Sleepover

When I was 20, my sister Kendall had a slumber party that I will never forget. How does my sister's slumber party with her friends affect me, you ask? Here goes...

*

First of all, I was still living at home during this time. Kendall was 19, just turned, and all her friends were the same age I think. I felt they were all too old to be having a slumber party like a bunch of little girls, but Kendall always did stuff like that. She had very immature friends in my opinion, but she just really liked having fun I guess. I remember that I hated being home when her friends were over, because they always teased me mercilessly. I tried to hide but they always found a way to pull a prank on me. Usually it involved me losing all my underwear or something stupid like that. Now that I was older, and her too, I figured they would cut it out and forget about me.

Well, I had just come home from work that night and forgot that she was having her friends over. I worked nights while I was going to college, so all I wanted was to take a shower and relax. It was almost midnight, and I had assumed Kendall was the only other person home. Our parents had left for the weekend, and she figured it was the perfect time to have her gal pals over. I tried to be quiet, but her friend Lilith's car in the driveway told me there could be trouble tonight. I didn't hear them at all, so I just went for the shower and left my dirty clothes on the floor.

As I was showering, I thought I heard something so I peeked my head out from behind the curtain. I didn't see anything so I finished and quickly grabbed a towel. I wasn't even going to dry off in here, I just wanted to get to my room and lock the door. I wrapped the towel around myself at the waist and didn't bother to grab my dirty clothes. As I walked down the hallway to my room, I thought of nothing but having the whole weekend to relax. But just before I made it to my room, someone stepped out in front of the door.

It was Madison, one of Kendall's friends. A cute little thing to be sure, but she was blocking my way and I didn't want to mess around with her right now.

"Hey Kevin," she said, smiling brightly. When I realized that she was dressed only in a tiny little pajama set with short shorts and a thin tank top, I was caught a bit off guard. Her tight little body looked amazing, and her fidgeting made her boobs bounce just a little.

"Uh, hey..." I replied.

"Can I ask you something?" she said with a cheerful but quiet voice.

"What?" I sighed, knowing that this was some kind of prank. Plus I was almost naked, so this was not a good time for me to have to run after her or something if she was trying to steal my underwear again.

She looked a bit nervous. "The girls dared me to play a trick on you, and I want them to think I did."

Ok, where was this going? "Uh huh...?" I said.

She stepped forward and she was inches away from me. "I'm supposed to flash you," she giggled.

"And why are you telling me this?" I asked suspiciously. This must be just some part of a much larger prank.

"Well..." She looked sheepishly down at her feet. "I just kinda feel bad is all, cuz I know you hate these jokes we play on you."

"Well to be honest..." I wanted to tell her that I did indeed hate them, but they never went so far as to flash me before, and she was looking mighty hot in that little two piece outfit.

"Yeah?" she asked when I trailed off.

"I'm just really tired and I want to go to bed."

She mock frowned at me. "But I need to tell them that I succeeded, don't I?"

I glanced around. "You mean they're not watching us right now?"

She shook her head. "They're all downstairs. Can I let you in on a secret?"

I just nodded dumbly.

"All of us are supposed to flash you, it's a competition. Except for Kendall of course. But whoever does it first wins. I've been waiting here by the bathroom for a while now."

"That sounds silly," I said, trying to hide my smile.

"I know, it is. That's why I'm talking to you about it first."

Now you have to understand, Madison is a very hot girl. All of my sister's friends are. I know two buddies that have personally fucked this little beauty, and they both attested to how much of a minx she was. Plus, I could see for myself at the moment. So I wasn't really going to complain that I was stuck here talking to her.

"I was thinking..." she began, and somehow got even closer to me. "...that maybe I could just show you my tits right now, and you can look at them all you like, and I'll just tell them that I flashed you and ran off. It'll be our secret."

My towel shifted a bit as my loins stirred, and I just kinda stared at her while my mouth fell open a bit. She smiled and stepped back, and then reached for the hem of her pajama top. She began to lift it, but stopped at just above her stomach.

"Is that ok?" she asked, expecting me to say something probably.

"Uh, yeah. I guess so."

