(10 Days till the match.)

The next day Grayfia returned with the details of the coming match. It would be held ten days from today and will be observed by both families. On top of that, one of the Maoh, Adjuka Beelzebub, would provide temporary pieces for the game to allow Issei and his servants to participate. After the explanation the ORC met up at Issei's house to head to Chaldea.

"Alright, is everybody ready to go?" Asked Issei.

Everybody nodded in confirmation and Kiba asked what the devils were all wondering. "So how are we getting to your organization?"

Issei had a sly smile and walked towards the basement door. "It's through here." He opened the door and descended down followed by Mash then Asia.

The others looked between each other skeptically but followed the trio. As they reached the bottom the devils noticed the magic circle in the center of the room. "Ara ara. I didn't even sense any magic down here. I was beginning to think you were bringing us down into your private sex dungeon, not that I would complain." Akeno teased.

Issei became flustered and tried to change the subject. "A-anyways, everything is prepared, right Da Vinci?"

The hologram appeared next to the magic circle. "Everything is all set. We're just awaiting your arrival." Confirmed Da Vinci. Issei nodded and walked into the circle followed by Mash, Asia, and Rias. Not long after the rest also walked into the circle and the magic circle began to glow. In a bright flash the group were sent to Chaldea.

After the light from the teleportation faded the group found themselves in a big room constructed for the exclusive use of going between the two worlds. In the room waiting for them was Da Vinci. "Glad you all made it in one piece. It's good to see you again in the flesh Fujimaru-kun."

"It's good to see you too Da Vinci-chan. You're looking as radiant as ever." Issei flattered.

"Ah yes, it's good to have someone around who appreciates beauty. You really know how to make a girl feel great Ritsuka." Da Vinci said happily.

Rias walked up to Da Vinci and held out her hand to shake. "It's nice to meet you in person Da Vinci-chan. I'm grateful that you were willing to help me with my own personal problems."

"It's no problem Ms. Gremory. Like I said before it's not like there isn't anything in it for us. Just remember this favor for later in case we need some help in the future." Da Vinci said with a wink, shaking her hand.

Rias nodded, then looked to Issei who walked up. "So let's get started. We have a lot of planning to do before we get to training." Said Issei.

"Before that, would you mind coming to the command room first?" Asked Da Vinci. Issei looked puzzled but nodded. As everyone was walking through the hall the ORC were looking around at the facility they were in. To them it was like being on a field trip to a scientific facility. As they reached the command room they stopped outside. "Give me a moment before you come in." Da Vinci said and walked in the room.

Everyone was waiting outside wondering what was happening. Issei looked to Mash to see if she knew but she seemed to be lost as well. After some time the door to the command room opened and Issei took that as his que to walk inside. The others followed suit and walked into the dark room. Before they could question anything the lights flashed on and party poppers were released.

"Welcome back Fujimaru Ritsuka!" Was cheered by all the staff and several attending servants.

Issei was taken by surprise as were the others that were with him. Da Vinci walked up with a bright smile on her face. "The staff wanted to welcome you back since they were all so grateful after you saved humanity. Since our time was cut short after you came back they wanted to celebrate with you properly this time."

Issei started tearing up a bit at the staff's actions and Mash walked up beside him and smiled as well. "Thank you everyone. I told you I would find a way back but I wasn't expecting such a warm welcome." Issei said with a wide smile.

The staff smiled back, pleased their surprise went over well. Da Vinci then addressed the group. "Since you have business to take care of we'll leave you to it, but during dinner we will be having a feast to commemorate your return."

Everyone nodded in agreement to the plan. The ORC were a bit surprised at how close the staff was to Issei. Normally organizations keep things strictly professional, but the staff here seem to all be friendly and comfortable with each other. Rias wondered if the Devil government could become like this in the future with the push that the current four Maoh are trying to implement.

With that out of the way the group relocated to an auditorium so that they along with many servants could be in the room without being too crowded. The ORC were amazed at all the different types of people in the room. They ranged from warriors to witches to beasts and Gods. They came to realize once again just what kind of power Issei commanded. Once they got everyone settled in, Issei and Rias walked to the front of the room to explain the situation. "All right everyone, listen up! I'm not sure how much you heard from Da Vinci about what's going on so we are going to explain what's happening and how we're going to move forward." Issei spoke loudly to make sure that everyone heard him. He and Rias took turns explaining the match and the reason behind it as well as the results of winning and losing.

One of the servants seemed to be worried about what would happen if they lost. "So you just bet us to serve some asshole if we don't beat him?" Asked Osakabehime nervously.

"Technically yes, but we won't lose. Honestly all it would take to win would be one shot from Artoria's Noble Phantasm and we would win instantly. But what I had in mind would be to do something to prevent a similar situation from happening again." Said Issei with a smug look.

The servants had a look of surprise. Considering this is the first time they saw their Master since he disappeared, some noticed that he carried himself differently than before. While everyone was taking this in, another servant spoke. "What exactly is the purpose of our participation? Why should I be involved in the fighting or as a betting piece?" Said Gilgamesh, annoyed.

Rias looked down slightly ashamed. She didn't have anything to offer these great heroes, nor did she believe they would want anything from her. Issei spoke up in her defense. "There is no tangible benefit for this in particular." The servants were looking at Issei, surprised at his blunt answer. Even Gilgamesh wasn't expecting that. "This is more to lay the foundation for future benefits later on between Chaldea and the Factions of my world. I'm also doing this as an apology to Rias-senpai, for my poor treatment of her when we first started conversing. I can understand if you don't want to help, I'm honestly fine going forward and helping her without any of you. What happens with this won't affect the Human Order or save the world. All I can do is ask that you help me, help us. Please." Issei bowed to his servants.

Rias looked at him amazed at his words and grateful. She then walked next to Issei and bowed as well. The servants looked between each other and smiled. Despite his changes on the outside it was clear that he was the same caring person he was before. Gilgamesh showed a small smile. "Tch. Seems you're doing as you please with confirming with your king first mongrel. I will overlook it this time in light of your return, but I may not be so generous next time."

Issei looked at Gilgamesh with a wry smile. "Thank you King of Heroes." The other servants laughed at the interaction before getting back on track. "So for the match we are limited to a group of sixteen people including Rias and her peerage. Between them, myself, and Mash that's seven spots taken. So only nine of you will be participating in the match and we are currently going to go over what we are up against so that we can form the best team to counter Riser's."

A servant in the back raised their hand to interject. "Master, you said something earlier about making sure a situation like this doesn't come up again. What do you mean by that?" Asked Rama

Issei pointed to his servant with a smile. "I'm glad you asked Rama. Simply put, as I said earlier most of you here could easily deal with this by yourselves, but that wouldn't prove anything to those who we are opposing. Even if we break off this arrangement there is no guarantee it wouldn't happen again. And the next time they would be smart and not let you all participate to lower Rias' chances. So we need a victory that properly shows that Rias and her peerage are capable of fighting for themselves and are smart enough to use the advantages given to them. So even while we devise our battle plan the main task I have for you all who will take part is to back up Rias and her peerage and to not let any of them retire. That is also why I brought them here. To train in our facilities and alongside those who would take part. In the end we will lose if Rias is defeated, so making sure that she not only lasts but can defeat the opposing king is key to preventing a similar situation from happening in the future, or at least to make them think twice about it."

The servants nodded in agreement to Issei's plan while Rias and the ORC were surprised he thought so far ahead. They showed a grateful smile to Issei for giving them this chance and going above and beyond what he has to do. After everyone settled down again Issei turned it over to Rias who began to explain the details of their opponents. "Riser Phenex is a high class devil who wields the power equal to that of the mythical phoenix. This means he has great control over fire and wind, and is also capable of regeneration. His regeneration is the most troubling thing about him and has basically made him undefeated in official Rating Games in the Underworld. His record is 8 wins and 2 losses and those two losses were matches he threw for the sake of other families his family are friendly with. As far as I'm aware the only way to defeat him with his regeneration is either to break his will to fight or to hit him with an overwhelming god level attack that would take him out before he can regenerate." Rias had a dark look on her face just thinking about how difficult it would be to defeat Riser.

One of the servants raised their hand which brought Rias out of her thoughts. "If it's just breaking his will there are many ways to do that, ufufufu." Said a small servant that looked like a little girl.

"You have an idea, Assassin of the Nightless City?" Asked Issei.

"Yes Master. If we could restrain him then all we would have to do is torture him with constant intense pain. Having him experience a living hell where he could never die and only end it by him giving up would be childs play." Said the assassin.

