Val, I know where you are coming from. I used to be VERY self conscious about my self in male mode so forget about how I felt as Mary Ann! I won't sugar coat this (because I'm not Willy Wonka) but there are no easy answers to this. CDs are a very small minority which makes us "not normal" by most other people's standards. People react differently to things that are not normal. Some fear it, some shy away from it, some lash out as a defense mechanism to it, some embrace it. There is good and bad news about that... 1st the bad; you are NOT going to change how people react to you being dressed as a women. 2nd the good; you have the ability to change how you respond to their reaction. If it pleases you to go out in public dressed as a woman, then you will have to master how you respond to the looks etc. Remember, you are not out there to please them, only yourself.
It does take some time to be comfortable dressed in public. Think of it like learning to ride a bike.. start on a tricycle... go out in women's jeans. No big deal, 99.9% will not notice, but you know. Then you get your two wheeler with training wheels... Jeans and heels (go with a wedge, they don't make as much noise).. a little bit more of a big deal. Someone might notice, probably a GG who is admiring your shoes! Next take the training wheels off. Jeans, heels (not too big), clear polish on your nails and maybe some mascara. Still most (96%) won't know, but you will! See, you are getting comfortable doing what was very uncomfortable. You are expanding your comfort zone and you will begin to care less about what others think (it really doesn't matter any way) and feel better about you. Now lets take one hand off of the handlebars... You are gaining confidence. Same stuff as before but add makeup (not to bright), a wig and nail polish. Go some where with out too many people to get comfortable with yourself first. Then start venturing in to places with more and more people. As you get comfortable with your self you will act with more confidence and stand out less. Ok, it's time to ride that bike with no hands... A dress/skirt, pantyhose, heels that make noise, wig, makeup, nails, purse... the whole enchilada. Go somewhere to get comfortable with yourself first, then once you have accomplished that, you are ready for the real world now girl. (BTW... a vast majority of the people are so wrapped up in what they are doing that you are practically invisible)
Honey, you don't cook a bullfrog by throwing it into a pot of boiling water, you put it in a pot of cool water and turn up the heat little by little. Before you know it, he's cooked.
That's just my 2 cents... ok, probably 50 cents, but keep the change.