Babysitter Sister

Thanks for the reviews, everybody! Glad it isn't quite as bad as I thought. Here's chapter 2 :)

--------------------

Kevin was already pretty mad about missing our sleepover, but the next day when we told him what we did he went absolutely crazy. He couldn't believe he missed the chance to have sex, for a movie he said wasn't even that good.

"Yeah man, it sucks that you missed it." said Mark. "Craig wasn't lying, it really was the best feeling in the world."

"I can't believe you guys have had sex already and I haven't!" he said, frustrated. "Is your sister going to babysit again soon?"

I laughed. "Maybe... But I don't think we should do it again."

Mark looked shocked. "Why not?!"

"Ashley let us get away with it once, but if we made her have sex with us twice she'd pulverize us every day until the end of time." I said. "Plus we had the element of surprise yesterday. She'll be on guard next time."

Mark opened his mouth to argue, but then closed it. He knew I was right. She might have been a girl, but she was twice our size (and age), plus in great physical shape due to her cheerleading. It was pure luck that we even got away with it once, element of surprise or not.

"Dang." said Kevin. "I guess I'll just have to have sex with somebody else then. I can't let you guys beat me!"

We both laughed. Kevin was very competitive.

"So what should we do?" asked Mark.

"I dunno, you wanna go see a movie?" I asked. "The new James Bond movie's playing now."

Everyone agreed that this sounded pretty fun (more fun than sitting around thinking of something to do, at least), and we headed to the movie theater.

The movie was mostly pretty boring, just the usual spies, explosions, and car chases. There was one scene that seemed to catch Mark's interest, when a Russian spy put Bond to sleep with a chloroform-soaked rag. He smiled with a look of realization, and I wondered what he was thinking about.

My question was answered pretty quickly, when the credits rolled and we exited the theater.

"Hey, does that really work?" asked Mark.

"Does what work?" I asked him.

"That chloroform stuff. Will it put people to sleep?" he asked.

"Probably." I said with a shrug. "Why?"

"Because." said Mark with a smile. "That's how we're going to have sex with Ashley again."

..........

The guy at the drugstore gave us some weird looks, but he sold us a bottle of chloroform anyway. Mark and Kevin were totally sold on this idea, but I still wasn't sure.

"So we'll keep it at Kevin's house until the next time your sister babysits." said Mark. "Sound good?"

"I guess." I said.

"What do you mean, you guess?" asked Mark. "We're doing this, right?"

"I don't know." I said. "I mean, how would we ever get close enough to her to use it? You have to put it right over the person's face and keep it there. She'd beat us to a pulp before it could take effect."

Mark thought about it. "Well..."

"Plus, it might have kept Bond out long enough to take him back to bad guys' base in the movie, but does it really work that well in real life? How do we know she won't wake up before we're done?"

"Look." said Kevin. "She's YOUR sister. If you don't want to do this, then we won't do it."

"Yeah." agreed Mark. "It's your call."

I shook my head. "It's not that I don't want to, it's just-"

"...But until we DO use it, it stays at Kevin's house." said Mark. "His parents never search his room, and if we get caught with this stuff our parents might give us more than just weird looks."

"Let's go stash this and head to the arcade!" suggested Kevin. From then on the conversation switched to who could school who in Street Fighter.

Well, it was up to me then. I was pretty sure I didn't want to go through with it, but on the other hand... Oh well, my parents didn't go out often, so at least I'd have some time to think about it.

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

And I did have time. Two weeks, to be exact. The only problem was, it was the day of my parent's date, 15 minutes before they were leaving, and I still hadn't contacted Mark and Kevin or made a decision.

Mom and dad were in Ashley's room, going over the emergency phone numbers for her. She wasn't paying attention, though. She was researching online for apartments and stuff in Los Angeles, where she was moving after she graduated in a couple months. One thing was for sure, if we were going to have sex with her again, we didn't have long to do it.

Still divided, I figured the only way to decide was with a coin toss. I pulled a quarter out of my pocket and flicked it up into the air, then caught it and slapped it on the back of my hand. I was about to call it, but had a better idea. I ran up to my sister's room.