"W-while I agree that would work functionally, it wouldn't be good for the relationships between families moving forward. Even if I don't marry we still have to keep up some semblance of respect. Also that wouldn't work with Issei's plan to prove that I can handle him myself." Rias said somewhat nervously at the servant's excessively violent suggestion. If she looked out of the corner of her eye she could see Akeno looked a bit disappointed that they weren't going with that plan.

Another hand was raised. "Master, why don't we simply slow or stop his regeneration all together?" Asked Mephistopheles. "I have a skill that can temporarily weaken the effects of healing abilities."

"Uhm, if it's anti-healing skills that are useful then I have one too." Said Bunyan nervously.

Issei and Rias looked between each other and smiled. "That sounds like a good plan Mephy. That would be useful in making Riser vulnerable so that Rias can defeat him, but we'll have to play it right. Doing that tactic right off the bat might make him play more defensively which would complicate things." Said Issei.

"I think it will work out Issei-kun. If regeneration is slowed down enough a competitor can be eliminated from the Rating Game before they heal so it should be fine." Said Rias.

Everyone nodded at that and Rias continued on to explain the rest of Riser's peerage. She broke down how different Evil Pieces have different properties and what each member of Riser's peerage specialized in. Eventually Rias got around to explaining Riser's queen. "Yubelluna is Riser's queen and is known in the Underworld as the Bomb Queen. Her magic specialty is explosion magic which can cause devastation on the battlefield. She is the most dangerous member after Riser himself so we should be wary of her."

"Besides her attack power, is there anything else to worry about her?" Asked Artoria.

"Yes, she also has sealing magic that can seal one's movements and abilities until she is taken out." Said Rias.

Everyone was thinking about how to avoid that when someone else in the group raised their hand. "Well all we need to do is distract her so that she either can't seal someone or seals someone who will serve as a distraction while she is taken care of."

"That's a good idea Merlin. Honestly as far as I can see we need to disrupt the formations of the enemy and wear down both the king and queen." Issei went into contemplation for a bit before continuing. "We need to split up the peerage and attack in groups as well so that we keep them from regrouping with Riser to create a stronger formation."

Emiya, who was at the side of the room, decided to speak up. "Whatever servants you choose need to have good support skills as well as fire support. Servants who could go in and disrupt groups would also be useful."

Issei looked across the room to see who would match that criteria. After looking around, Issei made his decision. "All right. I've decided who will be a part of the team. It will be Mephistopheles, Bunyan, Emiya, Artoria, Enkidu, Berserker of El Dorado, Medea Lily, Altera, and Ishtar/Ashtart (Aka: Space Ishtar) will be taking part. Any objections?" No one seemed to disagree so the team was chosen. "All right, now that we have the team we will begin planning and training for the match that is ten days from now. I would like the servants who are good at planning tactics to take part in planning the course of action we will take against Riser as well as go over the information that Rias-senpai brought. Anyone else who wishes to take part in the training is also free to do so."

After the announcement the servants dispersed leaving only the ORC and the servants who will take part in the battle. Rias walked up to the servants and bowed slightly. "I thank you all again for being willing to help me in my family drama. I will do whatever I can to make it up to you."

Artoria waved her off. "There is no need for that. Master has decided to aid you and my blade is to do what he wishes. So if he wants to help you then that is what I will do. The same is true for the rest of us as well." The other servants nodded in agreement to Artoria's words except Mephistopheles.

"Well that might be true for the rest of them but I'm just doing it because it seems interesting." Said Mephistopheles nonchalantly.

Rias had a grateful look on her face. "Well whatever the reason I still thank you."

Everyone smiled and got ready to train. As Issei was leading the others to the operations room they discussed how they will be training. "So first in these facilities we have multiple training scenarios that we use to empower the servants. So I was thinking that it should work double for you all. It will give you practice against fighting enemies with different skills and we can collect resources to empower the servants taking part as well."

Koneko, who was listening intently to Issei's explanation, cut in when he spoke about gathering resources. "You aren't just using us to get things for you, are you?" She accused.

Issei put a hand on his chest and overdramatically looked affronted. "I would never. The point is to have you fight something that is seriously going to fight back, along with having a wide variety of enemies and strategies to deal with. Getting the resources is just a bonus since grinding is a pain in the ass." Issei said half jokingly. The others looked at him slightly skeptical of his reasoning but did admit there was logic to his plan. "Anyways I will let Mash take it from here. There are some things I need to take care of first since I'm back for the first time in a while. Emiya, I need to borrow you for a bit as well." Emiya nodded and they left the group.

As they left Rias looked to Mash. "What is Issei-kun going to do?" The rest of the ORC were wondering that too.

"Hmmmm… He is probably going to meet with Scàthach since she and Emiya helped train him in his current fighting style." Replied Mash. The ORC were stunned that Issei received training from Scàthach, someone who is known to only train those she deems worthy and is responsible for legendary heroes in Irish mythology like Cú Chulainn and Fergus mac Róich. Suddenly his skills with weapons and runic magic seemed to make more sense to them. They continued to mull over this as Mash led them onward.

Issei and Emiya were walking through the hall heading to where Scàthach usually hung around, when Emiya decided to ask Issei something. "Master, what exactly are you planning?"

Issei turned his head to Emiya. "I want to have a match with you and Scàthach-shisho to show you both how far along I've come since I left. I know it wasn't that long for you all here but for me it's been months and I put myself through some, extensive, training."

Emiya seemed to understand and showed a confident smile. "Well, I look forward to how far you've come then."

The pair walked for a while until they came to the cafeteria. Sitting at one of the tables was Scàthach who seemed to be relaxing. Once the pair started approaching her she turned to them and smiled. "It has been a while Master. Have you come to say hello?"

"Well, that and another thing." Issei looked at her seriously. "Shishou, I want to show you and Emiya how far I have come while I was away."

Scàthach showed an amused smile. "Oh? How interesting. Well then, let's see how strong you have become." The three left the cafeteria after that.

Mash was waiting in the operations room with the other servants as the ORC were changing into combat gear provided by Chaldea. After some time everyone gathered together to start the training. "So as Senpai said there are various training simulations that will provide different experiences. The resources that drop from these enemies are divided by three categories. The first is Ember Gathering which helps empower servants. Think of it like gaining experience points for servants. The second are the Training Grounds which gain materials to help servants ascend to more powerful forms. Finally there is the Treasure Vault which gathers QP or Quartz Points which is used as a catalyst to use the other resources. On top of that the specific type of resource correlates with what class they are."

Asia raised her hand. "What are classes?"

"Servants are separated into different classes which can determine what their abilities are. Heroic Spirits usually have a long history of adventures and achievements which allows them to manifest into different classes. This also means that the servants are usually not at full power since they are restricted to their abilities that are associated with their class. For example, King Arther could manifest in the Saber class, the Lancer class, or the Rider class since he wielded Excalibur and Rhongomyniad respectively and was proficient in horseback riding. There are many classes but there are 7 main classes. These are Saber, Lancer, Archer, Rider, Caster, Assassin, and Berserker. There are extra classes as well but they are less common so only certain individuals can appear in those classes. The different simulations vary based on the 7 main classes and the three categories have certain enemies in each. The Training Grounds have the most variety with enemies of a certain class, including enemy servants, while Ember Gathering and Treasure Vault have the same type of enemies with varying power."

The ORC were staring at Mash in awe as she explained the different training facilities. It's no wonder Issei and Mash were able to make short work of the Fallen Angels and the Stray Exorcists. With facilities like these anyone would become powerful. Rias now had all the pieces to understand why Issei was so confident in their victory. "We really don't know anything do we?" Rias asked no one in particular.

The ORC looked at her confused but then understood what she meant by her statement. Mash looked at her with a kind expression. "Sometimes ignorance is bliss. Despite all that we have here, the inner workings are entangled in dark dealings as well as depravity. Some would call it a necessary evil to protect the greater good but that will be determined by the results I suppose." Mash said, her look becoming melancholy. The ORC looked at Mash worried at her change in mood but she shook it off and got back on track. "Anyways we should start training now. I'm sure Senpai will join us once he is done with Emiya-san and Scàthach-san." Everyone nodded and training began.

(Later that day)

Issei was currently trading blows with Scàthach and Emiya. The two weren't going all out but were pushing Issei to his limits. Issei was able to keep up with Emiya's Unlimited Blade Works with his weaker version that he learned from him. At the same time Issei was using the lance fighting style and runic magic that he learned from Scàthach to trade strikes with her. Needless to say, he was having a rough time.

"You seem to have gotten better since the last time. I would say your form is sloppy but it seems more like you took my fighting style and started mixing in your own personal style with it." Scàthach commented.

"I'm inclined to agree. Your use of projection has improved and you have found good ways to use your weapons creatively. It helps that you're able to compensate for the copies weaker power by boosting it with your Sacred Gear." Emiya praised.

