Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 42

Coming of Age Sex Story: Chapter 42 - 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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“Wow, we’ve been promoted from 25 cent whores to five-dollar whores,” Lori joked as we left Sears.

I was about to give her a new punishment dare when I saw someone I recognized. It was Judith Scott. She was the girl from my French class. She styled her straight black hair with thick bangs in the front. She was wearing a black T-shirt that was captioned “Don’t Dream it, Be it”.

Judith had a very blocky figure and a quirky kind of walk. Her brother Willy was walking a few paces ahead of her as if he was trying to avoid being seen with her. She waved at me and gave me a friendly smile when she recognized me.

I don’t think Willy noticed me. I have to admit that I wasn’t excited about a rematch after he laid me out at the beach.

I waved back at Judith. She thought Lori and Rachel were my cousins. I wasn’t embarrassed to be seen with Lori and Rachel. I just didn’t want her thinking I was a nasty boy. I didn’t want Judith catching me punishing the girls at the mall. I didn’t know what she might think of me.

“Go talk to her,” the girls prodded me to flirt with her.

I will be honest with you. I was channeling my alter-ego Eddie that afternoon but only as it related to Lori and Rachel. I was still unsure of myself talking to another girl. I was very intrigued with Judith after I saw her at the beach and the Rocky Horror Picture Show.

I just didn’t want to get shot down. I thought that if I tried to hit on her and failed that would crush my ego and hamper the confidence that I had been cultivating all afternoon. I was doing just fine as it was. I could also talk to Judith at school when I was not on the spot. If felt that if I failed in front of the girls, they may laugh at me. I didn’t want to risk it!

I made up an excuse. “No, I am being paid to babysit your fat asses and I will do that. I am not going to flirt with girls while I am babysitting.”

Rachel and Lori didn’t push the issue. I think they probably saw right through my excuse though. They were pretty savvy at picking up on body language. We stopped in a Hallmark store. They sold greeting cards, engraved gifts and a few office supplies. I bought some thumbtacks. I jabbed one into my skin to see how it felt. They hurt! The girls giggled when they saw me wince. I gave them each a box of tacks to carry to punish each other with.

I sighed and told Lori that it was time for her punishment dare. My confidence had grown quite a bit and even though this was all role-playing I truly felt in charge of them.

“I will take you to the shoe store. You will sit in a chair with your legs spread. You will keep your hands on the arms of the chair. You will accept help from anyone who offers to put shoes on your feet. If they touch you, you will let them feel you up. You will get a point after thirty minutes.”

I had thought of that thirty minutes ago. It sounded like an opportunity to be groped and vulnerable. Lori would have to wait there helplessly while anyone that wanted to touch her body copped a feel.

Lori looked at her sister to hear her alternative dare.

“Let me stick one thumb tack in the center of each nipple, three in your clit hood and one directly in your clit.”

Lori scrunched her nose as if reacting to the thought of how much pain that would cause her.

“How many points do I get for the needles?” she asked me.

“Two points,” I said.

“Hmm, that’s not a lot. How long do I have to keep them in there?” she asked me.

Rachel answered that it would be until we left the mall. I decided to let that stand.

“Where can we go so you can push them in?” she asked.

“The back of the store,” Rachel shrugged. We were in an office supply store that sold Christmas cards and engraved gifts. It didn’t have many customers and only one clerk at the front.

“Okay cunt, but you know what dare you are getting after this?” Lori assured her.

“You can’t recycle dares,” Rachel insisted. She looked at me to confirm if that was a rule.

“I don’t see why not, but I get to push the pins in.”

“You really want to? You have to jab them in much harder than you just did on your arm, or they fall out,” Lori asked. We walked nonchalantly to the back of the store. Her biggest concern wasn’t the biting pain of the needle but whether I had the fortitude to actually push it in to her all the way.

Lori lifted her shirt and presented her tits to me. I cupped one boob and pushed the needle in to the center of her tit – where the milk might come out. She groaned and her eyes got wide.

“You big baby!” Rachel slapped her sister’s butt.

Lori had small holes in the side of the nubs of her tits. She told me that she thought I was going to stick it into the existing holes. A little blood came out of her nipple, but she wiped it away and licked it. She dropped her shirt. Lori lifted her skirt and kept looking behind her to make sure the clerk wasn’t walking up on us.

Rachel went to the cashier to distract him. She didn’t flirt. Instead, she asked him questions and kept him busy. I am sure he checked her out though.

“You are a naughty slut! You were caught playing with yourself this morning and making fun of your babysitter! This pain is going to remind you what a dirty cunt you are,” I warned Lori.

“Oh!” Lori put her hand on mine when I jabbed the first needle into what I assumed was her clit hood. It was actually her clit. She squeezed my hand as I crushed the tiny-dick shaped part of her pussy that she pissed from and inserted the needle. I put all three in. She was moaning and gyrating her hips like she was having an orgasm by herself. I could not insert the fourth needle because there was no room. I jammed it into the side of her labia and left it there.

Dennis had inserted needles into her ass and pussy on Friday. I knew it had excited her but the way that Lori was wincing I realized I must have done something a little extreme.

“Does that hurt?” I asked.

“Fuck yeah,” she whisper-yelled and bit her fist. “It feels like five red ants biting down hard on my clit! You were only supposed to put one. Oh, fuck, oh fuck, oh fuck, oh fuck.”

