Pressing Matters with Sister

Lucy didn't say a word. She reached back and unsnapped her black, lacy lingerie. She pulled it away and finally, her bare breasts hung free. They were better than I'd been picturing. Plump with phenomenally pert, pink nipples. I lost track of time. Of myself. My whole universe shattered by such a simple moment.

"Your turn," Lucy said. I noticed she'd stopped humping the pillow completely. She was waiting for me to get set.

I stood up and shimmied my shorts and underwear down in one go. My dick popped up, sticking straight out, like an overwound jack-in-the-box. I grabbed it immediately. Unable to control my urge to stroke myself.

Now, it was Lucy's turn to gasp. She stared up at my dick like it was an obelisk. A great and powerful object of desire.

"Wow," Lucy said. It seemed she wanted to add to that sentiment, but her brain was no longer in the business of making words.

I sat down on the couch. My bare bottom stuck to the canvas. Lucy spun herself on the ground so she could tilt her head up and see.

"You like it?" I asked, repeating what Lucy had said before. "Is my cock really so amazing, big sis?"

"Stroke it," Lucy said, "Show me. I need to see."

Like I required a command by that point. My instincts had already kicked in. I gripped my dick and worked the loose skin back and forth. I was only using my hand, and dry at that, but it didn't matter. It felt incredible.

Meanwhile, below me, Lucy began trembling as she took herself to town on the pillow.

"Oh, Dylan," she said, "Feels so good. Your cock. So thick. Oh, I want it. Show me."

With everything that had already happened, with all that we were doing, I wasn't going to last long. Fortunately, neither was Lucy.

My older sister rolled up on her groin, pointed her massive tits to the sky, then stiffened. Froze in place. Eyes glazed over. Mouth open. Finally, she broke. She let out a short, sharp sob as the pleasure squeezed out of her.

At that same moment, my cock exploded in my hand. A huge gout of cum rocketed out and splattered on my sister's face. I cried out as my orgasm overwhelmed me.

Lucy rolled over onto her back. She jammed her hand into her shorts and buried it in her pussy, working it like she was trying to rip the poor thing off. She stared up at me, eyes filled with hunger despite having already reached her peak.

I hit her chest with my second shot of semen. Splattered her face again with my third. My sister gasped and groaned as I bathed her in my essence.

Finally, I puddled onto the ground, splayed out next to my sister. The last of my spend leaked out over my fingers. Lucy rolled over and kissed my forehead again. She stank of pussy and sperm. Desire and satisfaction. Brother and sister, in a way we're never supposed to experience.

"You got me," Lucy said, gasping for breath, "Got me good."

"Sorry," I said.

"No way, that was awesome," Lucy said. "Going to need a shower now though."

"Me too," I said.

Lucy didn't miss what I was implying. For a moment, my big sister stared at me. She had my cum in her hair. On her massive tits. Both of us were barely clothed. Was I really asking for that much more?

To my surprise, my older sister actually seemed to consider my offer. But then she jumped up and skipped away.

*

July rolled into August. The heatwave ended, and while it wasn't exactly comfortable, we left unbearable back in the rearview mirror. I thought, after everything that had happened, that we'd progress more. Maybe Lucy would repeat her performance and take her top off or ask me to show her my dick. But none of that happened. Instead, we went back to regular old pressing.

At least for a little while.

In the meantime, life didn't stop moving around us. With time to school getting closer, needs outside of masturbating with my sister began to take precedence. We drove to County a couple of times to make sure everything was set with the registrar and to get our supplies for the year.

Our little sister, Lindsay, was getting ready for her last year of high school, and we helped her get set up. Lindsay was going to join us at County after high school, so we took her with us to see the campus, too.

Lucy and I did our usual chores -- food shopping, laundry, cooking meals. My parents were still working like dogs, but our older sister, Jan, got a bit of a break midway through the month and we met her in the city for lunch. Jan made no mention of the previous 'incident' and certainly we had nothing to say about it.

In other words, we acted like perfectly normal siblings, enjoying our summer break as best we could, considering the circumstances. You'd never know we were slipping away for shared masturbation sessions every now and then.

Except we totally were.

"I want to try something different this time," Lucy announced when I came into her bedroom. It was a random Wednesday and she'd found me in the laundry room, folding clothes. She'd given me the chin jut and here we were, getting ready to get off under the watchful eye of Link and Tom Nook, eyeing us from Lucy's bedroom walls.

