Pressing Matters with Sister Pt. 02 - Fall Break

I grabbed my dick and started stroking it. I hadn't masturbated in this way in so long, the sensation was almost foreign. The oddly unfamiliar feeling only increased my arousal at that moment.

With everything going on, it didn't take long for me to reach my peak. I grunted as the pleasure raced up my shaft, exploding across my body. My first burst of cum arced onto Lindsay's back. I expected my skinny sister to be grossed out, but instead she giggled as the warm liquid splattered her.

"Oh, that's so awesome," she said, staring wide eyed at my dick. My next shot hit her again and she writhed.

"Give me some of that," Lucy said. She arched upwards, presenting her massive tits as my target.

I was barely able to move at that point, wrapped in my rapture, but I did my best to aim my dick and managed to splat my sister's boobs (to be fair, they were hard to miss). I kept cumming between my sisters, till finally, I fell back into the couch.

Lindsay was the next to go, shuddering and shaking in that cute way of hers. She let out several sharp, high-pitched gasps as she gave in to the pleasure. Already her orgasm was so familiar.

Finally, Lucy went off with a deep grunt. Her head tipped forward. Blue eyes rolled back in her head. She let out a long "Ahhhhhhhh" as the ecstasy slowly leaked out of her.

The three of us lay in the living room for a while, staring at the walls. Finally, Lindsay popped up off the floor.

"That was awesome," she said, "But I think you got some in my hair."

"Sorry," I said, still in post-orgasm stupor. "You have a lot. Of hair."

Lindsay pulled her long, brown locks around her and stared at them, picking at all the sticky spots. She'd stayed topless and there was something incredibly sexy about how the strands covered her tiny tits.

"I think you got some on my boobs, too," Lucy said, grinning at me lasciviously. She lifted up one of her massive mounds and eyed it, mirroring her sister.

"To be fair, you have a lot of tits," Lindsay said.

Lucy laughed and conceded that that was true. I stayed on the couch, looking dumbfounded at what I had wrought and wondering what else could possibly happen next. In some ways, we'd already gone farther than what Lucy and I had done in the summer. And that had ended so badly. I couldn't bear the thought of it happening again.

But I couldn't entertain the idea of stopping any of this either.

*

That night at dinner, my parents announced our plans for Thanksgiving the following week, which were unsurprisingly low key. Mom was going to get a couple of roast chickens from Costco, and we were going to stay around the house, all six of us.

"Your Aunt Becky invited us to her place but that's a six-hour drive," Dad said, "And the gas money is out of our budget."

We all agreed that it wasn't worth the extra expense.

"Actually," Lucy said, "My friend Kara is going to be back from school, and I was hoping she could join us. Her parents are away at some ski resort thing."

"Which one is Kara?" Dad asked, "I don't think I remember her."

"Daaad," Lucy whined, "You know Kara. We've been friends for, like, ever."

"If you say so," Dad said, with a dismissive shrug.

I, on the other hand, remembered Kara quite well. She was my older sister's best friend, and I had a bit of a crush on her. We'd had an 'encounter' at Lindsay's birthday party and Lucy had gotten upset, drunk, and horny all in succession. I was both incredibly excited and extremely nervous at the thought of seeing that girl again.

"Kara's more than welcome to join us," Mom said, "But make sure she knows things are going to be modest."

"Oh, she'll just be happy to have the company," Lucy said. She gave me a strange look that I couldn't read. What was my older sister up to, exactly?

After dinner, we cleaned up and then the family watched TV in the living room. Thinking about what had happened earlier that day on that couch made me paranoid about what might have been left behind, but no one seemed to notice. Instead, we all sat there, acting normal, as if half the family wasn't having incestuous circle jerks behind the other half's back.

Our show ended. One by one, my family went off to bed, leaving me and Lindsay.

"That was fun this afternoon," Lindsay said, casually, after Jan went upstairs. "I loved seeing you shoot off like that."

I looked at my sister in shock. Was she out of her mind randomly talking about that stuff in the living room? Anyone could have heard her, yet she said it like she was talking about a sandwich I'd made, rather than about how I'd spread my mayo all over her back.

"What?" Lindsay said, reacting to my expression.

"We're not supposed to talk about it."

"Why not?"

"What do you mean why..." I paused, so flustered I couldn't find words. "Because it's not appropriate."

"So, it's OK to do it, but not to talk about it?" Lindsay asked.

