aucoraborealis ... Your post really intrigues me ... And your pointed question "has anyone ever had a lifetime hiding their breasts?" is right on target for me. The answer is yes ... and no as I explained earlier.
Following are excerpts from our post, with my comments preceded with a double asterisk (**):
** Your first two "conditions" are nearly identical to what I went through:
1.We've always wanted two kids, so we wanted to be pregnant again before I start HRT. That's been taken care as of five weeks ago. [smiley face]
2.I can't live as a woman. I need to continue living as a guy and using male pronouns (even at home). Yikes.
I'll be taking HRT and getting my facial hair removed as time and money permit, but I'll be living my life as I always have: a guy. So it seems that I'm a circumstantial androgyne. I'm fine with this, but I have some concerns that I hope some of you could help me clear up.
** Same here. I had electrolysis as time and money permitted, but only on my chest and underarms.
1.I don't have to hide the evidence of my breasts at home, but I'll be hiding them in public every day for the rest of my life. Everyone says it's quite easy to hide them, but most of them are only doing it until they're ready to go full-time. Has anyone here experienced a life time of hiding their breasts? I have a feeling that might get really old after a few years.
** I'm not convinced that you'll feel the need to hide your breasts every day for the rest of your life. First of all, "hiding" does not mean binding or wearing a gynecomastia vest every day ... any loose fitting shirt does a pretty good job. As I said in my earlier post, you can become selective about when or even how much to hide them ... Plus it depends, of course, on how big the breasts are. Mine are C cup or D cup (depending on bra-brand), and some bras (like sports bras) naturally compress the breasts more than others that "shape". As I said, I've had my breasts for 30 years and I don't put much effort into hiding them ... Sometimes I get called "ma'am", but then they typically change to "sir". Who knows what they may be thinking. Who cares!
2.My other concern is being stuck in-between genders. I've always thought this would be awesome, but now that hormones are only a month away, I'm wondering if being stuck in the middle and always having to hide certain aspects of myself might bring on a whole new kind of dysphoria. Simple things like swimming, or wearing form fitting shirts, and, quite frankly, sex.
** I'm not sure what you mean by "stuck in the middle". You mention that your wife is on-board with the HRT, so that's all that matters. Some of the other posts give you some advice here, most basically say "don't worry about it" ... You've got to do what you know in your heart of hearts what you need to do.
3.What if I stop passing as a guy? How does society tend to treat you when it isn't sure where you sit on the gender scale? I'm 5'11, athletic build, and I have a masculine brow and nose, but aside from that I don't see too much stopping me from passing after a few years of hormones and electrolysis. I'd love to know if anyone else has gone through this. This is me:
https://drive.google.com/file/d/0BxdDME2mLagwNXNmOC1RaG1WOUU/edit?usp=sharing (I'm a stylized portrait photographer. My selfie's tend to be over the top haha)
** If you don't want to stop passing as a guy, you probably won't have that problem. I don't. You didn't mention it, but I assume you are NOT having the SRS surgery(?). I did have the SRS operation way back in 1986, and that led to some other subtle changes, such as losing the hair on my legs. It slowed my beard, but it still grows, needing to be shaved only about once per week though. I really don't think that passing as a guy is an issue.
** If you like, I could sent you a "selfie" as you call it, but I don't have a way to post one on a web site like you did. Perhaps the attachments option below would allow that, but I'll have to find a photo first.
Roberto