms.”

“You got all that from us showing our ass cracks on the beach?” Lori chuckled with amusement.

“I apologize if the nature of my query is too personal. My brother drove me to the beach at my parent’s instance. I would much rather be curled up with a good book on this lovely Saturday afternoon. The only mental stimulation I had was my journal, and I am afraid with it’s unfortunate destruction, I’ve little else to do but sit on a rock and annoy random passers-by with my less than engaging line of questioning.”

She spoke rapidly and sounded very intelligent. It was exciting.

“Are you aware that you are wearing your bathing suits incorrectly?” she asked as if the girl’s might not have realized that their bikinis were turned the wrong way.

“Yes,” Doris said. “That’s how we have to wear them today.”

“Oh, that’s fine. I am not attempting to insult you. I just wasn’t sure if you were aware. I often like to wear things in the manner that they were not intended to be worn.”

Doris and Dennis seemed to find Judith rather charming in a strange way. Lori and Rachel clearly thought she was weird and a little annoying. I didn’t want her coming with us because I was afraid that she would see just how perverted they were and by extension I was.

It was the first time that I was kind of ashamed of myself for participating in the Wagner’s play activities. I didn’t want Judith to know what I had been doing.

“Any friend of Brian is a friend of mine, You are welcome to come along with us,” Dennis offered to let her see first-hand just how they lived.

“I choose my friends rather selectively. Despite Brian’s willingness to defend my honor at the cost of his own physical pain, I would not say that we are friends, but simply classmates or colleagues. I appreciate the offer and thank you. However, I must decline as Guillaume would be happy for an excuse to ditch me here when he inevitably returns to the pier and discovers that I’ve wandered off.”

Judith offered her reply in a very polite but conciliatory fashion. She expected there to be no hard feelings and simply wanted to establish that we were not friends. It still hurt my feelings a little bit. The truth of the matter was that she was correct. I barely knew her.

I was starting to become intrigued by her though.

We parted ways with Judith amicably. Dennis had a small cooler that he was carrying in his hand with some water and beer. He also seemed to have a destination in mind on the pier. I was excited to get back to the game.

I did wonder what Judith would say if she knew what Dennis had in mind for the girls.

“That girl has the HOTS for you,” Lori teased me. Doris and Rachel both joined in to tease me.

“You heard her. She said that I was a classmate and nothing more,” I blushed.

“You have to learn to read between the lines with women,” Doris offered sagely.

“Yeah, these lines,” Lori put her fingers to her crotch and made a peace sign, then put them to her lips and vulgarly pretended to eat her own pussy.

“She’s perfect for you, Brian,” offered in a polite and congratulatory manner. I think that made me feel terrible. I felt like Rachel was confirming that there would be and could never be anything between the two of us.

“Did you see her fat camel toe? You could park a ship in there,” Lori made an “Ay-Ooga” ship horn noise and pretended to drive an imaginary ship through what she imagined the gap in Judith’s parted pussy lips would have looked like. I hadn’t noticed but everyone else had apparently seen it. The black spandex suit swim that Judith wore had clung to her body tightly. I had never noticed that she had well rounded boobs because she always wore baggy clothes to school.

“She had some massive milkers too,” Rachel was joking and didn’t say it in a mean way. “Hey Brian, get used to milking those puppies in the morning!”

Rachel squeezed the air like they were a huge set of milky knockers that she was squirting into her mouth. She and her sister chuckled the most over that. I was a little embarrassed.

I knew that Lori and Rachel were way out of my league. I enjoyed touching them and bossing them around. I was still unsure why they let me. My confidence was a little fragile and when they suggested that I could get with Judith I wondered if they were trying to put me down by insinuating that I could only get a nerdy girl.

That didn’t seem to be what they meant though. I think they were just having a good time teasing me while they could. There was nothing malicious about how they said any of it.

The girls continued to tease me about a future relationship with Judith for quite a distance as we climbed the stairs onto the pier and made our way to the men’s bathrooms.

“Hey, I thought you were supposed to do whatever we say today and behave!”

“So make us,” Rachel dared me.

“Yeah, why don’t you practically apply some male dominance to convey some female submission or whatever the fuck she was talking about,” Lori scoffed at Judith’s pithy choice of words.

“I think Brian would rather learn about the converse application of female dominance to reverse traditional gender norms,” Rachel added.

“You two are going to get it so hard!” I fumed. They were winding me up. I needed that.

“Oh, I am so scared,” Lori said as she casually walked into the men’s room with the rest of her family like she belonged there. The men’s bathroom was across from the women’s bathroom in the middle of the pier. There was no door. The entry was open and required someone to turn left and walk down a short hallway and turn left again so that there was some privacy to the people inside.

The bathroom had a dozen stalls, and several urinals. There were men in the bathroom going about their business. The first couple seemed surprised when they saw Doris, Rachel and Lori and hurried out.

When I took Lori to the men’s bathroom at the high school game there was a lot of shocked derisive laughter when guys saw her. The men who saw them were confused and a little more mature about it so they simply left.

“Okay, ladies. Let’s get back to our game of the Cunt is Wrong! In this contest,” Dennis introduced a nasty contest he had worked out. He had used his engineering skills to take three cheap plastic water bottles and fill them with sea water. He placed a straw in the tops of each bottle and handed them out.

He picked a stall in the back and ordered the girls to get naked. He took their swimsuits and dropped them on the floor as all three women piled into a single bathroom stall and stripped excitedly. I slid into the corner near the door to watch once the door was closed. Dennis lifted the toilet seat.

“Bend over the toilet,” he pointed to Lori first. She smiled invitingly, stuck her ass up and rested her chin on the rim of the toilet bowl. The best way I could describe it was imagine a sexy, naked woman voluntarily lining herself up perfectly to have her head chopped off in a guillotine.

“Suck, don’t swallow,” Dennis handed Doris and Rachel one bottle each of the salt-water mixture.

“That’s the first time you’ve ever told me that,” Doris seemed amused. Dennis pinched her nipples and insisted she take a huge gulp. “I want your cheeks to be full, so you can fill her cheeks!”

He pushed a plastic straw into Lori’s asshole from the remaining bottle. Then he pushed her head down in the toilet without warning and held it down while she struggled and gurgled.

“Blow!” he ordered the other girls to bend down and spit the salt-water into the straw in her asshole and empty their mouths. Lori struggled in pain. The salt apparently stung her raw asshole and she bucked and gyrated her hips. Every time she bucked hard enough, her father grabbed her hair and pushed her face down into the water.

They repeated this exercise over five times. It was enough for each girl’s water bottle to be half full. Air bubbles were starting to emerge in the straw and saltwater leaked down her thighs. Her wet pussy was soaked.

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