Rias was standing by the window of her clubroom, lost in thought. She was anticipating her encounter with Issei and going over how she was going to approach him. She had no doubt that he would agree to go out with her, but then what would happen? Should she let him take the lead? Should she take the lead? How will she explain the supernatural to him? Should she even say anything? She sighed. She knew that she had to tell him somehow, it was only a matter of time since he had the Boosted Gear. Not to mention that since this was the past, Grayfia would try to stop her from getting too close to Issei while her engagement was still on. That was another complication she was going to have to deal with. Her and the other's powers were reset back to how they were in the past, so they all had a lot of training to do. Thankfully, a lot of their previous issues were due to personal mental blocks, such as Koneko's senjutsu and Akeno's holy powers from her fallen angel side. But thanks to Issei they no longer had any qualms about that. Thinking about that made Rias all the more eager to recruit Issei again. As she was lost in thought she heard the sound of people talking outside her clubhouse. She looked down and saw the people she was waiting for. It was Issei and his two friends, Matsuda and Motohama. He seemed to be complaining to them about the two of them abandoning him at the Kendo Club's Dojo. A smile made its way to Rias' face, feeling a bit nostalgic for the old Issei who used to be shy and peep constantly. As she was reminiscing, she made eye contact with Issei who happened to look up. He seemed to get lost in her eyes while she looked at his with affection. The other two noticed Issei's gaze and saw Rias in the window as well. They seemed awed by her too, although not to the same degree as Issei was. She then decided to make her way down before he decided to leave. She quickly made her way to the entrance and saw the three about to go back. "Hold on a moment," she called out, getting all three of their attention.

The three were stunned that one of the Two Great Onee-sama's was talking to them. "I-Is there something wrong, Gremory-senpai?" asked Issei, in a slightly anxious tone.

Rias mentally frowned at Issei being so formal with her but knew it wasn't his fault. They were strangers after all. "You're Hyoudou Issei, correct?" Issei seemed stunned that Rias knew who he was and mechanically nodded. Rias had to hold back a laugh as she continued. "No need to be so nervous. I just want to talk." It took a few moments for Issei to calm down as his friends watched the exchange in awe. "I know this might be sudden, but I was wondering–" she spoke while fiddling with her hair, slightly nervous. "If you have a girlfriend?" she asked.

This question stunned the trio. Matsuda and Motohama had their jaws hanging open at what was happening in front of them, while Issei, through some miracle, managed to keep his jaw closed but was staring at Rias in disbelief. He actually reached up and pinched himself, which caused Rias to laugh slightly. "This…, this isn't a dream, right?"

Rias gave an affectionate smile to him. "No, this isn't a dream. I'm really asking you out."

"... Why?" was all Issei could get out. While he was incredibly happy inside, his brain just couldn't keep up with what was going on.

Rias looked away, slightly embarrassed, but also a bit unsure how to phrase it. She couldn't exactly tell him they were lovers in the future, although a part of her believed he would believe that if she actually said it. "I've had my eye on you for a long time. Despite the rumors, I thought I would see what kind of person you are for myself."

"And after everything you've seen, you still want to go out with me?" he asked incredulously.

Rias walked up to him and placed a comforting hand on his cheek. "Issei, there is more to you than just your taste in women. I believe you're a kind man who could see someone for who they truly are, and will protect the people close to you. Sure, you have some bad habits, but those can easily be resolved, once you have me, right?"

Blood began to escape Issei's nose at what Rias was implying. Was she really offering herself to him? Offering her body, her love? The girl of his dreams was asking him out, and he couldn't be happier. But there was something he had to be sure of. "Uhm, Gremory-senpai."

"Rias," she corrected. "Call me Rias."

Issei felt his face go a bit flush. "Rias-senpai, if you've been looking into me, then you should know about my dream, right?" he asked, with great hesitancy and nervousness.

Rias' smile never left her face. "You want to be Harem King, right?" Issei's face showed slight shock at how nonchalantly she said it. "While definitely a "ambitious" desire, it's not like other boys don't have those kinds of fantasies. You're just brave enough to say it out loud." She gave him a comforting look. "If you're worried about if I mind, well it would be a lie if I said I wasn't the jealous type, but as long as I'm your number one, I don't mind you having other girls."

This was like a dream come true for Issei. Not only was the girl of his dreams interested in him, but she was even ok with being part of a harem. "His" harem. It took everything in him not to jump up and down in excitement. Although her words about being the jealous type did worry him a bit, but he would just have to make sure he took care of her and it shouldn't be a problem. "Are…, are you sure you want to go out with me?" he asked, making sure this wasn't some elaborate joke.

There was a hint of pity in Rias' eyes, as she saw some insecurity in Issei's eyes. He hadn't experienced the tragedy from Raynare yet, but clearly his insecurity had always been there. Raynare had only amplified it. This only made her more determined to make sure that tragedy doesn't repeat itself. "Yes, I do. This isn't a joke, or some prank. I truly wish to be with you, if you'll have me," she said, her tone sounding humble at the end.

