Lucky for me I told my wife about 25 years ago. While the first month was pretty rocky as my wife slowly began to understand what being Transgendered meant, things began to smooth out. To this day, she is my closest Allie when it comes to what to wear and how to look.
Getting outed at work was quite unlikely. I was out shopping one day downtown. As I walked down the sidewalk four of my staff walked right into me. I thought at the time that if they recognized me I would be totally screwed. Lucky for me none of them recognized me and one even excused himself as he brushed against me.
While it wouldn’t have been the end of the world as we are pretty well protected here in Ontario under the Ontario Human Rights and Gender Identity. As a Professional Mechanical Engineer, it may have limited some opportunities. However, having significant value to the company, I was never fearful of being fired.
I consider myself exceptionally lucky because in the 25+ years, I have been out in public, my male persona has never been discovered. Considering I am a public speaker regarding Transgender issues at numerous Colleges and Universities. My transition between male and female is so drastic I never have worried about being read. While I considered the possibility of being read as a male my real identity was pretty much safe.
I believe every situation is different. If you are lucky enough to pass very well you are likely very safe. If you look like a male in women’s clothing you would likely have to be considerably more cautious and decide if getting caught was worth the chance.