He may feel a bit self - conscious at first. Wearing girl's clothes is not the norm for him. However, if his sister is positive and supportive during the process, he could gradually feel more at ease. He might also feel a sense of creativity being unleashed as he participates in this unique activity. And depending on the reactions he gets from others (if any), he could either feel more confident or a bit shy about his new appearance.
Maybe the boy is just curious about how it feels to be a girl. He might want to experience what girls do, like wearing dresses and having different hairstyles.
It could be that they are playing a game. For example, they might be acting out a story where the boy has to disguise as a girl for some plot - like sneaking into a girls - only event in their make - believe world. And his sister is helping him with the transformation by dressing him up.
She might be doing it for a play or a performance. Maybe they were planning to put on a show for their family or friends and this was part of the act. Another possibility is that she was simply curious to see how he would look like as a girl.
One reason could be curiosity. The boy might be curious about what it's like to be a girl, how different clothes feel, and how people would react. Another reason could be to help his sister out. Maybe his sister was supposed to be in a play or an event and couldn't make it, so he stepped in. Also, it could be for fun. He might just want to do something different and have a laugh by pretending to be his sister.
There were a few novels about poor boys letting girls go that could be recommended. Among them were Night Breeze Ripple, Heart Blade, and The Doted Wife 101. These novels all involved the love story between a poor boy and a girl. Some of them even included the gap and conflict between a rich girl and a poor boy. These novels described the plot of the male protagonist letting the girl go, giving the readers a special touching and emotional experience.
One reason could be for fun. Sisters might find it really amusing to see their brothers in a different, unexpected look. Another reason could be her creativity. She wants to experiment with different looks and her brother is an easy model to start with. Also, it could be for a joke or to create a funny memory that they can look back on and laugh about later.
There was a boy called Jack. One day, for a school play, he had to dress up as a girl. His mother helped him. They chose a beautiful blue dress with lace. Jack also wore a wig of long blond hair. As he got dressed, he was a bit nervous. But when he walked on the stage as a girl character, he got into the role. He even learned to walk and talk in a more 'girly' way for the performance. It was a really interesting experience for him.
Perhaps he was initially resistant but then went along with it, seeing it as a chance to play with his sister. He could have started laughing and having fun once he got into the spirit of the game.
Once upon a time, there was a little boy named Tom. His sister was a very creative girl. One day, she decided to dress him up like a girl. She put a pink dress on him, added a cute bow in his hair, and some shiny bracelets on his wrists. Tom at first was a bit reluctant, but then he started to have fun with it and they took pictures together which became a very funny memory for their family.