Pressing Matters with Sister Pt. 02 - Fall Break

I remained in denial, though, because I was sure we were all going to lay there. I mean, this was well and good, but we weren't going to all masturbate on the floor. That was crazy.

But, of course, that's exactly what we did.

Lindsay started first, pressing her little butt down and gradually grinding herself back and forth on the pillow. Lucy followed, arching her back and pressing herself downward. Kara looked to her left and right, like taking notes. Then the pretty brunette girl, a woman I'd lusted after for years, did something sort of in-between what the two siblings were doing.

"Oh..." Kara said, "That's interesting."

"I know right?" Lindsay said, "Like you can kind of see how it would work but once you do it, the whole thing seems way more obvious."

"And pleasurable," Lucy said.

"Yep," Kara said, "Definitely." Her dark brown eyes glassed over, and I could see she was already gone.

Watching this should have had me hard, but the nerves of everything kept me soft. Ironically, that was the perfect place for me to be in order to get my press on. I squeezed my glutes, letting the pressure build. Kept my muscles tight for as long as I could, then relaxed. Once I recovered, I started again.

On the one hand, I knew it was a bad idea to look at the girls in the room with me. On the other, I couldn't imagine doing this without watching Kara and my sisters get off. It was too good an opportunity to turn down.

"Ah. Sssssso good," Kara said. Her voice choked and strained. Fuck, that girl was gorgeous. I'd fantasized about her for almost as long as she'd been friends with Lucy. Seeing her there, edging to her orgasm, was nothing short of incredible.

"Yuh-yeah," Lindsay agreed. My cute little sister looked so adorable getting herself off. That illicit mix of innocent and alluring only made it all the more amazing.

"Getting... close," Lucy said. I'd seen this with my sexy older sister so often, yet it never failed to be fantastic.

There was no chance I would last long. Fortunately, my companions still managed to beat me to the punch. They fell in order, like dominoes. Lucy was the first to go, eyes rolling back in her head with a long, low groan. Lindsay toppled next, letting out her usual little high-pitched squeak. Finally, Kara shuddered, froze and released a stuttering, choking gasp.

"Ah-ah-AH!" She fell forward, burying her head in her arms.

I'd just seen my crush girl orgasm for the first time. It didn't matter that I was in a room, masturbating, with my sisters. I didn't care that Kara's cum had been self-supplied. It was glorious. I couldn't have gotten a greater wish from a genie.

I spurted before I even realized I was there. It hit me so fast, so hard, I moaned out loud. The heat of my seed spurting into my underwear. When I looked up, my vision out of focus, I saw Kara staring right at me. Our eyes locked. Finally, the pleasure overcame me, and I let my head drop.

We all lay there like the dead for a moment. It felt like someone should say something. It seemed like silence was the best policy.

Kara got up first, breaking the spell. "Well, that was, um, interesting," she said. She brushed her hands on her jeans.

"I'll see you out," Lucy said, weakly. She stood up on trembling legs.

"No need," Kara said. She quickly headed out of the room and down the steps.

My sisters and I shared a knowing look. Incredibly, we'd all managed to fuck things up even worse than they already were.

*

I spent the night running disaster scenarios through my head. In the best case, Kara simply kept quiet and never spoke to any of us again. In the worst... there were too many 'worsts' for me to track.

When I got up the next morning, I found Lucy sitting at the table. My blonde sister looked like she'd had about as much sleep as me.

"This is bad, right?" I asked.

"Really bad," Lucy said.

"Fucking Lindsay."

"We could have stopped her," Lucy said, "This is on all of us."

"Kara's your friend," I said, "Maybe you should talk to her?"

"Oh, I'm pretty sure she and I will be talking plenty soon enough," Lucy said. The tone of her voice made it clear that it was not going to be a jolly conversation.

Lindsay came down a few moments later. She had on a tank top and yoga pants. Her eyes were sunken, but she acted surprisingly upbeat as she made herself a morning cup of herbal tea.

"I'm sorry about last night, guys," she said. "I really thought Kara would enjoy it." You'd have thought she was talking about watching a horror movie or trying an exotic cuisine. Not rubbing off together in front of a friend.

"Lindsay this has to stop," Lucy said, "It was fun, but we can't do this. We're already risking too much."

"But..." I could tell Lindsay was about to do the whole chakra speech, but common sense finally came in and stopped her.

"I know. I'm the one that started it," Lucy said, "But it was a mistake. This isn't going to end well for any of us."