The fact that Lucy had spoken up at all already had me nervous. Sure, we talked dirty to each other during the act, but we never came out and discussed the mechanics of what we were up to. Not really.

I assumed Lucy meant that she wanted me to jerk off again. Which, I was totally up for. I was all prepared to let her know that I was fine with it (in exchange for a boob reveal, natch), when she swerved so hard it nearly knocked me over.

"I'm just thinking," Lucy said, "Instead of using the floor or a pillow or whatever, it might be nice to try it together."

I raised an eyebrow. Wasn't that what we'd been doing?

"No, I mean, like. If you were pressing on me. And I was pressing on you. It might feel even better, you know?"

I was too shocked to respond. What was Lucy suggesting, exactly?

"We'd wear our clothes," Lucy said, as if that made things better. "It would be the same as always. Sort of."

It was that sort of that really set it apart, wasn't it? I think some part of me was convinced, even after what we'd done during the movie, that this remained normal sibling behavior. That you could tell someone about it, and they wouldn't stare at you in horror. I mean, I wasn't going to proactively bring it up at parties or anything. But I thought it was something I could confess to if needed.

This, though -- what Lucy was suggesting -- was so close to actual sex with my sister, I didn't know how to respond. Would I, like, touch her? Would we kiss? Would she grab my butt while I pressed against her?

"Well, we'll have to touch," Lucy answered, "Definitely no kissing, though. And as to your butt, well, you do have a nice ass. But I'll try to restrain myself if you will."

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

"Pleeeeeease," Lucy said, "If we don't like it, we can stop. I promise it'll be awesome, and I bet it'll feel way better than doing it on the floor. And it won't be anything different than we're already doing. It's almost exactly the same thing. Truly."

"So, you would, like, lie down. And I would be on top of you. And we would sort of, um, align?"

"Exactly," Lucy said. She clapped her hands. Somehow, it seemed, I'd agreed to do this without realizing it.

My buxom, beautiful, blonde older sister climbed onto her bed and lay on her back. She patted the comforter, like asking a puppy to jump up and join her for a snuggle. Per usual, Lucy was wearing a t-shirt and tiny shorts. Yellow and green, respectively.

I had on a shirt, as well, and a pair of grey sweat-shorts. The thought of lying on my sister clearly appealed to one part of my anatomy, because I was already achingly erect. For once, my hard-on was going to be an advantage when we went to press.

I climbed onto the bed. It was oddly soft, like trying to crawl across a Bounce House with fifty kids going to town on it. I dragged myself next to my sister. Our faces so close, our noses could practically touch.

"Like this," I said.

"Whole body," Lucy said.

I climbed over my older sister. She spread her thick thighs. Holy fuck. This was oh-so-very-much like fucking. The clothes did not make a damned difference, I swear they didn't.

Lucy seemed to be rethinking her idea, as well. Like the sudden closeness finally brought it home to her about what she was about to do with her brother. She gave me a nervous smile as I adjusted myself. But she didn't stop me.

Gingerly, I aimed my groin over my sister's. Then I slowly lowered it down. My hardness pressed into her. I couldn't tell if I had the right spot or not.

"Little higher," Lucy said. "To the left."

Through layers of clothing, I couldn't truly tell whether I was pressing against a leg, a tummy, or a pussy. But my sister sure knew when I hit her cleft because she let out a long, satisfied sigh.

"There you go," Lucy said. She brushed her hair out of her eyes. "That's the spot."

My older sister looked up at me, expectantly. Again, we shared an anxious grin.

"OK?" I asked.

"Yes, OK," Lucy said.

I became very aware of her soft, warm body. Her breasts pressing into my chest. Her legs on either side of mine. The smell of her shampoo -- apple-y and sweet. Her full lips and cute little tongue. The endless blue-sky of her eyes. Not a cloud in sight for miles.

Lucy seemed to be examining me in the same way. Her eyes and body adjusting to mine. She put her hand up to touch my cheek, then ripped it away like it burned her.

"Sorry," she said, "Habit."

I didn't have a good sense of my sister's sexual experience. I knew she'd had boyfriends and I was sure they'd done more than kiss. I didn't bother asking because she was my big sister, and it was none of my business. She certainly never inquired about my (meager) dating history.

