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****
It was nice living on my own. It meant a certain amount of freedom and independence that I'd never experienced while I was growing up. I didn't end up getting a big apartment, or even one that was particularly far from home, but it was mine.
Of course, what with being barely a fifteen minute drive away from my family, I still saw them on a semi-regular basis. I'd go home for dinner ever now and then, or someone would stop in on their way somewhere else. My little sister Anna tended to come by more often than my parents. Mostly it was out of convenience, since my apartment was close to a fair number of places, including her school, and she didn't have a car of her own. If she wanted to go anywhere farther than she could walk, she generally had to either get a ride from someone or take the bus. She wasn't much a fan of the bus.
Anna had a habit of showing up whenever she felt like it. It was to the point where I was pretty sure the spare key I'd left with mom was essentially my sister's property by now. I'd gotten used to returning after work to find her casually lounging around on my couch or microwaving herself some food before she headed back out with her friends.
Her lack of predictability meant that it didn't surprise me in the slightest when she showed up one day out of the blue. She simply walked in and kicked off her sneakers before greeting me.
"Hey Ryan," she said. She dropped a plastic bag on the counter. "Mom sent you some stuff."
"Hey," I said back before moving to check out the bag.
I was pretty sure it'd be food. It usually was. Mom still hadn't gotten used to not having a teenage boy around to feed, and consequently made far bigger meals than she, dad, and Anna could eat. I got sent a lot of leftovers, which worked out just fine as far as I was concerned. The fact that Anna made deliveries every now and then sort of made up for her frequently raiding my fridge.
"So what are you up to?" I asked after having satisfied that the bag did, in fact, contain leftovers in Tupperware containers.
"Going out with some friends," she said. "I'm getting picked up here in... about five or ten minutes I guess. I'll get a text when they're close. Speaking of which, can I borrow twenty bucks?"
"No," I said flatly.
I knew how my sister's 'borrowing' went.
"Come on, I'll pay it back."
"Doubtful. If you do it'll just be because you con some money out of dad when you tell him I need to be reimbursed. And even if he falls for it there's still only a small chance I'd ever see the money. Shoulda just got the money from dad to begin with."
Anna shrugged. "I forgot to this morning. You wouldn't make me beg money off my friends, would you?"
"Absolutely I would. You're eighteen. You practically deserve that kind of embarrassment if you're still as financially hopeless as you are."
She stuck her tongue out at me, then sighed.
"You're kind of a meanie sometimes, you know that?"
"That's not how I'd put it. I'm trying to teach you some responsibility is all. That and I can't afford to toss money at you every time you think you need some. That's what dad's for. He hasn't learned his lesson yet."
Anna smiled a little and I couldn't help smiling too. It was a bit of a running joke between us how easily she could make dad cave on just about anything. Sure it was annoying sometimes how much he spoiled her, but to be fair she'd used her power to help me out more than once. She might have been spoiled, but at least she wasn't a brat. Well, not too much of one anyway.
"What if I trade you something for it?" she asked.
"That might work, if I thought you had anything I wanted."
She thought for a moment and occasionally glanced down at herself as though looking for inspiration. Obviously I didn't want any of her clothing or earrings or anything. Her phone was the only thing that might have some real value to me, but I knew she wouldn't give that up over twenty dollars.
"Maybe I could do something for you," she suggested.
"Like what? I mean, I have chores I could get you to do that'd be worth twenty to me, but they'd take longer to do than you have. It'd need to be something you can do in ten minutes, give or take. Face it, you're out of luck."
A look of resolve crossed her face. I tried not to show any sign of amusement, but I knew I'd pushed her buttons just right. She hated being told there was nothing she could to change a decision she didn't like. If I didn't want an argument I would have to be more delicate in saying no. In this case I was okay with it if she wanted to fight. She had to leave soon anyway.
Anna looked me dead in the eyes. I wasn't sure what she was going to say, but I was prepared for just about anything. I'd heard just about every ploy she had over the years. Somehow, she managed to surprise me with a new one.
"I could give you a blowjob," she said.
My mouth dropped open stupidly, and I couldn't form an immediate response. I assumed I'd heard wrong and tried to reprocess her words, but I'd heard right the first time.
