Pressing Matters with Sister Pt. 03 - Holiday Break

I think part of it was the anticipation. In that way, it was almost fun. Before, when my sisters and I had hit dry spells, I'd worried we might be reaching the end of our adventures. But this time I had no doubt we'd be back to doing things as soon as school let out. I just wanted that time to come as quickly as possible.

Finally, as the holidays grew closer -- as midterms finished and classes closed, and a light dusting of snow covered the roads in anticipation of Santa's arrival -- we all started to awaken from our sexual slumber. Like a group of incest-obsessed, libido-driven, hibernating bears awakening to meet the dawn.

Two days before the break, Lindsay caught my arm as we did the post-dinner dishes. She didn't have to say a word, I could see what she wanted by the glint in her eye. But, being my younger sister, she said it anyway. Right out loud.

"I want to do our thing," Lindsay said. Her fingernails bit into my bicep, right through my sweater. Instinctively, I looked around for Lucy (we'd been kind of a package deal), but my older sister was out with friends. "Just us is OK."

"What thing is that exactly?" Mom asked, eyebrow arching in a mirror of her oldest daughter.

Like I said, Lindsay and I were standing right there in the kitchen. And my little sister had been none too quiet about her request. Talking loudly over the running water and all. God, but Lindsay had a way of getting us in trouble.

Fortunately, she also had the ability to talk herself right back out of it.

"Videogames," Lindsay said, flightily, tilting her head.

"I thought you didn't like that stuff," Mom said, "You gave me that whole speech about how it's all empty and meaningless. Spiritually bankrupt." My mom did air quotes as she spoke the last two words.

"Yeah, but then Dylan showed me this neat game where you grow vegetables and you have to collect different seeds, but they only grow during select seasons and they change each day so..."

And my sister was off to the races. I don't know if her rambling was on purpose or just the way her brain worked but it didn't matter because in moments it was clear our mom had completely checked out of the conversation. It was such a good cover that I could almost forgive my sister for causing the chaos in the first place.

Once Mom was subdued, we finished washing and Lindsay led me up to her bedroom. She carefully closed the door, then flopped down on the floor. Without even a preamble, my little sister took her top off. Now she only had on a purple sports bra with striped, black-and-white yoga pants.

"Come on Dylan, don't waste time," Lindsay said, "I need your energy to weave with mine."

"Uh huh," I said, not buying into my sister's mumbo jumbo any more than I needed to get off. "Everything?"

"Heck yeah, everything!" Lindsay said. She pulled her bra up over her head, revealing her little, pinkish breasts. Then she stripped off her bottoms as well, leaving her completely bare. Lindsay's pussy was completely shaved; it looked so full and welcoming. Damn, my baby sister had a great body. Lithe like a sculpture, yet soft and warm and oh-so-sexy.

Lindsay let out a little happy gasp when my dick popped free. She reached out to grab it, instinctual, but stopped herself. I tilted my head at her, but my little sister didn't explain. Instead, she brushed her impossibly long brown hair out of her eyes, reached between her legs, and started rubbing.

"That looks so good, Dylan," Lindsay said. Her green eyes focused on my dick like it was the center of the universe.

"You look so good," I said. I know, again, judging my vocabulary while my dick is in my hands isn't the fairest thing in the world.

It didn't take long for either of us to get off. Lindsay let out her usual high-pitched squeak as her body folded in on itself. I wasn't far after, spurting hot seed all over my sister's incredible little body.

"Oh Goddess," Lindsay groaned, "I can't wait to have your stuff inside me."

*

The next morning, one day before break, Lucy jutted her chin at me over breakfast. I couldn't hide my confusion. My older sister couldn't possibly mean she wanted a press. Sure, my parents and Jan had already hit the road. But didn't we have school?

"My finals are finished," Lucy said, "And you don't have a test till this afternoon."

"Oh," I said, "Right." Was it weird that my sister knew my schedule better than me? Was it weirder that that wasn't even in the top five of weird things between me and my sister? "But what about Lindsay?"

"She told me she already got hers last night."

I did my best not to blush. "Still, don't we have to drive her to class?"

Lucy's mouth quirked, but it quickly shifted into a big, dirty grin. "Yes," my older sister said, "Yes we do."

The three of us got in the car. Lindsay didn't question why it took two siblings to take her to school. Maybe it was my imagination, but she seemed a little spacier after our evening session. Like the lingering fumes of her orgasm were still leaking out of her.

