On the Road to Somewhere

"Because underwear is meant to be hidden, you think it's wrong somehow even if isn't really a big deal."

"If it's not a big deal how come you're getting hard?" she asked softly.

"Fuck off," I growled even though she was right.

I'd been trying to hide it and hope it would go away, but I was definitely getting an erection. It wasn't even like she was naked, I shouldn't have that kind of reaction to her over a little skin. But it was so much more than just skin, it was the knowledge that I shouldn't be looking at my sister that way at all combined with the second-hand emotions I was getting from her. Nervousness, embarrassment, excitement, and all from being in a semi-public location without her outer layer of clothing. I was curious if either of us would be able to handle it if she stripped off completely.

"It's probably kind of bad if we get horny over something like this," Kylie said, making an observation rather than giving any indication of having a problem with it.

"You too huh?"

"Uh huh, don't know why. Maybe because I think people going by might think I'm naked in here if they see me. My bra's not all that obvious from a casual glance through the window you know."

The off-white of her bra was obvious enough to me, but I took her point on how it didn't contrast with her skin nearly the same way her panties did. Or the way most any other colour would.

Our game went on hold for a while as Kylie kept looking out her window, or behind us to keep track of other cars. I tried my best to get my mind on something else and let my erection go down since dealing with it simply wasn't going to happen for a while. I didn't have all that much success since it was nearly impossible to keep from glancing at my sister several times a minute.

"Is it okay if I..." Kylie said suddenly, then stopped and turned away from me again.

"If you what?"

"Never mind."

"Come on, if you what?"

"I'm just... it's so weird sitting here in my underwear." I expected her to ask if she could put her clothes back on and I was ready to say yes since she had done enough it couldn't be considered backing out. Instead, "I'm getting kind of horny," she finally said, reluctantly and in a quiet voice.

"Oh."

She didn't come right out and say it, but the only thing that made sense was that she wanted to masturbate. In that context it was odd that she said anything at all. We'd certainly been getting more sexually comfortable around each other, but this just seemed like a step too far. Actually, last night had been as well come to think of it.

I caught Kylie squeezing her legs together in frustration the next time I glanced at her and felt a small surge of pity for her. I was turned on more than I liked from her state of undress, how much worse would it be for her? Not only dealing with me, but also the chance that any one of those drivers going by might see her too.

"You know I really wouldn't mind," I said, leaving it purposefully vague what I was talking about so she could misinterpret if she wanted.

Kylie raised an eyebrow and looked at me assessingly.

"You think you could keep us on the road if I did?" she said, only half-joking.

"Pretty sure."

I was worried she was going to think I was just being a complete perv, which I sort of was, but my offer was at least partly a genuine attempt to help her out.

"What the hell," she said after a brief pause.

I really wished I wasn't driving at that point. Kylie abandoned all pretense of restraint and slid her hand under her panties, letting out a long sigh of relief as she finally got to ease some of her tension. I had neither a good angle nor the luxury of being able to focus on her as much as I wanted. Perversely this might have gotten me more worked up than if I'd been watching intently since my mind had to fill in so many of the gaps, and did a pretty good job at that.

For several minutes all I heard was the sounds of my sister working her wet pussy and her increasingly ragged breathing. The smell of sex slowly permeated the car, and combined with everything else was enough to very nearly make me lose it.

Finally Kylie hit her orgasm, her legs stretching out as much as possible in the space she had while a small, sexy moan escaped her lips. She slumped back in her seat as she finished and gave me a sheepish grin.

"Sorry 'bout that," she said. "Though I don't think you minded too much somehow."

The tent in my shorts was all too obvious, and I'm sure there were other signs that gave away what I was thinking.

"Well, it's over now anyway." I shrugged.

"I guess. Must be my turn to drive soon."

I had no idea how long I'd been driving, I couldn't even seem to manage the simple math it would have taken from looking at the clock on the dashboard. I could sense Kylie's ulterior motive for offering to take over, but I had no intention of fighting her over it.

