There are very few people who know of my crossdressing. My wife, and a close friend who was a female impersonator years ago are the only ones I have told. I have a female friend that I have known all my life (lets just say it's over 45 years!). I guess an important bit of information to add is that she's gay. I am going on a vacation with her, her brother (who is also a lifelong friend), and his 13 yr old son. She and I are leaving a day in advance of her brother and his son, due to flight availability (I just hate to have to spend an extra day on a tropical island...darn airlines! lol).
I really want to let her in on my secret, but I'm not sure how to even approach the issue. I know she will be OK with it, I just don't know how to start the conversation. Do I just blurt out "I wear women's clothes"? Maybe I could just appear the first night in my bright pink Looney Tunes pajamas and say "guess what"?
I now understand how difficult it was for her to tell me she was gay so many years ago. I do not want to reveal it to her brother, just her. Her brother and I drifted apart for a while, but are now reconnecting due to a common interest his son and I share...scuba diving. The trip we are going on is a dive trip, and will be their first.
I will have time to tell her the first night, before the others arrive. Any suggestions would be appreciated to help me approach a conversation that will be difficult for me.