Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 39

Coming of Age Sex Story: Chapter 39 - 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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When I got upstairs, I permitted the girls to stand up. I liked watching them crawl upstairs. Their tits drug the carpet, and their asses were on full display. It had to be incredibly humiliating but also physically challenging to climb stairs on their hands and knees.

I repeated my criteria for what the could wear to the mall. They didn’t raise an eyebrow that I expected them to go without bras or panties and dress like sluts. I suppose there were a lot of girls that dressed that way at the mall.

I told the girls to hurry up and pick out clothes for each other. It was very surreal being the one to give instructions like this but it felt natural. I made it clear that I would approve of their outfit or tell them to change if I didn’t like it. I turned to walk out of the room.

“Do you want your pen back?” Lori stuck her ass out and pouted.

“No, keep that in there. I’ll be back in five minutes,” I said. I told them I had to use the bathroom. I even walked down the hallway and opened and closed the bathroom door. Then I snuck back to their room and waited just outside the doorway where they could not see me.

“Can you believe the nerve of this little fucker?” Lori giggled as she sorted through the bins in her sister’s room for something to wear. She laughed about an old brown wig that she found in the closet.

Rachel told her it looked good on her and suggested she wear it.

“Why would I want to hide these blonde locks? They make me look like a superstar! Brian would probably never go for it anyway. We wouldn’t want to upset our precious tiny king!”

“Brian is just trying to impress us by acting like a little Napoleon. Dad is going to be so pissed when he gets home that we left,” Rachel seemed happy I’d get in trouble.

“He’s probably going to blame us, and we’ll be hung for seducing him into going to the mall,” Lori said.

“Ooh, you really think so?”

“Yeah, you even told dad you wanted to go to the mall. He’ll think this was all our brilliant idea no matter what that note says. Who wouldn’t write a note in exchange for one of my world-class blow-jobs?” I could hear Lori sucking on something like a dildo or her sister’s tits to add impact to what she just said.

“I wanted to go to the mall but not without Mom and Dad.”

“Who knows? It might be interesting,” Lori shrugged. “He’s got some pretty wicked ideas. I am up for anything, and we may as well have fun.”

“Yeah, that’s true.”

“Besides, he’s got a hundred dollars in his pocket. We could probably separate him from that.”

“Ooh, a bet?” Rachel smirked. I wondered what the stakes might be!

“I don’t think he’ll give it to us directly. We might get him to buy us something cool, though? Dad basically sold half of my jeans collection and they still fit me.”

“Lori, I’ve got news for you. Those jeans are like two sizes too small!”

“Like I said, they fit ME!” I could picture Lori running her hands down her shapely thighs to indicate that she was actually a lot sleeker and thinner than she was. She liked to wear tight fitting jeans – that was obvious.

“Hey, keep an eye on the door. I want to have a little happy time with Mr. Toothbrush before Tittler gets back.”

“Tittler?” Rachel giggled.

“Yeah, like Hitler, only he is obsessed with our tits!”

“More like Assler,” Rachel snickered. “Hurry up. I want to get a little finger action in.”

“Just do it right there at the door!”

“What do you think I am doing ... uh-oh,” Rachel suddenly stopped talking. Her mouth hung open in shock as she tucked her head out the door. Rachel had one finger curled up inside of her pussy and a thumb in her asshole. I was only inches from her face when she looked around the corner. I caught them both masturbating red-handed. The girls stopped immediately when they saw me.

“Hello Brian,” Rachel smiled politely.

“Oh hello, Rachel. What were you calling me?”

“I was just joking, Brian!” Rachel offered a breezy apology. She tried to play it off like they knew I was there and were joking. “What did you hear?”

“Enough,” I said as I strode across the room. “Naughty girl,” I took Lori’s toothbrush turned it upside down and put it inside her pussy by the handle end. “Masturbation without permission!”

The girls seemed nervous. I think a chill ran down Lori’s spine. I told her to bend over and grab her ankles. Then I plucked the pen out of her ass and started to write on her butt. The ink was too small.

“Magic marker,” I called out to Rachel. I waved my empty hand. She gave me one they used to write their brother’s name on their asses before the big game. “No, a red one!” I tossed it at her.

She gave me a red magic marker. I wrote “I WAS CAUGHT PLAYING WITH MY PUSSY” on one ass cheek. I wrote “I AM A NAUGHTY SLUT!” on Lori’s other ass cheek. I smacked her cunt a few times with my hand.

I did the same thing to Rachel. “I WAS CAUGHT FINGERING MY CUNT AND ASSHOLE” on one cheek and “I AM A DIRTY GIRL!” on her other ass cheek. I smacked her pussy a few times as well.