"What?" I said.
"You heard me. That's something I could trade that would take less than ten minutes."
"Yeah, but--"
"So will you give me the money or not?"
I shook my head silently, then grabbed my wallet and pulled out a ten and a five. I needed to hit an atm soon, that was the last of my cash.
"Fifteen," I said. "That's all I have. And you better understand this nonsense isn't going to work again."
Anna shrugged. "Deal."
She took the money and shortly after she got a text from one of her friends. She wouldn't have had time for a blowjob after all, not that she ever intended to really go through with it. At least, I didn't think she would have done it. Probably.
For the rest of the evening I couldn't help wondering in the back of my head what she would have done if I had called her bluff.
****
The next time I saw my sister was on the weekend. I was going to my parents' house for supper, and ended up getting assigned to pick Anna up from a friend's house on the way. I'd mostly forgotten the whole 'blowjob' thing at that point.
I pulled into the driveway at the address she'd given me and sent her a quick text to let her know I was there. I could have gone in, and maybe it would have been faster, but she actually didn't take all that long coming out to meet me. I'd driven off without her one time when she took too long. She'd been cautious about messing with me when I was giving her a ride ever since then.
We exchanged greetings and Anna put on her seat belt as I pulled back onto the road. Partway into the trip she dug into her pocket and handed me a pair of bills.
"Here's your money back," she said.
I snuck a quick look at her, but she was showing no indication that it was a trick.
"Thanks," I said, looking at the money just long enough to confirm it was indeed fifteen dollars just like I'd given her.
"Didn't expect that, did you?"
"No, I honestly didn't. Dad?"
"Dad."
I nodded, satisfied that the world was still running more or less as it should. Getting paid back by my sister was uncommon, but not unheard of.
"As long as you're not actually giving blowjobs for money, I guess it's all good," I said.
"You don't think I'd really do that, do you?"
Anna didn't sound offended, but she could be masking it. Mostly she sounded genuinely curious. I wasn't sure why I'd thought it was a good idea to bring the subject back up.
"No, I don't think you would. I was pretty sure it was just a way for you to scam me."
"Wasn't a scam. I would have done something for you. Just like I said I would. I only gave that example 'cause you were being difficult. It wouldn't have been my first choice."
I frowned and tried to keep my eyes on the road. I kind of wished I wasn't driving so I could watch my sister more closely as we talked. It was hard to figure out what game she was playing.
"So you might have sucked me off," I said slowly. "If we had agreed on it and everything. Is that what you're saying?"
"You did something for me, I would have done something for you. That's all. I think you're reading too much into this."
"Okay, maybe I am. But ignoring that issue for the moment... there's no way you'd actually do it. Like, there's no way."
Anna's eyes flashed in that same determined way they had last time we'd discussed the issue.
"Try me," she said.
Fortunately I was saved from having to figure out how to respond by finally reaching our parents' house. Anna didn't try to force any further conversation before we got out of my car, and I doubted she'd bring it up while there was a chance mom or dad might hear. She might have been stubborn, but she wasn't stupid.
****
I stuck around for a while after supper. I didn't want it to look like I specifically wanted to talk to Anna, so when she vanished into her room I waited a while before following her. She didn't have her door closed, so I didn't even have to knock before walking in. She could see the doorway from where she was anyway, so it wasn't like I was sneaking up on her.
She was lying on her bed with one of her school books in front of her. The book was undoubtedly part of a pretense that she was doing homework or something. Every now and then our parents tried to take an interest in her studies. It never lasted long, nor was it ever all that effective.
Anna also had music playing and was busy texting on her phone when I found her. I suspected if one of our parents had walked by the phone wouldn't have been anywhere they could see it. I wasn't sure how she'd known it was me, unless she was really good at distinguishing footsteps, which was possible.
"What's up?" she asked. "Thought you woulda left by now."
"Yeah, I stuck around a little longer than usual. I kinda feel like we needed to talk more."
"What about?"
I rolled my eyes at her feigned ignorance. She knew what I meant. I checked the hallway just to be sure we were alone, then closed the door.
