On the Road to Somewhere

Kylie apparently didn't agree with my decision to pause for the occasion and made a small whining noise like a child who wasn't getting what they wanted. She took it upon herself to move on my cock as best she could and I took longer than necessary to rejoin her. There was something primally satisfying about watching my sister, or any girl really, craving release so badly. Not that I would, but if I started fucking her for real then I suspected she wouldn't have made a single complaint. I would definitely catch hell for it afterward though, when she was thinking more clearly.

"Fucking hell," Kylie moaned.

With her facing away from me I couldn't see her face to gauge her reaction, but there were enough other hints there to give me a good idea how she was feeling. Especially once she stuck a hand between her legs and started fingering herself while I continued fucking her from behind. I wondered how close she was and, perhaps more importantly, whether I'd be able to hold out long enough. I was in a situation where I didn't want to cum right away, but was too turned on to do much about it.

"Hey Jase," Kylie said, her words coming about as unevenly as her breathing.

"Yeah?"

"When you're ready, don't pull out okay?"

She wanted me to cum in her ass? That was fine with me, though the thought didn't do anything to help me last longer. Already that feeling was creeping up on me that told me my orgasm was going to hit soon. It wasn't what I wanted, but how the hell was I supposed to resist something so hot?

A few more strokes and I was there, too far gone for anything to stop me. I shot my semen deep inside my sister while she hissed in pleasure at the sensation it produced. As I had feared I did end up cumming before her, but not by much as she followed me by only seconds. Afterward, as though it was synchronized somehow, we collapsed together on the mattress. I had to fall to the side a bit to avoid landing on her and she immediately closed up the small gap that left between us.

"You came in my butt," Kylie said, as if it was the first I was hearing of it.

"You told me to."

"I know, it's just so... I don't even know if I can think of the right word. It somehow doesn't feel real even though I know it is." She looked at me seriously. "We just had sex."

"Does that bother you?"

"It should, but it doesn't. You know what I'm actually thinking?"

"No, I barely know what I'm thinking right now."

"I was worried it wouldn't be as good as I hoped when I actually tried it," she said, ignoring my attempt at humour. "Like real anal not just with toys or whatever. Now I know I like it. And even though it's weird, I'm kinda glad I got to try it with you for my first time. The guy I had regular sex with the first time, we don't even talk any more. Feels like I messed up when I think about it sometimes."

I pulled Kylie to me, letting her nestle in my arms and know that I was feeling as okay with everything as she was.

"I almost wish this could have been my first time with anal too," I said. "Would have been nice in a fucked up kind of way. It was still a first for me in one way though."

"Wha- oh, because I'm your sister." She giggled softly, then had to stifled a yawn partway through.

"Yeah. If anything that's going to make it more memorable than if you were just the first girl who let me stick it in her butt."

"Mmm, that's a nice thought. Your wording leaves a little to be desired though."

"It often does."

Kylie was showing signs of being tired, and I knew I was getting there too. As our conversation faded away I noticed at some point that she had fallen asleep. Within another few minutes so had I.

****

Despite the night I'd had, I woke up earlier than I'd managed the whole trip so far. Kylie wasn't right beside me which left me disappointed until I located her sitting on the end of the bed. She was still completely naked and was watching the sun come up looking fully content with the world. She smiled as she saw my eyes were open, but didn't say anything. For a couple minutes I lay where I was and stared, hypnotized in my semi-awake state by the beauty of my naked sister who was sitting at just the perfect angle in the early morning light.

Then she broke the spell by stretching, an interesting process all on its own, and turned to sit cross-legged facing me. It didn't have quite the same effect, but the view of her exposed pussy along with her breasts made for a decent consolation prize.

"Morning sleepy," she greeted me.

"Don't give me that, any other day you'd still be asleep too," I said.

The clock beside the bed said it wasn't even seven yet, hardly a fair time of day to be getting teased about sleeping in.

"I didn't seem to need as much sleep last night," she said. "I remember being so tired, then I woke up and I just didn't feel like staying where I was. I would have gone to find something to do except... I didn't really want to leave."

