Pressing Matters with Sister Pt. 04 - Spring Break

For their parts, the girls kept glancing at the growing tent beneath my boxers, like they were anxiously waiting for the real game to begin. Lord knows, I felt hard enough to start smacking baseballs. And I was confident I was about to hit at least a double, if not touch all the bases.

I assumed the next round would end with us removing our remaining piece of clothing, but instead, Lindsay declared that it was time for a new game. She drew two cards and held them up: a six of spades and a ten of hearts. She gestured to me and Lucy.

"Kiss," Lindsay said.

I looked over at my curvy, blonde sister. We'd touched each other in almost every way. But, somehow, this felt particularly intimate. It meant more than getting each other off. That was fun but oddly transactional. This was an expression of true affection for no other purpose. It was incest on a whole new level.

Lucy seemed to feel it too. She eyed our sister.

"The cards say it has to happen," Lindsay said with a shrug.

"You're making this up as you go along," Lucy said.

Lindsay gave all of us a wolfish smirk. "If that's what you want to believe."

"Fine," Lucy said.

She leaned across the circle, epic breasts dangling, and gave me a quick smack on the lips. Already aroused, I felt myself warm from my toes to my hair. Lucy sat back, smiling.

Lindsay drew two more cards out of the deck. To be honest, I don't remember what they were. Did it matter, truly?

"Kiss," Lindsay said, pointing at myself and Jan.

My oldest sister didn't look happy about it, but she leaned over and gave me a peck on the lips.

"This better be going somewhere, shrimp," Jan said to Lindsay.

"Just relax, crab," Lindsay replied.

Two more cards. This time Lindsay pointed to herself and me. When I leaned over to kiss her, she grabbed the back of my head. It was less of a kiss and more of her sucking the breath out of me. Wet, smacking passionate.

"Wow," Lucy said as we finally broke.

"See, that's a kiss," Lindsay said. Clearly our youngest, least experienced sister had decided she needed to teach all of us a lesson.

"I see that," Jan said. She layered the words with distaste, but the expression on her face was of far more interest.

"Now," Lindsay said, pointing back at Lucy and me. "KISS."

My older sister, still grinning silly from our last little peck, crawled over and pressed her lips to mine. We shared a gasp as we fully connected. I couldn't help myself. I reached for Lucy's ample boob and hefted it in my hand.

My sister must have been feeling similarly, because she reached into my boxers and fished out my cock. She began slowly stroking it. Our tongues entwined. Finally, we came apart, gasping for air. I don't think we really intended to stop, but then our little sister cleared her throat.

"The cards didn't say to do that," Lindsay said, looking pointedly at where Lucy's hand was still clutching my cock. At my fingers on her tits.

"Fuck your cards," Lucy said, she leaned forward and gave me another kiss.

"Oh no," Lindsay said, "That's the whole point. The cards fuck you."

"Can we please go back to the game," Jan said. She was rubbing her legs together in a most telling way.

"Yes," Lindsay said, pulling out two more cards. She didn't even bother showing us. She just looked and cooed.

"Kiss," she said, gesturing at Jan and me.

My oldest sister looked nervous for a moment. If Lucy and I were awkward at first, Jan and I were far worse. We'd barely touched each other so far.

"No," Lindsay said. She made her meaning clear. My cock was sticking, bare, out of my boxers and Lindsay pointed right at it. "Kiss."

Jan's eyes threatened to pop out of her head. I had the sense this was the break point. Would she do it? If she took this step, actual oral with her younger brother, then we truly would be on our way to something spectacular. And if she didn't, this whole thing was going to blow up in our faces.

But, as I awaited my fate, I remembered my promise to myself. I was letting things happen again. After all, Lindsay was steering all of this. And I was sitting back allowing Jan to make her choice. That wouldn't do. Not at all.

I put my hand on the side of Jan's head. Let my fingers run through her oil-dark hair. I realized she had it down again. It was so silky and cool to the touch. I thumbed her cheek. Met those bright blue eyes with mine.

"Come on sis," I said, "Suck my cock."

Gently, I steered Jan down till her lips touched my dick. And with an eager purr, my oldest sister swallowed my member.

"Oh fuck," I said, as I was surrounded by the warm wet of her mouth. Damn she felt so good. Her tongue slurping and licking all around my shaft.

"Such a naughty sister," Lucy said, "Blowing your baby brother like that."

Jan squeaked. The top of her chest and her cheeks went pink.

"Only a nasty slut would suck off her sibling," Lindsay said, "A needy, broken thing."

