A/N: chapter summary at the bottom.

"Are you sure this is a good idea?" Asia asked. She fidgeted.

The deep cut black dress and heels made her feel uncomfortable. But Issei told her to wear it, so she did not complain.

"Why not?" he asked.

"It's the middle of the night."

"We're short on time. We'll need all the time we can get to link our strategies."

"With whom? This is the Underworld, but what devil would help you?"

"One who hates me," Issei said cryptically.

"That makes no sense."

"Trust me. Now come on. We're wasting time."

"These heels aren't easy to walk in," she said.

"You wanted to come with me."

"Yeah, but…"

"Want me to carry you?"

"I'm fine."

"I wasn't asking."

He swooped her up into his arms. Asia yelped. Then, she settled into his powerful arms.

"Thanks," she mumbled.

"No prob. Now, enough time wasted."

Issei spread his dragon wings and flew towards the castle.

"Now remember what you promised," he told her. "I'm taking the lead. And you obey whatever orders I give you."

"Always," she said.

They landed in the courtyard. A couple guards spotted them. In seconds, they were surrounded.

"Who are you?" one of them demanded.

"I have a secret meeting with him," Issei said calmly.

"I know of no secret meeting," the guard said.

"That's why it's a secret."

"Yeah, right. You-"

Issei summoned his Sacred Gear. "You know what this is?"

"I don't give a-"

"Mitch," another guard butt in. "That's the Boosted Gear."

The guard frowned. "You're Issei?"

"You know anyone else with a Boosted Gear?"

"I'm sorry. We did not recognise you."

"It's okay," Issei said. "You were just doing your job. Now can you take me to him?"

"Of course."

They followed the guard into the castle.

After a couple corridors and stairs, they reached their destination. A large set of double doors. Behind it, they heard sounds. Girls squealing.

"Maybe this is not a great time," the guard said.

Issei ignored him and pushed open the doors.

"Riser?"

The high class devil was standing naked at the edge of his large bed. In front of him were two cat-girls in doggystyle-position. Ni and Li. He was fucking the blue haired one, which Issei believed was Li, but he could be wrong.

When he saw Issei, he yelped in surprise. The devil jumped back, lost his balance and fell hard on his ass.

"Riser-sama?" one of the twins said.

The girls helped him up. Riser rubbed his sore butt. Then, he turned to Issei.

"Ise? What the hell, dude?"

"Sorry, but it's really urgent."

Riser sighed. "Fine. Let me get dressed first."

"Sure."

Issei went outside again.

"I'm confused," Asia said. "That's Riser."

"Yes."

"But… you fought him before. Doesn't he hate you?"

"After the fight he was in a depression," Issei explained. "So Rias and I went down here to help him out. Akeno came along too."

"But not me?"

"Well we didn't want to bring a whole crowd. He was pretty deep. Scared of everything. Especially dragons. He never lost a fight before, so it hit him pretty hard."

"And you pulled him out?"

"Sort off. It went well at first. But then Rias and Akeno went to the hot springs to take a bath. He wanted to see them, and I obviously couldn't allow that. So I beat him again."

"That sounds bad."

"No, it was good. The fight was… different. The stakes were less high. I mean, sure, Rias and Akeno's naked bodies were in peril, but not an engagement or anything. When he fought me he really got into it. I won in the end, but he accepted his defeat. He accepted that sometimes you win and sometimes you lose. We shook hands."

"I see."

"After that we became… well… 'friends' is a big word, but he called occasionally to talk about girls. Troubles of a harem. Jealousy, arguments, feelings for his sister, you know. The usual stuff."

"Ise, I… I'm sure that was all interesting and fun, but… asking him to fight for us is completely different from calling him once in a while to talk about girls."

"I know. He won't fight for us. At least, not for free."

"What could you possibly offer him?"

"Good thing I brought you along."

