It sounds like a great situation to come out in, so I'd say when you feel comfortable, talk to your boss about it. I've got a great workplace and I've tried to talk to my boss about it, but it seems like we just can't get a good chance for me to properly explain things to him. I think he expects I don't want to come out until I can play the part, so to speak, but that's certainly not the case. I'd much rather my proper name and pronouns were used, even if I look bad. I'm not worried about any of my coworkers treating me poorly for not passing and I don't want to keep playing this role until I have enough money for real transition stuffs, cause that could be years away.
How do you feel about your coworkers and passing? How do you feel about being recognized as being a man, specifically in the context of where you're at in your transition now or where you'll be later?