Issei was breathing heavily, clearly exhausted from the exercise but not dropping his stance. "Thanks. Like I said I haven't stopped my training even after I went home. I need to be stronger than this if I want to properly stand beside everyone."

Scàthach showed a wry smile. "We keep telling you, you don't have to go that far, but seeing how much you care is comforting at least." She gave him a discerning look. "So, how long are you gonna hold back your real power?" She asked.

Emiya looked confused while Issei showed a defeated smile. "Can't get anything past you, can I shishou?" Commented Issei. "I was fighting in my base form because if I improve that my full power gets stronger as well. On top of that I wanted to see how far I've come since the last time, but I guess now is a good time to show you, just how strong I've truly become."

Issei stood straight and held up his Boosted Gear in front of himself. Power began to well up around him in a red and green light. "Here I come, Scàthach, Emiya!"

Some time later after everyone went through the various training simulations they were being shown around Chaldea and to their quarters where they will be staying for their time here. As they were walking Kiba decided to ask what was on all their minds. "I wonder where Issei-kun is? He never showed up for training."

The rest of the ORC nodded in agreement with Kiba and Mash looked curious as well. "Well, if he is training with Scàthach then they are probably in a different simulated space. Some servants are powerful enough to create their own spaces or open gates to other places. Scàthach can create a path to the Land of Shadows, which is her domain."

As they were walking they came across some people in the hall. It was Issei, Emiya, and Scàthach but Issei was a bloody mess and being supported by Emiya. The others were staring at Issei in shock while Issei weakly lifted a hand. "Hey guys sorry I took so long."

"Issei-san!" Said Asia worriedly. She immediately moved to his side and started to heal him.

Everyone was worried about Issei as Mash went up to Scàthach. "What happened to Senpai!?"

Scàthach just smirked while she responded. "He wanted to show us how far he had come so we just upped the intensity of his training a bit, that's all." She said nonchalantly.

Everyone was stunned he got this beat up from training. Issei tried to assuage everyone's worries. "Don't worry guys. I just went a bit overboard that's all. Besides I knew Asia was here to heal me so I just held back less."

Everyone stared at Issei, a little exasperated at his recklessness. Mash walked up to him and hugged him. "You shouldn't be so reckless Senpai. What if something happens to you before the match? How are you going to help anybody then?"

Issei, now fully healed thanks to Asia, gently pat Mash's head. "Sorry Mashu. I'll be more careful."

As the two were enjoying the moment Scàthach decided to interrupt. "So you two finally got together. Took you long enough." She said with a sly smile.

Issei and Mash blushed heavily at her comment while everyone one else showed a wry smile. Issei, trying to disperse the awkward atmosphere, tried to change the subject. "We should head to the cafeteria for the welcome back dinner."

Everyone nodded in agreement and left for dinner. When they arrived in the cafe all the staff and many servants were there getting things ready. Some were in the kitchen cooking while others were setting up the space for everyone to have a good time and be a little rowdy. When they walked in Issei offered to help but was stopped by Charlotte Corday. "This is a party for you Master. You should just sit and relax with your friends." She said cheerfully.

So Issei and the others sat at one of the tables together watching everyone work and talk amongst themselves. Soon more people and servants were entering the cafe and everything had been prepared. Once everyone was in attendance Da Vinci gathered everyone's attention. "Attention everyone! I'm glad you all could take time out of your busy schedules to be here. We all are gathered here to celebrate the return of Chaldea's Master, Fujimaru Ritsuka!" She extended her arm out in Issei's direction and in response Issei stood from his seat. "This gathering is not only to welcome him back after returning to his home but to celebrate the success of our mission to save humanity. Our Grand Order was completed and with the defeat of Beast I the threat of the Demon Gods has ended. So now is the time for us to kick back, relax, and enjoy the fruits of our labor!"

"Cheers!" Everyone in the cafeteria cheered.

The staff, the servants, and the ORC were all eating and being cheery during the celebration. At some point Issei was dragged off by some of his servants and Mash followed behind leaving the ORC on their own to interact with the people of Chaldea. Kiba was talking to some servants with impressive swords, Koneko was interested in the more animalistic looking servants, Asia was talking to a group of people who looked like knights, and Akeno was currently speaking with a shirtless man with a scar on his chest who was clearly hitting on her. Rias was looking around, not sure what to do. She didn't know who to talk to first and Issei, Mash, and her peerage were busy. As she was contemplating what to do, someone walked up to her. It appeared to be a woman who had short salmon colored hair with pointed ears and a cloak made of feathers with a white dress underneath as well as a feather hair ornament. She held a staff in her hand that she didn't recognize the design of in one hand and a plate of food in the other. "Hey there. Is this seat taken?" She asked politely. Rias shook her head and held out her hand implying for her to sit. "Thanks. It's nice to meet the woman of the hour." She said casually.

Rias was slightly confused at her statement. "What do you mean? This party is for Issei-kun."

The lady sat down, her staff disappearing somewhere and put her food down. "Yes, while this party is for the little Master I'm talking about you and your situation." She said smiling. Rias look down a mix of embarrassment and slight shame. "Since Master is helping you I'm assuming that you wish to be with him, right?"

"Well, it's a bit more complicated than that." Rias said. At the woman's look of interest Rias explained the plan Issei came up with.

"I see. So then what is your next step after you're free? Do you plan to confess to Master?" The woman said almost knowingly.

"I-I don't know. Issei-kun has been a great help to me and has been accommodating despite everything he has been through. He already has Mash and even if he wants a harem he seems to think that I'm not really interested in him. He said that if I wanted to continue the relationship afterwards I would have to say it to him myself, but I'm not sure that's what I want."

The woman stared at Rias a bit before sighing. "Look little miss. Take it from someone who has been in your position before. If it's something you want you should go for it. If you spend your time getting hung up on the possibilities and being too afraid to act you may find that you lost your chance at being happy." The woman looked slightly downcast. "There was a man I loved once. He had washed ashore on his boat with some of his men, lost and in need of food and materials to repair his ship. I took care of him during his stay and tried to convince him to stay on the island. But he was already married and his only goal was to return home to his wife." Rias was listening intently to the woman's story. "I tried all sorts of things to convince him to stay but he rejected it all. He wasn't mean at all either which only made it more irritating. Eventually his ship was repaired and he set off back to try and return to his homeland. During that time I never confessed my feelings for him and I carried that sadness with me to my death." She recollected herself before continuing. "After I got summoned by Master I was able to meet with that man again. He too was summoned as a hero and after fighting alongside each other I was more or less forced to confront the feelings that were bottled up inside for so long in my life. I finally confessed my feelings to him and while he was happy I felt that way, he couldn't accept them for he only loved his wife." Rias wasn't sure what to say. The story didn't go in the direction she was expecting it to go. "You are at a crossroads right now. Once you are freed from your obligations you should do what your heart desires. If you get caught up in all the possible drama you will never get what you truly want. If you want to be with Master then don't just go for it. Go for it with all your being!" The woman said a certain intensity in her voice in the end.

Rias was slightly taken aback by the woman's passion but decided to take what she said to heart. Issei did mention before that many of the heroes died while holding on to regret and hearing such a tale directly from one gave her a lot to think about. "Thank you. I will take your advice to heart, Miss… It just occurred to me that I don't know your name."

The woman smiled. "Most people around here just call me the Witch of Okeanos. Even Master doesn't know my true name yet. Or maybe he does. I wouldn't be surprised if Odysseus told him in casual conversation. Well either way you can call me that or Queen Witch."

Rias had an amused look on her face. "All right then. Thank you for the talk Miss Queen Witch. You have given me a lot to think about."

"Glad to be of service. If you need some lessons in magic I would be glad to be of assistance, as a fellow maiden of love." The Queen Witch said playfully. The two then had a nice chat about other things.

The dinner party went on late into the night and Issei, Mash, and the ORC were heading to their rooms. Kiba and Koneko had broken off from the group to go to their rooms and the next room up was Issei's. "Well this is my stop. I will see you guys in the morning. Good night." After saying that, Issei walked into his room. The automatic door took a bit to close after he walked in and he felt a few presences behind him. "Uhhhh… What are you all doing in my room?" Asked Issei confused.

Behind him was Mash, Rias, Asia, and Akeno. They followed him into his room. Rias spoke first. "I'm a bit nervous sleeping alone here. It's not that I'm afraid of being assaulted or anything, this place is just, a bit much for me." She said nervously.

"I came in because Rias followed you in." Said Mash.

"I came because it seemed like something interesting was happening. Ufufufufu." Akeno said while laughing.

"I-I came in because the others followed you in too." Asia said sheepishly.

Issei sighed. "So… What happens now? Are we all sharing a room tonight?" He said playfully, wanting to see what their reactions would be.

