Timeskip 12 years into Issei's 2nd year at Kuoh Academy
It's been 12 years since The Shidou Family left Kuoh and now Issei is in his second year at Kuoh Academy. When he first started at at Kuoh Academy, many of the girls were enamoured by his cold and stoic attitude so much so that he became one of the two Princes of Kuoh Academy, dubbed the Ice Prince of Kuoh due to his stoic and cold attitude.
In that time he made friends with the Perverted Duo, Matsuda and Motohama, when they tried to drag him into their perverted activity he coldly shut them down despite being friends he said he would never be a pervert, which was the reason which many of the girls started referring him as the Ice Prince.
We now jump in as we find Issei in class ,while his two perverted friends are discussing their antics.
Motohama : Matsuda I found a new peeping spot, we should go there during lunch
Matsuda : A new spot to admire women
Motohama : Issei you should come with us , I promise to make it your worthwhile.
Issei : *coldly* No thanks guys, I for one don't wish to be chased around with kendo sticks during lunch and I've told you guys before to stop doing these things they'll end up getting you hurt
Matsuda : Awww come on Issei let's go
Issei : Nope guys I said no, I'll just sit under a tree while you guys get chased around , enjoy though
*During Lunch Break at Kuoh*
Issei is seated underneath a tree ,just relaxing when he feels eyes on him , as he looks up the old school building he sees a red haired girl looking at him before heading back inside . The Red Haired Girl is Rias Gremory, one of the 4 Great Ladies of Kuoh Academy as she looked down at him ,she notices him looking up at her before heading inside.
As she heads inside she is met by a girl with long raven coloured hair tied in a long ponytail , violet eyes. This girl is Akeno Himejima, the 2nd of the 4 Great Ladies of Kuoh Academy as she's seated playing chess with Rias ,speaks.
Rias : Akeno who is that boy seated under the tree outside
Akeno : That is Issei Hyoudou, Buchou, not much is known about him ,but he has a cold and stoic attitude which caused people to call him the Ice Prince of Kuoh direct opposite to Kiba's White Prince.
Rias : I feel a strange power coming from him.
Akeno : Perhaps it's a sacred gear? Check
Rias : Maybe , probably he'll help with my issue?
Akeno : Maybe? Are you going to keep him under surveillance?
Rias : Yes, Checkmate.
Akeno : Awwww, and I thought I would get you this time around...
Rias : Maybe next time ,Akeno, who are you really Issei Hyoudou?
As she wonders , she calls in Koneko.
Rias : Koneko.
Koneko : Yes Buchou
Rias : Keep an eye on Issei Hyoudou, he is a person of interest, I sense the fallen are about to make their move on him.
Koneko : Yes Buchou
Timeskip to the end of school
As Issei walks home , he encounters a young lady with Black Hair and Violet eyes
??? : Are you Issei Hyoudou?
Issei : Yes I am , who is asking?
??? : My name is Yuuma Amano, I've had an eye on you for a while and I was wondering if you would be my boyfriend ?
Issei : Is this a trend among girls to ask out boys who they don't know on dates?
Yuuma : *fake blush* No I've genuinely had an interest in you and I wanted to ask you out on a date.
Issei : I won't be your boyfriend till I know more about you but how about we go on that date on Sunday , meet me at the shopping district at 10 AM?
Yuuma : *fake blush* Sure ,I'll meet you then.
Issei : Good then , I'll see you then.
'In a nearby bush'
Koneko : I have to tell Buchou about this.
Back at the ORC
Koneko: Buchou , a fallen angel has made contact with Issei, they are going out on a date on Sunday.
Rias : I'll have my Familiar give him a summoning circle .
The next Chapter will be Issei going on a date with Yumma, stay Tuned, cheers