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GG
You asked for honesty, so I'll give you my observations based on having gone out for years with my SO dressed. These are also her observations.
First I want to say how attractive you are. You really are, you know. 
Now for the rest. There are very few CDers who can be mistaken as genetic women in real life. It might be possible if they are young, small-statured, and possibly Asian, but it is rare for the rest of you and it has little to do with the clothes, jewelry, wig, or makeup, providing these things aren't off the wall which in your case they are not (other than maybe find a wig that suits you better, and work more with your eyebrows). There are several key reasons for being read, among them are the differences between male and female general body sizes and facial physiognomies. Male necks, shoulders, hands and feet are generally larger than women's even if both are the same height. Also the distances between a multitude of key points on the face are different for men and women (lip and nose, eyelid to eyebrow, mouth width, nose width, placement and shape of cheekbones, facial width, jaw lines, brow ridges, profile thickness, to name a few). This is why transsexuals who wish to be stealth get Facial Feminization Surgery.
All these things are apparent to the keen observer. But here's the thing: not everyone is a keen observer. Most people are too preoccupied with their own affairs to notice subtle, conflicting gender cues. To them, the more apparent cues are sufficient to not raise red flags, such as a wig, makeup, breasts, and appropriate clothing. Still, some people are better than others at reading even the subtle gender cues like the older lady you encountered, and they will read you right away.
Also, the minute you interact with someone for any length of time, they'll know that you are not a genetic woman, even if they hadn't figured this out before hand for lack of keen observation. When we talk to people we go through a multitude of facial expression changes, our heads tilt and they see us at several different angles, and also the voice is a pretty big giveaway.
As my SO went out more and more into the mainstream, she went through a phase, like you, of coming to terms with the fact that when she interacts with people, they know. But, she also discovered that when she speaks to people, her personality and general likeability shine through, and people (if they are not die-hard homophobes) generally are willing to respect her and like her for who she is. They do not reject her appearance.
So there has been a shift in my SO. In the beginning she was rather terrified of being judged as a man who wears a dress. She does pass well enough not to be read by most people that she does not directly interact with. But at the same time she no longer sits quietly in the shadows and she orders food, pays for stuff, engages in conversations with the people around her, and I believe she is now OK with the idea that people are OK with knowing that she is not a genetic woman, or at least they are polite enough to keep their opinions to themselves. Also, we've found that generally women are more open minded than men. My SO can still go out and be herself and she is not quite so loath to being read now, although she is still cautious of her surroundings. For example, we don't spend time in family restaurants where there are tons of kids or at malls on Saturdays that are filled with teenagers.
I hope that I haven't said anything to make you feel sad. I'm just trying to give you the benefit of my and my SO's personal experience. My SO goes out regularly, on average a few times per week.
Last edited by ReineD; 06-30-2012 at 05:37 PM.
Reine 
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