Babysitter Sister

Hi everybody! Thanks for giving this story a chance after that panfully cliche title! :P I'm not a very experienced writer, so hopefully this is readable (doubtful)! Please enjoy!

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Hi, my name's Josh. This is the 100% true story of what happened to me and my friend one night when we were just nine years old. All names have been changed to protect those involved.

The story begins earlier that day. Me and my best friend Mark were hanging out at our friend Kevin's house, with him and his brother, Craig. Craig was a few years older than all of us, but he didn't look down on us or anything like that. Me, Mark, and Kevin were talking about a sleepover at my house we had planned for that night, and what we should bring.

Eventually the topic shifted and Craig had told us a little about something called sex that he'd done with his girlfriend. He told us a little bit about it, but the three of us were still pretty blurry about most of it. Apparently girls had a hole instead of a dick, and guys put their penises in the hole to make babies. He made it sound really fun, even going so far as to say it was the best feeling in the world. We were very interested in what he was saying, but soon the topic shifted again to sports and video games, and sex was pushed out of our minds.

Mark came over to my house after school, and we called Kevin to ask where he was. He told us he wouldn't be able to make it, because he forgot about a movie he promised he'd go see with his dad. This left us feeling really disappointed, sleepovers were always most fun with three people. We were just re-evaluating our plans when my mom and dad informed us they were going out to eat and that my big sister would be babysitting us.

My sister's name was Ashley. She was an eighteen-year-old varsity cheerleader in high school, with shoulder-length blonde hair and long legs. She always had a lot of boyfriends and everyone thought she was really hot, though I was too young to really see girls that way. She was always mean to me and my friends, but she usually ignored us, which meant me and Mark could stay up as late as we wanted, and pretty much do whatever we wanted, so long as we stayed out of her way. Maybe this sleepover wouldn't be so bad after all.

My parents left the house at about 4:00, telling Ashley and us they'd be back by midnight. Once they left, Ashley explained that she had no intention of actually babysitting us, and that we were on her own while she hung out with her friends elsewhere.

"But what are we going to eat?" protested Mark.

"Like I know? Make some ramen or something." she said coldly.

"Mom and dad aren't going to pay you for doing nothing." I told her.

"Yeah? Mom and dad aren't going to find OUT." she said threateningly. "And if they do, well, next time I do cook for you, you'll be eating whatever it is through a feeding tube. Understand?"

"Okay, okay, I get the picture." I said quietly.

"Don't touch the thermostat while I'm gone, and don't stay up too late." she said, checking her watch. "I'm gonna take a shower before I head out. See ya later, kids."

"Yeah, whatever." I said. I hated when she called me a kid. She turned and entered the bathroom down the hall, and a few moments later we heard the water turn on.

"Your sister's mean." Mark noted.

"I agree." I said. "One of these days I'm gonna get her back."

"Uh huh." said Mark. It didn't sound like he believed it either. "So what should we do?"

"I dunno." I said. "There's not really anything to do at my house."

We brainstormed for a minute or so, with nothing coming to mind. Just when I was about to give up and suggest we play one of my video games that we've beaten a million times over, Mark got a huge grin on his face.

"Hey," he said, "We should have sex with Ashley."

I thought about it. I still wasn't completely sure what sex was, though I did know that the chances of Ashley doing anything with me and my friend aside from hitting us were about a million to one.

"I dunno, she's not going to go for that." I said honestly.

"Who cares?" asked Mark. "You just said you wanted to get back at her, so we'll just make her. It'll be funny."

I paused. "Mark, I don't know... I mean, I want to learn more about sex too, but what if she tells my parents?"

"Then you can tell them she was an awful babysitter." said Mark. "Josh, just don't worry about it. Craig said it was the best feeling in the world; even if you do get in trouble I'm sure it's worth getting grounded for a couple days."

Well, when he put it that way...

"Okay." I said. "So how are we going to do it?" We thought up a plan that sounded pretty good, then got ready.

........

We crept into the bathroom, quietly as we could. Ashley probably wouldn't have heard us anyway, because the cascading water was pretty loud, plus she was humming some new song. Her naked body was outlined behind the shower's fogged glass, showing off her big breasts, long legs, and tight, athletic body. Like I said before, at this point in my life I was still too young to really like girls, so none of these things especially turned me on. In retrospect, however, she was definitely a sight to behold.

I climbed up on the bathroom counter, and Mark crouched near the sink. We had our supplies in hand. All we had to do now was wait. It seemed to take forever.

As soon as she stepped out of the shower, I leapt. She let out a yelp of surprise as I tackled her to the floor. She landed hard, and was still stunned as I handcuffed her behind her back, and Mark bent her knees and duct taped them so they stayed that way.

This method of restraining her was over fairly quick, and by the time her senses returned she was unable to resist.

"What are you idiots doing? Get this stuff off me right now!" she ordered.

