Conflicting needs for a closeted MtF - help!

So, new problem. My husband (MtF, still IDs as male) is not out to anyone but me and one friend who is trans. He came out to me 18 years ago. Three weeks ago he announced to me he wanted to get an orchiectomy and start HRT (in that order), but didn't want to come out publicly (extended family, social and work) until and unless his changes begin to become too obvious to hide. He works for a school district where the leadership is pretty open and accepting, but there are enough conservative parents around to cause a massive stink and make things very uncomfortable for both the district and for him/us. It could threaten his job, and I'm currently self-employed and my business is not yet pulling a profit for us to live off of.

For the past few years he's been doing quiet things, easily hidden/overlooked, like shaving his legs, shaved his moustache (which he had since before I knew him), grew his hair long, began real "hair care routines" and such. It's been gradual, and it all came off as masculine or was easily hidden.

Since announcing his intentions in December, and once he knew he had at least some support from me, he has sped up the little things, so excited to embrace the female him, even though his first appointment to see a doctor isn't until July. He painted his nails (in a color that matches his natural nail color), is using a lipstick that matches his lip color, is using cover-up over a couple of discolored spots on his neck that bother him. Then he shaved his (nearly furry) arms. We also went together to get our hair cut. The plan was to just cover his gray, and get his split ends trimmed. Instead the stylist decided to get fancy, and he deferred to the stylist's professional opinion and he walked out with frosted, blended hair color.

He says he's still not ready to come out, but the combination may have tipped the scale already, and for anyone who is sensitive to the use of subtle makeup and such, he's becoming a walking billboard for outing himself unintentionally.

I did warn him this morning that he is dangerously close to crossing the line for his public appearance that is still important to him, and that he's going to have to be careful.

He's at that point that he's terribly excited to try all the things he has been denying himself for so many years, and the combination of finally having a doctor's appointment (in July!) and starting counseling tomorrow, plus my giving him "permission" to do these things by stuff like getting our hair done together (I also helped him pick out the nail polish and purchased some panties for him), it's ignited that drive.

How do I help him through his need to take these steps, yet at the same time help him with his other need to keep it hidden from the public? He seemed so hurt when I warned him that he was becoming visibly trans in his grooming habits. I didn't want to do that, but I also don't want him hurt even more deeply by becoming publicly outed before he's ready.

 

This morning when I saw him dressed for work, I was struck by how much the little changes have added up. I think some of his co-workers may already suspect after the hair thing, but I'm not sure.

 

It's a problem with his job. Our living is on the line. People freak out when children are involved.

---------- Post added 9th Jan 2017 at 02:47 PM ----------

This is at a district where I attended a meeting where there were several dozen angry parents who were freaked out because there was a FtM student allowed to dress male, and because there was a second grade genderfluid child being allowed to dress femme in class. Two of the school board members were actually voted off and replaced with new board members because they refused to "act" to protect the other children in the district.

I walked out of that meeting shaking mad.

 

We already have plans for when he's ready to come out. We know the law pretty well, which is very protective in our very liberal state. However, that doesn't help his psyche if he ends up out before he's mentally ready. Which is not likely to be in 2017, at this point.

 

School bus driver. And "he" is still proper at this time.