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High School Hooker CH 1 Part 2

"His slutty sister has a secret business... and he likes it!"

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8.0k words 8.0k words

Author's Notes

"This is the second of four parts that make up the complete first chapter. Enjoy!"

"Thank you, baby!" she said and kissed his cheek. "Guess you weren't lying when you said you were paying double today..."

Rob just shook his head 'No' and started pulling at his semi-hard penis. Kara tucked the money into her purse then turned her focus to him. She looked ridiculously hot. She was wearing a red top that pressed tightly against her body. It tied together behind her neck, showing off the smooth skin of her arms and shoulders. With it she wore a pair of thin white capri pants. They hugged her ass nicely even after she had unbuttoned them before starting to make out with Rob.

Kara took Rob's cock into her hand and started stroking it for him. She looked down at it and released a long strand of saliva from her mouth, letting it drip onto his dick. She spread it around the head and shaft with her delicate fingers before starting to jerk him off. Rob closed his eyes and moaned, enjoying the sensation of my sister's little hand jacking him off. As much money as it looked like he had given her, I knew he wasn't just there for a handjob.

Sure enough, after just a minute or so she sunk her head down and took his cock into her mouth. She immediately started power sucking his throbbing tool. Her hand stroked the base as her head bobbed up and down, taking half of his cock into her mouth each time. Rob reached up and pulled the knot loose on her top. The two straps fell down and she unsnapped the strapless bra she wore beneath it. Kara quickly pulled it away, revealing her perky teenage breast.

As Rob reached under and squeezed one of them she turned her head, taking him out of her mouth and ran her lips down the side of his shaft. Then she looked up and right into the camera. Smiling as she rubbed his cock against her lips, Kara winked.

There was no mistaking it. She winked right at the camera. Right at me. She obviously knew I was watching and was teasing me. She was putting on a show for me, her big brother.

She turned and engulfed his cock once again, this time taking him all the way in until her lips were pressed against the base of his cock. She was deep throating him with long slow strokes. Her lips drug along the skin of his erection as she took him into her throat over and over.

"Ohhh fuuck..." Rob groaned from the pleasure.

She continued like this for just a few more minutes before sitting up on her knees beside him. She kicked her feet out and pulled her capris down her long legs and off, tossing them aside onto the floor. She wore a tiny white thong beneath. I watched as my sister lay back on the seat and rubbed her pussy while looking at Rob.

"Well? Come on... I believe your text said that you were going to 'fuck my brains out until your cum was dripping out of my cunt...'" she challenged.

"Damn right, I am!" Rob said as he climbed between her legs into a missionary position. He planted his hands on either side of her head, holding himself over her thin body. Kara reached down and grabbed his cock, lining it up with her pussy while she held her panties to the side with her other hand.

"Unh!" she moaned when he pushed forward, shoving his cock halfway into her. He pulled back then slammed forward again. After another thrust or two he was fully embedded within her tight folds and he started slowly thrusting in and out of my sister's pussy.

He continued like that for a couple minutes. Slowly pushing his pelvis forward and burying his cock into Kara's pussy.

"You call this fucking my brains out?" Kara smiled, urging him on.

"Alright... you asked for it..." Rob replied cockily.

"I'm just holding you to your word... UGH!" Kara squealed as he thrust forward with as much force as he could. Slamming his cock to maximum depth. Just as quickly, Rob pulled out until only the head was still inside her and shoved forward again. He quickly worked up to a fast pace. His ass bouncing up and down between her legs as he pounded his cock into Kara's pussy again and again.

I could feel my cock straining in my pants. I contemplated taking it out and relieving the pressure, after all Kara had brought me out here to watch hadn't she? But I couldn't do it. I still didn't know what her purpose for bringing me was. Did she want me to jack off again while watching her get fucked? Did she just need me to use the tablet to record her? The last thing I wanted was to misread her intention and piss her off again. So I kept it in my pants and just watched.

Rob hadn't let up yet. He was absolutely railing my sister. Her tits bounced up and down as he thrust forward over and over. I could see his ass clench each time he pushed forward, making sure to bury every inch he could into her. He kept that pace for several minutes.

"UGH! UGH! UGH!" Kara moaned throughout it, obviously enjoying the rough pounding she was receiving. Finally, she pushed forward on his chest. "Off real quick," she instructed.

Rob pulled out of her and sat back on his heels. His cock standing proudly out in front of him and glistening in my sister's juices.

Kara rolled over and climbed up on her knees. Pointing her ass back toward him she looked back with a grin and shook her ass in invitation.

"Fuck me from behind..." she ordered.

