On the Road to Somewhere

"So how'd that go?" I asked.

"Enh, pretty much what I expected," Kylie said. "They wanted to say something about my suit, they were pretty obvious about that, but they actually didn't. They might be ready to let me grow up after all."

"Oh like you've had it rough. They used up most of their parental concern on me, all you ever got was the occasional veto on your wardrobe."

Kylie stuck her tongue out at me in a deliberately childish move.

"There was more to it than that, not that I'd expect you to understand. You don't know everything about my life."

"Sure, whatever you say. What did they want anyway?" I asked just to change the subject.

"Oh, some stuff about how we're on our own for the rest of the night because they have plans or something. I guess they're worried we might starve without them around to tell us when it's supper time."

"That sounds about right for them."

"Speaking of which, it does mean we'll be unsupervised for a while. Wanna get room service later on and hang out in our room?"

"You know, I could probably go for that."

****

Despite the intentions I think Kylie and I both had, we didn't get up to much that evening. The nagging worry that our parents would come back unexpectedly kept our activities more or less innocent; mostly watching movies and enjoying a surprisingly comfortable couch. There was a little touching that went beyond a typical sibling relationship, but nothing that we couldn't extricate ourselves from quickly should the need arise. If only our individual bedrooms came with their own locks we would have had at least that little bit of comofrt to let us mess around without fear.

What I was really waiting for was bedtime, an odd source of excitement under normal circumstances. At least with our parents sleeping we could be reasonably sure they wouldn't be wandering around and possibly interrupting us at whatever we ended up doing.

I was slipping out of my clothes that night by my bed when Kylie came in through the balcony entrance. She was only wearing a shirt and panties, and the shirt was a regular one rather than a longer nightshirt. She stood and watched me until I had stripped down to my underwear.

"Going to bed?" she asked.

"Yeah. Maybe not by myself though," I said.

"I hope not."

She came closer, and as she did I got a better view of her bare legs and where her t-shirt pulled tight across her chest. She must have purposefully chosen a shirt that was slightly too small for her.

"So, what do you want to do?" I asked.

"I don't know." She walked right up to me, hands clasped behind her back and an innocent look on her face. "What do you want to do to me?"

To. Not with, but to. The implication of her choice in words sent a small shiver down my back.

"Kylie...."

"Or do you just want me to take care of you? I know you'd have trouble sleeping if I don't and I've been teasing you all day."

Her hands went to my shoulders and I let her push me back onto my bed. She might have been acting as though I was in charge, but there was no question it was her game.

Kylie reached climbed on top of me as I lay back, straddling my legs just above my knees. She reached for the waistband of my boxers, though she didn't try to remove them. Her hands strayed tantalizingly close to my cock without actually touching it.

"It felt good when you did it last night," I said, not directly answering. "I'd...."

"You want me to do it again?" she whispered.

I nodded and Kylie started to pull down my boxers. I made no move to stop her and soon my semi-hard cock popped free. Her eyes opened a little wider and she chewed on her lip hesitantly even as she wrapped her fingers around my shaft.

It was a sudden and somewhat unexpected way for my sister to see my cock for the first time, but the way she stared at it while it grew to full size helped to settle any doubts I may have had. She seemed fascinated by it and the way she stroked me reflected that. The whole situation was far more intense than it had been when we were both partly covered up.

Kylie's lips were parted slightly and she had a glazed look in her eyes. Her hips rocked gently as she kept jerking me off, her pussy seeking stimulation of its own and finding none. I reached out impulsively to grab her butt in both hands and dragged her forward. She squeaked in surprise, then sucked in a sharp breath as her panty-covered crotch pressed against my cock.

For a long moment we stared at each other and I worried that maybe I'd finally managed to push things past where Kylie was comfortable. It might simply have been the shock of my action rather than anything more serious however since she slowly resumed rocking her hips and consequently grinding her pussy against my erection. Only the thin material of her panties separated us.

"Jason..." she breathed.

"What? What is it?"

