Konohamaru beats up Naruto himself and makes Hinata and the Academy watch

With that in mind, Konohamaru soon got the plan in motion, convincing Hinata to head to the Academy the day after tomorrow to meet with Naruto there, and soon getting Hanabi to deliver the message to Naruto to get Naruto to meet Hinata there...

With that part of the set-up done, Konohamaru tomorrow found himself volunteering to oversee some stuff at the Academy, in order to give himself enough time to set up the trap for the flagpole wedgie, soon getting right to work, setting up a trap right there and making sure it was well hidden, and on top of that, setting up a more obvious trap near it, to try to goad Naruto to dodge that 'trap' right into the trap that would trigger the flagpole wedgie...

With that done, Konohamaru soon smirked and had a clone hide and oversee the trap to make sure no one disturbed the trap until Naruto came around tomorrow...

And when that day came around, Konohamaru had to move quickly to get himself right into position, this trap of his was going to use himself as bait, make it look like he was setting up something there the day of rather than beforehand...

So he was getting himself in the right position making a dummy trap that wouldn't get used as a clone was watching from where Naruto would meet with Hinata and would dispel itself the moment it found that Naruto had spotted it...

So Konohamaru was just relaxing as he was getting everything ready on his front, waiting for the moment to go as Naruto and Hinata was meeting as Hanabi had messaged Naruto to do so just as Konohamaru had intended...

When Konohamaru felt the influx of memories from the clone, he smiled before getting himself into position and just waited as he heard angry running as Naruto was rushing right for him as Konohamaru smirked and said, "Come and get me!" as Naruto snarled and ran right for him as Naruto was shouting, "I'm gonna make you pay for that last battle!"

Konohamaru just had to giggle at that as he continued to dart around, leading Naruto right to the trap he set up near the Academy Flagpole, dodging Naruto's attacks effortlessly leading Naruto up to the fake trap he had made, wanting to try to goad Naruto into dodging right into the trap that would trigger the prank as Naruto saw that trap and indeed Naruto dodged away from that trap, but didn't step right into the trap that triggered the wedgie up the flagpole as he smirked and said, "Is that all you've got?" as Konohamaru said, "I think you'll find that you've already fallen right into my trap!" before soon kicking Naruto in the balls, making Naruto wince and whine in pain before stepping backwards to trigger the trap...

The hidden seals that Konohamaru had planted soon got to work, soon firing out a hook attaching right to the back of Naruto's underwear, hooking it right up and soon pulling it up, showing that Naruto was wearing another pair of childish underoos today, this pair being an orange pair of underoos decorated around a kid's cartoon of a team of ninja dogs helping out in their village...

Something that made Konohamaru laugh and said, "I thought that pair of underoos were your only pair!" before soon laughing as the hook soon pulled up as Naruto whined in pain as he was shot up by the underwear, pulled up the flagpole until Naruto was hanging from the very top by his underwear as Konohamaru laughed at the sight of this, as Academy students came around to see this and began to laugh at Naruto as well...

Teasing Naruto for this and the underwear that he was wearing Konohamaru just couldn't resist laughing at the image this was as Hinata had followed and watched on, a bit shaken and taken a back by this humiliation for Naruto...

Konohamaru continued to laugh, which meant he didn't notice Hinata's eyes looking on at Naruto before looking away a bit embarrassed for Naruto, while the intended mission of making Hinata lose all interest in Naruto hasn't worked yet, even Konohamaru could tell that she lost a great deal of interest in Naruto as a potential romantic partner...especially as Naruto whined and withered in pain as he swung from the top of the Academy Flagpole, not only visible to the students below, but also some passerbys who were walking past the Academy on their way to do other stuff in the village...

The crowds of people were watching on as Naruto dangled as Konohamaru kept the trap up before soon calling out to Naruto, "In case you're wondering Naruto, it's currently Konohamaru 1, Naruto 0! I'm willing to let you off easy now, if you're willing to forfeit now and save us the trouble of the rest of the series!"

Naruto winced in pain before hearing that from Konohamaru and said, "No way! You may have won this round, but I'm getting you back in the next round, I'm pranking you back, Believe it!" bringing up his old catchphrase to seal it, and unintentionally increasing the chakra and strength drain going on from him to Konohamaru as he smiled wide as he felt the increase in strength as he called back, "If you say so! Just like today, I'll give you until the day after tomorrow to prepare for a prank! Also, good luck finding a way down!" as Konohamaru laughed before soon walking away, fully intent on leaving Naruto hanging from the flagpole to dangle there...

Naruto screeched at seeing Konohamaru walk off like that as the students were taunting him from the flagpole as Hinata continued to watch on, feeling quite embarrassed for Naruto and looking on him with pity, soon spotting something with her Byakugan and heading on over there, finding the seal that would lower down Naruto to the ground, and deciding to help out a little bit, by activating the seal with her chakra, however it also triggered a side effect in the seal if anyone else tried to get Naruto down...

The hook holding Naruto up by his underwear immediately disappeared, letting Naruto crash down to the ground face first from the flagpole, creating a Naruto-shaped impact in the ground as Hinata said, "Good luck with this challenge Naruto" leaving out the Naruto-kun she normally used, before soon saying, "Naruto-chan" feeling that somehow fit him more after this before soon leaving, the respect for Naruto as an equal and as a potential romantic partner was gone, but perhaps Hinata would soon begin to look down on Naruto, as someone older would on a younger person...

Shaking with pain from the crash Naruto soon growled out as he tried to get himself up and get away from the Academy but he soon found himself being accosted by, and kept from leaving for a while by the Academy Students who were eager to try to tease Naruto for being pranked like that before Naruto finally managed to get away to the safety and sanctity of his apartment...

As Naruto was at his apartment, Konohamaru was back at his house, already trying to think of another plan for pranking Naruto, as Naruto lost, he had the right to choose either the prank or a battle, and so chose another prank battle for the two of them to do the day after tomorrow...

With that Konohamaru looked back at the plans, the first of which being the previous Shopping District Spanking Machine plan he had drawn up before going with the Academy Flagpole wedgie that Naruto just got, it was a good plan, and it was a step up on embarrassment from the flagpole wedgie...

Konohamaru soon looked through the other ideas for pranks that he had for Naruto as well, before soon spotting another idea that he had drawn up...This prank would see to it that Naruto was stripped of his dignity before the village public, Konohamaru would employ smaller pranks in a public square on Naruto, to gradually strip him of all of his clothing, leaving Naruto in nothing but whatever childish underoos he had decided to wear that day...

Smirking a bit at that image as well, Konohamaru soon thought about those plans and the other plans he had been working on before soon deciding on his plan for his next prank, and soon getting the stuff ready to get that prank ready to go...