Disclaimer: I do not own nor claim property of Ore No Imouto Ga Konna Ni Kawaii Wake Ga Nai / OreImo / My Little Sister Can't be This Cute. The origins belong to the novelization provided by Tsukasa Fushimi. Guest characters, including but not limited to: Hikage Sumino, Eru Chitanda, and Oreki Houtarou, belong to their respective authors.

A/N: Please note that this story is the continuation of the Complex entries created by Zkname and enhanced by me. This story takes place shortly before the start of Volume 4 Chapter 4 (i.e. before Kirino surprises Kyousuke that she will be travelling to America) so that the events can coincide with the end of school semester. Although certain scenes may be included, not all originally canonical events will appear in this story moving forward.

A/N: Please enjoy the lifelong dilemma of the Kousaka siblings.

['Good, and you better keep it that way... Aniki."]

A week had passed since that awkward expectation was set, and Kyousuke was still troubled by it. Nothing seemed able to take his mind off the subject, not to the fact that there was clear intentions behind her words- especially coupled with that wonderful smile from his little sister.

"Urgh, my life is never going to be normal... Ever again," Kyousuke mentally resigned himself to that fact then rubbed his eyes for what appeared to be the hundredth time that day.

Since then, Kyousuke managed to develop a routine to avoid his sister at all cost: stay locked up on his room until food was ready, focus on eating and only eating, then excuse himself as soon as possible to escape a potentially hell. His parents scolded him more than once at the table for his new habit, clearly noting that some trouble had stirred since that troublesome night awhile back; Kirino did not help the state of matters by staring wicked daggers in his direction every so often between bites. So long as he lived, he swore to keep up that tactic no matter the cost!

Kyousuke could not afford to give a swift glance towards his sister without being barraged by very unwanted reminders and thoughts. After all, he did fuck his sister... Drunk, obviously. Both he and Kirino were blissfully intoxicated that night from consuming wine (what he learned to be wine later that week).

Surely, Kyousuke wasn't having those recurring thoughts of himself on top her Kirino out of sheer desire, he tried to convince himself every time. The constant reminder that due to that night, he was no longer a virgin. The stain on his sex life would remain with him for the rest of his miserable existence.

"With my own sister... Damn," he grumbled in a low tone, once again rubbing his eyes.

He read somewhere that men were supposed to engrave that very time of their life into their soul, considering that the first time can never be reclaimed. The very thought pleased and urked him at the same time- the sheer tightness of her insides; the pleasant warmth surrounding him; the intense pulsing pleasure that stroked him; his beloved name whimpered amidst short desperate breaths of hot, passionate moaning-

*Smack*

"Urgh damn! Damn! Just stop that already!"

Kyousuke disciplined himself with a rough trained slap across the face, his best resort to clear his mind of such dirty thoughts. As necessary he would castrate himself to prostrate any unintended joy. Thankfully the single slap was sufficient to drag him back into reality and into the task at hand. He took up his pen in hand and tapped at the unfinished work.

"I better get this done else I'll really be in pain."

Several stacks of incomplete pages were arranged atop his desk. The sheer number of piles were as intimidating as the small Times New Roman font printed upon them. All of these documents were assigned to be completed in full by his father that learning of the lack of bottles in the refrigerator.

Kyousuke would remember that lesson vividly for the rest of his days, how his father raged at the empty pinot noir discarded into the trash can which would have otherwise been set aside for Daisuke's joyous occasion. To make up for that loss, 360 pages of miscellaneous reports, intentionally whited out of important key words, given to him to finish by the end of 2 week's time. Considering the current lapse in time since, he had until tomorrow morning to turn in.

Fortunate for the young teen, luck was on Kyousuke's side. The needed terms were a simple English-to-Japanese translation not that uncommon during this ending school semester; not to mention that English was already a language Kyousuke managed to get down well. Thus far Kyousuke completed up to 280 pages during the lull of his sister bothering him. With this rate he should be all done this night, then take on his much deserved rest.

The award was highly appreciated by Kyousuke, considering his lack of week during these last few weeks. Such troubles were thanks to the incestuous drama brewing between him and his sister.

