Sibling Truth or Dare Club Pt. 01

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A brother and sister join an online Truth or Dare club.
6.1k words
4.57
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Part 1 of the 6 part series

Updated 09/26/2024
Created 09/21/2024
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This is my first story. Feedback is very welcome. It's going to be a bit of a slow hitter but hopefully is well worth it in the end.

* * * * *

My name is Angela, and it all started out like any other story. One summer, me and a group of my friends were having a huge party. We started drinking, and eventually someone suggested we play Truth or Dare. I hadn't played since I was a kid and thought, what the hell, let's do this.

The dares were pretty innocent: eat a spicy pepper, eat a soda cracker, and then say the alphabet, run around the house screaming like a chicken, and the truths were pretty weak too: who was your first crush, have you ever stolen anything, etc. Just your regular run-of-the-mill truth or dare game.

About halfway through, when we had all had our fair share to drink, my brother Jeremy and a group of his friends showed up. Some girl that I didn't know instantly asked them if they wanted to join our game. I didn't think anything of it at the time and just smiled at him as he sat down across from me in the circle.

We proceeded to play for another hour or so, but at that point I was feeling quite tipsy and thought it was best to take off and head home for the night before things got out of hand. I got home about 1am and pretty much went straight to bed. I couldn't sleep though, and I was still awake when Jeremy got home a few hours later.

* * * * *

My brother and I have a fairly typical brother-sister relationship. We get along well. I had just turned 19, and Jeremy was 21. We used to hang out with completely different people, but this summer our friend group started to overlap more and more often.

I was sitting at the kitchen table eating breakfast when he came down the next morning.

"Hey Ange."

"Morning. That was quite some party last night, eh?"

"Ya, I had a blast. You missed it though, you know that Katie chick? She got dared to run across the field and back completely naked. And she did it. It was insane. The whole party lost their minds when she did it. I didn't think she was going to, but she barely hesitated."

"Whoa, that's pretty nuts. I'm sure you enjoyed that!"

"I'm not sure many people were complaining."

We proceeded to recap the party while finishing our breakfast, but it was pretty uneventful.

* * * * *

Later that night I was back in my room just flipping through my phone, bored. As I was mindlessly scrolling through TikTok after TikTok, an add suddenly appeared. I swiped past it, as I normally do with ads, but something caught my eye, and I went back to it. It was for a website, an app: Truth or Dare Club.

I laughed to myself; that's pretty funny. What are the chances? I swear these things listen to us all the time.

I went back to scrolling through videos and forgot all about the ad.

A few hours later, I was lying in bed trying to sleep, and the ad suddenly popped back into my head. I figured I couldn't sleep; everyone in the house was asleep. I might as well check it out and see what it's all about.

I downloaded it, and a pop-up appears: "In order to join, you must be invited by an existing member, or join with another person."

Shoot. Hmm, I wonder if Jeremy is awake.

"You awake?"

"Sort of. What's up?"

"Can I ask a favour?"

"I guess."

"Remember when we were playing truth or dare the other night?

"I downloaded a Truth or Dare app, and it says I need at least one other person to join."

"What?"

"I was scrolling on TikTok and this ad popped up for an app called Truth or Dare Club, and I couldn't stop thinking about it, so I downloaded it. But in order to join, you need to know someone who's already a member, or you need to join with a friend. Will you join it with me? You don't have to do anything; just accept my invitation and then go back to sleep."

"Ok whatever."

"Thank you. I owe you one!"

I typed in his email address and actually heard the ping coming from his bedroom. I got a notification right away that he had accepted.

"Thanks!"

"No problem. Remember, you owe me now! Lol. Have fun. Gnite."

"Goodnight!"

I created a profile for myself, blonde hair, blue eyes, 5'6, 19f, I chose not to say where we lived, I talked about some of my hobbies (photography, music), and I said I was just looking to have some fun, but nothing serious. Nothing serious? Lol, Ange, this isn't a dating site. Oh well. Let's see what this site is about.

I started exploring; it was sort of structured like old-school chat rooms, where you could join a chat room based on the types of games you were looking to join. And then within each room was a list of available games, how many people were playing, and if they were open to accepting new people.

