I have been dressing for about half a century, starting well before puberty. I have never felt like telling anyone who knows ‘him’ about ‘her’. For starters I would be too embarrassed that they now knew that about me. Whatever they said, however they acted, they would have additional knowledge that they had not known for all the time before. Unless they had a memory failure it is still, even these days, an unusual piece of information which is bound to have some impact whatever is said or thought. Furthermore, what benefit do they get from knowing? Perhaps they could appreciate that I trusted them enough to have confided in them but is there anything else? Do they now have to keep it to themselves? Can they share that knowledge with their partner, best friend, acquaintance, work colleague, another who also crossdresses? If none of the above then should I have asked, before divulging, if they should like to know something about me which only they can know and not let anyone else know? Are they now obliged to provide me with one of their innermost secrets? Do I in turn wish to know something like that about them, something that I in turn cannot divulge to another and must keep secret, even from my wife, for instance? In fact, before I tell anyone about my dressing should I clear it with my wife first? Would she be comfortable with others having such knowledge about us, having information that currently, as far as I am aware, only she knows?
It is so much simpler to not tell another soul and as I said, that is my starting position and always has been. There is always the possibility that I might get caught or otherwise inadvertently give myself away; although that has always been a possibility, however many precautions I take. My wife found out about me because I was careless. However, I have come across some who have deliberately confided in others and have positively relished doing so. They have not ‘come out’ but just shared themselves with one or two carefully selected close friends or colleagues and seemed to have found that liberating for them. It just scares me silly.
I am not the least ashamed of who I am or what I do or have ever done. I never consciously chose to crossdress. I tried not to but life got far more comfortable when I just accepted Linda was part of me, though I am no different. Linda has always been part of me and those who know me have also seen her in me. We are one and the same, just the presentation differs. On occasions Linda gets full control of the body which is attired, behaves and shows mannerisms as far as she can appropriate to her gender. Do I need to account for or explain this to anyone else when I don’t understand it myself? I don’t feel I am attempting to fool either myself or anyone else, I am just being me. While society has moved miles in my lifetime in these respects, dressing to be a woman as much as possible is still off mainstream. Does it say anything about me or those who I love or who love me? I don’t think so at all, but might it if I was to tell anyone else what is essentially purely personal to me?
So in answer to my title question, I think it is a firm “No” for me but I have no problem appreciating there are those for whom it is an equally firm “Yes”, though I’m certain they do so only after careful consideration of all the possible consequences for all concerned. That is way beyond me.