Pressing Matters with Sister Pt. 03 - Holiday Break

Last time, Dylan and his older sister Lucy started masturbating together. Then their younger sister Lindsay and Lucy's best friend, Kara, joined in. But now that they've finally been caught, what will come of their conspiracy?

All participants are over the age of 18

"I know what you've been doing," Jan said, glaring at me.

We were standing in the hallway by the bedrooms. My oldest sister stood with her hands on her hips. Nearly as tall as me, Jan's inky black hair was tied in its usual tight bun. She had her head tilted to the side -- a glare etched into her sky-blue eyes.

It was late November, the Sunday after Thanksgiving. For the past four months, I'd been engaging in a spectacular celebration of self-love with my sisters. A few moments before, in fact, the three of us had concluded an epic session where we'd ended up rubbing each other off in a wild daisy chain of mutual masturbation. Like an overcharged orgasmic circuit.

It had all begun in the summer, when my busty, blonde, older sister, Lucy invited me to join her in humping the floor. Then, as the weather got colder, my thin, brunette, younger sister, Lindsay and I had started stroking ourselves together. The only sibling who hadn't been involved in our incestuous fapping festival was Jan.

Except, now she was. And in the worst way possible.

Back in the hallway with Jan -- my oldest sister glaring at me with undisguised disgust -- I stared down at the floor, doing my best to look sheepish. I knew there was no point in arguing it. I'd been caught (quite literally) red handed.

There was no argument for what we were doing, either. No explanation that made any sense. What we'd been up to was beyond perverse. It was really, truly wrong. Of course, that was also the attraction of it. But I wasn't going to tell my oldest sister that.

Instead, I stood there, avoiding Jan's gaze, and hoping to hell she would go easy on me.

"I know what you've been doing," Jan said, a smirk edging across her thin lips. "And I want in."

*

Jan had always been distant from the rest of us. Like she was one of the adults rather than a kid. She had a kind of aloof maturity -- even when we were all very much not mature -- that set her apart. The age thing played into that. Whereas we were kind of clumped together (Lucy was 21 to my 19 to Lindsay's 18), Jan felt oddly older at 23. It was more than that, however.

Even in high school, Jan dressed prim and proper. We didn't attend a private school, but Jan always had a uniform: dark skirt and hose, white dress shirt, her hair tied up so tight it strained at the roots.

When Jan left for college, I honestly thought that was the last we'd see of her. She came back for holidays, but even then, she was more of a shadow than a sibling. After Jan graduated school, she really did almost disappear. She had a promising career, a lovely apartment in the city, and a fiance for whom the best description was 'appropriate.'

But when things went in the crapper -- when Dad lost his job and we had to give up our house and our lives in payment for his mistakes -- Jan moved back in with us to help out. Coincidentally or not, Jan's engagement broke apart at around the same time. While Lucy, Lindsay, and I attended school, Jan went to work. She wasn't Mom or Dad, and she didn't play at being them. Jan seemed more like a cool aunt or a hip neighbor or something like that.

My oldest sister was an oddly distant mystery. A foggy mirage, staring at us from some other remote place, even when she was sitting at the same table and eating the same meal.

Which only made my sister's reaction that afternoon all the more alarming. I don't think Jan intended it as a threat. Especially in retrospect, I know that she wasn't trying to menace me. It's just how it felt, in that moment, when she held me under the knife.

*

The next day was a Monday, and we all returned to our routines. Mom, Dad, and Jan all left before the rest of us were awake. Once again, Lucy dropped Lindsay off at the high school, then drove the two of us to our own classes at the community college.

The whole drive, the car was oddly silent. We didn't mention how we'd busted through all kinds of barriers the day before. How Lindsay had sucked my dick. How I'd fingered Lucy to a spectacular finish. How we'd egged each other on the entire time. What we'd done had been beyond anything we'd shared before. And what was worse (better?) it had only felt like a warmup for something way more intimate.

We'd been so easy with each other the day before. It made the discomfort of our morning commute seem even more oppressive. To be fair, not talking was normal for Lucy and me. Our shared sessions had always been a strange, unspoken agreement.

But the silence was downright odd for Lindsay who often liked to go through things blow-by-blow (pun definitely intended) like a hot John Madden, reliving every moment in detail before announcing her plans for more mischief later in the day.

