High School Hooker - Cover

High School Hooker

Copyright© 2022 by Master Jonathan

Chapter 1

Erotica Sex Story: Chapter 1 - Cheryl had found a way to earn some extra money at school and it wasn't till I had to pick her up one day that I learned her moneymaking scheme - no wonder she was so secretive about it! But her chosen income avenue had a downside to it as well...

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft   Consensual   Heterosexual   Fiction   School   Anal Sex   Oral Sex   Voyeurism   Prostitution   Violence  

I watched Cheryl’s tight teenage ass swish back and forth as she came out of the front doors of the school and headed across the parking lot. I had come to school to pick her up because I knew how she hated riding the bus home. I can’t say as I blamed her – I was no friend of the yellow hell either. But my days of riding the school bus were a dim memory anymore. You see, I am Cheryl’s older brother and while she was a seventeen year old junior in high school, I was twenty-one and my high school days were behind me.

Mom had gone to see her sister, our aunt Tina, because her husband Steve had gotten some bad news at the doctor. Seems he had been diagnosed with cancer and while it wasn’t life threatening at this point, it upset my aunt very much. So Mom went to be with her and Dad with along too for moral support.

That left me in charge – although if you asked my sister “she didn’t need to be babysat” and was old enough to take care of herself. But both Mom and Dad knew how flightly and scatterbrained a high school girl can be, and they felt a lot better with someone a little more together overseeing things!

Cheryl didn’t know I had come to get her – it was a spur of the moment thing. I figured I’d pick her up and we’d go out and get a pizza or something for dinner before going home. It was Friday night and neither of us had to get up early the next morning.

I was just about to honk the horn to get her attention when I saw something strange. She took the arm of a boy there and headed out towards the football field!

What the hell are you up to Sis? I thought to myself as I followed along at a distance.

She was walking with this boy in exactly the opposite direction of the school bus parking area and once they got where they thought they were clear, they ducked into the team’s locker room!

Now, I had gone to this school as well and I was a fan of the team. I happened to know for a fact the team was playing an “away” game in a different town so no one would be in the locker rooms. So what was she doing taking a strange boy into them?

I followed them into the locker room and crept up to peek around the corner. What I saw nearly stopped my heart! There, through a small space between the lockers, I watched as my baby sister knelt on the floor between the knees of this boy with her back to me. Her head was bobbing up and down and he was sitting on a bench leaning against the lockers, his eyes closed and moaning in utter pleasure.

The space between the lockers offered me protection from being seen while allowing me an unobstructed view of the carnality before me. With my jaw scraping the floor and my eyes nearly popping out of my head, my little sister then stood up and dropped her white cotton panties to the floor, pulling one leg out so she could straddle the boy’s hard cock. Without taking off her far too short skirt, she sat down on the cock, and the moan that came from her audible to anyone in the locker room.

“Yes, baby! Oh God, I love your cock inside me! Fuck me, baby, fuck me good! Give me all of that big, fat cock darling!”

I couldn’t fucking believe what I was seeing. Cheryl was bouncing up and down on this guys cock like it was a pogo stick. The guy had his hands up underneath her blouse and Cheryl was covering them with her hands over it.

I stood there watching and listening to these two going at it like a couple deranged rabbits. I had never heard anyone beg to be fucked like she was. She was begging, and I do mean fucking begging, for him to fuck her!

I watched the scene unfold in front of me. If it hadn’t been my sister I was watching, it would have been a pretty good porn movie.

“Unnh ... unnh” he grunted as his hips began to thrust upwards as Cheryl dropped down. She moaned as his cock shoved deeper into her. About then, she realized he was getting close and she dropped one hand and started to rub herself.

His thrusting became more powerful and his moaning more urgent. “I’m gonna cum!” he announced, panting.

She jumped up off him dropping straight to her knees. “That’s it Billy ... cum for me ... cum in my mouth!” she urged.

And he did. He jacked his cock, wet with her juices, a few more times and then he came. Hard.

An eruption of white semen jetted out from his cock and across her face. The second shot was a little more accurate – he managed to get most of it into her mouth. After that, she put her mouth around his shaft and he proceeded to fill her mouth with his spunk. When he had finally finished, she showed him the mouthful of cum she had saved for him, then swallowed it down.

