Pressing Matters with Sister Pt. 04 - Spring Break

"Seriously?" Lucy asked. I could hear the skepticism in her voice. "That's your plan?"

I shrugged. Excellent dialectic, I know. But my younger sister had my back.

"Oh, come on," Lindsay said, popping out of her chair. "Don't tell me you couldn't go for one right now."

"Fine," Lucy said. She stood up, scraping her chair loudly on the hardwood. "I can't believe I'm missing Mickey for this."

The girls grabbed some pillows and we all flopped onto the floor of the living room. It wasn't anything special. We didn't talk to each other or even acknowledge what we were sharing. The three of us wriggled our genitals into the ground before reaching the inevitable peak. It was almost clinical.

When she was done, Lindsay leapt to her feet. "Whew! I needed that. Thanks, Dylan!" She skipped up the stairs, then stopped and turned back to me.

I was slowly standing up, doing my best to ignore the wet spot in my sweats.

"Hey," Lindsay said, "Cause it's break, I'm doing a class this afternoon. You know, if you want to join."

"I'd love to," I said, giving her a little wave as she bounded up the stairs.

"You do yoga now?" Lucy asked, looking up at me from the floor. Don't think I missed how her massive chest jutted alluringly under her sweater.

"I support my sister," I said.

"I see," Lucy said. She brushed off her pants. "And if you had a sister who maybe wanted to spend some time taking down Ganon, you'd be willing to assist with that, as well?"

"Lead the way, my Link," I said, bowing graciously.

*

I lay in bed that night, staring up at the ceiling. My muscles ached from working out that afternoon with Lindsay. My eyes thrummed tired from staring at the screen all morning with Lucy. My body, though, was ready to take the next step with yet another sister.

I waited for my moment. Till the sounds of the house quieted down. And the lights went low. Like a cat hunting its prey, I stayed nearly still till I knew the time was right. Finally, I picked up my phone and typed in that all important message.

To Jan: Come

No response. I knew she was in her room. Was probably reading and wouldn't be looking at her phone. Ten minutes passed with nothing. I tried again.

Come

Come!

COME!

Jan finally wrote back. "?"

I responded. "Cum?"

I heard a door shut in the distance. Then footsteps padding in the hallway. Finally, a knock on my door.

Abruptly, I worried that I'd made a misstep. Jan's movements didn't sound like those of someone who was super excited to be heading over to my bedroom. I braced myself as my door swung open, hoping I hadn't upset her too badly.

My smoke show of a sister stepped in front of the bed. Her black hair up in a bun. She had on that black lingerie -- the silky, button-down top and shorts. They revealed nothing. But Jan was so damn sexy it didn't matter.

"I thought we weren't doing this anymore," Jan said. She eyed me like I might be hiding a gun behind my back. My actual weapon was already standing at the ready in my sweatpants.

"Who told you that?" I asked, dismissively, then gestured for Jan to join me.

My oldest sister eyed the walls, warily. I patted the side of my bed as I stripped from the waist down.

"Did you really invite me in here just to..." Jan's face formed a sneer.

"Duh."

There was a pause. A moment where we both stepped off the precipice and everything I'd planned hung in the balance.

"Such a naughty little brother," Jan said, now smirking instead. She took off her shorts, spreading her legs as she lay back next to me.

"You should have brought your toy," I told her.

Jan looked at me, then raised an eyebrow. "I have a better idea," she said. Her blue eyes alight.

Jan got up and headed towards the foot of my bed. At first, I have to admit, I was confused. Then I noticed that Jan was making her way over to one of the corners. My frame had little wooden bedposts, each about waist high from the floor and squarish. I heard Jan let out a little gasp. I didn't need to see to realize what she was doing.

I didn't need to see, but damn sure wanted to (not that the view of Jan's undulating ass was all that bad, either). I leapt off the bed and hurried over to the far corner so I could see what my sister was up to.

As I'd surmised, Jan was on her knees on my mattress, her sex pressed against the small bedpost. It was smaller than a standard dick, thinner and shorter (and squarer), but I had to admit the thing was sort of penis-like. Especially when pressed into my sister's furry furrow.

I slid my desk chair over, cock in my hand. Like she didn't see me at all, Jan rubbed up and down on her new, wooden friend. Humping it against her clit. My oldest sister pulled off her shirt, mid thrust, squeezing both her breasts and groaning. It was like she was giving me a show. Yet at the same time so lost in her world of pleasure she hardly noticed me.

Jan pumped against the frame. She pinched her nipples purple. The post was hard and sharpish on the edges. I had to imagine there was a good amount of pain in what she was doing. But some part of me realized that was the point. Jan liked to punish herself. That was part of the pleasure of it.

