Pressing Matters with Sister Pt. 02 - Fall Break

Welcome to part TWO of the Pressing Matters series!

Last time, Dylan and his older sister Lucy started masturbating together. Things got out of control and there were consequences. Have the siblings learned their lesson? (clearly not)

And yes, I'm well aware that this is the second story I've written around Thanksgiving. I guess there's something about turkey that I find something truly erotic.

All participants are over the age of 18.

"Hey, come here."

My sister, Lucy, and I were lying on the floor of her bedroom. Lucy had a pillow under her, slightly folded so it was pressing at her crotch. I was on the bare ground, grinding my groin into the hardwood floor like doing a cobra pose in yoga. My body trembled with effort. Both of us must have looked so silly, our faces red with effort. Eyes glazed over and oddly empty.

Our youngest sister, Lindsay, stood at the opening of Lucy's room, staring at us with a mix of shock and curiosity. Our eighteen-year-old sister was thin, with brown hair hanging down to her waist. She was wearing her standard outfit of a tank top and yoga pants. Her arms crossed under her barely-there breasts.

"Come here," Lucy said to our sister. "Try this. It feels really good."

My older sister and I had spent our entire summer doing this. We called it pressing. Lucy -- blonde and buxom, two years my elder -- had started it. But I was a no less willing participant. We would hang out in the house like normal, then sneak off to her bedroom to hump the floor. For three straight months, we did it at least once a day and sometimes way more than that.

It was just dry humping. Even when we started doing it on top of each other, it felt mostly chaste. But one fateful afternoon, I took things too far.

Lucy had been lying on the floor of her bedroom. Her body so curvy and inviting. It had been an accident, at first, when my bare dick slipped into my older sister. But we kept fucking very much on purpose.

That probably would have been our new routine. Both of us agreed that it felt amazing. Except for one problem. We lost control (even more than we already had, believe it or not) and I ejaculated inside her.

Lucy wasn't on birth control. Our family's recent financial downturn had meant giving up a lot of necessities and apparently the pill was one of them. We spent an anxious month, and no small amount of our skimpy savings, on pregnancy tests. Thankfully, inexplicably, my boys managed to miss the target. Lucy's period showed up right on schedule.

But the reality of what we'd done -- I'd inseminated my own sister's unprotected pussy -- was the best form of birth control we'd ever encountered. Just like that, the sexy times stopped. No pressing. No nothing.

Other things got in the way, as well. We both were fully into our college classes by then. We made new friends at school. Life continued on. But none of that would have mattered if we'd really wanted to go back to our old ways. And we didn't.

September turned to October, the leaves went from green to orange/red, but my sister and I stayed away from each other. What had happened, what we'd almost created, was enough to scare us straight. I assumed forever.

Then, suddenly, as November arrived and brought the icy winds of impending winter with it, our previous thaw began to melt away. One day, I caught Lucy pressing in her bedroom, door wide open, and decided to join her. A few hours later, Lucy found me in my own room, and we did it again. Without talking about it, without ever making a conscious choice, we were right back to our old routine.

The rest of the family didn't notice any of our trials and tribulations. Our older sister, Jan, was working full time and then some. So were my mom and dad. Our younger sister, Lindsay -- who'd turned eighteen a week before our 'incestuous almost-impregnation incident' -- was so swept up in her senior year of high school, I doubt she'd have noticed if Lucy and I were cooking meth in her bedroom.

Except, she did notice. Because Lucy decided to call Lindsay's attention right to us.

Like I said, we were lying on the floor of Lucy's bedroom, doing our usual afternoon press after classes and before we had to make dinner. Lucy had left her door open, but I didn't think anything of it until our skinny, brunette sister walked past, then froze in our doorway.

I started to say something, but the embarrassment of it stuffed the words back in my throat. Fortunately, Lucy was conscious enough to save the day.

"Hey, come here," Lucy said.

Seriously, we were so lucky that my older sister was able to think on her feet and ensure that Lindsay didn't... Wait. WHAT?! The reality didn't so much dawn on me as it steamrolled me right over. Did Lucy just invite our younger sister to join us?!

Lindsay stood in the doorway, staring like she was seeing two horny ghosts. She had to know what we were doing. My little sister was innocent sometimes, but she wasn't stupid.

"Seriously, it feels really good," Lucy said. The way our older sister was so casual about this was maybe the strangest part of all.