"A-Are you suggesting-"

"I'm saying that you promised to obey any order I give you. You promised that you would be mine when we escaped."

"Yes, but-"

The door opened. Riser was dressed now.

"Okay," Riser said. "Come on in."

Ise went in. Asia followed him reluctantly.

Was he planning to offer her body in exchange for his help? That was just… crazy.

She should have just stayed home. This was clearly punishment for forcing him to take her along.

Or maybe he just realised he had no choice? What else could he possibly offer Riser?

With him and his fifteen servants by his side, they would have a great shot at winning. Without him, not so much. Rias was probably recruiting people right now.

"So what's going on?" Riser asked.

"Well… I've got a Rating Game against Rias coming up."

"Against Rias?"

"We had an argument and this is how she wants to settle it."

"An argument about what?" Riser asked.

"Who wears the pants in the peerage."

"Well in mine no one is wearing pants," Riser said, smirking. "Seriously, you've got a game to decide who's the dom and who's the sub?"

"Basically, yeah."

"So what do you need my help for?"

"To beat her."

"What?"

"Come on man. I can't take her down by myself."

"Why the hell would I help you?" Riser said.

"Well if I win, I'll own her. I can make her do stuff."

"I can fuck her?"

"It's on the table," Issei said. "I'm sure we can negotiate a proper payment for you."

"If you win," Riser argued. "If you lose I get nothing. Worse than nothing. Rias will hate me forever."

"As opposed to right now?"

"Right now she just dislikes me. But maybe one day she'll realise it wasn't personal and I'm actually a great match for her."

"You don't really believe that, do you?" Issei asked.

"Maybe fighting for her will make her see that?"

"What?"

"Look, I like you. Arrogant little bastard that you are, I like you. You're a bit like me," Riser said. "But I don't want to fight for the losing side, okay? I'm sure that Rias will offer me just the same if I want to fight for her side. She knows she stands no chance against me. I beat her before and I'll do it again."

"I thought it would come to this," Issei said. "So why don't I offer you something right now?"

"Like what?"

"Asia?"

She swallowed hard. "Y-Yes, Sir?"

"Take out your tits."

"W-What?"

"Take them out," Issei repeated. His voice was calm, but firm.

She hesitated. No way she could do that. Not in front of Riser.

Asia's eyes pleaded with him, but he remained silent.

It was clear she wouldn't get out of this.

He had every right to make her do this of course. She had given herself to him completely, and she meant it.

With quivering hands, Asia grabbed the straps of her dress.

He was punishing her. That much was obvious. He had planned this all along when he told her not to wear a bra.

Asia pulled down the straps of the dress. It got caught on her large breasts. She pulled harder until finally, the fabric slipped down over her nipples.

As she felt the sudden loss of support, a wave of humiliation washed over her.

She looked to the side, trying to avoid Riser's lecherous eyes.

Riser chuckled. "Well look at that, she's getting horny from this."

"N-No I'm not," Asia denied.

But as she said it, she realised her nipples were painfully hard. Heat was pooling down in her belly. And if she reached down, she would probably find her panties were wet.

Was she turned out by the humiliation? Or was it just obeying Issei? Making him proud of her?

She felt the urge to lower her shoulders, but she resisted. She knew she had to push out her chest so they had a nice view.

"Odd," Riser said eventually. "I don't remember her to be that big. And I have a good memory for those kinds of things."

"She wasn't," Issei said. "She magically enhanced them."

"What? That is extremely painful."

"I know."

"I once tried to make Mira do it," Riser said. "But she couldn't handle it. It was too much."

"I didn't tell her to do this," Issei said. "I couldn't have. Like you said, it would have been too much. She's the one that offered it."

"How… How is that possible?"

"She wanted to be my little pet. And I agreed."

Riser swallowed hard. Clearly, he was very impressed.

Issei smiled. Clearly, he was proud of Issei.

"Well that's all very interesting," Riser said after a brief pause. "But I don't see the point."

