One possible reason is for the sake of a performance, like in a theater production or a school play where there is a lack of female actors or participants. So, male individuals are forced to take on female roles which require dressing like a woman.
In some traditional theater troupes, there have been instances where male actors were forced to dress as women. For example, in some forms of Chinese opera. These actors had to learn all the nuances of female behavior, from the way they walked to how they gestured. They were initially pushed into this by the requirements of the art form, but over time, they mastered it and became highly respected for their ability to portray female characters so vividly.
One story could be about a young boy in a school play who was forced to dress like a woman because there were not enough girls to play all the female roles. He was initially reluctant but as he got into character, he discovered a new side of himself and actually had a great time on stage.
One reason could be for comedic effect. In many comedies, having a male character dress as a woman can create a lot of humorous situations. For example, in some slapstick comedies, a clumsy male character dressing as a woman and getting into all sorts of silly situations.
One story could be that the wife wanted her husband to experience what it's like to be a woman for a day. She made him wear a dress and high heels for a family - themed costume party. At first, the husband was reluctant, but then he found it to be a fun and eye - opening experience as he walked in those shoes and got a taste of the challenges women face in terms of clothing and movement.
Well, I once heard of a guy. His wife was really into fashion and thought it would be a fun idea for him to experience dressing as a woman. So she made him wear a dress for a costume party at home. At first, he was really reluctant, but then he found it quite liberating when he saw how happy it made his wife.
In some cases, it could be related to a performance or a skit for an internal company event. However, forcing someone to do it without their consent is still wrong. For instance, if the company was preparing for a talent show and some overzealous coworkers thought this would be a great act and pushed the man into dressing as a woman without considering his feelings.
He could firmly and clearly state his discomfort and refusal. He has the right to say 'no' and demand respect for his personal boundaries. For example, he can say something like 'I'm not comfortable with this, and it's inappropriate for the workplace'.
One story could be about a boy who had to dress as a girl for a school play. His initial reluctance turned into an interesting experience as he got into the character and learned about different perspectives. He realized that clothing doesn't define one's identity completely and that it was just a form of expression for the role he was playing.
It could be due to a misunderstanding of local customs. Ash travels to many different places. In some fanfictions, he could end up in a village or town where the local laws or traditions demand that he wears a dress for a specific reason. For example, he might be mistaken for someone else who is required to wear a dress as a form of punishment or celebration.