Interesting question. So I will list my experiences, briefly and the outcomes.
1) came out to my soon to be wife as a (limited) cross dresser, acknowledging a predilection towards women’s underwear and stockings. At the time she expressed tolerance for that much, but warned that she could not accept it if I chose to dress fully as a woman. Long story short, I eventually felt compelled to do just that and asked her to accept it. She didn’t and we divorced about three years later.
2) Subsequent to that I was still closeted to people that knew me, but did get out regularly en femme. Early one evening as I was doing laundry, I got a text from a co-worker who asked what I was up to. I impulsively added “the usual stuff, shirts, pants, stockings and panties”. At first she LOL’d as if it was a joke, and I might have left it at that, but I instead said, no, seriously. A long conversation ensued. She was highly supportive and still is. She shared the secret with her husband and best girlfriend, also a colleague. And over time we had dinner and drinks together at my place, at local eateries and her home. As it turned out, this was one of the better outcomes.
3) Subsequently, I came out to my PCP (also a colleague) and her lead nurse practitioner. Both worked with transgender patients in our clinic. Both were and remain immensely supportive.
4) I suppose buoyed by the good results, I came out to one other NP in our group. She was also supportive, and soon invited me out for drinks and other things that we should leave to the imagination. Within days she had shared the experience with other colleagues and I was quicly outed to most of the staff. She meant no malice. I just didn’t consider how prone she was to talking. In retrospect, no harm was done and I rather enjoy being out to my supportive colleagues (I’m retired now) and could care less about those who are not supportive.
I forgot to include a few other ‘coming out’ experiences with former colleagues that occurred around the time I began coming out completely to my ex. Those three experiences were totally positive and the people involved remain both friends and supporters.