"Exactly," I said. Alright, so maybe I was twisted up in my own argument there.

"That doesn't make any sense," Lindsay said. She folded her arms around her little chest, pouty.

I shrugged. Someone had to be the keeper of propriety here. My little sister's enthusiasm was fun, yes, but she was going to get us all in trouble.

"Look -- what we're doing," I said, "We shouldn't be doing it, right?"

"Why not?" Lindsay asked that question again. Like it was the height of philosophical dialectic.

"We're. I mean it's. Fuck." Language was leaving me so fast, I could only grasp at the words as they raced past me. It left me with a frantic, meaningless ramble.

"It feels good," Lindsay said, "And it's fun. So, I don't see a problem. I mean, you're not stopping, right?"

I had to concede all of that.

"And if it's OK to do then it must be OK to talk about, too," Lindsay said, "Right?"

I struggled to refute her logic, even though it didn't actually make any sense.

"I've been learning a lot about my chakras," Lindsay said, "They're these elements of energy inside of us that we can harness in order to be more whole, happier beings. When we inhibit the flow of that energy, that's where anger and unhappiness come from."

"Right," I said, making my disdain clear. My sister was into all kinds of hippy dippy stuff like that, most of which I assumed came from vaping too much pot with her friends. Of course, the exercise part of it had an amazing impact on her body, so I wasn't complaining too much.

"Chakras feed into all kinds of things -- my desires, my emotions, my ability control myself and my life. I feel very in tune with myself when we press together. Completely immersed in the flow of us. It's very enlightening."

Enlightening. Self-induced orgasms with her siblings. Got it.

"I'm a human being with physical wants," Lindsay said, "I'm not going to make myself feel bad about something that feels so good. And you shouldn't either, OK?"

I looked at my pretty little sister. Her bright, green eyes so soft and caring. The cute smile playing on her thin lips. She eyed me in a way that made me feel cared for, safe, in a crazed world. Our lives had been so upside down the last few years and yet Lindsay had found a way to find order in that chaos.

Besides, if I won this argument, exactly what was going to be my prize? Would we stop pressing? I wasn't that stupid.

So, I agreed with my younger sister. "Yes," I said, "OK."

"Good," Lindsay said. She clapped her hands, happily. "Because I want to see your thing shoot again. That was awesome."

After Lindsay took her little tits out of her tank top, I was more than happy to oblige. This time, I showered her chest with my seed. She bounced up and down like it was the world's greatest magic trick.

"Holy fuck that's so hot," she said, rubbing my spend into her tiny pink nipples. I assumed she'd want to rub one out herself, but instead my little sister just skipped off to bed. I stared after her, trying to figure out how I'd gotten tangled up, unable to find my way back to reality.

*

Despite our new dedication to open discussion, the next week passed without much excitement. We all hunkered down for exams before the break, I think, and it took away most of our energy. The three of us pressed together a few times, but it was a quick thing with none of the 'performance' of our earlier sessions.

Then break started and we got caught up in prepping for Thanksgiving. Despite my mom's insistence that everything was going to be as cheap and easy as possible, we still ended up spending all our time on cooking and cleaning. The fact that we were having a guest, I think, made Mom feel way more self-conscious about how we were living.

The house we were renting was old, almost certainly haunted, and it collected dust everywhere -- like someone was using a sifter of sand in every room when we weren't looking. It made every cleaning project an extra chore, more like exhuming a body than keeping our own living quarters clean.

But we did our best to stay cheerful as we went through it. Holidays were particularly stressful with everything that had happened, so we all worked extra hard to keep each other engaged.

Finally, Thanksgiving Day arrived. The table was set. The dog show was onscreen. We were all ready to settle in for a day of overindulging in food, alcohol, and television.

Kara arrived shortly before 2pm, even her knock on the door was bubbly and cheerful. Lucy hurried over to answer it, and immediately embraced her petite friend in a hug so big, it threatened to swallow the girl.

My sister finally released Kara, and the brunette immediately caught my eye. Reflexively, I stared down at my shoes. Kara was super cute. She was petite with dark brown hair and a tight little body. Her build was kind of like my younger sister, Lindsay, although she was skinny, rather than lithe or toned.

The last time we'd met up, at Lindsay's birthday party, Kara had given me her number. We'd texted a few times, but mostly it went nowhere. Now I was regretting the lost opportunity. With her deep brown eyes and wicked smirk, Kara was very much in my crush category. All the sibling masturbation sessions couldn't quench that fire.

