Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 9

Coming of Age Sex Story: Chapter 9 - 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  

Woman dressed in a short red skirt, lifting her foot onto a guard rail, and showing her panties

I was proud of myself for asking what Dennis considered an “interesting question.” I thought perhaps they simply hadn’t thought about the risk to Rachel’s reputation. I was wrong, obviously.

“Brian, my family, enjoys what is called predicament bondage,” Doris began. “It isn’t for everyone, but it has an element of danger and risk to it. She went on to explain that it involved being brought to physical exhaustion through cages or having heavy weights attached to their bodies. There is a visceral reaction to being brought to the point of exhaustion through restraints. There is also an element of excitement to being caught or humiliated which creates powerful emotions and sexual responses”

“Did you understand any of that?” Lori asked rhetorically. “Did you watch Nightmare on Elm Street or Friday the Thirteenth?”

“Yeah,” I replied.

“Did you like it?”

“Yes!”

“Were you scared?

“Yes!”

“Did you watch the movie and identify with the chainsaw wielding maniac chasing the pretty girls around the showers or did you identify with the people scared for their lives who were trying to survive to the end?”

“The survivors,” I assumed everyone identified with the plucky college kids just trying to find a way to safety.

“Did you think any of it was really real and that anyone actually died on the set?”

“No, obviously not,” I thought that WAS a dumb question. It was just play-acting.

“Okay, we like being scared too. We get off on it. We don’t just like to be scared. We liked to be terrified. A little scare isn’t enough. Daddy, likes being scary. It lets him blow off steam. This weekend is like living in a movie. You know it’s not real, and at the end of the movie you are going to leave the theater safe and sound, but you get to have an adventure. We can’t just do this all the time though. I have a job now. Once a month is enough, just like a period.”

“I am so glad, I could be your fantasy tampon to be used once a month, Lori,” Dennis chuckled.

“You are appreciated, Daddy,” she teased back.

Wow, suddenly a light bulb went off over my head. I was getting it but I still didn’t fully understand. “Okay, but do you really want to wear that sweater?”

“No, but I’ll get arrested if I take it off,” she smiled and popped some gum.

“Okay, but if you want to dress slutty then wouldn’t you rather just choose your own outfit?”

“I can do that any night of the week, Brian.”

“You do DO that,” Doris reminded her daughter with a half-laugh.

“This is just for fun, don’t read too much into it,” Lori summarized her mother’s point. Then she laughed about how it sounded like Doris said “Doo-Doo.”

I couldn’t help trying to make sense of this and read into it. This was the single most bizarre and interesting thing that I had ever seen in my relatively short life. I still had a nearly infinite number of questions without any answers. The ones that were answered created even more questions to follow up with.

“That still doesn’t explain why you would make Rachel dress like that at the game if you are concerned about her reputation?”

Lori blew a bubble and thought about it. “I fucked anybody I wanted in school. If they didn’t want me, that made me want them more. I liked to go to a party and BE the party. I had no fear and I still have no fear. I don’t have any regrets, and I’d probably do everything the same fucked up way if I had it to do over again, Brian.”

I listened as she thought about what she was saying. She kicked the back of my chair with her heels nervously. “Bending over and pretending you didn’t realize you forgot your panties at the food court is probably going to get somebody to crack a smile. Dressing a little trashy or do something a little daring isn’t that big of a deal, Brian. You should try it some time, be a little less uptight.”

We rode in silence for a little while. The song Strut came on the radio in the background. I smiled because it was my new favorite song.

“You could probably tell your best friend in the whole world what you saw us do today in the backyard. He’s never going to believe it anyway.”

“I’d rather you not tell anyone,” Dennis corrected.

“Yeah, but even if you did, he’s going to say that you are making it up. You saw my asshole. You heard me sing the poopy-poopy song and I begged you to press my bellybutton to let me take a shit. So what?”

“Where did that idea come from anyway?” I changed the subject.

“When Lori was little, she used to sing all these dirty little rhymes,” Doris sounded proud as she reminisced. “She’d make her little brother beg to go poopy. “Soon, I was making Brad sing Poopy, Poopy, Coco Pops, Lemonade, push my button before fudge is made! He loved to please and he wasn’t shy. I’d press his belly button and he’d giggle like the Hamburger Helper glove. It was adorable.”

I couldn’t picture that mountain of a boy ever being a baby.

“We just sort of fell into the habit. If anyone sneezed they had to sing ‘Easy-Peasy, Lemon-Squeezy, if I sneeze, grab my booby’ or she’d grab their boob and twist their nipple.”

“Itsy-bitsy titty twistee,” Lori giggled.

“Do you have others?” I asked.

“These amuse you, don’t they?” she giggled impishly. It seemed like the songs amused her as well.

“Yeah,” I had to admit they did.

“You could have made us use baby voices, or talk like Donald Duck,” she told me that I could have specified that when I was pressing their belly buttons.

