Keeping the Babysitter in Line - Cover

Keeping the Babysitter in Line

Copyright© 2022 by Eddie Davidson

Strut pout, put it out, that's what you want from women

Coming of Age Sex Story: Strut pout, put it out, that's what you want from women - 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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It was 1980-something and I was on top of the world. I was popping my fingers and humming my new favorite song “Strut” by Sheena Easton. “Strut pout, cut it out, all taking and no givvvvving...”

I couldn’t carry a tune to save my life, but I didn’t care. I sang it like it was my song to sing.

The pop-tune had been playing in my head for over a week and I didn’t want it to stop. I could picture my babysitter Rachel singing it when she was at my house last week. That’s when I fell in love with her and the song.

Obviously, I didn’t know what love was at the time. It was a boyhood crush, but whatever it was – I had fallen pretty hard. Rachel was my new obsession, passion, and soon to be future wife (if you had asked me at the time).

She had brown hair and a pretty face. The glasses that she wore had huge frames that made her seem like she was a shy, bookish nerdy type of girl. She was older than me by a few years but naturally I had the biggest possible crush on Rachel that a boy just entering puberty could have.

I can still see her even now when I think about her dancing around my house singing the song. It was just me and her because my parents were out for the evening. She bopped around singing in the cutest voice “I said, “Honey, I don’t like this game, You make me feel like a girl for hire, All this fascination with leather and lace is just the smoke from another fire.”

I really didn’t even know what any of that meant. I knew that a girl for hire could mean a prostitute. It also meant a girl that was paid to babysit. She was just singing along to a silly pop song, but I read so much into how she sang it that I imagined she was singing the words to me as some subtle hint that I should make a move on her.

I wouldn’t have known how to “make a move” though. It was just a term I’d heard one of my friends tell me about asking a girl on a date.

I was obsessed with girls at this point in my life (And probably still am). I had read my Uncle’s Playboy magazines from cover to cover when I went to visit him last Summer. I fell in love with the playmate of the Month. Her name was Ruth Guerri. She was blonde perfection standing like a giantess in the nude with her hands on her hips. She also seemed so far removed from my league that I knew I could never even talk to a woman like her.

Rachel on the other hand had already talked to me. Even though she seemed obsessed with Barry Manilow and was a couple of years older than me. I felt it was a far more realistic fantasy that Rachel might want to be my girlfriend.

I suppose the best way to put it is that if I was going to have a fantasy and both of them seemed unlikely to ever happen – I wanted to pick the one that was more likely than the other. If the Playboy Centerfold was being the Captain of the Starship Enterprise than Rachel was becoming an astronaut and getting to go to the moon.

I knew I’d probably never do either of those things, but I had a CHANCE to be an astronaut.

Rachel didn’t talk to me all that much when she baby sat at my house. She watched TV shows like Dance Fever with Deney Terrio and American Bandstand with Dick Clark. They were dance shows that older teenagers liked to watch.

I was more into action shows like Dukes of Hazard and comedies like the Facts of Life. I suppose I had a crush on Blair from that show as well. I kind of liked girls that looked like princesses that were a little stuck up. They seemed so dainty. I assumed girls like Blair or Rachel never farted or burped or did any of the disgusting things boys do all of the time and something about that really appealed to me.

I based part of that conclusion that I had never heard my own mother fart and assumed she simply did not have the same physical needs to pass gas that males had.

I know that some of my ideas sound silly and I freely admit they were. I need you to understand that I was a smart kid with very limited experiences in the real world. My parents never let me out after dark, my bed-time was 9pm, I couldn’t leave the block we lived on.

My entire world revolved around Spiderman cartoons and Star Wars movies and was limited to my school and immediate neighborhood. I was not only immature, but I also frequently spoke without thinking about what I was saying (and how it would be perceived) first. I had a VERY healthy interest in girls. I also had a healthy interest in Jedi powers and I had as much chance of getting the former as I did the latter back then.

I was an introvert until someone got to know me and then I blathered on incessantly until they didn’t want to know me anymore. I got bullied at school but not because I am weak or shy. I got bullied because I didn’t know how to stop running my mouth. I didn’t realize it at the time, but what I mistook for confidence was really just me frequently misjudging my capabilities and talking when I should have shut up.

