Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 6

Coming of Age Sex Story: Chapter 6 - 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  

Dennis prepared on this end of the yard for the race as well. He handed me some bottles with nozzles and told me to fill them with the garden hose and then seal them tightly. The bottles looked like clear ketchup bottles to me. I assumed they were water bottles for the participants to drink in case they got thirsty. Kids used to drink from the garden hose back then and thinking nothing of it.

Dennis started futzing with the large stones and bricks near the grill.

Everyone could hear the “Dooga-dooga, dun-dun-dun” the mighty drums of the Lely Marching Band performing at the Football game pep rally from miles away. You couldn’t hear any of the other instrument. The thunderous cadence of the percussion beats were building up excitement for the game to come.

The drums weren’t for us, but they kind of felt like they were. I found myself bopping my knees to the catchy little beats and shaking my rump. I saw the girls do it too.

I had never been to a Football game in High School because I had no interest in sports. The only sports I would have played were Football on the Atari 2600.

That video game was considered THE state of the art sports simulation at the time. It consisted primarily of three little flesh-colored men against three little gray colored men performing little football plays on a top-down football field.

“Sorry Daddy,” Rachel skidded into the lawn first. She spun around and presented her ass to her father as if she had played this game before and knew the starting position quite well. She went down on one hand and knees, much like a running before starting a sprint. The others joined her and lined up in front of their respective lanes facing the stools they had placed at the other end of the yard.

The dildos were now planted firmly on the stools. They waved slightly like tiny little flags or goalposts in the distance. I would say it was only about thirty yards.

“Judgment tonight?” Mr. Johnson joined us.

“You always seem to know when our family weekend is,” Dennis sounded a little coy in his response.

“Hah, it feels like you do it every weekend,” Mr. Johnson replied.

“I wish!” Lori replied brightly. She bounced up and down slightly. The bells were still clipped to her pussy and the mousetraps still hung from her tender nipples. She looked positively obscene, but Mr. Johnson had obviously seen her like this before, or he was simply unflappable.

“We used to have them a lot more frequently, but now we just have so many things going on,” Doris added.

“The rules of the game are simple, and you’ve done this one before,” he told them as he went down the line and reached under their legs. He attached a clip to their clits and then ran a length of chain around their hips. The other length of chain was attached to a heavy brick.

“You simply have to run to the other end of the yard, sit down on the dildo,” he paused and clarified that he expected them to sit down all the way and not just take the tip. “Then you may release, run back, fill up again and do it all over. You’ll do three laps, and the winner takes all.”

I had no idea what he was talking about. What did he mean by fill up? The participants seemed to understand and he wasn’t talking to me.

“The winner gets to decide what you three will wear tonight to the football game. You have to keep it street legal. No panties, no bras, no slacks, no shorts, nothing see-through!”

“Bikinis?” Doris asked brightly. I was shocked she was gung-ho about the game. I assumed most mothers wanted their daughters to dress as conservatively as possible.

“They are fair game, but whoever picks the outfits has to explain why someone in our family wore one to a football game if anyone asks,” Dennis said. He unceremoniously and without warning jammed one of the bottles between his wife’s butt crack.

She seemed surprised, but not alarmed or even concerned. Dennis stuck the bottle up Rachel and Lori’s ass as well. I was surprised to see that the water was slowly seeping into their bottoms.

“If you drop your load before you drop on the stool, you’ve got to come back and start over,” he informed the ladies and they groaned.

“Are you going to use the bazooka on them?” Mr. Johnson asked. He was at least ten years older than Dennis. He looked like an intelligent man, but not a sadist with a death wish. Did he really mean to use a WWII Bazooka in his yard? At that point in my life, I immediately thought it was entirely possible with the Wagners.

“Why not,” Dennis reached into the chest with his garden tools and removed what appeared to be a modified gas-powered leaf blower (we didn’t have electric ones in those days). There was a reservoir of green tennis balls attached to the side. He handed it to Mr. Johnson and told him he could do the honors. Mr. Johnson was more than happy to pull the cord and start it up. It sounded loud, powerful and a little intimidating.

It took a full five minutes for the water to finish settling into their bowels. The girls talked amongst themselves. I was surprised that the men talked about Football.

“Who do you think is going to the Superbowl?”

“I think the 49ers have a chance with Joe Montana,” Dennis answered as if this bizarre game was quite mundane.

“I think the Dolphins could go all the way,” Mr. Johnson replied. The two men conversed as if the race they were watching was a perfectly normal thing for a family to do on a Friday afternoon.

“Oh, in the AFL? Shula is the man, but I am a Bills man,” Dennis said. They may as well have been talking in Ancient Greek. I had no idea what they were discussing.

“Oh, one more thing,” Dennis seemed to be waiting to drop another shoe. The girls were already groaning in agony as their asses filled up with water. (I had never heard of an enema before that day and had no idea how uncomfortable it was to have to hold one). Their tummies were starting to distend and fill up. It made them look slightly pregnant.

“There always is,” Lori offered a wisecrack. She seemed amused by the rules of the humiliating contest.

