Pressing Matters with Sister

Once again, I sat down to write a short one-shot and ended up going waaaaaayyyyyy overboard. Hope you enjoy my (over)exertion.

As always, all participants are over the age of 18.

"Dylan, come here."

My older sister, Lucy, was lying on the floor of her bedroom. She was on her stomach, wearing only a t-shirt and panties. She had a pillow under her groin, folded at the corner. She held herself in a backwards arch, like doing a cobra pose in yoga. Her body trembled with effort. Her cute, round face was cherry red. Her light blue eyes glazed over and oddly empty.

I'd been lost in my own world, walking down the hall, when Lucy called out to me. It was a hot day, summer was just getting started, and I was already suffering under the sad reality that our new house didn't have air conditioning. My minimal outfit of a t-shirt and mesh shorts felt like a full, fur coat.

"You should. Try this," Lucy gasped, "Feels really good." She took a deep breath and collapsed flat on the floor. "Fuck." The word slipped out of her. Her long, golden blonde hair pooled around her head.

I stared at Lucy as she lost herself for a moment. My older sister's skimpy outfit revealed way more of her curvy body and tan skin than I was used to seeing. Her breasts looked particularly large in her baby blue v-neck. Her full butt was similarly flattered by her yellow, bikini-cut panties.

I couldn't help but compare myself to my sister. My hair was closer to brown than blonde. If Lucy was all circles, then I was straight lines. We had the same blue eyes, and our faces were similar, sort of, but that was about it.

Lucy came back to consciousness. "Seriously, Dylan, come here," she said, an edge of annoyance in her voice.

Tentatively, I stepped inside her doorframe.

"What's up?" I asked, playing dumb.

As a 19-year-old boy, just two years younger than Lucy, I knew what masturbation looked like. But I'd never seen anyone do it that way with a pillow. And I certainly wasn't prepared for my sister to openly share it.

Lucy and I had always been close. Unlike our friends (and our other siblings) who seemed to be suffocated by their close relationships -- fighting each other for air -- Lucy and I both basked in our shared spaces. We were playmates as kids and confidants as teens. I told my sister nearly everything and had an easy expectation that she would do the same.

But we weren't, you know. Like this.

It was awkward when we watched a movie, and a sex scene came on. I felt uncomfortable folding Lucy's underwear when I did the laundry. I noticed my sister had a nice body because she was super curvy and stuff. But I didn't, like, sneak on her in the shower or ogle at her bathing suit when we went down the shore.

We were, you know, normal siblings. Until that random afternoon when my sister called me into her bedroom while she was grinding her pussy against a pillow.

"Come on, try this with me," Lucy said. She wiggled her butt purposefully, clearly starting her process all over again.

"You mean, like, lying on the ground?" I asked.

"Not exactly," Lucy said. She looked up at me, her face pink and sweaty with exertion. "You put a pillow down. And you lie on top of it. Then you kind of press down. You know? Feels awesome."

I can't say why I listened. It should have been weird -- OK, it was weird -- but for whatever reason I treated it more like my older sister was inviting me to try a new game or watch a movie. Gingerly, I stepped into her bedroom. Like me, Lucy was a bit of a geek. She had a flatscreen TV with a couple consoles attached. Her tan bedroom walls had posters from Breath of the Wild and Animal Crossing. Her room was a peaceful, welcoming place.

But in the moment, it felt almost foreboding. Like the air itself was all charged up. As soon as I stepped inside, I was hit with the scent of my sister's honey-sweet perfume mixed with something else; instinctively familiar.

"Grab the one from my bed," Lucy said, breathily.

I took the pillow -- a sad, floppy, lime green thing whose filling had fled long ago -- and dropped it on the ground. I fluffed the pillow as best I could, then lay down on top of it. I adjusted myself till I had my genitals in what seemed like the right place.

"There you go," Lucy said, "Now just..." Instead of saying it, she did it. Arched herself again. Her wide hips swiveled slightly back and forth on the pillow. Again, I became very aware of my sister's body. Her broad shoulders and long arms. Large breasts and bubble butt. Pretty face and light, sparkling sapphire eyes.

I tried to mirror my sister. I pressed down into the pillow and wiggled a little. And, amazingly -- despite the fact that we were working with very different equipment -- I could kind of see what Lucy was getting at. Like catching a glimpse of a mirage from the far side of the desert.