Rob eagerly moved into position. He grabbed my sister's ass and lined his cock up between her pussy lips once again. Rob's focus was completely on the round teenage ass in front of him as he sunk into her pussy. Kara however, was looking right at the camera. Her grin contorting into look of pure pleasure as she closed her eyes, enjoying the feeling as Rob's dick stretched her pussy once more.

He didn't start slow this time, immediately ramping his pace up to full speed. With both hands gripping her hips, he pulled her back against each thrust.

"Ah! ah! ah!" Kara squealed each time his cock reached full depth. He was pounding into her. He reached up and took hold of her wavy blonde hair, pulling back on it while he continued to fuck her.

"Oh yeah... oh fuck me, baby!" she cried out.

I could see Rob's face start to tighten. Sweat was dripping from his forehead as he continued to thrust in and out of her. It was obviously getting to be too much and I could tell he was gonna blow soon.

Kara could tell as well. "That's it, baby, fuck my tight little pussy... fill my fucking pussy up so you can watch your cum drip out!"

Her filthy words sent him over the edge and with a loud grunt he held himself inside her.

"UGHHHH... UGHHHHH..." he groaned as he released his cum into my sister's unprotected womb. Kara remained helpless in that position, her neck craned back slightly as Rob kept his grip on her hair. Her chest pressed forward and her hard nipples protruded out. Her eyes were clenched shut while she appeared to be having a small orgasm of her own. I starred at her as her body shook in place while she focused on the cock inside her, filling her with sperm.

Rob finished off his orgasm with one then two final thrusts before pulling back and sitting onto his haunches. He let go of Kara's hair and reached down to squeeze her ass.

Kara leaned forward, resting her forearms onto the seat. She lay forward, her chest flat against her arms but her ass still perched up in place. I couldn't see it from my angle but apparently Rob actually was watching his cum start to drip out of her pussy.

"Emmm... feels like you made quite the mess back there, hun!" she teased.

"Told you I wasn't lying..." Rob smirked.

Before any of the cum could drip onto her clothes, Kara pulled a wipe out and began to clean herself up. Rob wiped himself down as well and pulled his pants back on. With a quick peck on the lips he climbed out of the truck and shut the door behind him. Kara sat up in the seat, still naked from the waist down and her tits on full display.

"Good show, Bri??" She smiled and giggled cutely, then began to put her clothes back on. My cock was still raging hard as I watched her first put on her bra and retie her shirt. Then she pulled her panties back over her pussy, having never actually taken them off. And finally she pulled her Capris back on.

When she was done, Kara climbed out of her truck and came over to mine. I rolled down the driver side window as she walked up.

"So? What did you think?" she asked. She looked at me with what seemed like real curiosity.

"I... uh... I'm not sure..." I could hardly form a sentence still.

Kara leaned into my truck and looked down at my lap, smiling when she saw that I was still mostly hard.

"Well, seems like someone else is sure that he liked it," she teased. Then a look of seriousness came over her. "Wait! You didn't jack off this time, did you??"

"No!" I answered a little too quickly.

"You sure??" she looked at me quizzically. I was so thankful that I had chosen not to. I knew that she would get pissed and think I was a sicko if I had.

"Yes, I'm sure. I learned my lesson. I'm not gonna do that anymore while watching you, I promise."

"Hey, I wouldn't go that far," she said.

"Huh? What are you talking about?" I was confused.

"I just didn't want you to do it THIS time. I forgot to tell you before, though."

"I don't understand..."

'KNOCK KNOCK KNOCK'

I jumped in my seat at the sudden knocking coming from my passenger side window. I had been so focused on Kara that I hadn't been paying attention to my surroundings. A teacher must have somehow seen us and came out to investigate.

Luckily, when I looked through the window it wasn't a teacher. I was still shocked however to see the gorgeous brunette standing beside my truck. I hit the button to unlock the door. She opened it and waved cutely when she saw me.

"Hey Brian!" she greeted.

"Umm... Hi Lilly..." I replied. She just smiled and climbed into my truck and shut the door.

I was very confused now. Lilly Dawson was a fellow senior at my high school. She was also a very good friend of my sister and just happened to be one of the most beautiful girls in our class. The only times I had ever talked to her were in passing when she came over to see Kara. We had never had a real conversation. Yet here she was now, sitting in my truck and I was clueless as to why.

"You ready?" she asked. "Lets go!"

"Go where?" I asked, dumbfounded.

"Oh, you haven't told him yet?" Lilly asked my sister.

I looked over to Kara. She just smiled and pulled something from her purse. "You're giving Lilly a ride home," she said. Then I saw her pass what she pulled out of her purse to Lilly. It looked like the same big wad of folded bills that Rob had just given to her.

"Thanks, sweetie," Lilly said as she took the cash and put it into her purse.

I raised my eyebrow at my sister as if to ask "What the fuck?"