“That’s it?” Rachel seemed a little confused.

I asked her what she meant?

“That is our punishment? I am not complaining. I am just confused.”

“Oh no, that’s just the start. Today is your punishment,” I explained as I capped the marker and stuffed it in Rachel’s puckered anus. Her knees buckled. I didn’t realize that I probably should have lubricated it first.

“Now stand up and get dressed! I’ll stay and watch,” I insisted.

“Dad never does that,” they told me that he made them come downstairs and model their outfits for him.

“Well, I am not your dad!”

They didn’t have anything to say to that. I was happy I actually shut them up. I wasn’t trying to be Dennis.

I made Lori show me the wig she had modeled earlier. It was a medium brown champagne brown. It actually looked natural on her (by the standards of the 1980s). Keep in mind that back then, girls frequently wore a lot of hairspray and intentionally made their hair look a little unnatural.

I told her she could wear it.

“Really?” she smiled enthusiastically. I think it seemed novel to her. The truth was that I didn’t want everyone to notice she was Lori Wagner and try to gravitate towards her right away.

Rachel naturally wanted to wear a wig after that. I was fine with that as well. She chose a blonde wig. I think she was a little jealous of her sister’s blonde locks.

The girls had big cannisters of Aqua-net, nail polish, blush, lipstick, blow-dryers and assorted beauty products strewn all over the bathroom counter. They styled their wigs almost like real hair! I have to admit it felt really cool to watch two naked girls blow-drying wigs, giggling and putting on make-up. I would have loved to just be a fly on the wall.

It really didn’t take them that long to fix themselves up, apply make-up, and find outfits for one another. They both chose short skirts and trashy tank tops. They didn’t seem shy about dressing like that in public at all. Rachel usually dressed conservatively at school. I liked her trashy look though.

They’d look like any normal mall slut that hung out at the Coastland Mall.

There were two camps of girls that frequently hung out at the mall. There were the ones who were really into Debbie Gibson. They wore bows in their hair, longer skirts, ribbons, and cultivated that sugary-sweet, goody-two-shoes look made famous by Olivia Newton-John in the movie Grease when she played straight-laced Sandy.

The other camp was the one I liked the most. The girls that were into Tiffany. They teased their hair out to incredible sizes. They wore oversized bangle earrings. They tended to wear trashy tops and short pleated stone-washed denim skirts with sneakers. They looked easy even if they wouldn’t give the time of day to a nerd like me.

There wasn’t much to do in Naples for a teenager. I considered these girls to be mall sluts because they seemed to always be at the mall whenever I went there. I didn’t think they were shopping or working. They were just there socializing with their friends and flirting with boys in the food court.

“You were talking about a bit earlier,” I said.

“We were just joking,” Lori apologized again. She tried to downplay the fact she was willing to bet she could separate me (the gullible kid) from the money her father had given me to babysit her.

“What were the stakes going to be?” I asked.

“Brian, we aren’t going to try to take your money,” Rachel assured me.

“Yes, you are. Whatever I do not spend today busting your lovely fat asses I am going to give to the winner of our game.”

“You don’t have to do that,” Rachel assured me.

Lori told her not to be so hasty.

“I am going to lose anyway,” Rachel shrugged as if that was a forgone conclusion. Her father had predicted that reaction perfectly.

“Today I am going to make sure that the rules are fair,” I insisted. Rachel seemed skeptical but they listened as I laid out the rules.

My plan was simple. I would give them a choice between two dares. The girls would get to alternate picking one of the dares. Completing a dare would grant them points. I’d give them bonus points if they were the first to complete the dare or able to do more than the other girl depending on the circumstances.

“You make up a dare. One of us makes up a dare. The one who didn’t make a dare gets to choose one of the two dares, got it!” Lori and Rachel both understood the premise right away. That made me happy. I was worried it was too convoluted.

That was simple enough.

“Okay, what if we don’t take any dares at all?” Lori asked. I made her explain herself. I thought she was going to say that they could easily agree to do the least possible to score a single point and then split the money at the end of the game. That is what I would have done if I was in her shoes.

“What if you give us a choice to go into Sears and stick a screwdriver in our pussy and try to drive screws or set fire to our farts with a lighter at Sbarro and we say no. What happens?”

Well, that was an interesting question. What happens if they refused to do both dares? I hadn’t even thought about that. I didn’t plan to give them anything quite that extreme to do.

“Good point,” I nodded. “When it is Lori’s turn to pick the dare, I will give one choice and Rachel can give the other choice. I will decide how many points Rachel’s dare is worth. It can be from zero to three!”

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