"I'm fine with that." Said Akeno without hesitation.

Issei, Rias, and Asia looked at her surprised. "Akeno!? What are you talking about? Why would you want to sleep with Issei?" Asked Rias, a little annoyed.

"Simple. I think he's cute and manly." She said matter of factly. Issei was stunned. He couldn't tell if she was just teasing him or if she was being serious. Akeno walked up to Issei and put her face close to his and a hand on his chest. "When I saw how you stood up to Riser for Rias' sake it got me all excited. You showed that you wouldn't be swayed even in the face of someone who could kill you. Since you want to have a harem, it shouldn't be a problem adding me in after Mash, Rias, and Asia right?"

Asia started blushing intensely when Akeno added her in with Issei's women. Issei just looked slightly perplexed. "Why does everyone keep adding Asia in when talking about my harem? I take care of her and try to make sure she is happy but we aren't going out."

All the girls were staring at Issei with Mash and Rias being a bit exasperated at his denseness, Asia looking slightly downcast, and Akeno being surprised. Akeno looked between everyone to see their faces. "Ara? I thought Asia and Issei-kun were together seeing how close you two are."

Asia waved her hands in front of her. "Ah! No! Issei-san and I are just… good friends." She said somewhat dejectedly.

Akeno looked at her then turned her gaze to Mash and Rias who looked a little sorry for her. "Did I perhaps go too far?" She asked apologetically.

Mash and Rias looked between each other and nodded. "Actually Akeno, why don't you and Asia sleep with us tonight?" Rias asked.

Issei was stunned at the escalation of events happening in front of him. Akeno and Asia both had a look of surprise on their faces not expecting Rias to welcome them when she looked like she was about to argue against them being here. Asia started fidgeting in place. "W-well if Issei-san is ok with it then…" Asia said her voice fading.

Akeno was looking at Rias then turned to look at Issei, whose expression showed he was lost as to what was happening, then back to Rias. She seemed to understand something then finally responded. "Ufufufufufu. If it's a request from my King, how could I say no?" Akeno said in her usual refined manner.

Issei now looked happy about the situation but a thought occurred to him. "Uhm… If we're really doing this we're going to have to figure out how we're all sharing the bed." He said while looking at his bed. The standard issue beds for Chaldean staff was a queen sized bed, which is more than enough for one person but a little cramped for five people.

Rias looked between them all before answering. "Don't worry about it Issei, just leave that to us. Why don't you go get changed while we figure it out?"

Issei went into the bathroom to change, leaving the girls to themselves. "I knew Issei was a bit on the innocent side but I never imagined he was that green." Said Akeno.

Rias had a complicated look on her face. "He has never had experience dealing with girls until us so it's no surprise that he has a hard time reading hints. Especially since most girls would never give him a hint in the past due to his, personality." Akeno nodded in understanding while Mash looked upset and Asia looked confused.

"What's wrong with Issei-san?" Asked Asia innocently.

"There is nothing wrong with Senpai. It's just that people tend to judge too fast before getting to know someone and by proxy, never give them a chance to show who they really are." Said Mash sadly.

Rias put on a determined face. "In any case, we have to show him that we are seriously interested in him and teach him the subtleties of women. It is a necessary skill if he wishes to be a harem king."

"But polygamy is against the Lord's teachings." Said Asia.

Akeno looked at the former nun with an amused smile. "Ara ara, Asia you have already reincarnated into a devil so I think it's a little late for you to have to worry about going against the teachings at this point."

Asia seemed to realize that now that she was a devil, no matter what she did she would end up in the Underworld in the end. She began to feel saddened by that but then remembered what Rias was saying earlier. "I-is it really ok for me to be with Issei-san?"

Mash walked up to Asia and grabbed her hands. "It's fine Asia. You are like me in many ways and I have a feeling that your feelings for Senpai are the same as mine." Mash said supportively. Asia looked happy at those words and her worries were assuaged.

Rias nodded her head, happy at the result of the conversation. "Good. Now with Asia on board we will be able to have Issei acknowledge us as girls who seriously want to be with him."

Akeno looked at Rias confused. "Us? Aren't you already dating Issei-kun?"

Realization dawned on Rias. "Oh! That's right. We never got around to telling you because of how hectic today was." Rias explained Issei's plan to Asia and Akeno. Needless to say, the two were surprised.

"Ara ara. So you two were faking it the whole time. I never would have guessed. Does that mean you two haven't actually slept together?"

"We've slept in the same bed but if you're asking if we've had sex, then the answer is no." Said Rias.

A mischievous look appeared on Akeno's face. "Then Issei-kun is still a virgin then. Maybe I should take his first time."

Rias showed an unamused face. "Issei is not a virgin. He has done it with Mash multiple times."

Akeno was surprised again, thinking that with how green Issei is to relationships that he was still a virgin if he didn't already do it with Rias. "Ara ara, I didn't think you had it in you Mash-san." Mash was blushing heavily at Akeno's words. "In any case, since he has done it with Mash-san I figured you two would have at least done it once."

Rias had a small blush on her face. "Well, before Issei made the plan I offered him to take my virginity before Riser could to hopefully stop the engagement, but he denied it saying that my first time should be with someone I want to do it with and not as some obligation or a method of escape. And even though we have been going out together this past month and he has been treating me as a real girlfriend he thinks that I'm only putting up with it to get out of the engagement and not because I like him." There was a hint of disappointment in her voice as she spoke. "After our first date Issei said that if I wanted to continue being with him after all was said and done then I would have to ask him out."

Akeno showed an amused smile. "Now that is something I would like to see." She said teasingly.

Mash decided to say her piece. "Senpai has always been a straightforward person. He can read subtleties when it comes to basically anything but love. He always knows what to say which is why he has managed to get so close to the servants and why they adore him. But when he saw issues that were related to love among the servants his usual comment was "Why don't they just go up and talk to each other?". Granted he wasn't so dense as to stick his nose in where it wasn't wanted so he understood that much at least. He was also more aware of love during the Valentines Day Event as well."

The girls were confused at what Mash meant by Valentines Day Event but took in the rest of what Mash said before Asia decided to speak up. "T-then we just have to tell him to his face, right?"

The girls were surprised at Asia's sudden forwardness but Rias had a complicated look on her face. "I'm not sure how effective that will be. He tends to think that we're messing with him when we say things like that. The only people he seems to believe their words 100% of the time are his servants."

"The servants here have rather blatant personalities. So it's easier for Senpai to recognize and get along with them even if their personality is all about deception. On top of that, Senpai has history to fall back on if he needs to know more about a servant so he takes what they say in stride. You all are something of a new experience for him, being people he has no previous knowledge of and no information to fall back on, so he's skeptical of everything you do." Clarified Mash.

The three looked between each other before Rias spoke. "Then we just have to show him we can be as open to him as his servants are." The three devils nodded in unison as Issei walked out of the bathroom.

"All right. The bathroom is free for you girls to change and shower in." Issei said as he walked out.

Rias went in next while Mash, Asia, and Akeno left the room to get their sleepwear from their rooms. As Issei was waiting for everyone he decided to sit at his desk in his room. Fou appeared and curled up on his lap, getting comfortable. He opened a drawer and grabbed his tablet that was provided to him by Chaldea when he first got here. He decided to brush up on some old Magecraft lessons as he waited. He opened his file of, Lessons in Magecraft: Mana, and began studying. About 20 minutes passed before Rias finally got out of the bathroom. She saw Issei reading at his desk and walked up to him in her usual red negligee. "What are you reading?"

Issei looked at Rias, quickly looking her up and down before answering. "Just brushing up on my Magecraft while I wait. Refining my power will help in the match to come."

Rias nodded in understanding. "Oh. By the way, I told Akeno and Asia about the plan, since we already accomplished what we were planning with getting you guys in the match."

"Ah! Right, I forgot about that part. What did they say?"

"They weren't upset or anything, just surprised that we weren't actually dating."

"It just means we did a good job convincing everyone." Issei said with a smile.

Rias smiled sadly seeing that Issei didn't seem to think Rias enjoyed herself with him. "Yeah, well the next step after the match will be my parents."

"Yeah, well, I have some choice words for them." Said Issei slightly irritated.

"Don't be too rash or you might set things back. Although your willingness to defend me is appreciated." Rias said with a blush.

"Right, sorry." Issei looked at Rias thoughtfully before asking her something that had been on his mind for a while. "Hey Rias. Why haven't you tried something like this with Kiba?"

Rias looked surprised at the sudden question but answered. "Yuuto-kun is too noble a person to do something like this. He would defend me with his life but he's not good at deception for the most part. That aside, even though he is handsome he's not my type."

"So I'm your type?" Issei asked, a mix of surprise and happiness.

