On the Road to Somewhere

All I did at first was rub my cock slowly through my boxers, not wanting to be too hasty and obvious about getting off. It was actually the first time I'd masturbated in the same room as someone else and even with all my experience I was constantly evaluating every move I made in fear that it might be something embarrassing to do when someone might see.

My efforts were probably unnecessary since we'd agreed not to look at each other, more or less, and it wasn't like it was a big deal if I made an odd face while I jerked off. Once again it was all just matter of time before I relaxed into the new situation and stopped caring so much about what Kylie would see if she did happen to glance over at me.

It was actually me who broke our 'rule' first, or I thought it was at least. Kylie could well have peeked without me knowing. It wasn't on purpose or anything, just an instinctive response when I heard a soft moan come from beside me.

I couldn't see much other than her arm moving under the covers, but I could imagine the general idea of what was going on. Kylie caught me looking and didn't seem to mind too much, not giving me much more than a raised eyebrow as if to say "thought we weren't supposed to look."

"Sorry," I whispered.

I turned back to the video and managed to keep my eyes on it for a while, but my mind was on Kylie. Even though she was my sister, she was real and therefore had something pixels on a screen couldn't replicate. More than once I caught myself trying to picture what she would look like without the sheets covering her, with her fingering her pussy right where I could see. I felt guilty for even considering it, but it wouldn't be the first time I'd jacked off to something I wasn't fully comfortable with.

Eventually I did take another peek because I didn't have enough self-control not to, only to discover Kylie was also looking at me. There was a pretty blatant tent in the sheet over my lap that shifted as I stroked my cock underneath. It was almost certainly easier for her to picture what I was doing than vice versa.

"We're not doing very well at not looking so far," she said.

"No, we're not," I agreed.

Fortunately, before the tension increased too much between us I felt my orgasm approaching and it distracted me from my other thoughts. I stroked myself faster and closed my eyes, ignoring the fact that it was the image of my half-covered sister that I saw while I finished myself off. I realized too late that I had no plan for dealing with the mess I was going to make and, lacking any better options, I came into my boxers since at least that was easier to clean up than getting my cum all over Kylie's sheets.

When I dared open my eyes again I found Kylie with her mouth hanging halfway open and her arm moving noticeably more frantically.

"Did you just..." she said.

"Yeah."

I was no longer horny, but I was too relaxed to worry about where I was staring at that point and I ended up watching as Kylie got herself off right beside me. I knew she'd done the same and I wondered just what exactly she was imagining, whether she was thinking of me sort of the same way I had been thinking of her. It was still weird to consider, but not as much as it should have been.

Finally the two of us lay motionless together with our breathing slowly returning to normal as we silently toyed with whatever thoughts came to us. I was the first one to move, partly because I was the one not in my bed and partly because I didn't like the idea of sitting around too much longer in my cum-soaked underwear.

"Where... never mind," Kylie said, acting as though she didn't want me to go right away before realizing what she was saying.

"Gotta clean up," I explained as vaguely as I could, even though I knew she'd figure out what that meant.

"Oh, right."

She gave me an embarrassed smile and I returned it before grabbing a pair of shorts and stepping into the bathroom. I didn't bother trying to clean up my boxers, just pulled them off and wiped myself off as best I could before putting on my shorts purely for the sake of a little modesty when I reentered the main room.

Kylie had put her laptop away by the time I got back, though she left her lamp on for me until I made it back to my bed. I crawled onto my mattress suddenly tired and ready for sleep.

"Good night," Kylie called softly.

"Night Ky," I mumbled back.

I was asleep even before I had a chance to start worrying about what we'd done and what it would mean for tomorrow.

****

"Kylie! Jason! Are you two even up yet?"

I was startled awake by the sound of my mother calling us and pounding on the other side of the door. The unmistakable clicking of her key in the lock and the door starting to open made me panic for second before I realized there was absolutely nothing she would see that would be out of the ordinary.

"Honestly, you know your father wants to be out of here by eight-thirty at the latest," mom continued. "And here I thought you two would be responsible enough to get yourselves out of bed."

