Another excellent question!
theponytail - I have very similiar worries except I worry that there might be NO filling in of my cheekbones, rather than too much. However, at the other end of my worries, I would also be worried about their potentially being too much fat deposited on my face. Naturally, I'm looking for the pleasing middle-ground of feminine fat on the cheekbones...but not too much.
I seem to have a face much like you perhaps. High cheekbones, with a hollow underneath. I get the most compliments about my cheekbones, too.
I too, would really hate to loose the face shape I have at the moment, as it's quite feminine due to the cheekbones (lumpy nose and brow-ridge aside). I wouldn't like to have a chubbier face personally as its not what I've come to expect from my face. However I know many cis-girls with plump cheeks and their faces look very feminine and rather delicious to look at. They look full of life and pretty femininity, but of course the catch is that they don't look like runway models (apart from Sophie Dahl). So I guess there's pros and cons.
I would add though, that the thin male face looks great when you're young, but as you age, because males don't have the subcoutaneous fat to smooth out the skin, modelsque men quickly become gaunt-looking and older than their years. Its what's also happening to me now. A few years ago, my skin was very smooth, so my face looked great. But now I'm getting older, my hollow cheeks make me look older and more gaunt, and therefore much less feminine. But, I still get the cheekbones compliments. So once again, pros and cons.
Very true that you need to actually be able to put on weight in order to distribute the fat. Most likely, you may notice that if you whole body begins fattening up under the skin and on your thighs, and you feel more tired - this could be the signal that your metabolism has started slowing down to a more female speed, and therefore you'll be increasing in fat distribution. So ultimately, keep an eye on it, and act accordingly.
I don't think worrying about looks should be considered shallow anymore, for anyone. We live in a media and image-orientated age now. There is no avoiding it, whether your a geeky science technician or a model, everyone has to look their best or face the social consequences. And of course as MTF, there's a massive emphasis on how we'd be judged, so looking as attractive as possible is paramount. You can get away with more things the more good-looking and stylish you appear, whether your a kid, man or woman. So don't feel guilty :p I worry about it all the time, as if I don't and won't look attractive, I'll expect a sh*tstorm of social abuse. Sad but usually, true. (though sometimes people aren't as stupidly judgemental and shallow).