Rias blushed. "Well, I always thought you were cute, in a little brother sort of way. But the thing that caught my attention before you disappeared was your honesty." Issei looked at Rias curiously wondering what she meant. "Despite being a pervert you were never malicious towards girls. You never tried to force yourself on girls nor were you overly crude to anyone. You were unashamed to say what you liked and I guess that drew me to you since I've spent my life around people who always tried to put up a front in order to get on my good side. Peeping aside, you were a pure boy that was simply misunderstood." Rias had a bit of a sad look on her face. "Looking back on it, when I heard you disappeared I was quite worried. Not just because of the threat of something in my territory but because there are so few people like you. I also felt sad when you came back and you were clearly changed. I was hoping that your experience didn't change your honest personality. I don't know why but I felt relieved when I saw you didn't change too drastically. I didn't understand it then but after spending time with you these past few months I think I've come to understand what this feeling is."

"And? What is it?"

Rias gave Issei a bright smile. "When we win the match with Riser I will tell you. How does that sound?"

Issei pouted a bit. "You're just going to leave me hanging?"

"A girl has to keep some things to herself. Although you are free to try and figure it out for yourself." Rias said playfully.

They shared a smile then the door to the room opened. Mash, Akeno, and Asia all came back in their pajamas and with a change of clothes for the next day. Once they all gathered, Issei asked the million dollar question. "So, how are we doing this?" The girls looked between each other before looking at the confused Issei.

After a few moments they were all in bed together. Issei was in the middle with Rias and Akeno on both sides of him, while Mash and Asia were on top of him resting their heads on his chest. Under most circumstances this would be uncomfortable but Issei was too busy enjoying the sensation of the four girls' bodies to care about that at the moment. This is the best moment in my life after losing my virginity! Issei thought to himself. The girls could see the happy expression on Issei's face and smiled themselves. "Well? Is it everything you hoped it would be?" Asked Rias playfully.

Issei nodded his head with happy tears coming down his face. Akeno gave a small laugh and snuggled up closer to Issei. "Ara ara, Issei-kun is with four beautiful girls so of course he would be happy. I wonder, if Issei-kun would like to enjoy himself with all four of us tonight?" She teased.

Asia blushed intensely while Issei's brain almost short circuited from Akeno's suggestion. Rias didn't look to be against it but Mash felt differently. "Now is not the time for that. It's already late and we don't want to be exhausted for training in the morning so we should get some sleep." She said. Issei was brought out of his thoughts and agreed with Mash. The others agreed as well and they all went to sleep for the night.

(9 Days till the match.)

Issei was stirred from his sleep. He felt heavy but remembered it was because he had four girls pinning him down. He looked around and saw that they were asleep still. As he continued to look around he saw someone standing next to his bed. She was blonde with her hair in a bun and an ahoge with a red dress with white frills at the end and gold trim along the skirt. The front of the skirt was transparent white which allowed people to see what was underneath. "Good morning Praetor." Said the girl energetically.

"Nero? What are you doing in my room?" Issei asked, still a bit groggy.

"Umu! I came to wake up Praetor but what do I find but your bed full of women. If you wanted women in your bed you could have asked me, you know." She pouted slightly.

Issei smiled slightly. "I wouldn't be against it. Now that I have more freedom and the ability to pursue my dream I would gladly welcome you into my harem."

Nero had a surprised look but then it turned into a bright smile. "Oh! Praetor, so you have finally fallen for the charms of the Rose of Rome. It's no surprise considering I'm one of the most beautiful women of Rome. Umu!" Nero puffed out her chest.

Issei laughed slightly at Nero's usual antics. To the sides of him both Rias and Akeno stirred. The pair of beauties lifted themselves up and saw Nero and Issei talking. "Ara ara. Issei-kun is talking to other women while laying next to some. How bold of you." Akeno teased.

Rias looked at the new arrival. "Who is this Issei?"

Before Issei could answer, Nero spoke first. "Umu! I am the one and only Nero Claudius, Emperor of Rome!" She announced herself proudly.

The pair shared a surprised look at meeting Emperor Nero in such a way, although they should be used to Issei having such people by now. "It's an honor to meet the Emperor of Rome. I am Rias Gremory and this is my queen Akeno Himejima." Rias introduced herself and Akeno.

Nero examined the both of them then seemed to nod in approval. "Umu! You two are definitely worthy candidates to be Praetor's women. I approve as your wife Praetor." Nero said proudly.

The two devils looked between each other before saying "Wife!" loud enough to wake up Asia and Mash. "Waaa… What's with all the noise?" Mash asked, yawning as she talked.

"Mashu! Did you know that Nero was Issei's wife!?" Rias asked panickly.

Mash seemed to be more awake after the question and just sighed. "It's not what you think Rias-san. A lot of the servants have strong personalities and/or high pride that won't allow someone who isn't of a certain rank or status to be a Master of them. As such they justify Senpai being their Master by saying he is their husband or by giving him some arbitrary position."

After she explained that the devils seemed to calm down but were confused. "So then why do you believe that Issei is your husband?" Asked Akeno.

"Umu! Being his wife is the only position appropriate for an Emperor like myself. Besides we have been through much hardship together and I have seen Praetor bloom on the battlefield multiple times and stand against foes whom he had no chance against and prevail. My husband should be a man of such caliber at the very least!"

Nero was singing Issei's praises and it made him blush slightly. The three devils were staring at her in awe while Mash nodded in agreement. "Well having us be a couple would be interesting. We would be the Twin Red Emperors." Issei said jokingly.

Nero seemed to smile brightly with sparkles in her eyes. "Umu! That sounds perfect! The Twin Red Emperors of Rome would be a perfect name for us!" She was almost jumping up and down from excitement. "Oh! That's right! I should go tell the other Neros about this too. I'm sure they will be just as excited as I am, since they are me after all. Umu!" Nero said while leaving the room.

"Other Neros?" Said Rias confused.

"Yeah, it's a bit complicated but it is possible to summon multiple of the same servant. They can also be different classes as well, so having more than one of a person isn't too out of the blue. For the record there are three Neros in Chaldea, two different Sabers and one Caster." Issei explained.

"Ara ara, so that means you just got three women for the price of one." Akeno teased.

"Haha, guess so." Issei seemed slightly nervous.

"What's wrong Issei-san?" Asked Asia.

"Nothing Asia. I just have a feeling that Elisabeth Bàthory will stir up trouble because of Nero so I'm just preparing myself for the inevitable chaos." Issei said with a strained look.

The others besides Mash weren't sure what he was talking about but decided to leave it be. The five got out of bed and Issei stretched to get his cramps out from being used as a body pillow by four girls. "Senpai we should get ready for training. Since we got everyone acquainted with the training facilities yesterday, this morning is about planning with our team before fully diving into training." Said Mash.

Everyone nodded in agreement and started getting ready. Issei was heading to the bathroom to shower but was stopped before the door by Rias. "Are you going to shower? Let me go in with you." She said with a smile.

Issei was stunned at her suggestion and before he could respond the other girls jumped in as well. "T-then me too!" Said Asia nervously.

"Senpai! I will wash your back!" Said Mash intensely.

"Ara ara, then I will get his front." Said Akeno erotically.

Issei's brain was short circuiting so he said the first thing that came to mind. "I-I don't think the shower will fit all of us."

The girls looked at each other and then huddled together. They talked amongst themselves as Issei was trying to regain his composure. After a bit the girls all looked at him with a smile. "Mash and I will go in with you this time and Akeno and Asia will go with you next time." Said Rias.

Issei nearly fell over with the results of this situation. Why are these girls so insistent on doing these things with me? Mashu makes sense but there is no reason for the rest of them to go this far since I already told them I had no intention of becoming a devil. Have they perhaps not given up on that? Issei thought to himself, trying to make heads or tails of the situation.

As he was trying to think straight, Rias and Mash started pushing him into the bathroom while Asia and Akeno left to get ready in their own rooms. After a rather stimulating shower the three got ready and headed towards the cafeteria to have breakfast. When they reached there the others were already waiting for them. "Good morning Buchou, Issei-kun, Mash-san." Said Kiba with his usual pretty boy smile.

"Morning." Said Koneko in her usual monotone.

"Ufufufu, you three sure took your time." Said Akeno suggestively.

"Y-yeah well, some things happened and we were slightly delayed." Issei said, still trying to calm himself down.

Akeno gave a knowing look while Asia just looked down and blushed. Kiba and Koneko were confused but soon someone came to the table. "Good morning Master." Greeted Scàthach.

"Good morning Shishou." Greeted Issei.

"Good morning Scàthach-san." Greeted Mash.

The members of the ORC gave a greeting to Scàthach as well. After they all finished greeting each other, Scàthach looked to Issei. "What is your plan for training Master?"

