Disclaimer : I do not own High School DxD, or anything to do with the franchise. These characters and events belong to their rightful owners.

A/N: Seeing how little interest this story is getting, then I am not to bothered about chapter length. A total of two reviews for the last chapter, but plenty adding this to their favourites and following list.

Occult Research Club Old school Building

Rias Gremory, lounged back in her chair, reflecting on everything that had happened it the last few weeks. She had two new servants and one potential all with their very own Sacred gears. It had been a few days since the stray had been vanquished, Issei and Asia were now back at school, after his little mishap, and things were running smoothly. Rias had taken the this time to explain to the Issei and Asia about familiar and their roles in working with devils. They had visited the Familiar forest yesterday and Asia now had a cute blue baby dragon, as her familiar. Issei however didn't find one, well he did, but there was no way in hell Rias would let him have it. The thing was made up of green slime and she and the girls had managed to get tangled up by the nasty little creature. It wasn't being tangled that had Rias upset, but what the creature did to clothing, when it touched them. It disintegrated them away from the body, and all four of them had ended naked. Of course this made Issei very happy and he insisted on catching it, but after the glares he got from all the others, he decided maybe it wasn't such a good idea. The other major event was that Sona had finally bought her own servants to meet Issei and Asia, Rias smiled as she recalled Issei reaction to other devils being in the school. However that smile soon vanished as she remembered what had happened earlier that day.

Flash Back

Rias was sat at her desk, when she noticed a magical circles appeared in the room, she noticed the seal was that of the Gremory household, she stood from her desk, ready to greet, whichever member of her family that had decided to pay her visit. Rias noticed a woman, with sliver long hair, appeared, she was dressed in a black and white maid outfit. This was Rias sister in law, and her name was Grayfia. She was also the wife to the current Lucifer, and cared a great deal for Rias.

"Sister, its good to see you again, please come and sit down. Would you like some tea?"

Grayfia inclined her head and smiled weakly, she wasn't sure how she was going to tell Rias, about the suppose engagement. Lord Gremory and Lord Phenex had got together and agreed that both their children would marry, this marriage would be an political move for both families, however Grayfia knew how Rias felt about her suppose fiancé, his name was Riser Phenex and he was the next head of the Phenex family. He cared very little for his servants, and cared more for himself then anyone else. Riser and Rias had known each other since they were little, and the two never got on, mainly because the way Riser treated his servants. Like most high class devils in the underworld, everyone of his servants were female, and he seduced every single one, without giving a second thought to how his servants might feel about the whole ordeal. Grayfia knew Rias wouldn't want someone like that, but the marriage had been arranged and there was no way out of it.

Grayfia took the offered tea and placed it on the table, she then put her hands in her lap. "Rias, there is something we need to discuss. You know Riser Phenex?" Grayfia noticed Rias flinched at the name. "Well your parents and Lord Phenex have decided that you two will be entered into a marriage contract. They hoped the marriage with strengthen the bond between the two families. You are to be wed after you graduate next year."

Rias eyes widened, this couldn't be, her parents knew how she felt about Riser, why would they even think of doing something like this. Rias stood from the sofa, and paced across the room. "How could mother and father do this to me? They know how I feel about Riser, he nothing but a womanising pig! All I would be to him his a trophy wife and a fuck toy, well sorry that's not good enough. Grayfia, please there must be a way out of this. You know as well as I do, my brother won't stand for this, he hates Riser as much as I do."

Grayfia sighed, Rias was right, when she had told her husband, he had hit the roof and immediately left to speak to his mother and father. He was yet to return, but Grayfia thought Rias had a right to know on what was going on. "You're right, Sirzechs was also unhappy, and he has gone to see what he can do to help you out of this."

Rias sighed, this couldn't be happening, she had very few options available to her, and not a lot of time. She just hoped that her brother could pull enough strings to give her at least a chance in fighting this.

End of Flashback

The problem was the only real option she had to get out of this marriage was to lose her virginity. She knew Riser wouldn't put up with someone else claiming her first. The thought that she had slept with someone else would drive him mad. Still if it diverted his interest away from her, then in Rias book, her virginity was a small price to pay. She was still to hear from her brother, and had no further contact with Grayfia, since earlier today. She knew she couldn't wait too long, every minute that past meant Riser getting that much closer. Rias stood from her desk, this was the only way, but now her problem was who? Kiba was out, Rias had no real romantic feeling towards her knight, he had always been more of a brother to her. Rias then thought about Yusei, but then she thought how Akeno would feel, if she claimed Yusei first before she did. Her friendship with Akeno was far more important than losing her virginity. Her last option was Issei, there was no doubt he would do it, Rias only problem was, she didn't want to come across of being too easy, Rias wasn't a slut, far from it, to be honest no boys had peeked her interest, that was until she met Yusei and Issei, both had qualities about them, that made them good relationship material, Yusei, more so than Issei. Still Yusei was off the list due to Akeno so she only had one option. She would make sure Issei knew this was a one time deal, just in case he got it in his head, that he could fuck her whenever he wanted. Rias created a magical circles and then stood in the middle of it.

