Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Chapter 51

Coming of Age Sex Story: Chapter 51 - 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  

I did not know that night it might be my last time fucking Rachel. If I had, I probably wouldn’t have stopped trying to fuck her.

When I awoke, she was not in her room. A sudden realization began to wash over me that this story was over. My impossible weekend had come to its natural conclusion. I was in that stage of acceptance called “denial”.

I didn’t want to accept it. I grabbed my clothes and practically ran downstairs. I wanted to see the naked family having breakfast one more time before it was all over. This weekend time had been an ally. It was one of those weekends that seemed to stretch on infinitely and I could (and have) gotten lost in replaying all of the incredible details in my mind for the rest of my life.

However, now time was fleeting. In less than an hour I would be at school, and it was all going to be over. What were the chances that I could ever arrange to be babysat again? and on a family weekend with the Wagner family?

I had matured so much over the weekend. I wondered if my parents would even believe I needed to be babysat again – probably not. I was struggling with that realization that I could not go back and be the boy I was and that meant I also could not continue to experience this wild weekend.

I didn’t want to believe that.

I didn’t even want to think about a second opportunity to do this again at that point, anyway. I just wanted to make the most of the time I had left with them.

I was naked as I made my way down the stairs. My hard dick was flopping, I hadn’t even washed off Rachel’s pussy-stank from it. I was holding some of my clothes I had grabbed off the floor on my way out the door of Rachel’s room.

My dick bounced up and down as I hustled down the stairs in anticipation of squeezing out just a few more minutes of wicked fun. What new kink or wild experience could I have in that hour? The Wagners had never ceased to amaze me with new and exciting ways to get their rocks off.

I dashed into the kitchen and noted that Brad, Lori, Rachel, and their father were dressed in typical vanilla clothes and seated at the table. They looked like any normal family getting ready for work and school while enjoying breakfast together.

I still held out hope that I could prolong things. Doris was almost naked as she stood in front of her stove making pancakes. She wore a white apron that covered her boobs and pussy. The sheer white garment was tied in the back like a butterfly’s wings and it exposed her delightful and shameless ass.

I slid on my knees across the tile floor and desperately stuck my face between her cheeks. I was fascinated by the shape of her asshole and wanted to kiss it. The heavy stainless-steel rings in her pussy clanked together like wind chimes when I slammed my face into her backside.

“Motorboat that ass,” Brad cheered. The others looked on in horror and disgust as if they had not been participants in the raunchiest orgies and sexual games all weekend themselves.

“Don’t encourage him,” Doris calmly removed my face from her ass and turned around to scold me. I was on my knees, and she stood over me waving a wooden spoon in time with her woods. “Brian, we don’t do that now. The weekend is over and you have to ask to play with me.”

“May I play with you, Mrs. Wagner?” I asked desperately – almost begged. I was in that stage of acceptance called “bargaining”. This is where I would be willing to do just about anything to rewind time and go back to how things had been the day before. I would be willing to humiliate myself and beg if that is what it took.

Doris’s blue eyes were so full of life and mischief. Yet, she regarded me with a disappointed frown as if I were a fawning child who was making a scene. “No, we had a fun weekend, Brian. It is time for you to go to school. I hope to see you again sometime,” she planted a big kiss on my forehead in the most platonic of ways.

“I understand,” I couldn’t look at anyone directly in the eyes. I felt ashamed of myself for wanting to extend things when nobody else did. “I just thought that...” I began to explain.

“Brian, if we played twenty-four-seven around here we wouldn’t get anything done. That is why we compress it all into scheduled weekends. I hope you understand. Please get dressed and have some breakfast,” Doris said before turning back to her stove.

“But, why are you naked then?” I asked. I didn’t want to sound whiny or petulant, but I think it came naturally to me back then. I am sure that my question came as an accusation that she was being a hypocrite. I shimmied into the clothes I had hastily grabbed while I was in Rachel’s room.

“I can’t wear pants while I adjust to my new piercings, so I thought I would just go au natural today. I don’t have to work and these big knockers take some getting used to,” she smiled graciously as she touched them through the material of her apron. “That doesn’t mean you can lick my asshole without permission. I might like that and keep you from your valuable public education.”

I knew she was joking but I was definitely ready to stay there and get an education from Doris that I couldn’t get in any school in Collier County.

“Do you want me to drive you to school, little man?” Brad asked politely.

He had a small two seater hot-rod of a car.

“You never offer to drive me,” Rachel groaned.

“You aren’t a guest,” Brad had his mother’s charming eyes. They glinted mischievously. He sounded so natural and confident when he offered wisecracks. They never came across crass or petulant. I was envious of how he could do that.

“Don’t deny Brian a chance to ride on the bus with Ra,” Lori interjected. She was eating with her mouth full of pancakes. She had applied her make-up and looked like she was ready for a photoshoot. Every hair on her head was styled and feathered, and you would hardly believe she spent a weekend being tortured and fucked hard.

Rachel glared at her sister with body language that suggested that Lori stop talking. Lori took that as her queue to actually continue to pull on that thread. “Don’t tell me you weren’t planning to sit next to my sister on the bus, so that everyone thought the two of you were dating?”

I doubt I had a poker face back then. I still don’t – so I think it was obvious that Lori had my number when she said that. I HAD in fact thought that the entire weekend would culminate in me sitting with Rachel on the way to school. That was a fantasy I had before the weekend began.

I wasn’t quite sure how it would all play out. I suppose in my head, I assumed if everyone thought we were dating then Rachel might want to do it for real. It sounded like the naïve plan of a kid who had no idea how the real worked when I replayed it in my mind.