"Call it, Ashley." I told her.

"What?" she asked, trying to ward off my parents and surf the net at the same time.

"I flipped a coin." I said. "Call it."

"Heads." she said irritably. "Beat it, douche."

I left her room, wondering what a douche was, and revealed the coin to myself.

It was heads.

Pretty good choice, sis. I picked up the phone and made the preparations.

...........

"So you brought it?" asked Mark excitedly.

"Yup, it's in here." said Kevin, holding up his backpack.

"Awesome! I can't wait!" exclaimed Mark.

"Shhh!" I said harshly. Ashley didn't know Mark and Kevin were here, and in fact she'd specifically told me I wasn't allowed to have any friends over. This would definitely have to be a stealth mission.

"Sorry." whispered Mark.

Ashley was upstairs in her room, surfing the net. Her computer was positioned against the far wall, so her back would be facing the door. All we'd have to do was tiptoe inside, put the rag over her mouth, and hope.

We grabbed a rag from the laundry room and put some of the stuff on it. We weren't sure how much we needed, so we added plenty.

"I hope this works." said Mark.

"Me too." I agreed. Kevin didn't say anything, he looked nervous and lost and thought.

We snuck up to her room. It was open a crack. Inside, we could hear Ashley typing away on her keyboard.

"You guys stay here." I whispered as quietly as I could. They just nodded in response. One of us could get caught less easily than three of us.

I eased the door the rest of the way open. It went noiselessly, as our dad always kept the house in meticulous repair.

I tiptoed towards Ashley as quietly as I could, the chloroform-stained rag cold in my hands. She continued to type as though nothing out of the ordinary was happening, not seeming to notice me at all. I crept closer and closer, until I was standing right behind her. She had no idea I was there, completely absorbed in what she was doing. I gulped. It was now or never.

Quickly and unceremoniously, I clapped the rag over my older sister's mouth. I saw her eyes widen with shock, but only a second after the cloth touched her lips, they fluttered shut. She slumped to the side and fell out of her chair, hitting the floor hard. I was afraid thus would wake her up, but it didn't. Ashley simply lay on the floor, breathing deeply and peacefully, as though she'd been sleeping there for hours.

Mark and Kevin eased the door open cautiously.

"Did it work?" asked Mark.

"Yeah." I said, unable to believe it. "Come on in."

They did, approaching my sleeping sister very carefully. We took off her pajamas, with some difficulty moving her around, leaving her totally naked.

"So now what?" asked Mark.

"We'll let Kevin go first." I said. "He's been waiting for this."

"Darn right I have." said Kevin, taking off his pants and boxers. His penis was already hard.

"Do you know what to do?" Mark asked him.

"Yeah." said Kevin. "I looked at some of Craig's magazines."

"Then go ahead." I said. "We can wait."

So Kevin got down on his knees between Ashley's long legs, and pressed his dick against her slit. Spreading her pussy lips with his penis' head, he slowly slid his length into her canal, moaning as he went.

"Ohhhh..." he gasped. "It feels really good..."

"Yup." I said.

"Is it wet at all?" asked Mark. "Last time it was."

"It's starting to be." replied Kevin, starting to thrust his young dick in and out of my sleeping sister's 18-year-old snatch. "But wow, it feels so good! This is the best day of my life!"

I knew what he meant. That's how I had felt too, the first time I did it. Needless to say, I was looking forward to my turn once Kevin was finished.

To keep myself occupied, I started playing with Ashley's boobs. They were big and firm, yet also soft and pliant. My dick got hard at the contact, which gave me an idea. I took off my clothes and wedged my hard penis in between her big tits. Squeezing them together to make the orifice as tight as possible, I began thrusting in and out.

"Whoa." said Mark. "I would have never thought of that. How does it feel?"

"So... good..." I gasped. Her soft tit flesh gave my young penis immense pleasure. I squeezed and kneaded them fiercely as I fucked, blown away by the sensation on both my shaft and my palms. Her sleeping form, totally unaware of our practices, rocked back and forth as Kevin and I violated her.

