My Little Sister's Orgy

There I was, minding my own business in my room, when in walks my sister, Cali. She asks me if I have a minute and that she needs to talk to me about something kind of awkward. I said sure and she took a seat.

"James, I just want to know before I ask this, that you won't freak out and hate me. It's just a question, you can answer however you want."

"...ok...."

"My friends and I are throwing a little party. A private party."

"And?" I said, not getting where she was going.

She was really hesitant, and I was just about to the point where I was getting irritated.

"Just ask it already!"

"Ok. Well we are having an orgy... A SMALL orgy...nothing big" as if that helped...

"What??! Are you out of your mind? Aren't you a virgin?"

"Yes, but its something my girlfriends and I have been talking about for a while now, and we all figured that the best way to lose our virginities is to do it together. we've thought long and hard about it and if you think about, it's not as crazy as it sounds. We've finally made up our minds, but we need...help."

"You're just trying to get disowned, aren't you?" I note.

"Well obviously, mom and dad can never know!"

Finally getting to the reason why I was being told I asked, "So why are you telling me?"

"So it's going to be me, Jessica, Ann, and Kristin. We have one other guy so far, Greg, who we love and trust. But there aren't any other guys we want to do this with, and none of the ones we hang out with could keep their mouths shut. We don't want everyone finding out and calling us sluts."

"...So....you want me to help you find some guys?"

"Not exactly... We actually want you to join. Jessica specifically asked me to ask you. She is obviously into of you, you've known that for a while."

I sat there, shocked, not knowing what to say. Of course, her friends were super hot and I would love to be in their orgy. But an orgy with my sister? Wouldn't that be weird?

"I don't know Cali, that might be a bit weird with you and me you know? Plus, if dad ever found out I was in an orgy with you, he'd either beat my ass. And if any of my friends found out, they'd think I was gross."

"I know, I know. But no one will ever find out. We are all keeping this a big secret. And besides, it's not like I haven't seen you naked before. And same goes for you with me."

"What?" I said, confused by her tone.

"Oh come on... You think I don't know that when you come in the bathroom while I'm taking a bath to tell me I have a phone call, you're not staring and drooling at my tits?"

"Uh..." not knowing what to say to that. "I'm sorry...?" I said, embarrassed and turning red.

"It's fine. I have managed to catch a glimpse of you naked as well."

"When?"

"Well let's just say you don't always have your door closed all the way when you shower. And once I saw you and Kelly having sex."

"You've seen me having sex?!?!"

"Yeah, and I won't lie I watched for a while."

I didn't know what was going on. This typical day had turned into my sister inviting me to an orgy and then telling me how she has watched me have sex.

"Ok." I said not knowing what else to say. "So if I do it, you promise that no one will ever find out?"

"Promise."

"And you promise it won't be weird between you and I?"

"Promise"

"Well, ok fine. But I better not hear about this getting out. I'll deny it. And if dad ever catches wind of this, you deny it with me. To the grave!"

"I will, I promise. But nothing it going to get out. It's our little secret."

With that she giggled, and sort of jumped for joy, hugged me, gave me a kiss on the check and ran out.

So the night finally came. We had waited until the end of the month. It was that Friday and I had just gotten home. Personally I was really excited, because I always wanted had the hots for Jessica. Ann too, to be honest. I thought they were really hot, and I constantly jacked off to the image of fucking my little sister's cute friends. I was pretty nervous though, because I wasn't exactly sure how it would all work. But I figured I'd be the older guy in the room that the girls would trust and that I could act like I totally knew what was going on.

The girls came over around 9. The guy, Greg, showed up about a half hour later. We spent the time hanging out, drinking margaritas and flirting with each other. I was a little uncomfortable flirting with girls right in from of my sister, but I knew I would have to get past that quickly. When Greg arrived, we poured some shots and began to really get the party started. He was a skinny little Asian kid who I had only met once or twice but didn't really know. He seemed equal parts scared out of his mind and horned up.

We all sat on the sofa with our buzzes sufficiently high. One of the girls brought this adult party game where we basically drew cards that told us to complete a task. It was pretty dorky, but kind of fun. Kristin went first. Her card said to make out with another player. I gathered that her and Greg were somewhat of a thing and so it was no surprise when she went and sat on his lap and started making out.