"Well, maybe not that dramatic," Kyousuke rationalized at that point. Despite how Kirino clung to him during their convention trip and train ride back, his sister had not been approaching him. In fact, she hadn't brought anything up to him at all since before then, not about eroge or life in general. In fact, he would very well deduce that Kirino was avoiding him.

A single breakaway stare rarely when they crossed each other's path. The uncomfortable silence at the dinner table and those ungodly stares of hers. Above all though, no eroge that he was required to complete.

"Ah, that's right. I haven't played anything since then," Kyousuke amused to himself as a wave of relief washed over him because of that single tact. 2 weeks and counting since he had been bothered with the them of little sister love-making (instead, experiencing it firsthand). He hadn't even been forced into borrowing her laptop again to rush through a light novel or two now that the school semester was coming to a close.

'Yeah, more than likely she will be coming at me full force to make up for lost time. That's for sure,'

Kyousuke's concerns grew between jolting down proper infinities on the page in front of him. Kirino would not let him get away that easily with being at ease, especially if she was not-

Kyousuke stopped short of a sentence, then looked over to the wall separating them. Not at all at ease...

"...Maybe I'm overthinking... Yeah, must be."

He shouldn't' be. Ever since discovering her hobby, he had become more conscious of his sister's feelings. Rather, has he should have been as a proper older brother. If only her concern the last time they actually talked was either or not each other were their firsts... Still, why hadn't she pressed on more than just that? He had heard from some of his more 'adventurous' classmates that girls to be exceptionally clingy after their first time. Not to mention that tendency solidified through the game genre he has been forced to become familiar with.

Kyousuke looked up at his clock hanging overhead. The time was 23:57. Typically at that time, his parents would be dead asleep, and Kirino would be - as a matter of fact- locked up in her room playing those eroge without end. He wonder if she even touched herself during-

"No no no, I don't want to know that!" Kyousuke stopped himself then put his pen down, then stood up and approached his door. He stood before it as if poised of a challenge to present itself in the form of the person on his mind. He dared not open it for the moment. He dared not to step out there and confront her about the current situation.

...

Yet... Should be doing just that? As her older concerned brother? Would this not be his duty since his sister dared not do so either?

Despite the horror that arose because of their circumstances, Kyousuke had to admin that the missed that connection he had with Kirino- the one and only thing that connected the two siblings (if only it were not so erotic...). He wondered if his sister was alright... He could not hear the muffled laughs or jeers that would usually permeate through to him in the dead of the night. Just hearing even a regretful moan would put his wandering mind at least.

"...Just damn it, I have to do it."

With reluctance, Kyousuke found himself opening his door and hasten his way through hers. His hand was poised to knock. As much as he would prefer this type of silence that yielded a normal night, he couldn't go on not knowing if his sister was okay.

However, just as he prepared his nerves to knock, the door in front of him creaked open slightly, a crouched figure slipping out below. Kirino had emerged in a full crouch in an attempt to back out of her own room, doing an attempt to sneak out. His sister didn't get far though before she bumped into Kyousuke, reacting in a loud yelp. Kyousuke rushed forward to stiffen the noise with his hand.

"Shh! Don't be so loud! Do you want to wake up- OMPH!'

Kirino's knuckles connected with his chin the moment she broke free from his clutches, finishing up in a signature move common in fighting games.

"What are you doing in front of my door?! You pervert!"

"P-Pervert?" He was somehow taken aback despite the insult being so common in her vocabulary. "I wasn't even doing anything! Why are you sneaking out of your room anyways?"

"I-I don't have to answer to the likes of you! Besides what are YOU doing standing in front of mine?! That's so creepy! In the middle of the night too!"

Despite that the timing could have been better, Kyousuke found some relief in the fact that he was engaging with his sister once more (hell, that beat filing paperwork). If only there was not much aggression behind her tone...

"I Just- ... I wanted to see how you were doing... You know... You haven't exactly been yourself lately, not pestering me with eroge and all..."

To that, Kirino remained silent. Kyousuke could not make out what type of face his sister was making due to the darkness int he hallway. He did note how she wore her usual night clothes- those very blue short-shorts and a pink tank top that left room to the imagination. The familiar pink hair clip simmered lightly against the distant light coming from inside her room. More importantly as time went on, he realized the determined frown plastered on her face glaring at him. Yeah, something was up with her.

