Author's Note: Sorry for such a late update, got a lot of work in my hands. Before we got into this chapter, I want to clarify something for you guys.

Q: Will Madara's personality stay as the battle maniac/ruthless and cold one?

A: Before I answer this, let me explain a certain thing about the backstory of Madara. True, he was a cold, ruthless killer that will kill anyone that stands in his way towards his dream.

But think about it for a second. He used to be an extremely kind person, despite the fact that his brother Izuna got killed by Tobirama, he joined force with Hashirama to create Konoha once Hashirama showed the truthful self to him. He is an extremely kind person, but only to be push to absolute loneliness by the democratic law made by Tobirama and the ignorance of his clan.

After that, he submits to the Curse of Hatred and desire to change the world with any means necessary. But when his plan failed, despite his ruthless and merciless attitude, he still expressed a certain degree of regret and acceptance of new ideas and paths.

In short, Madara will be a little bit more accepting and slightly gentler but only to the one that earns his respect (AKA Powerful). Now don't get me wrong, I'm not planning to just change Madara's personality into a Good-Gary-Every hot girls will have sex with me-Stu personality. He will remain a battle maniac who enjoys fighting and be cold/ruthless to his enemies, but he will not be the 'Infinite Tsukuyomi Ambitious Madara'.

Q: Madara & Harem? Wat?

A: I know that it is hard to picture him having such a thing. Hell, I won't even deny it that I couldn't even imagine it. But put yourself in his shoes, being alone for your ENTIRE life, focusing solely on your ambitions and dreams, only to fail and learn that it is not the correct way. Don't you want to do something else after that? After Madara's plans failed and when he saw the error of his ways, don't you think that he wanted to do something else for a change? For example, having a family of his own. Then again, I will not just randomly throw the relationship at him, but if you think about it… Uchiha Clan is the clan that value love above all else, so I think that this kind of make sense… at least to me.

Sorry for making you read such a long ass notes, but I just hope that I make all of you understand the context of Madara and the story better.

Anyway, let's get on with the chapter!

P.S. Important Announcement at the end of the chapter.

Second Chance

Chapter 2

Issei Hyoudou, one of the proud members of perverted trios, is in a very deep thought. Despite his ultimate perverseness, today, he hasn't had any perverted thoughts at all. Seriously!

That's because of the yesterday's events. Not the part where he nearly got turned into a shish kebab, not the part where he got smothered by his master's breast either.

-Flashback-

"What are you talking about…?" Rias muttered in disbelief.

Apparently, all of them are sitting in the living room of Uchiha Madara's "humble" abode. Just for an etiquette purpose, Madara poured each of them a cup of tea before sitting down on his favorite couch while Ophis just browsing through various TV channels. Both already introduced themselves, so they are conversing about the main topic.

Sona sighed. "Just like I said Rias, the true reason why Uchiha-sensei is here, is to act as your temporary guardian due to Maou-sama's… request."

"But then why didn't Onii-sama told me about all of this?!" Rias exclaimed unhappily.

Sona massaged her temple. "Uchiha-sensei… please…" She begged for Madara's explanation.

"Because Sirzechs speculated that you will definitely complain and bug him about this over and over again." Madara commented nonchalantly.

Rias fumed a little. "That's because I do not wish to have any of this!"

"Neither do I wish to be here, Gremory. But apparently, the price that your brother decided to pay is quite worthy of my time."

"I have a quick question." Akeno raised her hand. "Why would you let Sona-kaichou tell us about your mission? I thought that you wanted to keep it as a secret."

Madara shrugged. "Basically because I do not care if she founds out or not. If ultimately, something happened and I'm no longer under contract, Sirzechs will have to pay me either way." Madara smirked while eating his favorite potato chips.

Everyone looked at Madara confusedly. Even Sona does not know this fact.

"How can you be so sure? Sensei?" Rias narrowed her eyes.

Madara shook his head before pinching the bridge of his nose. "I think I just changed my mind. I shouldn't let anyone, especially you, know about this." The Uchiha is starting to get annoyed by questions that were thrown at him.

