It seems that the earlier in life you share your crossdressing with others, the easier it should be. Without a long history that says you are just another guy, without a career or extensive family involvement it seems now that it would be simpler to broach the subject. I'm almost ready for Medicare now and it's difficult to place myself in that moment so many years back. As we age and keep this to ourselves we build a very large and complicated gender identity structure around our life. Each point of contact seems to be critical because that person has expectations and other contacts that create a potential for great loss. This would be particularly strong in the case of those with a career fearing potential damage. While that is resolved once we retire, the family has changed and now the kids we never told have children of their own. It becomes easier and easier to come up with excuses to stay hidden and in the closet as we grow older. I can't go back and change any of that history, but it would be nice to place it into perspective.
So, those who have told family and/or friends that you are a crossdresser, how old were you when you did that? Is this just my hangup or are there others out there who find it more and more difficult to share this as they age?