I do not own high school DxD

Issei will have his harem and then some list will be at the bottom

Will have some characters from other anime but only if I find it appreciate

Issei will have some of the personality of the sins like Meliodas being carefree and a little pervert ban arrogance

''normal talking''

''spirit/animal talking'' sentient sacred gears

''techniques''

It is the morning after Issei challenge Riser for the hand of Rias and he is waiting for someone to come and get him when a summoning circle appeared underneath him then he was in a battle arena in the underworld and in front of him Riser stood there with his entire peerage then there was announcement ''greeting I am Grayfia head maid to the house of Gremory and Queen to Sirzechs I will be the referee for this fight now Sirzechs has something to say''

''Greeting as Grayfia just said I am Sirzechs now I would like to ask Issei something'' Sirzechs said before turned his attention to Issei and said ''now Issei should you win this what would you like as a reward''

''what a reward for this insect'' Riser said shocked Issei

Meanwhile was thinking when he said ''how about my home bigger''

Sirzechs who was not excepting that said ''and why would you want that as a reward when you could ask for so much more''

Issei stood there and said ''well for starters I am happy with what I have and another when I do win this, I will be getting fifteen beautiful girls and frankly my home is at its limit with me my mother Ophis and Tiamat then there is Rias she does like to pop in and get into my bed when I full asleep''

Sirzechs took a few moments to think it though then said ''very well then you will get a bigger home should you win this now I will hand you back to Grayfia''

''thank you Sirzechs now then let the game begin'' Grayfia said

Meanwhile with Sirzechs he was talking to the masters of the Ryozanpaku dojo who was talking to Rias said ''thank all for coming on short noticed''

Hayato said ''think nothing of it imagen my surprize when he showed up with Rias and her entire group and when Issei told us about the whole thing and what kind of person he was we wanted to do something, so we trained them''

Akisame looked at the king and said ''so Sirzechs how much did you pay Issei to get your sister out of the marriage''

Sirzechs looked at the masters with a little sweat and said ''the thing is I haven't paid him yet and before you get mad at him and try and kill me the payment is not with money but I will release Grayfia after the match but Issei doesn't know that at the moment''

Akisame looked like he was thinking then said ''smart idea with the mystery payment that normally gets people motivated and we have no problem with that but the problem will come if you don't pay up''

Shigure turn got everyone attention by saying ''what power you think Iss-kun will use''

Kensei said ''well now that is a good question well is certainly can't be the lion sin as there is no sun in the underworld''

Shio then said ''maybe he might use the fox sin

After a few minutes of discussing Sirzechs said ''umm what are you all talking about''

Hayato looked at the devil leader and said ''well to put it simply Issei is more powerful than anyone''

''I doubt that is possible'' Sirzechs said not believing what he just heard

Hayato looked at the crimson man and said ''I see you don't believe me but that doesn't change the fact that Issei has eight different powers, one of them allows him to increase or decrease his strength depending on time of day, another one allows him to manipulate the earth, then you have the one that sent any magical attack back at the caster with double the power he also has one that allows him who dies then there is the one that allows him to enter someone's mind and change anything he wants if used incorrectly, he also has a power similar to forbidden balor view another power is a much stronger then divine divide and the last one is ki''

Sirzechs said ''well then I better not piss off the kid the then''

While Hayato was talking to Sirzechs Shio turned to Akisame and said ''hey Aki I bet my pudding the he uses the fox sin''

Akisame said ''I will take you up on that offer for me it will be the boar sin''

Hayato heard what Akisame said walked over and asked ''betting on my grandson are we''

Sakaki looked at the old man and said ''yes but it is a fool bet to bet agents him so it's just what power he uses as we know he will beat this devil and it is our pudding we are betting''

Hayato looks forward strokes his beard and said ''okay I will bet he uses the serpent sin''

Kensei wanting in on the bet says ''I will join and say he uses the goat sin

Shigure looks over and says ''I bet he uses the dragon sin''

Apachai looked at everyone with a lost look and says not knowing what is going on '' Apachai will bet on the grizzly sin''

Ophis who was taking notes on the bet looks at Apachai and told him ''you know Apachai whey are betting their pudding so if Issei doesn't use the grizzly sin you wont be getting your pudding tonight'' and Apachai just nods

Back in the arena the moment Grayfia said begin Riser said ''now boy Riser is feeling merciful so how about you just surrender and save yourself being humiliated''

Issei replied ''funny I was a bout to say the same thing''

Riser not liking what was just said turned to his peerage and said ''alright girls go and attack that scumbag, and don't you dare hold anything and don't let up''

Issei just stood there as the peerage of his opponent surround him when they started to attack him, he didn't even flinch and just took it with a smirk

After ten minutes of constant attack when Riser said ''okay you can stop now'' when they all stopped Riser stood there with an arrogant smile as he watch the big ball of fire before him waiting for Grayfia to declare he is the winner and when the call didn't come he said ''hey the battle is over declare me the winner already''