Rias pouted a little. She just wants to know, she has the right to know, okay?!

"Let's see…" Madara sighed before reaching for a small booklet in his pocket. "Here it is, let me read some excerpts for you, especially for the "Gremory Princess"."

Madara cleared his throat while everyone focused all of their attention at the warmonger.

"The embarrassing secrets of the current Maou Lucifer."

Everyone's eyes widened, especially Rias'

"Apparently, your brother has a certain fetish for knee socks and… oh, bloomers? That's very mature, don't you think?"

"B-B-Bloomers…? K-Knee socks…?" Ise blushed dreamily before blood slowly tricking down his nose while others considerably blushed at Sirzechs secrets. For Rias, she just wants to cover her face before hiding under a rock.

"Hmm, rabbit ears, used underwear, sexy talks, outdoor plays, whips? Your brother has a somewhat exquisite taste there, hm? Gremory?"

"S-Sensei…"

"Ho? Now this is the interesting part. Whenever he is having sex, he usually-"

"Okay! Okay! Please sensei! Please!" Rias cried a waterfall as her face hit the floor.

"Hehehe… Rias-sempai, your brother has a very good tas- Ack!" Ise who previously was drooling dreamily got punched in the face by Koneko.

"Pervert. Lecherous low life bug, just crawl under a rock and die." Koneko insulted monotonously.

Madara closed the booklet before smirking. "I know you would understand." He said before pointing at the royal-looking chandeliers. "This house and almost everything in it, was just a tiny part of my "salary" so to speak." Madara explained. "The best part is… this." The Uchiha took out an official looking paper.

"U-Uchiha-sensei… that's…" Sona's eyes widened.

"Blood contract between me and Sirzechs." Madara handed the document to Sona.

With a hidden fear in her heart, Sona began to read it. "Uchiha Madara is eligible to enter the Underworld regardless of his human status. Additionally, he is officially free to challenge any devils he deems worthy to a full-out fi- What in the world is this, sensei?!" Sona exclaimed.

"Why are you getting so worked up?" Madara deadpanned tiredly. "It's just the right to challenge any devils to a full all-out battle without having to worry about any consequences. Although, it's too bad that the contract excluded the Maous along with fight-to-the-death type of battle."

Ophis walked up to the Uchiha before snatching a piece of his potato chip. "I, still don't understand. You could just declare war on them, and fight them to the death if you wanted to." She said tonelessly.

Everyone unconsciously flinched.

Madara sighed. "Listen here Ophis. I would love to have those kinds of battles once in a while, but that doesn't give me the right to take other people's lives." Madara lightly lectured Ophis.

Ophis tilted her head. "I, see… I think?"

"I may enjoy battling and killing at certain degree, but I do have morals. I did learn to have it from first-hand experience." Madara sighed almost guiltily.

Ophis blinked before nodding slightly.

Madara nodded in satisfaction. Also, he could always hunt down other powerful stray devils or other "wanted" criminals if he is really itching for a real death fight anyway.

"Wait! Hold on- Arrrrghhh! I don't understand any of this." Ise interfered.

"Oh… I totally forgot about you, boy." Madara said nonchalantly.

Rias sighed before standing up straight. "You see, Hyoudou Issei-kun. We're devils." She said smilingly before a pair of bat-like wings appeared.

The rest of Rias peerage along with Sona followed the suit as they also have their wings out.

Ise stumbled backwards in surprise, only to be pushed forward as his wings automatically manifested out of his back as well.

"B-But… how could this-"

"Do you remember Yuuma Amano?"

Ise immediately flinched as he heard that name.

Rias adopted a thinking pose. "She's a Fallen Angel. Her true name is Raynare, ring any bells?" The Crimson Princess asked smilingly.

Ise nodded reluctantly as all of his memories is slowly returning to him.

"I-I see! W-What about Ophis-chan and sensei?" Ise asked reluctantly.

Everyone seemed to instantly become engrossed in this topic.

