Warning if you are a fan of the Rias x Issei relationship this may not be the fan fic for you!

Disclaimer! No matter how hard I wish I do not own High School DxD in any way, shape, or form!

" " – Somebody Talking

' ' – Somebody Thinking

" " – Flashback

" " – Ddraig Talking

' ' – Ddraig Thinking

[ ] – Boosted Gear

Issei sat there in his room cold and alone. Sobbing as he could only think about where he went wrong. He had failed his master, Buchou. If only he were stronger, maybe he would have been able to save her from Riser Phenix. However, even though he failed his master and she was doomed to live a life she didn't want, that was not the main reason why he was sobbing. He was sobbing because he didn't care. After everything she did for him, she reincarnated him into a devil so he could continue living, she brought Asia back from the dead allowing him and her to be together forever, she gave him a better life.

And still, after all that he didn't care that she was doomed to live a life she didn't want to. 'What is wrong with me? She saved me and gave me a better life. Why don't I care? Am I without a soul or am I to ignorant to see all she has done for me?' As Issei was sitting on his bed sobbing a crimson light began to appear in his room.

From the crimson light he heard a vaguely familiar voice. "Hyoudou Issei-sama." Issei looked over and stared, as a silver haired beauty appeared through a magic circle. "Grayfia-san?"

"Hyoudou Issei-sama. I'm surprised you are even able to stand after all that. It was quite the beating you took after all." She said while looking at Issei's confused face.

"G-Grayfia-san. Do you know what happened? The last I can remember is tears falling on me then blacking out."

"Rias resigned from the match to save your life as Riser was going to kill you. You never gave up though, you kept getting up time and time again. You put up a good fight." Grayfia had said without changing the emotion on her face in the slightest bit.

"So, I failed her after all. I'm sorry Buchou. I'm so sorry." Issei mumbled while tears poured down his cheeks. Issei not knowing what to do looked at Grayfia with a depressed face. "What happens know? Is Buchou gone forever now? Will we ever get to see her again?"

"Now, Rias will become the bride of Riser Phenix. As for will you ever see her again, yes. She is still your King and will stay that way. However, Hyoudou Issei-sama. I have a message for you."

"A-a message? From who?" Issei said wondering who the message could be from? 'Has Rias sent me a message cursing me for not being able to save her? Even if it is that, I deserve it. I failed my master, there is no punishment that can make up for that.'

"Come on partner. You can't beat yourself up about this situation. There is nothing you could have done. You have only been a devil for a short amount with next to no fighting experience." A voice from within Issei's subconscious began to speak scaring Issei. 'What was that? Who was that? Am I going insane?' Issei thought franticly as he was looking around the room.

"Don't act like you don't know who I am! After all, this isn't my first time speaking to you." The voice said again in his head. 'Oh, it's you Ddraig. I have to be honest, it's still hard to remember there is a dragon inside of me that can talk to me at any moment.' Issei responded as he let out a chuckle.

Grayfia started to look at Issei very confused to why he was looking around the room and chuckling. Issei noticed her confused look and asked Grayfia. "Anyways, what's the message for me Grayfia-san? Is it from Buchou?"

"No. it is from Sirzechs." Grayfia responded with a serious look. "Sirzechs? Wait what? Why would he have a message for me?" Issei asked questioning why Sirzechs, the devil king of the underworld sent him a message.

"It is about Rias. His message says, "If you want to save my sister Issei. You better be prepared to fight." Grayfia said while pulling a piece of paper out with markings on it.

"Save his sister? W-what's that piece of paper?" 'Save Buchou? Maybe if I save her I can try and make up for failing her. But afterwords, I must get stronger to protect Buchou and the rest of my comrades.' Issei thought to himself while making a promise to himself to get stronger to protect Rias. Without realizing, this new promise put Rias on a highway straight to the friend zone.

"This paper will teleport you to the underworld. Were you can crash the party and save Rias." When Issei heard this his face lit up as he saw an opportunity to make up for his mistakes. "I have to go now. I am sorry for interrupting you I hope you can forgive me and I trust you will make the right decision Hyoudou Issei-sama." After saying that Grayfia left in the same transportation circle as before.

Issei sat there staring at the piece of paper putting himself through a dilemma. 'Do I try and save her? If I save her I can make up for failing her, however if I go there and fail her again I will no doubt be killed but also, I will have failed her even more. No. I must go! Even if it's a near impossible chance of saving her this is my only chance, and I must seize this opportunity.' After solving his dilemma, he could hear the voice inside of his head again.

"Partner, I will have you know there is a way you can put up a good fight with Riser Phenix, however, a worthy sacrifice must be made in return for power. That is the law of equivalent exchange after all." After hearing this Issei knew exactly what Ddraig meant and formulated a plan in his head. "Ddraig! We need to make a deal!" After saying this and sealing the deal Issei used the paper to teleport to the underworld. Not only minutes later his door opened as Asia stood there holding a bowl of water. After seeing that Issei was gone she started to panic, dropping the water leaving Asia wondering where Issei had gone off too. Or possibly who had taken him.


