I'm not sure where I'm supposed to post this, so... the main forum.
I apologise if the title is a misrepresentation. In the least likely of circumstances, I finally spoke to my parents about Lily, but not as Lily. (I wish for the latter, but I wouldn't.) They weren't angry - perhaps emphatic, extremely worried, but trying not to show it. I openly admitted to them that I was feeling very conflicted about the issue (even myself I admit to being unsure, even now, of my motivations for adopting a female persona? identity? for myself, the clothing being all I could discuss with anything resembling certainty). I don't feel too comfortable in my own body - I even don't like getting erections, mind you - but it's something I've conditioned myself to live with because I dare not mess with God's will. (I only make this accusation of myself.)
My father showed me a photo of myself in a suit, taken barely a two weeks ago, and remarked on how handsome I looked - how manly I was - and that it would be remarkably absurd for me to try to forsake all that and let Lily (not mentioned by name even once) come to light instead. He claims that since I, James, already have issues socialising and few friends, I will probably not have anyone left now if I threw the doors wide open. Even I acknowledge that when I am out as Lily, I would be one hell of a tomboy. The least I can do in the short term is probably not to crossdress, but I genuinely doubt that will solve anything in the long run, as it stands.
I am seeking counselling anonymously for now. My parents still acknowledge me as their son, a college student with everything to lose (don't we all have?). Mum definitely far from thinks I'm pretty - much the opposite - she thinks I look "weird", natural as I think I may be. She also considers me ungrateful for harbouring the thought of being out as Lily - it simply goes against the man she raised me to be, and I, to some degree, understand where she is coming from with this. I, after all, am the only child and thus my parents' greatest investment.
As much as I want to move on the soonest I can - I first and foremost have my studies ahead of me - I believe this subject warrants frequent discussion with them, not matter how thorny it may become from here.
Cultural note: my parents live with me; government housing is only available at the age of 35. In Singapore, adult children living with their parents is somewhat common, if not encouraged - but it is still the norm to move out on gaining financial independence, typically a few years after college. It is a social expectation to take care of one's aging parents, something which I (will) do proudly.
Addendum
It bears note that my family sees it no differently from addiction, albeit fallaciously referring to gay sex as well in the same boat as smoking or illegal narcotics. I've had to correct them on this matter. They are otherwise (surprisingly at that) inexplicably accepting of me being bisexual, although they do hope that I get a girlfriend (gay marriage is still not recognised otherwise.)
This isn't the first discussion, but I initiated this one myself.