I wish I knew the right answer for this one. My experience has been that of one who prepared mentally and socially for the day when everyone would eventually find out I'm a crossdresser. I knew when I was 12 that I wanted to come out one day. I used to wear my mother's clothes and go for day trips to Boston to get used of being seen in drag. I used to tell girls I knew about myself cause I knew they would spread the word for me. "Please don't tell anyone" was the best way to manipulate them into outing me. I just think it feels real awkward to just go tell somebody I am different. It's easier to let everyone else gossip about it and then just admit it when confronted.
When I turned 30, I was ready to just come out and start wearing women's clothes in public all the time, not just on day trips. It's really nice to know that everyone knows now and I don't have to hide it. They don't like me any better, but now it's not a shock and it's expected of me. Now, when I meet people, I don't have to tell them. It's obvious. When I am not in drag for work, I can count on other people to expose me with simple gossip. I keep my nails painted, so that helps too when I'm not all dolled up. My boss makes me wear gloves while I am out delivering stuff though. I guess you can say that what bothers me the most is when someone doesn't know about me. They treat me like a normal guy and I find that distasteful.