The types of rooms were pretty standard: food-related, drinking games, PG only, NSFW, and extreme. I definitely wasn't feeling extreme but felt like having a little fun, so I went into the NSFW rooms. If it got too crazy, I could always leave.

I ended up joining a game with a couple, a man (28) Kyle and his girlfriend Caleigh (26). They were really nice and made me feel really comfortable right away. Something about them just put me at ease. We played for a little over an hour, and I actually had a lot of fun. It was pretty simple; I would get prompted Truth or Dare, and then once I selected, they'd type in their dare. At the end, they would give me a score from 1 to 10 based on how well I did the dare or how truthful I was. And then, at the end of the game, you were given a credibility score that lived on your account and others could see. That way, people could tell if you were playing the game faithfully or not.

They had a few good truths: What's the biggest secret you've kept from your parents? I told them about the time I got caught stealing at the mall but was able to get away with it.

I asked Caleigh a truth that had an interesting answer: Name one thing you'd do if there were zero consequences. She answered that she'd want to have a weekend fling with another woman!

Kyle kissed her on the cheek and said, "You can do that now without any consequences, as long as I get to watch."

At the end of the game, Caleigh agreed to take one final dare from me. I dared her to send me the last picture she took on her phone. Her cheeks went bright red. Lol, I got a little nervous about what was to come. But it ended up just being a shot of Kyle's naked butt.

I laughed and said, "Nice ass Kyle." He thanked me, and they logged off.

That wasn't so bad. I actually had a lot of fun. I'll have to find them again and play another game with them. I added them as friends, and they accepted right away. They sent me a message back and asked if I'd consider taking one last dare, a sort of homework assignment of sorts. I agreed. They sent me a link to a movie called 'Truth or Dare' and dared me to watch it.

I sent them a quick message accepting their dare and thanking them for the fun game, and then I logged off and went to bed.

* * * * *

I ran into Jeremy again the next morning; this time he was the one eating breakfast when I came down.

"Hot sauce, eh?" he said as he gestured to the open bottle of hot sauce I had accidentally left on the counter the night before.

"Lol, yep. That one sucked."

"But you had fun?"

"Ya, it was a blast. Hey, I actually have a follow-up dare I have to do and was wondering if you wanted to do it with me. It's pretty easy."

"Um sure, what is it?"

"I got dared to watch a movie called "Truth or Dare."

"Sure, why not? I don't have any plans for today."

"Great, I'm just going to go take a quick shower, and then we can watch it!"

"Sounds good."

* * * * *

Feeling super refreshed after my shower, I came down to the living room to find Jeremy waiting for me on the couch with a big bowl of popcorn. I sat down on the opposite end of the couch, opened the message from Caleigh and Kyle, clicked on the link, and started streaming the movie to our big living room TV.

The movie overall was pretty cheesy, but the truth or dare parts were really good. There were some great truths and even better dares. The movie started out pretty innocently enough but got quite sexual by the end. At one point, two of the characters were dared to make out with each other in front of their friends. They went at it pretty hard. I looked over at my brother just as the guy started making his way to second base, and Jeremy was squirming in his seat pretty good. I'm not going to lie and pretend that I didn't get a little excited myself watching all the heavy action.

The final scene was the wildest and even featured a little bit of nudity, something that did not go unnoticed by the guy sitting at the other end of the couch from me. It was a little strange seeing tits flash across the screen while sitting next to my brother, but I think we both survived.

* * * * *

Later that night I had joined a game with Caleigh and Kyle and had been playing for about 30 minutes when one of their truths was, "Hey, when you joined, who was the other person you joined with, or did you get an invite from someone?"

I told them it was actually my brother Jeremy who joined with me. I told them about finding the app and then needing a second person and that he had agreed to join with me. But as far as I could tell, he hadn't played or even explored the app yet. I did tell them about him watching the movie with me earlier.

Their next truth was actually them asking me what it was like watching a movie like that with my brother. I told them it was a little awkward, but we're both mature adults, so it wasn't a big deal.

After a few more rounds, I picked Dare, and Caleigh dared me to message my brother and ask if he wanted to join the game. I don't know why, but it was my turn for my cheeks to get bright read, but I agreed.

"Hey Jer. I'm playing a game of truth or dare on that app we joined, and this couple I'm playing with just dared me to invite you to play the game with us. Do you want to?"