At the next convenient opportunity I pulled over and got out of the car to switch seats. Kylie stayed in the car and simply hopped over to the driver's seat while I was walking around, apparently content to remain half-naked. As I sat back down I noticed a damp spot right about where her pussy would have been.

"Seat's a little wet," I commented innocently.

"Shut up!" Kylie blushed, an adorable reaction given what she'd just done, and flipped me off when she caught my smirk. "And don't you still owe me?"

"Yeah, I do."

I had only started to take off my shirt when Kylie stopped me.

"Uh uh, shorts," she said, pointing helpfully at my legs.

"Hey, you got to pick what you took off."

"Yeah, but... come on, that's not fair."

"Sure it is, I won two to your one."

"Jase, don't be an asshole about this. Please. I thought we could... I don't know. I let you watch me and everything, that's not something I do for a lot of people."

I was planning on giving in anyway, but hearing my sister come very close to getting upset with me made refusing even less of an option. The last thing I wanted was for her to be mad at me now.

"You're right," I said. "I did get to see more than I should have strictly speaking."

"Damn right."

Her expression of annoyance turned to anticipation as I slipped out of my shorts. I had boxers on underneath and they did a much worse job of hiding my erection than my shorts had, which wasn't saying much. Still, the way Kylie's eyes widened as she saw the way they tented over my crotch almost made it all worthwhile.

"Happy now?" I asked.

Kylie shrugged and looked away for a moment instead of really answering, but I could tell she must have been feeling the same sort of guilty fascination with my body that I was with hers.

"Guess you really liked watching me," she said quietly.

"Yeah, I did. Fucked up isn't it?"

"Pretty much." She smiled, then chewed on her lip briefly. "You could... take care of it too if you wanted. I mean, I did already so it's not like it's any worse than that."

"You'd probably be able to see more than I could," I pointed out, not that it was going to be enough to dissuade me since I needed to get off really bad.

"Your choice."

She acted casual, or tried to, but she couldn't completely hide her interest. We were both too far gone to pay enough attention to our calm, rational sides.

Wordlessly I reached under my boxers and gave my cock a long, slow squeeze. It felt so good to finally be able to touch it, when I was as turned on as I was I didn't think I'd ever held back for so long. The confines of my underwear were usually not ideal for masturbating, but I wasn't ready to whip it out in front of my sister just yet. It wasn't exactly going to be one of my longer sessions either.

While Kylie had joked about it earlier, I really was worried a couple times that I was going to distract her to much and we'd crash. Luckily we never did, but her eyes were on me, or rather the outline of my rapidly stroking hand, as much as she could manage. Knowing she was watching me so intently was both embarrassing and strangely arousing.

After a few minutes I was getting ready to cum, images of my sister firmly at the front of my mind as I did. It was going to make a huge mess of my boxers again, but I was beyond caring. I just hoped I didn't run out during the trip and have to get them cleaned somehow.

My orgasm marked the release of all my pent up tension and allowed me to sink back into a much calmer state as I finished. I felt an incredible contentment, not nearly as concerned as I should have been over what Kylie and I had just done together. In fact, I probably spent more time thinking about what else might happen between us than worrying about what had already passed. After all, we were going to be sharing another room that night, there was no telling what that might bring.

****

The rest of the car ride was quiet, though not as awkward as it could have been. It had more to do with Kylie and I each spending a lot of time thinking than it did with us not wanting to talk.

We spent some time with our parents at supper that night, somehow we'd made pretty decent time and dad was in a good mood. I didn't dare spoil anything by mentioning that maybe he'd miscalculated the distance for the second day.

The only real problem was how I kept worrying that mom and dad had to see there was something going on between Kylie and me, though any signs of it were far more noticeable to me since I was looking for them. Kylie basically told me to chill out a little when she had a chance, though I caught her looking nervous a couple times too. It was like an involuntary reaction that we'd built up from all those times we'd been caught doing something wrong as kids. Parents might not be omniscient, but that didn't mean they didn't seem like it at times.

