How can a crossdressing son truly please his mom and dad in such stories?

By being respectful. Simple things like using polite language, listening when they talk, and not interrupting can please them. For example, when his dad is giving advice, the son just listens attentively instead of being rude.

One story could be that the son crossdresses for a school play. He puts on a dress and plays the role of a princess. His mom and dad are initially surprised but then they see how confident and happy he is on stage. They are proud of his acting skills and his ability to step out of his comfort zone, which pleases them.

Maybe the son cooks a delicious meal for his parents. He spends the whole day preparing their favorite dishes. When his mom and dad come home and see the table full of food, they are overjoyed. This act of kindness and thoughtfulness pleases them a great deal.

One story could be that the son gets good grades in school. His parents have always emphasized the importance of education. When they see his excellent report card, they are overjoyed. The son also helps with household chores like washing the dishes and mowing the lawn without being asked. This shows his consideration for his parents' hard work, and it really pleases them.

Mom and dad might start by showing him examples of kindness and consideration. They could explain the importance of understanding others' feelings and responding appropriately.

They can sit together on a couch, smiling, to create a warm family scene for the son's story.

Mostly, this kind of behavior can cause confusion for the child in terms of gender identity. In a healthy family environment, parents usually guide their children to understand and accept their own gender in a normal way. So positive stories in the context of'mom crossdressing son' are scarce.

In general, we should focus on positive family interactions such as parents supporting their children's hobbies, education, and personal growth, rather than on such rather abnormal or inappropriate scenarios.

One story could be that in a small community theater production, a mom and son were both part of the cast. The son was supposed to play a female role, and the mom helped him with all the cross - dressing details, from choosing the dress to doing the makeup. It was a great bonding experience for them as they practiced lines together and got into character. Through this, the son also learned about different ways of expressing oneself and the mom got to see her son's acting talent shine in a new way.

There was a mom who loved dressing up for Halloween. One year, she thought it would be hilarious if her son joined in on the fun in a crossdressing way. She found an old princess costume she had made years ago. She gently persuaded her son to wear it. The son agreed after some coaxing. They went out trick - or - treating together, and the son got a lot of compliments on his unique 'costume', which made the whole experience very enjoyable for both of them.