Madison went really slowly, barely exposing the underside of her boobs to me, and teasing me just a bit. But then she jerked her top up and left it hiked up over her chest. Her tits swayed gently out in the open, her nipples poking out as if to emphasize their presence. I was frozen in shock, I couldn't believe she was showing me her tits right here and now. I had to hold my towel at my waist, but there was no hiding my boner.

She laughed. "So you like them?"

I nodded, but my eyes never left her rack. She was a nice C cup at least, and they looked very firm and soft. I saw her eye my package, and then she bit her tongue in a lustful expression. We just stared at each other, and I wasn't about to say anything or breathe in case it would shatter the moment. But we both heard a creaking sound, and Madison pulled her shirt back down.

"Later, hon," she said, and brushed her hip against mine as she walked past me.

I hurried into my room and shut the door. I didn't know how to feel about what just happened. Was she really coming on to me, or was this an elaborate prank? You never knew with my sister.

I went to change into my night clothes, but when I opened my drawer, every single pair of my underwear was gone. Also, my pants and every pair of shorts I owned. All gone, probably hidden somewhere I would never find. They had never gone this far before. It was a good thing I didn't have school tomorrow, or else I would be pissed. But I was actually kind of intrigued, with the slightly sexual element that this game was taking. How could my sister be behind it, though? She had never gone beyond underpants theft before now. Was this something Madison was doing on her own?

I figured I'd wait until morning, and hopefully they would all be gone so I could search for something to wear. So I crawled into bed and idly thought about Madison's tight little body and her glorious titties while I touched myself until I fell asleep.

**********

I awoke later in the night to the sounds of my door creaking open. Kendall's friends were so loud and obvious that it was pitiful. But I played along. I kept my eyes closed so I didn't know if Kendall was with them, but I heard giggling and whispering as they crept into my room. It might not have been all of them, but it was at least two. I knew Madison was here, and Lilith, and probably Trina too. They were the usual group.

I was lying on my back, but there was moonlight coming into my room so I didn't want to chance opening my eyes or turning my head in case they could see me. I tried hard to hear what they were doing or saying, but it was too jumbled. I thought about waiting until one of them was close enough to scare, but then I felt the covers being moved back from my body. What the hell were they planning to do? I almost bolted upright when I remembered that I was naked, but then I calmed myself and remembered that they knew I was, so whatever joke they were playing on me, this was part of it.

"Are you kidding me?" I heard one of them whisper.

"Ssshh! You'll wake him up."

I couldn't make out who the voices belonged to.

"You've got to see it, Kendall."

Oh my god! My sister was one of the voices!

"I can't see my brother's penis!"

"Oh, who cares? You've seen one before..."

The second voice was Madison's, I was sure of it. What the fuck was she doing?

There was a pause. I felt very vulnerable lying there naked while they looked at me.

"Never one this big," I heard Kendall say.

"See? I told you."

What the hell? They were eyeing the size of my manhood? Why would Kendall go along with that?

"I wanna fuck him," Madison said.

My eyes shot open just then, but somehow they didn't notice. I quickly shut them.

"What? No! Why would you say that to me?"

"I want you to be ok with it before I do it. What does it matter to you?"

"It doesn't, but I don't wanna know about it!"

"Why not? Aren't I being a good friend telling you first?"

"You really like Kevin?"

I was listening to this strange conversation as a silent observer, feeling like even though I was right there, I was invisible to them.

"I like him enough to fuck him."

"So you're gonna seduce him right here in our house? With me and our friends downstairs?"

"It would be pretty wild, huh? We could make it a dare."

"You're crazy."

"Look, you can stay or you can go, but I wanna do this thing."

I heard Kendall move around a bit, but she didn't say anything. Had she walked out of the room?

"Fine, you little slut." It sounded mean, but there was this little hint of evil in her voice that said she was playing around. "I dare you to fuck my brother. With me in the room!"

I opened my eyes again, but this time I looked right at Kendall. She seemed surprised suddenly, like I had just appeared out of thin air. Madison followed her stare down to me, and just smiled.

"Don't pretend you weren't awake," she laughed. "You heard your sister, I've been dared to do something. And I never back out of a dare."

This was so wild, I wasn't sure whether to run out of the room or hide under the bed. Or maybe I was dreaming. Yeah, that had to be it.