"I'll explain later," Kara said before I could ask any questions. "This is my treat, but lunch is about over so you can't do it here. That's why you're going to her house."

Suddenly, it clicked in my head. She had just paid for me to go with Lilly, I assumed to have sex.

My eyes widened and both girls laughed at my realization of the situation.

"Don't overthink it, Bri..." Kara smiled at me then walked off.

I smiled and shook my head then looked over to Lilly. She had a gorgeous but expectant smile on her face. It wasn't like I was going to turn down the opportunity so I started my truck and headed out of the parking lot. Lilly directed me where to go and fifteen minutes later we pulled into her driveway.

She lived in a big two-story house in a very nice neighborhood. The inside of the house looked as if it were professionally decorated but I didn't get to see much of it. Almost as soon as we entered the house Lilly grabbed me by the hand and guided me upstairs into her room.

"Hey, I really don..." I started to say after walking into her room but she walked up to me and stopped me mid-sentence.

"Shh. You can ask questions later. First, I want to have some fun!"

She smiled and walked up to me. She reached up and put her arms around my neck then stood on her toes to kiss me. Her lips pressed against mine and I instantly relaxed. My lips parted to allow her tongue to slip in and meet mine. I held her around her waist as we stood there and kissed for a while.

I was completely taken back by what was going on. Lilly was gorgeous and popular at our school. But what surprised me the most about this was that, unlike my sister, she wasn't known for being slutty at all. She was actually thought of as really sweet and kind of innocent. At least, that's the kind of reputation that she had. I don't think anyone would believe that she would do something like this.

Like I said, Lilly was one of the most beautiful girls in school. She was shorter than Kara by about three or four inches but often made up for that by wearing heels. She had long straight brown hair that was tied up in a cute but messy bun of some sort. She had big brown eyes accented by long lashes. She wore just a hint of makeup but not enough to hide the adorable freckles on her cheeks just below her eyes. Her lips were soft as they mashed against mine and I found myself starting to explore her body with my hands.

First I dipped one down her to ass. She had a perky bubble butt that was just made for squeezing. I slid my hands up her slim waist and ran my fingers lightly around the exposed skin of her midriff. She had the cutest belly button and a flat, smooth stomach. As she pressed her body against mine I could tell that she had chosen not to wear a bra underneath her thin spaghetti strap top and it made me wonder if she had any panties on under her tight jean shorts.

As we kissed she reached down and unbuttoned her shorts, pushing them down until they fell to the ground. She broke our kiss and grabbed my hand. As she pulled me over to the bed I could see her bare ass barely covered by a tiny thong. She backed me up to the bed and pushed me down into a seated position on the edge.

Sinking to her knees in front of me, her eyes never left mine. A sexy smile on her face the whole time. She fumbled with my belt for a moment before pulling it and my pants open. Then she dragged my pants down to my ankles and off completely. My rock-hard cock stood straight up in front of her, already teased from watching Kara earlier. A large drop of precum dripped down along the bottom of my shaft.

Lilly took it in her hand, smearing the precum around and started to stroke me.

"I've wanted to do this with you for so long!" she said, then dipped her head down and took the first two inches of my cock into her mouth.

"Ohhh..." I moaned. My cock finally getting the attention I had wanted since lunch. Although I much proffered this sort of attention to my own hand.

Lilly was slow and deliberate in her blowjob. Swirling her tongue around the tip of my cock while sucking on it, her hand slowly stroking the thick shaft and her fingers scraping against my balls. My cock wasn't enormous but it was definitely above average. I was proud to know that it was bigger than the guys I had seen Kara with.

Lilly removed it from her mouth and ran her tongue down the side and to my balls, licking one and then the other. She sucked one into her mouth gently, licking it in circles before releasing it and kissing her way back up the shaft.

"Emmm... it IS big," she said in between kisses. "Jennifer was right..." Then she took it back into her mouth, even deeper this time. Taking more than half of it in until it touched the entrance to her throat, then she started to bob her head up and down slowly.

'Jennifer?' I thought to myself. Jennifer was a girl I had dated earlier this year for a while. We had slept together but the relationship didn't last long. Apparently, girls talk.

After only a short time of receiving Lilly's amazing oral skills I could feel myself getting close. I ran my hand through her hair and held onto the bun lightly. My hips started to rock slightly but she had no intentions of getting me off yet.

"Nuh-uh, sweetie..." she smiled and gripped my cock tightly, holding it against her cheek. "Not yet! How about you come play with me for a bit?"

I grinned and nodded my head 'Yes'. I couldn't pass up an opportunity like that. Lilly stood up in front of me. She crossed her arms in front of herself and grabbed hold of her top, pulling it over her head to reveal her magnificent...

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