Me neither, Asia thought.

When would he allow her to cover up again? Surely he wasn't planning to-

"Are you offering her body to me?" Riser spoke her thoughts out loud.

Asia swallowed hard. Please say no. Please say-

"No," Issei said forcefully. "She's mine. You are not touching her. This is as far as she'll go."

Asia let out a sigh of relief.

"You can cover up again," Issei told her.

Asia quickly fixed her dress. She pressed her legs together. Fuck, that was hot.

"I don't get it," Riser said. "You think this is enough to persuade me?"

"I was illustrating something. Asia wants to be my pet."

"So?"

"So what if Rias wants the same thing?" he suggested. "I believe that deep down, she does. But she's too proud to admit it. She needs to lose this game fair and square to admit it to herself."

"That's a big gamble. What if you're wrong?"

"Either way, she's mine," Issei said. "At least she should be."

"What do you mean?"

"She already lost fair and square. To you. You may have played dirty, but you won that Rating Game without breaking any formal rules. And the way she got out of it is unacceptable. I shouldn't have barged into your wedding like that."

Riser frowned. "Are you saying you will give her to me?"

"She belongs to you. She made a deal and she lost the Rating Game. So she's yours. If you want her of course."

"Why the hell wouldn't I want her?" Riser said.

"Well maybe you were going through the motions as well?" Issei suggested. "I know you, Riser. Rias isn't your type. She's way too dominant for you. And do you even want a wife? Plus you're not into redheads. You always fuck those catgirls twins together, but you prefer the blue haired one, don't you?"

Riser hesitated.

Issei and Asia stayed silent. It all came down to this.

Riser took a couple steps and sat down on the edge of his bed. His eyes were fixed on the floor.

"My family set up the engagement," he spoke quietly. "It's not like I could reject it. But to be honest, somewhere deep down, I think I was glad to get out of it. I never wanted Rias to be my wife. But that made me hate myself even more. Maybe that's why I was so depressed?"

"Maybe," Issei said.

"Even so," Riser stood up. His voice became more forceful. "She needs to admit that she lost. That bitch never did. I won fair and square and she needs to honor the agreement. I want her on her knees. I want her to offer herself to me. And then I want to reject her. I want to tell her I don't care anymore. You can have her."

Issei smiled. "Then you know what you have to do."

Riser hesitated. "Can I at least see Asia fully naked for a second?"

"No."

"Oh come on. This is not fair."

"Don't make me beat you again."

"Oh. You think you can handle me?" Riser puffed up his chest.

"Guys," Asia said. "It's okay."

"What do you mean?"

"Riser is helping us out. I think he deserves to be properly rewarded regardless of whether we win."

"Asia, you are not-"

"Me? What are you talking about? He doesn't want me."

"I don't?" Riser asked.

"My blonde hair reminds you too much of your sister."

"No it doe- oh crap. Now it does."

"Don't worry." Asia smiled. "I know a hot girl with pink hair that looks nothing like your sister. And she's always eager to help Issei out."

"Alright. But can I at least fuck her?"

"No," Issei said.

"Oh come on," Riser complained. "Why don't I ever get my way?"

"Why don't you ask one of your fifteen girls that?"

"It's fourteen," he pouted. "Ravel transferred to mom. Said I creeped her out too much."

"Oh, sorry, dude."

"I don't see why we can't take a bath together like we used to when we were kids," Riser said.

"Girls, am I right?" Issei said.

"Fine," Riser said. "I accept. But I want to see Rias' tits when we win."

"Fine. One time."

"Agreed."

They shook hands.

Asia smiled. Looks like Rias was going down.

Summary: Issei convinces Riser to join him in taking down Rias. He shows of Asia's obedience to him. Riser admits he didn't really want to marry Rias, he just wanted to satisfy his family.

A/N: Kudos to KaliYugaFan for guessing it was gonna be Riser