There is in this narrative, yet again the issue of bullying. Instead of his parents and family discovering his dressing up and allowing him to express himself and offering loving acceptance, they told him it was wrong and deviant.
The idea that trans is something inherent seems very often to be skewed by bullying. How can we tell if he would have taken a different path if his parents had been accepting? Perhaps he could have lived his whole life as a feminine man. The feminine tendencies might be inherent, but the path he’s taken was probably driven by that whole “forbidden fruit” narrative.
The other thing that struck me (as it does so often with these “coming out in middle age” stories) is the risibility of suggesting this person is oppressed. He’s lived life as a man. There’s a good chance he’s been promoted over better qualified/suited women to headteacher. Then when he is failing at that, he “comes out” and is feted, given a new job, told how brave he is, is the subject of newspaper articles etc.
There may have been some oppression when he was a child, and he may have felt part of him was stifled, but how many women live with that every single day of their lives, but don’t have all his advantages? I just find the whole celebratory tone about coming out quite sickening.