13 Temmuz 2024

On the Road to Somewhere

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Vacations; they were supposed to be fun and relaxing in theory. And they usually were once we got wherever we were going, but dad never seemed to understand the idea of having fun along the way. It was all about getting where we were going on schedule and we could relax once we arrived.

This year was a bit different than any previous holiday with my family. Instead of being stuck in the backseat with my sister while the landscape rolled past for hours on end, we had taken two vehicles and Kylie and I got to drive ourselves. It was a small improvement at least and it never would have happened if not for dad’s most recent purchase.

He hated us calling it his mid-life crisis, but I think that’s only because it was closer to the truth than he liked. He didn’t go for the stereotypical motorcycle, instead choosing a sports car he’d always wanted. It was absolutely out of the question that anyone but him would get to drive it of course, but it did provide an accidental benefit in only having two seats. It meant that with our parents traveling in it there was no choice but for Kylie and I to take another car. It still took a little persuasion, but not too much since he really wanted to spend time with his new toy and this was the perfect opportunity for him.

As far as I was concerned driving with Kylie was way better than with both her and our parents. Dad could get frustrated if we weren’t making good enough time so it usually alternated between mom trying to get us to play road games and dad telling us to be quite so he could focus. My sister was much easier to deal with.

Unfortunately just because we were traveling separately didn’t mean we didn’t have to stick to the schedule. There were two hotels we needed to make it to at night over the two and a half days of driving, not leaving us much time to take detours or stop anywhere interesting. Mostly we were limited to gas stations and restaurants whenever we needed either gas or food respectively.

We were pretty much on track for time the first day when we actually had to make our first gas stop. We played a quick round of rock-paper-scissors for who had to pump the gas and I lost. Kylie wandered into the attached convenience store as I filled up the car and only reappeared after I’d finished up and was debating going in after her.

“Hey Jason, you finished up there yet?” she called as she returned to the car. I didn’t bother to answer since it was pretty obvious that I was indeed ready. “They had slushies so I got you one too,” she continued.

I looked up as she approached, having temporarily been distracted by an overly loud truck going by. My eighteen year old little sister was wearing just a t-shirt and shorts with sandals and carried a slushie in each hand, holding one out for me when she got near enough.

“Thanks,” I said, accepting the drink.

I was dressed pretty similarly to Kylie, except with sneakers instead of sandals. We were getting into the hottest part of summer and there was no point wearing any more than necessary. It wasn’t so bad in the car with the air conditioning on, but coming out of that into the heat made it feel worse than it was.

I took an experimental sip from the overly large straw as we climbed back into our seats and I started the engine. It was good, but I couldn’t place the flavour immediately.

“What kind is this?” I asked, signaling my turn back onto the road and waiting for an opening in traffic.

“Red,” Kylie said with a shrug.

I shot her a look before turning my attention back to what I was doing.

“Seriously, I don’t know any more than that,” she said. “I got us each different colours in case I didn’t like mine.” She grabbed my slushie and tried it, then handed it back. “Nah, mine’s better anyway.”

“Lucky you.”

Eventually I got back on the highway and settled in for another long stretch of driving. We’d had music for the first little while, then Kylie’s mp3 player died and we wouldn’t be able to charge it until we got to the hotel that night. The radio stations we picked up were more or less a coin flip as to whether they’d be any good. Plus they were constantly shifting as we got in and out of range of different stations.

Kylie took control of the radio for a while, changing stations at a whim or because she didn’t long the song that was playing. About the time she finished her slushie she gave up and just turned it off, reclining in her seat as she placed what remained of her drink in a cup holder.

“I’m bored,” she announced.

She swung her feet up onto the dashboard, revealing that she’d also discarded her sandals at some point leaving her feet bare.

“Well what do you want me to do about it?” I asked. “We talked about anything interesting already, you should have brought something to amuse yourself.”

“Come on, you know I can’t read or anything ’cause I get carsick. Let’s just, I dunno, pick a topic or something. We can’t have covered everything already, we still have two more days to go.”

“Fine, you start matadorbet a conversation and I’ll join in.”