I honestly didn't know what was going on. And I couldn't ascribe the awkwardness to Jan because I hadn't told my other sisters what had happened. Partially because our oldest sibling had asked me not to. Also, though, because it felt like it was my issue to deal with. I didn't want to drag my other siblings down into the morass we'd made.

After we dropped Lindsay off, I came out and asked Lucy about it. The awkwardness, I mean.

"I think we're all settling back in," Lucy said, "With school and stuff. We always tend to be a bit more laid back around the breaks, right?"

"I guess so," I said, "I just hope I didn't do anything wrong."

"Oh no," Lucy said, a lascivious little smile playing on her lips. "In fact, I'd say you did everything right."

I let out a large sigh of relief. I wanted to believe my older sister was correct. I really did.

"Look, we've got three more weeks of school," Lucy continued, "But after that we have a whole eleven days off. I counted. We need to keep our heads down for a little longer. Then we can celebrate for real."

After classes, we came home. Any concerns I might have had following our morning commute were quickly put to rest when Lucy, Lindsay and I did the most normal thing possible: we went for a quick press in the living room before heading off to do homework. It was both weird and reassuring that such a lewd act was the thing to settle my nerves rather than stretch them out.

But there was still the problem of what my oldest sister wanted. I know, it probably seems obvious (in retrospect it was fucking obvious) but at the time I truly didn't know what to make of it.

I want in. What did Jan mean by that? Was she going to join Lucy, Lindsay and I and rub herself off on a pillow? I couldn't picture it.

I mean, if I thought about it (and to be fair, it wasn't the kind of thing I'd ever thought about till that moment), I wasn't even sure Jan masturbated at all. Not that I was keeping track of such things. It was just that my older sister didn't seem the type. Oh sure, she had several serious boyfriends -- one in high school, two in college, then Mr. Milquetoast-the-fiance-that-was-no-longer -- and so I imagined she'd done lots of stuff.

But thinking about my oldest sister abandoning herself to illicit pleasure? This was the girl who'd once celebrated going on a thrilling water slide by saying 'hm' and heading back to her chair to read a book. Jan wasn't exactly a slave to her baser desires. I wasn't sure she even had baser desires. So as 'duh' as I'm sure her comment seems to you all, the idea that my sister was going to rub one out with all of us seemed pretty ridiculous.

But, if not that, what could Jan's words mean?

It's hard to explain how fraught and broken this all felt. The exultation of what I'd shared with Lucy and Lindsay the day before mixed with the curiosity and concern of what Jan had said soon after. Like honey mixed with ghost peppers, burning as it slid so sweetly into my stomach.

I was left to ponder it for hours. That night, we had dinner as a family (Lucy and I on the couch with stack tables). I caught Jan's eye at one point, and she arched an eyebrow. But nothing more. We washed up after, then broke to our separate rooms.

I sat at my desk and opened books to study. Midterms were only a few short weeks away, as Lucy had reminded me, and I needed to get to work.

The day was already quite dark. The house grew quieter, except for the little creaks that this old place always let out. Like the specters had to settle in, as well. At a certain point, I realized that whatever Jan had meant, I wasn't going to find out that night. Or maybe ever. It all seemed so impossible.

Right as I was about to give up and go to sleep, I heard my cell phone buzz. I picked it up and looked at the screen. One word from Jan.

"Come"

*

Slipping into Jan's bedroom felt odd. My oldest sister's forbidding nature made her personal space seem all the more foreboding. Even back in the old house, after Jan had left for college, I was uncomfortable going anywhere near her stuff. Like she'd left a curse on it all or something.

I closed the door behind me carefully, my breath sharp and thin in my chest. Jan's bedroom was as dark as the rest of the house, but I could still make out her spare, utilitarian furniture and oddly bare walls. And, most importantly, I saw my oldest sister, lying back on her bed in a plain white t-shirt and pink, plaid pj pants. She had a book on her lap, like she was up to nothing outside of normal.

Jan saw me enter and a wicked grin filled her face. She raised her eyebrow in that usual inquisitive way, then sat up. Jan was tall, nearly my height, like Lucy. But she was willow thin like Lindsay. Each of us a slight variation on the other in a way that made us look quite unique yet all from the same source. Weirdly familiar and oddly distinct. Siblings, in other words.