Kara walked over and gave me a light kiss on the cheek. I looked immediately at Lucy, waiting for the jealousy monster to leap out from her lips, but instead my older sister just grinned at me. Like she knew a really good secret.

Soon after, we sat down to the meal. There was enough food for all, but I would never have described it as a sumptuous feast. Weird how even our indulgences were a reminder of all the things we could no longer indulge in.

Everything started OK. My Dad asked Kara how school was going, and she did a good job keeping things light. My sisters chimed in, and we were having a pretty good time. But then one innocuous question stopped everything dead.

"So where are your parents during the holiday?" Mom asked.

"Oh, they're off at the ski resort," Kara said.

"Ski resort," my dad said. It was not a question.

"Yes, it was this whole thing," Kara said, "Dad said that money was tight, so he reserved at this place that isn't as nice as usual and Mom freaked out."

"Yes," Dad said, "Important to be financially responsible."

The room went dead silent. I think Kara realized what she'd been saying, but it was too late. The cloud of our family's failures hung over us, thick and murky. I felt it, heavy, in my chest.

We'd been those people, once. Never as rich as Kara, of course, but doing well enough to have a nice home, new cars, and a good vacation. Dad didn't set out to lose his job, we all knew that, but it happened anyway. Suddenly we were scraping by.

Dad had found another job for about a quarter of the pay. Mom went back to work and Jan cut grad school short to start earning money. The only reason Lucy and I weren't working was because Dad insisted that school was more important and wouldn't allow it. Watching him gather up those last shreds of his pride was almost worse than seeing it obliterated in the first place.

So, hearing Kara talk about having to accept the 'lesser' chalet while we stared at two sad, skinny chickens at a busted up table in a sad, old house -- I guess it hurt a little. With conversation stifled and the meal mostly gone, we turned to the one thing we still had plenty of: alcohol.

We'd ended up with a half dozen bottles of wine and we proceeded to methodically murder them all. It didn't make dinner less awkward, but it helped us remember less of it in the morning.

After dinner, the inevitable began to take its effect. My Dad found his way to the football game and Jan joined him. Mom ended up napping in a corner. That left Lindsay, Lucy, Kara and I to sloppily clean up.

At one point, while I collected the dishes and Kara and Lindsay were washing in the other room, Lucy sidled up next to me, nudging my side.

"Kara's been eyeing you all night," she said.

"That's nice," I said, absently.

"You should make a move," Lucy said, "I think she'd go for it."

"Last time, that did not turn out too well," I said, looking at my sister meaningfully.

"It's fine," Lucy said, "I won't get mad."

"Are you sure?"

"Yes," Lucy said, "Kara's a nice girl and she could do a lot worse. Besides, I feel like one of us should score on Thanksgiving, since it looks like the Cowboys can't do it."

"Thanks," I said, meaning it.

Our lives had been so cursed, dating hadn't felt like an option. And while I enjoyed my little meetings with my sisters, they also put me in an uncomfortable spot for other relationships. What had happened when I flirted with Kara last time, I was not going through that again. So having the green light from my sister left my engines revving hard.

Once we were done cleaning up, I made my way over to Kara. I was about to suggest she come see my room for some lame reason (it was the best excuse I could think of), but Lindsay beat me to the punch.

"We should do something," my little sister said, "The rest of the family is busy, so let's hang out."

"That could be fun, I guess," I said, mentally cursing my cock-blocking baby sis.

"We could play a boardgame," Kara said, "I think I saw some in one of the bedrooms before."

"Oh hell no," Lucy said, "That's only going to lead to trouble."

"What if we did our thing?" Lindsay suggested.

Both Lucy and I swung our heads toward our sister so fast, I'm surprised our necks didn't snap in unison. What did she just say?!

"I don't think that's a good idea, hon," Lucy said, taking the side of reason for once.

"I bet Kara would really like it," Lindsay said.

Oh my God. I was going to grab my sister's chakra and wrap it around her neck. I knew we'd all probably overconsumed, but as far as I could tell, Lindsay was suggesting this soberly. This was beyond a disaster; it was a twenty-car pileup with a nuclear-powered van in the middle of the wreck. Everything was on fire, irradiated, and melting down to the atoms.

"Is this some game you guys play?" Kara asked.

