Disclaimer: First Chapter
Story Start!

Asia looked serious.

"Issei... can I talk to you about something... bad?" Asia could pick a better time and place, because currently Rias was in the clubroom, but she was busying herself by looking at crystal balls. She did raise an eyebrow, though she felt she had some form of clue as to why Asia wanted to speak with Issei.

This was interesting.

"Sure, you know you can talk to me about whatever!" Issei seemed more than happy to listen. He had noticed that there was a change in Asia lately, but he just assumed it was the fact her new life was finally catching up to her. There was a massive culture shock, not that he had much more experience as a devil than her.

'I bet she feels bad, because she has feelings for you, but now has feelings for another guy.' Rias thought to herself.

It was kind of Issei's fault, since with other guys he made sure Asia was never alone with them. At school she spent time with girls, or with Issei and some of his friends, but Issei never allowed her to spend time with other guys alone for fear they would take advantage of her. It was somewhat wholesome in a way, but at the same time it was a great way for her to not develop any feelings for a guy that was better than Issei in some way.

'If Asia never truly interacts with a man who shines brighter than Issei, he remains her bright light... but that happened, and Issei himself encouraged it. Her light, showed her a brighter light... somebody more kind, more fun than him... somebody who, like Issei, saved her in some form.' Rias analyzed how she felt Asia felt, which would be very confusing for the girl with budding romantic feelings. To have the object of her affection push her towards another man, and to gain budding feelings for that man as well.

Rias stopped what she was doing and watched.

This was VERY interesting.

"... I don't know how to feel... about Naruto... and you." Asia didn't know how to put it gently.

Issei nodded.

"I completely understand, I love that tomboy vibe she has... total cutie... I completely understand if she makes you feel things... and you should totally explore those feelings... and maybe ask her if she wants to hang out with me too." Issei didn't hear what Asia had whispered near the end. Lesbian action was hot to him, and he would LOVE if Asia helped him unknowingly spread his harem for him. If she could get another girl interested in him, and that could turn into the cornerstone for his harem.

Rias took a deep breath, and put her hands together.

'Holy crap... this is leading to NTR right in front of me. Issei knows Asia has budding feelings for him... and because of his own misunderstanding, his high defenses are down.' Rias had never seen a man unknowingly push his potential lover away in such a strange way, or at all. Issei was VERY guarded when Asia was with other men at school, so he had a very high guard when she was with men, but in this situation, his guard was down.

In his eyes, he was just trying to expand his own harem. Rias looked at Asia, who seemed to be surprised by the fact Issei was supportive of her feelings.

Rias said nothing.

The fact was, she didn't have a right to say anything anyway. She wasn't involved in whatever was happening, and nobody asked her for advice. What was more, Asia had genuine feelings she wanted to explore. Rias looked at the two men from an objective standpoint, and she knew that Asia was being pushed towards the higher quality man by the lower quality man.

The Man who lacked a harem, but wanted it more than anything.
The Man who was growing a harem, but reluctantly accepted it.

'... Hopefully this will be a good lesson to Issei, and he bounces back stronger... who knows, maybe this will be better for Asia too... either way, I have no right to involve myself in this love situation.' Rias kept her lips shut, not even letting out so much as a giggle at how the situation was playing out.

"I should?" Asia asked.

"You should, you TOTALLY should... you want Naruto to hold you, then do it. You want to kiss, then DO it... and you should send me pictures when you do. Go on a date or two. Perfect, lets go ask right now!" Issei was SUPER excited, and it showed in every part of his body language. "Buchou, where is Naruto right now?"

"Training... Naruto enjoys training by the forest, at the foot of the mountain to the Southern edge of Kuoh." Rias knew exactly where Naruto could be found. "... though... be careful you don't get hurt." Rias told Issei, and that was her only warning about what he was going to be doing.

Koneko entered the room with Yuuto as the newest members were leaving.

"See you later Koneko-chan, I'm going to help Asia get a date with Naruto... this is going to be so hot."

They left the room.

"... He's a cuck?" Koneko asked Yuuto, confusion clear on her face as she watched another man seemingly love the idea and push for the girl who loved him, to develop feelings for another man. "He's a cuck?" Koneko repeated to Rias, when Yuuto just shrugged his shoulders.

"He's thinks Naruto is a girl, and is pushing for Asia to date him... he's trying to expand his harem. This will be a good lesson for him, so don't say anything. He's letting his lust control him too much... this lesson is important." Rias stated rather simply. Issei had made assumptions all on his own, and was pushing for something he had no right to push for. He was also being manipulative, which was a great trait for a devil... but Issei was thinking with his lower head and not the smarter one.

Akeno entered the room.

She also seemed confused.

"Did you guys know Issei was a cuck?" Akeno asked the room, since she just passed an excited Issei and confused Asia down the hall.