I don’t begrudge bullies though. They may have slapped the snot out of me, but they also helped me understand how to stop BEING a snot. That lesson just hadn’t fully kicked in yet at the beginning of this story.

I had some good qualities as well. I loved Science, Math, Engineering and computers most of all. I was creative and I adapted pretty quickly to new information. I wasn’t a genius or anything, but I was kind of smart – and also pretty dumb at the same time, if that makes any sense.

Anyway, I already mentioned to you that the last time Rachel babysat for me she was singing Strut by Sheena Easton. She danced around my house and sang it sweetly to herself. I imagined that she was singing it for me – hinting that I should do what the lyrics in the song told me to do; “Lie down here beside me, oh, have some fun too Don’t turn away from your true vocation!”

That wasn’t the only thing she did that I couldn’t stop obsessing about! You may find it hard to believe and that’s okay with me. I haven’t told many people this story for that very reason.

I hadn’t told anyone what had happened. It felt naughty and yet she made it seem pretty mundane and totally normal.

She ran my bathwater that night. She had babysat me six times before and never ran my bath for me. However, this was the first time she was staying overnight because my parents would be home very late.

The two of just stood there in the bathroom awkwardly and waited for the tub to fill up. She added some suds to the water and splashed it around with her fingers. She was fully dressed but I remember longingly watching her bend over and admiring her butt. It was plump but not huge by any stretch of the imagination. Her butt cheeks reminded me of two pillows that I wanted to rest my head on at night.

She had no idea I was staring at her body or if she had then she didn’t say anything about it. She was so pretty that I assumed she was used to guys staring at her.

I was so shocked when she told me to get in the tub that I laughed because I thought she was joking. She just looked at me with her big brown eyes and waited. The expression on her face suggested this was no big deal to her and a very ordinary request.

Was she really asking me to UNDRESS and get in the tub? It seemed absurd and despite the fact that I was smiling from ear to ear she had a very flat expression on hers.

I removed my shirt and she didn’t say anything. I expected her to leave the room so that I could finish undressing. I kind of wished she had because I was pretty scrawny and self-conscious about my body back then. I wished I had hair on my chest but no boys my age did.

I removed my pants and waited for her to get the hint that I was really going to do it. She didn’t seem to mind. I slid them down to my to my ankles and stepped out of them. I placed my thumbs in the elastic waistband of my underwear and she looked right at my crotch as if she was getting annoyed with me.

I thought to myself “Do I dare? What will happen if she sees my dick? What If she sees my poop-hole? I best not turn around!”

Then I got completely naked in front of her and waited for a second. I guess I was waiting for her to say “Nice dick, do you want to make love to me Brian?”

I was so excited, but I tried to remain calm. I didn’t want to make it seem that I was smitten. I tried to play it off. I think she knew though.

I genuinely thought she was singing to me. I believed it was, yet another hint that she wanted me. I thought I was supposed to say some secret magic word to let her know I was one of the “Cool boys” who got to have sex with girls. I just wished I knew what that magic word was!

Yeah, I know that sounds crazy. I used to believe that girls had a secret code word that cool boys could say and if you didn’t know it then they were expected to hide their bodies from you and treat you like you had cooties. It was my way of rationalizing at the time why that kept happening to me.

“Get in the tub, Brian,” she finally said. I knew I shouldn’t have a boner, but she acted like she didn’t see how hard I was. Then she left out a towel and left the bathroom. She and I never spoke about it again.

This past week I’ve masturbated at least seven times a day to images in my head of Rachel dancing about to that song or actually soaping up my naked body to give me a bath because she is a “lady for hire”. In my fantasies she is looking directly in my eyes and signing ““Baby, what’s wrong with you? Why don’t you use your imagination?” and telling me to fantasize about her and jerk off.

I masturbated to other things as well. My parents had cable and I could make out boobs between the squiggly lines on Cinemax, but the one consistent thing had been Rachel’s pretty face singing to me about “all taking and no giving!”

My mom had just dropped me off in front of her house. My dad had even joked that I was too old to need a babysitter. I might have been flattered because I sure was in a hurry to grow up. I was just so enamored with my current babysitter that I didn’t want anything to get in the way.

My mom took my side though. “Now, don’t give Brian a hard time! He’ll mature when he is good and ready.” She turned to me and added “We’ll miss you Brian! I wish you could come with us! Maybe next time!”

