first of all-it took courage to share this with us-so for that I say "thank you"
...my story is very similar to yours...always loved heels..always on ladies..bought a couple pair just to see how they felt..then, as I have written elsewhere, my wife let me try on a pair of her old thigh-high stockings and I "discovered" a skirt that was too large for her but fit me nicely...
http://i21.photobucket.com/albums/b2...ysWanted-1.jpg http://i21.photobucket.com/albums/b2...irstLook-2.jpg http://i21.photobucket.com/albums/b2...oserLook-1.jpg
I don't cd completely-up to but very limited use of cosmetics-but I have spent some very pleasurable Sunday afternoons in stockings and spikeheels...
..and I have progressed to wearing boots with heels whenever I go out dressed as Jim...
..just relax and have fun with them..your sense of what is "right or wrong" will set the parameters for what you consider "appropriate but emotionally-challenging activities..."
JSpikeheels