"Don't you have a fetish for affairs?"

"Yeah... I just didn't know Issei was into cuckold play. If I had known, I would have helped him out. A shame, really."

"Issei still thinks Naruto is a girl, and is trying to add Naruto to his harem by using Asia's growing feelings for him... he doesn't know that he is pushing her into another man's arms." Rias explained the situation to Akeno, who blinked a few times. Akeno sat down and contemplated if she should get involved.

"Okay then."

She decided this was just a lesson her junior needed if he wanted to control his lust, because he would NEVER learn to control himself until pushed into a position where he lost something important. Losing Asia due to his own greed and lust would make him want to work harder, and maybe become a man who wouldn't do it again.

"So we're all just letting this happen?"

"We don't have the right to interfere at this point... Issei is making a mistake out of lust... but for Asia, she is genuinely confused. This is a good chance for her to figure her feelings out. By helping Issei, we are denying Asia... and by helping Asia, we are against Issei... lets just let them figure this out on their own." Rias answered Yuuto, since he was the only guy in the room. He was the one who seemed to feel bad for Issei, but not bad enough to really put up much of an issue. "... Yuuto, I need you to train with Koneko... actually, Akeno you train with Koneko. Riser's Queen likes to defeat Rooks with surprise attacks. Koneko needs to work on dodging surprise attacks, Yuuto... I want you to watch Riser's knights with me." Rias had bigger fish to fry at the moment anyway.

"What about Naruto?"

-With Naruto-

"You want me to what?"

"Please, I'm begging you... go on a date with Asia! She has been developing feelings for you, and she is very conflicted about them!" Issei was on his hands and knees, begging Naruto for Asia to consider the date. "I know it will be awkward... but please show her a good time. I already got a date with Asia... and she should go on a date with you too, so she can understand her feelings." Issei looked up.

Naruto stared at Asia.

"... I've... got feelings for... the two of you, and he wants me to try this." Asia was shyly looking away from Naruto and Issei.

Naruto looked at Issei once more, only this time with even more confusion.

"Wait... so you know this girl likes you, and now she likes me too... and instead of trying to make yourself look better, you are pushing her to explore her feelings?" Naruto was SO confused right now about what was going on. Issei seemed like Asia, and Asia did seem genuinely conflicted about her feelings. Still, none of what was happening was adding up to him at all.

He was getting more confused.

"Are you okay... in the head?" Gasper asked Issei from the shadows.

"Oh yeah... I think this is a great idea."

"Ah... lust." Naruto now fully understand what was going on. Issei was thinking with his penis and not his brain, and that was pushing him into making some horrible choices. Asia got more conflicted by the way Issei was talking. "... you are fully okay with this Issei, you are perfectly fine with the chance that Asia falls for me even more?" Naruto wanted more confirmation.

Issei gave him a thumbs up.

"Sounds hot!"

"Ah... and Asia, are YOU okay with this?"

"... I want to make Issei happy, and he wants this... and I have feelings for you too... and I'm just so confused." Asia answered back, since she didn't know her feelings. She went to Issei because she wanted him to comfort her, and maybe take her on another date. She never expected that he would be so okay, and would so lustfully push for something like this. "... can you please help me?" Asia asked Naruto, she looked down at him and he could see that she was close to tears.

She really was super conflicted, and nobody was helping her figure her feelings out.

He rubbed her forehead.

"Okay then... I'll help you figure this out. How about we go on a date... Friday?" Naruto asked her, offering her the date.

"I would love to."

"YOSH! Another one for the harem! The harem grows by one more member!" Issei couldn't help himself but celebrate.

'Yeah... but not your harem... it seems like the more Naruto doesn't want this harem he is growing, the more it grows... I just want to see him wear cute clothes, and date cute girls. I'm not going to say anything.' Gasper was going to help Naruto get with Asia if he could, and not just Asia, but any girl that had feelings for Naruto. He was going to do what he could from the shadows for his partner, because it was very fun for him to watch.

"Well, I'm going to get back to training... so if you will excuse me." Naruto brought his wings out.

He then wrapped then with shadows around the base, before he covered the surface of his wings with a lighter layer of wispy shadow. Naruto flew off with a burst of speed that flipped Asia's skirt into the air, and left Issei looking at her butt.

...

"Okay, we have until Friday to get you ready. We need to pick out a good outfit for you... all you have are school uniforms and nun clothes. Oh... you should ask Buchou to help you, I've got no fashion sense at all... and she can help you pick our your lucky panties too!"

-With Rias-

"... you're telling me that entire terrorist story... it actually happened... what the hell?" Rias read a letter from her brother confirming what had happened during the contract, had actually happened. She never called them liars, but for some reasons she had a hard to just accepting it as a real in her heart.

Great, now she needed to reward him for his bet AND for stopping a terrorist plot.

Chapter End!
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