Before Grayfia could say and thing Issei walked out of the fire in a badass way without a scratch while on him while saying ''well I think the reason that Grayfia hasn't proclaimed you the winner might be because I am still able to fight''

Riser growled then fired fire balls at Issei but Issei didn't dodge the ball then looked at his peerage not doing anything shouted ''what are you lazy bitches doing attack him again and don't let up''

Back with crowd Sirzechs look at the masters and asked ''why doesn't he dodge the attacks after he should be fast enough to dodge''

All the master looked at each other then looked at Sirzechs and Hayato said ''we don't know''

And before anyone could chat about what Issei was doing Ophis said ''he might be planning to use revenge counter''

Everyone looks at the dragon and Sirzechs asks ''what is revenge counter Ophis''

''it is an advance technique of full counter that requires him to disable his magical power which allows him to store and charge every magical attack he receives then releases then all at once'' Ophis said shocking everyone

Hayato was first to come out and asked ''wait Ophis with the amount of magical powers he has stored wouldn't he''

''Explode yes when this technique is used, he literally becomes a ticking time bomb'' Ophis stated

Back on the battlefield Issei smirked then set his arms into a cross and then a tremendous amount of power started to surround him coursing high winds then with his speed run to Riser and before he could reacted Issei said ''revenge counter'' then he exploded coursing all of Riser and peerage to scatter by the force of the explosion and all the latter was knocked on conscience

Riser being the closest was injured the most and was on barely conscience saw Issei coming over said while trying to stand ''I cannot and will not lose I am a member of the mighty Phoenix clan''

Issei looked at Riser and said ''and that is where you will fail and lose in this match you are to reliant on the power that makes you unbeatable but when it come to someone that has a similar power like I do it will come down to who to the one that trains more and that is your sin'' then Riser mustering all the strength he muster manages to punches Issei with an upper cut and punch was surprisingly strong as Issei flips then grabs Riser's wrist then begins to beat him like a rug after about a minutes or so Issei starts to spin while still holding Riser then throws him to the furthest wall low to the ground when Riser hits the wall there is a small but thick cloud of dirt/dust

When then cloud we find Riser upside down and on conscience then Grayfia said ''Riser Phoenix is on conscience and there for retires winner of the Rating games is Issei Hyoudou and has won the hand of Rias Gremory for marriage and the peerage of Riser Phoenix'' then everyone in the arena glowed then teleported to the infirmary to get everyone healed up

With the dojo masters Hayato then said ''well it looks like Shigure will be having our pudding tonight''

Issei was about to leave when he heard someone calling him he looked and saw Sirzechs and Lord Phoenix also his grandfather and masters heading his way before anyone could say anything Issei said ''I am heading home now I will come and pick up what you owe'' then disappears

Issei reappeared in an alleyway in his block he stuck his head out to see is anyone was there then walked home when got home he saw his mother and Tiamat watching tv then said ''hey mum Tiamat how have you been over the last couple of days''

Miki looked at her son and said ''been a bit boring but at least I had compony''

Tiamat said ''same here so what have you been up to''

Issei sat down and said ''well to start of the Gremory and Phoenix had a marriage contract with between Rias and a jackass call Riser and the only way out of the marriage was to beat said jackass so that night I kidnapped them and took them to jiji to train but they still lost then Grayfia came and said that Sirzechs has a job for me but I will not know what the payment is till after I do the job so I accept it and in doing so a decided to crash a wedding got into a fight with Riser for the hand of Rias but he decided to throw in something extra as he wanted Ryozanpaku Dojo so he said if he won he get the dojo then I thought about it and saw the looks on the girls he has in his peerage and said I get his peerage if I win he agreed and today I beat the shit out of him well I am going to bed as I have a meeting with Sirzechs and the head of phoenix tomorrow'' and was about to head up stairs when he remembered something ''ahh yes mum'' getting her attention before continuing '' before the match Sirzechs asked if there was anything I wanted and I said a bigger house as it is getting as bit crowded in the house with you me Ophis and now Tiamat and adding 15 new girls there will be no room around here so I will be seeing Sirzechs first to see what my payment is for getting Rias out of marring the jackass also you are to come with me to the underworld as you own the building and you should get to choose how it looks then I will be going to get the girls from the Phoenix'' then went to bed

The next morning

Issei and his mother are in the lounge ready to head to the underworld when Issei said ''are you ready mum''

Miki took a deep breath looked at her son and said ''ready as I'll ever be'' then Issei used a teleportation spell to the Gremory mansion

When they arrived, they were met by Grayfia who said ''welcome to the household of the Gremory family''

Issei walked up to Grayfia and said ''hey Fia do you mind taking us to see Sirzechs for payment for getting Rias out of the contract and for the house which is why my mother is here and I need to pick up the girls from burnt out turkey''

