Sibling Truth or Dare Club

I woke up early Sunday morning and felt a hand on my boob. I glanced over my shoulder to see my brother still fast asleep. I had a wicked thought.

I wiggled away from his prying hand without waking him and slowly crawled down lower on the bed. I stuck my head under the covers and was excited to see that Jeremy was already hard. Perfect. As careful as I could without waking him, I lowered my head and took him into my mouth. I tried to go nice and slow to see how long I could do this without waking him up. After a few seconds I heard.

"Ohhh. What? Ange? Is that you?"

"Mmmhmmm!" I moaned without removing him from my mouth.

He went to respond, but I took him all the way into my throat, and he just groaned a response instead. I kept working him in and out, swirling my toungue around his head before taking him all the way in again. It didn't take long before I felt his hand on the back of my head, and he exploded into my throat.

I climbed up and gave him a beautiful cum filled kiss good morning.

"Well, that's a pretty decent way to wake up!" He said.

"I thought you might like that." I responded.

We resumed our kiss and even engaged in a little heavy petting. After a few minutes, we got up and decided we needed to have a shower. Of course, to save time, we decided once again that a mutual shower would be the best way to go. We might have also had sex again in the shower. I could get used to this.

* * * * *

Normally we'd be expecting our parents to come back on Sunday afternoon, but this being a long weekend, we had an extra day; they wouldn't be back until Monday afternoon.

After finishing our shower and getting dressed, we had made our way into the kitchen to get some breakfast. I got an email.

"Hey lovebirds. You two free for a game today?" Caleigh had sent us an email.

"Of course. This evening works for us." I responded. I needed a little bit of a break before what I could only imagine was going to be a pretty sex-intensive game.

It was nice just to hang out with Jeremy for a while. We ate breakfast, watched a movie, went out to pickup a couple of things, and just had a lovely afternoon together. It was interesting being in public because no one had any idea what had just transpired between the two of us.

* * * * *

Around 7pm, we logged in and joined Caleigh and Kyle's game.

"Hey!!!!!" Caleigh was especially chipper. "Ok, so tell us everything."

We proceeded to tell them, in great detail, about our first time together. About how amazing it felt, about how Jeremy came inside me. We told them about the morning blowjob and the shower sex. Everything. I really felt secure talking to Caleigh and Kyle about anything. They were the only people who knew our secret, and we knew theirs.

"OK, let's get this game started." Caleigh stated. "We'll let you ask us first. And we'll start it off easy by choosing truth."

"How long have you two been having sex?" I blurted out. I had so many questions to ask them, but that seemed like a good place to start.

"Almost three years now." Kyle responded. Then he gave Caleigh a kiss on the lips.

"Truth or Dare?" Caleigh asked.

"Truth." I responded.

"OK, these ones for Jeremy. Before the two of you started playing these Truth or Dare games, did you think Angela was sexy? Had you thought about her sexually?"

Jeremy's face turned beet red.

"Um, that's a hard question to answer. I've obviously always been aware of how good-looking my sister is. But I had never thought about doing anything sexually with her. But I had checked out her tits and her legs a few times, if I'm being completely honest."

It was my turn to blush. I felt much the same way; I've been aware of Jeremy's sexiness forever. But I wouldn't have thought any of what has happened would have been possible.

"Truth or dare?" I asked back.

"Truth!" Kyle responded.

"Have you ever played Truth or Dare with any other siblings?"

"No, you're the first. We have role-played incest-themed scenarios with other couples, though." Caleigh responded.

"Don't forget about Mike!" Kyle interrupted.

"Holy shit, I totally forgot about that." Caleigh responded. "OK, so there was this single guy, Mike, who we were playing a game with. It got pretty wild, and we kept trying to one-up each other. I dared him to accidentally send his mom a dick pic. At first he chickened out. He took the picture but couldn't send it. And we just moved past it. But then a few days later he came back online and told us that he hated that he chickened out of a dare. And that he couldn't live with himself if he didn't do it. And so he told us that just that day he did it. He sent his mom a dick pic and then told her it was an accident and meant for someone else. We were totally blown away that he had done it, but that wasn't even the wildest part. A few days later, he came back on the app and told us this whole crazy story about things between him and his mom, but they ended up fooling around. They didn't end up having sex, and eventually he ended up meeting someone, so they had to stop. But they did fool around together for a little while, which was pretty hot to hear about."