"I don't know..." Lindsay said.

"Tell her, Dylan," Lucy said.

"It's nice," I said, unable to get much more vocabulary out than that. Remember, I was mid-hump when Lindsay had interrupted us. And while my mind had gotten an ice bath of epic proportions, the message had yet to make it to the rest of my body.

My younger sister was certainly cute. She was petite, skinny, with an elfin face and an adorable smile. Lindsay was one of those artsy, granola types -- all about health and wellness. She'd been vegan since she was twelve and did barre at least three times a week. And so even though she wasn't curvy at all, she was nicely defined. Especially her pert, bubble butt.

"Get in here," Lucy said. Her demand was ridiculous, but it did the trick. Lindsay scampered into Lucy's bedroom like she was the one who'd been caught doing something naughty. "Grab a pillow off my bed."

Lindsay did as she was told. She found an empty space on the floor, her head meeting ours in the middle, and placed the pillow in the spot where her groin would rub against it. I was too entranced by what was going on to go back to my own ministrations. I noticed Lucy seemed equally enthralled.

Our younger sister wiggled her backside as she settled onto the cushion.

"Yes, that's it," Lucy said as Lindsay's perky butt settled down. "Like that."

"Uh huh," Lindsay said.

She looked so serious, it was almost funny. My younger sister wriggled around a bit more, then froze.

"Oh!" Lindsay squeaked in surprise.

"See?" Lucy said.

"Uhn." Lindsay grunted. "Uh huh."

Her sister clearly settled, Lucy got back to her own grinding. For a moment, I lay there and stared as both my sisters humped the pillows on the floor. It was hard to pick who was more exciting to watch.

On the one hand, Lucy's curvy body screamed sex. Her massive tits and wide hips. But then Lindsay's lithe little body was no less alluring. And this was the first time I'd ever seen her like this. She had these little trembles, like small seizures, as she slid against the pillow on the floor.

Lucy got my attention and, wordlessly, made it clear that I needed to stop staring. I realized she was right. If Lindsay caught me looking this stopped being something we were sharing and became more of a performance. This magical, masturbation bubble we'd created would *pop* like a balloon on a hot day.

I quickly focused on my own pleasure. It didn't take long for me to build back to where I was before. I did my best, however, to hold myself back from the big finish. I wanted the girls to go first.

Lucy was the first to peak. I heard her now-familiar low, throaty groan as she took herself over the top. Eyes rolled back in her head.

"That's... it..." the words squeezed out of her like she was a strange, buxom accordion

A moment later, Lindsay let out a cute little squeak.

"Oh!" she cried out, her whole body shaking like she'd been shocked. Tongue lolled out of her mouth. Finally, she collapsed, lifeless, to the floor. She let out a long, soft, "Ahhhhhhhh."

After that, I figured it was safe for me to spend and so I did. The pleasure arced through me in short, sharp spurts as hot jets of semen spattered in my shorts. I rolled onto my back and stared up at Lucy's ceiling. Her floor so strangely comfortable.

"Nice right?" Lucy said.

"Yeah..." Lindsay said, dreamily.

*

I assumed, stupidly, that that would be the end of things. I don't know why I thought the three of us would do it that one time and Lindsay would be done with it. I don't know how I could have so easily mistaken an entrance for an exit.

Still, you can see there's a certain logic to my thinking. After all, if you were asked to list the most likely occurrences in my life, regular masturbation sessions with two of my sisters would have been pretty low, right? Probably buried somewhere between 'get my own unicorn' and 'find a million bucks abandoned on the sidewalk.' And yet, that's exactly what happened, with the kind of casual inevitability that usually accompanies events like 'tuna sandwich for lunch.'

That very evening there was a knock on my bedroom door. I was lying in bed, watching something dumb on my phone, and starting to get good and sleepy. So, I was surprised by the sound, to say the least. I was wearing a pair of pajama pants and nothing else, so I pulled on a t-shirt before I answered.

My parents were both passed out and Jan, my oldest sister, was out with friends. Lucy, the most likely candidate to be bothering me at that hour, was never so overt as to knock on my door. She'd find some other way to get my attention if she needed it. There was only one other person it could be: my little sister Lindsay. But that didn't make any sense either, we didn't have that kind of relationship. Yet when I opened the door, there she was -- wearing a frilly, sleeveless sleep shirt and staring at me in the near-darkness.

