It is an interesting question which asks another, at what point do you decide to tell some one?
From these forums there is a lot of discussion about the how’s and when. It seems the tipping point is when crossdressing is something that can no longer be hidden and to be able to express this part of the life you want to follow.
In this it’s not the who, but the consequences of that action. Will it throw you back in the closet or forward your crossdressing.
I will outline my decision. I decided to tell my mother. This took me a very long time to build up the courage until I did it. There was an acceptance which helped me to the next stage of dressing and becoming what is classed as having an acceptable appearance.
With the help of my mother we had the first of a couple of trips outside to open places. It was clear that I was advancing and wanted to take things further. Phase two was to tell my siblings. This went okay with one sister who wasn’t sure.
This led to more help. I was now out and about more but it was difficult in a relationship where I came out. Although it was accepted there were other circumstances where we realised it would be difficult for us. We parted as friends and she is still in touch and go out too.
After this I decided that I would not get into relationships unless I was honest from the start. I am still single and not in a relationship.
From there my friends, relatives, neighbours and some work colleagues were introduced.
Finally I retired and live my life 90% crossdressed. I applied for jobs and work as Angela. Now there are co workers and clients who know only Angela.
From telling my mother to now is over 30 years. Every step has been fraught with angst but it has been quite a journey and, apart from a few hitches, has been a success. At every stage I tried to assess how the person thought and how accepting they would be. There were no guarantees but I was lucky.
I had no real aspirations at the start, apart from enjoying wearing womens clothes . It evolved from there and acceptance has been a crucial part.