So yeah... I work with cool guys with super mild MRA leanings... when you're a guy they're a decent bunch and I'm even close to the younger one who chats films with me sometimes and we've leant each other DVDs but I'm not entirely sure how that dynamic will change once I flip that gender switch. Neither of them are dating or seem capable of maintaining a relationship with a woman outside of their family.

They're my crew. We edit the same show in a tiny room together. It's, for lack of a better word, intimate, but they are clueless about gender identity and they've joked in a slightly intolerant way in the past. I'm considering the best possible way to make this reveal less stressful for them. Do you think I should bring them into the fold before I go to HR? Do I owe them that? Should I not show up in makeup and a dress (not that I would at this job) the first day they find out? It's a strange situation because I feel like they're going to be embarrassed by the things they've said to me under the umbrella of "locker room" talk unless I handle this right.

I'm in my third month of HRT, and I can feel the clock ticking. Probably by Spring I'll want to have a plan together but that's assuming I last that long in stealth mode.

Advice, ladies?

Other's probably have better suggestions, this was my first thought. Depending, of course, on how slowly you want to come out at work.

I would start by calmly. quietly disagreeing and counter-pointing when they do their 'men will be men' dismissive (to put it mildly) comments. At some point there will be an opening to speak up. That's your moment. I, personally, would not spring it on them if you want to keep a healthy working relationship. Things will change, how badly it goes depends on the dynamics of coming out.

Just my thoughts

I think Faith has the right idea.

Just springing it on someone is abrupt and can sometimes confuse and anger them.

Gently nudging towards the big reveal is probably a better tactic. Whenever they start making insensitive jokes, it might be time to tell them that the joke is in poor taste, or insensitive, or something. Tell them that you've never really enjoyed all this 'locker room talk' (... like that makes it better?) and that it seems a little unprofessional.

If one of them is more open to this sort of thing than the others, I would also recommend telling them first (if they are trustworthy enough). That way when you tell everyone else, you'll at least have a buddy to support you.

While I agree in principle with the idea of waiting until a relevant moment comes up in conversation, you mentioned that the calendar is ticking.  You may have to be the one to generate that relevant moment.

Regarding the timing of presenting, I would definitely tell them first, while in male mode, and then follow up with presenting as female.  Of course, in the workplace, the actual timing should be coordinated with HR.  The most common way seems to be to come out to HR first, then, with their assistance and/or coordinateion, come out to co-workers.

Don't worry about embarassing them.  Tell them in a respectful way in a location where you are not likely to be eavesdropped on.  After that, their reaction is their business.  You can't control other people's reactions.

Hi Elle's,

  Oh my.  Awkward.  Small group dynamics.  But you're the one who knows them.  And I suspect that most of them (as "cool" and maybe socially awkward with women) will end up being ok with someone who is seen to be "sure of themselves".  I mean there will be a weird period of adjustment, but ultimately they will settle back into the "usual" routine.

  So how to start a change in dynamics?  I might start by casually asking slightly edgy things, like "hey, did any of you ever wear your sister's panties?".  I suspect that in a group of 5 guys, 2 probably did.  And liked it.

  Then, if someone owes up, you can say something like "you know its weird, but I still do that sometimes when I go to bed.  You know, its sort of fun?) 

  Well, once a discussion of wearing the other gender's clothing has started, you can lead the discussion where you will with subtle comments.

  Don't know if this approach would work for you or not, but its a suggestion.

      Carolina   

  And another thought.  If you wanted to try this approach, you could say that a college student was doing a poll and asked you about stuff in a coffee shop or someplace.  And one of the questions was the "did you ever wear" thing.  And you had.  Did anyone else?  If you get a "me too" response, you can edge forward.

    Carolina