Issei and Rias headed downtown to find a place to eat. As they walked Rias wrapped her arm around Issei's, purposefully pressing her breasts against him. Issei blushed heavily at her actions but tried his best to keep his face straight. When they got to the center of town they looked around to see if there was anywhere they wanted to go. As they were looking around they were called out.

"Ara ara. If it isn't Issei-kun and Rias." Said Akeno, walking up behind them.

"Ah! Hello Akeno-san. How are you?" Issei greeted politely.

Akeno smiled gently at Issei. "I'm fine. Just doing some shopping. Are you two out on a date? Ufufufu, you sure work fast Issei-kun." She said teasingly.

"Akeno, do you have any recommendations for lunch? Me and Issei-kun can't seem to decide what to eat." Asked Rias.

Akeno put a finger on her chin in thought. "Well, there was a good casual dining restaurant not too far from here with a pretty good menu and decent pricing. I'm quite a fan of their meat products. They cook it really well." She suggested.

Issei smiled brightly at Akeno. "That sounds great! Thanks Akeno-san."

Akeno showed a mischievous smile then moved in close to Issei's face. "No problem Issei-kun. Maybe when you're done with your date with Rias you could take me out as well." She said seductively.

Rias pulled Issei closer to her and gave Akeno a small glare. "Well anyways, let's go Issei. We should go before it gets too late. Thanks for the suggestion Akeno. I will see you Monday." She said as she started pulling Issei away.

Issei with a nervous smile followed along. "See you later Akeno-san."

As the pair walked off Akeno was watching them leave while making a mischievous face. This may be more fun than I thought. Issei-kun is kinda cute, not to mention he is so fun to tease. He might be perfect affair material. As those thoughts circulated through her mind she continued on her way home.

As the two were heading to the restaurant Issei saw that Rias was pouting slightly. "What's wrong Rias-senpai?"

"You're supposed to be spending time with me, not flirting with Akeno." She said with a pout.

"I wasn't flirting, I was just talking with her. Although I wasn't expecting her to tease me with a date." He said airily.

Rias looked at Issei thinking he was being coy, but after staring at him a bit she noticed that he really didn't have a clue. Could it be that he is actually dense when it comes to romance? "Hey Issei? How do you and Mash usually spend time together?"

Issei looked confused at the sudden change of topic. "Well, we usually spend time socializing with the servants or people at the house. When we go out I take her to places that she finds interesting. She never got to leave Chaldea unless it was for a mission so this is all new to her."

Rias seemed to have a look of realization. I see. So he doesn't have any experience with a normal girl. Which means he doesn't know how to read signs when girls drop them. Mash is also new to not just relationships but general society, so Issei has never had to deal with girls dropping "hints" to him.

"Is something wrong Rias-senpai?" Issei started to look a little concerned.

Rias came out of her stupor. "No. Nothing is wrong. Also, it's Rias."

"Huh?"

"Since we're going out you must call me Rias. If you're too formal then the plan won't work." She said somewhat sternly.

"Ah, right. Sorry Rias." Issei said as he just realized his mistake.

Rias smiled. "It's fine, let's go have lunch Issei."

Issei seemed confused at Rias' rapid change in emotions but went along with her. The pair went to the restaurant and had a good lunch. Then they went shopping together. They stopped at a clothing store and currently Issei was waiting awkwardly outside the changing room in the women's section. He was doing his best to ignore the stares from the other women in the building as he waited for Rias. Eventually Rias came out of the changing room in a red dress that matched her hair.

"What do you think?" She said as she twirled around to give Issei a complete view.

Issei stared at her for a bit, slightly stunned by how good she looked in the outfit. "You… You look amazing. I always figured you would look good in anything but that outfit is just, wow."

Rias blushed heavily at the compliment but smiled. "Thank you Issei. I guess I know what I'm buying here." She said happily.

After some more shopping, Issei and Rias were walking around town and eventually ended up at the park. They sat at a bench to relax a bit and enjoy the scenery. After a bit of rest Rias decided to ask Issei something that has been on her mind.

"Hey Issei. Why are you really helping me? Considering what I was trying to do to get you as my servant, even if it wasn't for bad reasons, it was still unacceptable of me to do that." She said somewhat ashamedly.

Issei looked in front of him in contemplation before answering. "Well, you're not the first person to try and use me for their own ends. Honestly I'm used to it. I guess I feel more strongly about it because this place is my home and I don't want something or someone to taint it." Issei leaned forward in his seat and turned his head to Rias. "I guess it was because I also believe you should have a choice just like you think. Many of my servants have lived lives where they could never truly get what mattered most to them and they took that desire to their graves. I never want to feel like that, nor would I ever want someone else to feel that way either. When we spoke before and you said you wanted to be seen as Rias I understood that I was actively going against my own morals because of what happened to me in the past, something that technically had nothing to do with you. Then I thought, what did I see in you before I disappeared and how did my return change that?"