"Yeah, ha ha, a game," I said. I took Kara's arm and started to steer her away. "Come on, I want to show you this cool thing I've got up in my bedroom."

"Yes, Dylan's bedroom is a great idea," Lindsay said. "OW!"

I looked over in surprise and saw that Lucy had pinched our little sister's arm, hard. I can't say I blamed her.

"What was that for?" Lindsay asked, rubbing her arm.

"Never mind," Lucy said. She turned and smiled at Kara. "Little sisters, right? So annoying."

"I have two older brothers," Kara said with a shrug, "They're weird, but mostly harmless."

"Are they both skiing with your parents?" I asked, desperate to change the subject. You know it was a bad sign if I was willing to bring that up again. It truly felt like the safer of the two conversations.

"Kevin is," Kara said, "But Kenny's over at his fiancee's house for the holiday."

"Oh cool," I said. Most. Awkward. Small talk. Ever.

"So, what's this thing you want to do, Lindsay?" Kara asked, "I'm intrigued."

"Oh, it's awesome," Lindsay said, "You'll love it."

"I think our little sister has had a little too much to drink," I said to Kara. Then I turned to my sister. "Right, Lindsay?"

"I'm fine," Lindsay said, calmly. "Let's go up to the bedroom like Dylan suggested."

Notice how I was now implicated in all this? Yeah, that was just lovely.

*

Lindsay cajoled us all into following her upstairs. She marched straight into my bedroom, grabbed one of my pillows, and followed it to the floor.

"Um, what are you...?" Kara stared from outside the door frame. We all did.

"It's simple, see," Lindsay said, "You rub yourself up against the pillow and it starts to feel really good.

"Oh wow," Kara said.

"Oh my," Lucy said.

"Oh no," I said.

"And the three of you, um, do this together?" Kara asked.

My stomach rushed to the floor, broke through the foundation of the house, and headed right for the Earth's core. I wished to God I could follow it to my burning oblivion.

"Yup!" Lindsay said, casual as anything. "It's great on its own, but together makes it way more fun."

Kara was now staring straight at Lucy and me. I couldn't read the expression on her face. I desperately didn't want to. Whatever was behind those eyes, I didn't want to consider it. Just run and hide. Then die. Preferably quickly.

"She's not wrong," Lucy said, shrugging slightly, "It is fun. Right Dylan?"

Fuck me. "Uh, yeah," I said, "I mean, I guess. If you're into that kinda thing."

"And you are into it?" Kara asked.

Thus, there I was, trapped between not looking like a masturbating, incest pervert in front of a girl I liked or taking my sisters' side. And, in this case, I didn't truly have a choice now did I?

"Yup," I replied, "I guess I am."

Kara pursed her lips while tilting her head. "OK," she said, "Well, I suppose I should give it a try."

And then, like it was no big deal, she skipped into my bedroom, grabbed another pillow, and dropped down next to Lindsay on my hardwood floor. My little sister gave Kara a grin and patted her arm, like a friendly welcome.

Based on their descriptions, you might think that Kara and Lindsay looked alike. After all, both were short, petite brunettes with small breasts and perky butts. The most obvious difference was the hair, Lindsay's was long and straight whereas Kara's was wavier and cut to her shoulders. Further, Lindsay, thanks to her endless exercise obsession, was limber, while Kara was merely petite. And while Lindsay had more of a girl's face, Kara's appearance was softer and womanly. They were both super attractive, for sure, but the differences between the two were stark as they both lay down on the floor.

Lucy glanced at me, then looked at the two women in my bedroom. Even my sister, who usually seemed so in control of these things, was flummoxed by how all this had come together.

"I guess I'll get a pillow from my room," Lucy said.

"Sometimes he strokes it for us, instead," Lindsay told Kara, weirdly matter-of-fact. "It's really hot."

"I'll bet," Kara said. She had a very different, yet still completely unreadable, expression on her face.

"I love it when he shoots," Lindsay said, "That's the best part."

"We should probably stick to pressing for now," Lucy said, returning with a pillow under one arm. This was not getting any more normal. The only explanation was that I'd cracked my skull at some point during dinner and this fever dream represented the death throes of my logical mind.

Lucy joined the other girls on the floor. She gave me a head nod. Well, seeing as I was already underwater, I supposed I might as well drown. Not needing a pillow for my own process, I simply lay down on the floor, facing my two sisters and my crush. The three of them looked so hot, splayed out in front of me.