Rachel blushed and looked down. She gently touched her neck.

“What? You think you covered those hickeys with make-up? Everyone is going to know Rachel and Brian, sitting in a tree, K-I-S-S-I-N-G!”

“Shut up,” Rachel didn’t lash out angrily, but she chided her sister for teasing her.

“I won’t sit with you on the bus,” I assured Rachel. I didn’t think she’d want to now that the weekend was over – so were the games of control and discipline. That had been made abundantly clear to me.

“I don’t care if you do,” Rachel added hastily. It made me feel as if all the things that had passed between us that weekend hadn’t really happened and meant nothing. I supposed that it did mean nothing to Rachel.

The experience had been a turning point for me in my journey into manhood but for Rachel – she fucked guys all the time on those family weekends, and I assumed I was merely a prop for their playtime.

I ate in bitter silence. I wasn’t angry with her for feeling that way about me. I was angry at myself for not being as cool as Brad. I thought perhaps if I had been, she might have fawned over me. Rachel wasn’t the type to fawn over anyone.

I am just telling you that at the time, I was down on myself and wishing I was cooler so that I had a different reaction. I wasn’t big on accepting myself for who I was at that time.

Brad was the first to leave. He made a smirking comment about seeing me and not wanting to be me. It was meant in jest, but at the time it hit home. I didn’t say anything back when he waved. He shrugged and left as if he was confused.

Lori informed me that she had a job at a title company. It was apparently very boring, and she felt it was pointless. “One day, computers are going to completely replace what I do for a living”

“Then you will get a job running the computer network,” her father suggested optimistically.

“ ... and be a nerd? Fuck that. I got to be a whore this weekend. I think I like it. The pay isn’t too bad, and the hours are great. Thank you for that, Brian,” she stood up and grabbed my face. She gave me a very short French kiss and offered a playful and tender taste of her tongue. I could still taste the maple syrup, eggs and butter on her breath. “If you don’t end up dating my sister, maybe you will ask me out on a date sometime.”

If I hadn’t fucked Lori all weekend, I would have believed she was patronizing me and not serious. She certainly said it like a joke but there was this hint of the possible in her offer that made me smile. I think she wanted me to smile and that may have been the only reason she said what she did. She patted me on the bottom and sashayed out of the house. “Taking the Caddy,” she said as she walked to the garage.

“After what you did this weekend?” Dennis’s tone was firm, but it was obvious that he wasn’t going to stand up and stop his daughter when she took the keys.

“Hey, you left me and mom in those drowning tubs all night long. I think I learned my lesson, Daddy!”

“No, you didn’t,” Dennis replied in his deadpan, humorless way.

“No, I didn’t,” Lori replied impishly, and winked at him as she shut the door to the garage.

Rachel and I flew out of the house when the bus arrived. In those days, you could sometimes get the bus to stop right in front of your house. I wasn’t so lucky where I lived. My mom had to drive me in the morning. All the other kids made fun of me for it. I made a mental note to talk to her about that when I got home and put a stop to it.

We dashed right on the bus. It was a different bus than the one I rode to school. All different kids and that meant that none of them knew me as “the kid whose mommy drives him to the bus stop”.

It felt liberating. I wasn’t very well known at school and so no one jeered at me or made fun of me. I also didn’t have a problem finding someone to sit with. My school bus had a popularity hierarchy and I often found that by the time I got picked up in the morning there were only about three seats where the other kid was willing to let me sit with them.

This time I felt like I had my pick of seats to sit in. It felt cool – like I was the “new guy” and I didn’t have the baggage of being seen as a puny, unpopular nerd like I did on my old bus. I was free to redefine myself. I know it was all in how I viewed myself – but at the time I thought it was the fact that nobody knew me on this bus.

“I am not going to be angry if you sit with me,” Rachel assured me as we boarded the bus. She made the statement quickly as if she would be non-plussed by it and was just being polite. She definitely didn’t make me feel like she WANTED me to sit with her.

We found an empty bench where the two of us could sit and Rachel took the window seat. I piled in next to her without saying anything.

This was the time before everyone stared at their phones. People actually talked and the bus was fairly lively. No one seemed to notice or care that I was sitting with a slightly older, pretty teenage girl. No one went “Awwww!! Wow!!!” or called it out.

I didn’t want them to do that. I suppose though in my fantasy version of how it would have all played out when I was first constructing this scenario in my head – my sitting there with her was all anyone could talk about.

Someone would whisper, “Can you believe she is sitting with Brian?” and then someone else would reply, “Do you think they are boyfriend and girlfriend?”

As far as I could tell, no one cared. I kept looking straight ahead and not saying anything. That suited Rachel just fine. She was a quiet girl of few words, and she didn’t seem to want to engage me. We stopped three more times before I got up the nerve to say something.

I planned to make pleasant conversation. I wanted to address what happened over the weekend. I was thinking about admitting that she took my virginity and made me into a man. I had so many things I wanted to say to her.

“Take your panties off,” I said flatly. I don’t know why I said that. I couldn’t reel it back in now that I said it. It reeked of desperation. I have to admit, I know why I said that. At the time, I didn’t know that I said it because frankly I wanted to keep doing what we had been doing. Even if I had a snowball’s chance in hell of being taken seriously, I just had to take my shot.

The source of this story is Storiesonline

To read the complete story you need to be logged in:
Log In or
Register for a Free account (Why register?)

Get No-Registration Temporary Access*

* Allows you 3 stories to read in 24 hours.

Close
 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.