Issei Room

Rias appeared in Issei room, and noticed he was fast asleep in bed. She stepped out of the circle and tiptoed across the room to the side of his bed. She was very nervous and was seriously thinking about forgetting the whole idea. That of course was before she saw an image of Riser hovering over her naked and laughing. Rias cringed and gently prodded Issei.

"Issei, it's Rias, please wake up, I have something I need to talk to you about urgently." Rias noticed the mass of covers moved and Issei head poked out from under the quilt, his eyes were half closed, but as soon as he saw Rias, they widened and he shuffled up the bed, and rested his back against the head board. He switched on his lamp and noticed that Rias seemed rather sad.

"What's wrong Rias, you look like your about to burst into tears.." Issei was cut off by Rias falling onto him, and wrapping her arms around him. Issei could feel her shaking, what on earth had caused this. "Rias what's wrong?"

Rias didn't say anything for a little while, she felt safe in Issei arms, however eventually she calmed down and started to open up. "Issei, something has happened, and you are my only hope. My parents have entered me into a marriage against my will. I am to be wed to another high class devil next year, the problem is I hate him! I don't want to marry him. My parents want to form an alliance with his family. The only way I can get out of this, is if someone takes my virginity. Riser, wouldn't want to touch me then, he would force his parents to call off the whole thing. You see Riser, is nothing more than a womanising pig! All his servants are females, and he sleeps with every single one of them. However he would see me as his greatest conquest, and I want to take that away from him. So I am asking you, no begging you, Please take my virginity. It's the only way to safe me from this arrangement."

Issei was speechless, Rias Gremory, was here, in his room, demanding he took her virginity, Issei noticed Rias had already started stripping, soon her shirt, and skirt had been discarded, next was her bra and panties. The moonlight through the window caught her body just perfectly. Her long Crimson hair, wavered in the small breeze and wrapped itself around her naked flesh. Issei mouth dropped, he had never seen anything so beautiful. The moment was soon ruined thought, when Rias straddled his waist. Little issei was wide awake now. Issei gulped, this was his fantasy coming true, however something was holding him back. He looked at Rias and stopped her from grinding down on Little Issei.

"Rias, this is wrong, any other time you know I would do anything for you, but this is your virtue we are talking about, losing it just to get out of a marriage arrangement. It's not fair, I can't do this to you, I can't violate you like this, I would never be able to forgive myself."

Rias was about to argue, and tell Issei this is what she wanted, when she was distracted by another magical circle, appearing in Issei room. It was Grayfia again. Rias noticed she looked worried and upset.

"I was too late, I thought I would have more time?" Grayfia noticed that Rias, climbed off Issei, she then noticed the boy still had his boxers on, she sighed in relief. "Rias I came to tell you that your parents are giving you an opportunity, to get out of this arrangement. Your brother has persuaded your father and Lord Phenex to let yours and Riser fate be decided in a rating Game. You will have one week to prepare. You and Riser will then face each other. If you win, then the engagement will be voided, however if Riser wins, then the engagement will go ahead. Your brother as also decided since you are a few pieces down, then you may add the boy known as Yusei to your ranks, just for this event. Will you accept these terms, Your brother sent me to get your answer."

Rias sighed, Riser was one of the top devils in the Junior Devil rating games, he was unbeaten, Rias wasn't sure how this was going to help her, however it was chance, a chance she couldn't afford to miss out on. "Tell brother, that I accept the challenge and the terms, and thank him for giving me this chance."

Grayfia inclined her head, and then vanished, leaving Rias to get dress and Issei just left in bed looking bewildered by the whole thing.

Rias buttoned up her shirt and slipped on her panties. She then leaned down and kissed Issei. "Thank you Issei, I was at your mercy, and you didn't take advantage, even when you had the permission too. That says a lot for your character, you may be pervert, but you also are one of the kindest souls I have ever encountered. I mean look what you did for Asia, and now me. Thank you Issei." Rias then kissed him once more. "She then walked over to the centre of the room, and created a magical circle. She stepped into and looked towards Issei once more. "Come to the club room after school tomorrow, we have a lot to discuss and very little time." Rias then vanished from issei room.

Issei head fell back on his pillow, he was about to close his eyes and go back to sleep, when he noticed his door open, and Asia tiptoed into his room. He felt the quilt lifted by his feet and someone crawling up under the quilt. He then smiled as Asia head popped up beside him.

"I couldn't sleep Issei, can I stay in here with you again?"

Issei smiled and wrapped his arms around Asia small body, and drew her in closer to him. He allowed her head to rest on his chest. He then kissed the top of her head and closed his eyes.