Ophis stared at Madara with impassive look. Madara seemingly ignores Ophis while keep munching on his potato chips.

Seeing no response, Ophis gently pull Madara's sleeves.

"Don't look at me Ophis. These children will not believe me, even if I wanted to tell them." Madara responded nonchalantly.

"Is that so?" Ophis tilted her head curiously.

Sona bit her thumb slightly. She already speculated that the man hired by someone like Maou Lucifer, cannot be weak or unreliable. But his presence is really not different from any normal human… so what really is he?

Madara nodded slightly. "If you feel the need to proclaim your title as the Infinite Dragon, then go ahead and tell them."

Sona dropped her tea cup in shock as well as Tsubaki. Rias shakily point at Ophis while Akeno and Koneko failed miserably to hide their expression. Ise just look at the sempais with confused expression.

"I-Infinite Dragon… d-don't tell me…" Sona muttered in fear as she felt a lump in her throat.

"Understood." Ophis replied emotionlessly before turning her attention towards the group. "I, shall proclaim my title now. I, am-"

-End of Flashback-

Ise sighed frustratingly. Apparently, Ophis-chan is the ridiculously powerful Infinite Dragon, but Madara-sensei refused to tell them about his status… Also, yesterday, he awakened his Sacred Gear, something called Twice Critical according to Rias-sempai. After some long explanation on how devil society works, his goal is now to become a Harem King! But the road towards his dreams… are incredibly far, according to Rias' claim. He will have to be a lot more powerful, influential, capable which means he has to train more, do more contracts, do more- Arrrrgh! So many things to do!

"Gaaaah! I want to have a Harem!" Ise shouted.

The class immediately went silent as the History teacher stared at Ise with an anger mark on his head.

"Issei Hyoudou."

Ise suddenly become aware of his surroundings. "Y-Yes, sensei?"

"Sit down and be silent, before I sent you to the Student Council."

"H-Hai…"

Meanwhile…

Fweeeeeeeeeeeeee!

"No slacking! You can rest when you are dead, keep moving!"

The students groaned exhaustingly as the slaves' driver, Uchiha Madara in his warm-up uniform, decided to whip his students into shape again. This time, it's the 2nd year students' P.E. Class.

"B-But Sensei! *pant* W-We aren't in the military y-you know?"

"Military or not, most of you lack discipline! Look at the girls from the Kendo Club!" Madara shouted while crossing his arms.

The girls blushed from Madara's compliment, but immediately tightly sealed their fangirl attitude because they know better. The Official Title for Madara was already out the first day he arrived here as, "The Nightmare". His reputation spread like a wildfire throughout the school as the harshest and most disciplined teacher in the school. Although, the 3rd year students say that he did this so that his students will learn discipline and hard work.

This escalated into a formation of a secret group called Madara's Lover Committee… in just one goddamn day! This, annoyed and infuriated Madara to no end, but as long as they stay out of his way and does not make his life more difficult than it is… he will not interfere.

"B-But Sensei…" Another male student tried to voice his reasons.

"Silence. Do you see any of them complaining? They are doing their best despite the impossible task, and yet you still have the audacity to keep complaining? Where are all of your pride as a man?" Madara shouted irritatingly.

The male students immediately flinched. Some felt sad, some felt disappointed in themselves, and some felt extremely angry at Madara from that insult.

"I could care less about what all of you think about me, but I will fail any of you if I see you give me something less than a hundred percent." Madara narrowed his eyes dangerously. "Now, will you keep whining and fail like a problematic child? Or grow some balls and be a man? Your choice."

The male students immediately let out a roar before all of them, whether physically weak or strong, increased their running speed exponentially.

Madara nodded in satisfaction. He would say that he kind of enjoyed being a teacher. Not because the privilege to see students struggled and collapsing in pain or anything… well, that might be a minor point. The major point is, to see the youngsters trying their hardest and giving it their all, it is quite refreshing to see.