Issei had just used the paper Grayfia gave him to teleport to the underworld. As the light from the magic circle slowly started to slowly dissipate Issei noticed he was standing in a long hallway, in what seemed to be the inside of a castle. As Issei started running down the hallway, he could start to see a door in the distance. However, the door was guarded by guards and Issei had no idea how strong they were. Activating his Boosted Gear, he closed the distance between him and the guards in a matter of seconds. Overestimating the guards, he knocked each one unconscious with one punch each. As Issei stared at the door to what he believed to be the place he would save Rias from, he mumbled a few words aloud. "Buchou, I'm coming."

Issei then punched the door open. As everyone was staring at him he scanned across the room until he found crimson red hair. The crimson hair belonging to his master.

"Buchou!" Issei yelled while staring at Rias.

"Issei?"

As everyone in the crowd started wondering what was going on they looked at Riser Phenix and began to question him. "Lord Riser what is the meaning of this?" Riser couldn't do anything but stare in shock, as he did not expect the pawn he nearly killed to appear through the door of his home and try to take the woman he was going to take hand in marriage. As everyone was questioning Riser and demanded to know what was going on, a voice was heard as a crimson haired man resembling Rias stepped forward and said, "It's just a little entertainment I arranged." This man was none other than Sirzechs Lucifer, the Lucifer mauo. As everyone stared at the devil king Lucifer, Riser question him.

"What do you mean entertainment, my lord?" Riser questioned

"I watched the game Riser and I must say, I was underwhelmed. Despite your considerable odds you were almost taken down by my sister, a first-time competitor and her pawn." Sirzechs said with an unimpressed face.

"It is the final result that matters my lord." Riser scoffed at Sirzechs.

"Maybe in the past, but the games are not as important as they used to be. With that being said, I would like to give you a second chance." Sirzechs proposed.

"A second chance? What do you mean a second chance?"

"Phenix versus dragon, a good fight I like to think. So, tell me, do you accept?"

"I guess if the devil king requests of it I have no choice." Riser said.

"What about you dragon? Do you accept the battle?" Sirzechs questioned Issei.

"Hell yeah I do." Issei replied without hesitation.

"Very well. Tell me dragon, if you win what would you like in compensation?"

"Compensation? A prize for a low-class devil? Are you kidding me?" The crowd argued with Sirzechs.

"He is going through the trouble of this, so he will receive compensation if he wins. So tell me, would you like money, a maiden of beauty? Ask and you shall receive." Sirzechs asked Issei.

"There's only one thing I want. Rias Gremory!" Issei responded again without hesitation.

"Very well." With the conversation being over Issei and Riser were teleported to an alternate space with the others on the sides watching as spectators of the match. As Riser activated his flaming wings Issei activated his sacred gear and started to boost.

"Begin" the referee said while they both darted at each other. They exchanged fist when Issei jumped back and started to rant. "I don't have talent with swords like Kiba! And I'm not a genius like Akeno. I don't have crazy strength like Koneko, nor do I have healing powers like Asia, but I promise you Riser! I will take you down because there is one thing I have a whole lot of! Heart!

[Welsh Dragon! Over Booster!]

As a red aura started surrounding Issei it started to take the form of armor and started to materialize.

"This is the red emperors power! Try as you might, you cannot stop me!"

As Issei activate the Welsh Dragon Over Booster, he remembered what Ddraig said when he made his deal with him. "I accept your sacrifice and will grant you a power worthy of it, however, I will only give you to the count of 10! Any longer and your body will not survive!" Remembering that he heard Ddraig's voice in his head starting to count

10!

Issei leapt at Riser getting ready to punch him however Riser got out of the way knowing the punch would do a lot of damage even with Riser's immortality. Issei was sent flying but used the boosters on his back to regain his balance.

9!

After regaining his balance, Issei aimed his arm at Riser and formed a tiny red ball and punched it sending a blast at Riser. "Dragon shot!" The blast was too fast for Riser to react and was hit by it head on. After the blast faded he could see half of Riser's skin was melted off and even showing bone at some parts. As Riser's body started healing Issei leapt towards Riser again.

8!

Issei hit Riser down tumbling towards the ground crashing into the concrete floor. However, Issei started to puke blood from out of his mouth cause from the strain on his body because of the scale male. Issei then started ranting again. "I don't care what pain I have to endure. I will make up for failing Buchou and I will save her. Even if it takes up every last bit of my life force, I will save her!" Because of Issei's rant time was wasted. Time that Issei didn't have.

5!

As Issei notice he was wasting time he started to fly down when his armor broke and disappeared!

"Ddraig! You said I would have 10 seconds, that wasn't 10 seconds!"

"Sorry partner. Your body could not take anymore. If I would have allowed you to keep wearing it, you would have died."

Issei realizing that his plan had gone down the drain started mumbling again. "It's because I'm not strong enough again. It's always like this. Why? Why do I have to be such a pathetic weakli-" In the middle of ranting Issei had been picked up by Riser whose body had healed fully. As Issei looked at Riser with the same eyes that got him almost killed before Riser punched him.