Jan patted the bedside next to her and I sat down. For a moment, we both just sat there. I swear I felt the air around me tighten. Even breathing was an epic undertaking.

"Well," Jan said.

I nodded.

"Well?" Jan asked.

For a moment, I was taken aback. This whole time, I'd been assuming that my oldest sister would drive. That she was taking the lead because she was the one who'd demanded it, right? And wasn't Jan always in charge anyways?

But I realized that wasn't true. I'd been the one who'd begun all this (well, technically, Lucy had started it but that was nitpicking). If there was an expert in shared sibling stroke sessions, that person was me. Jan asking in wasn't a threat, it was a request. And now that she'd RSVP'd, it was only natural for her to assume that I'd be starting the party.

I cleared my throat, apologetically. "Usually we'd..." I gestured to the floor.

"Don't be ridiculous," Jan said. There was the oldest sister I knew and loved/feared.

"OK, well, um. I mean. I'm not sure how you like to, you know. Go." I know, great public speaker me. I could run for governor with that kind of eloquence and clarity.

Jan sighed, a sound that let me know she was both disappointed in my performance but also not at all surprised that I'd flubbed it in the first place. She reached over to her nightstand, lifted up a bunch of papers, and retrieved a purple dildo. I'd have been less surprised if she'd pulled an elephant out of there.

The fact that Jan had a toy at all was already a huge shock. The fact that it was so outrageous and lewd, clearly not a beginner item, nearly blew my brain right out the back of my head. I mean, this was a dildo.

It was bright, Barney-purple, and so long it would shame a porn star. And thick. And covered in ridges and bumps. And curved in ways that I couldn't imagine would feel good. And... It looked like a farce's idea of a sex toy -- so over the top that I started to wonder if my oldest sister was messing with me.

Wordlessly, Jan got off the bed. She took her desk chair and wheeled it over to the side, so she was facing me. Then, like it was nothing at all, she shucked off her bottoms, revealing a trim, tidy pussy with a stripe of dark pubic hair. Jan sat down and spread her legs. She held the dildo precipitously over her pussy. The purple, plastic cock of Damocles waiting to plunge.

Jan cleared her throat again. It was not a pleasant noise. I pulled down my sweats and boxers. While my big head had been off in the clouds, my littler one had clearly been thinking of something different (Sisterpussy! I could practically hear it screaming). My dick popped out epically hard and already pulsing.

I sat back on the bed, my cock pointing upward like there was something super interesting on the ceiling that it needed me to see. I don't know what I expected from my sister after my big reveal. But I definitely didn't anticipate the way the usually aloof woman licked her lips, smiled, and said, "Nice."

Jan flipped a switch and her already absurd phallus jumped another level as it started to buzz and shake. The toy practically undulated in her hands. A moment later, she let out a little gasp as it made contact with her clit.

I might have been off in space -- completely stretched between shock and arousal -- but I knew my cue. I grabbed my cock and started to slowly stroke it. I felt myself already on edge and I wanted to make sure I got to watch Jan go first.

In that moment, I realized how apex sexy my oldest sister was. Jan didn't have Lucy's killer curves or Lindsay's libidinous personality. But Jan's body -- those long shapely legs, the hint of her taut bubble butt, that tight little twat. My oldest sister was an absolute smoke show, and I was already regretting not telling her to take her top off.

The fact that Jan was usually so serious, so reserved, only made this moment where she surrendered to her own sexuality feel even more exciting and raw. Seeing her private self -- the way her lip curled and her eyes unfocused; how her knees raised and spread almost subconsciously. Jan was like a living aphrodisiac reclining in a desk chair.

God DAMN I'd underappreciated the opportunity I had before me. Then, as if it wasn't already too much, Jan started talking.

"Such a naughty little brother. Stroking that big cock in front of your sister."

I'd have done a spit take if I'd been drinking. Jan's words were so fucking hot, my dick almost did its own kind of spit take right there.

Jan's voice went low and raspy. It practically thrummed with need. She could have told me to jab a pencil in my eye with that tone and I'd have agreed without hesitation. Fortunately, she only wanted one thing.

"You're not supposed to do that -- oh! -- little bro," Jan said.

She continued to tease at herself with her toy. The dildo no longer seemed silly at all. No, that lavender monstrosity was now deadly serious. And all I could think about was how badly I wished I could take its place.

