Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 16

Coming of Age Sex Story: Chapter 16 - 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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I removed Lori’s leg restraints, and she kicked me right in the face. She didn’t kick hard, but it stung. I knew she could have kicked me harder if she had wanted to. It felt real and it shocked me!

Dennis told her she would pay for that.

“Worth it,” she grinned defiantly. That bitch! I thought she respected me after the bathroom incident. I was a joke to her as well!

Her Dad forced her legs closed and dropped her down through the gap in the table. He did it much slower this time so that she didn’t crack her neck. She still choked and gasped. She kicked her feet wildly, spasmed and seemed to have an orgasm while she was gasping for air.

Imagine how humiliating it would be to die naked in front of a bunch of a people at a party that seemed to be cheering your death.

Now, imagine instead of just being naked, you were dressed up like some hooker.

Then add to it the fact that you have an involuntary and humiliating orgasm in front of everyone while you breathe your last breath and people think it is hilarious. That’s what was happening to Lori and I have to admit – I had very little sympathy for her as well.

“You didn’t make me piss myself!” she boasted when he finally pulled her up. His arms were incredibly strong, and the pulley helped to stabilize her when he wanted to give her a break from dangling freely and choking.

He dropped her again. The John Anderson Swingin’ song was playing and people were singing along with it, cheering her suffering.

“Turn down the music,” he told someone. They didn’t want to but they did.

“Let’s hear you sing, Lori! You know the songs I want to hear.”

“No Daddy, I haven’t sang those songs since I was little!”

The rowdy audience cheered – they wanted her to hang and to sing.

He dropped her again and she gasped and screamed like it was a roller coaster ride and she just hit the big dip in the loop de loop.”

“Poopy, Poopy, Poo, titty-bopper, titty-bopper,” Lori’s song was erotic but not sexy. I have to admit, I would have been too thoroughly embarrassed to sing these things while people laughed at me! After she kicked my face, I have to admit I got a thrill when the crowd laughed at her.

Lori had a lot of courage. She played it off like it was nothing to her. I could tell she was blushing. It was fascinating to see the emotions of defiance and humiliation spread across her face simultaneously. My adrenaline was pumping. This was exciting to me – it had to be scary as hell for her!

“Coco Pops, pissy-cunty, swingin lemonade, push my button before fudge is made!” she sang.

The audience laughed at how humiliating it sounded.

“Sing it like a little girl,” Dennis insisted. He dropped her a little and let her choke.

She did as he said and he pushed her belly button. Then he left her dangling. He securely tied off the rope so that she wouldn’t choke or break her neck, but that her feet would dangle. “Sing for us, Lori and maybe we’ll go easy on you.”

“I love Stinky Pinky, dinky-dinky-doo, slurpy, burpy, pussy-farts, listen to me fart,” she pumped her elbows like a chicken flapping her wings and then pussy farted while swinging from side to side slightly. Lori’s pussy spit out some a thick, viscous pissy-squirty liquid like what was dripping on Rachel’s lock.

The crowd laughed their asses off. These were little rhymes I’d never heard yet. I don’t care how tough you are. It had to be humiliating to sing these like a baby to a big crowd while you swung naked.

“Oh, fuck off!! You’d sing too if you were up here!!” she shouted at them. Dennis was tall. He could reach her ass with a riding crop. He smacked her butt and told her to shut the fuck up and sing.

“I am a cummy, cummy, little stinky-baby, cummy, cummy, on my tummy, tummy!”

“How about you Rachel? Still think what you did was acceptable?”

She nodded yes, but looked like she was crying.

“Fine, I’ve got one for your asshole too!” he spun her so that her butt hole faced the crowd. I removed the ice dildo from its mold and handed it to him. “She used you to get out of confession. We might have gone light on her if she hadn’t done that. It serves her right that you’d help teach her a lesson.”

Dennis told me he appreciated it. He winked at me.

I didn’t wink back. I asked, “Can I stick this up her stinky ass?”

“Hell yeah!” a few people in the audience cheered me on. I walked up like I was shy. I rammed it up her ass. Her body shivered from the introduction of the extreme cold up her ass. It was so cold that it stuck on her flesh. I rubbed it around in circles. Then I punched her butt hard with a frogger punch. She spit out the dildo in her mouth in shock.

I took the dildo that had been in her mouth and replaced it with the new one from her freezer. Then I put the ice dildo from her mouth up her ass. I did it slowly. Her puckered asshole was cold and tight. She backed into it as if she was trying to hurry me. Rachel held her ass steady and let me shove it all the way up her butt as far as I wanted. She didn’t cry out or moan. Her pussy was soaked from the ice and her own juices. I could tell she was shivering and her teeth were chattering.