"Wow. That's pretty wild." I said.

"Truth or dare?" Caleigh asked.

"Dare?" I said with a shrug while looking over at Jeremy.

He nodded in agreement.

"OK great." Caleigh said. "One day we'll give you the full story about how we got together and everything, but I'm horny as shit right now. And I've been dying to watch the two of you fool around some more. So since we already saw you give your brother a blowjob Angela, fairs only fair, Jeremy, we dare you to make your sister cum; we dare you to go down on her."

We didn't waste any time; we repositioned things so that I was sitting on the couch with my butt right at the edge; I was sort of angled to the side, and the camera was pointed directly at my pussy. And Jeremy came in from the other side so that Caleigh and Kyle could still see most of what was happening.

Jeremy didn't waste any time; he got to work attacking my clit right away. Holy shit did that feel good. It wasn't going to take long for me to cum. He added two fingers and began sawing them back and forth. As soon as he added a third finger, I came instantly. I threw my head back, shut my eyes, and let my orgasm wash through me. I tried to plead with everyone to let this dare go on a little longer. But a dare was a dare, and he was only dared to give me one orgasm, so we stopped there for now.

"Ok, you two. Your turn. What do you choose?" I asked as we re-positioned ourselves back into the middle of the screen.

"Dare, of course." Kyle stated emphatically.

"I dare Caleigh to fist herself again. That's just so hot to watch." Jeremy said enthusiastically.

He wasn't wrong. It was super hot to watch.

And for the next few minutes we watched as Caleigh fisted her pussy over and over again. It was amazing just how much she could twist her fist around inside herself. Not only could her pussy accommodate her hand like that, but she was super flexible and able to get her arm into just the right position to make it all work. My pussy got even wetter just watching her do that to herself.

After taking a few minutes to get cleaned up, Caleigh said she had a dare for us.

"These ones are a little freaky. So I'll give you the option of backing out if you don't want to do it. But I would really love to see this. Angela. I dare you to give your brother an orgasm."

I was about to tell her that wasn't very freaky at all when I realized she wasn't finished speaking.

"Without touching his penis." She finished.

"Huh?" Jeremy responded, pretty much speaking for both of us.

"If you manipulate a man's prostate, you can make him cum without ever touching his penis." Caleigh informed us.

Oh. Now I realized what she was daring us to do. That was pretty freaky. I had to admit though, I really hoped Jeremy wouldn't back down from this.

"So if ol' sister dear there takes two or even three digits and sticks them inside you brother dear, you'll have one of the best orgasms of your life." Caleigh continued.

"Wow. That is pretty wild." Responded, my brother. "If you had told me a few weeks ago that someone, let alone my sister, would be fingering my ass live on camera for a couple to watch, I would have told you were crazy. But what the hell? We've come this far. Give us a few minutes to get things ready."

We left the living room to get a few supplies. As we were gathering things, Jeremy started to have second thoughts.

"Do you trust me, Jer?"

"Of course."

"Then trust me, this is going to be great. We can stop at any time, but it's going to be amazing."

We brought the laptop up to my room and positioned it facing the bed. Jeremy got on all fours with his cute butt in the air. I asked Caleigh and Kyle if they were ready, and Caleigh was super ready and excited to say the least.

So I crawled up behind my brother and started to rub his hips and his butt cheeks. I grabbed the tube of lube and squirted a tiny bit on one of my fingers. I then applied it directly to his ass and started to massage the opening. I figured I'd start slow and give him some time to get used to the feeling.

"Oh fuck, that's so hot." Caleigh yelled from inside the computer screen.

I added a little more lube and spread it all around my middle finger. I placed it back at the entrance to his asshole and applied a little bit of pressure.

"Oh fuck." Jeremy half yelped.

He sounded a little distressed but gave me a nod to continue. I kept applying pressure until my whole middle finger was inside him. I left it there to allow him a second to adjust. Then I started working it slowly in and out of him. At first I could see the tension in his body, but he slowly started to relax.