My mom was the one who babied me. She was the one who thought I still needed a babysitter. I was happy to let her think that because I had a crush on my babysitter a mile-wide.

Dad kissed her (gross) in front of me and they let me out of their car with my weekend bag. They waved goodbye and blew me kisses. I was happy! Happy for them, and happy for myself. I was going to see my sweetheart crush Rachel!

I was staying Friday night, Saturday, Sunday and coming back after school on Monday. I was going to get to school with Rachel and ride on the same bus she did. That was what I was really looking forward to doing. I hoped that people would see me get on the bus with her and think we were going steady now and then maybe we really would be!

I know it sounds silly but I couldn’t wait to find out if any juicy rumors got started. I was a Freshman and Rachel was a Junior – imagine how cool I’d seem if I dated a Junior?

Who was I kidding? I would have dated an 8th grader if I could have. I had no interest in girls younger than me (back then) but they say beggars can’t be choosers. The important thing to understand is that if it could have dated anyone at that time – it would have been Rachel.

I had hundreds of crushes. I thought Hotlips was sexy on MAS*H. I had a thing for Dana Plato on Different Strokes. I even beat off to Thelma on Good Times. There was a girl in almost every class in high school that I had a thing for as well. If I had to rank all of them I would say Rachel was at the top, followed by Miss July 1983 Playboy Centerfold Ruth Guerri.

I had packed that overnight bag FULL of stuff. It was so heavy I had to use two hands to carry it. I planned to shift to one hand when I got to her door though so I’d seem strong. I didn’t bring a lot of clothes. I had everything else including some of my favorite Atari 2600 games. I didn’t know if Rachel’s family had an Atari but I was prepared. I even brought my Rubik’s Cube, my Transformers (Optimus Prime was my favorite), and some Legos. I also had about a dozen science fiction books including The Sword of Shannara Trilogy and Dune. I’d read them all cover to cover a dozen times. I assumed that Rachel read a lot (because of her glasses) and hoped she might want to borrow some of them.

I should mention that I didn’t really “play” with Toys anymore. I didn’t set them up and move them around pretending they were real people. I collected toys. I was in that awkward stage where I had just entered puberty between boy and man. I still had boyish things and interests but I was also VERY interested in girls.

I packed away some Hai Karate perfume that my mother had given me for Christmas. I’d never opened the stuff and It was a pretty big bottle but the package said that it was “Aftershave” and I wanted to Rachel to think that I was already shaving my face.

I also had a condom that I’d been saving for the last three years. The packaging was pretty wrinkled but I wanted to be prepared JUST in case.

This was the first time I was ever going to be at her house and to say that I was excited and nervous is a pretty big understatement. I was pretty confident though and nothing could get me down. I knocked on the door and rang the doorbell three times. I wanted her to think that not only was I punctual but I was also persistent.

(I didn’t realize how annoying that sort of thing was back then.)

When Rachel finally opened the door she didn’t look happy to see me at all. She only opened it part way and stuck her head out. She looked at me like I was a bag of flaming dog crap somebody had left on her door step. “Brian? What are you doing here? Did you walk all the way over here?”

“No, my mom dropped me off,” I lifted my heavy bag as if that was proof. I reminded her that she was supposed to babysit me this weekend.

“Wrong weekend,” she slammed the door and locked the deadbolt.

Well, that was a real fart to the teeth. I didn’t expect that at all. I felt like I had just been rejected by my crush even though I was ostensibly there simply so she could babysit me. I took it a little personal like she had just rebuffed my romantic advances. It genuinely hurt to have the door shut on me!

I knew it was wrong to eavesdrop. Rachel’s windows were open on her front porch. The wind was blowing the curtains a little. I could hear inside her house and I admit that I listened to what they were saying even though I probably shouldn’t have eavesdropped.

“Who was that?” I heard her mother ask. She sounded like she had a speech impediment. Her words were slow and a little slurred.

“The boy I babysit. He thinks it’s his weekend to be here, but that is next weekend,” she replied.

“Are you sure?”

“Yeah, I wouldn’t get that date mixed up with our weekend. I shouldn’t have offered to do it anyway. His mom is so sweet though and she said she wanted to have a weekend alone with him.”

That hurt as well. My parents told me they would miss me. I was feeling pretty dejected as I stood out on their porch. I had nowhere to go. My house was several miles away and I’d never been allowed to walk that far from my home by myself.