"It's a vacation," I protested. "It's supposed to be okay to sleep in."

Mom walked across the room and opened the curtains, eliciting groans from both Kylie and I as we pulled our covers up over our heads.

"You can sleep all you want once we get to the resort," mom said. "Though that would be a bit of a waste. And if anyone knows how much that excuse isn't going to fly with your father, it should be you two."

The memory of having a bucket of water dumped on me one year when I overslept leapt unbidden to my mind. I did indeed understand that a need for sleep meant nothing in the face of dad's schedule.

"All right, we're coming mom. Just give us a couple minutes," Kylie said in a tone that suggested she was only trying to get our mother out of the room.

As soon as we were alone again Kylie let out a big sigh and struggled out from under her covers.

"Well, we don't have time," she said. "You want the bathroom first? I can't promise you'll get a chance at it otherwise."

"Yeah okay. I'll be quick."

Kylie, being a typical girl in some ways, did take longer than me in the bathroom most of the time. She really wasn't all that bad about when she knew she didn't have much time though.

We each had a quick shower before getting our stuff together and meeting up with our parents. We got chastised for taking too long and now there wouldn't be a chance for us to eat before we left, and I had to restrain myself from rolling my eyes while Kylie assured them we'd hit a drive-through or something on the way.

For the first half-hour or so of driving we occupied ourselves with waking up and eating our breakfasts that we picked up from a fast-food place. Not a great start to the day, but at least with our minds on other things there was very little residual awkwardness between us over the events of the previous night. I took the first shift of driving and once we were both settled in Kylie dug her mp3 player out of her bag.

"Shit!" she exclaimed. "I didn't even remember to charge it last night."

With a look of disgust at herself she chucked her bag into the backseat and slumped down in resignation while I chuckled at her misfortune despite it affecting me as well. She crossed her arms over her tank top and glared at me.

"I wouldn't laugh so hard," she said. "It just means I'm gonna need more entertainment today."

"You have your laptop, you could always check out some more porn," I said.

"First off I wouldn't trust you not to crash us if I did that, secondly no internet dumbass."

"Oh yeah. Well you might have had some saved, how'm I supposed to know?"

"I dunno. Point is, you need to come up with something better than that."

"Why do I have to? I'm not the one who's bored."

"Because you know just how intolerable I can be if I want to," Kylie said with a smirk.

"And you think I can't?"

"Ugh, fine. I'll just try to have a nap or something."

Kylie assumed a position similar to the day before, reclining in her seat with her feet propped up on the dashboard. She crossed her arms and closed her eyes, for all I knew she was genuinely going to try getting some sleep. Personally I was fully awake at that point and didn't think I'd manage it in her place. It turned out she couldn't either.

"How the hell did we make it through all those other trips we made?" Kylie asked after only a few minutes of quiet.

"Annoying mom and dad, not to mention each other," I replied. "I believe we actually kept score one year."

"Oh yeah." Kylie smiled fondly as she reminisced. "Who knew there was actually an upside to us all traveling together after all?"

"Go figure."

"Still, there must be something we can do. Like, what kind of stuff would we get in way too much trouble with the parents to even think about?"

"Talking about anal sex like yesterday I suppose."

"Sexy stuff eh? That's something to consider."

Kylie sat thoughtfully for a couple minutes while I desperately tried to figure out if I should change the subject or not. If it was just talking that was fine, regardless of how dirty it got. If it became more than that, anything along the lines of masturbating together again, I had to decide if I was okay with it. Part of me was simply curious as to what my sister was going to come up with though, which made it hard to really commit either way yet.

"If you were alone in a car with a girl you liked for a while, what would you be doing?" Kylie finally asked.

"A girl who isn't you I take it?"

"Well duh, we already know how well that's going."

"That's not an easy question Kylie, you're obviously shooting for something we shouldn't do."

"Yeah, but you liked what happened last night didn't you? We definitely weren't supposed to be doing that."

Her expression told me she knew the sorts of things I'd imagined, maybe even that she'd been thinking the same about me. It was fucked up, but it was only between us and as long as neither of us objected what was it other than some harmless fun? At least, I hoped it was harmless.