It was a relief for me when we all finally retreated to our rooms, leaving Kylie and me alone. Her I could deal with. Well, not in a totally normal way recently, but at least I didn't have to watch everything I said around her. She already knew about, and was a major part of, my current biggest secret.

We started getting ready for bed earlier than we normally would have, which could have simply been because there was nothing much else to do. That said, I was glad to see Kylie pull out her laptop before she climbed into bed since it meant we were both probably thinking the same thing.

"Are we having move night again?" I asked.

She snorted softly, but didn't look at all surprised by the question.

"If you want."

I went to the bathroom to get changed first, then joined my sister on her bed. Once again we both covered partly up under the sheets to preserve some sliver of decency, even if it was getting to the point where any such attempt was a formality at best.

We had better luck with videos this time, the first one Kylie tried seemed pretty good and it was almost twenty minutes long so it would last a little while. The guy in it was average enough, nothing about him stood out enough to distract me. The girl on the other hand bore a passing resemblance to Kylie, though I thought I was just imagining it at first since I'd been obsessing over her more than I should lately.

"She kinda looks like me, doesn't she?" Kylie said after a few minutes, confirming what I'd noticed.

"Well, yeah. I guess she does."

Shit, now it was going to be even harder to not mentally put Kylie's face on the girl's body. The more I watched the less I could control my imagination, eventually giving up and closing my eyes so I could picture exactly what I wanted to. I wasn't as subtle about it as I hoped though.

"You're thinking about it aren't you?" Kylie asked. "About me."

"Yeah. It's hard not to."

"We've been making things difficult for each other haven't we? It's getting so hard to be good. Maybe I never should have tried to start anything. Maybe this is why everybody's so repressed, 'cause shit happens when you aren't."

I smiled humourlessly. "If people weren't repressed, what we're doing wouldn't even be an issue. As long as we don't get too out of hand, it's all just fun and it's not hurting anyone. Except society doesn't see it that way."

"Is that how you see it, or are you just trying to rationalize it for me?"

"Both probably. But I really... I mean, I don't regret anything we did. As long as you don't either I think we'll be okay."

"No, I don't regret it. How far do you think is too far though?"

"Well... sex obviously. Beyond that I don't know, I haven't had a chance to really think about exactly where the line is. If we haven't passed it already of course."

Kylie didn't respond to that right away and I assumed she was thinking it over. It was a weird time for introspection, but if she had things she needed to work out then I was hardly going to say anything about it. If I wasn't busy jerking off I might have ended up lost in thought as well.

"I liked having you look at me today," Kylie said, almost in a whisper. "When we were in the car. I think that made me hornier than anything else, seeing how much you kept staring at me."

"Well you're hot, what else was I gonna do when you started taking clothes off?"

"But I'm your sister, it means more than that. I know because I was looking at you too and... I kinda wanted to see more when you were jacking off. I've seen naked guys Jase, and there's plenty on the internet, but they aren't like you. You're different."

"Because you're not supposed to think of me like that?"

"Partly, yeah. But I think maybe because you mean more to me than anyone else ever has."

"Kylie...."

"Seriously, I love you. I know it's not supposed to include any sexual feelings when I say that, but it does."

The laptop and the porn on it were rapidly disappearing from relevance as I dealt with the new information from my sister. I didn't think she was crushing on me or anything, I really hoped she wasn't anyway. If she just saw me as interesting and forbidden the way I did her then we were fine. Probably. I loved her and a part of me wanted to see her naked, but that was about as far as it could get between us before we were in serious trouble of doing something irreversibly stupid.

"You know I love you too," I said. "And it's not as innocent as it should be when I say that either. Let's face it, we're quite similar in a lot of ways. Almost like we're related."

"Yeah, almost." Kylie smiled, then chewed on her lip. "How often do you think we're thinking the same things and don't even realize it?"

"I dunno, there's really no way of knowing that. Why?"

"Because there's something I want to do right now, and if you wanted it too it would make it easier."

Even though I didn't know what she was talking about, the way she said it was suggestive enough to make me nervously excited. It had to be sexual, there's no reason she would bring it up otherwise, and it was hardly going to be too extreme. Other than that I couldn't be sure.

