High School Hooker - Cover

High School Hooker

Copyright© 2022 by Master Jonathan

Chapter 3

Erotica Sex Story: Chapter 3 - 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  

When Diane dumped me for that other guy, I was too broken up to worry about how my sister tried to console me. At the time I thought she didn’t want to kiss me because it would feel “weird” to her – kissing her older brother even on the cheek was somehow not appropriate and even perverted. But she had sure changed her mind on what was weird now!

And I had to give it to Cheryl, she was a pretty damned good kisser. Sure, she was only seventeen and I’m sure she would hone her techniques with experience, but she was off to a hell of a start already! I kissed those sweet, full, lips and she moaned softly into my mouth.

That’s when I put my arms under her ass, and holding her tightly, I stood up, picking her up with me. Cheryl didn’t weigh much at all and I picked her up without any trouble. I played football in high school as a defensive end so I was a pretty muscular guy and I kept up my gym routine even after school ended.

Carrying my sister in a sort of reverse piggyback, I walked down the hall toward my room. I took her in my bedroom and set her on my bed.

“Now my little whore sister, let’s see just what it is you are peddling shall we? After all I should check out the merchandise I am protecting and supervising don’t you think?” I said with a smile.

Cheryl sat there on my bed, her full attention on me as I started to get undressed. Cheryl had seen me without my shirt many times. In the summer when we were at the lake or in the pool in our backyard, or when I was cutting the grass. She’d even seen glimpses of me in my boxers as I went back and forth to the bathroom. But she had never seen me the way she was about to. And I could see by the expression on her face that she really wanted to!

I made a show out of getting undressed too. I didn’t go as far as “Magic Mike” and do a striptease, but I took my time and let her anticipation build. I unbuckled my belt and unbuttoned my jeans, sliding them down my legs and off leaving them in a denim puddle on the floor. I took a step closer to Cheryl and she took advantage of my closeness to reach out and stroke the more than obvious bulge in the front of my shorts.

“Ooh, Chris...” She stroked my cock bulge and put her fingers around it to measure it’s girth and length. She looked up at me coquettishly biting her lower lips as she petted my cock.

“Can I ... see it?”

I indicated she could take off my boxers and she scooted forward smiling broadly. She took hold of my boxers and pulled them down. Suddenly my cock sprang out, surprising her.

“Oh my GOD, Chris! You are HUGE!”

I wasn’t “huge”, it’s just that most of Cheryl’s client’s were high school kids wanting a quick blowjob or hand job. Occasionally, she would get a college guy who wanted a quick no-hassle, no-committment fuck. But apparently I was bigger than most, if not all, the guys she had seen. Truth was, I sported a cock that when hard, measured seven and a half inches long and just over two inches thick. Hardly porn star material, but my little sister seemed more than impressed!

“Think you can handle it, sis?”

“I’m gonna give it a hell of a try!” she said. She licked her lips as she took hold of my cock. I stepped even closer to her and she bent her head down to my cock.

“Oh fuck yeah...” I groaned as she took about half of my length into her mouth. I watched with wide eyes as my sister began to bob her head up and down on my cock, slowly at first, but picking up speed after the first two or three up and down cycles.

I couldn’t believe how incredible her warm, wet mouth felt. I’d had plenty of blowjobs from girls I thought were more experienced than my sister, but she put them all to shame! Obviously, she had been doing this for some time – she had techniques I’d never felt before!

Cheryl slurped loudly as she expertly took me further into her mouth, making those gluk-gluk-gluk sounds just like a porn queen. Then she did something even more astounding. Without taking me out of her mouth, she slipped down off the bed and onto the floor.

She tipped her head back and swallowed a couple times then on the third swallow, she pushed down on my cock and I felt myself start down her tight throat! My little sister was deepthroating me! I nearly busted a nut right then and there, but I recovered enough to let her continue.

Watching my sister suck my cock was the most erotic thing I had ever seen. I’d watched plenty of porn, of course. I was a guy after all! But this was completely different. Knowing that it was my gorgeous younger sister, even if she was just a step-sister, was something else. I mean, I’d grown up with this girl. Lived with her almost all my life. She was the beautiful, slutty, forbidden sex goddess that I hadn’t even realized I craved.

Without removing my cock from her hot wet mouth, she reached back and pulled her panties down to her knees. She worked them over one knee, then over the other and finally completely off her and she settled back in her kneeling position. Spreading her legs wide, her hand slipped down between her thighs to the smooth pink folds of her pussy. I could see her hand as she rubbed up and down, teasing her slit and she kept sucking my cock.

After another few moments, Cheryl sat up and back onto her heels. “I think you’re ready now ... your cock’s nice and wet!” she announced. “I know I am...”

