This a response I recently sent to a very nice but anonymous closeted girl who had sent me a message and so in a flash of typical t-girl egotism, I thought I'd also share its contents with my few kindly faithful readers...
The best advice I can give you is to think hard about your dressing and why you feel so ashamed of it. Are you yourself ashamed and think it's wrong or immoral, or are you worried that those around you will view it that way and will reject or humiliate you? If the answer, when you look into your heart is the latter, then you may want to start thinking about whose life you are living. No one has the right to tell you how to live your life as long as what you do does not harm others (and if someone is unchangeably embarrassed by who you are, then in my book, that person does not truly care for you).
I have talked to so many girls out there like yourself that are so deeply ensconced in their own self-constructed closet of secrecy, shame and depression that those feelings come to rule all parts of their life. And believe me when I say I speak from experience - I was in that closet not much more than a year ago...
If you ask me, the first step is to look into your heart and be honest with yourself. For most of us (but not all) dressing is a fully enmeshed part of who we are and purging it is no more useful or successful than trying to stop breathing or eating. If you find this applies to you, take steps and make decisions (but always at your own pace and comfort level) to fit that part of you into how you live your life. When you achieve a decent level of self-acceptance then all else will flow from that. If you are not ashamed of it and you communicate this belief to others, most will feed off of this and will not reject you for it. Some will, no doubt. These steps are never easy nor even advisable for the faint of heart, but for me at least, they were necessary.
I had lived with depression and self-hate for so long because of this that it was killing me slowly from within. I made the conscious decision (because I saw clearly that is was killing me) to no longer feel that way and slowly my life started making sense and I was able to have fun again, to enjoy and revel in this part (and all parts too) of myself. I still have obstacles to climb but at least I am confident that I will face them all knowing I'm doing it for myself (i.e., for the right reasons) and not because of what society or family or friends want or what I think they want for me.
Anyways, I've babbled on long enough on this soapbox. My words will not solve any of your problems, but I do hope they might shine a tiny speck of light into your closet and help you realize that there is always hope and that there are many others like you and me out there. In the end it's your decision alone whether and when and how to emerge from that closet or not, but that doesn't mean you have to make the journey alone or without the support of your trans-sisters...
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