Lindsay hung her head. She slowly nodded. I could tell she was disappointed -- hell, so was I -- but there was no arguing this. We'd done something dumb, and the only recourse was, once again, to stop putting ourselves in the position.

Lucy's phone beeped and she looked down at it.

"It's Kara," she said, sullenly. "She wants to come over and talk."

The Friday after Thanksgiving is usually an off day, but Dad and Jan were both able to get extra pay by going into the office. Mom decided to brave the crowds at the mall to see if she could take advantage of the sales. That left myself, Lucy, and Lindsay alone in the house, once again. At least that meant Kara couldn't get us into too much trouble. Or maybe I was delusional again.

I tried to think about what I would do in her situation. Freak out? For sure. Call the cops? Jeez, I hoped not. I assumed that Kara would want to back away quietly. So why was she coming back to the house? I could only think of two possibilities. She was going to scream bloody murder at us for dragging her into it. Or she was going to threaten to tell someone -- parents, police, local press -- and blackmail us. Both possibilities felt equally possible and completely disastrous.

"Maybe it'll be OK," Lucy said, the two of us sitting nervously on the couch. She had on a pink, fuzzy sweater and dark blue jeans. We shared a dubious look. "I mean, she got off, too. Right?"

There was a loud knock on the door. Lucy stood up to answer it like walking to the lethal injection. A slow, reluctant stride. Lindsay gave me a nervous look. I shrugged back at her.

"Hey!" Lucy said as she opened the door. Her happiness so forced it hurt me.

"Hi," Kara said. I noticed she wouldn't meet my sister's eyes. Instead, she tucked her hair behind her ear and walked into the house.

All of us stared at Kara as she made her way to the couch and sat down. Like looking at a tiger who'd randomly rambled into our living room. Lucy and Lindsay joined us, and now all four of us sat there. The silence was deafening.

"Do you want anything to drink?" Lucy asked.

"No, I'm still feeling last night," Kara said.

OK, last night came up and she didn't say anything about it. Maybe this was a good sign. Perhaps she was going to pretend that nothing happened. Oh, who was I kidding? This was a nightmare, and it was only getting darker from here.

"So," Kara said, letting the word hang in the air like an axe above our necks. "Do you want to maybe do the thing? You know from last night?"

And somehow the room got silent-er. I didn't think that was possible. Like muting a show that was already quiet. If we could have heard a pin drop before, now it felt like we could hear the molecules of the pin vibrating.

Did Kara just...? I couldn't even think the words.

"Seriously?" Lindsay asked. She couldn't hide the thrum of excitement from her voice. "That would be awesome."

Kara nodded. Her face slightly flushed. I realized that she wasn't anxious with anger or upset with disgust. The pretty brunette was straight up horny. I think all of us were too relieved to question why.

"I'll get us girls some pillows," Lucy said.

"OK to do it here?" Lindsay asked.

"Sure thing," Kara said. Then she looked right at me. "But I want to see Dylan shoot this time."

*

Our first go went so quickly, it was over before I could take stock of it. The women all writhed on the floor, then stared up at me, rapturous, as I inseminated the Kleenex. It was fast and fun, but I was barely recovered from the scare of that morning so I couldn't fully enjoy it.

"Your brother's got a nice one," Kara said, as if I wasn't in the room to hear.

"I know, right?" Lindsay said, "I love watching him cum."

"Feels even better when he spurts it on you," Lucy said.

"Well, fuck, I have to try that," Kara said.

We took a break for lunch (we're not depraved), then headed up to my bedroom. This time, I managed to convince the girls that they needed to be topless if they wanted to see my spend and they happily obliged.

Kara's tits were larger than Lindsay's and quite nice, with light brown, puffy nipples. They had a slight upward curve to them as well. Should I admit that, despite the wonder of seeing my crush's bare chest, I preferred my sister's titties? Welp, I guess it's too late now.

So now there were three hot, topless girls getting themselves off on my floor while I stroked myself next to them.

"Do you think about him, your brother, while you do this?" Kara asked Lucy, both of them red-faced and sweating.

"...Sometimes," Lucy said.

"Fuck that's hot," Kara said.

"What about you?" Lucy asked Kara. "Do you think about it?"

"You mean Dylan?" Kara asked, "Or my own brothers?"

"Both."

"...Sometimes."