After another 30 minutes of constant extreme exercise. Madara signaled the end of class 15 minutes earlier than officially scheduled.

"Clean up, take a quick shower, and prepare for your next class. Dismissed!"

He got numerous of exhausted response as the students tiredly jogged towards the locker room.

"Can we go now?"

While looking at the gothic girl, Madara gently bopped Ophis on her head. "You also need more self-discipline."

Ophis pouted emotionlessly."I, have discipline. I, just don't see the point to maintain them."

Madara sighed. Well, that was the last class he got to teach for today, so going home will be fine. Not wanting to argue with Ophis, he nodded slightly before gathering all the tools and equipments back to where it belongs.

Ophis just stand there motionlessly before scanning the surroundings uninterestingly. She saw couple of students, giggling and waving at her from the school building.

"Ophis…?" Madara came back from the storage room and saw Ophis waved nonchalantly back at the students.

"It seems that your "story" is extremely effective." From inhumane hearing, Ophis managed to hear the students called her as Madara's cute, adorable little sister.

Madara nodded. "Hn. Apparently, we looked somewhat similar." He smirked.

"But technically, aren't we are an actual siblings in a sense…?"

"Hah?" Madara raised his eyebrows at Ophis' monotonous question while both of them are exiting the school's premises.

Ophis kept walking straight forward. "Since your body is constructed by my flesh and power combined with that… despicable, dreadful, vulgar, hopeless, unsightly, miserable existence of all dragons race-"

Madara sweatdropped at Ophis' venomous yet emotionless insults at Great Red. "Ophis, you are getting off-topic."

"I, did?" Ophis asked confusedly.

Madara knead his forehead while sighing. "Do not think too much about small details. Let's say, we're family." Almost non-existence smile adorned Madara's face.

"Really?" Almost equally impossible, Ophis smiled a little.

Madara nodded. "But, killing that Red Lizard is out of question, you hear?"

Ophis immediately pouted. "Then, I, shall follow you until you help me skin him alive."

"Hmph, be my guest." Madara chuckled.

Both two enigmatic figures slowly walked towards their house, before someone decided to interfere with their little bonding time.

Madara narrowed his eyes as he recognized the man. "Ophis. You go on ahead. If you're hungry, the Fried Tofu is in the fridge."

"Is it Inarizushi?" (Fried Tofu filled with Sushi Rice)

Madara nodded slightly.

"Yay." With monotonous response, Ophis walks passed the mysterious man towards her self-proclaimed "temporary" home.

The mysterious man chuckled. "I can't even believe it that she is the Ouroboros Dragon."

"If your reasons for interfering me are not good enough, then you will pay dearly." Madara stated coldly.

The man immediately flinched before waving his hands apologetically. "W-Well hold on, Madara-san! I'm just here to tell you about a newly upcoming job. If you are interested, that is." The man said in a sing-song tone, but Madara could clearly detect a tiny hidden fear in his voice.

"Hmph, be quick with it."

"Thank you so much! So, here's the information."

Madara took the documents out of the paper folders before scanning through it.

Today, Ise got to officially introduced himself to everyone in Rias Peerage. He does not expect that Kiba Yuuto, the enemy of his harem plan, is also one of Rias' peerage members. At the moment, the sun is still up in the skies, but luckily for the lucky pervert he already finished all of his classes for today. Instead of heading home, he decided to take a walk in the park. Almost like a divine intervention, he accidently bumped on a blonde girl, who is wearing a nun outfit.

"A-Are you all right?" Ise slowly helped a blonde girl up.

"T-Thank you very much."

Ise blushed perversely at the innocent-looking beautiful young girl. "S-Sorry for that! I did not pay attention enough." He repacked the suitcase for the nun.

"N-No, it's not your fault. It was my clumsiness… u-uhm, thank you." She smiled while her cheeks are adorned with pink tinge.

Ise mentally screamed from the immense cuteness. "I-I'm Issei Hyoudou!"

"Ah, Issei-san! My name is Asia Argento, nice to meet you." Asia smiled brightly.

