There was a long lag there.
Lately the title of this post is exactly what I have been doing. For a while I was experimenting, oscillating. I would wear woman's undergarments to work for a week then switch back to boxers. Damn that was foolish! Imagine the stress of both a new job and trying to test yourself out in this manner, seeing what changing clothing would do for you. I was not in a happy state.
Recently I have begun to try something else and that is rock some androgyny. Since I am an analyst and spend most of my day in a lab I get to dress business casual and the concentration is on safety. Now that warmer weather has started I have begun to wear polo shirts and woman's jeans to work. Boot cut woman's jeans. I get to know but they are ambiguous enough to leave most in the dark. This last Friday I was entirely clothed in woman's garments (well aside from shoes and socks >_>). I had a brown pair of pants, a black woman's tee as an undershirt to a black woman's polo shirt. No-one comments no-one sneers, snickers, or insults me in anyway. I am also lucky that they can't! My company has adopted policies that forbade discrimination based on gender expression/identity and have done so ahead of time: it is still legal in my state of residency to fire someone for being transgendered. I am really lucky in this...
Anyway wearing all woman's clothing was an experience that, well I'm not quite sure how to articulate it. I guess the thing that makes the most sense is I felt more. I was exhilarated to be at work and performed with an energy I had not known since I had opened to metaphorical Pandora's box months ago. I found myself more confident to interact with co-workers and even asked one of them if she had gotten new shoes. She had by the way, navy blue flats with a black buckle on them. I really like her sense of style. She dresses up a bit more than most of the other woman in my department but does it just enough to look well put together and not out of place among peers.
I also took what I think is a pretty large step towards integrating transgenderism into my workplace. I am now a member of my company's chapter or P.R.I.D.E. I was hemming and hawing about going but heck, I had been wearing panties and 'woman's' jeans to work for nearly a week before the meeting I freaking belong there! :P
Anyway it was a good thing. I did not come out or anything rather it served as a way for me to find out that it could be okay. And also to begin to find people who could become allies, people for when I am having a bad day I can email and go out to lunch with and really tell them why. One such person is the chapter director, her story of how she became involved with the group nearly floored me. She's a straight cis ally who was asked to help out with an information table when P.R.I.D.E. was in its infancy operating under the name The Gay and Lesbian Professional Network. She had been involved with activity planning for the company for a while but at first was taken aback because she was not gay. But then she began researching and was absolutely captivated and ended up not only helping but running the booth. As she was a woman approached her and commented, "I have real respect for your group, I have a bunch of friends like you!" Now instead of correcting her, telling her she was not a lesbian instead she answered simply with, "Thank you!" because she got it, she understood that it makes no difference and it doesn't matter that the mistake was made, people are people regardless of orientation or gender identity.
She also mentioned how she got to see the work and the progression of PRIDE to make the company adapt policies against discrimination of transgendered employees and get that 100 rating from the Human Rights Campaign. She provided the blunt example that if tomorrow she went to her boss and told him she preferred male pronouns, he'd have a meeting with her department and then that would be that and any mix ups would technically be a reportable policy infraction.
I also learned from another speaker that they are currently working for benefit parody for transgendered employees. That means that if a person is going to get SRS the company would consider it a non-cosmetic medical treatment and it would be covered by their company health plan. I left the meeting feeling uplifted, as if the universe itself had given me a hug.