The next month was spent with business going on as normal. Rias and Issei spent the month going out between work and school. Rias also got closer to Mash and in turn she began to open up to the other members of the ORC. Asia was getting used to being a devil and doing her job as one. Issei and Mash offered to accompany Asia on her jobs to make sure things were fine and she was handling it properly. In the meantime, Chaldea was close to finishing the transportation circle for regular use as the deadline was approaching.

Rias and Issei had become close during their time together and it came to the point where those who knew that they were fake dating wouldn't be able to tell if that was true or not. Their closeness was noticed by the students at the school as well and rumors were going around that Issei was cheating on Mash while blackmailing one of the schools Great Onee-samas. No one asked directly though and Issei told Kiryuu about the situation during one of their free times at school.

It was the afternoon in the ORC as everyone was relaxing before their jobs came up. Rias was at her desk looking through some papers as Akeno was preparing tea for everyone. Issei and Mash were talking and sitting across from Asia who was relaxing in her seat and Koneko who was eating sweets. Kiba was sitting in another chair in the room reading a book. Everything was calm until a magic circle appeared in the room with the crest of Gremory in it. From it appeared a voluptuous silver haired maid.

"Grayfia? What are you doing here?" Asked Rias.

"I am here to be an intermediary for the agreement between yours and Lord Riser's marriage. He will be here soon." Said the now named Grayfia.

"I refuse to marry him Grayfia!" Rias protested.

"We will discuss this when he arrives." The maid said.

Rias huffed and slightly slouched in her chair. She looked over to Issei who met her gaze. A moment passed and she relaxed herself, preparing for the plan. Some time passed until finally a new magic circle appeared in the room with a different crest in it. Flames erupt from it and out of that appears a blonde short haired man in a burgundy blazer with gold embroidery on the right with matching pants and black shoes. He looked around the room with contempt until his gaze reached Rias.

"You've caused me a lot of trouble making me come here just to get you Rias. You should stop messing around in the human world and return to the Underworld where you belong." Riser said authoritatively.

"You can't tell me what to do Riser, and you don't get to decide what I do with my life!" Rias shot back while rising from her seat to stand opposite of him.

"You are my fiancé and you will do as I tell you!"

"I told you I refuse to marry you!"

"That's enough! Both of you calm yourselves!" Said Grayfia from the side of the room.

The pair begrudgingly became silent. Riser moved behind the desk and took Rias' seat as if it was his right. Rias glared at him but then turned to Issei. Issei was glaring at Riser but stopped to meet Rias' gaze. He showed her a reassuring smile and patted the spot next to him imploring her to sit next to him. Rias smiled gratefully but then it turned mischievous as she walked over to Issei and instead of sitting next to him sat on his lap wrapping an arm around him. Issei was surprised but did his best not to let it show. Grayfia was observing him discerningly trying to figure out what the boy's connection was to Rias. Riser on the other hand became enraged.

"Who the hell are you and why are you touching my fiancé!?"

"Me? I'm Issei Hyoudou, Rias' boyfriend." Issei said casually.

The room froze for a moment as both Riser and Grayfia were digesting the information. Not long after Riser started to laugh rather hard.

"You? Rias' boyfriend? That's the funniest joke Riser has heard in a long time." Riser said, full of contempt.

He talks in third person? What a weirdo. Issei thought to himself. "I knew he was gonna be self important but it's even worse in person." He said to Rias on his lap.

Rias giggled a little at Issei's comment. Riser on the other hand was not amused. "Who do you think you are human? Trash like you shouldn't even be in the same room as us devils. In fact, why are you even here?"

"I'm here because I am a part of the club and as I stated earlier Rias' boyfriend. We have been spending quite some time getting to know each other better. It's been, stimulating, to say the least." Issei said coolly.

Both Riser and Grayfia's expression visibly changed. Grayfia began to stare a hole into Issei while Riser was becoming more agitated. "Rias!? Don't tell me you actually slept with this trash!" Riser was practically screaming.

"So what if I did? I will sleep with whoever I want to." Rias said snarkily.

Riser was looking at her in disbelief while Grayfia continued to stare at Issei and Rias. Issei decided to speak up again. "It's funny that you think that just because there is some agreement that you suddenly have control over Rias. Even if you do get married, which you won't, what makes you think she wouldn't just cheat on you? You all seem to act like she's some kind of mindless drone who would just quietly do as she's told."

Riser was now glaring at Issei, flames beginning to form on his body. "You worthless human trash! Who do you think you are!?"

"You need me to introduce myself again? Geez you're not only pompous but apparently you're slow in the head too." Issei remarked, earning some laughs from the other members of the ORC. "Although, I guess I did leave out something important." Issei lifted his left arm and the Boosted Gear appeared. "I am this generation's Sekiryuutei."

With the appearance of his Gear Grayfia's presence became less aggressive and was now observing Issei calculatingly. Riser on the other hand was now wary of him. "Hmph, so you're not just a human. But it doesn't matter. Devil affairs don't apply to you so you should stay out of it."

"Awww, what's the matter? Suddenly scared to deal with me now that you know you're talking to one of the Heavenly Dragons?" Issei mocked.

Riser showed a smug look. "Why would I be scared of an overgrown reptile. It is a fact that phoenixes are superior to dragons in every way."

[The hell did he just say!?] Ddraig spoke in Issei's mind.