If her appearance was a shock, you can only imagine my reaction to what Lindsay did next. She went across the hall and knocked on Lucy's door. My curvy, blonde sister opened it, looking at both of us like we were the world's weirdest Jehovah's witnesses.

"I want to do it again," Lindsay said, acting exactly like the young, petulant sibling she was.

In an evening of unexpected events, this was the one I was probably the least prepared for. I was no stranger to a late-night press with Lucy. We'd been doing that for months. But neither of us had ever spoken about it aloud. That was straight up crazy. Who came out and invited someone, verbally, to a mutual masturbation session?

I looked over at my older sister. Lucy was wearing a simple t-shirt and shorts. Her eyebrows were raised in confusion. Her mouth, however, slipped into a smirk. Without another word, the buxom blonde girl motioned for the both of us to join her in her bedroom.

Just like that, as if this was an everyday occurrence, Lucy closed her door behind us, tossed her younger sister a spare pillow, and flopped onto the floor.

Not long after, the three of us cascaded into our personally supplied orgasms. This time, I was the first to go. I think the whole scenario had me worked up more than usual. As I went over the top, the heat of my spend shooting down my bare legs, I felt at least one pair of eyes on me. I assumed it was my younger sister, Lindsay, but it might have been my older sister, Lucy. Or maybe both.

I honestly don't know. In the moment, I didn't care. It just added another level to the already high peak I was reaching.

"That's so hot." I heard my baby sister whisper through the haze of my post-orgasm ecstasy.

"I know, right?" Lucy said.

A moment later, the room filled with the low groans and sharp gasps of my sisters cumming, themselves. I was too fogged out to notice who did what. Not that it made the experience any less alluring.

An arm bumped against my body as Lindsay settled in next to me. Lucy's leg kicked against mine. All three of us lay there on the floor, warm and post-cum cozy.

The next time I blinked, I saw it was 3am. I peeled myself off the wood floor and limped back to my bedroom. My leg hairs sticky with dried cum.

*

The next day, Lucy volunteered to drive the three of us to school.

"Dylan and I are both going to County and Lindsay's high school is kinda on the way," she explained to my parents as we packed up our things that morning. "Besides, I want to help you guys out more if I can."

"That's very sweet of you," Mom said.

"We really appreciate it," Dad said.

Jan stood in the kitchen, arms crossed primly, eyeing the three of us like she was sure we were all spies.

We piled into my older sister's sad Honda Civic -- Lindsay in the front with Lucy, me in the backseat -- and drove off. We hadn't even left the driveway before Lindsay started into it.

"Last night was a lot of fun," Lindsay said.

I felt the air leave the car. My stomach twisted. Like I said, Lucy and I had been pressing regularly all summer. So masturbating with my siblings, didn't feel that different. But we definitely didn't ever talk about it. That was the act of an insane person.

"I'm glad," Lucy said, calmly. Her clipped response was a clear 'be quiet,' but Lindsay didn't hear it.

"I think we should do it again," Lindsay said, "Maybe this afternoon when we all get back from school."

"OK, honey," Lucy said, patting our younger sister on her skinny leg.

After we dropped Lindsay off, I climbed into the front seat with Lucy, and we drove off toward County.

"What was all that about?" I asked, pulling on my seatbelt.

"What?" Lucy said, slightly distracted.

"You know with the," I began, fumbling for the words. Did I really need to explain this? "The afternoon. And stuff."

"Let her be enthusiastic," Lucy said, smiling at me placatingly. "It's fun."

I shrugged, but inside I was still sullen. It's not that I was upset that Lindsay was involved in our thing. Like I said, it was kind of nice to have a new participant. But the way she was so open about it? That made it all weird and I didn't like it.

I comforted myself that it was just conversation. As long as we quietly went about pressing, I supposed I could live with a little chatter.

*

"I want to see your thing," Lindsay said. She beamed at me, broadly. Like a kid asking for a lollipop at the supermarket.

We were all in the living room after school. Unlike usual, when Lindsay would spend all afternoon lounging around at some friend's house, she'd hurried straight home. I was done with my classes for the day, and I'd camped out on the couch while Lucy brought our sister home from school

I'd been watching TV, coming down from the day, when our youngest sister rushed right into the house, threw down her things, then tossed a pillow onto the floor. She didn't even bother to say hello.

