Disclaimer: I don't own Ouran High School Host Club. It is made by Bisco Hatori.
I made a story as a continuation of the first season. Mainly this is for the anime lovers although there's a lot of manga version happening within my story (just for connecting plots together). In my imagination, if there's a Season 2…I hope it would go something like this. Note that I continued from where the last episode left off and assumed some parts of the manga occurred already. But for the story's sake, we would follow what's happened in the ANIME than the manga okay? Unless, it is stated otherwise. SKIP READING BELOW IF YOU DON'T WANT MANGA SPOILERS. IF YOU'VE SEEN ONLY THE ANIME, THAT'S ALL THAT MATTERS. TO THOSE WHO HAVE READ THE MANGA, IT'S BEST TO READ HERE TO AVOID CONFUSION. CHAPTER ONE BEGINS NEXT PAGE.
Example, I have assumed that episode 42-45 has happened, therefore the host club already knew about Mei and Kaoru has already figured out their feelings for Haruhi. Also, episode 46-49 are assumed to have occurred so as to emphasize Tamaki and Kyouya's friendship. It means the host club is already acquainted with Kuze and the football club, thus the sports festival and every conversation there has occurred and it had been decided that the second years will have a field trip at France. We're skipping the part of episode 50 about everybody worrying about Tamaki's trip because in the anime, Haruhi hasn't found out about his family 'till the end. So episode 51-53 has occurred 'cause the twins real fight is important; the support between Hunny&Kaoru and Mori&Hikaru plus Kaoru's confession to Haruhi; and the twins getting along again but just note that nobody's dyed his hair black YET. Next, it's best to think that the episode 54 is included but only until the part where Tamaki sent an idiotic message to Kyouya while the latter was at France, the rest of that episode will be incorporated with the story. Skipping episode 55, the part where Tamaki discretely spied on Haruhi's house and got caught, let's have episode 56 to happen instead—Kyouya's actual meeting of Tamaki's mom. Just leave the part where Kyouya returned already because that will be part of the season 2 (or my story, haha!).
Now going back the start of Season 2 before beginning…again, we will take the anime version of the fair and not the manga…so there's no 'rich men poor men' game so we might be able to add that in this season 2 (cause it's very interesting).
PS: IMO, the anime is really rooting for KyouyaxHaruhixTamaki if we base it to its ending compared to the manga's Hikaru and Tamaki fighting over Haruhi. With the way Hikaru realized how important Tamaki and being 'friends' with the host club is to him during the time he injured himself at the last episode, it seems like he isn't so much conscious about Haruhi compared to Kyouya…the way he looks at her especially after she defended him from his father. I took notice of his actions after that and you'd definitely see that Haruhi has got him there! Hahaha! Like he keeps staring at her when she was looking at the clock; Haruhi's comment about Tamaki's nonattendance made him furious to call the mansion 2 and every interaction they had that followed. Not to mention, his father's intention. So yup, there's no doubt that the anime wants a KyoxHaruxTama sequel. I had a hard time squishing in HikaruxHaruhi in the story because I really wanted the 'season 2' (AKA this fanfic) to be as close as I can possibly relate to reality (which is Bisco Hatori's imagination of them). But here goes the first few…enjoy!