There were a few problems that kept me from getting closer, however. One, the pillow made things too soft. For my sister, the cushion gave her something to rub against. For me though, I got the sense that I needed something firmer. Honestly, the bare floor would probably have been fine.

But, ironically, the other problem was that I was too hard. Everything around me -- my sister, what she was doing, what she invited me to do -- had led to the inevitable reaction. At any other time, an erection was the perfect way to start getting myself off. But not like this. Some instinctual part of me knew that if my cock was softer, it would be easier to press against the ground and, theoretically, might feel nice.

I looked over at my sister. Unintentionally, we'd ended up facing each other. Quite close. I could see every detail of Lucy's face, screwed up with effort. She was clearly building toward another release. She clenched, held, then flopped in a strained, desperate rhythm. Over and over, like an odd kind of exercise.

I stayed in place, just lightly pressing down. There was the distant sensation that maybe something could be there, but I knew I wouldn't be able to reach it in the moment. Instead, I sort of teased myself while I watched my sister take herself down the path to pleasure.

"Nothing?" Lucy asked, suddenly aware that I was staring at her.

"Kinda?" I said, "I get the feeling it might work if some things were different. But not right now."

"Oh, OK," Lucy said, clearly disappointed. "That's too bad. I'm glad you tried it though."

"Me too," I said.

Carefully, I got off the floor. I tossed Lucy's pillow back on her bed. My older sister was still pressing herself when I left.

I wandered away, feeling shell shocked. Unable to remember where I'd been headed in the first place.

*

About an hour later, I was in my bedroom -- sweating my balls off while playing Elden Ring -- when the thought popped into my head.

I could be doing it right now.

It was a random idea, borne of nothing, as if my subconsciousness had been chewing on this for a while and finally spit it out.

I put the controller to the side. Looked down at the grey carpet. My bedroom door was shut. The distraction of my repeated virtual deaths meant my dick was soft -- exactly where I needed it to be. I slid off my chair and dropped to the ground.

Like my sister had showed me before, I pressed down with my crotch and arched my back. Like lightning, there it was. This was a very different experience than I was used to. It was more work than stroking myself off, but it also felt fantastic in a slightly different way. Because I was lying on my stomach, in some ways it felt more like fucking, because I could imagine someone under me, feeling the same building pleasure.

Just when I felt myself begin to tire, I reached my apex. My orgasm splattered down my legs in warm, wet spurts. The pleasure overwhelmed me. The effort to reach that place had been so much. The orgasm was a wondrous final reward.

I lay on the floor for a while, smelling my carpet. Muscles aching like I'd done an hours' worth of exercise. I drifted in and out of a strange, altered consciousness. Only dimly aware of the world around me.

*

The family all came home around the same time for dinner. Mom had grabbed Chinese on the way back from work and we all loaded up our plates. We had a tiny, circular dining room table that my dad had found at a yard sale down the street. It was big enough for four, but not six, so Lucy and I set out stack tables in the nearby living room and ate on the couch.

For such a large family -- Mom, Dad, my three sisters and myself -- dinner was upsettingly silent. I remembered how meals used to be, all of us carousing around the big table, talking excitedly about what had happened that day. Here, though, the clatter of utensils and plates overwhelmed whatever urge we might have had to say anything to each other. And what was there to talk about, really?

I waited till everyone seemed truly lost in their own worlds, then I elbowed Lucy. She turned and glared at me.

"What was that for?" she asked.

"I did it," I said, under my breath, "I made it work. In my bedroom."

"Oh, awesome," Lucy said, her face shifting from slightly irritated to fully excited. Her eyes lit up like bright blue fire. "How was it?"

I looked down at the ground, shyly. I guess some things still felt strange to admit to my sister.

"Nice," Lucy said, and gave my shoulder a playful shove.

After dinner, our siblings left to go hang out with their respective friends, leaving Lucy and me to watch TV with our parents. It's not that we didn't have our own social groups because we did. But most of our friends had gone away to college, while we were now at County, and so we had fewer social options.

I suppose we could have gone out, the two of us, but it was awkward to wander around our old hometown. The thought of running into people, of having to explain what had happened -- I don't think either of us was anticipating that interaction. So, instead, we stayed on the couch and watched TV with my parents.

It didn't take long, however, for Mom and Dad to shuffle off to sleep, and so we found ourselves sitting together on the beat-up couch. Almost close enough to be cuddling.