"Well?" she asked, staring up at me, impatiently.

I turned to Lucy, standing in the doorway. We shared a look somewhere between impressed, apprehensive, and excited. I don't know if even Lucy had anticipated that involving our baby sister would bring us to this point. Our illicit activities had already felt risky without Lindsay's incredible enthusiasm.

Still, we flopped to the floor. The three of us crowded so close together we had to shift so our elbows wouldn't collide as we pressed. We'd barely even begun when Lindsay took things up yet another notch.

"Fuck that feels good," Lindsay said.

OK, so a little dirty talk during wasn't all that new. Lucy and I, when we were in the full throes of our self-pleasure summer, had started doing the same thing. We hadn't gotten back to it since our autumn restart, but it made sense that we would try again at some point.

But Lindsay wasn't idly talking to turn herself on.

"Fuck, I want to see it," she said.

"You are seeing it," I said. I did my best gesture at how the three of us were getting off in plain sight.

"Not this," Lindsay said. She looked pointedly at my crotch. "That. I want to see your thing. While we do it. That would be so hot."

I turned to my older sister. Lucy shrugged at me. I couldn't read her expression at all. Lindsay's look, however, I understood implicitly.

"Take it out, Dylan," my baby sister said, twisting her hair in her fingers. "I bet Lucy wants to see it, too."

I assumed Lucy would be the levelheaded one, although I can't imagine why. I mean, all the evidence I had was that my older sister was equally as crazed as my younger. But, for some reason, I continued to assume that Lucy was going to put the brakes on things. Instead, she did exactly what I should have anticipated by now.

"Yeah, Dylan, show us your cock," Lucy said, "Stroke it for us."

Well, I wasn't one to let down my sisters. I got off the floor and sat on the couch. I was about to slip off my pants, but I stopped. Through the haze of my sibling-induced arousal, I managed to have a moment of inspiration.

"You have to show me something, too," I said.

Both girls paused. They turned to look at each other, eyes searching. As I've said, my two siblings looked very different. Lucy was full and curvy. Her face was on the round side with full lips and a slightly upturned nose. Lindsay, on the other hand, was all angles. She had a sharp chin and a thin mouth -- almost the opposite of her older sister, really. And yet, in that moment where they glanced at each other, my sisters looked so much alike, it was uncanny. Their blood relation abundantly clear.

"Tops," Lucy said, and Lindsay nodded her head.

Both girls reached for their shirts and bras then tossed them aside. They were still on their stomachs with me sitting above them, so I didn't get a full glimpse. It didn't matter. The grandeur of the view -- it was like eyeing the Andes and the Himalayas all at once.

I'd seen Lucy's full, glorious boobs before, but that didn't make them any less amazing. They were so large, yet perfectly formed. There was something inherently unreal about them, as if such wonders could only exist in fiction.

Meanwhile, I was getting my first glimpse at Lindsay's little mounds, and they were no less incredible for being so much smaller than her sister's. Lindsay's tiny tits were incredibly perky, almost sharp with light pink nipples.

My sisters made the exact same 'ahem.' Both girls had been looking at me expectantly for a while, but can you blame me for not noticing? They shared a knowing, goofy grin.

I took the hint and pulled down my jeans and boxers. My dick popped out, eager. Whatever softness I might have needed to press on the floor was lost in the excitement of everything else. I was as hard as I'd ever been, like I'd installed my own personal coatrack.

If I'd stared a bit too long at my sisters' chests, they more than made up for it by the way they ogled my dick, entranced. Lindsay's mouth hung open, her eyes wide. Lucy's own blue orbs sparkled; her mouth twisted into a hungry grin.

"Ahem," I said, mimicking my sisters.

"Just give us a minute," Lucy said.

"Yeah, don't rush us," Lindsay said.

"Fine," I said. I felt so on display, my dick somehow both flagged and flag-poled harder at the same time.

Finally, my sisters settled back in and started to rub themselves on the floor. They kept their heads tilted upwards, though, staring at my cock.

"Stroke it, Dylan," Lucy said, "Get off with us."

"Yeah, I want to see it shoot," Lindsay said.

I did as I was told, as if I needed the encouragement. Watching both my topless sisters hump the floor, their bare tits trembling, was more than enough to make me want to work myself. The way they seemed to be enamored of my erection only increased the urge. It was like being told to have a heartbeat -- it was going to happen no matter what they said.