“Should I take them out?”

“No, I can handle this! I want three points though!”

Rachel wasn’t happy when I told her that I gave her sister three points as we left the card store. The clerk had a smile on his face. I think he knew we were up to some sort of hanky-panky. Lori kept dancing like she had to go pee really badly for about twenty more feet before she normalized her walk.

“Okay, my dare for you is worth three points. It’s two tacks in the nipples, three in the clit, and one in the side wall of your long pussy flap!”

“Hey, no fair taking my idea!” Lori protested the fact that I had just given same dare to Rachel.

Rachel lifted her sister’s skirt and jabbed a thumbtack into her buttocks. “You forgot to call him babysitter”

“Okay, hmmm ... I get to give you a dare then?” Lori put her finger in her mouth and thought for a moment. “We’ll go into the pet store and buy you a leash and a dog collar and then I will walk you from one end of the mall to the next.”

“Naked and crawling like at home?” Rachel thought that was outrageous, and I did as well.

“No, you can strut around but you have to put your little paws up and beg,” Lori stuck her tongue out and let it wag and demonstrated by panting.

“You cunt,” Rachel groaned. To my surprise she chose the needles. I suppose she felt she couldn’t afford to lose three points against Lori. We found a bathroom near JC Penny. It was down a long hallway next to a water fountain. It was not as well known as the main bathrooms and only had two stalls. Lori watched the door as I punctured Rachel’s nipples with the needles.

“OW, SHIT!” Rachel balled up her fists when the first one punctured her skin.

“Oh, quit your whining, you big baby! I did it too!” Lori scoffed at her sister’s outburst.

“Do the other one,” Rachel had a slight tear in her eye as she insisted that I get it over with. She was incredibly stoic about it despite a tear coming to her eye.

I cupped her boob in my hand. I squeezed her nipple so that it was nice and firm and then I pushed the pin down into the center of her delicate nub. She squirmed but didn’t call out. A small trickle of blood began to roll down her tits. She washed it off in the sink before I could continue. Rachel kicked off her skirt so that I could pin her pussy next.

“I should have said use a stapler on that stench trench of yours, I can smell you from here!” Lori snickered as she kept the door open a crack so she could warn us if anyone was coming.

“That’s your upper lip you smell,” Rachel fired back. “Ahh! Ssssssssssssssss,” Rachel hissed as when the first pin hit her clit. “This is my clitoris and this is my clit hood,” she flicked the meaty fold above it.

“Shut up and take it, he forked me like I was a raw prime rib dinner!” Lori giggled wickedly.

I carefully applied the other two needles as I pinched her pussy lips and held them. Rachel showed me that by pinching the flesh it would minimize the bleeding. She cleaned them off.

“I am going to make two new rules,” I announced. “The first is that cunts cannot present punishment dares that were already offered. I can copy any old dares as often as I like.”

Rachel was wiping her pussy off with a tissue and washing the blood off. “That’s not fair!”

“I am the babysitter, and you two are the bratty cunts that got caught making fun of me while playing with yourself!”

“I knew I liked you, Brian. You are a little wicked,” Lori seemed amused that I had made an unfair rule for both her and her sister.

Rachel lifted Lori’s skirt in the back. She jammed a thumbtack into Lori’s left butt cheek before her sister could block it with her hand.

“Oww, what was that for?” Lori grabbed her hip and moved her hand to pull it out.

“You are supposed to address him Sir, Mister Brian or Babysitter,” Rachel beamed with amusement of her own.

Lori glared at her sister and left the tack in place. “Next time, don’t try to jam it into my stink-hole!”

“How about don’t let there BE a next time and you won’t have to be punished?” I offered my advice sadistically. I admit that I was gloating that the girls were now self-enforcing my rules. This may have been a made-up scenario but it was feeling more and more real to me. I think it was to them as well.

The girls broke character at times, but they seemed to take the rules fairly seriously. I felt they were having fun and that was what mattered the most. I didn’t feel like a villain at all though. I felt like a strict, sadistic babysitter.

“The other rule is that dares can’t get us kicked out of the mall,” I added.

“Fuck! That’s like half of the dares I had,” Lori mused and smiled again. I liked it when she gave me a bright toothy smile.

“Okay, time is wasting and I think you cunts haven’t learned your lesson. “This next dare we are going to take a walk. The entire length of the mall. I am going to make up for lost time by having you both pick one and we’ll do an entire lap until we get back to this bathroom.”

The girls groaned a little.

“Since you are such a vulgar potty mouth, my dare for you Lori is to go into Bath and Bodyworks, and pick any bar of soap. I’ll buy it for you and unwrap it and you’ll hold it in your mouth while we walk through the mall. If anyone asks you will lift your skirt and show them your punishment stamp.”

“God damn, I thought you didn’t want us getting kicked out of the mall?” Lori seemed impressed and a little scared of that dare. “I’d have to show my stinker to a rent-a-cop security guard if he asks?”

“I’ll tell you when to expose yourself and tell people what you did,” I added.

“Rachel, help a sister out. What have you got for me?”

“We’ll go into Victoria’s secret, and you’ll pick out a pair of panties. You’ll open them in the store and stuff them in your pussy under your skirt at the cash register. You’ll walk one length of the mall and drop them TWENTY times. You’ll bend over at the waist. Pick them up, and stuff them in your cunt again.”

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