It had been a few days since our little video reveal to Caleigh and Kyle with Jeremy's dick lodged in my throat. Followed by my little brother's entire hand making its way inside of me. And immediately following our little bit of fun, and even after our mutual shower, things seemed pretty good between my brother and me.
But the next day and for the past few days, something just felt off. I think Jeremy was avoiding me. We've both been super busy with our own lives the last couple of days, but there's a tension in the air that I just can't put my finger on. I need to talk to him about this. Make sure everything is okay.
"Hey Jer." I sent him a text.
"Hey Ange, what's up?"
"Not a lot, just thought I'd check in and see how you were doing?"
"Fine, I guess."
"You guess? That doesn't sound very fine. What's up?"
"Are we...how do I put this?" The three little dots appeared, then disappeared, then came back. He was writing something but seemed hesitant to hit send.
"It's ok, Jeremy; whatever you need to say, just say it." I sent him, hoping to reassure him that it was ok to talk to me about whatever he needed to talk about.
"Um...I guess, is this wrong? Should we be doing what we're doing? What if someone found out?"
"I don't want anyone to find out about this either. Except Caleigh and Kyle, of course. But there's lots of things in life that I don't want the whole world to know about. That doesn't mean they are wrong. Have you been having fun playing these games lately?" I asked him. Trying to reassure him it was all ok.
"Of course. It's been some of the most fun times I've ever had. I just don't want to do anything that would end up getting you in trouble. Or hurting you in anyway. I really care about you. Especially after everything we've been through together."
"I feel the same way. Look, we can stop if you want. No harm, no foul. I'll still always be your sister. We just go back to being regular siblings. Would that help?"
There was a long pause before he finally responded.
"I'm not sure, Ange. I really don't want to stop. But I don't want to fuck up our lives. So...I don't know. Maybe. Ugh. I need to think about this a little more. I'm going away this weekend on some university visits. Maybe getting away for a few days will let me clear my head."
"Ok, if that's what you think you need."
"Wait, Ange."
"Ya."
"I just want you to know that I meant what I said the other day. I do really love you. And that's what this is really all about. I just want to make sure that I don't end up hurting you in any way."
"I love you too, Jeremy. It's ok. Have fun this weekend, and we'll talk more when you get back."
Was Jeremy right? Should we stop all of this? Was this getting out of hand? I didn't want it to stop. In fact, I wanted it to keep going. These last few weeks had been some of the best weeks of my life. But if he needed space, I'd give it to him. That didn't mean I had to stop playing.
I logged back into the Truth or Dare app and tried to see if Caleigh and Kyle were online. Shoot. No luck today. Maybe I'll try to find some new people to play with.
I spent the next few hours popping in and out of games. I played with a few people, and it was ok. But it just wasn't the same. So I logged off for the day and went about trying to distract myself with other things around the house.
* * * * *
Saturday afternoon rolled around, and I had the house to myself. Jeremy and my parents had gone into the city for the weekend, checking out schools.
I decided a little masturbation couldn't hurt. So I grabbed my favourite vibrator, stripped off all my clothes, and climbed into bed. I know we were taking a little break from things, but the whole time I was masturbating, I couldn't get Jeremy's face or his dick out of my mind. And everything was feeling great, but I just couldn't push myself over the edge. Getting a little bit frustrated, I thought back to our last time together when Jeremy fisted me to orgasm, and I thought it was worth giving that a try.
So I grabbed some lube from my bedside table and started fingering myself with two, then three, then four fingers, and that was honestly going a lot easier than the last time I tried this myself, so I tucked my thumb in and pushed. It wasn't so much that I couldn't fit my hand inside; it's that it was a bit of an awkward angle. I tried a few different positions, and eventually I was able to contort my body in such a way that it gave me pretty easy access, and my fist slipped right in. It caught me a little off guard because I wasn't really expecting it to work. But fuck did it feel good. I felt stretched to the max again. I began working my hand in and out slowly at first and eventually started picking up the pace. Just as I was feeling my orgasm coming along, I heard a chirp from my phone and totally lost all my momentum.
Frustrated, I got up to see who it was. And it was Caleigh. She had sent me an email.
"Hey Slut! Where have you guys been?"
Fuck it. Just because Jeremy didn't want to play with us at the moment doesn't mean I couldn't. So I grabbed my computer, logged in, and started a private game with Caleigh and Kyle.
I explained everything that was going on, and they totally understood. They asked if I'd be up to playing a game with them still, and I said, of course. That's why I logged on.
"I do have a little confession to make." I said.
"What's that?" Caleigh responded.
"I was just in the middle of a pretty intense masturbation session when I heard your email arrive in my inbox. I actually had just managed to fit my whole hand inside myself and was about to cum when you rudely interrupted me."
"Oh fuck, that's hot." Caleigh replied. "Ok, well, no point in getting too creative here. I dare you to resume what you were doing and give us a little show. I'd love to see that."
Jeremy's loss. He's the one missing out. I'm going to enjoy my time with my friends. I focused my camera on my bed and reapplied lube to the front and back of my hand. And then slowly started working my fist back inside myself. I was able to do it in a much simpler position this time, which worked out great for my audience. Caleigh was especially vocal in her cheering on of me.
It didn't take too long of working my hand back and forth before I threw my head back and came very, very hard. It was quite an intense feeling to feel my pussy squeezing my hand like that. Wow, did I need that? That felt amazing.
We played a few more rounds from there. I dared Caleigh to give Kyle a blowjob while also fingering his ass with two fingers. He seemed to really enjoy that. Kyle dared me to suck on my nipples again. Apparently he's a big fan of that. I dared Kyle to fuck Caleigh and cum inside her pussy, then he had to lick out as much cum as he could and share it with Caleigh.
It was pretty fun; who am I kidding, it was amazing. But I do have to admit it wasn't quite as exciting as when Jeremy was there playing with us. I missed my brother.
We were just about to say our goodbyes and log off when Caleigh said she had a homework dare for me. I accepted. The dare was to convince Jeremy to come play one final game with them. They had a secret they wanted to tell us. But they'd only tell us together. They also said they'd agree to let him veto any challenge he didn't want to happen. I said I couldn't guarantee he'd agree but that I promised to try. That was good enough for them, and we said our goodbyes and logged off.
* * * * *
Jeremy and my parents returned Sunday afternoon, and everything seemed pretty normal. No tension or anything. Jeremy had a great time and was pretty sure he had narrowed down his choice to a single school with a quality backup option. I gave him a big hug and told him I was super happy for him. My mom sort of gave me an odd look at the hug but literally shrugged her shoulders and walked away without any discussion.
I was trying to come up with the best time to talk to him about my dare. Do I wait and give him the chance to talk to me about things, or beat him to the punch and just ask him right away? I decided the latter option was the best way to go.