"We were going to train using the Chaldea gate to up everyone's stats and to build teamwork and coordination. We are also going to have a strategy meeting after breakfast as for how we are going to deal with the individual members of Riser's peerage. Granted we won't know anything about the battlefield until the match so there is only so much planning we can do." Issei said.

Scàthach nodded her head in understanding. "I see. Well I had an idea for your training as well if you're willing to listen."

Issei cocked his head in interest. "If it's your idea I'm sure it would be helpful. What is it?"

"The day before the last day of training I want to hold a match between your team and a team of servants that I will assemble. That way you can have practice against something that is actively planning to fight against you and see where you need to improve."

The group looked surprised at the suggestion and were slightly worried considering who they might go up against. Issei on the other hand showed a fearless smile. "That sounds perfect! Of course don't be too rough on us, we still need to be in fighting shape for the match."

"That's why I suggested doing it the day before the last one." Scàthach said with a small smile.

"Ok, gather whoever you think will give us an appropriate challenge for the match and in the meantime we will prepare for it."

Issei was pumped while the others looked nervously between each other. After that they all ate breakfast and headed to one of the meeting rooms. In the room were multiple servants who were good at planning and strategizing along with the participating servants. As everyone gathered they began hashing out their plans for dealing with Riser's team. After about an hour and a half of planning they went to the operations room to begin training for the day.

After training for the day the ORC and servants were eating dinner in the cafeteria, talking about how their training for the day went. While they were talking Da Vinci came up to them. "Seems like you're all putting in good work for the match. I also have to say that we are getting a lot of good data by having all of you who use true magic practice in our facilities." Da Vinci praised.

"Did you learn anything from observing the others fighting?" Mash curiously asked.

"Nothing concrete at the moment. We still need to analyze the makeup of true magic and understand it before we can do anything with it, but this is more than anyone else in the Mages Association has ever had."

"Well I'm looking forward to your findings." Said Issei with a smile.

Da Vinci nodded then gave a mischievous smile. "By the way, Nero talked to me earlier today. She told me some, interesting things."

Issei began to sweat slightly. "What kind of things?" He said nervously.

"Oh nothing too serious. Although after we talked I had to make a slight adjustment to your room."

"What kind of adjustment?" Issei asked, his eyes narrowing. He knew Da Vinci had a habit of testing out her experiments on people without asking so he was slightly concerned for his own safety.

"Nothing too serious. You'll know it when you see it." She said irresponsibly.

Issei put a hand on his head trying to fight back the urge to complain to Da Vinci about doing things to his stuff without telling him. Mash put a hand on his shoulder supportively. "Don't worry Senpai. I'm sure it's not a big deal."

"Y-yeah. Maybe you're right." Issei did his best to try and convince himself.

Later Issei and the girls were heading back to his room when they spotted someone standing in front of Issei's room. "Emperor Nero?" Said Mash inquisitively.

Nero turned to see them and smiled brightly as they walked up to her. "There you are Praetor! We have been waiting for you. Umu!" Said Nero excitedly.

"We?" Said Issei confused. Nero gave a confident smile and led the group into Issei's room. As they walked in they saw the change that Da Vinci was talking about earlier. Issei's bed was larger than before, most likely to accommodate Issei's increasing number of women. Sitting on the edge of the bed were the other Neros (Bride and Summer versions).

"Welcome back Praetor!" Said Summer Nero.

"Or perhaps it should be welcome home darling? Umu!" Asked Nero Bride.

Issei was staring at the two, his mind trying to find the words to express his happiness at that moment but Mash beat him to the punch. "All three Nero-sans? What are you all doing here?"

"Umu! We are here to sleep with our husband, just like you all. It's the reason why we went to talk to Da Vinci earlier, since Praetor's bed wasn't large enough for all of us." Said Nero.

So that's what Da Vinci was talking about earlier. Issei thought to himself. As he was lost in thought Nero grabbed his hand and led him to his new bed. She sat him down between the other two Neros then got on the bed and crawled behind him, leaning against his back.

The two Neros on his sides were petting his face. "Umu! We should enjoy ourselves tonight my husband." Said Nero Bride alluringly.

Mash cut in at that. "No! There will be no nightly activities while the training trip is in progress. Neros, we need Senpai to be operating at 100% so that we will be ready for the match so no after-hours activities until then." She said sternly.

The three Neros pouted at that but understood. With that settled Issei went to the bathroom to shower and was subsequently followed by Akeno and Asia. "What are you two doing?" He asked.

"It's our turn to shower with you, remember?" Said Akeno. Asia had a slight blush on her face.

The Neros got up after they heard that. "No fair! You said no after-hours activities!" They complained.

"This was something already agreed upon by us girls since Rias and I showered with him this morning." Said Mash.

The three huffed and folded their arms. "Then we get next time with darling." Said Nero Bride.

"That's fine. It's only fair." Said Rias casually.

"Don't I get a say in this?" Asked Issei as the conversation was carrying on without him. All the girls just stared at him and he immediately wilted. It's not like I was gonna say no anyways. He thought to himself. He walked into the bathroom followed by Akeno and Asia. After some time the three came out, Issei having a happy expression on his face which made the other girls pout a bit. Asia was blushing intensely and Akeno seemed to have a look of satisfaction on her face. Both Rias and Mash were staring a hole through Issei which he noticed. "N-nothing happened I swear!" He said while putting his hands up defensively.

"Ara ara, there's no reason to be shy Issei-kun." Akeno teased while clinging to his back.

Rias seemed to get more upset but Mash just stared some more before speaking. "If you say so Senpai then I believe you."

Issei had a slightly surprised look on his face but then it turned grateful. He walked over to Mash and gave her a gentle hug which she returned with a smile. Now the girls were pouting for a different reason. Nero Summer got off the bed and decided to intervene. "Praetor! You are being unfair to the rest of us!" She said while clinging to him.

Issei gave a wry smile and patted Nero Summer on the head. "All right, I'm sorry. Why don't the rest of you get ready so we can go to sleep. We have a long week ahead of us." The others smiled at him and got ready to sleep.

(5 Days until the match.)

Halfway through the training trip the ORC have improved their power and coordination as a group. Many of the members have learned things from the servants they worked alongside. Kiba learned new tricks from Emiya based off of his skills, similar to that of Issei's. Koneko did her best to keep up with the Berserker of El Dorado since they were both physical fighters. Asia improved her healing abilities thanks to the help of Medea Lily. Rias and Akeno observed Space Ishtar's use of her abilities and how she swarmed the battlefield with both large and multiple magical attacks. Issei and Mash were working to help the servants coordinate better with the ORC. Overall things had been moving along rather well. Battling against real enemies had yielded better results than simple exercise and sparring.

On a side note, Issei had been spending his time when he wasn't preparing for the match with one of or a couple of girls and getting used to handling multiple women and trying to keep them all happy. Thankfully, Rias and Mash also helped mediate some of his time since he was still new to this. He was incredibly grateful to them for their help and has been getting even closer with them as a result.

Issei and Rias were currently walking down the hallway after talking with Da Vinci about some questions she had about magic. "It's so strange to be in a world that doesn't have real magic. Being asked questions about the basics seems a little strange to me, but I guess that's because I'm used to it." Rias said.

"Yeah well, when the Age of Gods ended true magic was lost to this world so it's only natural that the mages of this world would be curious when someone with true magic appears." Said Issei nonchalantly.

"Although after being in this facility for so long it feels like this world has advanced far more than ours without true magic."

"Well, when something is taken away from you you normally work hard to try and get it back. You could say this is the result of that process."

"It honestly puts into perspective that we supernatural beings severely underestimate humans."

Issei gave Rias a curious look. "I have an idea of what you mean but could you specify?"

Rias gave a slightly ashamed look. "While I can't speak for the Angel's Faction, it is generally understood by all supernatural factions that humanity must remain unaware of our existence in this era."

"Why?"

"Because it could cause the humans to become afraid of us and strike at the different supernatural factions. It would cause a new war that could lead to the destruction of all sides."

"What makes you so sure that we would just try to eliminate you immediately?"

"Humans have a history of persecuting those different from them."

"And that is different from the other races, how? Last I checked Riser seemed to look down on me because I was a "weak" human. The Fallen Angels were the same as well. Isn't it ironic that supernatural beings look down on humans yet they all seem to follow a rule to not provoke humanity so that they don't get wiped out."

Rias never really thought about it before, she had just accepted that explanation as something natural, but once Issei pointed it out it suddenly didn't make any sense. Why did supernatural beings look down on humans as weak creatures yet feared being destroyed by them? It was contradictory. "I never really thought about it before. It is the common sense that is usually taught in the Underworld and many other factions follow it as well. But now I don't know which one is correct. Are humans weak and unable to do anything to the supernatural or are they strong enough to get rid of us and should be handled with care?" Rias was showing an extremely confused expression.