From further conversation, Issei found out that Asia is a nun that came here from another country for religious purpose. She also contained some strange power that Issei could not comprehend, the ability to heal injuries. She used it to heal a boy who accidently fell and injured his knee. Despite his personal enjoyment of talking and walking along with such a cute girl, he can't help but feel nervous at the same time. Not from Asia's appearance, but from her… cross necklace. Temporary sharp pain was also felt whenever Asia mentioned the name God.

After helping her advancing into the right direction, both of them reached the edge of the urban areas, a lone church is standing high up on the hill in front of them.

Almost instantly, Ise flinched as he sensed some danger emitting from the church.

"Eh? Ise-san, are you okay?" Asia sensed some of Ise's nervousness.

"I-I'm fine! It's just that- uh, I just remembered that I have a meeting with my friends!" Ise laughed nervously.

"Ah! I-I'm sorry! It's my fault from dragging you all the way here…" Asia muttered with teary eyes.

"It's fine! No problem at all, I enjoyed helping you here!"

Asia sniffed a little. "Really?"

"Yes, really! But, I really need to get going now…"

Asia smiled. "Please go, don't let me keep you here, Ise-san. If you have some free time, please come visit me at the church, okay?"

Ise nodded smilingly. "Let's meet each other again! I promise!"

Asia nodded with an extremely happy smile while waving at Ise. She couldn't hope for a better day than this.

Unknown to both of them, there is one outsider watching them all the way here. Two crimson eyes shone intimidatingly in the dark before it instantly disappears.

Time flies by like an arrow as the next day arrived.

The day progressed normally for Uchiha Madara apart from the presence of Ophis, the Ouroboros Dragon. Apparently, despite being one of the strongest existences in the world, she still has some private matters to attend. Madara, not wanting to meddle with her personal matter, just nodded knowingly before resuming his normal routine. Driving the students to the brink of collapsing.

Instead of just barking at the students, he also decided to warm up a little in preparation of a little "job" that he was "hired" to do.

After the students are totally wasted from his usual impossible training task, he signaled the end of class.

Wave after wave of beaten-up students left the field. Five minutes later, he is finally by himself.

"Hn, I still got some time to kill." Madara thought as the orange tinge started to appear on the horizon. He decided to make haste towards his home, proper attires are required for this.

Discarding his usual trainer uniform, he put on a black shinobi vest along with the corresponding black pants. With amazing speed, he neatly wrapped bandages around his legs, giving him the nostalgic shinobi looks.

Glancing at the clock, Madara narrowed his eyes as the suitable time is near. He closed his eyes to heighten his sensing. For a split second, the corner of the Uchiha's mouth curved up slightly, the target is now in place. "If I do not get what I was promised with, I'll be sure to make you pay dearly…" Madara thought about his "client" before instantly disappearing into the shadows.

Meanwhile, in some random client's house…

"Let go of Asia! You bastard!" Ise shouted while being held back by Koneko and Kiba.

"Hehehehehe! You shitty devil! You think I'll listen to you?! I'll rape this bitch in front of you if I want to! Hyahahahahaha!" The crazed exorcist laughed maniacally as he kicked the poor blonde girl again.

Ise gritted his teeth as his angers flared up dangerously. "Let me go! I'm going to save Asia!"

"Calm down! Ise-kun!" Kiba shouted.

Koneko nodded. "There are multiple incoming signatures. Fallen Angels." She analyzed monotonously.

Freed laughed bloodthirstily. "That's right! This is my epic come back, you shitty devils! I will burn you like a fucking witch on a stick!" Bright white portal formed on the ceilings as soon as Freed finished his ranting.

Judging from the presence that she felt, it might be more than what all of them could handle at the moment. "Tch… Akeno!" Rias made up her mind.

"Hai, Buchou." Akeno frowned knowingly as a sizable crimson circle appeared beneath all of them.

"Hahahahaha! You think I'm going to let you cowards run away?! You shi-" Freed's face got slammed by a wooden table.