“You agreed to babysit him for an entire weekend?” I heard another woman’s voice. She sounded like an older sister. She spoke much the same way her mother did. I thought it was possible that the two women had been drinking. The older sister’s tone was bubbly and fun, but laced with a trace of sarcasm.

“Yeah, they were going to pay me 100 dollars!”

In 1984, if a teenager got their hands on a hundred dollars all at once, that was basically like a million dollars to us now.

“Well, where is he now?” the mom asked.

“I don’t know. I guess walking home?”

“Go check!” her mom scolded her.

I heard her move some things around in the house. I straightened my shoulders and tried to stand a little taller. Rachel was a little taller than me (even most girls my own age was taller than me) but Dad assured me I’d have my growth spurt soon enough.

She opened the door a little wider this time. I could see she was wearing a pretty pink blouse. She had applied a lot of makeup and done her hair very nicely. I managed to keep my tongue in my mouth and my eyes didn’t bulge out but in that moment, she looked like the most beautiful girl in the world to me.

“You can’t stay here, Brian.”

“I can’t go home, I don’t even know how to get there,” I admitted. This was all before the age of Google Maps and cell phones. If we had those I could have texted my parents and they would have just come right back. I also hadn’t had any reason to watch what streets we turned on to get to her house because it never occurred to me I might have to make my way home.

She giggled at how naïve I was and then said she would ask if she could borrow her sister’s car keys. She closed the door, locked the deadbolt and went inside.

They apparently heard the exchange just as I had heard them talking. I don’t think they knew that I was listening to them though.

“Can I borrow your car keys, Lori? I’ll just run him home and be right back.”

“Eat a sack of dicks, Ra!” Lori addressed Rachel by a shortened nickname of just Ra. Her older sister didn’t sound entirely serious. I didn’t have any siblings, but I assumed that it was fairly harmless banter.

“Watch your language, Lori! And Rachel, you were very rude to Brian!”

“Sorry Mom,” they both sang almost in harmony. They sounded half-serious about their apology.

“What about running him home on your bike?” Rachel’s mother suggested.

“That’s a great idea,” Rachel sounded exhilarated that she had a found a way to get rid of me. I heard her footsteps rapidly through her house and then she opened the garage door. She had a very large 10 speed, the kind with an oversized seat for women to sit on. “Come on, you can sit on the handlebars, and I will take you home, Brian,” she offered.

I didn’t realize how humiliating it might be to actually sit on handlebars while a girl tries to peddle her bike. I jumped at the chance and nearly knocked her over trying to get on the handlebars. I’d seen other kids do it but I had never been asked to do that before.

It was nearly impossible for her to peddle with me and my over-stuffed bag. Rachel seemed desperate to get rid of me and that made me feel terrible. I was painfully shy (around girls), so I tried not to let on that I was disappointed. I would have been happy enough just to spend time with her on the bike ride home.

Rachel seemed REALLY determined to get rid of me. That much was obvious.

“Goodness, what do you have in that bag? 100 pounds of rope and duct tape?” she laughed at her own joke. “How long were you planning on staying? A month?”

I didn’t answer her question. I was a little too humiliated. She was wearing a pair of shorts and sneakers that certainly did not go with the nice pink blouse she had on. It seemed like an odd choice but I didn’t think much of it at the time. The shorts showed off her sun-kissed legs. Rachel always had a slightly amber color to her skin that looked really sexy.

I liked watching her strain and try to pedal us both along with the bag because when she did I could see all the muscle striations in her legs.

We made it a short distance down the driveway (most of that was downhill) and to the sidewalk before I realized that I did not have a house key.

“What? How did you get in your house?”

“My mom or dad is home,” I explained.

“Yeah, but like after school when they are working? Don’t you have a house key under a mat?”

“No, why would we need that?” I was oblivious. She sighed and made me get off the bike and walk back to her house. She instructed me to wait on her wooden front porch while she went in through the garage.

When she told them that I didn’t have a house key they both laughed. I assumed they were laughing at me.

“You are fucked, Rachel!” Lori teased her.

“I wish! I could use a good fucking,” I heard her say. I couldn’t believe my sweet angel of a babysitter was actually looking forward to having sex. I assumed hot girls like that gave it out as a REWARD to people that they felt deserved it but it wasn’t something that they enjoyed themselves.

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