Like so many others here I have a couple of struggles. One is the difficulty in ending a dressing session, you know, recognizing you have spent an hour longer than you planned but there is always one more outfit or dress to try on. The second is the difficulty in coming out to those around you, family and friends. While I've come out to many in the family and have been outed to a couple others (who seem to be handling it with respect for me), I still haven't come out to my oldest friends. I'm retired so work is not an issue and I don't belong to a faith community of any sort. There are family members who don't know (or shouldn't know), but so far everyone has been supportive. It's grandkids who seem to be among the last to deal with, but that's the parents responsibility, not mine.
That coming out to friends is still more difficult than changing back to guy mode. When I'm en femme I feel confident that I could do whatever I want, go where I will, but that will eventually require letting some key people in my life know I'm Transgender. I'm starting to think that one of these days it will be easier to come out and to change modes. I'm not sure where I'm at in regards to that tipping point, but it is something I'm thinking about more now than in the past. I'm not sure what the things are that weigh on either side, but comfort with my femininity is beginning to exert more pressure on that side of the scale every time I dress.
I suppose there should be several other factors to consider but these seem to be the balance point for now. What am I missing?