It really is a catch-22 situation and its tough. I think about this all the time. "Is the amount of makeup I am wearing too much for what I am going out for?" and my answer is usually yes. The thing is, wearing less makeup is more natural and "blendable", but I also look less feminine. I rely on makeup to kind of mask as much as my masculinity as I can. There are a few outings I have had(with picture sets on my Flickr) where I went with a more subtle makeup look(less foundation/concealer, brown eyeliner, not much if any eye makeup on my lower lash line, lighter lip color), and I am not the biggest fan of those pictures, they make me cringe. I even stopped wearing my brown eyeliner because I didn't feel like it was feminizing my eyes enough and I would only see male in those pictures. I feel like I look better and more feminine when I am more heavy with my makeup, but at the same time, I may very well be overdone for simply going out to the mall or store. Yet, I think I prefer that to my lighter makeup looks, just because I would rather look overdone and more feminine than more appropriate and more masculine. I think I need to work on finding a middle ground. For this reason of blending in I have actually been wearing darker lip colors lately, since its fall and that's when women wear darker lip colors.
I actually don't mind getting stared at, I just don't want to be the punchline of a joke or a spectacle. If you want to stare at me because you read me male and are trying to figure it out, fine, just keep it quick and get on with it. I think I am just afraid of people staring at me because they think its funny or are looking at me as an object of ridicule. I think this is ultimately why I am afraid to make eye contact with starers, because me looking back at them would be me acknowledging that I am being stared at in the first place. By not looking at the starers, I am, in my mind, denying the fact I am being stared at. It's like I don't want to know I am being stared at, so I pretend in my mind its not happening and don't return the stare.
From my experience the first steps are always the hardest. Once I am going there is no stopping me, I just have to get going in the first place. It's like moving a big boulder. The hard part is getting it rolling, but once its rolling, its easy.