Grayfia looked at Issei with a smirk and said ''of course right this way'' then lead them down the hallway when they got to Sirzechs study Grayfia knocked and said ''Sirzechs Issei is here with his mother about the payment for the job and the reward''

''let them in'' came Sirzechs voice Grayfia then open the door and let them all walked in Sirzechs said ''please have a seat Issei you to Miki'' when both of them took a seat Sirzechs continued ''firstly I want to say is thank you for doing what you did Issei and congratulation on the win I knew you was going to win even though I sounded like I didn't''

''I understand even though you hired me knowing I would beat Riser you had to pretend that I might lose'' Issei interrupted Sirzechs

''thank you for understanding Issei'' Sirzechs said before continued ''now then where was I ahh yes another congratulation is in order on you engagement to my little sister'' Sirzechs teased before continuing again ''now then on to the important stuff Issei your payment for the job is Grayfia is now staying with you when we build the house''

Issei shocked by this said ''are you sure and I hope this doesn't sound like I don't want her to live with me, but doesn't she have duties being the queen of your peerage''

Sirzechs looked at Issei and said ''the real payment was releasing her as my queen so she can be with you more often and before you say anything, I did ask her, and she said she was fine didn't you Grayfia''

''that is correct Issei I did say I was fine being released after I get to spend more time with you'' Grayfia said which ended up with her hugging Issei

''now then on to the final bit of business the reward foe the bigger house and I am guessing that is why you brought you mother along'' Sirzechs said

''yes I might have won the match the house is still hers so she need to be there for the planning that is if she wants the house bigger'' Issei said then gets up and walks out while saying now I am going to leave you two to plan while I am going to the phoenix'' Grayfia decide escort him out when they were at the door Issei looks at Grayfia and asks ''hey Fia which way to the Phoenix estate''

Grayfia points the way and say ''it is that way''

''thanks, Fia'' Issei said before giving her a kiss then flying off

After about half an hour of flying Issei came to the Phoenix he lands at the front door and knocks a couple of minutes had passed when a butler answered the door and asked ''hello young man what bring to the Phoenix household''

Issei looks at the butler and says ''hello to you to I am Issei and I am here to see the lord and lady Phoenix''

The butler says ''ahh I see then please come in they are expecting you and I will take you to them immediately'' Issei then follows the butler

When the duo came to a door, the butler knocked on the door then they heard ''come in'' the butler open the door Issei walked in then lord Phoenix said ''ahh Issei was just telling Riser that he has to give you his peerage due to the deal that you made''

Then Riser shouted ''I refuse to hand my peerage over to him''

Lord Phoenix looks at his son and says ''you have to we Phoenix are part of the 72 pillars we have to keep our word that me make other what example are we giving to the younger and lower-class devils''

After an hour arguing lord Phoenix said ''Issei is getting your peerage as you made the deal you need to honour as I know that if Issei lost he would have gave to the Ryozanpaku heir title the moment he regained conscience and do you want the master coming here as you cant uphold a deal'' then he called a butler

when the butler showed up, he asked ''what can I do for you sir''

''will you get Riser's peerage and bring them here so that their new master can take them'' Lord Phoenix replied

''will do sir'' the butler said then gave a little bow then left

Fifteen minutes had gone by when there was a knock on the door then the door opened revealing the butler and the Riser's former peerage then lord Phoenix noticed the worried looks that some of them have and said ''welcome girls now let me say one thing before we get to the reason I called you girls here none of you are in trouble now then you see the match you had yesterday with this young man here'' point to Issei ''was about the hand of Rias''

A purple haired one stepped forward and said ''we know that sir but why are we here''

Lord Phoenix said' 'Riser told you about that then, but did he tell you that he upped the ante''

Yubelluna looked surprized said ''what do you mean Sir''

Lord Phoenix said ''well to simply put Riser bet that if he wins he gets Issei's title as heir to the Ryozanpaku dojo but if Issei win he gets you lot and we know who won the match and now Riser's is refusing to uphold the deal that he made so you all belong to Issei now''

After another hour of talking and finalising the deal Issei left with his new maids for the house and headed to the Gremory household when the group got there, they see Miki waiting with Sirzechs and Miki told Issei ''the house is now a six-story building with three basements''

Sirzechs then said ''and it should be finished, and you mother has agreed to take Rias and her peerage in and for that I pay all the main bills so all you have to worry about is getting the food'' and with that they left for their new home

The next day at school the teacher came in gets to the pedestal looks to the class and says ''alright call we have four new students joining us today'' then turns to the door and says ''you can come in now'' the door opens up to reveal

That's all folks

In harem Grayfia, Ophis, Shigure, Rias

Going to join, Akeno, Keneko, Kuroka, Xenovia, Asia, Irina, Rossweisse, Riser's peerage, Tiamat