Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 14

Coming of Age Sex Story: Chapter 14 - 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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Country music was warbling on the 8-track deck in the background at a pretty loud volume. I’d never been to a party like this. This was an adult party. The kind with booze and no presents or cake. It was hard to talk over the music. I definitely didn’t look like I belonged. I definitely didn’t feel like I belonged.

The Wagners made me feel like I did though and that was important.

The song on that old 8 track was John Anderson’s Swinging. I will never forget that particular song on that particular night as long as I live. I didn’t like country music back then. It did nothing for me. John’s voice is kind of funny and almost cartoonishly southern.

There’s a little girl in our neighborhood
Her name is Charlotte Johnson
And she’s really lookin’ good
I had to go and see her
So I called her on the phone
I walked over to her house
And this was going on...

Whatever “this” was, it couldn’t have been as good as Rachel Wagner strapping herself into a leather harness that still exposed her tits, ass and pussy while her Mom prepared snacks, and her sister knelt in front of a guy and sucked his dick.

“Hey Brian, there is a message for you,” Dennis played me his answering machine after he let the girls inside. They were scurrying around preparing for the long awaited “judgment” they had all been talking about. The two guests had helped themselves to beers or whiskey and were chatting in the living room while they pinched butts and availed themselves of the Wagner’s brand of hospitality.

I had no idea who would call me here.

“Hi Brian, it’s your mom.”

I had to laugh! Of course, it was my mom calling. I liked the fact that she felt she had to identify herself on the phone in case there was another woman in the world who sounded exactly like her that might be calling me to let me know she was in Sanibel with my father. I was reminded of when Lori left a message for her father at his job. She reminded him that she was his daughter and not some other Lori Wagner.

My mother left a phone number in case I needed her. She called again and asked why nobody picked up. “It’s 9pm and nobody is home?” she sounded worried. “I hope you ate dinner. Call me!”

I had no choice but to call her. I was pretty wet behind the ears but even I knew that the implication was that I could call her to pick me up and not intrude on the Wagner’s weekend. Judgment seemed like it was important to them.

I called my parents’ room. My mom seemed relieved to hear from me but concerned it was after midnight. I didn’t even get to stay up this late on New Year’s Eve.

“It’s okay, the Wagners took me to a football game. Yeah, I ate football food,” I lied. I hadn’t actually eaten anything, but I had been super excited.

“Football food?”

“You know like at the concession stand, I shared a footlong with my babysitter.”

“They let you stay up this late?”

“Mom, their son plays for the Trojans. They were there to support him at the big game. It was great! I am fine! We won!”

“You watched a football game?” she asked. I heard my dad seem surprised in the background. He knew I wasn’t a fan of sports. I think he liked the Jets. I usually went out of my way not watch it with him. It was understandable that he’d be surprised I was suddenly a fan.

“Yeah, I am having a great time,” I replied. I don’t know what it is about mom’s and good times, but they suddenly get skeptical and often don’t want you to enjoy yourself.

“Should we come get you? We miss you,” she asked with the sound of concern in her voice.

“You are on an island!” I reminded her.

“It’s a barrier island. There is a bridge. We could be back in a few hours,” mom countered. I told her to hang on.

I summarized the call to Dennis. He told me he predicted that would happen. “It’s up to you.”

“It’s up to you, I don’t’ want to intrude on your weekend, and you’ve got this judgment thing coming up”

“I was worried about you being a pain in the ass, and you still might be, but I don’t have a problem with you coming over anytime, Brian. You tell your mom what you want,” Dennis offered. He didn’t sound like an overbearing asshole at all.

“I am fine here, Mom. I’d like to stay!”

Mom sounded concerned, and she insisted that I call her everyday and get enough rest and something to eat. She wanted to talk to Rachel next. Rachel padded into the kitchen in the nude except for her leather harness. She took the phone casually and held it up to her ear.

“Yes Ma’am,” she said. “We tried calling you earlier but you do not have an answer machine. I actually got my dates mixed up and didn’t expect him this weekend. Oh no, it’s no problem. That was all my mistake. Yes, we’ll take good care of Brian. My mom and sister say he is a delight as well. He’s been getting along really well with my older sister Lori. He’s been really well behaved. Brian is a pleasure to babysit. I’ll make sure to feed him. Should I read him a bedtime story? No? Okay, I thought I’d ask. Okay, thank you!”

She hung up the phone and gave me a wink.

Doris was naked except for a dog collar and heels as well. She was chopping up some snacks for what appeared to be a party. “We’ve got ham sandwiches, hot dogs, hamburgers. Oatmeal! What about some oatmeal? I can make you anything you want. I will be a little tied up later though.”

I agreed to let her make me a ham sandwich and watched the proceedings. Seven men arrived ranging in ages between 30 and 50 years old. They came alone. One was bald, one was fat, one was black, they were a very diverse group of guys. They laughed and pinched the girl’s asses and seemed to be well aware of what judgment was.

