Thanks for the tips nicole :) yeah, I think if I do decide to get it straightened I will go for a chemical relaxer, I'm also considering changing the color for the first time, hair is really the one femme thing I really haven't experiemented with yet. When I first started wearing my mom's clothes and buying bras and panties as a young teen (before I could drive) I never had a chance to even get a wig. Then for the past couple years I've cut it every morning after I shave to the lowest setting my clippers had, so growing it out is completely new and kind of fun. My office doesn't have any real rules on male hair length (checked the dress code) but I'll probably have to be just about ready to come out before I can get it chemically relaxed. (I do have quite a while before it'll be long enough for that) In the meantime I'm actually considering getting a wig so I can try to put together a more complete femme look.
As for getting smaller, I was just planning on doing a ton of cardio and a strict low calorie diet without any heavy lifting (all the stuff I used to make fun of guys who did, ha, how I've changed lol)