"You want to do it?" Lucy asked.

"Huh?" I asked. I looked over at my sister. She was wearing a long, light pink, sleep shirt that went down to her knees -- hiding her ample curves. She gave me a winking smile, like she was telling a dirty joke.

"Do you want to?" Lucy asked again. Suddenly, I realized what she meant.

"Here? Now?"

"Upstairs," Lucy said. She didn't wait for my response, just stood up and glided out of the living room. I mean, was I truly going to sit and watch TV by myself at that point?

Back in Lucy's bedroom, I found her already lying splayed on the floor, pillow strategically placed under her. She'd lifted her sleep shirt up to her waist, exposing a pair of robins' egg blue, bikini-cut panties.

Lucy grunted hello, then ground into the ground. "You need a pillow?" she asked, throatily.

"Nah," I said. I lay down on the floor. I could feel myself stiffening already, and I knew I needed to take the opportunity before the act became impossible.

Lucy's hardwood floors felt even better than my carpet. We were facing each other again. Hearing my sister's gulping breaths, feeling her body tremble nearby, all of it conspired to take my experience from a solid 7 to a tremendous 10. Moments later, I was shooting hot seed into my shorts.

"You go?" Lucy asked. She looked about to hit the precipice, herself. Her cheeks were pinker than her shirt.

"Yeah."

"Ahhhhhhh," Lucy was overtaken by her own orgasm. Her eyes rolled back, and she collapsed. "Fuck that's nice."

Lucy picked up her head and met my eyes. Her look was dreamy, distant. Yet there was something focused beneath the surface. Like she was making a decision.

We shared a goofy grin.

"That's it for you?" Lucy asked.

"Pretty much," I said. I had no doubt I could squeeze another orgasm out of myself. But the rubbing took a lot out of me. Something about it was so much more taxing than the usual stroking off.

"Well, OK," Lucy said, "I'll see you in the morning."

I knew, right then, that she wasn't making the usual, trite statement. It was an appointment.

A promise.

*

Sometimes it takes a while to settle into a new habit. Retraining your body, your mind, to incorporate a different routine. That was not the case for Lucy and me. We were barely past our first day of this and already our fresh tradition felt expected. As if we'd been doing it our entire lives and would continue to do so forever more.

Lucy called it pressing and so that's how I came to think of our activity. It wasn't always at the same time or even every day, but we managed to have regular regroups. One morning we might wake up, press together, and get ready for the day. Or after lunch, we'd have an afternoon press in between doing chores or playing games or whatever. And if we missed both of those (or were having a particularly 'active' day) we'd go for a press after dinner, right before bed.

Outside of our little meetups, everything else was normal. We weren't flirty with each other. We didn't even talk about what we were doing. We always wore clothes when we did it -- Lucy with some sort of shirt and panties, me in my t-shirt and shorts. We met up, pressed, and went back to our lives. Like all of this was happening in some separate, bubble universe.

The way everything became casual, however, was also nearly our downfall. Three times, with three separate people, we were almost caught.

The first was my fault. It happened a little over a week after we'd started our escapades. The family had finished dinner and was watching TV. It was one of those rare evenings when all six of us were home, and Lucy and I found ourselves sitting on the floor, in front of the couch.

Lucy turned to me, mid-episode, and cocked her eyebrow. She subtly jutted her chin. That was all I needed to know. I gave her a single nod.

It was on.

A moment later, Lucy said she was feeling tired and went to her bedroom. I waited what felt like a good amount of time (but was probably only two minutes) and followed her upstairs.

I found my sister already lying on her pillow. She gave me a big, goofy grin as I lay down next to her. The process of this had made me start to chub up, but I'd learned to (literally) push through such things. We humped the ground together, the sounds of boring TV news playing in the distance.

There was this strange intimacy to our act, stolen in little moments. For the most part, I stayed within myself, engaged in my own fantasies. But then I would hear Lucy make a little gasp as she hit the right spot. Or I would grunt with the exertion of the act. Sometimes we'd accidentally bump each other -- arms or legs, never anything more. It was strangely reassuring, an encouragement of the illicit actions we were sharing.

"What are you guys doing?"

I froze. I slowly turned my head to the source of the sound. Our younger sister, Lindsay, was standing in the doorway. In my haste, I'd forgotten to close Lucy's door. Damned.