Issei's heart couldn't resist that and nodded vigorously. "Yes! Of course! I would love to be your boyfriend! Thank you for having me!" Issei said excitedly. His enthusiasm made Rias smile.

Meanwhile, Matsuda and Motohama had tears coming out of their eyes. A mix of jealousy, envy, and surprisingly happiness for their friend. "Issei, you damn traitor! We were supposed to get girlfriends together!" said Motohama.

"Not only that, but you bagged Rias Gremory, one of the Two Great Onee-samas of the school! And she supports you having a harem! You lucky bastard!" complained Matsuda.

Issei was too caught up in his own happiness to care about his friends' complaints. Rias looked at the two and gave a wry smile. "I would ask that you two keep this a secret. While I'm not ashamed to be dating Issei, I'm at least aware enough to know that if the rest of the school finds out they will make things difficult for Issei-kun."

At those words, Issei's expression went from joy to worry. She was right, if the rest of the school finds out he was a dead man. He could already see the other students chasing him around the school, accusing him of all sorts of things he hadn't done. He began to become downcast at this. "Aww man…. The best thing to ever happen to me and I have to keep it secret," complained Issei.

Rias patted his shoulder. "Don't worry Issei. Worst case scenario, I will clarify things myself." Issei gave her a grateful look. "Now then, why don't you come inside? I want to introduce you to the rest of the members of the ORC."

"Introduce me?" asked Issei, confused.

"Yes. You're not a part of any clubs, right? So, you will be joining the Occult Research Club starting today," said Rias nonchalantly.

The perverted trio were surprised. It was notoriously hard to get into the ORC and here Issei was being brought in so easily. "You want me as part of the club?"

Rias gave Issei a small pout, which he found cute. "Of course. Don't you want to spend more time with me?" Issei nodded his head vigorously. Rias smiled at that and hooked her arm around his, pressing her breast into it and causing his nose to bleed again. "Then this will give you the perfect excuse. Also, the others are also interested in meeting you."

"Hmm? Others? Wait, you mean…!"

Rias smiled. "Yes. Akeno, Kiba, and Koneko are all looking forward to meeting you. There's also a transfer student who joined recently and he's also interested in meeting you," she said while leading him away.

The other two members of the perverted trio were now cursing Issei more at his amazing stroke of luck. "Issei, you bastard! You better tell us everything later!" said Matsuda.

"If you don't, we'll definitely beat the crap out of you later!" said Motohama, as the pair waved him off. Issei had all sorts of complicated feelings at how fast things were moving, but he wasn't complaining.

Issei was led into the clubroom and as he entered, he saw people standing around the room. Issei recognized most of them immediately. There was Akeno, the other of the Two Great Onee-samas, standing by Rias' desk. Koneko, a kouhai who is considered the school mascot, was sitting on a sofa eating snacks. And Kiba, the school prince, who was standing near a window, reading a book. Issei immediately felt annoyed at seeing Kiba, having been jealous of him for how popular he was with the ladies. He finally turned his gaze to the fourth person in the room. She looked like a cute girl who had an air of innocence around her and was currently sitting in a box on a chair. Issei felt infatuated for a moment before he looked confused. Didn't Rias say there was another boy? Why was this cute girl here? Rias snapped him out of his thoughts by addressing him. "Welcome to the Occult Research Club."

The club members looked at Issei and all showed kind expressions. Issei was a bit taken aback that it seemed everyone was so welcoming. "H-hello everyone," greeted Issei, a bit nervously.

Akeno walked up to him almost immediately. "No need to be nervous Issei-kun. We're a welcoming group," she said while pressing her body against his arm, causing him to make a slightly stupid face.

This earned an amused chuckle from Akeno, who always enjoyed Issei's more perverted side. Rias pouted in jealousy while Koneko looked slightly displeased. Kiba was just giving his usual cool smile while Gasper was smiling at Issei. Rias cleared her throat to get Issei's and Akeno's attention. "Akeno, while I appreciate your, "enthusiasm", for welcoming Issei, we should take things one step at a time," she said, trying to be as diplomatic as possible.

Akeno saw right through Rias and smiled mischievously. "You just want to hog Issei to yourself for as long as you can, right Rias?"

Hearing this made Issei confused. Hogging him? Was that an indirect confession from Akeno, or was there something else going on? Issei wasn't able to understand. Seeing the confusion on Issei's face Kiba decided to step in. "Rias-buchou, Akeno-fukobuchou, please stop confusing Issei-kun. He's completely lost."

The pair looked at Issei and realized that they were getting ahead of themselves. "Right. Sorry Issei-kun. I like to tease, but only with the cute ones," said Akeno playfully.