"That's your little brother," Lucy said, "You can't make him feel like that."

"Oh God," Jan popped her head off my dick. Her eyes rolled back in her head.

"Did you just cum from that you sister slut?" Lindsay asked.

Jan's hand shot up and she squeezed her nipple. Her whole body seemed to cinch. Her breath sucked in raw. "Fuh... fuck me."

Our oldest sister fell on the floor, panting.

"Well, that was fun," Lucy said, "Didn't even need to touch you for that."

"Yuh," Jan said, still gasping for air. "Uh huh."

Lindsay sat to the side, looking pouty. "I want to cum too," she whined.

"So, rub yourself off, you little goof," Lucy said.

"I want Dylan to do it," Lindsay said.

"Do you want to do it?" Lucy asked, "Or do it?"

"Ooooh, I want to see that," Jan said. Apparently, she was conscious enough to get our sister's meaning.

Lindsay froze, thinking about it. She grabbed her phone from the side and tapped a few buttons. "Not yet," she said, frowning slightly, "The celestials are not fully aligned."

"She means she might be ovulating," Lucy said.

Lindsay glared at her older sister.

"Bad little sister," Jan said. She was mumbling, like off in her own little dream world. "Giving her brother a little baby."

"Jeez, we broke her brain," Lucy said.

"I know, right?" Lindsay said, "Wait till Dylan fucks her."

"Ohhhhhh fuck yeah," Jan murmured.

On the one hand, I wasn't thrilled that my sisters were already making decisions about what I was going to be doing with my dick. On the other, I mean, OK I was absolutely ecstatic.

"Dylan can still get me off though," Lindsay said, pulling us back to the pussy at hand.

"Sure thing," I said, "Fingers?" I asked, waggling my digits. "Or tongue."

"Tongue please!" Lindsay practically shouted it. She ripped off her panties, shoved her supple legs apart and flopped back on her elbows.

I buried myself in my little sister's wanting snatch. Her taste was almost floral. Full and womanly. I lapped at her juices before settling into her most intimate place. Pressing with my tongue while I pushed with my fingers.

Behind me, I felt something wonderful engulf my cock and knew it was Lucy, sucking me off. It was different than what Jan had done to me before, more loving, but no less lovely. Difficult too, as I was pulled between the two poles of giving and receiving.

None of us were going to last long like this. Lindsay wrapped her legs around my neck. She squeaked, then giggled as her orgasm overtook her. Her pleasure gave me the last little push I needed. My cock swelled in Lucy's mouth, and I peaked, shooting my warmth onto her tongue. Behind me, I heard my older sister grunt as I emptied, her own finger-supplied orgasm mixing with those of her siblings.

All four of us collapsed on the floor, spent. Covered in each other's juices and not even caring. Each of my sisters kissed me in turn. We drifted off to sleep there, entangled.

Like it was nothing at all.

*

"It's time," Lindsay said, a few days later. "I can feel it."

We'd stopped pretending at propriety. With a week off and nothing to do except each other, we'd been doing exactly that. Jan had even taken the rest of the week off from work (apparently, she had a hoard of PTO, saved up from working herself to death for the last few years). Lindsay's game may have been ridiculous, but it accomplished what it was supposed to -- we were off to the races.

The four of us rubbed, licked, and sucked every chance we got. Lucy and Lindsay got to see Jan's dildo in all of its violet glory. They all tried humping my bedpost. Jan even did the press thing once -- though she stopped after about a minute, said it was dumb, and got her toy instead.

More importantly, though, we all did it together. Moreover, our connections felt casual, like we were binging a show on Netflix or taking on a baking project. As if this was something totally normal for families to do together. Most importantly, though, we didn't do the other thing. You know, the big finale.

We talked about it a lot. Usually when we were covering each other with our cums. But actual penetration, good ol' d-in-p, never came to pass. Which was fine, really. I was beginning to become comfortable with the fact that it was something my sisters wanted to talk about, rather than do.

Especially with the whole 'no birth control' thing, that was probably a good idea. Actually, when I thought about it that way, our insistence on keeping things mostly masturbatory was probably for the best.

Then, one afternoon, I was in the kitchen making dinner when Lindsay scampered over to me, grabbed my hand, and said the magic words.

"It's time."

"Now?" I asked.

"Now now," Lindsay said. I looked around the house. Our parents were both working. Jan and Lucy, oddly, were nowhere to be seen. It was just me and my little sister in the kitchen.

"Can I at least finish boiling the pasta?" I asked, "I don't want to ruin dinner."

