Disclaimer: I don't own Oreimo, its characters, or any of its related properties. In fact, if I did, I'd probably be...however wealthy the author and publishers happen to be.

Additional information: This story is in something of a no-man's-land chronology wise, as I've seen the entire anime but have read only a bit of the light novels. So try to think of this as alternate timeline of sorts. Enjoy!


It was on that day, as I walked home to an inevitable torture session of "life counseling", that I realized that there was not one path, as many people believe, but a variety of choices open to me. This kind of thinking suits me well, as I'm not exactly a decisive person—unless it's a matter of "normalness" or "ordinaryness" versus something more complicated.

"Eh? What are you thinking so hard about?" a squeaky voiced barked out.

Can't you be more quiet? Kirino, my younger sister, an all around sophisticated person to the civilized world at large, really sounds this bratty. She's the kind of person that's easily provoked, someone who always manages to make you feel like you're the nuisance.


She exhaled, obviously unsatisfied with my answer. Then she flicked her head abruptly to the side.

"Ugh, I don't even want to know."

It's true, you don't.

We sat down in her room. The vibe of this place is both welcoming and intimidating. On one hand, it's very familiar in a nostalgic kind of way, in the way you expect a sibling's room to appear because of television and the like. On the other hand, the air about my sister is always so impatient, so full of invisible standards that I'm constantly failing to meet that it kind of makes me cringe to exist within her presence. Ugh.

Despite this, I carry on with her. In fact, it kind of unsettles me to think about it, but truthfully, it's exciting to be a part of my sister's chaotic life right now. There's a lot of fun and interesting peopl...eh, I can't believe I'm saying this so explicitly. Okay, what I mean by "people" is, obviously, girls, of course. What else, for guy my age? It's shameless to say, really. You see, I'm not at all a charismatic person, and I'm slightly-above-average looking at best. So why am I so excited? Why am I acting as if someone like me could have a shot at anything with a cute face, you ask? Well. Somehow, I seem to have a flare for saying the right thing at the right time—even when it isn't exactly the"right thing". If that doesn't make sense, let me explain. Sometimes, while it seems counter-intuitive, you have to say a wrong thing to provoke the right kind of response. And then the right kind of response gets you further along to where you want to be. Heh, putting something like that together. I'm something, aren't I?

"Pay attention, you!"


I sat upright, awaiting yet another round of bothersome chitchat.

"What do you think of this?" she said, passing me her laptop. Cross-legged, and closing her eyes, she scratched her chin a sagely fashion. "For once I think I've made a bad purchase."

"What's this?" I said on cue.

She reached forward.

"Here's the game case, too."

In my lap was the empty case. I stared at the cover had a pink and gold intertwined trim, playfully meeting at the 18+ sticker in the upper-right corner. The ceiling lamp was reflected in cheap holofoil around the title: Sister-Caught Trouble: Untrustworthy are Feelings. What else? A small girl with short curly brown hair was dead-center, nestled by a mound of pillows on her powder blue bed. She wore polka dot pajamas that matched the blue of her sheets. She winked, smiling innocently. Looking closer, her small hands were bound together with bubbly handcuffs. Ah, what else is new? By now I had a somewhat intermediate eye for these titles (whether that is praiseworthy or pathetic is not something I'd like to think about), so with a passing glance and without much dissection I can kind of guess the content of a simply, for the kind of eroge that my sister likes, this would be standard fare. But...what's this? On the spine of the DVD box was an ominous crack in the doorway leading into the girl's room. From the black abyss of the hallway emerged a creepy figure, outlined only by his gleaming eyeglasses.

"Oi, oi...this title... Isn't this kind of rapey?"

She nodded, quickly.

"It's okay to take advantage of the little sisters in some eroge, but this one is a little too much."

Indeed, this wasn't the kind of eroge that Kirino enjoyed. Other things got her off (eh, I can't believe I'm saying it like that...).She loved how cute the sisters were. She loved the thrill of little sisters fawning over her, their older oniisan. And while some route choices were more...forceful...than others, they usually presented laughably consensual situations.

I looked at Kirino and saw a rare disturbance in her face, different from the kind of disgust she usually telegraphs to me. Feeling likewise, and not knowing what to say, I managed an alright response.

