Babysitter Sister

Here's chapter 3... Hope you enjoy it! :)

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"OH!" moaned Ashley, bouncing up and down on my friend's shaft. "Oh, Mark! Fuck me harder! HARDER!" My eighteen year old sister was straddling my friend Mark's hard young prick, while Kevin penetrated her ass doggy-style.

"Mmmm... Ashley, this feels so good!" exclaimed Mark, thrusting up into her ever faster, his hard cock reaming her pink hole.

"OH MY GOD! OH, YES!" she cried. "And Kevin, don't stop!"

"Right!" he said, continuing to pound her ass.

She moaned in pleasure. I unzipped my pants and allowed my erection to pop out in front of her face. She passionately accepted it, taking it into her mouth and sucking it like a popsicle.

It had been a couple weeks since our last experience, so it didn't take any of us long to cum. I blasted a huge load into her mouth, Mark groaned and fired his into her womb, and Kevin left his in her ass. After that we switched, and switched again, so when we were all done Ashley had some cum from each of us in every orifice.

This was how we usually did it. It had been about a month since Ashley had talked to me in my bedroom, and once I relayed her message to Mark and Kevin, they came over every time she babysat. And since my parents seemed to be spending more and more time out of the house during evenings, this meant plenty of sex for all three of us. Correction, all four of us.

Yes, Ashley seemed to have more fun doing it than any of us. In retrospect she had a greater understanding of what we were doing than any of us, its importance and ramifications. After all, we still saw it as just a game, something fun to do. Like PlayStation or baseball.

Mark and Kevin, completely spent, were getting dressed, while I was going for a second round in Ashley's pussy, which had become my favorite hole. I didn't know what it was, but something about fucking my sister and filling her with my cum, even though I knew I couldn't get her pregnant, aroused me greatly.

I moaned and came for the fourth time that day, filling her with another boiling hot load.

"Mmmmm..." said Ashley. "That feels good."

"I'll say it does." I said, sighing happily, withdrawing my softening rod from her older twat. In my absence, a small amount of cum oozed from her orifice. I distinctly remember being turned on at the sight, not from seeing the cum ooze out, but from considering how much had to still be packed in her. "Thanks for letting us do this, Ashley."

"Yeah, thanks a lot!" Mark and Kevin chimed in.

"My pleasure." said Ashley sexily, standing up. Some of our white seed dribbled down her leg, and she wiped it off and brought her hand to her mouth. She licked her lips at the taste and began to dress herself. While me, Mark and Kevin had already switched to discussing the latest Tony Hawk, we were all surprised to see her putting on her cheerleading uniform.

"You have practice?" I asked.

"No, not practice." she said, checking her hair in her bedroom mirror. "Don't you listen to anything? I told you there'd be a game tonight."

"Oh, wow." I said. "Well, good luck."

She turned and smiled at me. "Thanks." Now, as I said before, I wasn't completely at the stage where I was interested in girls romantically, but looking back on it she must have looked incredibly hot. Wearing that yellow and blue cheerleader outfit with the short skirt that showed off her long, beautiful legs, plus the tight top that accentuated her sizeable tits while baring her fit, tight midriff for all to see. Too bad I wasn't a little older, so I could more fully appreciate the devastating beauty of the girl I fucked so frequently.

"So in other words, you're leaving us unsupervised?!" asked Mark excitedly.

"Sure." shrugged Ashley, now putting on a little makeup. "Order a pizza. Throw a party. I don't care."

"You're the best sister ever!" I said happily, giving her a hug.

"Cute." she said sarcastically, though she returned the hug anyway. She put her shoes on. "Anyways, I'm off. I should be back before mom and dad get home, but keep an ear out for the driveway anyway. If she catches you guys going crazy and I take the blame for not watching you, you'll never have sex with me again. Understand?"

The three of us nodded. She didn't really need to threaten us, we kind of knew we owed it to her, not to cause too much trouble while she was out. She was doing us big favors every time she babysat, the least we could do is return them.

................

Later that night, after we ordered a pizza and watched a couple TV channels our parents wouldn't have normally let us watch, Kevin and Mark went home. I played video games for a little while, but was interrupted by the sound of my parents car in the driveway.

"We're ho-ome!" came the sound of my mom's voice. I paused my game and went downstairs to say hello.

"Hey kiddo. Where's Ashley?" asked my dad.

"She had a game tonight." I said casually.