Lindsay actually looked at her watch. "Two minutes," she said. Then she bolted off, long brown hair flowing behind her like a mane.

I looked at the boiling pot of water. Would two minutes even be enough to... Oh who was I kidding?

"Fuck it," I said to no one in particular, and switched off the burner.

I hurried back to my little sister's bedroom.

I quickly discovered where Lucy and Jan were -- they were waiting for me in Lindsay's room. My little sister lay back on the bed, fully clothed. Our older sisters stood on either side of her. There was something almost religious about the scene.

Part of that came from Lindsay's own adornments. She'd lit candles on either side of the bed and covered the sheets in pink and purple petals. There was a strong scent of lavender in the air, coming from a nearby puffing purifier. Light dulcimer music played. Were we about to have horrible, dirty incest here or raise the dead? I almost laughed, trying to figure out which would be the less transgressive against the laws of nature.

"Took you long enough," Jan said as I entered the bedroom. I gave my oldest sister a glare.

"We, um..." Lucy started, then fumbled. There was something adorable about her discomfort. She was usually so easy and confident about this kind of stuff. "That is."

"I asked my sisters to be here to assist in the ritual," Lindsay said.

Ritual.

"You have to admit, it sounds better than incest orgy," Jan said with a wry smile.

Orgy!?

"Just you and me," Lindsay said, "I promise. We have to align, in body and mind. Our connection. I feel it pulling at me."

"She means she's horny as fuck," Jan said. Apparently, she'd taken on the role of translator for the day's event.

"OK, I think we've got this," I said, looking my sisters off. This was weird enough as is without having a sold-out crowd.

"No," Lindsay said quickly. "I want them to stay. For the, um, connection. It'll help strengthen the bond."

I didn't need my oldest sister to decipher that one. Lindsay wanted to be seen as in control, but she was nervous about this. Having Lucy and Jan there, as odd as it might have seemed, was helping her stay comfortable. I wasn't going to argue with her about that.

"No problem," I said.

My sister nodded. She was still fully clothed, lying back on the bed with her arms and legs so stiff she might have been chained there. I sat on the bed, gingerly, and stroked my baby sister's long brown hair. She cooed.

"I know how important this is to you," I said.

"To us," Lindsay corrected me. "Everything we've planned. None of it can happen unless we do this. We have to forge that bond."

"OK," I said, "I get that. Do you want to show me the way? Or do you want us to do this together?"

"Together," Lindsay said with a squeak. "All of us."

I nodded, continuing to pet my sister's head. Like she was a frightened foal in a lightning storm.

Jan sat down on the other side of the bed. She reached for Lindsay's shirt and took it off, exposing another one of my sister's tight sports bras -- an aqua one. As if they'd practiced this all before, Lucy sat next to me and pulled down Lindsay's yoga pants, revealing a matching pair of panties.

Lindsay was gasping for air, breathing hard like we were in the middle of a difficult exercise routine. I reached for my own clothes, but my sisters stopped me. Jan took off my shirt while Lucy loosed my jeans. I wondered how they'd decided who should do what.

Now Lindsay and I were down to our underwear. I felt the moment was right, so I leaned down and kissed Lindsay on the lips. She wrapped her arms around me. The awkwardness of making out with my little sister was still there. It only made things feel all the more electric.

"Prepare him," Lindsay said, "Us."

Jan reached into my boxers and found my cock. She squeezed it, finding me already plenty hard. To my surprise, Lucy reached into Lindsay's panties and started rubbing her pussy.

"Jeez, he's already about to explode," Jan said.

"Same here," Lucy said, "It's almost like our younger siblings really want to fuck each other."

"Nasty, naughty little brother and sister," Jan said.

"We're ready?" Lindsay asked.

"Any more ready and he's going to end before we can begin," Jan said.

Lucy shushed her. Lindsay giggled.

I kept kissing my little sister. Her ears, her cheeks, her neck. Jan removed Lindsay's bra and I moved my lips down to her adorable titties. Suckling at her eager nubs. I barely even noticed as Lucy took off my boxers. As she slipped off Lindsay's bottoms. Only when my cock brushed Lindsay's heat did I realize we were both completely bare.

"Are you sure, Linds?" I asked. Losing your virginity to your brother, there was no going back from that.

"Oh yes," Lindsay said, "I want to feel your essence inside me."

Inside. Yeah, about that.

"We can do that," I said, "We will do that. But maybe it makes sense to get a condom. Or at least not finish inside you. You know, with your birth control and everything."

"No," Lindsay said forcefully. "I promise. It'll be OK. Perfect."