Kara's admission seemed to set Lindsay off because she came a moment later. Her usual high-pitched squeal was more of a scream. Lucy and Kara both shuddered after her. Then all three women looked up at me, expectantly.

They didn't have long to wait. A moment later, the pleasure raced up my dick and splattered the three of them. I got them on their backs again, mostly. But I was pleased to see a few drops dripping down Kara's chest.

All three of us lay back, panting. For some reason, I felt the awkwardness slide over us again. What were we doing? How was this actually happening? I knew that reality would break in at any moment, the spell would crack, and we'd all be left with nothing but disappointment and shame.

"You're right, Lus," Kara said, "It is better when he cums on you."

The third time(!?) was even better(?!?!?!?!). Rather than join the girls in pressing, Kara decided to sit on the other side of me and get herself off with her fingers. We made a little masturbation sandwich that way, me stroking my cock, my sisters lying on the ground, and Kara on the other side. Her legs spread wide, hiding nothing.

She already had her top off and for this round, Kara stripped down naked. I was surprised to see that her pussy was covered in dark, curly hair -- completely untrimmed. There was something arousing and naughty about that.

I guess the situation, the exposure, got to the pretty brunette because she orgasmed almost immediately.

"That was. A good one," she gasped out. Then she kept going.

I sat back and lazily stroked my cock while the three girls got themselves off. Despite already exploding twice that day, I could tell I was on a hair trigger. Seeing Kara's bare pussy put me at another level.

"God, that cock looks good," Kara said, staring right at me. I couldn't stop the smile that ran across my face. For a moment, I thought that maybe it meant she was going to do more. I was wrong. But only sort of.

"I know right?" Lindsay said, "I love watching him while I get off."

"You should stroke it for him," Kara said, "Feel it."

"You mean," Lindsay said between gasps. "Get him off?"

"Don't you want to?" Kara asked, "Have your brother's hot, hard cock in your hands? Feel it thicken and tremor when it shoots. Know it was you that made that happen?"

Lindsay stopped rubbing and looked down at the ground, shyly. I thought for sure that Kara had taken things too far.

My little sister leapt to her feet and practically tackled me. Her little tits swung as she rumbled over. We both groaned as she grabbed hold of my dick.

Lindsay's strokes were far too fast and clumsy but it hardly mattered. Her enthusiasm more than made up for it. I saw she was also working herself with her free hand. For a moment, I thought about reaching over but I was too in her control to move.

"That's a good little sister," Kara said, "Making your brother cum."

As you can imagine, I didn't make it much further after that. Lindsay giggled as my cock swelled in her palm. She made sure my first burst hit her chest, then aimed the next down at Lucy. As soon as my seed spattered her back, my older sister was swallowed by an orgasm of her own.

I lost track of things for a moment, the ecstasy overwhelming my senses. I was vaguely aware of the groans of pleasure as the girls also got off. Happy moans and blissful giggles. I waited for consciousness to drift back, but instead I just felt warm and sleepy. Finally sated, the four of us passed out on the floor.

We woke up before anyone came home, thank God. I can only imagine the reaction if someone saw us. Mostly naked, covered in boy and girl cum, splayed out practically on top of each other. We looked like we'd had an orgy and, honestly, we kind of had.

All of us slowly dressed, then limped down to the kitchen. Whatever was left of our awkwardness had been wiped away by three, hardcore, stroke sessions.

"You want to come by again tomorrow?" Lindsay asked as Kara gathered her things.

"I'm heading back to school, sadly," Kara said, "I'll be back for Christmas, though."

"Cool," Lucy said. Her casual acknowledgement that we would be continuing through the winter holidays was almost as arousing as what we'd all done together. A promise of our future promiscuity

The best friends hugged goodbye. then Lindsay and Kara shared an awkward little wave.

"This was fun," Kara said, "I might have to start up something similar back at school."

"Not at home?" Lindsay asked, teasing.

"Yeah, maybe that too." She was so quiet, I couldn't be sure she actually said it.

Then Kara shut the door behind her. As it clicked closed, I realized that she'd never said goodbye to me. For a moment, I felt sad. Kara was my crush girl and after everything that had happened...

I looked over at my two sisters. They were smiling at me, desirous. Maybe I was better off without Kara, after all.

*

The next day was Saturday. Jan was out doing Jan-things on a weekend trip with friends, but my parents were both home all day, making it hard for us to get away with anything. It was probably for the best; I think we all needed a day to recover after Thanksgiving's debauchery.

