Quote Originally Posted by ReineD View Post
I just thought about something else. You look great in your avatar and my SO looks great too. But, (I'm not sure how to say this delicately), not every person who learns to put on makeup, has a great wig, and has impeccable taste in clothing will be able to blend-in to the same degree. Some people have stronger male gender cues in their physiognomy and their appearance won't be as coherent. Sadly, these people might experience more bias than others.
I agree how well you blend in can make a difference and so does how overt your masculine traits that cannot be disguised or hidden. I tend to use the 80/20 rule or a variation of it a lot, and it seems to work in most cases. Out of 100 cross dressers, 10 are going to present and blend in extremely well, 10 are going to be very obviously male and would not pass at 100 feet (might as well have a flashing neon sign) and 80 are going to be somewhere in between. It is the 10 who are obvious that stand a greater probability of having a bad experience due to the behavior of others. The 80 will be fine except if they draw undue attention to themselves by inappropriate dress or behavior. It is usually a challenge when taking out new girls since they tend to way over dress even when you tell them not to. I dress to blend in which also helps not to draw attention to myself. I know I get read, but as long as your presentation is within general standards, most people will leave you alone or at worse stare a little longer than normal. And you can't forget that is not only about the way you look, it is also secondary factors such as body language and mannerisms. Those will get you read as fast or faster than your appearance in some cases.

If you are venturing out for the first time, I would recommend not doing it alone. Find someone with some experience, go with them, and learn from them. It will also make it easier and you will probably feel safer.