"Vulgar mouth should be kept shut." Koneko commented unhappily.

"N-No! NO! ASIA!" Ise shouted as tears trickled down his cheeks. Kiba kept his grip tight on Ise to prevent him from getting out of the magic circle. "Buchou! Please, take Asia with us! We can't leave her here!" Ise shouted with despair in his tone.

Rias kept her face straight. "I'm sorry, Ise… but only someone that bear my household marks can use the magic circle…" She informed Ise almost regretfully.

"T-That's…" Ise's face immediately paled.

"Buchou, we're ready." Akeno said.

Rias nodded. "Do it."

"NO! WAIT! ASIA! ASIA!" Ise screamed his lungs out as he can no longer contain his emotions.

Asia slowly but painfully sat up straight, while looking at Ise with teary smile. "Ise-san… let's meet each other again…"

The crimson light shines brighter and brighter.

"ASI-"

Before all of them are teleported away, the whole building shook violently as the floor of the room started to crack.

Everyone widened their eyes in shock as multiple gigantic plant tendrils drilled through the floor, blocking Ise and others from seeing Asia for maybe one last time.

"Let's go!" Rias shouted. Ise screamed something incomprehensible before-

Everyone in the Gremory peerage disappeared as they successfully make the jump.

"Fuck! That hurts!" Freed swore as he wiped the blood off his face, only to met with a thick wall of vines in front of him. "What the fuck is this?!"

Almost instantly, Freed could feel a chill running through his spines as a human-like being stand outside of the door, staring at him with two piercing crimson eyes.

"W-Who the fuck are you?!" Freed shouted as he gripped his holy sword tightly.

Madara completely ignored Freed's question before slowly walking into the room. Asia could only flinch away from the icy and merciless stare of the Uchiha.

Madara's gaze softens for an extremely tiny bit as he noticed Asia. The Eternal Mangekyō Sharingan in his eyes shone bright in scarlet color as he stared into the eyes of Asia Argento.

"W-What… Why am I…" Asia suddenly felt sleepy, she is completely hypnotized by the pattern of the man's eyes. Instantly, she slumped on the ground, totally losing her consciousness.

"You. Are you Freed Sellzen?" Madara turned his attention to the stray exorcist.

"Fuck you!" Freed pulled out a handgun and continuously fire the holy bullets at Madara. "Die! You red-eyed freak!" The insane priest shouted as he hastily emptied his magazine.

The sounds of gun fire stopped as Freed could only gaped in shock. All of his bullets failed to injure, let alone penetrate the clothes of the Ghost of Uchiha.

Before Freed could say anything, he felt an extremely powerful hit on his abdomen Madara just vanished from his previous position before kicking Freed with a holding-backed chakra-reinforced kick.

The insane priest crashed into the wall behind him before gurgled out a lot of blood. He is so sure that his stomach just got badly damaged as the shock from the strike causes his ribs to dislocate.

"Hmph… insect will still be an insect." Madara commented nonchalantly. "Utilizing the stored-holy power in a special container to create the illusion of imminent reinforcements. Pathetic." The white portal on the ceilings dissipated as the holy power that supplies it is gone.

Freed gritted his teeth as the pain prevented him from even utter a single reply.

"I have a certain task for you. Insect." Madara forced Freed to look into his eyes as the Eternal Mangekyō Sharingan pierces through the rogue exorcist's soul.

Fear formed behind the two orbs of Freed before everything around him went black.

Madara let go of the rogue exorcist, causing Freed to fall down violently on the floor. "Phase 1, complete." He muttered to himself before he slowly disappeared into the darkness.

End of Chapter 2.

I apologize, but I just don't think that it is a good idea to cram everything at the intro A/N. I want to announce that, the next chapter might be a little late, because I got the chance to take a vacation at Tokyo, Japan.

I'll try to crank the next chapter as fast as I can while keeping the same quality, but if it isn't updated by the 22 July, then you guys probably gotta wait for 1 week. Sorry about that.

Anyway, thanks for reading, and stay tune!