Hi Kate (and everyone),
Well, this is an interesting subject really. I think a lot of it has to do with the environment you live in. You live in a small town. Is it generally pretty accepting of LGBT or is it so small townspeople don't even know what that is? I personally think it is impossible for you to transition from the person you look like pre-transition to the person you want to look like post-transition without people knowing. Just some questions you may or may not get asked:
1) Why is your hair growing longer? Why does it look more feminine (or shorter for FTM)?
2) Have you been working out or something? You look like your pecs are getting bigger.
3) What's up with those red marks on your face? Did you burn yourself? Oh wow, this is the fifth time you've had those red marks, what's up?
4) Why are you wearing girls shoes, jeans, shirt, ponytail holder, etc., etc.?
5) When did you get your nails done? Is that pink nail polish or clear?
6) OMG, are your legs shaved? Are your arms trimmed? What's the deal with you always wearing long pants and shirts in the summertime? Why do you always cover up?
Then physical contact like a hug or a touch on the back:
1) Dude, is that a bra you are wearing under those clothes, WTF?
2) Wow, your arms feel smooth, skin feels smooth, hmmm!
3) Are you losing weight?
Deciding to wear other girls clothes they can't see:
1) Hey, I didn't want to say anything, but are you wearing girl's underwear? I saw you lean forward and I thought I saw that, what is going on?
2) Um, is that a girl's t shirt under that jacket?
3) Hey, those look like girl socks, what up?
Etc., etc., etc. I got asked a lot of these questions. I lived pretty androgynous for like the first year of my transition. I was not stealth. I didn't walk around advertising TS or anything. The way I did it was I came out to my friends and family, people I would eventually have to come out to. What's the point in avoiding the inevitable. If you are 100% DEFINITELY transitioning, if you are not turning back, why not let people know? You'll be coming out to them anyway. I think it's a very dangerous game to play with people you love/work with/friends, etc. to risk being outted without having a whole conversation prepared. I don't mean rehearsed, I just mean if someone says "What's up with this or that?" that you are prepared to come out and talk to them about it.
Like Jessica said, people will know. I thought I had everyone fooled. Once I came out, they KNEW what was going on. This was at the beginning stages of androgyny too, it's not like I was walking around in frilly tops or anything. This was post-laser, hair growing out, and wearing just basically girl jeans and loose tops and hoodies. I have always plucked my brows and been a little bit Metro, but still. It's pretty apparent to people that you are changing. Whatever changes you see in yourself (which are usually ZERO), people see tenfold in you.
So, transition in stealth, not if you plan on having a successful one; not if the goal is to not be recognized as who you were before. Granted for me, FFS made the difference, but if I wouldn't have had FFS planned, I would have come out even sooner, if that was even possible. I came out to family and like three friends before I was even on HRT. I knew what I was doing, I knew where I was going, I had to come out to make the discomfort of avoiding the truth be one less things to worry about.
I look back now at the decision and I have no regrets. People really respected the fact that I had individual discussions with them. They could ask me WHATEVER they wanted and I'd answer them honestly. I never got a question I couldn't answer because I already thought of the answers in my head. I used my blog here to document it all, good and bad. The difference between me and a lot of others is I transitioned with no kids; I had no one to think about other than myself. Sure, family and loved ones mattered, but it's different with kids, I know. I mean, I don't know what that is like because I don't have them, but it makes transition different.
Anyway, Kate, those are my thoughts. They probably echo many others and there are parts of what Lori said about thinking people don't notice that I could agree with too sometimes. You stated that you didn't understand why people would transition in stealth and I don't even think it's possible unless transitioning means physically just dressing different. My thoughts, Meghan