Kylie shook her head, deciding against saying whatever it was. She had leaned forward to brace herself on her arms and her breasts were so close to my face. I wanted to pull her shirt off and moved my hands to her lower back, preparing to work up to it.

All of a sudden she stopped, backing off just enough that I could no longer feel her against my cock. I was pretty sure she hadn't cum already, but she didn't look like she'd had a change of heart about the whole thing either.

"Ky, what's wrong?"

"Nothing, nothing's wrong at all. But it makes me want more and I need to stop now before I do something we'll regret later. We agreed sex was too far."

"Yeah, we did. I understand."

I was disappointed and didn't try to hide it. We were both feeling more or less the same range of emotions and arguing over it wasn't going accomplish anything. It was pretty obvious from Kylie's face that she didn't want to stop any more than I did, but if she felt like she couldn't control herself the last thing I wanted to do was push her into something she'd hate herself for.

"We could do something else," I suggested. "Something with not as much touching."

Kylie still hadn't moved, seeming reluctant to get off of me even though I would have thought a little space would help with her conflicting thoughts.

"This might sound stupid," she said slowly. "And I know I'm not thinking as clearly as I should be but...." She looked directly into my eyes, working up the nerve for whatever she was about to say. "What if you put it in my butt?"

The words were so quiet, but I could tell she was deadly serious.

"Um, are you sure you'd want that?"

"I know it's still pretty bad, but it's not as bad right? What if we just tried it once and then pretended it never happened?"

"Kylie, if we actually do it we have to do it knowing it's not going to go away. I'm not going to be able to forget it if we...." I swallowed hard. "If we fuck."

That's what it would be I realized. It might not be normal sex, but it would still be sex.

"You're right, maybe we shouldn't," Kylie said.

"I didn't say that, just that if we do we can't ignore what it means. And I honestly have no idea what it would mean."

"It means we're horny and stupid. I know I am right now." Kylie forced a small, humourless laugh, then looked at me critically. "Do you want to do it?"

There it was, the question I was trying not to think about while I was helping Kylie with her own mental struggles. Obviously it was exactly the sort of thing I shouldn't dream of doing with my baby sister, yet here I was considering it.

"I don't want to do anything that might hurt you," I said, not committing to anything. "Especially something that's only going to hurt later when it's too late to change what we already did."

"That didn't sound like a no." Despite the tension Kylie had the beginning of a genuine smile forming on her face. "You really do want to don't you?"

"Yes. But that still doesn't mean we should."

"No, it doesn't. We need to figure this out or we'll be here all night."

"We could always leave it for tomorrow and stick with something less potentially traumatic tonight."

"Maybe that would be best," Kylie said with a sigh.

Neither of us really wanted to wait, but we also couldn't come up with a way to dispel all the fears of what could go wrong. Or a definitive reason why we should give up permanently for that matter.

"Actually, I don't know if I can let this drop just like that," Kylie said after a moment. "Pick a number between one and ten, but don't tell me."

"Really? Kylie we can't decide something like this by luck."

"I know, I know. But look, I'll only have a one in ten chance of getting it right. If I don't get it then I won't even mention it again until tomorrow."

"I still don't think-"

"Come one Jase, you and I both know we could go either way here. I don't think you'd really be all that upset even if I do win."

"That's not the point," I muttered. "But fine, whatever. Take your guess."

Despite my protests, I wasn't entirely opposed to Kylie's plan. Sure the odds were on the side of nothing happening, but I found myself hoping that she'd guess correctly. I picked three and waited for her choice.

"Five," Kylie said.

And that was the end of that. I was about to tell her which number it actually was when I paused just for a second. It was completely within my power to say any number I wanted, it's not like it was written down anywhere. Kylie was watching me expectantly and as I looked at her I realized that this guessing game meant more than a coin flip. This wasn't a decision where the end result didn't really matter, the very fact that we were taking the chance said enough all on its own.

"Yeah, it was five," I found myself saying.

Kylie smiled knowingly and leaned in closer to me.

"Liar," she said.

I was pretty sure I'd never had a girl, or anyone for that matter, look so happy while they called me on my bullshit. It did give me the distinct impression that I'd deciphered her motivations correctly though.

