Hi Brooke,
Language is a reflection of culture and it's unfortunate how restrictive the gender binary is. For now we are usually stuck with this outdated concept of "pick one".
The only person who truly knows the answer is you. It's ok if your answer changes over time - mine certainly did - and you shouldn't let other people invent and impose irrelevant rules on you. If someone claims you are not transgender unless you pass as a woman I think they are wrong. How exactly is passing defined, and who owns that definition? We have all seen cis-gender individuals who don't perfectly fit the social definition of what gender is "supposed to" look like. The real answer comes from within - the way you feel.
It's rare, but a few governments in various locations are starting to understand the gender binary is outdated. Two states in the US now offer a third or undefined gender "X" for a driver license - also supported in parts of Canada. A few countries now legally allow a third-gender passport.
But in most cases you have to chose one of two options, and government forms need to follow a legally recognized gender marker that remains consistent (you only get one answer). Unless you have updated your legal ID there are times when you have to match your ID. But for things that are less formal and don't need to follow your ID, you should choose who you truly are.
Think about your future - do you want to start moving in that direction or stay where you are. You decide.
And to answer your question, yes. In the past, I definitely had the problem you're describing.
Kendra
