Some time passed and the engagement was dissolved. Issei, Mash, Rias, and her peerage all had a celebratory dinner when they got back and a week later everyone returned to Chaldea to celebrate their success in the mission as well. Everyone was currently in the Chaldea cafeteria eating and talking to the servants and staff. Issei was currently talking to Da Vinci.

"We got a lot of useful data out of your various battles during the game. We also confirmed something quite interesting." Said Da Vinci.

"And what would that be?"

"When you used your Mystic Codes during the battle they were much more potent than normal. I had a hunch about this before, but this confirms that the mana in your world is not only still present like in the Age of Gods, it is vastly more potent. The reason for this is still unknown and we won't be able to figure it out until we establish a base in your world."

"Right well my meeting with the Maoh went better than expected so I will continue to work on that." Issei said while looking around the cafeteria. He spotted Rias talking to Circe and absently wondered what they were talking about. As per the agreement once everything was settled they stopped going out. Issei expected this but still felt a little sad that it was over. But he knew that Rias wouldn't actually be in love with him and that she was just acting under pressure. But he was fine with it, since he did what he said he was going to do.

As he was having these thoughts Rias walked up to him and Da vinci. "Hey Issei, can we talk for a bit?"

"Sure Rias-buchou."

Rias frowned for a moment before putting on a happy expression again. Da Vinci gave Issei a look like she was looking at someone who couldn't be helped but Issei didn't notice. The pair left the cafeteria and went into the hallway. Once there was no one around, Rias spoke. "Do you know why I wanted to talk to you?" Issei shook his head in denial. "It's to ask you out silly."

Issei couldn't comprehend what she said for a moment but then his brain finally caught up. "Wait, seriously?"

Rias pouted slightly. "Of course I'm serious! Don't you remember what I said on our last night we spent here?"

"W-well yeah but I thought you were-"

Rias put on a serious look and brought her face closer to his. "I told you that I seriously wanted to be with you. There is no longer an engagement hanging over my head and no one to pressure me into anything. You have been there for me when I needed you most and you treat me like myself." She paused and took a deep breath. "I love you Issei. Will you go out with me?"

"..." Issei couldn't really deny it now. She did everything she said she was going to do as well as everything he asked of her. He said half that stuff just to be supportive and relieve her stress, but she took it all seriously. In the end it seemed that he was the one not being considerate of her feelings. Issei let out a wry smile. "If you're ok with someone like me then I will gladly accept you."

Rias showed the brightest smile Issei had seen on her and she embraced him in a tight hug. "Thank you, Issei." Issei hugged her back. After a moment Rias moved her head and kissed Issei on the lips. They held that for a few moments before Rias separated herself from Issei with a smile. "That was my first kiss." She said with a blush.

Issei showed a look of surprise but smiled. "I'm honored to be your first."

As the two were in their own world Mash, Asia, Akeno, and Circe were all around the corner spying on them. They were all happy at the development and were trying not to spoil the moment. Maybe now Senpai will be able to open up more to everyone. Mash thought to herself.

(Underworld, Gremory Territory)

"I told you things would work out for the best." Said Sirzechs.

"Is this really the best outcome?" Asked his mother skeptically.

"I believe so. Lord Phenex has long since wanted Riser to lose so that he could gain some humility and was hoping that Rias would do so. So even if the engagement was broken off we did him a favor."

"True but we lost many other deals since the engagement fell through."

"No offense mother, but that's your own fault since the other deals were made by you and not part of the original agreement. In that respect I agree with Issei-kun that you shouldn't have put that pressure on Rias."

Mrs. Gremory pouted slightly but couldn't complain. She knew she dug her own hole in this case. She never usually made a bad deal so her failure this time seemed to bring her to reality a bit. "... Do you think Rias is mad at me?"

Sirzechs and his father both looked at her with a kind smile. "Rias is a smart girl. Even if she didn't like the arrangement, I'm sure she knew where you were coming from dear." Said Mr. Gremory.

"Right, she didn't display any displeasure after the battle. That all came from Issei-kun. But that's to be expected when someone tries to take your woman away." Said Sirzechs playfully.

The Gremory parents smiled but Venelana slightly frowned. "The Devil Council isn't going to like that the Sekiryuutei, a human, is getting close to a devil noble."

Sirzechs kept his smile as he replied. "There's no need to worry. After all, we, along with Lord Phenex, only told everyone that Rias was aided by the Sekiryuutei, not that they were in a relationship. As long as they keep a low profile, they will be fine to do as they wish. Besides, wouldn't it be a great benefit to us to have the Sekiryuutei as a member of the family? Surely you can see the benefit in that mother." Venelana went into silent contemplation thinking about what Sirzechs said. Sirzechs then turned to his father. "That aside, me and the other Maoh are working to change the rules of the Underworld in order to have a more prosperous future, so having Issei-kun help push that along would help change things for the better."

Everyone nodded in agreement and started preparations for what the future could bring.

Finally, we have come to the end of volume 2. This has been an interesting experience and having people read and talk about my work for the first time has been a new experience. This doesn't mean I'm done however, next is volume 3 but before that I'm gonna take a break cause I've been putting off doing other things to write these last two volumes. So since we're at the end for now I want to know what everyone thinks of my first two volumes? It may be a while before I upload again but the next time I do I will probably be done or close to done with volume 3. And just to give a hint of what's coming next we have the holy sword arc, featuring the treacherous knight of Camelot, the Saints, and the alter duo of Shinjuku. Until then, stay tuned. ; ) P.S. I knew I was gonna forget to put this in but here is a little behind the scenes thinking for me as I was writing the fight. When I originally planned for Issei and Riser to fight I was gonna have Issei do a pseudo-Noble Phantasm by combining the skills he got from Scàthach with the techniques from Emiya. Basically I was gonna have him do Scàthach's Gae Bolg Alternative by projecting the weapons and using Gandr in unison. Of course his version would be weaker than the real one but he would boost the power of it with his sacred gear. This didn't end up happening because as I was writing I forgot about it but when I remembered after it seemed to be out of place so I didn't put it in. Anyways that was just a glimpse into my thought process as a bonus.