Kendall just stood there, her devious smile returning. She was wearing t-shirt and panties only, but in the moonlight she looked kinda sexy. I felt bad for thinking that, but I had to admit she was a fox. I wished the lights were on so I could see more.

"What about Lil and Trina?" Madison asked, but she stood up on the bed and started to pull her shirt off in front of me for the second time.

"You want me to get them?" Kendall asked in amusement.

"No, but we have to make this quick." Her top was off, and she started to peel her panties over her hips. "That ok, Kev? I'll have to skip blowing you this time."

This time? Wow, that really turned me on. She was naked now, and slid down onto me. Her body felt so warm, and her fingers lightly grazed along my penis. This felt so weird with Kendall watching, but apparently time was of the essence so we had to fuck quickly.

"Pull out, Kevin," Kendall said. "I want the girls to see your cum on her."

Ok, that was the weirdest part yet. My sister wanted her friends to see my semen? Strangely, even though I felt really uncomfortable, I felt really aroused at the same time. Madison had crouched over my lap already, and was trying to position my cock at her slick hole.

"Feel free to get off," she said to Kendall. "If you can hurry."

No way, would Kendall really masturbate right here in front of me? I guess I was about to fuck in front of her, so what was the difference? Kendall sat right on the edge of the bed, and moved her panties aside. I couldn't see much, but I saw that she was fingering herself. Something was happening here that was beyond our inhibitions. This wasn't just a dare or a prank, this was a bunch of young kids whose parents had left them alone, and craziness was about to ensue.

Suddenly I felt hot as my penis sank into Madison's tight pussy, and she bottomed out on me in seconds. I forgot about my sister sitting next to us and playing with herself, and my instincts took over. Madison and I began to thrust into each other, and her grunting and groaning began to fill the room. For how brief it was, it was very intense. But I couldn't last long under these bizarre circumstances. I moved forward and pushed her onto her butt, and pulled out so I could spray her tits. She squealed in delight, and all three of us watched my thick jets of cum stream across her body. I jacked off quite a good load onto her, and then sank back down onto my pillow. Kendall just stared in amazement.

"That was so hot!" she breathed, her fingers still working her pussy.

There were footsteps outside my room, and the door was wide open. Madison grabbed her clothes and Kendall's hand, and rushed her out of the room. They both looked back at me and smiled, particularly Kendall, and then they were gone.

I breathed a huge sigh, and was lost in a haze of confusion and tingling. I ran a finger along my shaft and brought the residue up to my nose. It smelled sweet, like a hot girl's pussy. But why was I thinking about Kendall?

**********

Early the next morning, long before I was planning on waking up, I heard my door click shut. I blinked my eyes open to see Lilith standing there in her underwear.

"Um, good morning," she said, obviously very nervous.

"What are you doing?" I asked suspiciously.

She clasped her hands together anxiously and walked closer to me.

"I guess you should know that Madison told us what happened last night."

I turned a bit red, having temporarily forgotten about it. "Yeah..."

She came even closer, and I could see that her dark blue matching bra and panties were quite revealing. She was nearly as cute as Madison, but admittedly her body was even leaner and toned like an athlete.

"Well, then you should know that Trina and I are gonna try to seduce you too, to make us all even."

I felt my penis begin to rise beneath my sheets. "What?"

Lilith sat on the edge of my bed, right where Kendall had been masturbating herself hours before.

"I'm telling you up front so you will hopefully just let me do it and not waste time messing around. I really don't want to let Trina do you first."

Was I a piece of meat?

"Am I a piece of meat to you girls?" I said, a bit shocked.

Lilith smiled and ran her hand up my thigh through the sheets. I jumped, but her hand was not shy about finding my package.

"Ooh, Mads was right. You are hung."

"You really want to fuck?" I asked.

She nodded, her eyes wide with excitement. "Uh huh."

"How do I know this isn't some kind of joke? Are they all gonna burst in here and surprise me?"

Lilith answered by unfastening her bra and letting it fall off. "If they do, they're gonna get quite a show."

I was delighted to stare at her small but delicious titties while she pulled her panties off and flung them onto the floor.

