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'.
Perhaps it was part of a theater or performance art piece where they wanted to make a statement about gender roles. In this case, he might have been volunteered or forced into it to create a unique visual impact. It could also be that in a fictional story, it was a magical or supernatural force that made him wear the wedding dress for some comical or plot - driving purpose.
There were many cross-dressing novels such as Beautiful Land, Time Travel and Anti-Time Travel, Special Agent Concubine: The Black-bellied Prince Wants to Divorce Concubine, Flowers Are Not Flowers, Fog Are Not Fog, and so on. These novels were all time-travel stories of women cross-dressing as men. They told the story of the heroine using her intelligence to live in ancient times after she time-traveled to the modern world.
Perhaps he took it in good humor after the initial shock. He could have even started to play along, making jokes about his new 'look' and turning the situation into a more light - hearted one. For example, he might have started posing for pictures in a funny way, trying to make the best of the strange situation.
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.
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.