[Dianna1395]

Try googling transgender ( or crosscrossing ) support in your area. I found the one in my area was tied in with the local Aids support centre. You don't have to go dressed up, most would be willing to talk with you. ( I attended my support group for @ 6 weeks as ##:& before Jannet. I know you do not want to hear it but, wanting and trying to get breasts means that door is open, maybe just a crack, buts it's there.

As a side note, I had a mustache for most of my adult life, the wife wondered how I would look without it, I couldn't get it off fast enough. Slowly, I just removed my body hair too.

Good luck ..

Thank you Jannet for your thoughts on this. I have looked it up in the past, but that would be waaaaay too many people I would be exposed to. I am looking for more of a 1 to 1. The less people that know, the better I would feel about it. Okay, so perhaps I am a bit paranoid. It's just that where I live, even though it's pretty damn big, it always feels like everyone knows each other. The degrees of separation are not enough for me to feel comfortable.

Yeah, I know that door is cracked open just a bit, but that's what wedges and blockades are for, to help keep it from opening too much too quickly.

I too have had my facial hair for most of my adult life. Once, and only once did I sport a mustache, but I looked über creepy, so never did that again. Now most of the time it's the goatee, or every now and again when being lazy the beard. Once in a blue moon it all comes off just for a change of scenery and the Mrs. always gives me grief about it.

This sounds a little more... complex, then.
It might make sense to look for a professional domme to talk to, and trolling the "sissy" blogs might help, too. The idea being, find a lugubrious sissy-type or woman who has some "flexibility" in her outlook, and warmth towards the unusual.
It's NOT suggesting a sexual or "professional" encounter, though. Just a discussion with someone who could be trusted a bit, and provide some insight. Then from there, maybe a gay club on Drag night? Be the quiet guy in the background, say, and talk to the queens now and then, to get yourself some socialization. And then, plan and proceed as appropriate.

I'd think it's no different from going to a strip club to ogle the women. You won't be going home with them, but you might get to chat with them a bit, on a good night. And you could certainly bring the wife along for the spectacle, and to get her opinions and feelings afterwards (I.E., make her included and play to her feelings/needs for security and safety.)

-Dianna