This can sometimes be difficult to tell for sure. To me, masculine and feminine tend to have to do more with outward appearance, while male and female has more to do with your inner sense of your gender. There are feminine men and masculine women, but they still identify as men and women respectively. So when asking myself that question, it would be something like “Do I want to look and act feminine today, or do I just feel like a woman?” And it could be both, of course! It can just sometimes be tricky to differentiate these feelings due to society’s conflation of these terms. If its too distressing, you don’t have to pinpoint exactly what your identity is. Some people just stick with the simplest of terms because sometimes its just not possible to tell, and therefore use terms such a Non-Binary or Genderqueer. 

As for your second question, that’s not something I have personal experience with, but I have read about other nonbinary people who have taken T. So in theory, the answer should be no, but I think it also depends on how enbyphobic your provider is. I’m lucky in that the place I am hoping to have a certain surgical procedure is pretty accepting of Nonbinary identities, but not everywhere is. So don’t be discouraged if it doesn’t work out the first time, there are many accepting medical providers out there!