"If you were someone else," I started slowly. "If you were, say, my girlfriend... and we were going to be stuck in car together for a while... I might try something like getting you to remove some clothing."

"Really? While there's other cars going past? That's a little risky." Despite her words Kylie's lips twisted upward in an interested smile.

"Well yeah, someone might see I guess. But if you, or whoever, slides down in the seat there's not going to be much visible. And if you only strip below the waist you're completely safe."

"Why does it sound like you've done this before?"

"Because I have. When I was with Becky I used to get her to do stupid stuff sometimes, nothing too crazy. I had to work her up to it, but a couple times I got her naked from the waist down and playing with herself while I drove. I almost crashed once, but it was pretty hot."

Becky would probably kill me if she knew I ever told anyone stories about her, but Kylie was hardly going to tell. What was more surprising to me was how I kind of wanted Kylie to take me up on the idea. It was the same feeling I'd had last night when I'd wished I could see her unobstructed as she fingered herself. Maybe it had been longer than I thought since I last had sex and I was just getting desperate to the point of seeing my little sister as a viable option for... something. Not sex though, there was no way I'd let it get that far.

"So what would I get out of it?" Kylie asked. "You get something to jerk off to, what would you do for me?" Her tone was teasing and she clearly expected me to protest at the idea of using her as masturbation fodder.

"Well... to use my ex as an example again, we usually played some kind of game and if I won she had to take clothes off, if she did then she got to come up with something for me to do. It really doesn't work out having equal forfeits when one of us has to drive."

"But if I won I could save it for when it was my turn to drive," Kylie said, evidently starting to get really interested.

"Yeah, I guess you could."

"So what kind of games?"

"Sometimes just, like, fifty-fifty things. Like whether the next restaurant we pass is McDonalds or Taco Bell. Nothing complicated. You don't think that would maybe be pushing things too far though?"

Kylie sighed. "Yeah, it would be. Kinda fun just to think about though, especially about what your face would look like if I actually did start stripping."

"Probably either a 'holy fuck my sister's crazy' expression or 'holy fuck my sister's hot'. Could go either way. And whichever way it goes you know it'd just push me closer to needing therapy."

"You are a bit of a nutcase," Kylie agreed.

"I wonder if it's still considered an Oedipus complex if it's your sister instead of your mother," I mused.

Despite the joking tone of our conversation, there was an undeniable tension building. Kylie was really close to going for it, teetering on the edge and waiting for a push, while I simultaneously hoped for that push to happen and for something to distract her.

We kept driving and still nothing happened, the mood slowly dissipating into a neutral silence. Neither of us were willing to commit to anything and so it was left to drift away like so many other unfinished thoughts.

"Taco Bell," Kylie said out of nowhere.

"What?"

"We just passed one, that's what I would have picked too."

"Oh. You know it can be anything right? Doesn't even have to be restaurants."

The influence of my sub-conscious on my words was less than subtle as I prodded my sister toward starting a game. I couldn't help it, now that I had spent so much time wondering I wanted to see what was under her clothes. I was definitely a sick puppy.

"Well what would you pick?" she asked.

Putting the ball in my court, making it my choice instead of hers. That wasn't helping. If I shrugged and gave a non-committal answer she'd probably leave it alone, at least until she got bored again, but I realized that wasn't what I wanted and all I'd really hoped for was an excuse to blame her instead of myself.

"How about cars?" I suggested, going with the first thing that occurred to me. "If ten red cars pass us before ten blue cars then I win. Or whatever colours you want."

"That's fine, you have red and I get blue."

And the choice had been made. It was something of a relief all on its own actually, and it allowed my mind to move onto strategy. Not that there was much involved in games of chance like this, but obviously certain colours were more common then others. I wished I could remember which ones they were.

More quickly than I'd anticipated Kylie swore and I realized I'd won the first round already. Luckily she had no idea I hadn't been counting too.

"I knew I should have taken red," she grumbled.

"Yeah, too bad for you."

"So now I have to...."