"Sure, why not?"

We went back and forth for a few rounds, repeating quite a few of the questions and dares that I had done with them during our first game. But then it was Jeremy's turn, and he picked truth. Caleigh was asking the questions, and she asked him when was the last time that he masturbated. And Jeremy's face dropped, and he started to squirm in his seat. He reluctantly admitted that it was earlier that afternoon. He didn't say this to them, but I knew that it must have been right after we watched the movie. Because that was the only time he was alone for long enough.

I couldn't tell for sure, but I was pretty sure Kyle and Caleigh had put two and two together and had figured that out as well. I can't blame the guy; I was super horny after watching that movie myself.

We exchanged a few more innocent dares and truths back and forth, but then they had to go, so we said goodbye and went to log off. But just before we did, they asked if we'd accept a homework dare. I glanced at Jeremy, and he nodded, so we told them that sure, we'd accept their dare. They said it was pretty simple again. And that the dare was to watch Truth or Dare 2. But they warned us it's a little spicier and not something we'd want to watch if our parents were home.

We said our goodbyes and logged off.

"Whoa, how bad do you think Part 2 is going to be?"

"I'm not sure," I said, "but I can't wait to find out."

"Me neither. Ok, I'm off to bed. Goodnight Ange."

"Night Jer."

* * * * *

We actually had to wait a few days until our parents were out of the house. But Saturday morning our parents left for a wedding and wouldn't be back until Sunday. So we knew it was the perfect time to watch it.

Later that afternoon, we took our respective places on the couch and loaded the movie. As soon as the opening credits rolled, there were a lot more viewer discretion is advised warnings.

"Sorry Ange, you're going to have to look away during any sex scenes; I wouldn't want to corrupt you or anything."

I reached over, pretending to grab some popcorn, but quickly averted my reach and punched him in the arm. I don't think I hurt him very much. Lol.

The movie started, and the first scene, the first game of truth or dare, almost instantly involved nudity and sexual themes. The movie is about a group of friends that play truth or dare games together (let's just say there's not a lot more to the plot than that).

There are 8 people in this group: a brother, a sister, the brother's girlfriend, two couples, and another single woman. So three men and five women. All of them in their early twenties.

As the movie progresses, the dares get more and more sexual. There are boobs flying everywhere, people are kissing, hands are groping--it's getting pretty intense. And the situation is not lost on either myself or my brother. It's getting to the point where I'm practically watching a porn movie with my brother in our living room. But I wasn't complaining.

During the final scene of the movie, it's the brothers turn, and he picks dare; they announce this is going to be the last dare of the game. The person creating the dare? His girlfriend. They had a very healthy relationship in the movie, but at one point earlier in the movie, he had gotten her good with an interesting dare, and she was out for payback.

They did a pretty good job of building the suspense at this part in the movie. It was time for the dare. "I dare you to remove your shirt, and for your sister to remove her shirt, and the two of you have to hug, topless, for one minute." The entire room fell silent, and the rest of the group spent the next several seconds picking their jaws off the floor.

"That's crazy. Whoa!!!. OMG," the whole group was losing their mind. In the movie, brother and sister sat in complete silence. And so did me and Jeremy. I looked over at him at one point, and his eyes were just wide open, staring at the screen.

The sister said fuck it and pulled her shirt over her head, revealing a super cute set of tits. To be honest, we had seen it a few times throughout the movie, and I'm not afraid to admit I had enjoyed the view the entire time.

Her brother slowly pulled his shirt over his head, and the group of friends broke out into huge applause. No one could believe they would actually go through with this.

The girlfriend pulled out her phone, opened the clock app, and got the timer ready to go. She asked, "You guys ready."

The brother and sister had locked eyes with each other and didn't break eye contact, but both nodded, signaling their willingness to get started and complete this dare.

"3...2...1... Let the dare begin," called out the girlfriend, and the brother and sister embraced.

The group, which only moments ago had been quite loud and boisterous, fell completely silent. Jaws dropped, eyes wide open, they watched as the sisters pointy little breasts pressed gently into her own brothers bare chest. The both wrapped their arms around each other and settled in for the longest 60 seconds I've ever witnessed on film.