"Oh! Harold, that's right! The game! I knew we were forgetting something!" said my mom. "We should have hired someone."

"Nah, it's fine." said my dad. "Josh's getting old enough to take care of himself! Aren't you son?" I laughed and nodded. It looked like both me and Ashley were getting off the hook tonight.

"Well, it doesn't look like he got into any trouble..." said my mom, looking around at our meticulously cleaned house. She spied the pizza box through an open door, in the kitchen garbage. "Pizza? Honestly, I hope your sister's feeding you."

"She heated up some leftovers too." I lied. "It was pretty good."

"Well that's good." said my dad. He glanced at his watch. "That game should be over by now though. Wonder what's keeping her?"

I was surprised. I hadn't noticed how late it was. Come to think of it, she did say she'd be home before mom and dad got home...

She didn't end up coming home until about 2 AM. Mom and dad were furious. They woke me up from yelling at her. I couldn't hear much of what they were saying from up in my room, but it sounded like they thought she was out having sex with some guy. She didn't deny it and that only made them madder.

How could they be mad at her for something like that? No doubt she made that guy really happy. I know it made me happy when she did it to me. These were the last things I thought about before I closed my eyes again...

...........

"Dang, another F." complained Mark, holding his test paper as though it were contaminated with a deadly plague. "I'm gonna be so grounded."

"We're all gonna be grounded." I said bitterly, as me and Kevin were holding papers that we're a whole lot better. Fifth grade just never gave us break.

"Not to mention completely doomed on this report that's coming up." said Kevin. "We might as well just give up now."

"What report?" asked Mark.

"The one on World War 2." I told him. "For Mr. Hampton."

"Oh yeah." said Mark. There was a short silence. "I don't know anything about World War II."

"Neither do we." said Kevin. "We we were hoping maybe you paid attention in class, even a little. It would definitely be much more than we did."

"Are you kidding me? It's impossible to pay attention in Hampton's class." said Mark. "The only kid who isn't failing in there is Phil."

We could believe it. Phil was the smartest kid in our class. His eyes were always glued to the teacher, taking notes, and on his exams he always got 100s. Unfortunately his brightness came at a cost, and he was pretty much a social outcast right from the moment he transferred to our school a few months back.

"I got an idea." said Mark. Uh oh. Another one of Mark's schemes. "Let's ask Phil to help us."

"Why would he do that?" I asked skeptically.

"Because he wants to be popular." said Mark. "He helps us out, he figures he can get on our good side. Wouldn't you be more inclined to hang out with a kid if he saved you from going to military school? I know I would."

Me and Kevin thought about it. Mark got bad grades but he was still a pretty knowledgeable kid, for his age. If he actually applied himself instead of playing video games all day long, maybe he'd have a chance of passing History without Phil's help. But it was pretty much a given that that would never happen.

We agreed to talk to Phil, and at lunchtime we went off to talk to the kid. He was at his usual place on the stairs, eating a sandwich from his brown-bagged lunch.

He looked up at us through his thick glasses. "What do you guys want?"

We weren't surprised he was apprehensive towards us. Ever since he'd come to our school he'd been bullied a lot. We never did any of the bullying, we figured it wasn't right (though of course we never stopped any of it from happening, which is really just as bad). He probably figured we were just like all the rest.

"Nothing." said Kevin. "What's going on?"

"I don't have any money." said Phil guardedly.

"Man, we're not here to pick on you." said Mark. "We were just wondering if you could help us with Hampton's report."

Phil thought about it. "No."

"Why not?" asked Mark.

"I'm working hard enough on mine." said Phil. "Besides, why should I do your work for you? You'll never learn that way."

Mark sighed. "What if we give you something?"

Phil looked at him. "Like what?"

"I dunno." shrugged Mark. "Money? You want some games or something?"

Phil shook his head and blushed. "No... Actually... There's something else I want."

"Well, what is it?" I asked him impatiently.

"I want..." he swallowed and his voice got low. "...to get laid."

A short silence.

"Laid? What does that mean?" I asked. I looked at Mark and Kevin and they seemed just as confused.

"Sex. I want to have sex." explained Phil. "You guys are pretty popular, right? Surely there's a girl you can hook me up with..."

I almost laughed. Us, popular? We were gamers. We didn't exactly get beaten up every day, but the truth was we were barely above Phil on the totem pole.