Ann went next and had to lose her shirt. I liked where this game was going. Cali went next and had to take off an article of clothing from another player. She went over to Jessica and took off her pants. I was especially excited to see Jessica's perfectly shaped body, her legs exposed with all their beauty, and now nothing but a lacy pink thong between me and her virgin pussy. I had to lose my shirt...no biggie.

The game went on like that for a while. I had made more drinks for everyone and we were all having a really great time, laughing and flirting with one another. Some of the girls were topless, including my sister, but I didn't mind so much. She honestly had cute and sizeable breasts that she was still growing into. The game was kind of falling apart since one of them had a card that made them blow Greg. It was weird sitting there watching this guy was getting blown, but it it was also a major confidence booster as this poor kid's cock was about half as big as mine.

The rest of us were kind of bunched up, with my sister on the outside, playing truth or dare and drinking while Kristin had Greg in her mouth. I was making out with Jessica at one point, which was a lot of fun, when I noticed Ann unbuttoning my pants. It was a bit weird with my sister right next to me, but I couldn't back out now.

Ann pulled out my dick, made some comment about how she had never seen a dick that big (but honestly, how many had she seen?....) and then started sucking. I couldn't believe this all was actually happening. I was actually going to have an orgy with these people. Ann was brilliant with a cock in her mouth. Her tongue seemed to play with every inch of me, and I was worried she'd suck every last drop of cum I had to offer out of my balls too quickly!

But Jessica was getting antsy. She pushed me backwards, down on my back, and then she lifted her leg over me and sat on my face. I ate her out while Ann blew me. I think my sister must have been over with Kristin and Greg doing something. I couldn't exactly see. After a while, Jessica got up and I was really excited to find out what was going to happen next. But as she got up, I looked down and was shocked to find out that Ann was no longer blowing me, but that it was my sister with my dick in her mouth!

I jumped up quickly.

"Cali, what the hell?! Not cool!" I said.

"I'm sorry James, I just figured we were all having fun, and it wouldn't matter."

"It does matter!" I said.

Just then Jessica intervened and told my sister to lie down for a second. She then whispered in my ear, "Everything we do here tonight is never going to get outside these walls. We are all just people exploring each other's bodies tonight, and your sister deserves to be treated like a princess. Why don't you just start by eating her out."

"My sister?!?! No!"

"Don't be so upset, just try it. If it weirds you out too much, then stop. But if you do it, not only will I fuck you here, in front of everyone, but I'll also come to bed with you and let you fuck me all night long."

I was really hesitant and didn't want to do it, but damnit if that wasn't a great offer....and everyone kept pushing me to. I figured it wouldn't be the end of the world, so I got down on the couch and put my head between her legs.

I was staring directly at my sister's vagina, clearly dripping wet from all the activity. I couldn't believe I was actually considering putting my tongue in her. I waited for a moment, took a deep breath, and slowly pressed my lips up against her pussy. I pushed my tongue through her, moving apart her lips and exploring the ins and outs of her pussy. I was shocked at how amazing she tasted in my mouth. I was even more shocked that I wasn't stopping... I proceeded to do that for a while, while everyone else proceeded to play with each other. I feasted on Cali's wet pussy, licking and sucking her clit and making her jump and squirm and moan.

After a little while, she pulled my head up and kissed me, shoving her tongue into my mouth and trying to taste her juices. It was exhilarating. She then pushed me backwards and started to blow me again. Jessica began making out with me as I reached down and shoved two fingers inside of her.

"See? I knew you'd get into it." She said as she moaned from my fingers rubbing her G-spot. She then whispered in my ear, "Now I have to hold up my end of the deal."

And with that she moved my sister's head off my cock, and slowly replaced it with her wet pussy, sliding in effortlessly when mixed with my sister's saliva. I wondered if I should be wearing a condom, but that thought came and went. I was way too taken over with excitement to care about that and all I could focus on was Jessica bouncing up and down on my cock. She had the tightest pussy I'd ever felt. I'd had sex with a few different girls, and they were all tight and sexy as well, but something about Jessica's virgin cunt gripping my cock...the first cock it ever gripped...sent me over the edge. Ann and my sister started playing with each other with dildos and vibrators one of the girls had brought over, and Greg and Kristin were fucking on the other side of the couch.