Mark was getting frustrated. He didn't like being left out. He tried putting his erection in her mouth, but with her unconscious and unable to pleasure him with her tongue it wasn't fun for him at all.

"Hurry up, guys." he finally said impatiently.

"Ohh... I feel weird..." moaned Kevin, pumping faster and faster. "I think something's happening..."

"Keep going." said Mark. "You're just about to come."

I was almost there myself. I moaned and dug my cock as deep into her soft valley as I could, shooting four big loads inside. At the same time I heard Kevin shout behind me, and I knew he was filling my sister's adult womb with his seed.

I climbed off my sister and looked down at her tits. I'd turned them slightly red with my brutal squashing and squeezing, and there was a large puddle of cum in between them. Kevin slid out of her pussy, and a bit of cum dribbled out of her hole as he left.

"So what did you think?" I asked him.

"It was amazing." he gasped, still out of breath and swirling with sensation. "Josh, that was the most fun I've ever had in my life."

I nodded. "Well Mark, it's your turn, I guess." I looked around. He wasn't there.

"I think he went to the bathroom or something." said Kevin. "I wasn't really paying attention."

"Me either." I said. Who WOULD pay attention to something like that when they were having sex? "Should we wait for him?"

"We can't wait." said Kevin. "We don't know how long your sister's going to be out for. Just take his turn."

"He won't like that..." I said doubtfully.

"Who cares?" asked Kevin. "It's his fault, what kind of idiot would just leave?"

"Yeah, you're right." I agreed. The plan was that all three of us would have sex with her, then we'd clean her up and put her clothes back on her and hope she never knew. We couldn't waste a second just waiting around. Sorry, Mark.

My dick was still hard so it wasn't even a second before I had the head of my cock pressing against my sister's entrance. I closed my eyes and eased my length into her tight cunt. God, it felt good. Her pussy was scalding hot with arousal, a damp, velvety pocket which tenderly gripped my member. I slowly started moving in and out, then picked up speed. The feeling was incredible. I'd never get tired of this, ever.

I thought Kevin would fuck her tits like I had, but he seemed satisfied with what he'd already gotten, and started getting dressed again. Suit yourself, I thought, as I pounded my older sister senseless. Well, more senseless.

Just then, Mark entered the room.

"Hey, what?" he demanded. "I thought it was my turn!"

I blanked him out as the pleasure overtook my senses. Kevin could deal with him. I was too busy enjoying the ride.

Then something happened I couldn't blank out. Ashley woke up.

"Hey... what..." she said groggily, her eyes fluttering open. Oh shit. We were in major, major trouble. I wanted to stop but I couldn't, my body was on autopilot, the pleasure was too great. I couldn't have stopped, WOULDN'T have stopped, for the world.

"What the fuck?!" she demanded, now totally awake. She sat up a little and shoved me. "You piece of shit, stop-!" But I still couldn't stop. She shoved me again but I stayed inside, pounding her like a jackhammer. Mark and Kevin were frozen with fear, I'm surprised they didn't get out of there, I would have.

But then something unexpected happened. Ashley started moaning as though she enjoyed it.

"Ah... That's actually pretty good... Mmmmm..."

I took this encouragement and went with it, slamming her even harder. This made her gasp, her tits jiggling as my thrusts rocked her body. I lowered my head to one of them, sucking and biting it.

"OOH! Josh, don't be so rough!" Ashley groaned. I didn't listen though, and only treated them harsher, raising my hand to squeeze and grip the other one as though I were wringing out a sponge.

"Wait, wait, let me get on top." she panted. This kind of confused me, but I soon realized what she meant as she slipped me out of her and laid me down on my back. Holding my cock straight up in the air, she got on top of me and slowly lowered herself down on it.

The second entry felt even better than before, as her snatch was hotter and wetter this time. Soon she began bouncing up and down on my dick. The pleasure was amazing, I was going deeper inside my sister than ever.