"Are there...how do I put this? More 'gentle' options?"

She sighed.

"It's frustrating, I've gone through nearly 75% of the routes so far, but they all end forcefully! Rape, rape, rape, and more rape!" She threw her hands up toward the ceiling. "Where's the love, the passion, the intensity? These creators have no respect for little sisters!"

Huh? You think that these games are in any way "respectful"!?

"You. Play through for a little bit," she said, more directing me than awaiting my agreement.

Selecting the pink and gold shortcut on the desktop, I booted the game up. It was truly a disgusting title. But as I played through, uncomfortable as I was, my mind wandered to other pursuits. A spinning menagerie of all my sister's friends seemed to fill my thoughts. A smile here, a glance here...am I reading into things too much? After all, a guy like me who has no experience with dating couldn't possible read such "signs" accurately. All of my sister's friends are, thankfully, pretty good looking. They aren't gross at all, especially my lovely Ayase-tan. And I wonder what the tall one looks like without the silly glasses and the gross, outdated t-shirt? "Fujiwara Norika", she said, eh? Hehe, not bad at all. Kuroneko, too, is a little on the weird side. But... she really is quite cute. If she could coordinate such a complicated cosplay outfit, I can only imagine her if she toned it down a bit...

"Hey! Why the hell do you look like that?"

"Huh, I'm...very disgusted! Yeah!"

"Liar! Look at you, you're almost drooling!Don't tell me that, of all things, this is what you like!? After all the dozens of little sister masterpieces I've let you borrow? I should have known someone like you would go for the hurtcore stuff!"

This girl...!

"Hey, hey, no...I... Don't get the wrong idea! I'm not..."


I was seriously confused, and without the strength to properly defend myself. My mind was in three different places: Kirino's room, this Sister-Caught title, the otaku girls, the heavenly Ayase. Ahhh.

"I'm not. Besides, have you ever seen your face when you play some of this stuff?" was all I managed to spit out.

"Hmph." She crossed her arms. "That's differen't. An uncultured person like you wouldn't understand."

Culture? This is sub-culture! No, sub-sub-culture! I gave up, and returned to game.

Please oniisan, I don't want to play anymore! Please!

Such a horrible dialogue emerged from the tinny laptop speakers. "Me, too," is what I wanted to say.

"K-Kirino, I'm turning this off!"

I alt-F4'ed and closed the clamshell.

Biting her lip, Kirino said nothing.

Today's life counseling was abruptly cut short.

I walked the handful of paces to my room, entered and shut the door, heaving a heavy sigh of relief as I collapsed against it. In my hands I sheepishly clutched Sister-Caught Trouble.

Get rid of this, it's a disgrace to the entire imouto genre! Toss it, burn it, send it into space - I don't care how, I just never want to see such trash ever again.

And with that, that was the mission I had been tasked with.

Such a hassle, truly.

I tossed the box to the side and tossed myself onto my bed. Here too, my thoughts carried on endlessly.

For a moment flashed the deliberately solemn and not-so-deliberately shy Kuroneko. She appeared before me, gazing at me by my bedside. She was kneeling, prostrating, begging me to... what's this?

Undress me, Kyousuke-sama.

Ho, ho! I didn't know her all too well, but this was the kind of obedient language my naive yet perverted mind had generated. Awesome!

A mosquito landed on my leg, which I spastically slapped off. Ah, you bastard, interrupting my thoughts? I laid back down. It was quiet again. There wasn't a sound from my sister's room. No eroge for you, huh? That title must really have left a bad taste in your mouth.

Above me was the blank ceiling. Feeling bored and very restless, I returned to my thoughts.

But, oniisan, you pervert, y-you're too much. You're so close to me...it's hard to breathe...

Ayase-tan, now. Ah, but it'll never be, right?

I rolled about, left to right like a rotating sausage.

Kyousuke-shi...no, my Kyousuke. I've never showed this side to anyone.

Saori, too?


Feeling silly, I opened my eyes with a subtle shake of my head.

The soft light of the moon was cut off to the side, highlighting the uniform floorboards of my exceedingly average room. My head was cocked to the side. I felt my eyes droop a bit, mindlessness settling into my skull as I traced the many paths of floating dust before my window.

