Lexi IMHO your title tells the true. In my thoughts, the worse case of how bad it will be is no where close to the good of reality. Our minds have a way of talking ourselves out of doing things.
Lexi wrote: "what happens if I see someone I know"
I have run into people I know when out and about multiple times. Once literally face to face and one time passing right next to them. They looked at me and just kept walking and did not even look back. Yea I looked. IMHO if you have a decent feminine presentation with blending clothing they will not know it is you. Makeup and wigs do wonders at changing looks.
Lexi wrote: "what happens if I get odd looks/stares, etc...?"
Women get looked at get use to it. To help with the looks make sure you have a blending look unless you want to stick out and be looked at more.
Lexi wrote: The most irrational thought that has ever come to mind is the one where I am arrested for crossdressing, locked up in jail - key thrown away...
Most cops are reasonable. Unless you are doing something wild or against the law you should not have any issues. I have been stopped for speeding. I gave him my ID and registration as he asked for. When he ask "this is your ID" I said yes it was me. I still got the speeding ticket. No jail time.
Lexi wrote: Do the clothes I wear cause anxiety to others?

Do they know? Do they even care?
Anxiety I can not answer. Well yes I can, the clothes and my cding gave my ex lots of anxiety but a lot of things gave her anxiety that she refused to deal with as a couple. Other people in public i have are either seem ok with it or i am not with them long enough to tell.
Some realize I am a guy fairly quickly and do not seem to care, Some people when they realize I am a guy have the "pause" of reality adjustment, then slowly or suddenly seem to be ok with it. Others just are not sure what to think and just have a puzzled look. Might be interesting to be in their minds.
In my experience, the more our mind thinks about the worse that can happen, the worse our mind can make it. Reality is usually something completely different and better.
If people want to get out and about enfemme, I usually tell them to work up a blending, but not perfect look. If you want to know what is blending go scope out where you want to go and see what the GG's are wearing and wear similar. Where to go, I say go to a public place with a variety of people there. A mall or shopping at a store like wallymart, Kmart, Target, Kohls, or similar place is good. You do not need to by anything just look around like you are shopping. Pushing a shopping cart can make you feel safer and gives you something to hand on to. Go shopping for you general household stuff. Buy some TP, soap, shampoo, envelopes, or what ever.
I have been lucky, the worst that has ever happened to me was running into an older sales lady when shopping in male mode for femme clothes. She did not say any thing, just had the evil eye look at me the whole time I was in there. I just went and shopped some where else.
What is the worse that will happen, they will ask you to leave the store. Then leave with your head high and go shop at the next store that wants your money.
I have shopped some places enough they know me in either mode and treat me the same no matter which way I am presenting.
I could tell you lots of stories, but just go forth and have fun. The worst situations happen between your ears.
kimberlys cd
joe in a skirt