One possibility is that the boy is in a bet with his friends during summer vacation. If he can pass as a girl for a whole day at the beach, he wins. So he dresses up as a girl, and throughout the day, he has various encounters, like getting hit on by boys who think he's a girl, which creates a lot of humorous situations.
One possible plot could be that the boy wants to enter a summer talent show that is only open to girls. So, he dresses as a girl to participate. He might face some challenges like trying to keep his identity a secret while making new friends among the girl contestants. In the end, he could either win the show with his amazing talent or get discovered but still be praised for his courage.
Well, it could be for a school play during summer. Maybe the story is about a boy who has to disguise as a girl to get into a place only girls are allowed in the summer setting, like a girls - only summer camp, in order to find something important or to help a friend.
He could feel embarrassed. After all, in most societies, boys are expected to dress in a certain way, and being made to wear girl's clothes goes against that norm.
He might feel confused at first. Since society has certain norms about boys' and girls' clothing, wearing girl's clothes goes against what he may have been taught or seen so far. For example, if he goes to school and his peers make fun of him, it could lead to negative feelings.
Once there was a teen boy named Tom. For a school play, he was chosen to play the role of a girl. At first, he was a bit hesitant. But as he started getting into the character, he had a great time. He put on a dress, a wig, and even learned to walk and talk in a more feminine way. When the play finally happened, his performance was so convincing that many in the audience were really impressed.
Once upon a Halloween, there was a little boy named Tim. He was always fascinated by the beautiful costumes the girls got to wear on Halloween. So, this year, he decided to dress as a girl. He put on a long pink princess dress, a sparkly tiara, and carried a magic wand. When he went out trick - or - treating, some of his friends were really surprised at first. But soon, they all thought it was really cool. Tim had a great time getting lots of candies and showing off his unique costume.
Once there was a boy named Tom. For a school play, he was dressed as a girl. He had to wear a long pink dress and a curly wig. At first, he felt really strange and shy. But as he started to rehearse, he got into the role. When the play was on, he surprised everyone with his great performance as a girl. He even learned how to walk and talk in a more 'girly' way.
Once upon a Halloween, there was a little boy named Tom. He was really excited about Halloween. His sister had a beautiful princess costume that she couldn't wear this year. Tom decided to dress up as a girl for Halloween. He put on the princess dress, a sparkly tiara, and even some pink lipstick. When he went out trick - or - treating, all the neighbors were surprised at first, but then they thought it was really cute. Tom had a great time getting candies and showing off his unique costume.
One reason could be for fun. Maybe the mother just wanted to have a laugh and see her son in a different look for a short while. For example, during a family photo shoot or a small family party at home.