If I had the skill, and you asked to me to pick one of these girls, I'd pick them all—and I'd pick more if there were more to pick. Really. I'm not too confident myself, but...I would love to experience them all. Every look, every touch, every would-be first kiss. Every first...heh.

Damnit, couldn't I have the kind of looks and charm that those kind of guys have?

I was so frustrated and equally aroused that I started to reach under my bed for a magazine. But instead, my feet sprang off the floor and I turned on the borrowed laptop, tapping my foot as the Windows logo stretched and separated. After it loaded I opened Firefox, searching for an answer. This led to an insomnia-driven two hour search through message boards and forums, which led to many PDF files and many questionable sites. Finally, I hit upon a mid-sized thread of around 60 posts: a heated discussion about the effectiveness of various seduction methods.

"P...U...A...?" I muttered to myself.

I should have known then by the embarrassing banners of busty women sprawled out in lingerie, links to synthetic marijuana and other "medicinal herbs", and by the pop-ups for various generic boner pills that this was the Internet analogue to a seedy red-light district.

Sticky-topics laid out in no-nonsense bullet-points provided newbies with the base lexicon of popular seduction concepts and technique.

Fanboys trumpeted their respective suave gurus claiming to transform desperate losers and geeks into sexual superstars. Each guru had a "look" or a gimmick: one wore sharp blazers with spiked hair and aviator glasses; another was bald with an earring and a soul patch; another yet was super-muscular with ridiculous tattoos of playing cards and flowers all across his arms. Geez. This kind of thing reminds me of a fighting game selection screen or something.

I scrolled down some more. Unintelligible memes bounced back and forth. Several members who qualified as having "one-itis" shared discouraging stories of heartbreak and denial. One "troll"—as a certain banned user was declared—advocated groping a woman almost instantly after greeting her (this would apparently activate her "primal response"...what?). "Pros" linked to the resources they felt most confident in helping to shape the "average frustrated chump" into a suave, masterful pick-up artist.

Although I was very embarrassed, it was exciting to read these posts. I inspected each new technique, drafting a mental imagine of the scenario unfolding. The "opening", the "escalation"...each step in the seduction process seemed so calculated yet so fluid. I could really do this! I think... I had to control myself though. More often than not, my "simulations" quickly degraded into blatant sexual fantasies. Which I didn't mind at all, really. Haha.

Smirking, I shook my head, and continued my studies.


I awoke, nearly scolded by the laptop. The damn thing had a faulty battery that never seemed to charge right. Geez. I should throw this fire-hazard out with that horrible eroge!

Wiping the dry drool off the corner of mouth, I fixed my eyes on the laptop screen. Banners and ads obscured whatever site I was on; I couldn't remember. I was grateful that school was still a few hours away, and that no one had come to wake me. Coming in without regard to my privacy, as the always do, they would have surely seen this unbelievably embarrassing screen.

My eyelids were dull and my neck was sore. My body was a bit achey but my mind was too stimulated to go back to sleep properly. Instead I threw on some loose clothes and went for a walk. I grabbed the DVD case, realizing that this would be a good opportunity to dispose of it without raising any suspicion. Not quite sneaking downstairs, I hit the fridge, got some juice, and left outside, closing the door with a criminally soft pull.

Outside the sun barely creaked above the horizon, holding far away from the bluish-purple swath of last night's sky. On one side of my house were dim stars; on the other, a light-blue stretch of sky and clouds.

I reached the trash and finally placed the eroge—wrapped in foil, brown paper, and thick black plastic—inside. I sighed...we'd better not get a ticket for that. Is that better Kirino? You couldn't do that yourself?

"You'd better do it properly now."


I turned around to see, of course (of course, of course!), my plain childhood friend in a dusty housecoat.

"Ah, good morning," I said, scrambling to place the trash can lid on right.

"Good morning!" said Manami. "What's Kyou-chan doing up so early this morning?"

Isn't that my line?

"Umm...well..." I tugged at my ear. "I decided to go for a walk, you see."

"Ohhh," she said.

Gah, am I always this unconvincing? It's a good thing she doesn't ask too many questions.

"I'm just taking a quick walk to the supermarket," I said. "I couldn't sleep."

She turned her head very slightly.