I added a little more lube and then really started to work my finger around inside of him. He was really starting to enjoy himself, so I asked if he was ready for another finger. He agreed without saying a word. I added even more lube and then inserted my index finger alongside my middle. I was now fingering my brother's asshole with two fingers. Holy fuck was this hot. I didn't think it would be this big of a turn-on, but my pussy was on fire and dripping down my leg.

I started to fuck my brother with my fingers, and he was moaning quite loudly. I pressed in deep, and judging by his reaction, I was pretty certain I had hit his prostate. I kept massaging that spot over and over, and he was clearly enjoying it. I glanced over at the screen to see Caleigh and Kyle watching intently. Kyle was playing with Caleigh's tits as they watched.

I asked Jeremy if he felt like he could handle a third finger, and he said yes. I told him to flip around and lay on his back. As he laid back down, his erection was sticking straight up. A stream of pre-cum was hanging from the end. He was leaking pretty well at this point. I added even more lube and slowly pushed three fingers inside my brother. He was taking it like a champ. He gave a slight grimace when I first put them inside of him, but then he just closed his eyes and let me go to work. I was really working my fingers back and forth, paying extra special attention to his prostate. I could tell he was getting close.

"Oh my god. I'm gonna cum." He yelled out.

And I'm not sure why, but at that moment I jammed a fourth finger into him, and that sent him over the edge. Without me touching his cock once, it started spasming, and cum flew out and landed on his stomach. I kept pumping into him, and each time I pumped, his cock seemed to lurch, and a little more cum came out. Finally he stopped cumming, and I slowly allowed my fingers to fall out from inside him.

I crawled up and gave him a huge kiss. He was covered in sweat and glowing in post-orgasm bliss.

"Holy fuck. That might be one of the sexiest things I've ever seen." Caleigh said. "Why don't we take a 30-minute break? You guys can get cleaned up, and then we'll resume the game in a little bit. That is if you're still interested in playing."

"Fucking right, we're still interested in playing. Payback's a bitch." Jeremy responded with a wicked grin on his face.

"Bring it." Caleigh stated defiantly.

And so we disconnected and took a few minutes to just lay in each other's arms before cleaning up and getting refreshed. We got ourselves a drink and relaxed together in bed until the 30-minute break was up.

We gave each other a quick kiss, OK, maybe a little longer than a quick kiss, then logged back in.

"Alright Caleigh. Your turn." Jeremy jumped right in, not wasting any time. "I'll assume the two of you choose dare. Kyle, I dare you to fuck Caleigh's ass until you fill it with cum."

"Is that all you got?" Caleigh chirped back, already stripping off her clothes and climbing onto the bed.

Kyle grabbed the lube from the bedside table, spread it on his cock, and then, in one smooth motion, buried himself fully in Caleigh's ass. This wasn't the first time a cock had been up there. Jeremy was going to have to work harder next time if he really wanted to push the envelope. Although I wasn't complaining. This was still pretty sexy to watch.

They both got into it, and a few minutes later Kyle was pumping Caleigh full of his cum. When he was finished, he grabbed the camera off of the screen and proceeded to give us a close-up of Caleigh's cummed-filled ass. He worked a few fingers in and out to show us his work.

They took the next few minutes to get cleaned up, and once they were ready, we resumed our game. It was our turn to accept a dare. I think we were done with the truths for the night.

Once they were ready, Caleigh said, "I know we were trying to one-up each other just now, but I just really want to watch the two of you have sex. Angela, I dare you to ride your brothers dick until he cums inside of you."

Phew. This would be easy. We refocused the camera, and then I climbed on top of my brother. I reached down and lined up his erection, and then, as hard as I could, slammed myself down on top of him. He gave me a bit of a strange look, but I just smiled, put my hand on his chest, and then proceeded to ride him as wildly as I could. Fuck did his cock fit perfectly inside of me. I rode up and down on his shaft over and over again. He had just cum a little while ago, so I knew this was going to take a little bit of time. I did not mind one bit.

I kept riding him through two of my own orgasms, and then eventually, just as I thought my legs couldn't handle anymore, Jeremy announced that he was going to cum. I felt the warm blast deep inside me, and it triggered a third orgasm for me.

"I am down with almost every kinky thing that anyone can think of. But I do have to say watching a brother and sister have straight-up sexy is so fucking hot. I know I've been a part of doing that for a while myself, but watching you two go at it is just soooooo sexy." Caleigh stated as we were getting things reset in the background.