"Either your shirt or your shorts," I said, trying not to smile too broadly. "Or if you don't really want to, I mean I'm not gonna force you to." She was still my sister after all, that counted for more than my hormones.

"No, I lost. It was fair."

I fully expected her shirt to come off first, but to my surprise, and perhaps due to my suggestion that it was a safer option, Kylie actually reached for the top of her shorts once she finally made her decision. She had to struggle a little to get them off while in her seat, but soon enough she succeeded and tossed the now unnecessary garment into the back seat.

"So what do you think?" Kylie asked.

She didn't quite look at me and her hands fidgeted together in her lap when until she realized she was doing it and clasped them firmly together. Like any girl I'd known, or even myself for that matter, there was an instinctive need for approval when clothes started coming off. It was a nice thought to not care what anyone thought of your appearance, but it never seemed to go that way in reality.

"It's a good look for you," I said. "I like those panties too."

"I bet you do, fucking perv," Kylie said as a smirk replaced her nervous smile.

"Says the girl who was watching porn last night in our room."

"You didn't seem to mind too much at the time."

"Whatever. Seriously though, that's pretty hot," deflecting the conversation back to my sister's state of undress.

Kylie's panties were pink, not a bright pink but still an eye-catching contrast to her skin. I couldn't really see anything other than bare leg and underwear, but my gaze kept flicking to her crotch anyway. I can be easily entertained like that sometimes.

My sister clearly noticed how much attention she was getting from me and toyed with me for a few minutes. She would casually run her fingers over her thigh or open her legs wider then close them again, doing a bad job of pretending like it was all natural movements.

"I want red this time," Kylie said once the novelty had worn off a little.

"Fine. Lets do more though, like first to twenty. It went too fast last time."

As Kylie started counting again I once again didn't bother, instead watching both her and the road. I liked the way she acted completely normal once her mind was off her partial nudity, it made the situation even more sexy to me somehow. It was similar to the difference between regular porn and those rare videos where the girls didn't actually seem like they were faking everything. It was more real.

"Ha! I win!" Kylie burst out.

I winced and realized I probably should have been double-checking Kylie's count, but I didn't think she was cheating me.

"So, do I put my shorts back on or do you just owe me one now?" she asked.

"Up to you I guess."

"Hm, I'll go with you owing me then. I want to make sure I get something out of this."

"We probably should switch off of cars though, red seems too popular."

"Yeah, it does. What about, like, pickup trucks versus motorcycles or something?"

"Sounds good, I got bikes. First to twenty again if there are no objections."

This time I kept an eye on what was going past, wanting to see more of Kylie and also a little scared of what would happen if I lost too many times. A little hypocritical of me maybe, but the fact that I was trying to get my sister naked, even partially, was proof enough that my mental state was questionable.

I was heading toward losing two in a row and I could tell Kylie was getting excited when I got lucky and a whole group of bikers went by in the other direction. It was easily more than twenty bikes in less than a minute and my sister let out a heart-felt "fuck!" as her luck changed.

"Looks like your turn again dear sister," I said with a deliberately infuriating smile.

"Yeah yeah. Lucky bastard."

Kylie glanced around seeming to take in how close other cars were to us even though their relative positions would fluctuate. She sank farther down in her seat before starting to pull her tank top up over her head. I had a very hard time concentrating on my driving while her bare stomach came into view, followed closely by her bra. Her shirt joined her shorts in the back seat once it was off, leaving my sister in only her bra and panties.

"Can't believe I'm doing this," she muttered. "Some perv in another car is going to see me, I know it."

Not to mention the perv in this car who was already looking.

"No one's going to see anything," I assured her. "Not that you have anything to be embarrassed about."

"You saying I'm hot?"

"I'm saying you're fucking hot, yes."

"Good, 'cause I'd hate to have to beat you up while you're driving."

"As if you could," I scoffed. "Plus we'd really attract attention then, me swerving all over the road fighting you off."

"Yeah," she said in kind of a weird tone. "It's funny, it's not like being in my underwear is that different from a swim suit or something, but it feels different somehow."