“That’s not how it works smartass. If I could just start a conversation like that I’d already have done it. You don’t give a shit about anything I want to talk about.”

“Probably because I don’t know most of the people you bring up. Just, like, pick something we’re both interested in.”

“So… Monty Python or sex then huh?”

I rolled my eyes. “I’m sure there’s more than that.”


Kylie stared out her window for a while, not pressing me any further for entertainment, and I took the chance to make sure we were still going the right way. As far as I could tell we were, but it wouldn’t have been the first time I’d missed a turn off because I was distracted if we weren’t.

“You ever tried anal?” Kylie asked all of a sudden.

“What?” I said, figuring I must have misheard.

“Anal, have you tried it before? Like in the butt?”

“I know what it is, I just… you must really be desperate for something to talk about.”

“Or maybe I’m genuinely curious.”

“Why the fuck would you want to know that all of a sudden?”

“Okay, so I’m really bored. You gonna answer or what?”

“I will if you will,” I said, upping the stakes a little. If she could get personal then so could I.

“Fine, you first,” she said after only a brief hesitation.

I still wasn’t totally comfortable with the question, but Kylie had accepted my challenge and I couldn’t very well back down now. It wasn’t that I minded talking about stuff like that with her, just that it didn’t happen very often. It felt a bit weird.

“Okay, yes. I’ve tried it once,” I finally admitted.

“Wow, really? What was it like?”

“Uh uh, your turn,” I insisted.

“Nope, never did it,” Kylie said, which I probably could have guessed given her reaction to my answer. “Now what was it like?”

“If I tell you, you tell me why you’re really asking okay?”


It wasn’t easy coming up with a description that would both satisfy my sister, and wouldn’t be too explicit. I did my best anyway.

“It was… good. I mean it’s, you know, tighter and everything, but on the other hand it takes more effort to do it right. It’s pretty hot though and it’d be fun to do every now and then, but not something I’d probably do constantly.”

Kylie nodded slowly and looked thoughtful.

“So it’s not, like, way better than regular sex or anything?” she asked.

“Well, I don’t know that I’d say that for sure. I only did it once, and it wasn’t like either of us really knew what we were doing. I can’t believe I’m saying this, but maybe you just need to try it for yourself.”

“I want to. I thought I was going to with my last boyfriend, but I couldn’t convince him. I thought all guys were into that.”

“Do all girls like the same kind of sex?” I countered.

“Well, no. But… he didn’t even want to try it.”

“Maybe he thinks it’s gross or something, who knows. If it’s that big a deal to you it might be for the best that you’re not together anymore though.”

“I… I don’t even know. I just wanted to try it, that’s all.”

Kylie reclined her seat slightly and repositioned herself more comfortably. I found myself looking at her more often than I probably should have been since I was driving, and her feet on the dashboard didn’t help since they were in my field of view even when I forced myself to stare straight ahead.

“So that probably answers my question anyway,” I said after a moment.

“Pretty much,” Kylie agreed. “I was hoping you might have some obvious solution for me, don’t know why.”

“I’m your brother, not a sex-advice columnist. Speaking of which, was I really the only person you could have asked?”

“Uh, pretty much the only guy I could ask, yeah. I talked to a couple friends, girl friends I mean, and they pretty much pretended like they had no interest whatsoever. Or maybe they really didn’t have any interest, I dunno. To them it’s the sort of thing that you only do for a guy because he wants to and you really like him.”


It was kind of nice to know Kylie felt like she could talk to me about sensitive stuff. Honestly, I guess she would be the first person I’d go to about a lot of things too, though it didn’t come up often since like a ‘typical’ guy I was more inclined to keep questions or insecurities firmly to myself.

“Most of the boys I know are too immature to even bother,” Kylie continued. “And I’d be worried about giving them the wrong impression too. You have to be careful talking to guys about sex sometimes.”

“Great to know I’m safe,” I said, suddenly a little less happy about her picking me.

“Aw, don’t be like that.” Kylie sat up properly for long enough to give me a hug that sent me swerving out of my lane a little at the unexpected contact. She also gave me a quick kiss on the cheek before returning to her reclined position. “You know I love matadorbet giriş you right? But you’re my brother, at worst you’d get embarrassed and refuse to talk about it. That’s not as bad as getting the idea that I secretly want you and starting to act all weird around me.”