"... That doesn't give you the right to just lean against my door to find out."

"You know that wasn't my intent. Now I told you what I was doing. Now's your turn." In response she chose to remain silent. The lack of response annoyed Kyousuke. "Just tell me, I'm not going to be mad-"

"I wanted... to see you."

The sudden statement and its vague meaning caused Kyousuke to become flustered. He was irked at the thought, but flushed all the same. Was she planning to sneak into his room like the first time he confirmed her obsession to force him into a compromising position? Can't she ever do something normal- like knock on his door during the day and ask a question?

"Wh-What about?"

After a moment, Kirino glanced from side-to-side then down the hallways towards the stairs, then took his hand and tugged him in.

"In my room. Not out here."

Instinctively, Kyousuke yanked free from his sister.

"H-Hell no! What are you planning?"

"BE QUIET. GET IN. MY ROOM. NOW."

The sharp staccato she placed behind her words was not a force to be reckoned with, nor did her brother dare to try. He slipped beside his sister and offered a hand in apology then allowed her to shut the door behind them. She didn't bother to follow him in from there though, not budging from the door as Kyousuke turned around. The two stood still and shared in the uncomfortable silence.

Who would be the first to talk, Kyousuke wondered to himself. Despite wanting to come talk to his sister, he didn't know how to go about it in this scenario. Alas, he could not bare another moment of silence.

"Why are you-"

"I- I need... your advise."

Kyousuke took a step back in feigned shock from his sister. Although a common preposition given to him throughout the year, this time around it seemed to catch him off-guard greater than the first time. Kirino took that chance to continue on since her brother would not.

"A-About... that night..."

"Y-You mean... when we?"

"...Yes.:"

Somehow, that brought out the bottled angst within the brother. "Seriously? You want my advise about what I did to you?" Kirino turned her face away from her, the simple act egging him on. "Yu can't be serious! You don't need me for that! You need a proper psychiatrist! Not the guy who forced you into that! I mean, do you even realize what we done?! How messed up we are?!" His voice raised without him noticing, to which Kirino forced a hand up to remind him.

"Keep it down, you idiot!"

"Still! What do you expect me to do?! We should be seeking professional counsel for this!"

"I-I don't want anyone else to-"

"You need to! Don't come to me for this! Because of me I've ruined so many chances for you! I mean- We DID that, Kirino! No amount of 'life counselling' will ever erase that from our lives! We can't go back and-"

"I don't want to!"

Kyousuke froze at her fierce rebuttal. He watched as she grit her teeth and fought back against raging tears.

"I don't want to undo that! I don't! I just - I I can't-" Kirino tried to carry on despite the earnest tears being in his eyes, and the blush reddening her complexion. A sudden rush of sniffs and hiccups clamored from her mouth as she fought back against her own obvious frustrations at the situation. Kyousuke caught on quick that his sister was about to break down faster than he had, thus gave up and rushed to her.

He instinctively cradles her had into his shoulder as he attempted to calm himself. He felt her struggle against him and punch his chest. But he endured. 'Jeez, what the hell am I supposed to do?'

Despite continuing to mutter profanities towards him and beating against him, Kirino seemed to simmer down after a few minutes and clung to his shirt. He kept still until she finally steeled herself and pushed him off. She dared not look into his eyes and he dared not to do the same. The silence returned as the siblings stood off.

"...What would you want me to do here? I don't think there is anything... I..."

Kyousuke was unsure how to bring this to a close. Should he be blunt? Would this ruin their relationship forever? Despite the possibility, he had to choose for them as the oldest one, thus he endured it with a deep breath.

"We should just- just forget it... Bury it in the past. I don't want to-"

"...Life... Counseling," Kirino responded in kind before he could properly end. He looked over to his sister in concern.

"I want you... To take responsibility."

Kyousuke was... baffled, to say the least. Hers was an unusual proposal, considering the gravity of the situation. Was she... really wanting to continue on with their continuity? Shouldn't he be rightfully rejecting this and move on from his sister? Kyousuke new that possibly accepting whatever was on her mind would bring devastation to them both... Neither of them could mend their budding friendship after this point. Still...