"Nasty, wicked boy," Jan continued. I wondered if she had even an inkling of how much power she had over me in that moment. "Watching your big sister get off."

I figured she probably wanted me to talk back but when I started, she shushed me.

"Bad enough you're rubbing that big dick for me," Jan said, "Watching me make myself feel so good." That last word devolved into a low groan. A throaty "ohhhhhhhhh" that, on top of an already incredible performance, might have been the sexiest thing I'd heard yet.

We sat there, getting ourselves off. The room filled with our shared grunts and groans. The slicking sound of my palm stroking loose skin. The droning hum of my sister stimulating her clit.

"You getting close, little brother?" Jan asked, "You going to cum? Naughty boy spurting his stuff in front of his sister?"

I could only nod my head in agreement.

"OK," Jan said, "Let it all out. It's OK, it's our secret. I won't tell. It's OK to let your sister see.... OH! OhhhhhhhhhhOH!"

Jan shuddered. She shook. With a trembling hand, she reached up for her left nipple and squeezed it, hard. Her bright blue eyes rolled back in her head. Her legs went stiff as her toes curled back and her whole body clenched.

It was more than I could take, and I erupted. The pleasure raced through me sharp as lightning and full as thunder. An arc of white spurted across our bodies, landing on Jan's leg.

I thought she'd get grossed out, but as my sperm hit her flesh, Jan's orgasm seemed to go to another level. She choked out a little ecstatic sob. My next shot, I didn't see where it went. The bliss overwhelmed me, and I lost track of anything except the pumping, pulsing pleasure as it engulfed me, body and soul.

When my eyes gained focus, I found myself gasping for air. My dick was slowly softening in my hand. Sticky from my spend.

Jan was staring at me, a bemused expression on her face. A strand of her dark hair had escaped her bun and she blew it away from her eyes, only for it to settle back where it'd been before. She let out a little sigh.

"Well, that was fascinating," Jan said, "Let me get you a tissue."

I could tell Jan's normally serious nature, her mask of indifference, was slowly slipping back on. But it was incongruent with the way she stumbled around her dark bedroom looking for a box of Kleenex. Finally, she handed me a wad. She took some for herself and I watched her run it from her calf to her thigh.

"You let out a lot," Jan said, "You must have been super backed up."

I didn't have the heart to tell her that, actually, this was already the second time I'd spent with a sibling that day. Instead, I just nodded. I was weirdly proud of myself for cumming so much. Like I'd accomplished something laudable solely by producing copious semen on command.

"Whew! I needed that," Jan said. She chuckled, a soft thing, then lay back down in bed.

I stared at my sister, a bit in awe. She went back to reading her book. Her face so expressionless. And yet the woman I'd seen a moment before was still there, right beneath the surface. It was so fucking hot, yet also oddly intimate.

"Have a good night," Jan said.

It was the only post-mortem I'd ever get from her. I stumbled back to my bedroom, shell shocked. My God. Whatever I'd pictured when Jan had pulled me into her bedroom after catching us. Well, it certainly wasn't that.

There was no doubt in my mind now, the next few weeks were going to be an epic experience.

*

The next few weeks were boring as hell.

Like Lucy had predicted in her car that morning, we all got swallowed up in the responsibilities of school, work, and life. Lucy, Lindsay and I would press every couple of days (we were busy, not insane). Two more times, Jan called me into her room on a quiet night and we rubbed off in front of each other. But my sister kept her panties on, left her crazy dildo in her drawer, and barely made a sound. Even as she climaxed.

If I'm making it all sound banal that's because, honestly, it kind of was. Well, in the moment it was hot as hell. It was still masturbating with my sister. But, similar to the pressing I did with Lucy and Lindsay, it felt both very rushed and also quite routine. Like brushing our teeth together or something like that. If anything, jerking off with Jan made me feel more like a prop, a porn video she could call up at will, then swipe away once she was finished. I can't say I wasn't using her the same way.

At the same time, like my mind had been partitioned, I couldn't stop thinking about what had happened that first night -- the dirty talk and all that. I know that sounds ludicrous. We were, literally, getting off together. And I was rubbing it out with my two other siblings every few days, as well.

But I spent a good amount of my free time fantasizing about all the other stuff we could be doing when we actually had time to enjoy it. That's beyond covetous, it's fucking crazy. But knowing that and stopping it are two different things. As any addict will tell you.