I held out my hand and she smiled up at me, placing her small delicate hand in mine. I helped her to her feet and then I held her out at arm’s length to look at my now completely naked little sister.

“Damn, Cheryl ... how did you get so fucking beautiful? And how did I miss it!”

She blushed at my words. “Aww, thank you, Chris. I can’t tell you how much it means that you think that. Now how about giving your little sister a ride on that thing?”

“Get up on the bed then my little whore and let’s see if you are as good as you advertise!” I said giving her ass a playful swat. She squealed happily and climbed up onto my bed.

“So what can I do for you today, mister?” she said, acting like I was just another of her clients.

I played along with the ruse. “Well I heard tell that you have a nice hot pussy. But I want it from behind so get up on your knees and show me that tight little ass!”

She got into position and I moved in behind her. But before I started fucking her, I wanted to warm her up a bit. I started fingering her wet little slit just running my fingers between her swollen, puffy lips at first, then moving a bit deeper to run them around the rim of her entrance. I knew a little about teasing myself and now it was my turn to make her moan and wriggle.

She whimpered softly and tried to push her ass back at me, wanting my fingers deeper in her, but I moved with her keeping myself for giving her what she wanted. My teasing touch began to work on her and her whimpers got louder and more desperate.

“Please Chris! Please don’t tease me! I want to feel you inside me! Please!” she pleaded.

All right ... if that’s what you want, sis... I thought to myself.

I thrust two fingers deep into her, curling them downward and around her pubic bone to rub that pleasure spot commonly known as her g-spot. At the same time my other hand went under her to rub back and forth against her clit. With both hands furiously working her right from the start, she wasn’t expecting it and she gasped.

“OH FUCK CHRIS! OH MY GOD! OHHH, SSSHIIITTT!” she cried out. My fingers inside her were like a runaway jackhammer and my other hand flew back and forth across her clit just as rapidly. Cheryl instinctively tried to crawl away from my tormenting hands, but I grabbed her thighs and pulled her back only to resume my work. She laid her head and chest down flat on the bed hoping that would help, but I simply moved with her, pinning her to the mattress as I kept working her.

“Oh my God! Oh my God! Ohhh, fuck!” she cried as I continued churning my fingers in her sopping pussy. She raised her ass higher as her first orgasm with me got closer. I could see her legs quivering as she strained to fight it. But it wasn’t going to help – I was going to make her cum ... and more than once too!

I kept the pressure up on her and soon she realized she was not going to win this contest. With a scream “OH MY GOD, CHRIS, I’M CUUMMINNNGGG!” she did exactly that. She poured her sweet juice out in a torrent all over herself, me and the bed under us. I kept doing what got her here even as her orgasm raced through her. She screamed, she twisted, and writhed, but I didn’t relent until I was sure her orgasm was passed. She lay on the bed face down, panting for breath.

But I didn’t let her rest for long. Pulling her back up to her knees, I unceremoniously shoved my hard cock deep into her still-quivering pussy fully.

She screamed out again. “OH GOD CHRIS!” and I knew that she finally realized what being a whore was all about! My cock was indeed bigger than anything she had felt until now and she was being stretched like never before. I was also deeper in her than most of her “clients” could reach so this was a whole new experience for her.

“What do you think of ‘big brother’ now little sister?” I said as I slammed into her again and again.

“Oh, Chris! Oh fuck, your cock ... oh, its so big! It’s stretching me ... so wide! Oh, I love it ... I love you! Oh, shit! Ohhh...”

I fucked Cheryl hard and fast, not taking it easy on her. I didn’t want to hurt her, but I figured if she wanted to act like a whore, she’d better get used to being ridden like one. Actually, my intent was to try and show her that being a prostitue was not an easy life and try to persuade her to find another way to earn money besides on her back.

I understood that she liked sex and the money seemed good. And God knows she was built for the job. But those spectacular looks would not last forever and the money she made doing this came at great risk.

Sure, I could protect her from getting beaten up, robbed, or raped, but even with me watching over her, I couldn’t prevent such things as STD’s or an accidental pregnancy. And either of those eventualities would then lead to a very awkward dicussion with our parents!

I could feel myself starting to get close to my own orgasm but I was far from done with my little sister-whore. I was going to fuck her every whichaway until she was completely exhausted – too weak to do anything but lay there panting, a sweat and cum dripping mess.

To that end, I stopped fucking her for the time being and got up off the bed. She was still trying to catch her breath from my fast-paced fucking when I spun her around and flopped her over onto her back. Then I pulled her towards me until her head dropped over the edge of the mattress.

I stepped forward, straddling her head and pinning it between my knees and pushed back against the mattress. She couldn’t move her head in any direction. I reached forward and grabbed a nipple, pinching it hard until she opened her mouth to scream. Only I plugged it with my cock before she could.

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