“You’ve got to sing IT three times before you can release, and three times before I’ll give you another enema!”

I didn’t know what “it” was. I assumed it was the “pretty pretty please” rhyme from earlier.

“Are you going to actually push our buttons?” Lori asked hopefully.

“Mr. Johnson’s on the Bazooka, and I’ll be down here on dookie patrol. Are you up for pushing their buttons?” he asked me.

“Daddy, he doesn’t know how we play the game,” Rachel offered. Her tone suggested that she didn’t want me to play either.

“It’s so simple, even a dumb cunt like Rachel can do it. They are going to sing a little song. Don’t let them start singing until their thighs are touching wood completely and you don’t see any more dildo. You just push their belly button at the end and WHATEVER you don’t stand behind them.”

I was eager to participate. He patted my head and told me to hustle down to the other end of the yard. “Faster, wagon wheels,” he yelled because I was jogging and not sprinting. “Oh, and Mr. Johnson is going to be firing the bazooka. Try to dodge if the balls come at your face! I know my girls won’t.”

I was so excited to be a participant that I didn’t care how insulting he was. He didn’t seem entirely serious when he made fun of me anyway.

He shouted, “On your cunts, on your tits, on your asses, and GO!”

The girls got off the ground and began to run, but it was like they were caught in a slow-motion time warp. I couldn’t tell at first, but I realized as they approached and strained with effort that they were dragging heavy bricks clipped to their pussy flaps.

Rachel’s singularly long cunt flap made a lot more sense to me now. I wondered if she’d distended it in a prior race! I winced in pain imagining pulling a brick with my dick. I could imagine it sticking out behind me like some prehensile tail, tethered to a heavy 5 pound brick as I dragged it across some Saint Augustine grass.

The girls were gritting their teeth in anguish and groaning as they pushed themselves ever forward. Their tits flung before them as they bent over slightly and pushed their shoulders out in front of them.

“Come on slowpokes,” Rachel teased her sister and mother. She rarely made wise-crack comments.

“Slow and steady wins the race, Rachel,” Doris said.

Just then the first of dozens of tennis balls went flying at them. I don’t know how fast or hard they were being fired out of that leaf blower. it seemed to me to be very frightening, but the girl’s accepted the risk like soldier’s storming Normandy beach. The first one hit Doris squarely in the back.

Instead of turning around and shaking her fist. She simply cried out like a wounded soldier and kept slogging forward. The torrent of tennis balls was steady and the neighbor was aiming for their asses.

He also fired a couple at me that were near misses. I have to admit that I was scared and my adrenaline was pumping. What if he hit me full on in the face?

The girls didn’t try to zig-zag or dodge. They traveled in a straight line like lemmings heading toward the proverbial cliff to fall off. They gritted their teeth when they were struck by the ball, but they did not tell the men to stop.

Why were they playing such a cruel game? And how was it fair the men didn’t have to do it as well?

“God damned it, I can’t hold it,” Rachel closed her eyes.

“You can do it, Rachel!!” Lori offered supportively. I was initially surprised that even though they were competitive, they also seemed to be rooting for one another.

“Shut up, you bitch!” Rachel offered playfully. “You have a higher capacity asshole than I do.”

The first one to reach the stool was Lori. She smiled triumphantly and spun around to face her father’s side of the lawn. She straddled the dildo and sat down on it. The chains on her pussy flaps holding the brick didn’t prevent her from sitting on it. At first, she sat only on the cock head.

Once the hot blonde got her vaginal wall around that, she slid down to the mid-way point and looked very happy. Then she took the other end.

Lori, you slut!” her mother still had several feet to go.

Lori waved me over and began to recite “Poopy, Poopy, Coco Pops, Lemonade, push my button before fudge is made!”

I didn’t even register what she said or how hilariously humiliating it must have been to recite it to be the first time around. I almost pressed her belly button, but she stopped me and held up two fingers.

“Poopy, Poopy, Coco Pops, Lemonade, push my button before fudge is made!”

This time I smiled. I even chuckled. I know it sounds silly but imagine an extremely hot, naked girl, nineteen year old girl dancing in place singing this song to you. It really had to be one of the most humiliating things I’d ever seen anyone do.

The funny part was Lori was half-smiling as well.

The mouse traps on her tits jiggled in time to her own laughter as she recited the dirty phrase for me. Her father probably couldn’t even hear his side of the yard. I had no idea how they would have run this race if I hadn’t been there.

“Poopy, Poopy, Coco Pops, Lemonade, push my button before fudge is made!” she waved me to her tummy with a sense of urgency as I laughed. I pressed her belly button like she was some silly Teddy Ruxpin doll for children.

Instead of telling me a bed-time story, she slid up on the dildo ever so slightly, stuck her butt out, and brown water SHOT out of her ass all over the hedges behind her.

I was so shocked that I couldn’t even be disgusted. The water didn’t even look like poop. It looked like pure milk chocolate and that probably made it seem appealing. I believe though the fact that she performed an act that I had previously considered so private and taboo in front of me BECAUSE I had pressed her belly button that I now felt as if I had participated in the act myself with her.

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