“Has that happened, dare I ask?”

“Happened to one of my friends actually. She got it sorted out eventually, but still.”

“And you’re not worried about things getting weird between us for different reasons?”

“Nah, I know you too well. You’re open minded enough not to freak out on me over something like this.”

Kylie had closed her eyes at some point and as I let the conversation drop, she did too. I didn’t think she was actually sleeping, but I guess she had enough to occupy her thoughts for a while. I had to admit that despite it being kind of awkward, I liked that she would come to me with something like that. It was nice to be a big brother to her every now and then.


We arrived at our hotel that night about twenty minutes behind our parents. Apparently that was acceptable enough because dad didn’t say anything about it.

Kylie and I were sharing a room right next to the one our parents were in, we got one key while mom took the other ‘just in case’. There were two beds a couple feet apart, one for each of us, with a bathroom we’d have to share. Basically nothing different from any of our previous holiday experiences.

It wasn’t until we were both getting ready for bed that anything unusual happened. Kylie was sitting on her bed with her laptop, having already changed into just a nightshirt. I was planning on sleeping in my boxers, though I still had my shirt on until I was actually ready to go to sleep.

I turned off the main room lights before heading for my bed, Kylie’s bedside lamp providing more than enough light for me to see. I also had my laptop pulled out of its bag and was content with staying up a while longer until my sister was done. The hotel had free wi-fi so there was plenty of stuff I could do, even if what I most felt like was looking up some porn and that just wasn’t going to happen with Kylie right there.

Then I caught a glimpse of her screen.

I thought at first I must have imagined what I saw, my recent thoughts altering my perceptions somehow, because it looked suspiciously like naked people. It was easy enough to check, I simply looked again and instead of discovering an innocent illusion it was exactly what it had seemed.

“Are you watching porn?” I asked.

“Yeah, we get wi-fi here,” Kylie said as though that explained everything.

She wasn’t even trying to hide it or anything, it would have been simple enough to turn her laptop so I couldn’t see it. At least she had turned off the sound though.

“It’s not going to bother you is it?” she asked after a moment, finally turning her attention from her computer to me.

“What, my little sister looking at porn? Why would that bother me?” I said sarcastically before continuing on a more serious tone. “Really though, it’s fine I guess. I just… didn’t expect it. You’ve been acting kind of different on this trip.”

“I have, haven’t I,” Kylie said almost to herself. She visibly waged a brief war with herself over whether to tell me something or not, then shrugged. “I was kinda hoping you’d notice about the porn.”

“Maybe I don’t need to say this, but I’m going to anyway. Why?”

“Because I’m pretty sure you already knew I did stuff like this, and I know you do too. But today in car is pretty much the first time we ever talked about sex at all.”

“Maybe ’cause it’s weird for us to be discussing.”

Kylie smiled wistfully and seemed to be remembering something.

“Do you remember when you first started swearing around me?”

“Um, not really,” I said, unable to come up with any specific memories of the occasion.

“I do,” Kylie said. “It made me happy when I realized you thought of me like someone you could say stuff to that you couldn’t even say to mom. It was like I wasn’t just an annoying little sister you put up with and you actually liked me.”

“I always liked you Ky.”

“Yeah, but it’s not always easy to tell when you’re a kid looking up to your big brother. Plus you made me feel more grown up than anyone else ever did. You always have.”

“So… you wanted me to know you watch porn?” I asked, trying to figure out where the story was going.

“It’s not about the porn dumbass.”

I arched an eyebrow, but Kylie shut up after that and I assumed I was supposed to have understood her point by now.

“Well then it’s about us,” I said slowly. “You want to… well something obviously, but I don’t know what.”

“I want us to not be like all those other people out there who refuse to talk about stuff everybody knows exists anyway. What the fuck is so terrible about sex that we have to pretend it doesn’t exist half the time?” She pushed a few strands of hair back behind her ear reflexively. “Jason,” she continued softly, “a lot of what we had growing up was based on us just being ourselves because we could trust each other, but it’s like there’s this one part of our lives we can’t share.”