Now, though, intimately on top of each other, I wondered if this was something my sister had shared with someone else. We say 'virginity' like it's a singular thing and I suppose it can be. But there are all sorts of 'virginities' if you think about it -- an endless number of intimate acts we can experience for the first time. I couldn't help but wonder if my sister was sharing one of those with me in that very moment. The same way I was giving my own to her.

"You can press," Lucy said, "I'm ready."

I nodded. With my hardness firmly slotted against my sister, I ground down.

Lucy's eyes flashed. She giggled. Then groaned.

"That's. Definitely. The spot," she said.

"Uh huh," I agreed.

We pushed against each other for as long as we could, then broke. Gasping. Did it again. In some ways, this experience was almost expected. It's what I'd been picturing every time on the floor, after all. And yet it was so different than anything I could have imagined. Beyond my fantasies into something truly unimaginable. Wonderful in every way.

I pressed into my sister and her hands reached up and gripped my butt, pushing me down into her.

"Sorry," Lucy said, but she didn't stop.

I grabbed her shoulders for purchase, in response. For a moment, I thought about reaching lower. I was afraid that one wrong action would end things. I can't imagine how that would have happened. But in the moment, I swear it made sense.

Lucy's gasps and groans got faster. Our actions more frantic. We worked each other to our release. Unlike before, we didn't talk. Didn't need to. All the stimulation we required was right there, with our sibling.

"Close." I managed to squeak out.

"Do it," Lucy said, "Let it go."

A moment later, I felt the warm wetness of my spend spill into my shorts. There was something almost painful about it. Strained. The bliss overtook me. I felt my sister's hand on my head. Stroking my hair lovingly. I became very aware of sharing this intimate, vulnerable thing with my sister. It made everything more satisfying, yet also scarier.

When I got my strength back, I rolled off of Lucy.

"That was nice," she said, "Thank you for letting that happen."

"Did you...?"

"Not really," Lucy said.

"I'm sorry," I said, meaning it.

"No, don't be," Lucy said, "Honestly it was totally awesome. Different. I loved it."

I nodded, letting myself believe her. If I thought the floor was comfortable post-cum, you can only imagine how nice it felt to be in Lucy's soft warm bed. I let my head loll against the perfumed pillows.

Then Lucy said something that totally blew my mind.

"I think it would be better if we do it without pants next time," she said.

There wasn't a word in that sentence that didn't make my heart race.

*

Fortunately (or not, depending on your perspective), my big sister didn't mean naked, which is what I initially thought she intended.

"No, we need underwear, silly!" Lucy said, clearly trying not to laugh.

We were in my bedroom this time. Keeping things fresh, I guess. It was a few days after our previous encounter, and I'd spent the entire time on tenterhooks trying to figure out what Lucy had meant by 'without pants.' Obviously, I'd guessed wrong.

"That would be way too much like actual sex," Lucy explained, as if this were a totally logical way to draw the line. "Also, to be honest we've had to cut back on some necessities because of, well, everything. You know, medical things. So, I'm like, not safe. At the moment. Having at least a layer between me and any of your little swimmers is probably for the best."

"Wow, I'm sorry," I said, "That sucks."

In all that we'd been going through, basic needs like birth control had never occurred to me. I guess being a guy afforded me a few more luxuries than I'd realized. I wondered what else the family was going without in the moment. Things that had never occurred to me.

"It's whatever," Lucy said, "Honestly, it's not the end of the world. Not like I have a boyfriend or anything right now. And Mom thinks we'll be able to get insurance back in a few months, so I'll be good to go."

"OK," I said, "Still, is there's something I can do to help?"

"Well, you can start by taking your pants off so we can do this properly," Lucy said. I mean, if that wasn't the sexiest thing you've ever heard, what is?

I smirked at my sister and lowered my bottoms, careful to keep my boxers in place. Lucy shucked off her own shorts and hopped up onto my bed. She lay back, unable to keep from making a silly giggle.

"OK, same as last time," Lucy said.

I wish I could tell you that I was used to being in such close contact with my sister by then. But getting on top of her was the same disorienting experience all over again. I was dizzy like I'd climbed a mountain, rather than mounted my sexy older sibling.

I rested my hardness on Lucy's sex. Well, she was right about one thing, pressing with just underwear on was way different. The thin cloth seemed barely able to contain us. I swore I could feel the heat and dampness of my sister's pussy. I was certain she could feel the warmth of my hard-on. The fly of my boxers never felt so precarious.

