I have always read with envy the coming out stories others have told and now I can finally share one of my own.
It started with the knowledge that the time my best friend and I will have in the same city (or country) will be coming to an end soon and after 25 years of friendship I felt I needed to share this part of myself with him.
I had previously told my wife (Prior to marriage), a marriage counsellor to help with our issues and a female friend who I felt confident would accept me and respect my confidence. So telling someone I am a crossdresser is not something that comes naturally (like it does to any of us, ok most of us).
My best friend and I made plans to see a 80's rock legend perform on a Friday night as a final boys night out. We planned on having a great night out with drinking and hard rock music and were staying at the hotel where the show was so no worries about driving or getting home late.
After the show we were drinking and talking and I said we should get some fresh air. Although I was feeling the effects of the alcohol it did not effect my decision making, only my ability to actually get the words out. I had been thinking about telling him for weeks and was pretty sure I would. As we went for a walk around the building I said that I had something to tell him and that it was pretty monumental to me and I hope he would understand. It went something like "I am technically considered a crossdresser". My big revelation was not as eloquent as I had wanted, but I said it and that was the important part. After all the deciding to tell him I should have spent a little bit of time planning what to say.
WIthout a moments hesitation, he thought that it was great and hugged me.
I have always thought it would not be an issue with him as he is into the Alternative Sciences including tarot cards, astrology, symbols etc. And in my books this makes him someone who is always willing to allow for more colour in your life than black and white and shades of grey.
As we talked more about my crossdressing into the night, he explained how he felt that the feminine and masculine are too separate and when they are combined into one entity that person is more "whole". It was late, we were drinking and a lot was said, so before I start trying to remember everything word for word I will leave it at, he was more than happy for me, thinks it makes sense for who I am and increases his respect for me.
His only problem was why it took so long. I explained that it had nothing to do with him but it had to be right for me.
At the end of the night and to this day I am very pleased that I made that decision, it went well and I feel so much better for telling him.