"Look, I don't know what--"
"Are you gonna ask for a blowjob?" Anna interrupted.
"Um, no. That was not what I was getting at."
"Okay. So what's the problem then?"
"You know, you're being incredibly frustrating."
Anna grinned. "Thanks."
"Whatever. I tried. If you've got issues, you'll just have to work them out with someone else. Or repress them. Your choice."
I left feeling slightly annoyed, and I wasn't entirely sure why. I wasn't even certain what I'd hoped to accomplish. Anna was messing with my head, that was all. I should have known better than to let her get to me.
****
That was the end of any inappropriate discussions between me and my sister for a while. She still showed up at my place sometimes, and I still gave her the occasional ride, and that was about it. Not a single one of our conversations gave me any cause for concern. Life was normal, if only temporarily.
I came home one evening to find Anna sprawled across my couch watching Netflix. Mom and dad didn't have it, so she'd occasionally come watch some stuff at my place, particularly if she just needed to kill some time before going out again.
"Hey, little sis," I said. "What'd you make me for supper?"
I lifted her legs and sat down, letting her legs come back down to rest across my lap. She only spared me a brief glance during the whole process.
"Brought some leftovers that mom sent. I can heat something up out of that if you really want."
"Nah, don't worry about it. You're probably headed out soon anyway, right?"
She shrugged. "Got no plans. Things got canceled."
"Oh."
It wasn't like Anna went out every night, even if it felt that way at times. I usually found it safe enough to plan on her not sticking around too long.
"Did you already eat?" I asked.
"It's not even six yet."
"I was just asking. I didn't know if you were staying for supper or what. You haven't really told me anything, you know?"
I punctuated my point by raking a fingernail over the bottom of her foot. She squeaked indignantly and pulled her foot away from my hand.
"Well I might stay, if you're not gonna be too much of a meanie. It probably is just gonna be heated up leftovers though, isn't it?"
"Maybe. That'd be easiest."
"Do you at least have any ice cream or something?"
"I might be able to hook you up. What's in it for me?"
I regretted the question as soon as I said it. I wasn't even sure where it had come from. By the time I remembered what had happened last time we'd been in a similar situation, it was too late.
Anna gave me an amused look. She pulled herself up into a sitting position, crossing her legs and not quite facing me directly.
"Are you looking for something in particular?" she asked.
"Sorry, I didn't mean it like that. I just... dammit, I don't even know. There's some ice cream in the freezer if you want some. Whatever."
"Ryan, don't get all embarrassed on me. What are you so worried about?"
"Nothing. Just thinking about, you know, that conversation we had."
"I know, me too. I thought that was obvious."
"Come on, Anna. You wouldn't do it, we both know that. I'm sorry I keep bringing it up. I don't even know why."
Actually, not that I'd admit it, but what I really didn't understand is why I was practically daring her to prove me wrong. I'd done it before, and I was doing it again. Even if it had been a bluff all along, as it had to have been, challenging her so directly could go very badly.
"So ask," she said in a low, dangerous voice. "Prove me wrong."
She stared at me intently, her body seemingly relaxed even though I could tell she as tense as I was. My next words would be important and should have been chosen carefully. However, I wasn't thinking straight enough for a moment of such magnitude.
"Fine," I said, staring right back at he. "Give me a blowjob."
Anna didn't so much as blink.
"Ask nicely."
"Please give me a blowjob."
Our eyes remained locked on each other for another second or two, then abruptly my sister unfolded her legs and hopped off the couch. She knelt on the floor between my feet and reached toward my waist. As I watched in stunned silence she undid my belt, then paused.
"Stand up for a sec," she said.
I did as she asked, waiting for her to give. I was hoping she was just waiting for me to chicken out first, and I had to play along until she did. Her nimble fingers had my pants undone and pulled down to my ankles in short order, leaving only my boxers between her and my cock.
Embarrassingly, I was starting to get hard. It was only a reaction to the situation, I told myself. Obviously my body couldn't be expected to recognize that the girl kneeling in front of me was my little sister. It was only doing what it was designed for. Still, it was awkward as hell to be getting an erection in front of Anna like that. I hoped she'd surrender soon and admit that she wouldn't go through with it.