"Those same eyes again Hyoudou! You idiot! You should have never gotten in between the affairs of the devils! And now you're going to die!" Riser screamed as his flaming wings grew bigger. The situation was similar to the one in the rating game. Issei defenseless, unable to fight, and on the verge of death.

"This time Rias won't be able to intervein and save your life. I'm going to make sure you're dead this time Hyoudou." Riser continued to beat Issei's face to a bloody pulp to the point where you can't even recognize it anymore. The light in Issei's eyes started to fade as he could only think to himself. 'Is this my punishment. For failing Buchou and thinking I was some kind of hero. I guess I lived a good life. I'm sorry Buchou, Asia, Kiba, Akeno, Mom, Dad. But it looks like this is the end.' However, an image flickered into his mind. It was Rias crying as she stopped Riser from killing him. It was the memory of when Rias saved him in the rating game. 'I never meant to make you cry Buchou. I'm such a pathetic servant. I'm sorry.' Suddenly, Riser started to see Issei's lips move and heard him say one word.

"No!"

"You're still alive! You idiot! What does it take to kill you!"

"No!" Issei said again.

"No! No! No! No!" Issei repeated himself.

Somehow Issei's face started to heal and a very strong red aura started to come off of his body. What this power is Issei didn't know but he wasn't going to deny it.

"No!"

"No!"

"I will not let you take her away from me!" Issei screamed as the red aura around his body grew stronger even destroying the hand Riser was using to hold onto Issei. The aura started to develop into the shape of armor.

[Welsh Dragon! Balance Breaker]

Suddenly, out of nowhere to the surprise to everyone, even Ddraig, Issei pulled out the balance breaker of the boosted gear. Two wings appeared from his back and his armor grew thicker than the Over Booster's scale male. Issei leapt forward and gave Riser a punch to the gut and started to form a dragon shot. [Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost][Welsh Dragon, Dragon Shot! Boosted Version!]

The dragon shot that Issei shot consumed Riser's whole body except for his head. Riser's body started to heal. Issei waited and let it, as he wanted to beat Riser to a pulp multiple times over. However, Riser's stamina was so drained that he knew he wouldn't be able to heal for much longer. Issei knowing this boosted several times again!

[Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost] [Boost]

"Please no. Don't do this! This is important for the future of all devils!" Riser pleaded

"I thought I already got the picture across! I don't care what could benefit from this. I am not going to let you take my master away from me!"

"Suck on this scumbag!" Issei yelled in rage

After boosting Issei shoved his fist into Riser's stomach and twisting it. After removing his fist from Riser's stomach Riser vomited an abundant amount of blood and collapsed to his knees. As Issei leapt forward again to kill Riser he saw a blonde hair little girl with drill like hair teleport in front of him.

"Don't hurt him" The girl screamed as she shielded him from Issei. Issei stopped and started to talk to the girl.

"I'd move out of the way if I were you little girl. Unless you want to be next." Issei said with a smirk on his face.


With that, the battle was over and the ground started to crack and disappear. As Issei was falling he was teleported back to the Phenix castle, but this time outside of it with the rest of the occult research club plus Grayfia and Sirzechs. As everyone was congratulating Issei on beating Riser the devil rumored to be immortal Sirzechs took out a piece of paper similar looking to the one Issei used to teleport here. However, when he used it a griffin was summoned.

"W-what is that?" Issei asked concerned. The animal was a gray color with a eagle like beak, 4 legs with 3 talons on each leg, 2 wings, and a tail. It was quite scary looking but also very cool.

"It's a griffin" Grayfia responded.

"Get on." Rias said to Issei asking him to take a ride on the griffin with her.

"Ummmm… Really? Me?"

"Yes, please." Rias asked while blushing.

"Umm ok I guess. If I don't die on this thing I'll meet you guys back at the ORC."

As the griffin took off and was high in the sky Issei noticed Rias was gazing at him longingly. It was at that moment he realized it. That same feeling from earlier when he was sitting on his bed sobbing. Not because he failed Rias but because, he didn't care.

"Silly boy you almo-"Rias was starting to say but was cut off by Issei mid-sentence.

"I'm sorry Buchou" Issei said with a depressed face once again.

"For what Issei? What could you possibly be sorry for?" Rias asked Issei with a concerned face.

"I just thought that I would feel different. I thought I would feel different if I saved you from Riser."

"Feel different? What do you mean feel different Issei?" Rias asked feeling really concerned and nervous.

"I just thought that if I save you from Riser, I would start to care."

"Care? What do you mean care Issei? Your starting to make me worry."

"About everything, at least anything. I realized it after we lost the rating game that I didn't care. And not just the rating game, but everything. I noticed there was nothing I cared about. I thought saving you would change that. But, I feel the same as before." Issei said, noticing that after hearing that Rias got very depressed.

"Oh, I see."

That's all that Rias said as they rode the griffin all the way back to the regular world in silence. Issei noticed that during the ride after he said he didn't care she started to cry but Issei thought it would be better to leave her alone.