Perhaps there was something wrong with the shorts, like a broken zipper or a tear. Mom noticed it and had the son take them off so she could either repair them or just get rid of them and find a new pair for her son.
This title seems inappropriate and rather concerning. It could potentially refer to a situation in a fictional or misconstrued story that involves a boundary - crossing behavior which is not acceptable in normal family or social ethics. But without more context, it's hard to be sure exactly what it implies.
He might have felt a bit embarrassed at first, especially if there were other people around.
This is completely unacceptable. In any society, there are boundaries to protect the well - being and appropriate relationships within a family. A title like this crosses those boundaries and can be considered a form of abuse or at least a very wrong message.
This is an extremely inappropriate and unethical topic. Such a situation is abnormal and goes against moral and social norms.
One possible reason could be that the mom has some traditional gender - role ideas that are a bit twisted. Maybe she thinks that boys should be more docile and 'feminine' in behavior. Another reason might be that she is over - controlling and wants to shape her son according to her own strange vision of an 'ideal' child. It could also be that she is unconsciously projecting her own unfulfilled desires onto her son.
One reason could be financial gain. Maybe the son wants more money for luxury items or to pay off debts and he thinks blackmailing his mom is an easy way to get it. For example, if he knows she has a secret savings account she doesn't want anyone to know about.
It could also be that the mom is trying to teach her son about gender fluidity or break gender stereotypes. By dressing him as a girl, she is showing that there are no strict rules about what boys and girls can wear. In some cases, it might be a form of art or creative expression within the family.
One reason could be to help him with a bad habit. For example, if the son bites his nails, the mom might hypnotize him to stop this behavior. Hypnosis can plant a subconscious suggestion to break the habit.
Another reason could be related to education. In some cases, moms might check as part of teaching their sons about basic body parts and hygiene. This can be an awkward but important part of growing up for a boy to understand how to take care of himself in that area.
Perhaps she was making a point about gender fluidity. In modern society, we are more aware of the concept that clothing doesn't have to be strictly based on gender, and she might be trying to teach her son this idea in a rather unique way.