"You're mistaken." I said. "We don't know anyone. We do have some pretty great games though-"

Mark put his hand on my arm. I looked over at him and saw that familiar look of inspiration in his eyes. "Actually, we do know someone. An older girl."

I almost asked him, 'who?', but even I wasn't that stupid. I knew perfectly well who he was referring to.

"Really?!" asked Phil excitedly. "You know someone?!"

"We MIGHT know someone." I said quickly. "We'll let you know if we can work something out." I hurriedly shuffled Mark and Kevin away.

"Huh? Why did you say 'might'?" asked Mark, looking mad. "This is a great idea!"

"We have to see what Ashley says first." I told him. "I just don't want to make any promises we can't keep."

"Why wouldn't she want to have sex with him?" asked Kevin. "She has sex with us, what's the difference?"

"Who knows? All I'm saying is we should make sure." I said. "I'll ask her tonight."

"I sure hope she says yes." said Kevin nervously.

"Me too." agreed Mark.

......

"No way." said Ashley. "Absolutely not."

"Why not?" I demanded. After proposing the idea of Phil to her, she initially seemed interested, but after showing her a picture of him in my yearbook her mind changed completely.

"Just look at him." she said, stifling a laugh. "There's no way."

"Please?! My grades are riding on this!" I begged. "All of ours are!"

"Too bad." she said. "Study more. I don't know. But there's no way you're going to get me to screw this nerd."

I was completely crestfallen. Now what? I gave Mark a call and broke the news. We brainstormed other ideas for getting this project done, but nothing seemed possible. It looked like we were doomed to fail Hampton's class.

Just when I was about to give up and say goodbye, Mark put forth a crazy idea. It was so ridiculous I immediately vetoed it. But as he explained it to me, I realized in my desperation that it was the only way. We said are goodbyes and then I called up Kevin to tell him what me and Mark had just discussed. He seemed just as concerned as me. Even as I hung up the phone and got ready for bed, I wasn't convinced at all that it would work. All we could do was wait and hope.

............

The next time Ashley babysat was about a week later. She seemed eager to start fucking. As soon as we got up to her room she started undressing, and we made an unusual proposition.

"Cuffs?" she asked with a grin as she took off her tight jeans.

"We saw it in one of Kevin's brother's magazines." I explained.

"Pleeease?" asked Mark. "We just want to see what it's like."

"Hmmm..." Ashley seemed to think about it, but when I saw her panties getting wet, I knew she'd already decided. She slid them off, unaware that I'd been staring. "Alright, but just for a little while."

"Nice!" we said.

"So how do you want to do it?" asked Ashley, unfastening her bra and dropping it to the floor, revealing her large, round, perfect tits to the room. She was totally naked now. I felt my cock stiffen in my pants, though it wasn't because of her beauty, which was wasted on me. It was simply from the anticipation of having sex.

"In the magazine the girl was on the bed, and she had one limb cuffed to each of the bedposts." I explained. "Would that be alright?"

Ashley smiled. "Yeah, that sounds fun. You're gonna need 4 pairs of handcuffs, though."

"Got 'em." said Kevin, taking off his backpack and pulling them out.

"Hah, pretty sure I'd say yes, eh?" asked Ashley, lying down on her back on the bed. "You know me too well."

We got to work fastening the handcuffs. I worked on her hands while Mark and Kevin each took a foot. She moaned at the click of the cuffs closing.

"Mmmm... I've never done anything this kinky." she said erotically. A puddle of her juices had already formed on the sheets under her cunt. She seemed to be sweating with anticipation, her well-exercised body shiny with arousal.

Looking back on it, I don't know if I've ever seen her so incredible, and she's a very hot girl. My cock was straining against my pants now. I could see every inch of her pink pussy, open between her spread legs, seeming to call out to me. I wanted desperately to skip the plan and just nail her right there, but I managed to resist.

"What are you guys waiting for?" she asked lustfully. "Get your clothes off and come fuck me!"

"Okay Phil, come on out." said Mark.

The door to Ashley's closet opened, and Phil walked out, looking nervous.

She saw him and her jaw dropped. He saw her and his jaw dropped.

"What... the fuck..." said Ashley, her expression becoming angry, "...is going on here."

"What do you think, Phil? Is she hot enough?" asked Mark desperately.

Phil stared at him like he was insane. "Are you serious?! Just look at her!"

Mark looked at her. "So you'll do this report for us, right?"