"What... do you want me to do?"

"...oyfriend."

"...:"

Kyousuke could barely make out the word she muttered. He knew the word existed in his mind, but he could not fathom what it was. He regretted asking her to repeat it."

"What was that?"

"I want you... to be... m-my... boyfriend."

"..."

"..."

*Cough**Cough*

Kyousuke chocked on the lack of air after hearing her more clear proposal. He nearly fell backwards due to the impact of her words, yet Kirino remained not phased by her remedy. Instead she seemed to bear herself to accept his response, her fists gripped hard beside her. Not doubt hidden behind her hair was a strong blush on her face.

"Wh-Wha?! What are you saying?! Do-Do you even know what you just said?!"

":I- I know what I said! Listen to me, idiot! As I'm only going to say this once!" Kirino managed to spurt out as she resisted the urge to berate him. "I want you... You to be my first... For many things! And you have a responsibility to see me through this! As my boyfriend!"

"Gwaaah?!"

"You've already done the worst possible thing! So! You need to MAN UP!"

Stunned, Kyousuke looked at his frustrated sister in shock. One phrase ran through his mind in an instant. 'Just what the hell is going on?!'

Did his little sister just seriously demand that he begin a serious relationship with her?! Was he being forced down the Romance route just because they got drunk and made love?!

He could understand this better if he was otherwise dragged into her room and beaten senseless for his crime, but this! How would a criminal such as her brother even entertain this notion? Kyousuke knew his life was way too fucked up for this to be even real.

Life flashed before his eyes now that he stood at Heaven's pearly white gates only to be thrust down in the underworld for his sins. 'Abandon all hope ye who enter' harkened him into that domain. This would be his first true steps there being forced upon him.

"A-And if I refuse?" Kyousuke managed to inquire despite knowing he might be beaten up regardless of thee fact. Kirino seemed to take his question serious, and pointed her finger at his face.

"I'll tell Dad that you sexually harassed me and took my virgini-"

"Yes yes! I'll do it! Please don't even consider that! My life would be forfeit! I-"

Before he could even ramble on about his doom, Kyousuke found his sister lunged into his chest, his being grasped tight against her small frame. Just from that alone, he would tell that his sister was being dead serious. Because of this, despite knowing the road before them was hell incarnate, he wrapped his arms around his sister in agreement.

However, Kirino only permitted this for a few second before she snapped out of his range. "You don't get to do that yet, pervert!"

"Wh-Wha?! I was just trying to-" Before he could breath out another word, Kirino grasped his collar and threw him out of her room with little effort.

"You will receive your first mission tomorrow! Go finish your assignment and get to sleep! My boyfriend cannot be sleepy on our first day together! Idiot!"

The door slammed in his face, and he had nothing to contest to that. The moment lingered before the dumbstruck brother as he stood still. In truth, he had nothing to say to his sister after that point. He was already fucked quite thoroughly up to that point in his life. What was otherwise a budding friendship with his sister now began to be a romantic relationship. The route stated without Kyousuke being able to select another answer.

Resigned to his fate, he turned around to return to his room, then the door behind him clicked open. He dared not turn around in the fear of being punched some more, but then-

"T-Thank you... Kyou... su... Idiot."

The door creaked shut silently for the first time in a long wile. In response to this unexpected development at the end of a crazy buildup, Kyousuke's heart jumped. Did she... Try to say his name in sincerity? After thanking him, no less?!

Kyousuke blushed at the thought. His name was seldom spoken by his sister, and each time she managed to barely brush by it made his body weak. Just like that night, he recalled, when he heard her so pleasantly call out to him amidst heated-

"Y-Yeah," Kyousuke whispered to an absent Kirino as he went to his door and shut it behind him. Almost mechanically, he returned to his desk and picked up his pencil. He remained motionless of a moment, unable to find the drive to resume his work. His eyes roamed to the wall separately him from his sister briefly before returning back. Automatically with a sigh, he submitted himself to the paperwork and rushed into getting it all done.

"Everything's about to get more complicated from now on..."