As the next day went by after Y/n met Kurumi Tokisaki and Riser yesterday, he was going through out the day and kept it civil between him and Kurumi in Kuoh Academy, while at the room Y/n was talking about the training ground where Rias is going at and she told him that she's going to training house with enough space to for her and his Peerage.

Y/n: So, what about your pawn who has Ddraig?

Rias: You mean Issei? He do have to get stronger if we're going to win against Riser.

Then he thought of an idea he had.

Y/n: I know just a person for that, Rias. She's in Hanzo academy and training with Asuka and her teammates with a old friend of mine.

Rias: And who's that?

Y/n: Don't worry, Rias. You'll be surprised.

He checked the clock and noticed that he has to go back to his house and tell his peerage about the place Rias and her peerage is going at but Y/n have to tell something about Rias and maybe he'll confess to her.

(Timeskip)

At the training house location, Y/n and his Peerage was waiting for Rias and the others to arrive and he turn to his peers that they're training them about offense and defense while Y/n will be training Rias about using her Power of destruction to manifest into weapons but Tatsumi asked him a question.

Tatsumi: What about Issei's training? Also, which one of us going to train him?

Y/n: Simple, Tatsumi. I called a old friend of mine to bring her in. And let me tell you, she's a brute for a woman.

Yumi: You're talking about her, right?

He nodded and Wendy was curious about her then Kazuma looks at Y/n and said.

Kazuma: Who's she talking about?

Y/n: You'll find out soon.

After several minutes, Wendy sees Rias and the others was coming in but Tatsumi was surprised that Koneko has a giant backpack. At the entrance, Rias and Y/n is discussing about which one of his peerage is training Rias's peerage and he said Esdeath should train Kiba on sword and reading the opponents move, Wendy should train with Koneko about fighting, Yorktown and Kuroka should train Asia about healing with her sacred gear of her friends far away, Katerea should train Akeno about her lightning abilities and teach her about the Frostia's ice magic, and Y/n told Issei something.

Y/n: And lastly, Issei. I would send Tatsumi, Raynare, Mittelt, Kalawarner, or Kazuma to train you but I brought a special guest.

Issei: And who would that be?

Y/n: Let's say that she's right behind you.

Issei turn behind him and saw a woman who literally looks like a female Jojo character, Daidouji.

Issei: Holy shit!

Then Yumi recognized her and said to Y/n.

Yumi: You called Daidouji?!

Y/n: Of course, Yumi. If Issei is going to get stronger to fight Riser's peerage, it's her.

Daidouji looks at Issei while he was shaking in fear and said to him.

Daidouji: So, that's the red dragon emperor? But more of a wimp.

Issei: Hey!

Y/n: Anyways, everyone. Let's get to training!

Then everyone in his Peerage is training Rias's peerage and as for Issei, he has to do pushups while two big rocks while Daidouji is in front of him and Y/n was teaching rias to manifest her powers into weapons of choice. So after training was done, everyone was getting ready for dinner and Issei was in pain due to extreme level of exercise but he tells Asia that he's gotten stronger.

As for Y/n, he was at the balcony while it was nighttime before dinner has started. He looks at the sky and was still worried about Kurumi was in his school but he reminded himself that he has his and Rias's peerage to calm him down when he breakdown in sadness or suffers from PTSD, Rias came in because she was checking in on her friend.

Rias: Aren't you coming in the table?

Y/n: Yeah. I just.....need some time alone.

Rias: It's about that Kurumi Tokisaki person, isn't it?

He nodded and she reassuring him while telling him that he shouldn't let fear control him as she hugged him while patting his head, Y/n smiled at her and he have to say the truth.

Y/n: Rias.

Rias: Yes?

Y/n: There's something I need to tell you.

Rias: What is it?

He took a deep breath and exhale, then he said.

Y/n: When I met you a few years ago while me, you and Sona was playing in my family's castle, we used to have a sleepover and you and Sona help me out with my issues, including my nightmares. You're always been there for me and the same as Sona. Now, years later, you've grown into a mature woman but still have the same compassionate self as usual.

Rias: What are you talking about?

Y/n: (Here goes nothing!) What I'm trying to say is, Rias! Is that..... I love you! I love you as more than a childhood friend!! Can you be my girlfriend, Rias Gremory!?

When he finally confess his feelings to Rias as she was shocked while blushing towards his confession and she smiled at him and said.

Rias: I have the same feeling as you, Y/n.

She cupped his cheek and both of them started to kiss with such compassion for a minute or two till they separate and looked at each other but someone came in.

???: Well, isn't that cute?

Rias turned around to see a small girl with black hair, elf like ear, and black eyes.

Rias: Who're you?

Y/n: Ophis?!

Rias: You know her?

Y/n: Long story, Rias. Ophis, what're you doing here?

Ophis: Thought I came to see you. Heard that Kurumi finally found you and challenged Riser to the rating games.

Y/n: I mean, I already know that's Riser gonna lose because my peerage just trained Rias's peerage but we have to do this for ten days then we'll be ready.

Ophis: Sounds fun. Also, do you want me to bring your second Peerage after the fight with Riser?

Y/n: You've already found them?

Ophis nodded and Rias was confused about what she means but Y/n told her that he can have a second Peerage.

Ophis: Anyways, may I join you and the rest of you for dinner tonight?

Y/n: Sure, Ophis.

So, they walked back to the kitchen table and everyone was eating their own dinner but after dinner was done, Y/n was changing into his night shirt as he got on his bed and fell asleep but continued to train them for ten days as he was thinking about defeating Riser.

(Hope you guys enjoyed it! Make sure you like and give me ideas for his second peerage and tell me their names and their abilities in the comments below!)