he Academy Flagpole Wedgie Plan

Konohamaru decided to with the Academy plan to already build the foundation of his "bosses" demotion after their challenges were over. Naruto was flustered now and would be easy to deal with once he had successfully gotten him to the academy grounds.

The only thing he was struggling with was how to get the spiky haired teen to get towards the academy in the first place. Then he remembered the busty heiress of the Hyuuga clan that used to follow him and Naruto around back in the day.

Although too shy to get more than a word or two out towards Naruto, she was one of the people he was most friendly with. He always had a big crush towards the blue haired girl and hated how she admired Naruto and how he never got the hint about how much the girl liked him.

He never got how his boss could be this blind towards the attention of the Hyuuga princess, the most powerful and prestigious clan in Konoha, whom also looked absolutely gorgeous. He was head over heels for his pink haired teammate yet ignored Hinata? Well fine, then he would make sure Hinata would lose all interest in him.

Why not kill two birds with one stone? He could lure Naruto towards the training grounds under the pretense of meeting Hinata there, and do the same in reverse with Hinata.

Once he beat up Naruto and **** him onto the flagpole or perhaps tricked him somehow, not only would he have managed to score an important point in their challenge while already making Naruto a loser in the eyes of the academy students, but also manage to impress Hinata and humiliate Naruto in front of her.

If Naruto resisted his punishment after his victory, he could perhaps even make some Academy students part of the bet if Naruto was weak enough already after their battle so that he could further hammer home the humiliation of the dare via having Naruto defeated by somebody from the Academy instead of him. Forcing him to boy him was fun, but making an academy student put him in his place also sounded attractive...

Liking this train of thought more and more, the young Sarutobi set out to fulfill his plan, and began to march towards the Hyuuga clan district to make his vision into reality.