Contouring and highlighting are going to be your best
friends, trust me on this. :P These techniques help completely reshape your face to give it a softer, feminine look (I have a separate thread here
that goes a little more into detail about that). What I always recommend to men who are interested in cross dressing is to watch a few drag queen highlighting and contouring tutorials on Youtube. Once you've seen the extremes, you can gauge for yourself what looks natural and what's too much.