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.