I wanted to ask somebody because they were talking about it but no one explained it. I assumed I’d found out soon enough.

Doris focused on bringing out refreshments and snacks. She made popcorn on the stove. In those days, microwave popcorn was available but there was nothing like Jiffy pop. It came in an aluminum foil pan that we heated up on a stove. A few kernels always came out burnt, but I always felt it tasted to superior to Microwave popcorn. There was just something about it.

I was the only kid walking around the party. Rachel and Lori looked like they belonged here but I am sure I stood out like a sore thumb. A few of the guys looked at me like I didn’t belong there, but they didn’t say anything to me.

Lori was flirting her way around the living room like the life of the party. I watched her go up to a guy and unzip his pants. Then turn around and sit on his hard dick. She didn’t even ask him. She started bobbing up and down and he put his hands around her and held her tits. Then she reached over to the guy sitting next to him and took his dick out and started jerking him off.

A guy walked up to where she was doing this and stuck his dick in her mouth. She was taking three cocks at once and she looked like she was willing to try and take more at the same time as long as they could figure where to stick it next.

Rachel was in the den. I asked her what she was doing. She had a heavy block of wood. It had four holes and was some sort of bondage device. It was pretty obvious two holes were meant for her ankles because she was already locking herself in. The other two holes were designed for her wrists. Once she was locked in, she’d be forced to bend over.

She was wearing only a red pair of heels and a leather collar. She had washed off the magic marker with her brother’s name on her ass.

“Just getting ready for judgment,” she sighed. She was bent over like she was trying on a pair of roller skates at the rink. I could see her entire asshole winking at me. It was well-lit in the den. She didn’t seem to care how obscene it looked to bend over like that. Her pussy lips were hanging down and locked up with a brass lock through both lips. They were clearly very stretched out and sore. I assumed it hurt but she didn’t seem to care. She was busy locking her ankles into a solid piece of wood that was stained just like the cages that hung in the den.

“Thanks for talking to my mom,” I said.

“I thought about telling her that you made me throw up!” she teased.

“You wouldn’t dare,” I said.

“Do you prefer me like this, or in the leather harness I was wearing earlier?”

“I think either way is fine,” I admitted truthfully. I was just happy she was asking my opinion.

She scoffed as that wasn’t helpful. “Hey, lock my wrists in here,” she begged. She had to bend over in such a way that she’d be forced to stick her ass out. Once she was locked in, she tested it out and seemed satisfied she couldn’t escape.

“Now what?”

“Now, I am a party favor and whoever wants to fuck me, can fuck me,” she said rather bluntly. The hair on the back of my neck stood up. The position she was in was so naughty and vulnerable because she was forced to expose her pussy and asshole. What made it the most sexy though was her “So what?” attitude about being fucked by anybody who showed up for the party.

“Just guests or does that include me too?”

“You ARE a guest, Brian,” she rolled her eyes. “Can you even get it up after you shot your load? That was a LOT of cum.”

I was hard as a rock again. She had no idea that I’d been practicing for this weekend my entire life. I could shoot off and less than hour shoot off again. I got so hard in the morning that I had to jerk off just so I wouldn’t have to piss through a hard-on. I found it impossible to get near the toilet when I tried to piss through a hard-on.

“Can I do it in your butt?” I asked naively. I had seen Dennis fuck Doris that way and I was now obsessed with the idea. If a girl was going to let me use her pussy that would be great, but I felt like I would be REALLY getting something if she let me use her ass!!

“I hope so, because that lock is on pretty tight,” she wiggled her ass a little and the brass colored lock in her pussy swung with it. I noticed both pussy lips were locked up. She seemed not the least bit concerned about where I put my cock. That confused me.

“How is it staying in place?” I asked as I admired it.

“My pussy is pierced, Brian. Daddy locked me up,” she looked over her shoulder at me with her beautiful doe-eyes. They hypnotized me a little. “You didn’t see all the holes in my cunt lips? It looks swiss cheese.”

I touched the lock and admired it.

“Oh, don’t do this, Brian,” she shook her head.

“Do what?”

“Fall in love or whatever. You are looking at me like you are falling in love with me. Don’t do that, okay? You don’t even know me.”

“You know me. You’ve been to my house many times,” I reminded her.

“Brian, you had no idea how I live until you got here. You don’t KNOW me. Either stick your dick in my ass or go eat popcorn and let some other guy have a turn, please. Once I start swinging, I am going to be unavailable for a long time!”

Just-a-swingin
Yeah, and we’ll be swingin
Yes, we’ll be swinging
Little Charlotte she’s as pretty
As the angels when they sang
I can’t believe I’m out here
On the front porch in the swang
Just-a-swangin!!!

I might have thought Rachel was an angel just like Charlotte Johnson if I hadn’t seen her act like a dirty little succubus. The song was starting to get to me.

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