I pressed and Lucy moaned. She wrapped her arms and legs around me, holding me close. I became very aware of how much we were bare skin to bare skin. Her legs on mine. I buried my head in the crook of her neck. Her scent overwhelmed me as I ground into her.

"Oh Dylan." Lucy humped up into me. I could tell the pleasure was taking hold of her this time. "So good."

Both of us were slick with sweat. My room was already hot, but now it felt like we were baking. My muscles ached. How was this so much work?

"Getting... close..." Lucy said.

I pressed down as hard as I could. Lucy made this strange, high pitched, strained noise. Then punctuated it with a gasp. The effort put me over the top as well. Both of us came hard, wrapped around each other.

When it was over, Lucy cackled and gave me a peck on the lips. I was so enraptured by my orgasm, by my sister's, I didn't even startle.

"Yup, better with just underwear," Lucy said. She pushed me off of her and I saw I'd left a pretty large wet spot on her panties. She had a few streaks down her legs, as well. The liquid was white, so I knew it wasn't only my sister's lubrication. "No further, though," Lucy said, "It would be way too dangerous."

I nodded my agreement. Both of us drifted off for a nap.

*

Despite everything going on with the family finances, there was one area that my parents swore we could not skimp on: my baby sister Lindsay's eighteenth birthday party.

We invited everyone we could think of to the house -- family, friends, neighbors -- whoever wanted to come plus quite a few people who probably didn't but showed up anyway. We rented a tent for the backyard, plus tables and chairs. We had catered food, a live band (some of Lindsay's high school friends who agreed to $3/hour, but still), the whole thing.

If there wasn't too much food, too many people, and too much noise there was an overabundance of one thing: alcohol. And that's what led to all the trouble.

I spent most of my time trying to enjoy myself. In some ways, it was nice, seeing all these people -- family and friends that I'd managed to avoid all summer suddenly felt welcome. At least mostly. Every conversation was twinged with the fear that someone was going to start interrogating me about what was going on with me or the family. It gave even the sweetest moments a sour twist.

About a couple of hours into it, I was walking back from the bathroom when I felt a hand on my shoulder. I turned and saw Lucy standing behind me, grinning from ear-to-ear. She was wearing a sleeveless, summery dress with a pink, floral pattern that showed off her curves. Lucy had a beer in her hand and, judging by the look in her eyes, quite a few more in her belly.

"Hey Dylan," she said, a bit too loudly, "There's someone who wants to say 'hi.'"

"OK?"

Lucy took my hand and led me out to the backyard. There had to be at least twenty people out there, impressive considering the size of our lawn. Lucy pulled me straight through the morass to the back, where a cute brunette was lying back in a recliner. She was wearing a tight, black top with blue jeans and sunglasses. Her dark hair hung past her shoulders.

"Dylan, you remember Kara, don't you?" Lucy said, then collapsed into giggles.

I did my best to say hello while also ignoring my sister. I did, indeed, remember Kara. Lying back in the sun, she was even cuter than my mind had given her credit for. The petite brunette extended her hand, and I gave it a little touch.

"Don't mind Lucy," Kara said, "She's had a few too many, I fear."

"What about you?"

"Oh, definitely don't ignore me," Kara said. She gave me a sly smile.

Lucy started laughing even harder.

"Jeez Lucy, take a breath," I said.

I sat on the end of the lounger and talked to Kara for a bit. She was back from school for a couple weeks, having spent most of the summer in Italy visiting an uncle. She had all sorts of stories about adventures on the Amalfi Coast, eating amazing food, and basically having the experience of a lifetime.

"What about you?" Kara asked, "How's your summer been?"

"Oh, just hanging out," I said, very aware of my sister's presence. I'm sure my cheeks flushed as I said it.

"Yeah, Lucy told me all about it," Kara said. My heart slowed. A rush filled my ears. My sister hadn't told Kara everything everything, had she? "She said you guys have been sitting around the house watching movies or whatever. Sounds miserable."

"Oh, yes," I said, relief flooding me. "That's exactly what's been happening."

"Well, I can't say it's exactly been bad for you," Kara said, eyeing me meaningfully, "You look good, Dylan. You filled out."

"Oh, um, thanks," I said, "You do too. Even cuter than I remembered."

"Cuter, huh?" Kara said.