After we let Lindsay go, Lucy headed back home. But after my older sister took a few turns in a different direction, we found ourselves rolling down a quiet road. I recognized we were going towards the nearby nature preserve. Though I didn't think Lucy was looking to go bird watching.

We turned down a gravel path and parked in a spot on the side of the road. It was early in the morning on a weekday; the little lot was empty. Lucy switched off her car and stepped out, stretching in the frigid air. I climbed out on the other side and eyed her.

Lucy was wearing a long white coat that went down past her knees. She had on a matching, knit white hat. Her blonde hair hung down in braids on either side of her face. Lucy's cheeks were already ruddy, making her blue eyes seem to sparkle even more than usual. It was cold enough that I could see her breath.

We trudged down a rock path, past bare trees and snow-dusted rocks. Our footsteps crunched loudly on brown leaves. The place was beyond empty; even the animals had decamped for the season.

Turning past a boulder taller than the two of us combined, we came to a tiny, open picnic area. Several wooden tables were scattered next to rusty, metal barbecue stands. The clearing was surrounded by tall, thin trees.

The scene was peaceful, quiet, but my sister was anything but. Lucy shoved me back onto the top of a picnic table. She reached for my belt, and in seconds, my pants and boxers were around my ankles. The wooden table felt icy on my bare butt. But my cock knew what was coming and was already at attention. I swear I could see steam coming off it.

Lucy stood over me. She unbuttoned her coat but left it on. Then she stepped out of her pants. My older sister's amazing blonde pussy was right in front of my face. Despite everything we'd done, I'd never gotten a good look before. Like my other sisters', it was perfect (and I'm aware of what a weird thought all that is).

For a moment, I thought Lucy was about to full-on mount me, breaking a barrier we'd set up months before. But my older sister wasn't all the way back to that place. Not yet, anyway.

Lucy did climb on top of me, but her head was by my crotch, putting her sweet, soft sex in the right place for my tongue. There was no need for further explanation. We went at each other like we were crazed. Wild.

The cold had a part in it for sure. Every time my dick slipped from Lucy's warm mouth, I swore it was going to freeze right off. But it was more than that. We needed each other. Craved the lewd, depraved intimacy of it. The wet, loud, sloppy slurping that removed any doubt that we were animals in heat.

Before, Lucy had cleaned my dick after Lindsay had sucked me off. But she'd never actually given me head. My cock had been in my sister's pussy but never my tongue. Yet the two of us plunged into oral pleasures in public like practiced savants. We brought each other off with the ardor of the starving. When my sister came -- her clit jammed under my tongue -- her shout echoed through the thin winter air. My own cum spurted out of me, hot, soon after. Lucy gulp, gulp, gulped it all down.

We lay on top of each other, panting. Suddenly, I felt exceptionally cold. Lucy leapt off me and threw on her pants. I did the same and we raced, shivering, back to the car. Lucy laughing hysterically as she fumbled the keys to finally fire up the engine. She blasted the heat as high as she could.

I looked over at my sister, trembling. She shot me a similar expression. This was utter madness. Complete, ecstatic, blissful insanity. I didn't ever want to let it go. The heat finally kicked in and I stopped shaking. Lucy sucked in a deep breath and let it out as a sigh. As we stared out the windshield, a few snowflakes drifted languidly onto the glass.

"I'm happy," Lucy said out of nowhere.

"Anything in particular?"

"No," Lucy said, "All of it. None of it. The last few years have been... I'm just happy."

"Me too."

Another pause. Lucy seemed to be tumbling something around in her mind. Finally, she oriented it in a way she was comfortable with and let it slide out.

"Remember Randy Hotguy?"

"That dude you had a crush on at school?" I remembered him.

Lucy had brought him up as an example of someone she thought about when we pressed, back in the beginnings of all this. She didn't know his name, he was a random hot guy, so we named him that. Kind of as a joke.

"He asked me out yesterday."

"Really? That's, um. Yeah, wow. That's great."

"I turned him down," Lucy said.

"What? Why?"

"You know why."

I supposed that I did. But we weren't supposed to say those things out loud, were we?

"Look, I don't know what this is," Lucy said, gesturing between the two of us "But I know that I want it."

"Me too," I said. I hadn't even realized it till that moment. But I knew that it was true. It couldn't be love, not between siblings. Not in that way. But here we were, and I didn't ever want it to end.

"Yeah?"