"Kyou-chan, you really need to watch yourself. It's not good to wear yourself out like that. Please try to go to bed earlier, okay?"

Geez, what are you, my mother? I guess she's right though...gah, did I even brush my teeth?

"Yeah, yeah. Well, what about you? Not that being outside early is such an usual thing, you know, but I don't really think of you as an 'early person', despite how much of an old lady you can be sometimes."

She giggled a bit. That wasn't even funny!

"I'm helping my grandparents clean the store, so I want to get as much done as I can before school. That way, I won't have as much to do later."

"Ah, that's just like you. I would have waited until the last minute. Speaking of which..." I looked at my cell phone and forced a concerned look. "Gah! Ha, ha. There's some homework I haven't done." Which actually was the truth, but history wasn't too difficult at all and I could finish it in about fifteen to twenty minutes.

"Kyou-chan, really? You know-"

I didn't need to hear the rest of this sentence to know its contents.

"Yeah, yeah. That's just my style, I guess. Well, I'd better head back. See ya."

"Goodbye, Kyou-chan," squeaked that ever-disappointed voice.

I was about to step away, but I did something of double take. Although her current clothes were quite frumpy, and her hair was as uninteresting as ever...well, can you believe, in this early morning light, that she managed to actually look somewhat pretty? In a vague way, of course... but still.

I sighed.

Now, this is hard to believe, but in that instant I did something incredibly insane. Or, rather, something insane was "done" to me. I felt a strange pull in my lower half (not that lower half!), a twitch in my calves, as if a demon had had a grab at my legs. My eyes watered and I gagged. Thousands of words flooded my vision, colors swirled in all directions as orchestral sounds and hundreds of languages scrolled past my ears and eyes. All at once: abstract pictures, cryptic diagrams, mathematical formulas—the ancient sun and all living things expanding and contracting to the pulse of the universe. I vibrated in a strange, strange manner, as if I was ready to dance and die at the same time. I thought I was going to puke.

Then, silence.

I exhaled—then shot a quick breath into my lungs. My legs...!

In that instant, I was pulled forward to within an inch of Manami's round face.


Actually, let me rewind for an instant.

Actually, never mind. This is too ridiculous for one of my usual cocksure explanations.

We were both beat red, both equally confused. I could see the tense and nervous sweat beads mixing with dust near her temples, her mouth soft and prize-like.


The usual dimwitted and equally pathetic kind of "explanation" for my odd behavior did not exit my mouth. Instead, those awkward sounds were replaced by a dialogue so captivating in it's emotional backdrop yet so painstakingly mundane that I honestly cannot remember it. What I do remember is what happened next.

I took my childhood friend by the shoulders powerfully but gently, and guided her lips to my own.


What is this feeling? Why do I feel so... So cool...! I feel like a damn rockstar! Or...I guess maybe one of those male drama idols, haha!

The kiss was over as soon as it began. In a truly insane move, I, Kyousuke Kousuke—average high-school ordinary guy extraordinaire—had kissed this girl!

Now before you get the wrong idea, let me state unequivocally that Manami isn't really the kind of girl I'm into. She wasn't exactly the best kisser (not that I have much experience, right?). However, it felt great. Plus, it's thanks to "practice girls" like these that a guy like me... heh... listen to this! "A guy like me", huh? But I'm getting a bit ahead of myself here. After all, this girl is quite plain, and, furthermore, she is putty in my hands most of the time. Too easy, right? Without a doubt it's too easy when the girl already likes you.

Recalling a bit of words from those message boards, my body translated these into real movements. I lifted my hands from her shoulders and said nothing. Then I looked into her eyes in an assuring manner—she was too cute in this instant—and made the about-face turn I had planned nearly two minutes ago.

She stood frozen.


I tapped the garbage can lid and walked at a slow pace back to my house, grinning like a maniac.

I opened the door softly, removed my shoes, and climbed the stairs to my room.

Heh heh.

Then I entered, and changed into my school clothes.

I was still grinning.

Wednesday: A day that would reverberate through the annals of history. A day of infamy. The day that sparked the genesis of that vile fiend, that masterful sociopath and all-round sex-addict cherry-popper known only in his deranged and unashamedly lecherous mind as...

Master Player Kyousuke.