My employer has a pretty good EEO policy and guideline for transgender workers
http://www.opm.gov/policy-data-oversight/diversity-and-inclusion/reference-materials/gender-identity-guidance/

My boss is great, open, and recently increased in rank (that's civilian rank ). We're getting a new boss soon and my current boss will be my boss' boss. I work one-on-one with him sometimes and I'm even going on work travel with him soon. The new boss gets announced sometime near Christmas.

I'm interested in coming out to my current boss soon so he knows the situation and can help prepare the new manager. I also want him to know because I feel as though people are questioning me and wondering what I'm going through and he may be able to help with that. I do trust him well.

Is it important to contact HR first? (we have an EEO/Diversity office that mainly deals with complaints)

Does timing matter? ~ I really don't know what I'm getting into regardless of when I do it, and sooner will let me prepare for the full time coming-out better, which is 6-18 months away. That depends on how HRT goes, how socially prepared I am, and how long before I go insane (I'm very queer-closet claustrophobic and it's affecting me).

I think telling the boss you have now and are on good footing with is probably a good idea.The more allies close to home, the better.

I will definitely be telling my boss soon...

I'm on travel with him (after a terrible trip - we arrived 7 hours after originally scheduled). OMG was today weird... and not (just) because I'm with my boss.

Firstly... TONS of people were looking at me funnily. Lots talked to me randomly (men and women)... so that vibe I give off has definitely changed. I like it. The weirdest was on the final flight - there were just two of us in the row... and the (older) woman was looking at me as we were descending (and it was dark). I could feel her eyes on me...... creepy... then I glanced in her direction and she very quickly looked away. Yeaaaah... like I didn't notice you watching me for minutes. . .

My presentation? Normal for me right now. Hair? Everyday. Face? Patchy with (by the end of the trip) decently long hair. Clothes? My most androgynous men's outfit (ok... the shoes were unisex Toms.com and the pants were women's jeans... but come on). My demeanor? Effing feminine

So that's where I was today. I was a woman on travel with her boss... and he didn't have a clue at the beginning of the trip.

My boss met me during TSA. I was being patted down. Apparently the gaff looks like a dense spot on the scanner... who knew ~ and I got to experience that twice, though the first time was the worst. The first time he patted me on the butt... and correctly gendered me to the explosives scanning person ("could you check her hands") - he corrected himself. My boss met up with me shortly after that... as I was putting on my lady's shoes (yeah... they're unisex, but I got the Women's ones... they're just a little more fem... and say W12 inside). I was also putting my computer, complete with sparkly dragonfly sticker (hey... my daughter gave it to me), in my bag.

We had a beer while waiting for the first flight (the one we'd actually get on, that is). I talked a bit... he knows my wife and I were having issues and I kind of said that I was the cause (though not the fault). He asked... and I said I'd have to tell him when we got home. If I get a chance while we're away I will talk...

So between that conversation, and me looking pretty girly and getting constant looks, and me peeing all the time (and taking a while doing it), and me acting pretty feminine (I really can't turn that off now... it's weird - once the wall came down... Tarah was released and can't be put back in)... I'd better tell him soon.

There's also the work situation - he needs to know. I hope there's a good time to tell him.

I have an update... I did come out to my boss successfully So far it's great ~ he's interested in learning more and getting himself and the new boss into a class or other training on transgender work issues. Any idea what resources are available for that?

I have my boss addicted to Susan's, it works out great.

I got the Kindle sample of The Complete Guide to Transgender in the Workplace by Vanessa Sheridan and didn't like it. I ordered Transgender Workplace Diversity by Jillian T. Weiss instead (also half the price). Hopefully it's good.

I think my boss realizes it will be difficult for me and my workplace, but he's supportive and wants to do the right thing.