"You." she gasped after a few moments, pointing to Kevin. "Come here."

He did, standing right behind my head. Ashley reached into his pants and fished out Kevin's hard-on. She licked her lips and put it into her mouth, sucking it ravenously. Kevin gasped with surprise and started to moan, just as Mark had.

And speaking of Mark...

"Hey, when do I get to do something?!" he asked, even more frustrated than before. All three of us ignored him, his speech drowned out by our pleasure.

Mark didn't say anything, but a look crossed his face as though he'd just had an idea. Out of the corner of my eye, I saw him take his dick out of his pants and move around behind Ashley as she fucked me. He pressed the head of it against... her butthole?! What?!

Ashley didn't seem to think it was a good idea either. She took her mouth off Kevin's dick and said, "Hey, don't... I've never-" Her words were cut off by a scream of pain/pleasure as Mark dove his hard cock into her virgin ass.

"S-so tight!" he moaned. He allowed her no time to adjust to the sensation, and immediately began thrusting in and out of the older girl.

"OH yes, that's so good, fuck me!" groaned Ashley, before continuing to give Kevin head.

No one spoke for about fifteen minutes, unless you count moaning and groaning, as the three of us filled all my beautiful sister's holes.

Finally, Kevin let out a sharp cry and came in Ashley's mouth. She gagged on the quantity of cum and spit out his spurting cock, where he finished on her face and chest.

This sight finally pushed me over the edge. I cried out and fired eight huge shots of my seed into my older sister's womb. The sensation of my jizz filling her caused Ashley to have an orgasm herself, her pussy tightening and spasming around my twitching cum cannon while she screamed in orgasm.

When I finally finished after what seemed like forever, I pulled my cock out of her and backed away, exhausted. A large quantity of cum spilled out of her pussy as I vacated it.

"Are you sure we can't get you pregnant, sis?" I asked her, eyeing her sloppy hole with concern.

"P-positive." she gasped, out of breath. She lay on the floor, completely spent, as Mark finished up. Once he started moaning as though he was very close, he pulled his dick out of her ass and slid it into her eighteen-year-old pussy, filling her with yet another huge blast of jizz.

And that was it, it was over. All of us awkwardly cleaned up and got dressed.

"So, did you like it?" I asked Kevin.

"What do you think?" he grinned.

I laughed. "What about you, sis?" I asked her, but she just left the room without saying anything.

LATER

It was night time, and I was lying in bed trying to sleep. Kevin and Mark had already gone home long ago, and now I was just trying to get some rest for school the next day, still very exhilarated from what had taken place earlier.

However, Ashley's sudden departure made me worry. Was she mad at me? Was she going to tell mom? I really didn't want to get in trouble. Worse, was making someone have sex with you illegal? I didn't know. Could I go to jail? Needless to say, with all these concerns, sleep was very far away.

I heard wheels on gravel in the driveway. Ashley was home from cheerleading practice. I rolled over and tried to sleep, wondering if she'd already told mom and dad or if she was going to make me suffer waiting some more.

I opened my eyes when I heard my bedroom door open. Standing in the doorway was my sister. She was still wearing her uniform.

"Are you awake?" she whispered.

"Yeah." I said, sitting up. She came over and sat on the side of my bed.

"Josh, we have to talk." she told me.

"Sorry." I said. "I'm really sorry we made you have sex with us. Please, PLEASE don't tell mom."

"No, no, it's not like that." she insisted. "In fact... I kind of enjoyed it."

"Really?" I asked her.

"Yeah." she said.

"So you're not mad?" I asked, unable to believe it.

"Not at all." she replied. "In fact, to show there's no hard feelings, I'll still babysit you and your friends, whenever you want." She winked. "If you know what I mean." She got up and headed for the door. "Now get some rest, you've got school tomorrow."

I didn't say anything, my mouth just hung open in amazement as I watched my beautiful sister leave, unable to comprehend what she'd just told me.

My life was about to get very interesting...

-----------

So that's that. Next chapter will be up soon... Thanks for reading! :D