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.
Perhaps in the story, there is a magical or supernatural element. A spell or a curse has been cast on the boy which turns him into a girl - like appearance, so he is now dressed as a school girl until the spell can be broken.
Sure. There was a boy named Tom. For a school play, he was required to dress as a girl. He initially felt a bit awkward in the frilly dress and long wig. But as he got into character, he started to enjoy it. He noticed how differently people treated him when he looked like a girl. His friends were really amused and his performance in the play was great.
One reason could be for a performance like in a play or a show. Just like in the previous stories, when there is a need for a male actor to play a female role. Another reason might be for a prank or a joke among friends. Maybe they are making a funny video or something.