I took the same route, Stephanie. It’s a common enough story, especially for us older ladies. And yes, I share your sympathy with those who are trans and should transition but feel trapped by their circumstances. One can only hope those women come to terms with who they are and find the strength to transition, despite the difficulties. Because, as you’ll agree, I’m sure, it’s a life-changing thing.
However when it comes to cisgender crossdressing men, as opposed to closeted trans women, I find I have very little in common with them. 🤷🏻♀️
As for you wondering if cross dressing will be obsolete in fifty years. Not a chance. It might be perhaps a little more acceptable but I wouldn’t bet on it. The gender binary will not disappear in the next half a century. Simple as that. It’s the most fundamental aspect of all human societies. Too much of our world relies on it as a foundation. And us trans people are only chipping away at the edges. Even feminism with the benefit of a century and weight of numbers hasn’t been able to substantively dismantle gender roles.