"Yeah."

"And everything else? All the stuff that comes with it?" Lucy asked.

"We'll figure it out," I said, more confident than I felt. "What about Lindsay?"

"What about her?" Lucy asked. She flipped down the sunshade and opened the mirror, checking her face for any evidence of my spend.

"I guess she's part of this now," I said, "We all are." I didn't dare say the J-name out loud. At least, not yet.

"I don't mind Lindsay," Lucy said. A little smile played on her face. "As long we're, you know, us."

"Lindsay wants to have sex," I said, "Not just what we've been doing. You know. All the way. She keeps talking about it."

"So?"

"Well, I mean. I don't know if it's a good idea," I said, "She wants me to do it. To finish. You know, in her."

"I don't blame her," Lucy said.

"You don't think it's, like, a bad idea?" I asked, "Beyond the sibling thing. What with the risk and all?"

"I think it's none of my business what you and Lindsay do together," Lucy said.

I gave my sister a jaundiced eye.

"Fine," Lucy said, "I guess what I mean is, it's not up to me. But personally? I think you should go for it."

"Seriously?"

"You've done almost everything else with her," Lucy said, "What's the big deal, honestly?"

"Even after what happened with you and me? When I... When we almost..."

"I think a lot about that too," Lucy said, "I have a lot of regrets."

"I'm sorry," I said, "I screwed up. I'm so stupid. I can't tell you how awful I feel about all of it. The danger I put us in."

"Stop," Lucy said. She put her fingers on my lips. "The only thing I feel bad about is that we stopped."

*

That night, I couldn't sleep. I lay in bed, staring at the ceiling, searching for answers to questions I didn't even know how to ask. My hot younger sister (who was very much not on birth control) was outright demanding intercourse. My gorgeous older sister was straight up searching for a real relationship. Both requests felt impossibly foolish yet undeniably inescapable. I should have felt like I won the lottery. Two beautiful women wanted to be with me and neither minded the other, to boot. But don't most lottery winners also end up horribly depressed and miserable?

My phone buzzed and I looked down. For some reason, it showed me the text that Jan had sent two weeks before.

"Come."

Then I realized -- my phone wasn't notifying me about an old message. I'd gotten a new one. I popped out of bed like it was burning hot.

The house was silent. Everything was pitch dark. The next day was Christmas Eve, and I could make out a few branches of our undecorated tree at the end of the hall. I turned to my oldest sister's bedroom before I got there -- I knew a much better present was waiting inside.

Once again, I found Jan in bed, reading a book. She had her dark hair up in the usual bun and she was wearing her reading glasses. She had on a silky, black top that, if I didn't know any better, I'd swear was lingerie.

Jan nodded and took off her glasses when I came in. She slid out from under the covers to reveal a pair of matching dark shorts. She didn't say a word, just sashayed over to the desk chair and put it into place. Then she reached into her drawer and pulled out her lavender companion. I smiled and, this time, it wasn't from mirth. I was legitimately happy to see the fellow. It meant that I wasn't here for a quick stroke. We were going to have FUN.

As if to confirm my thoughts, Jan stood up and immediately stripped down. I hadn't seen her naked the last time and it was, truly, a revelation. Jan didn't have Lindsay's toned tummy. And she lacked Lucy's massive breasts. But my oldest sister's body was beyond what I could have imagined. Her breasts were full, yet perky. Her hips flared out at a perfect curve. Her long legs and trim flank -- it was like finding a goddess living in my sister's bedroom.

As a grand finale, Jan reached back and undid her hair. It fell past her shoulders in waves like liquid onyx.

Fuck. Me.

"What?" Jan tilted her head. She'd caught me drooling, no doubt.

I responded by stepping out of my own clothes. There was nothing I could say that would explain to my oldest sister exactly what she'd shown me. And while I knew my own body couldn't compete, it was the only card I had to play. Fortunately, Jan eyed my dick with the same perverted wonder that I'd just given her. She grinned, wickedly.

Jan sat down on her desk chair, spreading her legs like a swan's wings. She dipped her dildo to her clit, then flicked it on. The room filled with a buzz and a gasp.

I took my place on Jan's bed, facing her. My cock firmly in hand. I gave it only the most cursory of strokes. I was going to enjoy this show for as long as possible. Plus, I had another plan in mind. One I'd been working on for the last two weeks, hoping I'd get another shot at this.

"Such a naughty sister," I said.