"Maybe. You'll never know."

"I suppose you're right, but I can live with that." She stood up and started walking back to her room. "Wait here, I'll be right back."

"Uh, okay."

I felt eerily calm as I waited for Kylie to return. I didn't know precisely what I should be feeling, but it should have been something. It must have been a case of some part of my brain not registering what was going to happen, that I was going to have sex with my little sister. That was the sort of thing there might not be an instinctive reaction for since, really, how often was it going to come up?

I stripped off my boxers while I was just sitting there since they weren't covering anything anyway. Before I started wondering too much about what Kylie was doing she came back with something clutched in her hand.

"Lube," she explained as she saw me looking. "It might help."

"Oh yeah, never even thought of that." I frowned slightly. "Did you bring that with you from home?"

"Yes, but I never intended to use it with anybody. It was mostly for if I got too bored and needed something to amuse me for a while."

My mind slowly processed the information, able to some up with only one possibility for what she was alluding to.

"You mean you brought... toys?"

"Uh huh. I might even let you see them if you ask nicely."

Kylie bounced onto the bed beside me and we lapsed into a brief awkward silence. All those times in the past couple days when I'd wanted to see my sister without clothes on, now it was going to happen.

"You'll probably need to take your panties," I said eventually. "You could take off your shirt too if you want, you don't have to though."

She nodded and pulled her shirt up her tummy, looking a little shy as it passed over her breasts and finally off. I gave her a reassuring smile even while I tried not to stare too blatantly at her chest. As far as I was concerned she had nothing to be embarrassed about. They may not have been the biggest breasts in the world, but they were nicely round and firm, fitting perfectly on her body.

"And your panties," I prodded.

"Could you... could you do them for me?" she asked.

Why that was easier for her I didn't know, but I was happy to help if that's what she wanted. I knelt down in front of her and took hold of her panties on either side between my fingers. Kylie raised her butt as I pulled them down and allowed me to drag them all the way off her feet.

When I looked back up I was staring directly at the most beautiful bare pussy I had ever seen. It seemed so tiny and delicate, almost cute. I was somewhat confused however by the lack of any hair.

"I had to shave it all," Kylie said as though she could read my mind. "With that bikini I was wearing, it didn't hide much."

"Well it's beautiful," I assured her. "Just like the rest of you."

Kylie blushed and I almost felt like I should apologize for the compliment that had slipped out naturally.

"Thanks," she said in a soft voice.

We were both naked and on my bed, but now it seemed that neither one of us knew what to do next. Or more to the point, we were reluctant to take the lead.

"So, I guess we should do this," I said at last, hoping to goad Kylie into action. "Or at least start getting you ready. I don't think it's going to be easy for you to relax, but you're going to need to."

"I've actually been working on that already."

My confusion must have been obvious because Kylie gave me a crooked smile and started to roll over. She looked back at me like she was going to say something else, then decided not to and finished repositioning herself. With my sister now lying on her stomach it became clear what she had been hinting at.

"One of your toys?" I said.

I put one hand on her butt to gently spread her cheeks and get a better view. Right in the middle, protruding somewhat obscenely from her ass was the rubbery end of what looked like a butt plug.

"One of my toys," she confirmed. "I put it in earlier, should make sex a little easier."

"How much earlier? Like before you came in here?"

"Oh, earlier than that. I like wearing it around you when you have no clue, feels kinda sexy. And dirty."

"You're bad, little sister." I shook my head, though really I agreed that it was pretty hot. "Was it just tonight, or did you do it to me other times too."

"That first day in the car, when I was bored out of my skull, that was the first time I ever did it when I was around someone. Maybe that's why I was thinking about sex so much. Then I put it in again the next day too and, well, we ended up here."

"We did, didn't we."

It occurred to me belatedly that I was still fondling Kylie's butt, and also that I had no interest in stopping. Everything about her was conspiring to drive me crazy and with each passing moment I grew more certain that I wanted to do this.

"I guess I should take it out," I said.

"That would help. Gonna be hard to stick anything else in there otherwise."