“It would be nice not to have to hide things from you,” I said, agreeing indirectly with my sister. “And you’re right, there’s no reason any mention of sex has to be buried away when we’re around each other.”

Kylie didn’t say anything at first, but I could tell that was more or less what she’d been hoping to hear. If nothing else I had to admire the courage it took to bring up a topic like that. Just because we’d agreed it shouldn’t be a big deal didn’t mean that there were no psychological hang ups surrounding it.

“So you want to watch some with me,” Kylie asked after a couple minutes, nodding vaguely toward her laptop.

I hesitated for a couple seconds, then started moving toward her.

“This is a hell of a way to get some sibling bonding time in,” I joked, trying to pretend like I was completely comfortable with the situation.

“More fun than getting kicked outside to play together like when we were kids though isn’t it?” she replied.

“There is that.”

Kylie scooched over for me as I stepped to the side of her bed and let me slide under the sheets with her. The bed wasn’t really big enough for two people to have a lot of space, but we weren’t cramped either.

I got my first good look at what my sister had decided to watch then, a little surprised to discover a still image of a girl getting fucked in the ass. It shouldn’t have been all that unexpected I suppose, not when I considered what she’d wanted to talk about in the car. Then she resumed the video and I got distracted from my thoughts for a few moments.

It wasn’t like I’d never seen that sort of thing before, I was familiar with a pretty wide array of porn and anal was far from being uncommon. What was different was my little sister being right there watching the same thing. Initially it was reminiscent of those jaw-clenching moments when a nude scene popped up in a movie we were watching with our parents. After a while though I started to relax and stopped thinking so much about what might be going through Kylie’s head.

“They always make it seem so easy,” Kylie said eventually. “Do you think that’s ’cause people like it better that way, or would it just be because they have so much practice and they don’t bother faking inexperience.”

“Could be both.”

As much as I didn’t really care about the whole ‘porn creates unrealistic expectations’ thing, every now and then it did tend to show up in practical examples. Outside of porn stars I felt pretty confident that girls who could take an above-average sized cock up the butt with no more preparation than slapping on a little lube were fairly rare.

“Are you into this clip, or is it okay if we try something else?” I suggested after another couple minutes. “Don’t know about you, but this girl’s just not my type.”

“Fine with me, I just didn’t want to be as picky as I usually am when I’m alone. It sometimes takes me a while to find a good one. Honestly this really wasn’t working for me either. You want to try something different next?”

“Nah, anal’s okay if that’s what you want to watch.”

“I do have a bit of a fascination lately,” Kylie said with a hint of a smile.

After a couple obvious failures Kylie found another video that showed more promise. It involved a little foreplay followed by, once again, anal sex. What made it interesting was when the couple were joined by another girl with a strap on and a variety of different positions ensued. I didn’t know how Kylie felt about it, but personally I preferred watching naked girls to naked guys any day so adding another was fine by me.

As fun as it was to watch however, I was getting pretty seriously turned on and my cock was approaching full erection. The sheets that covered our lower halves prevented my condition from being visible to Kylie, but I couldn’t jerk off without her noticing. Watching porn together was one thing, masturbating together was quite another.

“So is this one okay?” Kylie asked, not looking away from the video even for a second as she spoke.

“Uh, yeah. It’s pretty good.”

“I was planning on, you know, taking care of myself. I guess that’d probably be too weird though right?”

“Yeah, probably.”

So we were thinking the same thing, not that it helped very much. I briefly contemplated stepping into the bathroom for a little while in order to give us each some privacy.

“We could just make sure we watch the screen,” I found myself suggesting instead.

“Like, just ignoring each other,” Kylie said, catching on right away.

“We’re gonna do it anyway, we both know it. It’s no worse than normal except we’re a bit closer than usual.”

I’d never realized just how amazing the brain is at rationalizing something it wants until then. Even as the moment was happening I knew it was about as flimsy as pretexts get, but I didn’t stop. My hands, as well as Kylie’s, that had remained conspicuously above the sheets until then disappeared beneath and despite being hidden we both knew what the other was doing.

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