I must not have responded quickly enough for Kylie because she didn't wait. With her eyes locked on mine she reached under the sheet to my leg, then slid her fingers higher. I said nothing, hardly daring to breathe as I clued in to what she was doing.

"Let me do it for you," she whispered.

"You don't have to," I said, making the most token protest of my life.

Her delicate fingers closed on my cock, which had begun to soften in the midst of our conversation but now returned to life. She stroked me through my boxers until I was fully erect again, then tugged my waistband down with my help until my cock sprang free and was covered only by the sheet.

"Does that feel okay?" she asked.

"Fuck yes, that feels great. But you really don't have to."

I kicked myself mentally even as I spoke for trying to dissuade her again. Sure it was kind of bad that my little sister was jerking me off, but it was so very good too. For different reasons of course.

"It's not only for you," she said. "Honestly, I wanted to do this since last night. Watching you in the car earlier, that didn't help either."

Her hand gradually gripped me more confidently as she continued stroking me, less like she was getting ready to pull away at any second. She had probably been worried that I'd tell her to stop at first, but when I didn't initially put up much of a fight she correctly guessed that I wasn't going to.

"I had similar thoughts you know," I said. "Though they had a lot more to do with wanting to see you than touch you."

"Well, maybe sometime soon you'll get to," she said.

She shifted a little closer to me, close enough that our hips were almost touching. I didn't know if that was a hint, or just her getting more comfortable. Either way I decided if she was going to be jerking me off I probably had some freedom in what I did. I placed my hand on her leg just above the knee, nowhere inappropriate yet, but just enough to ask permission. She barely responded to me at all except for her eyes flashing at me for a second with a poorly-concealed grin.

Kylie kept stroking me while I reached farther up her thigh, eventually coming to her panties. I was kind of hesitant at that point, I was doing something I never thought I'd be doing with my sister until very, very recently. She had started it though, and the slight widening of her legs as I approached her crotch was a fairly unambiguous sign of what her feelings were on the matter.

"It's okay," she said.

I had my doubts about that, but I wasn't going to let it stop me. Once I found the waistband of her panties it was easy enough to slip my fingers under them, and all of a sudden I was touching my sister's pussy. Other than what felt like a small triangle of hair right at the top, her pussy lips were perfectly smooth. She gasped softly as I made contact, then made a sound of encouragement as I continued to explore.

She was wet even before I touched her, unsurprising considering she'd been masturbating already, and my finger slid easily along her slit. It was only then that the full realization of what I was doing hit me, that I was actually fingering my little sister. At the same time I didn't freak out nearly as much as perhaps I should have. Sister or not, Kylie was still a girl and she felt exactly like a girl is supposed to. Physically speaking I knew what I was doing, even if emotionally I was drifting farther and farther from known territory.

After another minute or two I pushed a finger inside her, slowly penetrating her while her hand squeezed harder on my cock in response. She was going to make me cum, she was well on the way there already, and I wanted to do the same for her. I wanted to make her feel as good as I did, though I suspected I couldn't manage that. My movements felt so clumsy compared to hers, and even if her job might have been the easier of the two anyway I wished I could do better.

"Getting there," I mumbled, sensing my orgasm approaching long before Kylie's.

"Okay, hang on a sec."

I experienced a surge of disappointment as her hand was suddenly gone, my immanent orgasm aborted.

"What-"

"I said just a second, I'm just trying to keep things a little tidier this time. You always seem to make a bit of a mess."

"Like I can help it," I muttered.

Kylie pulled her panties down, brushing my hand with the material as she did, then all the way off. I was confused until I felt her grasp my urgently waiting again, this time with her panties wrapped around the head.

"What the hell?" I managed, groaning in pleasure as she resumed stroking me.

"You can just shoot into them, won't have to clean up later."

There was something in her voice I was pretty sure I'd never heard before, an undisguised lust at what she was doing. As sensible as her decision may or may not have been, it made the whole thing somehow dirtier than it had been before and pushed me even closer to cumming.