I knew from the lesson they gave me earlier that meant that Rachel was excited and turned on. It had to be intensely humiliating for the crowd to see that her own humiliation excited her! It excited me too!

“She needed a little change of oil,” I said. I felt like I had to say something about what I had just done. All eyes were on me. Dennis had told me to always change your oil at 3,000 miles. Dennis laughed heartily, and the crowd applauded.

Their father alternated between hanging the two of them. He particularly focused on Rachel. He made her hang with the ice dildos and alternated them so that she was always getting the last thing that had been in her butt in her mouth.

A few guys patted me on the back. One dude even offered me a beer, but I refused it. I was flattered. Beer tasted disgusting to me back then. I also didn’t want to get in trouble with Dennis.

Lori was left to sing humiliating little songs to debase herself. She frequently tried to appeal to the crowd’s sympathy, but she had made clear that she didn’t need it so much earlier that no one was inclined to relent on her.

He spent at least an hour fucking with them while Doris stood on stage naked and at attention. Doris watched strangers raid her fridge, drink their beer and nose through their house. A few of them accidentally hit her with food that she’d no doubt have to clean up later. Food that she had prepared by hand with care for their enjoyment.

I felt like that would have been torture for my mother. She would hate to see her house turned upside down and certainly have been humiliated just standing naked before a bunch of guests.

Dennis stopped anyone from being rowdy or doing anything destructive. He even made one guy leave. That guy didn’t argue or get belligerent. He knew the others in the audience would have kicked his ass. They loved Dennis and I think they definitely took his side.

Dennis didn’t need to play the belligerent ogre. He played the relatively impartial judge. Rachel had been relatively pitiful but admitted to doing something wrong. Lori had been the unrepentant brat.

What was Doris going to do?

She stood motionless and looked straight ahead, while her hands were bound behind her back. The focus was on Lori and Rachel, and she had to wait for her turn.

I didn’t think she could top Lori and I wasn’t sure she could pull off being a brat like her older sister. Rachel just didn’t look like one. Dennis set a confession she had written in her own hand on the table at her feet. The rowdy crowd turned down the John Anderson song and grew silent when they realized it was Doris’ turn.

An exasperated and bewildered expression spread across Doris’s face as she silently expressed doubt that it was fair that she was up there with her daughters.

She got down on her knees and bent forward so she could read her confession. Her hands were cuffed behind her. The noose had been around her neck all night. Dennis gave her slack so she could squat down.

“I am a dumb whore, and the mom of these two lying sluts. I was told to put together 10 infractions that I committed since the last family weekend. I did not do that,” there was already anger in the room and the crowd was upset. “I was well behaved, and obeyed my husband!”

The crowd refused to believe it and called her a liar. Somebody dumped ranch dressing dip on Doris’s head. It dripped down her face. She was helpless to wipe it off. She had to let the ranch slowly drip down her chin and licked some of it up with her tongue.

“I did raise two cunts, and I taught them to be little shit-stains,” she looked up with derision at them, as if she was on the side of the vicious crowd and felt they were justified.

Lori was singing about itty-bitty-titties and dirty big balls like a baby. Lori was shivering. She had a carrot up her ass now because the ice dildo in her butt had shattered. Carrots and apples had been severed as snacks for the party. I wondered if an apple would fit up her ass! It was so wide now that it looked like it might.

“I beg you to hang me just like my girls, for everything they did. I am the one who let them grow up to be such miserable little whores. I submit myself and promise to put on an entertaining show even if this is my last night on this earth!”

“What? You would deny OUR friends the enjoyment of judging your filthy behavior? Why not tell them about all the men you fuck behind my back?”

“They know I am a whore, dear. Admitting it won’t shock your friends. I want to hang. Please let me? I’ll sing with Lori, I’ll eat her filthy pussy, I’ll lick Rachel’s dirty ass. Just tell me what to do, I deserve it!”

She presented her pussy to her husband and begged him to stab her with all ten thumbtacks. They would have decided whether or not she deserved each one. “Put them where it will hurt the most!”

The crowd cheered! They didn’t have any sympathy for her. If this was some kind of reverse psychology by throwing herself on the crowd’s mercy it had the opposite effect.

I noticed a subtle glare between Lori and her mother. Doris offered her a wintry smile that was so slight you might not have noticed it. “We can hang together, dear! It will serve us right!”

“Please Mom! Don’t give them the satisfaction!” Lori still had hotdogs smushed in her cunt and asshole, and all over her face. She swung and choked on the noose. Lori had food and sour beer dripping on her body, and her cunt was exploding with juices running down her leg. She was obviously miserable and yet she couldn’t stop herself from having a wave of humiliating orgasms in front of everyone.

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