"You gotta be kidding me! I'll do all your reports for the rest of the year if you let me have sex with that!!" Phil exclaimed. He looked at me. "And she's your sister?!"

"Uh, yeah." I said.

By now Ashley had obviously figured out what was going on. "You fuckheads are so dead if you let that kid do me!" she shouted, gritting her teeth and straining against her bonds. "You'll never have sex with me again, I promise you that!"

At this I hesitated. Was it really worth it. I turned to my friend. "Mark, should we call it off-"

"No." said Mark. "Just trust me on this, man."

Phil looked at us, waiting for our approval.

"Go ahead." I told him. "Take your time."

Phil started stripping off his clothes before I could finish the sentence, never taking his eyes off our offering. Ashley swore at us.

"Sorry Ashley." I told her. "We can't fail any more stuff or we'll be held back."

"Like that's my problem!" she yelled, as Phil climbed on top of her sculpted body. His cock looked stiff as a rock, and he was breathing hard. He laid on top of the taller girl, his dick level with her pussy and his head level with her big tits. He began roughly fondling a tit with each hand, while licking the nipple of the left one.

"You guys are... ngghhh... gonna regret this forever..." grunted Ashley, trying not to show any signs of pleasure as he forcefully handled her. However her pussy betrayed her, and the puddle beneath it only grew larger as Phil's stiff young prick nudged and rubbed up against her opening.

Phil finally seemed to notice where his dick was, and stopped his treatment of her breasts. They were pink from the kneading, and there was a red bite mark on the left one.

"Th-that hurt..." gasped Ashley, though her face was flushed with arousal.

"I'm gonna do it, guys." trembled Phil, gripping his cock and holding at the entrance to my sister's love tunnel.

"So do it already." said Mark impatiently. I could tell he was as eager for his turn as I was.

We watched closely as Phil's cock disappeared into my sister's hot, sticky twat. They both moaned in unison.

"Oh... oh my gosh..." moaned Phil.

"How is it?" asked Kevin, sounding bored.

"It's... it's squeezing my dick really hard! Oh man! OH! But it's so soft!" he babbled. "Not like my hand at all!"

I looked at Mark. "His hand? What's he talking about?" But Mark was just as perplexed as I was.

"You guys will never fuck me again, it's over." panted Ashley. "I'm telling mom, too, Josh." That last sentence should have struck fear into my heart, but I could tell she didn't mean it.

Phil started slowly moving in and out, as Ashley continued to say empty threats between passionate moans. "You guys... this is the best feeling ever... How long have... OH! OH!?" He was beyond the point of coherent speech.

He gradually picked up the pace, and before long his nine-year-old prick was slamming her eighteen-year-old pussy like a jackhammer, her abused D-cups bouncing with each thrust. Their moans became so loud they seemed to join into a single animalistic call of desire.

"I'm really close!" yelled Phil, not slowing his pounding a bit. "Can I do it inside?!"

He expected me to answer, and I almost did, but Ashley spoke up instead. "YES! Oh god, flood my gash with your hot young seed!"

Phil didn't need to be told twice. He dove his cock into her tight chute as far as it would go, moaning as he emptied his load into her.

"AHHH! It's so hot!" moaned my sister. "I can feel it filling me up!"

When Phil was finally done, he withdrew his cock from her, exhaling a sigh of bliss. A small bit of Phil's cream spilled out of her and onto her light blue bedsheets.

"I can keep going, right?" he asked us.

"Sure." I said. "She's all yours."

"Great." he said. "I wanna see what her mouth is like."

"What do you say, Ashley? Can you give him a blowjob?" I asked my sister.

"Okay, but one of you guys had better give my pussy some attention!" she demanded. "I'm so close!"

"You got it." grinned Mark, starting to strip down.

"Hey, but I want to-" I started.

"You'll get your chance, man." said Mark. "I'm dying here!"

"She's my sister." I pointed out.

"Yeah." said Mark. "And this was my idea. C'mon man, you know I never last that long."

I sighed and nodded. "Just hurry."

This request was probably unnecessary, as Mark jumped up on top of her immediately and rammed his cock deep inside her tight, oozing cunt. Ashley jerked involuntarily at the sudden penetration, and moaned through a mouthful of Phil's dick.

"Ohhhh... I'm never gonna get tired of this!" said Mark, starting to ram his cock in and out of her, faster and faster. Ashley was completely into it now, bucking her hips upwards to meet Mark's thrusts, as well as passionately sucking and tonguing Phil's hard-on.