"Can I...?" she said as she began sliding under the sheets.

Without any warning, she was on my cock and I was inside of her. She gasped at the intrusion, but I was frozen in shock. I never tired of that feeling when you first enter a girl's special place, tight and wet and sweet. She leaned forward and whispered in my ear.

"Cum on my face, that'll drive Trina nuts."

I responded by fervently humping and grinding into her, driving myself deep into her and pulling at her little hole as I dragged my dick back out, and then rammed it back into her. Her cunt was mine, and I planned on using it to the full.

Lilith's pussy was tighter than Madison's, if that was possible. Lilith's firm body was toned everywhere it seemed. Her thin legs gripped my waist tightly as she fucked me frantically. We didn't even have the breath to moan, we just grunted like animals. When he pussy started to melt and grip me like a vice, I knew she was cumming and I needed to cum too. I let myself go inside of her without warning, and when she felt my hot spurts she reacted by mewing into my ear and talking dirty to me, telling me she loved my hard cock inside of her.

The perfect moment was spoiled a bit though when an image of Kendall masturbating on my bed flashed through my mind. But I didn't feel guilty for having those thoughts. That barrier was being broken down by all of this depraved sexual activity. My sister's friends were total sluts!

"You didn't cum on my face," Lilith whispered, exhausted.

"Oh, sorry, you were just too wild and I couldn't hold back."

She smiled and ground herself into me, clenching my sensitive penis.

"That's what I like to hear," she said, and lifted herself off of me. My cum was dripping out of her pussy, and she ran her fingers across the trail down her thigh and brought them up to her cheek. She smeared a bit of my cum across her face and laughed as she turned and left my room, walking naked down the hallway and leaving my door wide open.

What could possibly happen next?

**********

I couldn't bear to go downstairs when I knew that Kendall and her friends were all down there. But I didn't have any underwear or pants to wear, so what was I going to do?

I went to the bathroom and started to wash up, when I heard the door close. I looked over to see Trish standing there naked. God, what was with these girls?

"You think I'm gonna let Lil win that bet?" she asked. "Think again."

"What the hell?" I was standing there naked too, but wasn't exactly aroused. "What is wrong with you all?"

Trish was the curviest of all the girls, and her bubble butt was her best-known trait. There was a rumor going around that she let guys fuck her up that curvy ass, so maybe I should turn the tables on this girl...

"Nothing is wrong with us, we just like to fuck," she answered.

"Well, if you wanna fuck me, you're gonna need to do something really dirty cuz I just fucked the shit out of Lilith. So it's not exactly gonna happen again easily."

"You got some lube?" she replied without hesitating.

I was caught off-guard even though that was exactly what I had planned.

"All I have is lotion."

Trish got on her knees and stuck her butt up in the air. "Smear it on and stick it in me."

Her boldness was actually very arousing, and despite my recent orgasm, my dick started to respond. I had never fucked a girl up the ass before, and had always wanted to. Trish's ass looked very tempting.

"You've done this before," I said.

"Many times, loverboy," she said devilishly, licking her lips. "I've never had a guy last more than a few minutes though, so this will be a treat."

I grabbed the bottle of lotion and started squirting it all over my dick, missing a few times and splashing it onto the tile floor. I also squirted some on Trish's tight little pucker hole, to which she squealed because of how cold it was.

"Enjoy it," she said softly. "Let my butt give you pleasure."

This girl could so from slut to sensual in the blink of an eye. My rock hard dick was pointed right at her asshole. The head of my cock rubbed against her, teasing her butt. I didn't know if there was supposed to be any trick to penetrating a girl's ass, but this girl seemed to be plenty experienced. Her sphincter opened around me and let me right into her cute butt. I grabbed her cheeks and drove myself into her, inch by inch.

She groaned deeply, enjoying the ass fucking for what it was, a dirty, forbidden act that made us both incredibly horny. The feel of her tight hole sliding down my shaft was incredible, and I could completely abandon myself to the pleasure it gave me without worrying about cumming too soon. I slid myself in and out of her bowels as deep as I could.

"How does that feel?" I asked, trying to sound sexy.

"It feels fucking filthy," she said. "I love it! God, it's so naughty..."