Rias leaned in now curious. "And? What did you see in me?"

Issei slightly blushed. "Well, I'm not sure how closely you were paying attention to me before I disappeared but I had a massive crush on you. You were my perfect woman."

Rias knew this but also noticed Issei's phrasing. "Were?" She asked somewhat hesitantly.

"I've been through a lot and have experienced and seen many things and well, my perspective has changed on a lot of things. If I never got amnesia I don't think I ever would have changed from the pervert I was."

"How did you become so obsessed with breasts anyways?"

Issei had a slightly embarrassed look on his face. "Back when I was in grade school my childhood friend moved away. I didn't have friends anymore so I would often play by myself. One day in the park I was playing alone when an old man started talking to me. He noticed I was sad and decided to comfort me with stories." Rias didn't see how this was related but held her questions for now. "When he told me his stories they were about breasts in varying degrees. I found them very enjoyable and for the next week I would come back to the park to hear more of these stories."

Rias had a look of disbelief on her face. That's why he was so obsessed! Some dirty old man poisoned his mind at such a young age!

"After that week the man had to leave since he said he was visiting the town so I didn't see him anymore after that. But the stories he told me got me out of a bad place when I was young and stuck with me. Eventually I made friends with Matsuda and Motohama who were like me and in the end we just sort of accentuated each other's bad habits." Rias nodded in understanding agreeing with Issei's assessment.

"So, am I not your dream girl anymore?" Rias asked, getting back to the previous topic.

Issei observed Rias for a moment then answered her. "I don't know. If I were to think back on how I felt about you then compared to now, I would say I feel the same. To me you felt like some unreachable woman that I could never hope to be near. Even though someone like Akeno, who has a body that I should technically find sexier than yours, based on my preferences, was around there was something different about you that I just found myself drawn to." Issei threaded his hand through his hair. "Then we talked and you were no different from a normal girl, devil heritage notwithstanding. I began to understand you better and saw that you had troubles of your own. And I just wanted to help you. I realized I needed to give you the benefit of the doubt just like I gave many others before. Then maybe I would be able to get to know the real Rias." Rias felt her heart skip a beat for a moment when he said that. She could tell he was being serious. "Even now that we're going out I can tell that you can't really be yourself because the agreement is hanging over your head so I want to help lift that weight from your shoulders. Then once everything is over, I look forward to getting to know the rest of you, even if we aren't going out anymore."

"You don't want to stay a couple?" She asked somewhat sadly.

"In all honesty my two personalities are at war with each other. My old self wants to do what I've always done, which is "appreciate the female body" if you catch my meaning. The other part of me wants to be more prudent of how I act and has been more focused on Mashu and the others whom I've risked my life with." Issei sighed. "When I went to talk to Mashu about the plan she was afraid that I was replacing her with you, which I would never do. She has known about my dream ever since I got my memory back because I told her and Da Vinci everything about myself once I remembered. She said that she wouldn't hold me back from it but I can tell it's bothering her. When I told her I would stop she panicked and told me that I shouldn't give up my dream for her since I'm helping her achieve all her dreams. So I'm stuck in a complicated position of trying to keep her happy while pursuing my dream."

Rias could understand that. If someone came in and tried to talk to her man she would be intensely jealous too. She then began to understand why Mash was so distant from her and the others. "I see. Well this was a problem that would pop up eventually if you planned on having a harem."

Issei smiled self mockingly. "Yeah I guess so. To answer your question, I would love to keep going out but you're going to have to tell me if you want that, otherwise I will consider everything settled once your engagement is broken off."

"You're going to make me ask?" She pouted slightly.

"Yes. I've just bared my heart to you without holding back, so the least you could do is show that you feel the same, when the time comes anyways." He said teasingly. He didn't really expect anything to come of it, he was just messing with her.

Rias blushed slightly but nodded. "Well let's see how this relationship goes and maybe I will." She teased back. They then both got up leaving the serious stuff behind for now and went home.

It was the middle of the night as Rias was quietly making her way to Issei's room. After their date they came home and had dinner with everyone. Afterwards Mash had pulled Issei aside to talk about something out of hearing distance from everyone and when everyone went to turn in for the night the pair had gone to bed last. Rias wondered what it could have been but decided to think about it in the morning. She had a hard time sleeping in her new home and thought that since she was going out with Issei that sleeping in the same bed wouldn't be a problem. She thought that Issei would probably enjoy it and think it was a nice surprise. As she got to his door she opened it quietly so as to not wake Issei. When she got in his room she was surprised to see Mash sleeping next to Issei. She never took her for the type to do something bold like that but since they were going out it wasn't too surprising. But what was the most surprising was that the pair were naked together, not only that there was a faint erotic smell in the room. She had heard the rumors in school about Issei not being a virgin anymore but she thought that it was overexaggerated gossip after talking to Mash and seeing her reserved personality. Clearly she was wrong. She stood there in awkward silence before recomposing herself. Even though Mash was here it didn't change what she was going to do, so she undressed until she was also naked and slipped into bed on Issei's free side and cuddled up to him. As she got closer she noticed the scars on Issei's chest and torso. She remembered when he returned his parents requested that he be able to wear a shirt during activities that required he be without one like swimming. Now she could see why. Japanese culture doesn't look fondly on people with scars even if they were acquired for good reasons. She was brought out of her thoughts by Issei stirring. Issei unconsciously wrapped his arm around her which made Rias smile and she fell asleep in his embrace.