"Were you watching me?"

"Some, you and the sun. You looked so peaceful, I don't think I've ever seen you like that. Like a big baby. And I mean that in a good way."

She took my hand and squeezed gently, as though urging me not to be upset at the baby comparison.

"Well, whatever. I've been called worse I suppose."

With Kylie naked right in front of me I was naturally getting an erection, though it was hidden beneath the sheet that half-covered me. I didn't even remember pulling it over me, maybe I'd done it in my sleep.

"We should do something today," Kylie announced suddenly.

"Uh, like what?" I asked, having trouble switching gears so quickly.

"I don't know, just something together. Unless... if you think we need space...."

"No, that sounds good," I said, picking up on the obvious signals that my sister would be hurt if I tried to get away from her. As if I even wanted to. Whatever might have changed between us last night, I didn't even consider spending the day apart to be a real option.

"Great. There must be touristy shit around so I guess we could go check it out until we figure out something else. Or if you have any ideas."

"I'm barely awake right now, I'm hardly capable of planning a day out."

"Okay, well I'm gonna head back to my room. I don't think we'll be bothered, but if we were it'd be better if we had clothes on."

She stood up and started to walk away, drawing my eyes straight to her swaying ass. The ass I'd fucked the night before. If I used to think my little sister could drive me crazy when we were younger, that was nothing compared to now. Though the context was quite a bit different.

Once Kylie left I had to make the decision on whether or not to jerk off before getting up. I was already semi-hard, and I had plenty of masturbation fodder in my mind. It just didn't seem nearly so appealing when there was someone so close by who could do the job for me.

I lay there indecisively, not quite awake and unable to muster the will to actually do anything. Gradually my erection faded and the sound of our parents leaving from the next room finally pushed me to get up. I might as well get in a shower while I was pretty sure it was free. I did think of seeing if Kylie wanted to join me, but that would be pushing my luck. Especially when I didn't know how long mom and dad would be gone.

I did feel better after standing under the water for a few minutes. My dazed state was partly replaced by a growing alertness and energy that I would need for the day ahead. By the time I got out of the shower I was awake enough to start getting hungry. I'd wait for Kylie before going to get breakfast though, unless she took an obnoxiously long time.

When I returned to my room to get dressed I left the door open, so I knew when Kylie took her turn in the bathroom. After hearing the shower come on again it was only a moment or two before I realized how dumb it was to wait around for her and imagine her naked under the streaming water when I could just go watch. If she told me to leave then I would.

The shower had a glass door on it that fogged up with the hot water, meaning I couldn't see much through it. Kylie also couldn't see and had to slide the door open far enough to peek through at me when she heard me enter.

"Oh, it's you," she said. "What did you do, forget something?"

"No, just don't have anything better to do."

"So you decided to come perv on me?"

"Pretty much. Too bad I can't really see anything."

"You've seen it all by now anyway, I don't know why you're so fascinated."

"Yes you do. If you'd thought of it you would have done the same to me."

"Well... okay maybe."

Unfortunately sitting on floor there only a couple feet away from my sister was hardly much better than staying in my room. We did get to talk a little I suppose, but mainly I was waiting for the moment when she had to get out. When she did she realized, as I had earlier, that there were no towels within reach unless you had the foresight to hang one up ahead of time.

"Could you get me a towel, or are you going to be a brat make me get it myself?" she asked.

She was already halfway exposed from where she stood with the shower door partly opened, but to get a towel she'd need to get all the way out. I considered not helping her, but decided to be nice. The possibility of sex was a powerful motivator to keep her happy.

"Thanks," she said, sounding a little surprised as I handed her a towel.

"No problem."

I hadn't even been thinking about it, but as Kylie dried herself off I got a pretty decent view since she didn't immediately wrap the towel around her body. For some reason I had assumed that's what she would do, but at this point modesty was no longer the same issue it used to be for us.