“Could I have made you talk like Darth Vader,” I held my hand over my mouth, and breathed heavily into my hand with an ominous tone like Vader did in Star Wars.

“Who the fuck is that? He sounds like he has asthma. Yeah, you could.”

“Do it now,” I said.

“I don’t have to take a crap,” she assured me that she wouldn’t for a long time and that her ass was entirely cleaned out.

“Don’t let Lori kid you,” Dennis said that his daughter was always full of shit and always would be no matter how many enemas she got. That was the first time I heard that word. I assumed (correctly) that it had something to do with the bottle of water up their asses and the act of holding the water in.

They told me what they were singing to Dennis at the other end of the yard. I didn’t know until that moment. It sounded really hot.

Lori told me another one that she uses. “If I beg Daddy to let me shit and he wants to walk me out on the lawn like a dog, he’ll make me say stinky pinky has a fat ass, Please let Stinky Pinky pass! if I beg, if I plead, if I crawl, will you lead?”

“What about Wibble wobble, black bobble, wibble wobble out! Turn my filthy pussy inside and out, one of its dirty, twice if its clean, Wibble wobble, black bobble, wibble wobble out!” Rachel asked as she enunciated the tongue twister expertly.

“Oh, we haven’t done that one in years. Can we use that this weekend, Dennis?” Doris sounded delighted.

“It’s too long. I like to hear you repeat it,” Dennis decided.

“I still don’t understand why you like it when he makes you do something embarrassing?” I asked.

“Do you want to try it?” Lori asked.

“No!”

“Chicken?” Rachel asked.

I was really shy about it. I just wanted to understand it.

“Brian, imagine that I am blind,” Doris said. “I’ve been blind since birth. Describe the color green to me.”

I couldn’t do it. I tried to bring up things that were green but obviously someone who had never seen a tree or the color green would have no frame of reference for comparison. I tried to use word pictures but I couldn’t.

“Now, imagine that three blind people are feeling up a woman,” Dennis said that they’ve never seen a woman. “They try to describe what a woman is like but since each one has a different body part, and their experiences are limited to only that part then they have only a limited understanding.

“One blind man had his hands on her tits. He describes women as having jugs swollen with milk and says that you can turn them on by playing with their nipple. The next man disagrees. He has his fist in her cunt. He says that women smell like tuna fish, and they get turned on when you twist your hand around inside of them. The third man says that he doesn’t know where they got this from. He sniffs his finger and says that women smell and taste exactly like shit because his finger has been up her ass.”

I thought Dennis might be joking. Everyone groaned because they had heard Dennis joke before.

“It gets better every time I tell it,” Dennis assured me to wait a month and he’d tell it again and that time I’d laugh for certain

“It’s a corny joke about a group of blind men who have never come across an elephant before and who learn and imagine what the elephant is like by touching it. Each blind man feels a different part of the elephant’s body, but only one part, such as the side or the tusk. They then describe the elephant based on their limited experience and their descriptions. It’s meant to remind you that until you have felt the ENTIRE elephant you won’t know what part you like best. As a blind person, you don’t even know what parts you are still out there haven’t even touched yet. I’ve touched a whole lot of parts and I know that I like to be humiliated. It’s fun, and it is terrifying and perfectly safe.”

Things were making more sense to me, but I had a lot to learn. When we arrived at Lely High School it was dark out. The parking lot was already full as so many people had arrived ahead of us.

I walked with them to the big game. I could already hear the fans cheering in the stands. It was very busy out. There were lots of cars and honking in the school parking lot. Many people were just riding around the parking lot to be seen and look for friends or pretty girls.
Teachers that I had seen during the day at school were standing around directing people to the ticket office and the concessions.

“Are you going to remove our handcuffs, Daddy?” Rachel asked as she walked with her sister. She kept her hands discreetly behind her back.

“Oh, did I forget?” Dennis smirked as he stepped up to the ticket booth.

“You guys would really let me try things out?”

“Sure, do you want to grab the elephant’s nuts, or his mouth first?” Dennis laughed at his own joke. “I don’t have an extra set of handcuffs with me, but you could walk with your hands behind your back for a start.”

“I was thinking I would like to do the bad guy stuff?”

The girls looked at me with churlish grins on their faces. I think they saw me as somewhat harmless and a bit too nice for that.

Dennis ignored me while he pulled out his billfold and paid for the tickets, including mine. The awkward silence was killing me. “I don’t know how much you are making babysitting this kid, but his ticket just came out of it,” he addressed Rachel as if he hadn’t even heard what I said.

I was feeling very dejected. I guess I expected a triumphant four-piece band to give me a big huzzah in the background while Dennis handed me the keys to the handcuffs and told me the secrets of being the boss. That was probably pretty unrealistic.

The football field was around the side of the building. It was just a simple outdoor football field. It wasn’t particularly much but there was a lot of activity out front. It was dark outside and there was a throng of people outside.

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