Dawn, you worry to much! In the process of meeting a woman, you do not need to tell all about your lifestyle. You have no need to worry about her finding your lingerie drawer in the first few dates. Focus on her and show her the important things about you. Never mind about the crossdressing issue until such time you and she both feel that things will progress and maybe become a committed couple. It's a fine line between telling a woman early on and waiting to long. To long would be when she has fallen for the man in you and you have fallen for her to the point of committing to a long term relationship. Tell a woman on the first date or so could be foolish since she does not even know you yet.
Yes, I've gone through it. And never have I been dumped due to my crossdressing. As you get to know a woman, you learn how open-minded she is. How she feels about other lifestyles such as gays, lesbians and maybe even bondage and discipline. Have an idea how she will react long before you tell her about your private life...including crossdressing. Before I have ever told anyone, friends, both male and female, I had a very good idea how they would accept the fact that I am a CD. To be honest, the only person to ever shunned me and put me out of their life is a brainwashed religious fanatic older brother of mine. I have at least 7 female friends that know and enjoy a closer friendship and more trust in me for my trusting them in telling them. But this was not something I did without getting to know them quite well and sensing that they are not prudish, judgmental, homophobic, overly ruined by religious misguiding, and other things that I would not accept in a friend in the first place.
So go date, be a man, put your best foot forward and let them fall for a great guy that later you might share more personal things about yourself with them.