Jessica and I fucked for a while, until Ann got jealous and pushed her off. "Ok, it's my turn" she said. On she climbed, one tight virgin pussy to the next. I couldn't believe the state of ecstasy I was in, and knew I would likely never surpass this peak ever again.

People started making their way to certain beds in the house. Ann and my sister went to her room, Kristin and Greg in the guest room, and Jessica and I went up to my room. When we were up there, we took a bath together, talked and sucked and fucked and then fucked a few more times before we fell asleep naked together.

It was easily the most eventful and exciting night of my life. The next day, everyone left, and it was just me and my sister left to clean everything up.

"Thanks again for last night" she said.

"No worries. Honestly, thank YOU. I had a great time. Jessica is...amazing."

"So what'd you too do up there all night?"

"Don't worry about it" I said in a joking manner.

"Fine, don't tell me." she laughed. "Ann and I could hear you two all night any way!"

I laughed and said "Sorry about that. I didn't know she would be such a screamer."

We had a laugh and kept cleaning up.

Then she turned to me and said, "You know, I have never had such an intense orgasm as last night when you ate me out."

Feeling a bit awkward I responded, "Oh good. I'm glad to hear it."

"But I have to admit, I was pretty jealous when Jessica started fucking you."

"Well we probably went to far with giving each other oral anyway. So it's probably good we didn't go any farther."

"I guess. But I'd be lying if I said I didn't think about it. I really wanted to have sex."

I was a little confused and didn't know how to respond, and said, "Wait, did you not fuck Greg? I though the whole point was for you to lose your virginity?"

"Kristin offered to share him, but I honestly just wasn't interested in losing my virginity to him after all. But Ann and I had some fun of our own."

I didn't quite know what to say. I felt bad, but was also confused as to why she would only have two guys at her lose-my-virginity orgy: one that she didn't want to fuck, and other that was her brother...? I opted to say nothing about that, and we sort of drifted off topic.

The rest of the day, however, she found ways to try and turn me on. She walked out of her room in just her towel after her shower, and then took it off right in front of me. She also even came up to me and kissed me on the lips, putting her hand on my crotch and said "I miss this!" I didn't know what to say. I clearly enjoyed it, but I also knew it was wrong.

That next night, her and her friends went to the mall or something and I was out with the guys. I wanted to tell them everything so badly, but I couldn't. When I went home, I turned out all the lights, made sure my sister was home safe, locked up the house, and went to bed. It wasn't too long, however, until my sister came into my room and crawled into bed with me.

I didn't know what to think. I was fighting different emotions. I knew I should tell her to leave, but at the same time I really wanted her to stay. I knew how good her blowjobs were and I really wanted another taste of her sweet pussy. But was she here for something more than that? Would that be ok? Would it be ok if her and I hooking up became a habit, outside of just that one secret night? Obviously not... but the more appropriate question was, did I care?

I guess the answer was no because when she got in and under the covers, she kissed me. We laid there kissing for some time, exploring the movements and tastes of each other's mouths. I was in heaven. I let my hands explore her whole body, eventually making their way inside her dripping wet pussy.

"Wait" she said.

"What?"

"Let's not do this yet. I'm so awake. Let's do something fun."

"Like what?"

"Let's go skinny dipping."

Not one to pass up something like that, I said sure and we went into the back yard. We stripped down and hopped in. I loved the way it felt swimming completely naked, the complete freedom and softness of the water. We couldn't help but giggle the whole time, knowing that this was crazy.

"You think the neighbors will see us?" she asked.

"It's too dark. They would never know who it was."

Then she swam up to me and wrapped her legs around me, holding herself up with her arms around my neck. It was an image I would have totally seen being in with a girlfriend, but never imagined it would be with my sister.