"Sorry, Ashley." I said, a little timidly. "We just want to do something. Don't tell mom."

"Don't tell mom what? What are you going to do?" she asked sternly. Her question was answered when Mark started poking and prodding a little slit on her crotch. Ashley moaned a little.

"Is this the vagina?" he asked. "I thought it was just a hole."

"Yeah, I think so." I said. "Is that it?"

"Hmmmm, nope." said Mark, continuing to probe it. "There's a little hole inside it."

"What are you doing?! Get away from me!" yelled Ashley. She looked worried but I ignored it.

"Let me feel." I said. This whole experience was as new to me as it was to Mark. Ashley was lying on her back, legs spread wide, shouting at us to stop what we were doing. We didn't. I got down on the bathroom floor between her legs and slid my fingers into the slit. It was warm and smooth, and sure enough, at one end there was a small hole. I slid the tip of my finger in as an experiment, and Ashley moaned again.

"I guess that's the right one." I said with a shrug. "It's really small though, will the penis seriously fit in there?"

"Only one way to find out." said Mark. He unzipped his pants and pulled both them and his tightie whities off. I followed suit.

"Whoa whoa whoa." said Ashley, realizing how far we intended to take this. "If you think I'm going to let you guys fuck me, you've got another thing coming."

Neither me or Mark knew what 'fuck' meant, but judging from how she used it, we had an idea. At the time, we had never heard of rape and didn't know that what we were doing was illegal. It was just a game to us, a childish prank to pay her back for being mean to us.

"Yeah? What are you going to do about it?" Mark asked her. He placed the tip of his dick on the slit. "Hey, my penis is really hard. Is that to make it easier to put in her hole?"

"Probably." I guessed. We'd definitely have to research this a little more when we were done. We both held our breath as Mark pushed the head of his dick into the slit, until it rested at her hole's entrance.

"One inch further and you can't imagine how much trouble you'll be in." Ashley said, gritting her teeth.

However, this statement only encouraged Mark, and he defiantly shoved forward. Both of us were surprised to see the entire length of his dick disappear into her. She and Mark both threw their heads back and moaned loudly.

"How does it feel?" I asked Mark.

"Really good." he gasped. "It's really warm and soft and damp and tight. It's squeezing my dick."

"That doesn't sound that great." I said skeptically.

"But it IS!" insisted Mark. "My dick feels all tingly, I can't even explain it!"

"You guys... are in such deep shit..." panted Ashley.

"How does it feel for you, sis?" I asked her.

"Awful." she said, her cheeks turning red. "As soon as I get out of this I'm going to kill you assholes." She didn't sound very convincing though, and I immediately suspected she liked it too.

For about a minute we just sat there, Ashley and Mark breathing heavily and me observing what went on. I noticed Ashley's nipples get hard and stick out more as Mark was inside her, as well as her slit parting a little to reveal what was inside. It was very pink in there, and now I could clearly see where Mark's penis had entered her.

"So now what?" he asked.

"I don't know." I replied. "You've done this before, right sis? What comes next?"

I was expecting one of her usual sarcastic replies, but was surprised when she said: "Pull out a little and then push back in again."

Mark slowly did this, and they both moaned.

"Oh man, that felt really good!" shouted Mark excitedly. "Even better than before!"

"Keep going in and out." she said. Mark pulled back a little again, then pushed in again, then repeated. Pretty soon he had a steady rhythm going, his nine-year-old dick pushing into her eighteen-year-old pussy at a steady rate. Both were groaning loudly.

"Does this mean you're cooperating?" I asked my sister.

"No." she panted, now clearly starting to enjoy it. "I just want to get this over with so I can beat both you guys to a pulp." Yeah right.

Watching the two of them have sex started making my dick hard, though I wasn't sure why. Being the odd man out didn't bother me though, I was perfectly satisfied just seeing this mysterious event unfold before my curious eyes.

Something that especially had caught my interest were my older sister's large, shapely boobs, which were bouncing around with Mark's thrusts. As though compelled by an unforeseen force, I knelt down next to her breasts and began to squeeze them experimentally. This elicited even louder moans.

"Hey, I think it feels good for her when you touch these." I told Mark, pressing and kneading the soft flesh. Mark said nothing, obviously very focused on his work as he continued to pump faster and faster.

After a few seconds of this, I thought I heard Ashley say 'lick them', but when I looked up for confirmation she was biting her lip, as though she'd said something she didn't mean to. I figured I might as well give it a try, and lowered my head to lick her right nipple. She let out a cry that almost made me jump back in surprise, but I kept going, licking every inch of her tits and trying not to leave a single bit dry.

Eventually Mark spoke up again, his thrusts reaching a fever pitch. "Oh man, I feel really weird now! I think something's going to happe- AAAAAAHHH!" He screamed and plunged his dick into Ashley as far as it would go, trembling and shaking. After a few moments he stopped and pulled his penis out of her. He collapsed in exhaustion.