It was my turn to issue a dare. "Caleigh. Do you own a strapon?"

"Yep." She responded with a big grin on her face.

Kyle didn't seem quite as excited at my question.

"I would love to see you return the favour and fuck Kyle's ass for a while."

"That would be my pleasure." Caleigh said.

I don't think Kyle was actually that upset at the prospect. Caleigh had to go digging to find the strapon but when she found it, it was bigger than I expected it to be. It wasn't the biggest dildo I had ever seen, but it was pretty close to being as big as Kyle's own dick was.

She lubed it up, and then with him on all fours, she pushed forward and sunk the whole dildo into his ass. She slowly started picking up the pace until she was fucking him at a pretty steady clip. Despite his earlier trepidation, he was getting into it now. Caleigh was really enjoying this, and I had to admit I was too. I started to play with my clit a little bit while I watched the siblings going at it. It didn't take long before Kyle exploded all over the bed. Caleigh slowed down and then removed the dildo from his ass. He was gaped pretty wide open as she pulled the dildo out.

They spent the next few minutes pulling themselves together before they sat back down and Caleigh issued her next dare.

"I think Jeremy needs a rest for a minute, so this one is for you to do alone, Angela." Caleigh stated. "My dare is for you to take that little hand of yours and to put on a little fisting show for the three of us. I know you can do it. Jeremy can help push your hand in the last little bit if you need to."

Old me might have freaked out right about now. But after everything we've done these past few weeks and how wet my pussy was at the moment, I didn't even hesitate.

I took a page out of the playbook from one of Caleigh's earlier performances and held one finger up in the air. Then I proceeded to work that finger in and out of my pussy. Then I held up two fingers. And worked them in and out. Then three. Then four. And finally I held my whole fist up in the air. I curled my middle finger up and pointed it at Caleigh with a big grin on my face. Then I tucked all my fingers together and proceeded to work my entire fist inside of myself. It took a little bit of effort, but pretty quickly the whole thing just popped inside. I was still full of Jeremy's cum from earlier. That combined with my own juices made it pretty easy for my hand to pop right in.

"Yes, you fucking slut!" Caleigh screamed. "You are a goddess."

I would have smiled at that comment, but I was too caught up in the feeling of my whole hand inside my pussy. I felt so full, but it really felt amazing too. I was able to work it in and out of myself much better now on my own. I didn't think this would ever be possible, but I was fisting myself like a seasoned pro.

"I know you're doing great on your own there, Angela, but I would love to see Jeremy help a little. Just for the visual. Jeremy, grab her wrist and help a little."

"I have a better idea." Jeremy stated.

He then proceeded to grab my wrist; at first I was confused because that's exactly what she asked him to do. But instead of helping my fist myself, he pulled my fist out of me. I was confused until I felt his fist taking the place of my own. My flung back as my brother proceeded to fist me.

"Oh my god, the two of you are amazing." Caleigh stated.

Jeremy began to pick up the pace and started ramming his fist in and out of me. It felt amazing. He was pumping and twisting, and I was in heaven. My whole body started to tingle and then I felt my orgasm washing over me. His fist was now completely leaving my body and then slamming back into me with each thrust. I came so hard and actually squirted all over his hand. He started to slow down, and I grabbed his wrist and just held his fist inside of me. I was breathing very heavily and slowly let his hand drop out of me. I felt empty at first, but I was so sensitive I needed to stop.

"Well, that was quite the performance all around by all of us, I do have to say." Said Caleigh. "We are one fucked up group of siblings."

"I don't care how fucked up any of this was; this was the hottest and sexiest night of my life." I replied.

"Hey Angela and Jeremy?" Caleigh asked.

"Uh ya?" We both responded.

"I think we're all just about worn out for the evening. But I have a homework dare if the two of you are up to it. No pressure if you're not."

"You know we can never turn down a dare." I responded.

"Ok. That's amazing. But that part still stands; if you don't want to do this, you don't have to. So my homework dare is. If you're willing, we'll send you plane tickets, and we dare you to travel here, to our town, and to have a real, in-person, 4v4 game of Truth or Dare with us."

I swear I felt my pussy get even wetter when she said that.