“Oh fuck, Cheryl!” he said, panting as he tried to calm himself.

“So that was good for you, baby?”

“Good ... that was incredible!”

“Well, I aim to please. Now I believe you have something for me?”

He dug in his pocket and pulled out a folded wad of bills. “$200.00 right?”

“Yep.”

He handed her the money. “Thanks, baby. Anytime you want to party again, just let me know. You were great and I want to see you again, okay?”

“It’ll have to wait till I get paid, but yeah.”

My sister, a WHORE? I couldn’t believe what my own eyes and ears were telling me!

Then Billy left and Cheryl went into the bathroom, I assume clean up a bit. I took the opportunity to back out of the locker room and make my way back to my car.

I drove home in a fog. I knew I needed to get home before Cheryl because I had the only key and she would wonder why I wasn’t home when she got there. Plus, I didn’t think I could face her or make polite car conversation on the way home. I needed a little time to think about this situation.

I was sitting at home on the sofa when Cheryl came in the house. “Hi” was all she said. Then she went to her room as if it had been any other day. She had no idea that her little “business venture” had been found out! After she changed into her everyday clothes, she came out of her room.

“What’s for dinner? I’m starving!”

No doubt ... you must have worked up some apetite! I thought to myself. “Well, I thought we could go out for a pizza if you want,” I said.

“Sure! That sounds great!” My sister was a true pizza-holic, she couldn’t get enough of it. She would have pizza morning, noon, and night if Mom and Dad would allow it. So we drove over to Mama Romano’s pizza restaurant, arguably the best pizza in town, for a couple of her delicious pepperoni pizzas.

After our dinner, we went back home and Cheryl went into her room to listen to her music. I was still trying to formulate what I was going to do about what I had witnessed.

Cheryl was Mom and Dad’s “little girl” and I knew it would kill them to learn that their sweet angelic Cheryl was a common whore – albeit a junior version, for now. No, I couldn’t tell Mom and Dad about little sister’s extra curricular activities. I would have to figure out how to handle this myself.

But I needed something to have some leverage and go into negotiations with something of value to her. It was just a short time later that “leverage” would reveal itself.

“Chris, I’m going to take a shower,” she announced. Since her and I share a bathroom, we have learned to let the other one know when we are going to be showering. And even though Mom and Dad were gone for a couple weeks, it was just force of habit anymore.

“All right,” I replied. Then I listened for the bathroom door to close and I walked cautiously down the hallway. When I got close to the door I heard the water running. Good. I knew that Cheryl likes her showers – Dad had often scolded her for taking long showers. But in this case, it was going to be helpful. I went into her room and found her purse where she always leaves it, hanging behind her bedroom door. I rummaged through it and quickly found her cell phone. I turned it on and went straight to her text messages. Sure enough, I found the conversations she’d had over the last few days and there was one from Billy about a “party” he was going to. The same party I had been witness to.

Cheryl had thrown a few of these parties over the past few weeks. Apparently, that was the code word for hooking up. I was certain this had been going on a lot longer than what her text messages showed though – she must clean them out periodically so as not to establish a pattern. My little sis was smarter than I gave her credit for!

I looked further and saw that there was another “party” set for Monday after school. It would be at the locker room as it was today – the team wouldn’t be back for a couple more days. I decided that this was my chance. I would be at the party too, hiding behind the lockers. But this time I was going to shoot a little video to commemorate the occasion, a “keepsake” that might just come in handy!

The weekend went by and I tried not to think about what Monday afternoon would bring. I hated to trap my sister like this, but I had to do something. Besides, she had done her share of evil to me growing up. She used her baby sister placemark to full advantage whenever she wanted something. Now big brother was going to show her how the game is played in the big leagues!

Monday afternoon came, and a few minutes before school let out I parked my car in a hidden spot a short distance from the football field and the locker room. I knew of a back path to the field where I wouldn’t have to cross the schoolground to get to it, and I was in position with a fully charged cell phone just waiting for the party to get started.

It wasn’t long after I heard the school bell that I heard voices, one of which I recognized as Cheryl’s. They were muffled at first, but when they entered the locker room the acoustics got infinitely better!

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