I looked over at Lucy. My older sister shrugged. Like impregnating our younger sister was just one of those things that happened on occasion and there was nothing to be done about it.

In that moment, the pie chart that was my brain divided thusly. 3% believed my sister when she said there was nothing to worry about, that she was an adult and knew her own body and was totally trustworthy. Another 29% said that relying on Lindsay was crazy -- this was the same girl who'd once told me that daffodils were friendly, but sunflowers were mean -- she was going to get knocked up for sure and I needed to stay far, far away.

The problem was, the other 68% of my mind which didn't care about either side and was chanting fuck that sis as loud as it could.

So, you can figure out how everything went down.

Lucy grabbed my dick, giving me a flirty smirk as she felt my hardness fill her hand. She aimed me at our little sister's center. And just like that, my cockhead kissed at the entrance of Lindsay's tiny quim.

"Ready, Linds?" I asked.

The cute brunette nodded, vigorously. I slid forward. I felt a mix of conflicting sensations. The heat of Lindsay's pussy grabbing hold as the warmth of Lucy's hand fell away. I sank into my sister, bare. Everything went blank.

All I could feel were the wondrous sensations as Lindsay's lovely cunt slipped around me. Wet and wanting. Tighter than anything I'd ever felt. Hotter too. Like sliding into a gasping, groaning volcano.

Lindsay huffed as I filled her. Her expression equal parts fear and desire. She watched my every movement. Searching. For what I cannot say. Her body beneath me rising and falling rhythmic. Her breaths coming deep and desperate.

"Ssssssooooo deep," Lindsay groaned.

"You've got this," Lucy said. She gave me an inquisitive look.

"Almost all," I said.

I slipped in the last inch. My balls bounced against my sister's bottom. Both of us sighed -- a sound that spoke of relief, delight, and concern all at once. We'd done it, completely. I was buried to the end in my baby sister. Her pussy was fully filled with my cock. Everything that entailed, it held us enraptured for a moment.

"Well don't just lie there," Jan snapped, peevish, "Fuck her for fuck's sake."

"Jan, you can go now," I said.

"No, it's OK," Lindsay said, "She can stay."

But my oldest sister got the message. She nodded her head, biting her lip, clearly chastened.

Slowly, I slid back in Lindsay, then drove forward. She hissed like she was scalded. Like I was the source of that molten heat, instead of her. For a moment, I thought I'd hurt her.

"Just. Getting used," Lindsay said.

I knew what she meant. My sister's clasping, steaming eighteen-year-old pussy was something new to be sure. With every breath, I worried I was about to break loose. And while she'd already told me it was safe to cum, I knew I needed to make Lindsay's first time more special than a pump and dump.

Lindsay, on her side, wasn't helping things. She was figuring out her body, shifting and squeezing to see what felt the best. How she could eke out her own pleasure.

"Mmmm... that's nice," Lindsay said. She was off in her own universe.

Unable to hold back my urges any longer, I started to slide back and forth in my sister. Lindsay groaned as I moved. At first, I thought it might be pain, but I saw from the look in her eyes that it was all pleasure.

"That looks so nice," Lucy said, absently in my ear. I didn't need to look to know her fingers were in her own snatch.

"It's so bad," Jan said, openly strumming herself, as well.

"It's so gooood," Lindsay sighed, "Such a good brother. Making me feel so... AH!"

I'd reached down and found Lindsay's clit. I knew I didn't have long, and I needed to get her off. I'd worked my little sister enough times to have a pretty good idea of rhythm and pace. Her tiny, well-muscled body bucked as I rubbed her. Her pussy, impossibly, tightened. To the point where I was sure she was about to rip my cock right off.

Lindsays squeaked. She squealed. A throaty chuckle escaped her lips, and she went over the top. Body straining.

"Oh... Goddess..." The words slipped out of her mouth unbidden. Like the hiss from a tea kettle. All the pressure pushing them loose.

Finally, Lindsay fell back to the bed.

"Cum," she told me, with a firmness of voice I'd never heard from her. Like she was channeling Jan. "Cum in me!"

I looked over at Lucy. My older sister gave me a funny little smirk.

"You heard the girl," Jan said on my other side, sharply.

"Nuh-need you to cum. So deep!" Lindsay said.

"It's not a... I can't just flip a switch," I said.

All three of my sisters gave me a doubting look.

Honestly, I don't know what I was arguing. I'd been close before we started so how near was I now? I guess I wanted to prolong that feeling of being inside my little sister. Feeling her body surround me.