Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 26

Coming of Age Sex Story: Chapter 26 - 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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“Does your dad hate you or something?” Leona laughed. Lori didn’t respond. Leona tossed the ball against Lori’s left butt cheek.

“He doesn’t hate me. I am just a brat. I am not pissed that I am getting punished. It’s my fault. I can’t help running my mouth and being a little cunt sometimes. I am sure you can relate.”

There was a seethingly passive-aggressiveness to how Lori made that last statement. I don’t think Leona picked up on the fact that Lori was trying to tell Leona that she thought she was a cunt that ran her mouth.

“He’s making you lay face down in the sand,” Leona reminded her.

“Yeah, so? That’s so you can kiss my ass!” Lori wiggled her butt a little. She was leaning so far forward that I could see her hamstring muscles tense. I eavesdropped for a little bit. I don’t think Kevin or Leona cared or noticed.

“Do you like it when I throw this ball at the back of your head?” Leona asked as she threw the ball against Lori’s head. It wasn’t a hard throw. It bounced harmlessly onto her back.

“No,” Lori said as she reached down, picked it up and harmlessly tossed it back.

“Why are you letting me do it to you then?”

“You heard my dad. I’ve got to do what you tell me for an hour. I’ve been pushing his buttons all day, and he’s tired of my shit. He made me your problem for a little while,” Lori explained.

I interjected and cleared my throat. Kevin looked up at me politely. He was just enjoying the view and trying to make sense of what was going on. Leona was the sadistic one. “My sister is supposed to call you Ma’am and your boyfriend Sir. We made a rule today because she is so disrespectful. If she doesn’t feel free to spank her dumb little butt.”

Leona looked up at me like I was an annoying crab that had just pinched her toe and wouldn’t let go. “That right? You have to call me Ma’am?”

“Thanks SIR,” she addressed me sarcastically for reminding her. “Yes, Ma’am. I told you when we got here that I agreed to do whatever I was told today to make up for the last time we were here.”

“Do you regret agreeing to that?” Kevin asked. He appeared to be a little worried Leona would lash out at him for even talking to Lori.

“No, this was fair. We were pretty shitty the last time we were here. Payback is a bitch, Ma’am.”

“Yes, it is. The last time I saw you was at Rocky Horror Picture show. You were walking with my ex-boyfriend. He played Brad in the cast. The guy that played Rocky was crawling around sniffing your feet and ass like you were a goddess.”

“That’s my brother,” she snickered.

“I thought THIS was your brother?” Leona indicated me with her thumb.

“That’s my other brother,” Lori lied effortlessly. “I am sorry I took your boyfriend, Leona. If it helps, I don’t even remember his name.”

Leona kicked Lori’s ass and made it jiggle. Lori looked uncomfortable but faced forward.

“I said spank, not kick,” I clarified. I felt obligated now to watch over Lori. Leona was being ruthless.

“It’s fine, Sir. That tickled,” she said. Then she asked me like she didn’t care at all about Leona “Hey, do you want to ask Dad if we can go to Rocky Horror tonight? I haven’t been in six months and you are a virgin.”

“I am NOT a virgin!”

Everyone laughed when I said that like they didn’t believe me. I didn’t realize that they meant virgin in the sense I’d never seen the movie in a theater.

“What color is Rocky’s underwear?” Kevin asked.

“White?”

They all laughed again. I wanted to say poop-striped but I thought better of it.

I was reluctant to go, because the movie really didn’t sound very interesting to me. Leona said that it was just a place for posers and weirdos.

“Yay Rich Weirdos!” Lori replied enthusiastically. I didn’t get the reference she was making to Rocky Horror Picture Show (RHPS).

Leona kicked Lori in the ass again and Lori thanked her. “You like being kicked in the ass?”

“I already told you that I do not, Ma’am, but I don’t mind. I have a fat-ass and a lot of cushion.”

“You are really twisted?” Leona scrunched her nose and kicked again. This time she must have felt the straw poking up out of Lori’s asshole. I had observed the straw slowly lifting Lori’s bottoms up like a reverse boner. Dennis had pushed it up her ass earlier, but now she couldn’t stop it from coming back out.

“Is that a drinking straw in your ass?” Leona seemed mortified. Kevin didn’t know what to make of it.

“Yep, care to take a sip?”

Meanwhile, Dennis was down in the water with Rachel. He was dunking her head under over and over while she held two bikini bottoms in her mouth. I wondered if he had really made her suck them clean with her mouth. She was gasping every time she rose out of the water.

No one noticed, because Dennis played it off like he and his daughter were just goofing around. They were far enough away from the shore that nobody would have suspected anything. If anyone did look, it would appear that she was diving under the water or getting hit by an incoming wave and then spitting water back out and trying to float.

Doris was back on the shore near our camp. Dennis had made her dig a shallow hole in the sand and lay down in it flat on her back. The words “PLAY WITH ME” were written in the sand near her. Dennis had used a plastic sand bucket to create a tower over each of her boobs. The sand was flat otherwise. The bottle that had been in her pussy was in her mouth. She was a completely immobilized human sandcastle. Her feet were sticking out and Dennis used the opportunity to tickle his wife’s feet and then run a scratchy brush on them.

Doris’s laughter was infectious. She was in classic “Predicament bondage” as Dennis had described it to me. His wife was immobilized and she was having the piss tickled out of her and yet she seemed to be enjoying every second of it.

We watched for a few minutes before the attention shifted back to Lori again.

“I can see your disgusting crotch. Why do you wear your bikini bottoms like that?” Leona snickered at Lori.