Lindsay was 17, mousy and thin, with light brown hair (the same color as mine) that hung almost to her waist. She was wearing her usual workout outfit -- a tanktop and yoga pants. She eyed us, confused, like someone searching for an obvious word but unable to find it in the moment.

"Nothing," Lucy said, like this was a perfectly satisfying answer. She didn't even get off the pillow. Just spun around and stared up at our younger sister. "Go away."

Lindsay did not do that. Instead, she stayed at the door, narrowing her eyes like she was processing everything.

"It's fine, Lindsay," I said, the panic rising in my throat. "We're hanging out."

"We're planning your birthday gift," Lucy said. This was a particularly bad lie, since we were doing nothing that looked like planning. And Lindsay's 18th birthday was still a good two months away.

But while our youngest sister was super sweet, she wasn't very sharp. She wasn't a dope, just far too trusting. The kind of girl who couldn't understand that people might lie to her for their own benefit.

"Oh!" she said, brightly, "OK." And quickly scampered away.

I wasn't going to argue with our good luck. I got off the floor, gently closed Lucy's door, and returned to what we were doing.

The second time we almost got caught, though, was on Lucy (somewhat). It was a Saturday afternoon, a week or so later, and she found me watching TV in the living room. She was wearing a white t-shirt with a pink Tom Nook on it, as well as a pair of green sweat-shorts. Her breasts and bottom seemed liable to break out of both at any minute.

Lucy gave me our signal and I got off the couch. But instead of leading me back to her bedroom, Lucy shook her head.

"Here," she said. That one word was shocking, for all that it implied. I glanced around the room. Right out in the open? We were sure to be seen.

"No one's home," Lucy said, "They're all out doing errands or whatever." She grabbed a pillow off the couch -- blue, small, and squarish -- and dropped it on the floor.

"Are you sure?"

Lucy gave me a chastising look. You'd think that would be hard based on how she was lying on her groin, getting ready to fuck the hell out of that poor cushion. But, somehow, my older sister still managed to look disdainful. I shrugged and dropped next to her.

I have to admit, changing our surroundings did something to the whole experience. I'm not saying we got bored of the usual stuff, but after weeks of it, there was a sort of numbness to the routine of it all. Doing it in another place -- a room where we spent so much time with the rest of our family -- gave everything a sharper edge.

I went over the top first. Unlike Lucy's peak, mine required some post-orgasm maintenance. So, I got up to go find a tissue. Fortunately, my splooge had mostly stayed in my shorts, though I had a drop or two on my leg.

As I went toward the bathroom, however, I felt a hand on my chest. I stopped in place. Standing in front of me, right at the top of the stairs, was our oldest sister, Jan. My twenty-three-year-old sibling had obviously seen everything. So much for an empty house.

Jan raised her eyebrow at me in a way that was totally different than Lucy's come-hither gesture. It was more like drawing a dagger.

"Tell me you two aren't doing what I think you're doing," Jan said. Even though it was a weekend, she was dressed in a nice, pink blouse and a dark navy skirt. She had her near-black hair tied back in a severe bun. She'd done her makeup, as well, making her angular features appear almost devastatingly beautiful. I felt very much like a turd she'd found on the stairs. "Tell me this isn't what it looks like," Jan repeated.

I paused. I didn't know what to say, except to parrot it back. "It isn't what it looks like," I said. Like that was going to make a difference.

Jan's blue eyes, remarkably similar to Lucy's, hardened.

"It's not," I said.

"OK," Jan said. I braced for the impact. Instead, my oldest sister stared me down for another moment, then spun on her heel and walked away.

Later, I told Lucy about it, expecting her to freak out. Instead, she laughed.

"Don't sweat it," my blonde, older sister said, a smile still playing on her cute face. "Jan's not going to do anything."

"I don't know," I said, "She seemed pretty angry."

"Jan's always angry," Lucy said. I couldn't argue with that. "I'm sorry she caught us. I didn't realize she was home. But Jan's not the tattling type. She's happy to ignore us. Trust me. We just need to be more careful."

Our last brush with danger came soon after. It was by far the most chaste, yet it felt like the riskiest moment of all. Lucy and I had finished dinner and were headed upstairs for our evening session. But as we were about to go into Lucy's room, Mom called after us. Lucy and I shared a nervous look. We walked back down to the kitchen.