"You're such a bad big sister," I said, smiling up at her.

I lazily stroked at my dick, enjoying the performance. This was almost as good as when she brought out her lilac dildo. In some ways it was better. Working herself like this took Jan's entire body. Fuck me, this was beautiful.

"You want it," Jan said, "Naughty brother. Wish it was you. Fucking me. Don't you?"

I could only nod my head in agreement. She knew damn well I did.

"Naughty boy," she said, "You can't put your -- uhn -- cock in your sister."

"You're the one that wants it so bad," I said, "Feel my dick inside you. Pumping you full."

"Oh. OH! Such a... Bad brother. Making sissy feel GOOD!"

Jan arched her back. She squeezed her left nipple so hard I swore she was about to pull it right off. Her entire body went taut. Like she was posing for an old-timey picture and had to stay in place for hours on end. I could see back on the bed, her toes were literally curling.

It was all I could take. Being honest, I'd barely even worked myself. But it didn't matter. My dick spurted out, spattering my oldest sister with my seed.

"Oh YES!" she cried out again as my first ejaculation splashed her. A stripe of white splooge that painted her from shoulder to waist. The next one hit her tit. The third... I was too far gone. I couldn't see anything except wave after wave of unbridled ecstasy as I unloaded on my sister.

Jan fell back to the bed, panting. The bedpost, abandoned, dripped girl cum down onto my sheets. She hugged my pillow, burying her nose in my scent.

My cock hung limply, spitting the last of my spend into my palm. I tumbled out of the chair and climbed into bed, spooning against my naked sister. She shifted, pressing herself as close as possible. Jan's body, for all her angles, was surprisingly soft. I couldn't help myself -- I untied my oldest sister's inky hair and ran my hand through it. Cool and silky, like her lingerie from before.

"That was fun," Jan said.

"It was."

"Why did we stop doing that again?" Jan asked.

"I honestly don't know," I said.

"Lindsay and Lucy...?"

"They're fine," I said, "They already know. I told them."

"OK," Jan said. She was doing the sleepy mumbling thing. I felt her body go limp. She was going to pass out here in my room, naked, and I had no intention of stopping her. Anyone could find us together. More importantly, I didn't care.

Jan's head popped up, like she'd been having one of those falling dreams. "Dylan?"

"I'm here," I said.

"I lied before," she said.

"I'm actually a good brother?"

"The best," Jan said. That seemed to be it for a moment. "No, I mean before before. Like way before. In December. When I told you I don't do angry or jealous or sad.

"I know, it's OK."

"I just felt so alone. Ignored," Jan said, "I was working like a dog every day, no boyfriend or nothing, and my own siblings were hanging around and... I got mad."

"I get it, Jan, I really do. We should have said something sooner."

"'Hey sis, so you know, we're all fucking?'" Jan laughed. "No, I get it. I just. I know you all think I'm a robot or something. I have feelings, too."

"Of course you do," I said.

"I'm terrible," Jan said.

"You're amazing."

"This is why I'm alone," Jan said. She sounded close to sobbing. "It's why Jake left me."

Jake was the fiance from before. The dude she'd been engaged to, then mysteriously split off with right before moving back home.

"He was like, perfect," Jan said, "His hair, his body. Good family. Whole package. Then I got the call about Dad losing his job and you all having to come back from school. I guess you were on my mind."

I honestly couldn't tell where this was leading. I was almost certain she was awake, but her words had the ramble of someone talking in their sleep.

"After the call, Jake and I. We did, you know. We made love. And I said it. I don't know why I did, but the words came out."

"The whole 'naughty' thing?" I asked.

"The whole naughty brother thing," Jan replied.

"Oh fuck," I said.

"Exactly," Jan said, "Jake froze. He couldn't even look me in the eye. He asked me for his ring back and everything. It was bad."

"I'm sorry Jan," I said, "I didn't know you, like, had those feelings."

"Neither did I," Jan said. She really did sob then. "I guess it was some weird subconscious thing. At the time, I mean. It was just a fantasy. I didn't actually want... Well, you know."

"Honestly Jan, it seems like he should have been a little more understanding. Like, if you're going to share your lives together, he ought to be able to handle a little kink. Right?"

"It was too much. I freaked him out. I freaked me out. So I came home. Not for this." Jan gestured at our naked bodies. "But because I was so broken. I didn't know what else to do."

"Do Mom and Dad...?"

"Are you kidding?!"

"Right," I said, "Of course not."

