It would not surprise me to learn that the guiding force behind this boy cross dressing is his stepmom, Gabrielle Union. She is a known complainer and at times, a professional victim when she gets let go of some entertainment project. Gabriella seems to like the attention and drama of being hard to please.
You description of her is most accurate. She was on American’s Most Talented and she was so much to handle, they got rid of her after one year. Then she sued.
She is emasculating this boy because it is not her son. Her children with him are left alone.