Unfortunately she was showing no sign of giving in. I felt her tugging on my boxers and, as if in slow motion, they began to slide down my legs. If I'd thought getting an erection as bad before, now it was worse. There was nothing left to cover it and it just kept getting harder.
"You can sit down now," Anna said.
I followed instruction numbly and sat back on the couch. I scooted my butt closer to the edge without really knowing why I would do that. It wasn't like I had any intention of actively facilitating the situation. All I needed to do was wait until she admitted defeat, despite how I was beginning to worry that it wouldn't happen.
Anna leaned in closer, close enough that I could feel her warm breath on my cock. I had to close my eyes to avoid freaking out. There was no way I could be letting this happen, but it couldn't be a dream or anything either. It was way too real.
My sister's fingers brushed my shaft, just barely making contact, but it was still enough to make me flinch. I opened my eyes again to find that she was staring fixedly at my nearly-full erection. Her fingers traced its length a few times before wrapping around it in a light grip. I hated that it felt amazing.
"You're really doing this," I said.
"Told you. You should know better than to doubt me."
She smiled up at me, just the slightest hint of smugness evident in her face. I hadn't noticed before, but from the way she was leaning toward me I could kind of see down her shirt. I'd known my sister had boobs, but it had always been the sort of thing I knew on a distant, intellectual level. For possibly the first time ever I was forced into the realization that she had some genuinely attractive qualities, physically speaking. They weren't all canceled out by virtue of her being my sister.
Her hand stroked my cock slowly, giving me plenty of time to adjust to the feeling. I still had the chance to stop everything before it went any further, if I wanted to. The problem was that I didn't know if there was any reason to at that point. She was already jerking me off, it wasn't like it could get much worse. Plus, if I was being honest, I wasn't sure I wanted to stop it.
"That... actually kind of feels nice," I said.
"Good. It's supposed to."
I tried to relax and just enjoy the situation. Morally speaking it was pretty bad, but otherwise... well, it could have been much worse. It hadn't been a lie when I told Anna that what she was doing felt good. I was just starting to settle into the handjob I was getting when my sister moved her mouth closer to my cock. Somehow I'd forgotten that I was actually meant to be getting a blowjob. She had obviously remembered.
Anna's tongue flicked out and licked from halfway up my shaft to the very tip. She did the same thing a couple more times, watching my reaction closely. I was too overwhelmed and confused to give her much of one, but she seemed satisfied.
With agonizing care, she slowly engulfed the tip of my cock between her lips. It seemed so crazy that my little sister had actually taken me in her mouth, and yet at the same not so crazy. For whatever reason, as she took me deeper and deeper it all began to feel right. Logically I knew the moral issues hadn't gone away, but it no longer felt wrong. It just felt good.
I put a hand on the back of Anna's head. I didn't try to force her, or even guide her, it was just to tell her I liked what she was doing. She didn't so much as hesitate or look up at me, but I could have sworn she smiled, just for a second. Granted, it was hard to tell when her mouth was otherwise occupied.
Anna bobbed her head on my cock for a while, working me deeper until I could feel the back of her throat. Her tongue moved around my shaft more or less at random, and sometimes she'd hold her head still for a moment and just lick me. Other times she pulled her head back until only an inch or two was still in her mouth and jerk me off a little with her hand. It seemed kind of like she was experimenting and trying to figure out what worked best. Whatever the case, she was getting results.
My little sister was going to make me cum. It was just one more unbelievable realization on top of all the others. There was no way I could resist, and in fact I didn't even want to resist. Her fingers, her lips, her tongue, they were all making me feel way too good.
"Fuuuck," I breathed as I felt my orgasm building.
Anna took her mouth off of my cock just for a moment, taking over with her hand as she did.
"Are you close?" she asked.
I nodded and had to fight the urge to push her back into position. I needed her warm, wet mouth on me in way that was far too scary for my liking. She shouldn't have been able to take control of me to that extent. Although, seeing as how I was on the verge of cumming, it probably wasn't all that significant. I wasn't fully in command of my body at that point.