It took longer than it should have, but eventually I clued in that she was showing off for me. The desire she had for my attention manifested itself once again and I belatedly caught the glint in her eye as she dried herself off far more thoroughly than necessary. When she finished up and returned to her room wearing only her towel, I followed.

"You're just going to follow me around all day like a puppy aren't you?" Kylie said in tone that told me she didn't actually mind.

I shrugged noncommittally and sat down on her bed. She rolled her eyes theatrically and started getting dressed.

It turned out to be a very involved process, possibly for my benefit. Certainly the amount of time she spent brushing her hair in the mirror while her towel only just barely managed to cover her butt was longer than it needed to be. And when she slipped on a pair of panties to wear while she decided on her outfit for the day she may as well have announced that she was enjoying being the sole focus of my attention. I would have bet good money that she didn't usually parade around topless while figuring out what she wanted to wear.

Once the novelty wore off a little Kylie finally chose a light sundress and put it on without a bra. It meant she was actually dressed properly, but there was still something sexy about knowing she only had two pieces of clothing on.

"Ready to go?" she asked, adopting an innocent look like she hadn't just spent fifteen minutes making me horny.

"Yeah. Breakfast first, then go see what there is?"

"Sounds good."

The bulge in my shorts faded away as we walked and by the time we reached the dining area of the building I had calmed down fully. There was a buffet style of service set up pretty much all day in a room on the bottom floor, no doubt to deal with guests operating on whatever schedules they felt like. Kylie teased me about how much food I got, but I think she was as hungry as I was and ate more than she normally would have too.

After that we were off to explore the local area, which turned out to mostly mean shopping. Not shopping in the 'enter a store and buy something' sense, but more in the 'wander around and look at absolutely everything' kind of way. Most of the shops nearby were clearly designed for vacationers and sold the sort of things you wouldn't look twice at normally but make a good memento.

Any other time I would have gotten bored quickly and tried to get out of it. This time though, I had Kylie to hold my attention. While she looked through displays of trinkets and jewelry, I looked at her. When I got the chance I would let my hand rest on her butt or wrap an arm around her waist, attaining discreet contact with her as much as possible. She fought me off when I did, swatting at me playfully or trying to give me a glare, but not once did I get the impression she wanted me to stop.

At one point she had picked out a necklace and was holding it up to her throat so she could examine the look in a nearby mirror. When she asked my opinion I stood directly behind her and rested my chin on her shoulder while I pretended to examine her reflection critically.

"Very nice," I said.

"The necklace, or my boobs?"

"Both. I wasn't really looking at the necklace though."

Kylie sighed and grabbed my wrists before my arms could completely encircle her.

"You're going to get us in trouble if you keep this up you know," she said.

"No one knows who we are," I said. "We can do whatever we want here."

"Yeah, but I might get used to it. And what exactly is it that we want to do?"

I shrugged. "I want to be close to you, that's about as far as my thoughts get right now."

"Well I appreciate the sentiment, just try to keep it casual okay?"

"Okay."

****

A few hours later and we'd bought a grand total of one thing. Or two things, however you want to count a pair of earrings. I ended up paying for them since Kylie didn't bring any money with her and I realized she'd either expected not to buy anything or she'd planned on me paying right from the beginning. Either way it annoyed me slightly, but the earrings really did look good on her.

We stopped at an outdoor cafe sometime in the early afternoon for something resembling lunch. My internal schedule was so messed up the normal order of things didn't seem all that important.

"You're staring at me again," Kylie said, sipping on her iced coffee. "People are going to get the wrong idea."

"You don't think they haven't been already?" I said. "Anyone who's paid any attention at all will think we're a couple. It's not just me, the way you act isn't like I'm your brother either. The way you drag me around between shops is much more like a girlfriend than a sister."

"Jase, what are we going to do? Mom and dad might be slow, but even they're going to pick up on something eventually." She studied the tabletop intently as she continued, avoiding my gaze entirely. "It was... I never intended for things to get nearly this far. I never even thought they could."

"But they did," I said softly.

"Yeah, guess that's what happens when you try to fix something that's not broken. Even if it doesn't break it still changes."