Rias sighed at Akeno but recollected herself. "Sorry about that, Issei. I'm sure you're familiar with everyone but let me properly introduce them. This is Himejima Akeno, my Vice-President, Yuuto Kiba, Toujou Koneko, and our transfer student Gasper Vladi."

Issei looked at Gasper then back at Rias. "I thought you said the transfer student was a boy. Why is there a cute girl here?" asked Issei.

The others gave knowing looks as they all showed amused smiles. Gasper spoke up. "I-I am a boy. I just like wearing girls' clothing because they're cuter and more comfortable," he said a bit sheepishly.

Issei took a second to process the information before he finally reacted. "Ehhhhhhhhh?!" His reaction was just like how it was before and the other couldn't help but laugh. "Why does he look like a girl?! A really cute one too?!"

Gasper made an embarrassed expression. "I-I just like the clothes. I still want to be a man!" he said with determination.

Issei felt a strange sense of seniority when he looked at Gasper and when he said he wanted to be a man he felt like he should help him. "Well, when you say it like that, I can tell you're serious about it. Yosh! I'll help you out. I'll teach you the ropes of how to be a man."

Gasper looked happy at that. "Yes! I'll be counting on you, Issei-senpai!" He was relieved that he could still keep his senpai-kouhai relationship.

The others were happy that Issei was already forming a bond with their group. "Glad to see you're already getting along with the others. Now then, we can go over the details of the club another time. I just wanted to get you acclimated to your new after school environment. What do you think?"

"I think this is cool. I mean, this club is basically the haven of the most popular people in school. What guy in their right mind wouldn't want to be in a club with a bunch of pretty girls? Gasper seems cool too, even with the crossdressing. And Kiba's here too I guess," said Issei, seeming a bit annoyed that Kiba was here.

Kiba felt a bit hurt by that. He forgot that Issei used to be jealous of him, and the only reason they got along was because they were part of the same peerage. But he wouldn't let that deter him. He owed Issei a lot and he knew that Issei would come around if he showed him his sincerity. "There's no reason to be so cold Issei-kun. I promise to help you with anything you need. All you need to do is ask," said Kiba with a cool smile. Issei made a complicated face. Part of him felt he was being sincere, but his jealousy was also getting the better of him.

Rias decided to try and change the subject. "So Issei, what do you want to do now that we're dating?"

Issei was caught off-guard, not expecting to be put on the spot like this. He thought for a moment and then seemed to nod to himself. "Well, it's only natural that we go on a date, right?" Rias smiled at this. She was looking forward to this. "How does this Saturday sound?"

"I would love to. How does 10am sound?"

Issei nodded happily. "Sounds good. I'll meet you downtown. I promise to make this the best date you've ever had," Issei said enthusiastically.

Everyone smiled at that as they always enjoyed how Issei looked at Rias. Rias did her best to contain her excitement. "Then I'll see you then. That will be all for today. I will see you tomorrow at 10, alright?" Issei nodded and he left. There was a moment of silence when they all heard Issei yell in happiness for his situation in the distance. This caused all of them to chuckle and share warm smiles. "So? I think that went well."

"I forgot how cute he was when he wasn't used to being around us all the time. While I enjoy his loving gaze, his more innocent yet passionate gaze when he looks at me is very stimulating," said Akeno.

"I still have mixed feelings about his perverted actions. But unlike before, I'm more jealous of his gaze going to others," said Koneko.

"I was a bit disheartened that Issei-kun doesn't like me. I forgot he used to be jealous of my popularity. But we can rebuild our friendship. I hope he will be open to being comrades," said Kiba.

"Don't worry Kiba. I'm sure you can earn points with Issei by giving him "advice" about how to get to know us better," suggested Rias. Kiba nodded with a smile.

"I'm glad Issei-senpai wants to mentor me on being a man again. I feel safer when I can rely on Issei-senpai," said Gasper.

"Seems like things have gone well. Now all that's left is…."

"Raynare…," said Akeno with venom in her voice.

"We need to keep an eye on Issei-kun while we track her down," said Kiba.

"We know where they're based, but if we act too soon we may end up preventing Asia from showing up. For now, we wait until Asia gets here. In the meantime, Rossweisse should join us in a few days," said Rias.

"So for now, we wait," said Akeno. "I don't like it, but I know we can't be too rash."

"Don't worry. We won't fail this time." Everyone nodded as they made preparations for their future battles.

Here is this months voted for chapter. Rias is now taking the first step to try and change Issei's fate, but will it really work out that way? This one was short, but that's because I wanted to save next chapter to keep certain events together. I did debate putting the date here but decided against it. As for the other characters, it's going to be interesting writing how they have to navigate recreating a relationship with someone who doesn't remember having one. I think that writing Issei and Kiba will be a bit challenging. But I'll try to find a balance. Side note, unrelated to this story, a Youtube channel called DxD Fiction has started posting my stories on their channel read out by A.I. so if you want to hear my stories instead of read them I would recommend going to his channel and listening to it there. As always, I look forward to the comments as always. : )