Issei began to stir from his sleep. He felt more comfortable than usual as he felt something soft in his right hand. He clenched his hand slightly to try and feel what it was.

"Ah!"

A cute moan came from the side of him. His groggy mind thought it was Mash but as he started to wake up he noticed that was not the case. He felt Mash on his other side and knew her proportions didn't match what he was feeling. He became more awake and saw that Rias had snuck into his bed, stark naked and nuzzling against him. Her body was pressed tightly against his with her breasts pressed against his body and one of his legs intertwined with hers. He then noticed that the soft sensation he was feeling was her breast in his hand. Part of him wanted to enjoy the sensation a bit longer but decided against it. He slowly released his hand from Rias' breast so as not to wake her but as he was moving his hand away it was suddenly grabbed.

"Why did you stop?" Asked Rias in a quiet tone, a bit of mischief in her eyes.

"Why are you in my bed naked!?" Issei asked quietly.

"I had trouble sleeping so I came to sleep with you. Imagine my surprise when I saw you and Mash together, after what I could only assume was an "eventful" night for the both of you. As for why I am naked, I always sleep naked. It's more comfortable for me that way."

Issei blushed at being found out about his and Mash's late night activities. "Well you should go before Mashu-"

"Before Mashu what, Senpai?" Said a voice from Issei's other side.

Issei felt his blood freeze, slowly turning to face Mash who was smiling. Her eyes on the other hand were not. "Ah, hey Mashu. Good morning." He said with a strained smile.

"Good morning Senpai. Rias." Her expression didn't change but she was clearly not happy.

Rias smiled happily at Mash. "Good morning Mash-san. How was your night with Issei?" She teased.

Mash's expression finally changed as she couldn't keep her upset atmosphere up while being embarrassed. "W-why are you here Rias-san?"

"I wanted to sleep with my boyfriend, same as you. It isn't fair that you get to and I don't." She said.

Mash showed a conflicted expression. "But you two are just acting, there is no need to go this far is there?"

Rias gave Mash a kind look. "Well, maybe not but this is how I want to get close to Issei. I'm also doing this to help you."

"Help me?" Mash was lost.

"Yes. When Issei and I went out on our date we were talking and naturally the relationship between you two came up. I understand you have conflicting feelings about Issei's dream, but if you want him to fulfill it then you need to get used to other women being close to and around him."

Mash looked down slightly ashamed. "I…"

"Listen Mash, I don't want to take Issei away from you. I just want to be close to him just like you are. I understand that you are new to this but every relationship will have its difficulties, even ones as unique as this." Rias reached her hand across Issei and gently touched Mash's cheek. "If you really love Issei then you need to have faith that he will stay beside you."

Mash was quiet for a bit, but finally found her words. "I'm sorry Rias-san, Senpai. I was being selfish."

Issei pulled Mash in closer. "No, it's fine Mash. This is just a learning process for everyone. I need to learn to handle this better so as not to make you and others sad."

Rias smiled at the pair but moved in not wanting to be left out. "Then we can all learn to handle this together. Maybe I should ask Asia to join us as well."

"There is no reason to add her in if she doesn't want to Rias." Issei said airily.

Both Mash and Rias stared at him. He gave a confused look to the both of them saying "What?" while they were thinking the same thing. He is really oblivious to the feelings of other girls isn't he? They both seemed to understand that unless the girl outright said they were interested in him he was oblivious to it.

Looks like I'm going to have to teach him the subtleties of women as well. Thought Rias.

So I'm not gonna lie, even I felt like this chapter was a bit rushed when I wrote it but I wasn't sure how to make it more fleshed out. Since Issei wasn't just following along like in the original story I had a hard time coming up with things to do. It turned into another therapy session near the end of the date. I'm gonna try to work on that in the future but it's simply a case of when I sit down to write my mind goes blank sometimes. On a different note while I know I could of left Asia out of Rias' peerage, she gets a lot of development because she is in the peerage and has to improve for others. While she could just do that for Issei it wouldn't really hold the same weight. Besides, I have a plan for her later in the story that will involve certain servants giving her a hand, if you catch my meaning, so don't be sad that she still ended up with Rias. There is a plan. ; ) P.S. I also slightly altered the backstory of Issei's perversion origin because the original one was silly but not really meaningful in my opinion.