I gotta be honest, but much to my surprise, I felt a twinge of excitement running through my loins as I watched the onscreen siblings embrace in their hug. It was just a simple hug, but it was so sensual and sweet. I saw movement out of the corner of my eye coming from the other side of the couch, and I glanced over just as my own brother had finished adjusting himself while never once taking his eyes off the screen.

"Time," the girlfriend proclaimed, and the group burst out into a standing ovation.

"That was the most insane thing I've ever seen."

"Ya, but soooo sexy too."

"I can't believe they did that."

No one could believe what they had just witnessed. Lol, the movie was a little over dramatic, but I guess it's not every day you witness a sister mash her tits into her brother's chest.

The credits rolled, and me and Jeremy just sat in silence while all of the credits finished. One thing I forgot to mention earlier was that Caleigh and Kyle had also dared us to join them for another game of truth or dare immediately after we watched the movie.

I looked over at Jeremy and said, "Well, I guess we better go see if Caleigh and Kyle are around. But I need a drink first. You want one?"

"Fuck yes!!! I mean, yes, please. I gotta run and use the bathroom; back in a minute."

I got up and mixed us a couple of very stiff drinks.

A few minutes later, Jeremy was back, and we logged in together. Last time we played with them, we were both on our own phones in our own room. This time I had grabbed my laptop, and we were sitting next to each other on the couch.

* * * * *

"I can't believe you dared us to watch that movie," I declared as soon as Caleigh's cute face popped up on screen.

"OMG, what did you think?"

"That was pretty wild," I said.

"Ya, that's one of our favourites," said Kyle.

"Wait until you see Part 3!!" Caleigh said with a huge grin on her face.

Jeremy hadn't said a word yet. He just sat there next to me.

"Ok, you two ready to take things up a notch?" Caleigh asked.

I said, "Of course, that's why we're here.".

Jeremy took a big swig of his drink.

The tone of the game had definitely flipped, and there were sexual undertones to all the dares and truths. But for the most part, things had remained pretty innocent.

We learned quite a bit about each other during these rounds; it turns out all four of us are bisexual, something I didn't know about Jeremy, and I'm pretty sure he didn't know that about me. Caleigh and Kyle had admitted they both wanted to invite other people into their relationship (sexually speaking). Jeremy and I both admitted that it had been a little while since either of us were in a committed relationship. Although Jeremy has been more sexually active than I have lately. We learned a little bit about everyone's kinks. All of us enjoy watching porn from time to time, although Kyle and Jeremy were more into it than us ladies. And as the game wore on and as we all drank a little more, we all began to loosen up and have a great time together.

It was my turn to pick, and I chose truth this time. It was Kyle's turn to ask, and he asked, "Do you own a dildo or vibrator?"

"I do," I said with pride.

We're all adults, and I had no problem admitting that I owned numerous sex toys.

"Cool!" blurted Kyle, but then instantly he started to blush as he realized what he had just admitted.

It was now time for the dares to ramp up a little bit. Jeremy dared Caleigh to show us her tits, and, man-o-man, they didn't disappoint. Caleigh had c-cup tits with just the right amount of sag to them. But the sexiest part about them were her ghost nipples. She had beautiful tanned skin but the lightest coloured areola and nipples.

Both Jeremy and Kyle were dare to show us the imprint of their penis' by pressing the fabric of their shorts against their crotch. I can't blame either of them for being rock hard. I can't believe I looked at my brother's penis, but he was packing a fairly substantial instrument in those shorts.

Caleigh had to reach into her underwear, insert a finger into herself, and then suck her own juices off of her finger. That was one of the hottest things I had ever seen.

It was my turn to accept a dare, and Kyle did not disappoint. He dared me to suck on my own nipple for 30 seconds. We had not discussed whether or not I had the ability to do this, but it was pretty obvious by my huge tits that this wouldn't be too much of a problem. But the realization quickly sank in that Jeremy was going to be seeing my tits in the flesh for the first time. Fuck it. A dares a dare. I had never tried this before but was able to reach my nipple pretty easily. It felt amazing and is something I will certainly be adding to my masturbation repertoire going forward.

I looked over at one point with my nipple completely inside my mouth and made eye contact with Jeremy while doing that. It was one of the most insane moments of my life.

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