"On the bright side, we are closer than we ever were before. That's what you wanted right?"

"Yeah, but... this might actually be too close. I've been feeling things I really shouldn't be feeling about you. I guess that's probably obvious after what we did last night."

"That doesn't have to be a bad thing though, especially if we're both feeling the same way."

She looked up at me then, staring intently at me as though she was trying to see inside my brain.

"But how long is it going to last?"

"What do you mean?"

"You know what I mean Jase. Once we get home and things go back to normal, how long will it be before something changes again?"

"Maybe we shouldn't worry about that yet. We have time, we can figure things out."

"Yeah, I guess."

She clearly didn't buy it, but I wasn't sure what she wanted to hear.

It wasn't until later after we left the cafe and were heading back that she brought the subject up again. She'd been quiet for a while and the sudden leap back into our discussion left me a little confused for a moment.

"Walking around like this, it's going to be different when people know us," she said.

"Um, okay?"

"Seriously, are you really going to want to be seen hanging out with your little sister all the time? And that's not even counting how careful we're going to have to be not to do anything that gives us away. Plus-"

"Kylie," I interrupted, "are you trying to convince me that things have to back to normal, or are you just hoping I have an easy solution?"

"... more the second one," she said quietly.

"Then I can't help you. There are going to be problems no matter what we do at this point. But at least we can deal with them together, right?"

"I guess that's true." She took my hand and squeezed it. "I'll always have my brother to back me up."

"Damn straight. So don't even worry about anything, we can take care of it when it comes up."

Kylie seemed okay with that, and her mood generally improved to the point where she actually started humming tunes that I either couldn't recognize or she just made up. She didn't let go of my hand either, whether on purpose or because she just didn't think about it. All I knew was I was intensely aware of us holding hands and how I had absolutely no problem with it. She had a point when she mentioned how I'd feel acting this way around people we knew, but when we were anonymous it just felt nice to be able to display affection so casually.

"So are we gonna be, like, together now?" Kylie asked me.

"I think so, yes," I said.

"What does that make me then? Girlfriend doesn't sound quite right in this case."

"Maybe not. I don't know, I never really thought about it. You're still my sister to me."

"Yeah, but I'm kind of more than that now though. Right?"

"Depends on how you look at it. You're definitely more to me than the average sister would be to her brother, on the other hand you're the only girl who's ever going to be my sister. It's a unique position for you and it means more to me than a 'girlfriend' would at this point."

"Hm, I guess I can accept it when you put it that way. Just as long as you don't go thinking you can have a girlfriend on the side too," she teased.

"Don't worry, I don't have a death wish. I know better than to piss you off that badly."

"And here I thought you never learned."

She leaned in to kiss me on the cheek, a sweet and fairly innocent gesture. It made me realize that with everything we'd done, I had yet to kiss my sister properly. The time wasn't right for it, but as soon as the thought was in my mind I knew I would have to fix that in the near future.

****

If anything there was more anticipation leading up to that night than any of the others. Our relationship had officially changed now, and unlike previous nights I could be fairly confident about what was going to happen. There was next to no chance Kylie was going to decide she wanted to spend it alone, or tell me that we'd been pushing too far. This time I was going in practically knowing that I'd be having sex with my sister again.

The sheer amount of waiting I had to do that evening and into the night was torturous. We had to make sure our parents were asleep though, and that was the only thing that kept me just barely in my room once I was supposed to be going to bed. I wanted to go to my sister through our secret balcony route, but instead alternated pacing restlessly and fidgeting with any loose object I came across. If I had to imagine the perfect hell it would have been those long minutes stretched out to eternity.

Kylie snuck up on me while I had my back turned and I only coincidentally caught her walking toward me before she reached me. I was at first elated to see her, then confused what she was doing. It couldn't be time yet.

"You look like you're waiting for someone," she said.

She was wearing a slightly too-long t-shirt with no other clothing visible, though her underwear status was indeterminate. It made me want to grab her and find out exactly what was underneath.