Perhaps in a fanfic, Naruto dresses as a girl to enter a beauty contest in the Hidden Leaf Village. This could lead to humorous situations like him trying to do makeup and hair styling. He could also use his skills in a unique way during the contest, like using his ninja agility to perform an amazing dance routine, which would be a new take on the traditional beauty contest.
One idea could be that Naruto dresses as a girl for a mission. Maybe it's a stealth mission where he has to infiltrate a female - only place. He initially struggles with acting like a girl but then starts to learn the nuances and even uses his new identity to gain unexpected allies.
Another plot could be that Naruto is forced to dress as a girl as a prank by his friends. However, he ends up enjoying the new experience in some ways. He could learn about how girls are treated differently and gain a new perspective on gender roles in the ninja world. For example, he might notice how people are more protective or have different expectations of him when he's dressed as a girl.