"Are you okay?!" I asked worriedly, kneeling over him.

"Yeah, I'm fine." he said, sitting up. "Something came out of me. Out of my penis."

"Like pee?" I asked. I looked at him reproachfully. "Did you pee in my sister?"

"No." he said. "It felt really good, like the best feeling in the whole world. It wasn't the same."

This confused me. What had happened. I turned back to look at the hole he'd just exited. My sister's slit was wide open now, and I could see all of the pinkness inside, including the tiny hole my friend had just exited. I saw something else too, though. Some weird white stuff was dripping out of the hole. I wiped some of it off with my finger and sniffed it.

"Is this what came out?" I asked.

"I guess so." said Mark. "Wow, it looks weird."

"That's called cum." said Ashley. "Guys shoot it out of their dicks to get girls pregnant." She was definitely being more cooperative now. She told us what it was and we didn't even ask.

"Oh." I said. "So are you going to get pregnant now?"

"No, probably not." said Ashley. "You guys are too young to be making cum that works."

"I see." said Mark. "And what was that thing I felt?"

"That was an orgasm. They're the best thing about sex." said Ashley. "Girls get them too."

"Oh! So you got one? Did it feel the same?" asked Mark.

"Not yet." said Ashley. "You didn't fuck me long enough. I was close to having one though."

I was still a little confused about the whole thing, but my hard penis knew what it wanted. "I'll give you an orgasm!" I volunteered.

She just laughed. "I'm sure you will. But get this stuff off me first so we can do it in my room."

I moved immediately to free her, but Mark stopped me.

"How do we know she won't beat us up as soon as we let her go?" he asked.

"I know Ashley." I insisted. "She's telling the truth."

It took a little convincing but Mark finally conceded. We took off the handcuffs and tape, and though we still partially expected a beating, she simply headed for the door.

"Follow me." she said in an enticing voice.

We did so, following her out the bathroom door and upstairs, where her bedroom was located. After entering, she closed the door and locked it.

"I'm only doing this because I want my orgasm." she assured us, then got on her hands and knees on the rug.

"What are you doing?" asked Mark, confused. "Get on your back."

Ashley smiled. "That isn't the only way to have sex. Josh, get behind me and do exactly what you saw Mark do before."

I got behind her and put my rock hard dick against her slit, searching for the hole. Her vagina was much hotter now than when I first touched it, plus it was stickier and more moist. It definitely felt inviting. Finding my target, I plunged my erection into her.

Wow, did it feel good. Even now I have difficulty describing the wonderful sensation. It was a sort of soft, snug warmth that made me cry out with surprise and pleasure. Ashley moaned as I pushed my dick into her. Her pleasure was obvious now, and began rocking her hips back and forth.

"She wants you to start going in and out." said Mark, stating the obvious. I granted her wish, and began easing my penis in and out of my older sister's pussy. The sensation was incredible, and as I gained speed it got even better.

Mark watched us fuck for a while before saying: "So what am I supposed to do?"

Between moans and gasps Ashley replied: "Get in front of me." Mark did this, leaving his hard dick at about eye level for Ashley. She grabbed it with one hand and began stroking it, eliciting a moan From Mark. Then she did something neither of us expected, she began to lick it.

"Ohhhh, that feels so good..." moaned Mark. I slowed my thrusts a little, watching in fascination as she licked all over his tool before finally putting the whole thing in her mouth. She began slowly pumping in and out. It surely felt pretty good for Mark, but I couldn't imagine anything feeling as good as fucking my older sister's pussy.

Eventually I felt a great pleasure building up, and I sped up my thrusts to as fast as I could go. This must have been what Mark felt right before his turn was over.

"Ashley! Ashley! It's happening!" I moaned.

"Do it, Josh! Keep going!" she yelled, taking her mouth off Mark's penis for a second. "I'm almost there!"

"I'm going to shoot my cum into your pussy, sis! I can feel it!" I cried.

"Fuck yes, do it! Fill me up with your cum, little bro!" she savagely groaned.

That was all I needed. I buried my cock in her as far as it would go, firing shots of my 9-year-old seed into her 18-year-old womb. Ashley let out a scream of pleasure, her pussy tightening and spasming around my penis in what must have been her orgasm. Waves of pleasure washed over me, and it seemed as though I was taken to another world. At the same time, Mark cried out as well, shooting a couple loads of his sticky white seed into her mouth before slipping out and shooting a few more on her face.

As our orgasms subsided, we collapsed to the floor of my sister's room, spent and exhausted. Eventually she got up and cleaned herself up, then got dressed. We did the same. Before leaving to hang out with her friends, Ashley assured us that this encounter was a one-time thing, and that it definitely wouldn't happen again.

Me and Mark weren't so sure.

TO BE CONTINUED

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That wasn't too painful, right? I have a couple more chapters of this written... if anybody's interested I'll post 'em. Please review.. and thanks!