Issei just shook his head. "You're looking at it all wrong Rias. While I made fun of the contradiction, both are true. Humans are weak creatures but because of that we find ways to circumvent our weakness so that we may overcome the strong. While a straight confrontation between humans and the supernatural would most likely end in humanity's loss, we are sore losers and would most likely launch nukes to go completely scorched earth. Simply put, it would be mutual destruction except for the fact that the supernatural could escape to the Underworld or Heaven or whatever planes of existences there are outside of earth."

The thought of humanity destroying the earth just to win made Rias shiver in anxiety. She realized that she really hadn't been thinking too deeply about the repercussions of her actions and had simply been doing as she was told because she was expected to do so. "Then that just means we have to maintain that secrecy in order to protect everything."

"That would only last so long." Said Issei somewhat pessimistically.

Rias looked at him with a serious expression. "What else could we do?"

"We ease humanity into the fact that the supernatural exist. The process has already started in a sense with Sacred Gear holders all being human to some degree. We should start with small areas and expand outwards, kinda like gossip at school. It starts out as a secret between a few close people, then they tell other people they are close with and so on until everyone knows but they all try their best not to make a big deal out of it. Eventually once they all realize that everyone knows they would hopefully have known about it long enough for it not to be a huge deal."

"Would it really run that smoothly?"

"Probably not, but you all also have people whom you have forged contracts with who can vouch for you on your behalf, not to mention the people whom you've become friends with without ever telling them you were a devil." Issei gave her a small smile. "Worst case scenario we erase their memories with magic, but the bottom line is to erase the anxiety between humans and supernatural beings."

Rias gave Issei a tired look. He was saying something irresponsible again about such a serious topic, but it was clear he had put some thought into it. Da Vinci also mentioned something about him making reckless promises before but that he always seemed to make it work. Maybe I will believe in his way of thinking as well. Rias thought to herself with a small smile.

Issei noticed that Rias was staring at him and decided to change the subject. "Ah, sorry about that. I guess we should leave that kind of talk for another time when it becomes relevant. How do you think you're fairing in your training?"

"I think my power and accuracy is improving. Watching Space Ishtar, which is a strange name by the way, was very informative in both using concentrated power to eliminate an enemy and using spread attacks to eliminate groups of enemies as well, although I'm not at the level of being able to both spread my attack out while keeping the power the same as a single powerful attack."

"I see, it's good to learn from the heroic spirits. Honestly if we had more time I would have gotten them to train you all personally, but since we're on a tight schedule we'll have to save that for after the match."

"After the match?" Rias asked, surprised.

"Of course. We are comrades after all, and there will no doubt be struggles you will have to experience without me so this is the best I can do to help." Issei said with a smile.

Rias returned the smile but couldn't help the feeling of anxiety of having to fight a battle without Issei's help. She had come to rely on him for support in the past month and had now found that she was attached to him. Clearly he didn't feel the same or at least didn't think she felt that way. "Hey, maybe you could teach me some things." She said shyly.

Issei gave her a surprised look, not expecting that suggestion. "I'm not against it but there are others who are better suited to teaching you than me. Maybe I should ask the Queen Witch to teach you." He mused.

"Ah, I met her at the celebration dinner. We had a nice chat." Rias said happily.

"Oh really? How did that go?"

"She was really supportive of my plight and offered to help teach me some magic."

"I see. She is very powerful but has a mischievous streak in her. Medea Lily who is working with us is one of her disciples so if you want an idea of what her training is like you should talk to her."

"I see. Maybe I will go talk to her after." Rias had a curious look on her face. "By the way, why do people call her the Queen Witch or the Witch of Okeanos?"

Issei made a complicated face. "That is a more complicated question than it might appear." To Rias' confused look Issei continued. "I'm sure you noticed that some of the servants around here are called by their title rather than their name."

"You mean like the Berserker of El Dorado and the Assassin of the Nightless City?"

"Yeah. When they were summoned that's how they introduced themselves so that was how we called them, but as time went on some events happened that revealed their true names to me."

Rias looked at him confused. "True names? What do you mean?"

"Rias, do you know what the fourth wall is?" Issei seemed to ask out of nowhere.

Rias was becoming more confused but answered. "Isn't that something related to when t.v. shows and other forms of media speak directly to the person or people viewing it?"

"That's right. This world has a complicated relationship with the fourth wall." Rias was completely lost so Issei continued. "Haven't you noticed that the way our training facility works is similar to that of a game?"

Rias thought about it and came to the only conclusion that made sense to her. "This world is a game!?"

"Well, that has yet to be determined. These mechanics and logical inconsistencies are more or less contained to Chaldea. The rest of the world is no different from ours. It might be because we have so many powerful magical beings that can influence reality around them, but the bottom line is that strange things that happen don't make sense unless you look at it from the lens of it being a game."

"What kind of inconsistencies?"

"I know what the Queen Witch's name is." Rias had a surprised look on her face. "Her name is Circe and she was the witch from the Odyssey. There was an event that I investigated before I came back that had us explore the island that was Circe's home when she was alive. One thing led to another and the Singularity was resolved. In the process Circe was able to find closure with Odysseus and I learned the details of her story during our investigation."

"I see. She said that you might know her identity but by the sound of it she should know that you know."

"Right, that's where the inconsistencies come in. After the event was resolved the servants acted like nothing happened. Circe talks to Odysseus like they resolved their issues whenever they see each other but any other time it's like the events of the Singularity never happened."

"She clearly remembers it happening cause when we were talking she gave me an abridged version of that story you just told me."

"Normally I would have brushed it off as a quirk of hers but the same thing happened with Berserker."

"Her too?"

"Yeah, her name is Penthesilea. She is the Queen of the Amazons. A different event happened before Circe's where her true name was revealed to me as well. I'm sure you get where I'm going with this." Rias nodded so Issei continued. "After everything was said and done everyone acted like it didn't happen. My best explanation is that these Singularities are like events in an online game where things happen for a limited time but don't affect the main story, that being what we are doing here in Chaldea, and as such the information is blocked until it is no longer necessary to block it. I have lovingly called this phenomenon convenient amnesia as a joke."

Rias laughed at Issei's naming of the phenomena but was having a hard time trying to understand it. "So what does this have to do with the fourth wall thing you mentioned?"

"Well between the convenient amnesia and the game-like mechanics used to empower servants it seems like someone would notice it or bring mention to it at some point. But whenever someone does bring it up it gets brushed aside or the conversation progresses so quickly that we are suddenly on a different topic. So we don't break the fourth wall like a show, it's more like we lean heavily on it and do our best not to break through it."

"That's incredibly strange."

"Agreed but you get used to it after a while. It's best just to go along with it otherwise you will never be able to sleep at night just trying to figure it all out. Besides, we don't know what could be on the other side of that wall." Issei said tiredly with a hand on his head. Rias just nodded in agreement and the pair continued walking together to rejoin the others training.

(2 Days till the match.)

It was the day before the ORC returned home and the group was preparing for the match against Scàthach's team. The members of the ORC had gotten significantly stronger after their training but were still nervous about fighting famous heroes. Meanwhile the servants didn't seemed bothered at all and saw this as a good time to spar. Issei was especially looking forward to showing off some more of his skills to his servants.

As the group was walking to the training area they eventually made it and saw Scàthach standing out front waiting for them. "So, you are finally here. Are you ready to see the fruits of your training?"

The ORC had nervous looks on their faces but nodded their heads. Issei smiled fearlessly at his teacher. "We'll show you what we can do shishou."

Scàthach gave them a sly smile. "All right then. Follow me." She said and walked into the room. The ORC steeled themselves and walked into an unknown hell.

After the practice match the ORC were all laying on the ground, exhausted and sore from their match with Scàthach's team. The servants on their team were roughed up but no worse for wear, and Issei who exerted himself the most in a one on one with Scàthach was a bloody mess just like when they sparred the first day. Asia was currently healing him along with Medea Lily. Mash was crouching over him with a tired look on her face. "You really need to stop pushing yourself like this Senpai."

Issei gave her a tired smile. "Sorry Mashu, but I won't improve against shishou without getting this reckless. The better I get the less beat up I will be in the future."

"Maybe so, but don't overwork yourself to the point where you accidentally cripple yourself."

"Yeah that would be bad." He said sardonically. Mash gave a small laugh and ran her fingers through his hair soothingly.

The others were starting to pick themselves up off the ground when Scàthach walked up to them. "I will say that you all didn't do too bad. I can tell you've been in some fights but you're all still a little green to real combat. Although if I have learned anything from my time with Master is that the modern world is a different age for warriors. You all definitely started off better than Master did when I started training him."