“I told you earlier, Ma’am. I agreed to do whatever my dad and brother told me to do today because I was such a cunt to them the last time we went to the beach. It was the only way they’d take us again. They wanted us to wear our bikini bottoms like that. It’s no big deal,” Lori sounded annoyed and not polite at all.

Leona didn’t believe her or understand the point. “No one thinks your sister is even wearing top. I hope she realizes that she isn’t fooling anyone.”

“Yes, Ma’am. I think she knows.”

“You guys must have really fucked up. What did you do?”

This was the fun part. Lori started admitting to rude shit that she clearly never did. She painted herself as a thoughtless asshole (but I knew that was not true!) I think she would have admitted to being D.B. Cooper, the famous bank robber that got away with millions. I made up rotten things she and her mother and sister did as well. The more outrageous the better. Leona seemed to get off on the salacious admissions of guilt. Lori fed off of my responses and exaggerated them.

“Is there something else in your ass?” Leona finally asked in horror.

“No, that’s in my cunt, Ma’am,” Lori casually reached behind her and adjusted the tip of the water bottle.

“Why do you have a WATER BOTTLE in your pussy?” Leona asked incredulously.

I suspected Lori might make a wise crack about her having the bottle for the same reason she had the straw – and suggest Leona take a drink out of her bright and shiny ass. Lori remained contrite and apologetic instead.

“I don’t have any dildos, and I am not allowed to get any dick today. Dad found out Mom and Rachel were using a bottle too, but he hasn’t discovered mine yet.”

Lori had admitted to organizing gang bangs, ripping people off, stealing cars to go joyriding, using her dad’s credit cards without his permission, stealing other people’s husbands, and a number of seriously fucked up things. I assumed most if not all of them were lies. The one thing that Leona seemed to think was worthy of getting up out of her chair to tell on her about was the bottle.

“Mister Waaagh-nurrrrrrrr,” Leona waved at him. Her voice was so annoying. I don’t know how Kevin stood listening to it. It was the worst when Leona whined like that. Dennis was so far out in the gulf that he couldn’t hear her.

“You don’t have to get him. I can punish my sister.”

“You can punish her?” Kevin said he wished he could punish his sisters. Leona glared at him.”

Lori didn’t seem too concerned about being punished by me. She remained in her position face down on the sand until I told her to stand up and remove her bottoms. “Yes Sir,” she shrugged like it was no big deal. I smacked her ass sharply and she moved a little quicker. She pulled her bottoms down to her ankles and stood in front of Kevin with her ass exposed.

It was later in the day, and the beach clears out after 2:00 PM. There were still at least six hard-core beach-goers nearby that saw what she was doing. The old man with the red Kangal and speedos was the closest one to us.

“Legs apart, now squat down! Stand on the balls of your feet!” I made her assume a very uncomfortable position.

“How are you going to spank your sister like that?” Leona had watched Lori get spanked before and assumed that is what I would do. I wouldn’t call them ‘rivals’ because Lori was hot and Leona was dumpy, but right now, Leona had to feel superior in every way.

“I am not,” I explained. Then I asked Lori “Are you a horny chicken?”

“Yes?” Lori seemed confused but went along with what I asked her.

“Eyes straight ahead, wings ready to flap!”

Lori looked straight ahead and smiled excitedly. This was new to her – whatever it was.

“It’s a little bit of this, and a little bit of that, now clap your hands and shake your butt!” I repeated the lyrics to the chicken dance for her and clapped my hands and shook my ass a little. It was a silly song they play at weddings and parties for kids. I hated having to dance in general, but I especially hated having to do that song.

She began to sing the song, clapping and then shaking her ass over and over. Her knees were spread wide. The bottle in her pussy poked out slightly. “Now, push the bottle out slowly. If you drop it, then it’s going up your ass and I’ll get another one for your disgusting salty asshole.”

I think Lori almost laughed when I called her asshole salty. She was pretending to be very contrite and willing to accept her punishment. She didn’t want Leona to know that this was all a game. Lori pushed the bottle out of her pussy and sucked it back in. All while continuing to sing the silly lyrics in a happy up-time tempo. She stopped only to clap her hands and shake her ass when she got to that part of the song. She would intentionally push the bottle out as far as she could and suck it back into the dark recesses of her cunt after she shook her ass cheeks.

“Flap those wings!” I made her keep elbows bent and flap her arms like they were chicken wings.

I didn’t even know if she could do it. She did. Lori scrunched her nose in faux-disgust, but soon she was squeezing the bottle out of her pussy and back in like it was an accordion while she sang.

“That’s it! You weren’t supposed to have a dildo, were you?”

“It’s a little bit of this, no sir, I wasn’t, and a little bit of that,” she modified her song to answer me.

“You weren’t supposed to play with yourself, but we caught you doing that three times!”

“Now clap your hands! Sorry Sir, now shake your butt!”

“You weren’t supposed to give head, but we caught you bobbing under the water sucking off all these guys near the pier.”

“It’s a little bit of this, it was only three guys, Sir, and a little bit of that!”

“Yet, you keep trying to get away with it, why?”

“I love dick, now clap your hands! Now shake your butt”

“Sing ass instead of butt,” I prompted.

“Now shake your ass!”

Meanwhile, the old man in the red Kangol had walked past us at least three times starting at my sister’s outrageous behavior. He wanted to say something. Instead, he approached Doris and started a conversation with her. Doris had a plastic bottle in her mouth. I knew she could speak fairly well while gagged. I assumed she had to just listen to him while he stared down at her uncomfortable situation.

“Aren’t you afraid you are going to get in trouble?” Leona asked me. She was clearly amused by the spectacle, but she looked like she didn’t approve at all.

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