Kylie's tone was teasing, but I sensed the same nervous anticipation in her as in me. I tentatively took hold of the flared base of her butt plug and pulled on it. It moved only reluctantly at first, stretching her wider until suddenly we were past the largest part and the whole thing popped out.

I noted that the plug wasn't as big as I expected, no doubt because porn gave me a skewed perspective on what size girls tended to use, but otherwise ignored it and set it aside. I was much more interested in my sister. Her hole hadn't quite closed after having her toy in there for so long and I knew there was no point waiting since her ass was about as relaxed as we could hope for.

"Make sure you use lots of lube," Kylie said, not looking back at me but spreading her legs a little more in invitation.

"Don't worry, I know that part."

I took the lube and squirted a good amount right over her asshole. She jumped slightly at the unexpected sensation, but seemed to like it when I started to spread it around with my fingers. I had intended to start pressing gently against her hole and let it accept me at its own pace, but I underestimated how much of an effect her preparation had and I was able to slide my finger in almost immediately.

Kylie moaned in pleasure as I moved my finger back and forth in small motions. Her butt actually started rocking in time with me and I was tempted to just sit there and finger-fuck her for a while. I was far too horny for that though and I needed some stimulation of my own.

"Are you ready?" I asked.

"Uh-huh, do it Jase. God I want it so bad."

I had removed my finger and was applying lube to my cock just to be sure there was enough when Kylie raised her lower half up onto her knees. The wanton display of my sister sticking her ass up at me and wiggling it impatiently was just too much and even if she had second thoughts at that point I might not have been able to stop.

I knelt behind Kylie, urging her a little farther into the middle of the bed to give me room, and pressed the head of my erection against her butt where my finger had so recently vacated. My cock was significantly bigger however, and the ease I'd had before was replaced a barrier that didn't quite want to let me in.

"Shit, you're bigger than anything I've tried before," Kylie said.

"Just relax."

"I'm trying. It's not easy when my brother's about to fuck me."

Her statement sent made my already rock-hard cock twitch and I began to worry that at the rate we were going I was going to cum before I even got inside her.

"Actually you're going to be the first guy to get me back there," Kylie said thoughtfully. "Kind of a weird... holy fuck!"

The very tip of my cock had made it past her outer ring and I froze instantly as I heard the pain in her voice.

"Sorry, do you want me to pull out?"

"No, stay there just... fuck that kind of hurts. I think I tightened back up as soon as you got in. I got too excited."

She was probably right, the way she was squeezing me I couldn't imagine how I could possibly have made it inside. If my whole shaft had been in I might have well have cum simply from how tight it was. As it was the mental concentration involved in forcing myself not to move was enough to calm me down a little.

"Just relax," I said.

"I'm trying, it's not easy you know."

"I know."

I leaned down into a position that wasn't great for sex, but put my face right at the top of Kylie's back. Mainly I wanted to help, though the smooth skin just below her neck was inviting enough that my motivations were not entirely selfless. I placed soft kisses between her shoulder blades and gradually explored farther away from my chosen centre point.

"That's kind of nice," Kylie told me.

"Glad you like it."

It seemed to be working too, before long her ass once again relaxed enough that I could move without hurting her. I waited a little longer just to make sure until she gave me a signal that she felt the same.

"Okay, I think I'm good now," she said a moment later. "But go slow."

"Trust me, I will."

I had used more than enough lube and once Kylie's body was ready to accept me moving inside her wasn't as difficult as it could have been considering anal sex was so new to her. Her practice with her toys had paid off in that respect at least.

Using only very small back and forth thrusts I penetrated deeper into my sister's ass until she started rocking back against me. Once she began responding like that I felt more confident that she truly was enjoying herself more than she was in pain. I had no illusions that it wouldn't still hurt at least a little, but given time she might be able to move beyond that.

When I finally bottomed out I stopped and held myself there for a moment. It was so incredible to think that Kylie and I were naked with my cock fully buried in her ass. Of all the moments in my life important enough to remember years later, I knew this was going to hit pretty damn near the top of the list.