"Hey! I'm still here you know!" Issei complained.

"And? It's the truth." Scàthach said matter of factly. Issei just pouted while Mash and Asia tried to comfort him. "Anyways, your skills are passable for now. I don't think you should have trouble with the upcoming match, but if you want more than this you will need to train even harder. Power aside I can tell that you all have something that is holding you back. While I won't pry I suggest you all find a way to overcome whatever it is." When she said that Akeno, Koneko, and Kiba looked away with slightly complicated looks.

Issei noticed and wanted to ask but thought that he should save it for after the match. I should tackle one problem at a time.

"Well that's all I have to say for now regarding your progress. You should spend the rest of your day recovering then what time you have tomorrow putting the finishing touches on your training." Scàthach suggested.

Everyone nodded then left to rest. As they were walking out Issei saw that Rias seemed to be lost in thought. He was going to say something but was stopped by Mash. "Senpai, let me talk to her." Issei gave her a confused look. "This is something that should be handled between girls." She said with a smile. Issei was lost as to what she was talking about but trusted Mash's judgment so he left it to her.

It was late at night and Issei was preparing for bed, but he was taking his time because something strange was going on. The past nights since they all came here the girls had been sleeping with him but tonight no one was here. He could only absently wonder what was going on. Rias and the girls did have a rough time training today. Maybe they need time to themselves to think about what shishou said? He thought to himself. As he was lost in thought his door opened and Rias walked in. Issei looked at her with a mix of curiosity and relief. "Oh, there you are. I was beginning to think you weren't going to show up."

Rias smiled at him but there was something else behind it that Issei noticed. "Yeah sorry. After the match I had some thinking to do and the girls helped me clear my head."

"Well that's a relief to hear. I know shishou can be hard on people at times but she means well."

Rias nodded then seemed to go into thought again before speaking. "Hey Issei?"

"Yeah?"

She slowly walked up to him and pushed him onto the bed. Issei was taken by surprise not expecting this from her. She got on top of him and looked him in the eyes. "What do you think of me?"

Issei was confused, not sure what she meant. "I think you're a naive, rich girl with a little too much pride." She slightly scowled at him for that. "You are someone who not only cares about her family but those around them. You're honest and hard working and a bit of a flirt, but most of all you're compassionate. I believe your heart is in the right place and that once you figure out what you want in life you will be a frightening force." Issei said, not sure if he was supposed to be supportive or romantic so he did a mix of both. "Not to mention you're hot as hell. Pun fully intended." He said with a smile.

Rias had a wry smile and happy tears from the praise she got from Issei and it only confirmed what she was already feeling. She wanted to be with Issei, not just because he was strong or clever, but because he was honest with her. He always told her the truth even back when he didn't completely trust them. He didn't treat her with kid gloves or with needless platitudes like the devil nobles did. Finally, he was risking his own freedom just so she could have hers. Rias decided to follow Circe's advice from the dinner and to get what she wanted no matter what. "Hey Issei?"

"Yes Rias?" Issei said, slightly nervous about whether or not he said the right thing.

"The others aren't coming here tonight, so why don't we do it?" She said seductively into his ear.

Issei's brain slightly fried from her words. "R-Rias we talked about this already didn't we?" He said, trying to recompose himself.

"Yes we did, but this time is different."

"How so?"

"I was unsure about what our relationship would be after we beat Riser and it had been bothering me for a while. But after our time together as a couple and the time we spent training here I've come to realize that you were the person I've been waiting for."

Issei looked at Rias seriously. "Isn't that a bit over dramatic a conclusion to come to?"

"I don't mean you specifically, I'm talking about someone who is willing to look at me as Rias. Someone who is not only there to support me but is willing to challenge me so that I can become better. You have constantly been pushing me and what I've known and it has gone to show me I have much more to learn to be not only a good king but a good head of my family in the future."

"You don't need to be in a relationship with me to get that. I will continue to support you as long as you don't betray my trust." Rias had a bit of a sad look on her face. Issei couldn't take such a face so he compromised. "How about this? Once we win the match against Riser, come talk to me again. If you are really serious about this then I will accept it. I'm sure this might seem like I'm being insensitive but I want to be sure this is you talking and not the pressure of the situation."

Rias stared at him for a bit, unsure what to do. This didn't progress as she had hoped but she could understand his hesitancy to believe her. Between Raynare and Fluorous his ability to trust others and their intentions had been compromised. She realized that this was something she was going to have to help him work through along with Mash. He won't be truly happy if he's second guessing everyone's intentions when they try to get close to him. "Very well. Once we win, I will not only ask you out-" She leaned in till their faces were a hair apart. "I'll make sure you can't live without me." She said seductively.

Issei's brain once again fried from the words of the red head. Is this what they call the devil's temptation? I'm not sure if I mind all too much. Issei thought to himself.

"Since the others aren't coming tonight we have the room to ourselves so why don't we get ready and head to bed." Rias said with a smile. Issei dumbly nodded and they both turned in for the night.

(1 Day till the match.)

The ORC spent the rest of their time at Chaldea training and before the end of the day they were all getting ready to head back. As they were heading towards the teleportation room along with the participating servants they were met in front of the door by Da Vinci and the three Neros. "Come to see us off?" Issei asked.

Da Vinci smiled at them. "I am, but as for these three…"

Nero puffed out her chest with pride. "Umu! We are going with you." The other two Neros nodded their heads in agreement.

Issei had a slightly exasperated face. "I'm fine with that. Just don't cause any trouble when we get there please." The three Neros nodded again in acceptance.

"Just to remind you, I will be monitoring you during the match so that we can gather more data. Also we finished the modification on your clothes and have imbued them with Mystic Codes so you will have some protection when you're out and about." Said Da Vinci.

"Thanks Da Vinci. I'll make sure to get used to the new features when everything is over."

Da Vinci nodded and looked towards everyone with a smile. "I wish you all luck in the upcoming match. Once you win we will make sure to hold another celebration dinner." Everyone nodded and gave her a brave smile as they left for Kuoh.

When the group came back Issei's parents greeted them and the Neros introduced themselves. "Greetings Hahaue-dono and Chichiue-dono, we are Nero Claudius, Praetor's wives. Umu!"

When they introduced themselves like that, Issei's parents nearly fell over at their son bringing back three more women who claimed to be his wives. The pair looked to their son and Issei just gave them an exasperated look while shrugging. They looked back to the trio standing proudly and finally spoke to them. "W-well then, welcome to our home." Said Issei's mom, still digesting the information. "We were just about to make dinner for everyone since we know you all have a big day tomorrow."

Everyone showed a big smile at that and all got ready to eat dinner. While that was happening the other servants who weren't there before introduced themselves to the Hyoudou parents. Emiya went to the kitchen to help cook dinner and the others got accustomed to the house. Issei's mom loved Bunyan and couldn't help but hug her which caused her to blush profusely. As the house was becoming lively Rias went next to Issei and leaned on his shoulder. "We will definitely come out on top tomorrow." She said with confidence.

"Yeah, let's make sure to do our best." Issei said while showing a bright smile.

Welcome to Chaldea Gremory group! This part was what I was most interested in and I still didn't even put everything I wanted in it. This whole trip could be a side story onto itself so that's what I'll do eventually. So firstly: even though the servants will be in the fight if they actually fought there would be no conflict and would leave a bitter taste in Rias and her peerages mouth. So that's why I had them come up with the plan that they did. Second: as I'm sure FGO players know, while the main story is serious everything else that happens is a free for all in terms of self awareness and what can happen so I'm gonna play into that a bit. Third: in the original story Issei was traumatized by Raynare which prevented him from seeing that the girls were interested in him. That still happened here but to a lesser degree because he already had a good connection with Mash and the other servants. Combine that with Professor Lev's treachery and it's a cocktail of mistrust. It's why he seems dense to Rias and other people. Finally: I used this chapter to be something of an eye opener for Rias. As I'm sure you notice between the two volumes, the supernatural beings of this world seem to be used to things going a certain way and thinking it's just natural. Well in my version of this story Issei is basically gonna make everyone question if things are the way their suppose to be. All right that's it for my thoughts on this chapter, hope you all enjoyed. And to the guy who wrote a dissertation on Rias in the comments, I like your points and partially agree but as far as to whether or not I succeed at that will be up to the readers. Also Rias didn't do any specific training as far what was mentioned in the light novel, but that seemed to be because she was focused on training Issei and Asia who were both new and the weakest members of the team. 10 days isn't exactly a lot of time to train newbies to be good in battle so her time was spent on them. On top of that she wasn't lazy about it, she took an active role in their training.