I couldn't resist any longer. I straddled her chest and wedged my cock between her big, natural tits. Even with the bite mark, which still shone around her nipple, they looked beautiful. I mashed them unceremoniously against my young prick and began to thrust, marveling at the feel of their delicate softness against my shaft. I crushed and kneaded them violently as I assaulted her valley. She nearly reprimanded me for my rough approach, but failed to finish the sentence due to her pleasured moaning.

"I'm really close again..." moaned Phil, fucking my sister's mouth hard and fast.

"M-me too!" cried Mark from behind me. I couldn't respond, my pleasure was so great, but I could feel my orgasm approaching as well.

The three of us came at once. I heard Mark groan in orgasm from behind me at the same time I fired five thick ropes of cum between Ashley's boobs. I was afraid that my handling of them was so rough that when I released them they'd be warped or malformed, but they eagerly retained their perfect, spherical shape. They were, however, very red.

I looked up to see Phil withdraw his deflating prick from Ashley's mouth. I caught a quick glimpse of at least 1/4 cup of cum inside her mouth, before she closed it and swallowed the whole thing in one gulp.

I climbed off her and the bed, and watched Mark extract his cock with a sigh. We examined the sight of my violated older sister, cheerleader, sweating and breathing hard. The cuffs still decorated her wrists and ankles, though we knew at this point they weren't necessary.

"I'm spent." said Phil, exhausted.

"I think I could go again." said Mark. "And Kevin hasn't gone at all yet."

"What about you, sis? Have you cum yet?" I asked her.

"No!" she said, sounding frustrated. "You guys suck! Uncuff me so we can do this RIGHT!"

We did so. She sat up and rubbed her wrists, the huge load of my jizz between her tits running down her stomach to her pussy.

"It's still warm." she said seductively, putting a glob of it into her mouth. "Now get over here and get me off, I'm seriously burning up."

I laid down on my back on her bed and watched her climb on top of me. Her pussy was in full bloom, very red, glistening with moisture. Even though I knew it had been fucked twice so far that evening, and many, many times before that, it still looked completely pure and innocent. I positioned my hard tool at it's entrance, and my sister slowly lowered herself down onto me. We moaned as I completely entered her astonishing love canal, feeling it stretch to accommodate my small cock. The pleasure was so great I'm sure that had I not already I cum, I would have spent my load right then and there. I immediately began thrusting upwards. My older sister's pussy was very soft, yet so tight and firm, on my young prick.

"Mmmm, that's good." said Ashley. "Somebody fuck my ass, now."

Kevin was that somebody. He eagerly got behind her and shoved his rock hard, waiting dick into her hole. She moaned and started jerking Mark off, who was standing in front of her.

"You quitting already?" she asked Phil, who was getting dressed, looking exhausted. "It's just starting to get interesting." Indeed it was, as I began thrusting up into her pussy, and Kevin began slamming her hard.

Phil watched us for a second and decided that maybe he did have a little more in him after all. He walked over and unzipped his fly. Ashley fished his erect prick from his jeans and began stroking both him and Mark, sucking both of them in alternation.

After I shot a huge load in my sister's tight, pulsing quim and Kevin deposited his first that night in her ass, and Mark and Phil came in her mouth and on her face/tits, we continued to rotate positions. Each of us came a total of 5 times in that memorable night.

Then, seemingly as quickly as it began, it was over. Ashley had cum splattered all over her sculpted, athletic body, as well as oozing from every orifice. Phil went home satisfied and promised to do our homework for us for the rest of the year. Me and Mark and Kevin all said our goodbyes to each other and they headed out. It was just me and a very worn-out looking Ashley.

"That was pretty fun." she said, lying on the floor of her room in a daze.

"Yeah." I replied.

We spent a moment sitting in silence before I got up to play video games, and Ashley got up to take a shower before mom and dad got home.

"Hey Josh." she said, as I was walking out the door.

I looked back at my big sister, cum dripping off and out of that perfect body anyone would kill to have. "What is it, Ash?"

She smiled. "Anytime you guys want to have friends over is fine with me."

I wasn't sure what to say so I just said thanks and returned to my room. Was this adventure in sex only just beginning?

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Well, that's it! Thanks again for all the hits and the feedback. :D There's 4 chapters of this in all, so stay tuned, it's almost over. Hope you liked it!