"Calm yourself Ddraig. We'll make him eat those words, count on it." Issei said to Ddraig mentally. "In what universe is an oversized chicken better than a dragon? Did your mom drop you as a kid or something?"

Riser did not take kindly to that and flames once again began to form on his body. "You brat! I will teach you not to look down on the great Riser!"

"That's enough!" Said Grayfia. Riser looked at Grayfia somewhat defiantly but after a look from Grayfia he stopped. Grayfia looked over to Rias. "Rias-sama, if you don't want to marry Riser then you will have to oppose it in a Rating Game."

Riser now looked smug after Grayfia said that. "If it will make her stop resisting then I'm fine with that. It's not like she stands a chance against me. She doesn't even have a full peerage, unlike me." Riser boasted about his chances and then turned to an open space in the room. He created a magic circle and from it a group of women appeared. Girls of various looks, heights, and clearly personalities. If Issei's friends were here they would be weeping at what they would consider a perfect harem. "Not only do we outnumber her, my servants would no doubt beat them into the ground."

The ORC scowled at him for that so Issei took that as his que to jump in. "Well if you're so confident about yours and your peerage's abilities then why don't you let me and my servants fill in for Rias' empty spots?"

Riser looked at Issei somewhat skeptical but still condescending. "And what would be in it for Riser?"

"Simple. If you win, not only would you get Rias' hand in marriage but you would get my loyalty as well. Naturally that would include the loyalty of those who follow me. I'm sure getting one of the Heavenly Dragons as well as all that serve me as your subordinates would earn you some prestige among devil society." Issei said coolly.

Rias and the others looked at Issei in shock, not expecting him to make such a huge gamble. Riser showed a confident smile, greed evident on his face. "Very well I accept your terms. I will give you ten days to prepare for the match, not that it's going to help you."

"In that case I will inform the families and arrange the match. I will provide information for both groups tomorrow morning." Grayfia said stoically. With a last smug grin Riser walked to his peerage and disappeared with them. Grayfia was preparing to leave as well but stopped to address Issei. "Sekiryuutei. Why are you involving yourself in this matter?" Grayfia probed.

Issei looked at the maid doing his best to avoid looking at her large breasts and answered her seriously. "Because Rias deserves the right to choose who to be with for herself. I also find it ironic that a group who pride themselves on strong family bonds is trading away their family member like some kind of trinket." Issei said, displeasure eminent in his voice.

Grayfia showed a small smile but quickly returned to her stoic look. "I see." Is all she said before she left.

The ORC were now looking at Issei with worry. The one who spoke first was Rias. "Issei are you crazy!? Why would you risk your own freedom for this!?"

Issei looked at Rias and gave her a bright smile. "Because you are worth it." Rias blushed heavily at that. "Besides, I told you that if you got my servants in you wouldn't lose and I meant that." Rias looked skeptical still but trusted Issei. Issei turned to an open space. "Da Vinci-chan, how is the transportation circle?"

A hologram appeared where Issei was looking and Da Vinci appeared. "It should be ready by tomorrow. I've informed the servants and we're preparing for your arrival so no worries on that end."

"Good. Once we get the information for the match we'll head to Chaldea to begin our training." Issei said confidently.

"I will arrange our absence from school so we won't have to worry about that." Said Rias. Everyone nodded in agreement and left the club early to prepare for the next ten days of training.

(Gremory Territory)

"Hahahahahahaha! Who would have thought the person that got my daughter's attention was the Sekiryuutei!" Rias' father was laughing rather hard after being told about the meeting and the arrangement that was agreed upon.

Rias' mother on the other hand had a complicated expression. "While I do admit it's a bit surprising that someone so notorious has joined her side, I don't know whether or not I should be happy that there is a chance the arrangement could fall through."

Sirzechs was standing beside Grayfia with a smile on his face. "I'm sure things will work out for the best mother, no matter the result." He turned to the maid. "Did the Sekiryuutei say anything else?"

Grayfia made a complicated look before returning to her stoic look and answering. "I asked him why he was involving himself when he had no stake in this."

The three were now focusing on Grayfia, curious about the answer. "And? What did he say?" Asked Mr. Gremory.

"He said that Rias-sama has the right to choose for herself who she wants to be with." The trio made a small smile at the answer but Grayfia wasn't done. "He also said that he found it ironic that the family that prides itself on strong family bonds is trading their daughter like some trinket. Also that Rias-sama is not a mindless drone who would just quietly do as Riser said. He suggested she would cheat on him because of how much she dislikes him."

The Gremory parents froze when they heard that. They weren't expecting to be slandered like that, nor did they think of Rias possibly retaliating in such a way that may cause a different set of problems down the line. Sirzechs made a small chuckle. "Looks like the Sekiryuutei has a poor opinion of us at the moment. We may want to move with caution when we meet him. After all, he was willing to bet his own freedom to make sure Rias has hers, so that shows how seriously he is taking this." The Gremory couple went into silent contemplation while Sirzechs looked pleased at the turn of events.

All right, it's time. next chapter is the training arc and the longest chapter in this volume. I wonder if anyone can guess who is gonna be on the team from Chaldea. I'm sure some choices might surprise you. Granted my choices are slightly biased because I chose mostly based off who I have in my FGO profile but I did do some research for the battle plan I used so stay tuned.