"And then I saw you and Lucy," Jan said, "I told myself it was nothing. A trick of my mind. But it kept happening. Catching you. And it made me so angry. And now here we are."

"You're punishing yourself," I said.

"Moving back home?" Jan said, "Yes. For sure. But this? I don't know what this is. It doesn't feel like punishment."

I hugged my oldest sister tighter. Kissed the back of her neck. I felt my dick, bless him, start to stiffen against her ass. But I knew this wasn't the time, so I pulled my groin back.

Jan sighed. She got out of bed. Her face was stained with tears.

"I'm going to go back to my room now," Jan said, "Thanks. For everything."

"Everything?" I asked, looking pointedly at my pointing penis.

"Oh heck yes," Jan said.

She kissed my forehead before slipping into the hallway.

*

"I had sex with Lucy," I said.

Lindsay looked up at me, surprised. We were both sitting at the kitchen table, eating lunch. My youngest sister was in her usual uniform of a bright pink, tummy-revealing tank top and tight yoga pants.

"Like, right now?" Lindsay asked. She looked so cute when she was confused. "Seriously?!"

"No, of course not," I said, "I've been home with you all day."

"OK good," Lindsay said, "I don't mind you doing it. I just want to make sure I'm there to see it."

I did not know how to respond to that. I took a deep breath and reset.

"No, what I meant was, Lucy and I had sex before. Like, before before. Back during the summer."

"Oh!" Lindsay said, "That's nice. Was it good? Ooo, was it bad? Is that why you stopped doing it? Are you, like, terrible in bed?"

"No! The sex was good. Really good. Like really really awesome good."

"I don't get why you're telling me any of this," Lindsay said, taking a bite of her yogurt.

"I'm trying to get there," I said.

"Well, go faster. We have class in an hour, and I need to get there early to set up."

"Lucy and I had sex back in the summer, and we made a mistake," I said, "I made a mistake."

I waited for my younger sister to interrupt, but she just stared back at me, intently. Her spoon rested on the edge of her bowl.

"We didn't use protection and... Well, you know."

"Lucy got pregnant!?"

"No, thank God."

"OK," Lindsay said, she went back to her breakfast. "And so your point is?"

"You asked me before why things were weird between Lucy and me," I said, "I thought you deserved to know. Especially because of what you've been saying. About us."

"Oh, don't worry about that," Lindsay said, "I know you think I'm some kind of space cadet, but I know what I'm doing. I won't get pregnant."

"OK," I said, "Good. But you still want to...?"

"Oh, for sure," Lindsay said, as casually as she was talking about a trip to the mall to buy underwear. "Have you talked to Lucy about this?"

"That I almost got her pregnant?" I asked, "Pretty sure she knows."

"No, I mean talked to her," Lindsay said, "Like for real."

I thought back. We'd definitely discussed things a few times. But had I truly talked it all out with my older sister in the way that Lindsay was asking?

"We need to head out," Lindsay said. My younger sister was flighty about everything, but not class. There, she was like some kind of mechanical engineer. Five minutes early was still ten minutes too late. "But thank you for telling me."

"Like I said, I thought you should know." I took her bowl from her and went to wash it in the sink.

"You've been giving me a lot of attention lately," Lindsay said, "Don't think I haven't noticed."

"Is that OK?" I asked from the kitchen.

"Yes, it very much is," Lindsay said.

*

"You told her?" Lucy asked when I got in the car.

It was late in the afternoon. Yoga was over and Lindsay was at home doing Lindsay-things (Vaping, napping, communicating with her inner-goddess. Something like that). My body ached like crazy from the class. If anything, I felt like the workouts were getting harder. Like my younger sister was intentionally upping the degree of difficulty every time I showed up.

"And?" Lucy pressed me. I always preferred her other form of pressing, personally. "Does she still want to do it?"

"More than ever," I said, "She even asked if she could do my 'moon chart' beforehand. Whatever that means."

"I don't think that has anything to do with your butt," Lucy said.

"Thank God for that," I said.

"It's too bad," Lucy said, "You have a nice butt."

She put her car into gear and drove off. We headed into town, her car rattling and rumbling as we went. The sun was low on the horizon, but still brighter at 5pm than it had been in months. I could see little green buds on some of the trees. The world was finally breaking out of its deep freeze.

"And Jan?" Lucy asked, "How are things with her?"

"Pretty good," I said, "We had a nice talk the other night. I think she's opening up for me, finally."

"In more ways than one?" Lucy asked, giving me an oversized wink. As hot as it was when she did it, I wished she'd pay more attention to the road.

"Seriously, Jan's really coming around."