But there was a further finality to everything. Kara, our newest and most surprising co-conspirator, was already gone. Our own break was almost over. And while I was convinced that Lucy, Kara and I would continue on, I knew that things were going to change. So, I went into Sunday pretty confident that any sibling sexy-time was going to be on pause for a while.

Repeat it with me now: I was wrong.

Sunday morning, I should have seen the signs. First thing, before the rest of the family woke up, Lindsay caught me making breakfast. She touched my chest, then let her hand slink down lower. Her fingers dandled near my groin.

Despite everything we'd already done, I nearly jumped out of my skin. Yes, in the heat of everything on Friday, my little sister had stroked me off. But in the cold morning light, right in the middle of the kitchen, it still felt weird. And dangerous.

"We need to do stuff again," she said, grinning at me broadly, "Soon."

I knew better than to argue it with her at this point. So instead of protesting, I tried to play it off with a joke.

"You want to give our chakras a little recharge?" I asked.

Lindsay's hand slid lower. "Actually, I was hoping we could align them," she whispered in my ear. She grabbed my cock through my pants. I was hard as hell, of course I was, and she gave me a steady squeeze.

I didn't need a yogi to tell me what my little sister was implying. Hell, Yogi Bear could have solved that riddle. The hornier part of my mind (aka the majority) leapt for joy. But the smaller, smarter part, held back. I'd been there once before, with Lucy, and that had gone about as badly as possible.

I jumped away, separating myself from my little sister.

"I don't think that's a good idea," I said.

"You always say that," Lindsay said, pouting, "But then I always prove you wrong."

"No, it's not like that," I said, "Lucy and I, we..." I froze. Was I revealing a confidence to my sister? Something I wasn't supposed to share?

"What happened with you two?" Lindsay asked, "It seems like you both are into things, even more than me. But you keep yourselves controlled."

"We made a mistake," I said, "I don't think I should say anything more."

"It'll be different," Lindsay said, "I don't get jealous. And I don't care about physical stuff. It's just our bodies. It's natural."

"Are you on birth control?" I asked. I know, I said the think-y part out loud. But at that point, I knew I needed to act the older brother.

Lindsay tilted her head at me, confused. "You know I'm not," she said, "We had to stop all the prescriptions. But I trust you. I know we'll be safe."

I gave her a dubious look.

"Seriously? What happened?" Lindsay asked. Her usually sunny disposure had gone grey.

"Nothing," I said, "Ask Lucy."

"I'm asking you," Lindsay said. She pressed against me, and not in the fun way.

"Oh! I hope that's fresh coffee I smell!" Mom called down from the stairs. A moment later, she flounced into the kitchen.

"Pot's ready now," I said.

"I knew we had you kids for a reason," Mom said. She reached for a mug and filled it.

When I looked over to find Lindsay again, I saw she'd already left the room.

*

I spent the rest of the morning out doing chores. OK, fine, I spent it hiding from my sister. Still, it was the thought that counted.

When I came back home, it seemed that the house had emptied. Thinking I was safe, I plopped down on the couch and turned on the TV. Not a second later, my other masturbating sister was sitting right next to me.

Lucy gave me a quick, pained grimace as she plopped down on the couch. She was in her now-usual-for-the season sweater and jeans -- a black top this time that looked good with her golden hair.

"Lindsay talked to me," she said.

"Oh," I said.

"She seems to think something happened between you and me," Lucy said.

"We're fine," I said. I gave her an almost believable smile. "More than fine."

"Maybe I shouldn't have included her," Lucy said, "At the time, it seemed like a good idea."

"A lot of bad ideas seem smart when we're in the middle of that kind of stuff," I said.

"Yes," Lucy said, she chewed at her lower lip. "I never blamed you. For what happened."

"You could have," I said, "Probably should have."

"No, that's not right," Lucy said, "What we did, we did it together. I'm not sad that it happened, either. I mean, not the end part. That was..."

"A mistake," I interrupted.

"Hell yeah," Lucy said, "Big-o mistake-o."

"Humung-o."

"But the rest of it," Lucy said, "The only thing I regret is that we did something that made it stop. Lindsay's crazy but she's right about one thing: there's nothing wrong with what we're doing. It's fine. It's fun."

"Unless we get caught," I said.

"We won't," Lucy said, "We'll be careful."

I think I wanted to believe her so much, I let her convince me. It was becoming a bad habit on my part.