We spent a little bit more time in the pool, but we could barely hold in the urge to start having fun. I was still worried whether or not I should have sex with her. My gut kept telling me no, but everything else kept pushing me towards yes.

We toweled off and went back in the house.

"I'm hungry" she said.

"You want me to make you something?"

"Yes please."

We were butt naked in the kitchen, she was sitting at the counter watching me, and I was making her a grilled cheese. We were having quite a fun time. It was all pretty harmless. No sex, just swimming and hanging out... in the nude.

The all of a sudden, it was no longer harmless. She walked over, got down on her knees in between me and the counter, and put my dick in her mouth. I wasn't expecting it so I was not quite hard and ready. But it was still amazing watching her suck up my flacid cock and get it erect. It didn't take long for me to get hard and she was really going to town on me, licking and sucking as much as she could. I honestly thought I was about to blow after about a minute, it was so good. I told her that.

"I don't want you to cum yet."

"Ok" I laughed, frustratingly.

I put her sandwich on a plate on the table and she bent over the table to eat it. I thought I would have my fun now. I snuck up behind her, got down low, and started licking her pussy from behind. I accidentally licked close to her asshole, but she really liked it and, honestly, it turned me on. I began eating her out, hearing her moan as she attempted to eat her snack. I then stood up, hugged her from behind, reached around to play with her nipples, with my dick poking her butt, and began to suck on her ears and neck. She was struggling about because it tickled her and I was wrestling to keep her still. And that's when it happened...

From behind, as we were wrestling about, I felt my dick become surrounded in a tight warmth. She yelped a little and we just stood there, not moving, trying to understand what just happened. It had accidentally slipped into her pussy. It was wet from her sucking on it, plus her pussy was dripping wet from me eating her out, and it just happened.

"I'm so sorry" I said and began to pull out.

As I did, she moved backwards, pushing it in even more. Then she did it again. There were no words spoken, just a slow in and out, in and out. Her breathing started getting heavier, as did mine. I grabbed her waist and used it to get my own rhythm going. It got stronger and stronger. Her moans got louder and louder. Until I was quite literally pounding my sister as she was hunched over the kitchen table.

I was gone, lost in ecstasy, that I didn't notice myself about to cum. I shoved one final thrust into her and emptied my load deep into her pussy. I felt her pussy tense up and erupt with a wetness of her own, and I could tell we were sharing an orgasm. It was one of the most amazing moments.

"You came in me!?!" she screamed.

"Fuck, I'm so sorry."

I couldn't move. We stayed in that position, catching our breath, until she turned around and kissed me.

"Let's go to bed" she said.

And with that, I picked her up and carried her in to bed. We fell asleep in each other's arms, sweaty and naked.

I woke up with a major hard-on the next morning, and since we were spooning, she felt it and it woke her up too.

"I can take care of that" she said. And she went under the covers, sucked on my dick for about a minute, rolled me onto my back, and then climbed on. It was first thing we did when we woke up, and I will never forget the image of her straddling on top of me, bouncing up and down, her hands in her hair, her breasts bouncing with her, the morning light dancing across her smooth skin. She looked like an angel.

After sending another round of swimmers straight up into my sister's uterus, we took a shower, went out to breakfast, saw a movie, and came home to go swimming again. Every so often throughout the day we would get horny for each other and do something about it. She blew me in the theater. I ate her out by the side of the pool. She even had me stand next her on the toilet so she could keep sucking me off while she pissed. It was wild!

We wouldn't have the house to ourselves again for a while, so we knew these chances would be few and far between. We made the best out of the time we had. We made love a couple more times that night, until we heard keys in the front door and we quickly got off each other and got into our own beds. It was the best weekend of my life.

Lucky for me, that would not be the last time her and I would play in that way. We had many more exciting stories after that. The craziest was probably the time we screwed around on the airplane bathroom on a family trip. Or maybe it was the time my mom walked in on me on top of my sister, screwing her from behind, but it was dark and she didn't know it was her daughter I was screwing, apologized awkwardly for interrupting and left. Or maybe it was the time we got caught by our cousin one Christmas when my sister insisted on blowing me under the deck where everyone was gathering!...but those stories will have to be saved for another time.