"You're doing this on purpose," Lucy said, "I know you are."

"I mean, I thought she'd make it hard for me..."

"Enough," Lucy said, grabbing my hand while swerving to miss a lamppost, "Enough schtick."

"Seriously, I don't get how you're so cool about all this," I said, "Lindsay and Jan and all of it."

Lucy shrugged. "I don't know," she said, "We're family."

We pulled up to the strip mall and Lucy parked. Her old car sighed, like it was relieved it had survived the trip. I wasn't far off. My older sister was amazing at most things, but driving wasn't one of them.

"I still can't believe I let you talk me into this," Lucy said.

"I think it's important," I said, "You told me you wanted more, and this is where that starts."

"Indoor, glow-in-the-dark, sci-fi, mutant mini-golf," Lucy said, reading the sign above us. "You're such a romantic."

"Come on," I said, jumping out of the car. I hurried over to open Lucy's door for her. "I've got a two-for-one coupon for McDonald's for after, but it's only good if we get there before 4pm."

To my delight, my beautiful blonde sister laughed.

*

Cum.

I typed the word to Jan. Our chat stream looked like the script for someone's one-word challenge audio porn recording.

Come

Come

COME!

Cum?

Cum

CUM!

Cum cum cum

Cummity cum cummity

Cummy, cummy, two-by-four get your hot ass in my door

(OK, I may have made that last one up)

I heard the door slam and the sound of footsteps. It sounded like my usually aloof, older sister was racing down the hallway. So much for discretion.

She opened the door wearing something new: a black, silky kimono dappled with bright red flowers. It hung to barely below her sex and was open down to her navel in the middle. She was grinning wildly, until she noticed I wasn't alone.

"Oh," Jan said.

My oldest sister couldn't hide her disappointment as she saw me, Lindsay, and Lucy all sitting in my bedroom, fully clothed and playing cards on the floor. Lucy was wearing a sweater and jeans. Lindsay had on a t-shirt and her yoga pants. I was just chilling in my sweats and a tee. All very casual, normal sibling stuff. Sad, isn't it?

"Family game night?" Jan asked. She couldn't keep the disdain out of her voice. But to her credit, she was at least trying.

"Something like that," Lucy said, cheerfully. She patted the open space next to her on the floor.

Jan made another 'ate a sour grape' face, but she flopped down between Lindsay and me, folding her legs in a way that somehow managed to keep her pussy from being exposed in that kimono. She let out a long sigh.

Lindsay reached over to feel the material of her oldest sister's outfit. "Ooo, silky."

"I can't help but feel like I need to change," Jan said, eyeing the rest of our outfits.

"Personally, I love you just the way you are," I said.

Jan responded by sticking her tongue out at me.

"Don't worry," Lucy said, smiling so wide it threatened to swallow her face. "We aren't going to stay this way for long."

Lindsay gathered all the cards from the floor and made a tidy deck. Then she started shuffling the cards with the deft, expert demeanor of a seasoned dealer at the casino. Her dexterous fingers danced over the cards.

"You all aren't going to start humping the floor, are you?" Jan asked.

"Don't be lewd," Lindsay said, primly. She handed each of us a card. "Show down."

Lucy gave me a searching look. I shrugged back at my older sister. I didn't know what the skinny brunette was up to, either. We all turned over our cards. I was highest with a King. Lucy was lowest with a five.

Lindsay gestured at Lucy, making her meaning clear. My older sister grinned. She stood up and took off her sweater, revealing a tight, baby blue t-shirt. It clung to her massive chest in a way that was almost better than her being topless.

"This is either the worst game ever or the best," Jan said, looking at her sister, warily.

"Where are Mom and Dad?" I asked.

"Out," Lucy said, "Or downstairs watching TV. Or in their bedroom. I honestly don't give a fuck." The other girls nodded their agreement. I guess that question was answered.

Cards went around the room and clothes started flying off. It became immediately obvious that this wasn't a game at all, just Lindsay finding excuses for all of us to get mostly naked. Sometimes high card won, sometimes low did. Diamonds beat spades but only if a girl was holding the card? And one time Lucy had to take off her bra because, in Lindsay's words, 'the planets make it so.'

It was utter nonsense but who cared as I was quickly surrounded by beautiful, bare sister-flesh. Finally, the girls were all down to their panties and me to my boxers. I couldn't help but revel in the differences between Lucy's massive, swelling breasts, Jan's full, pointed tits, and Lindsay's cute, perky boobs. Lindsay's tiny, lithe body, Jan's sharp, lanky build, and Lucy's plunging curves.