Jan's eyes went wide. Her leg kicked.

"Bad little girl, showing your little brother your pussy."

She gasped. Her eyes rolled back. Just like that, a few well-placed words, and already I'd made my sister cum. A tiny one to be sure, but no less magnificent for all that it meant.

"You like that, little perv? Watching me cum?" Jan asked. Her azure eyes were alight -- now that it was clear that I got the game, it was time to take the gloves off and play.

"Sick sister, you want your baby brother's cock, don't you?" I started to stroke myself faster, practically waving my dick at my sister like a scarlet cape at a bull. "You're not supposed to want that."

"Gross brother, staring at sissy's pussy," Jan snarled, "You want to -- OH! -- stick it in me, don't you? That's incest."

"You wish," I said, "You'd love to feel your brother's long, thick cock fill your forbidden cunt. You're practically pissing on the floor you want it so bad."

"Oh... OH!" Jan's legs kicked out. She reached with her free hand and pinched her left tit purple. She let out a long, anguished squeal of delight as her orgasm overtook her. This wasn't the little bump of before, it was a mountain. And my older sister howled as she soared off the cliffside.

By the time she came down, she was bathed in sweat and her own slick juices. Her thighs shiny. Dark hair stuck to the side of her face. Jan dropped her dildo to the floor. She looked beaten, but her eyes were so intense -- so filled with erotic energy -- they looked ready to power a whole city block.

"Do it," Jan said, her voice ragged and thin. "Cum on your sick sister. Cover me with your thick, incestuous seed."

I jammed at my cock with abandon. All my patience from before was working against me. I stood up, pointing my dick in Jan's face. Stroked like an animal.

"You want that brother dick," I said. Forcing out each word felt like a phenomenal effort. "That sibling spend. You want my load on your face. On your tits. In your unprotected pussy."

"Oh GOD!" Jan's legs kicked out. She hadn't even touched herself, but the orgasm showed up anyway. Her eyes rolled back in her head, hard.

My own ecstasy grabbed hold of me. I spurted onto my sister. A thick glob of pearlescence spattered her right on her face. The next hit lower, on her lovely breast.

"Uhn...naughty boy." Jan gasped out. "Cumming all over your big sister."

Jan tumbled out of the chair and onto the floor, still shaking on the ground. I stood over her, as if my sister was a precious flower and I was watering her with my cum. Like she was an inferno, and this was the only way to put her out.

I lowered myself to the ground next to Jan. My cock was now soft and sticky in my hand. The bliss continued to roll over me. We sat there on the hard, wood floor. Barely touching. Glorifying in our shared ecstasy.

My breath slowed. The orgasm drained out of me. I felt awkward but satiated. Jan snuggled up next to me. She wrapped her long arms around my shoulders. I tried to think of the last time my oldest sister had hugged me. The only answer I could come up with was 'never.'

"Such a good little brother," Jan said. She kissed my cheek, lightly. I realized she smelled a bit like licorice. "Making your big sister feel so good."

Jan let go of me and climbed back onto the bed. I started to make my way to the door. I don't know why it all came to me at once, how odd all this was. Lucy and I had always been close. Even before the pressing. So, it felt natural to me, in a very unnatural way, that we'd fallen into things together.

With Lindsay, I don't know. I guess that didn't make much sense either. But my younger sister had a way of making upside down seem right side up. It was merely a matter of seeing things from her perspective. Of course we'd fool around. Whyever not?

I couldn't say the same with Jan and I guess that got to me. Was this just fun? Or something far more dangerous?

"What are we doing here, really?" I asked my oldest sister.

I turned around to face her. She was under the covers. Her black hair was already back in its bun. Her nose buried in her book. Jan cocked her eyebrow in that signature expression of hers. Like a sexy Mr. Spock.

"We're masturbating?" Jan said.

"Yes, I get that," I said, "I mean, like, what are we doing?"

Jan let out a long sigh, like I was the most exasperating person in the whole universe. As if my question wasn't actually so overloaded with merit that it might tip us all over.

"I'm stuck home," Jan said, "I have nothing to do except work. And seeing you, Lindsay, and Lucy together? Well, I guess you three found a way to make the time pass. Better than reading books, anyway."

"It has its benefits," I said, with a wry smile.

"So why can't I enjoy it, too?" Jan asked.

I nodded my head. That made sense in a very Jan way.

"So, this is all because you're bored," I said, "And a little jealous?"