Talk to her. Talk with her. Tell her that this is how you feel; tell her about your fears and anxieties. Ask her what her own thinking is on this issue. Aside from love, trust, respect, and friendship, healthy communication is the best way to make the relationship move forward. Give her the opportunity to be as emotionally honest with you as you've been with her. And, yes, be prepared for whatever it is she might feel. It might not necessarily be pleasant (and this possible "unpleasantness" is precisely what keeps so many CD's from being honest with their SO's; this is unfortunate as it forces CD's to be dishonest with themselves, as well).
I was really confused, so I found it difficult to talk about it. Now that I've got it thought out more I feel I can speak to her about it. I can't very well help her understand if I can't quite understand it myself.
You sort of face a choice, here: do you give in and go with the flow (i.e., keep your crossdressing under wraps, so to speak)? Many here will say you probably should. Or do you more fully embrace who you are and try as best you can to deal with the emotional consequences? This can be a very tough (and sometimes dangerous) road (cf. Gwen Araujo or Brandon Tina, for instance).
I sort of want to find a balance in the two. I don't see myself shouting to the whole world that I'm a crossdresser, but would probably just act more like me in the area rather than who they want me to be. I want to take it tactically so there is as little issue as possible. Being with an armed drill team with some great, loyal, understanding and strong people will be a plus for me also. They don't seem to care about such things, and MOST of them are trustworthy and loyal enough to make sure nothing happens to any member. I can cope much easier with them at my side.
The choice you make will depend on many different factors. Where are you in your crossdressing, Darth? Do you simply enjoy the occasional quasi-fetishistic underdressing? If so, there's no reason this knowledge needs to be public. Or, on the other hand, is your gender variance so compelling that you feel, strongly and unequivocally, that life would be good only if you could present as a woman? if you could pass in public? You'll need to address these issues.
Underdressing does nothing for me. If I can't see it, even if I know it isn't there I don't feel comfortable with it. The change has become strong enough to where I feel compelled to express it openly. I know I would feel much more at ease and more alive if I could present as a woman. Sure I don't want to appear as this 24/7, but I feel that the urge has become a need.
Is there any adult at your school--an adult in a position of responsibility and authority--that you trust, Darth? A counsellor, perhaps, or a teacher... someone you know that you could turn to and that would stand in your corner should things turn hairy (or, rather, smooth-skinned)? What is your school's policy regarding harrassment and discrimination? What is its atmosphere, in general? Are your peers tolerant, as a rule? or is it the opposite?
There are two adults that I feel are trustworthy. The problem is that I will have neither of them, and will only be able to speak to one of them. However as far as the school goes she is just "another brick in the wall" and would hardly be effective if I was in dire need of something. On that note no teachers would ever be effective if it came to discrimination. The school has no problems with it, only because the people who are different are "cool." I am not. The only people who look up to me or respect me are either spongers or other JROTC cadets, and that only goes so far. This would be something new to them if presented, and the publicity and anger over it would likely trigger insane reprecussions. However that would be if I actually dressed to school, which I don't see myself doing. As far as telling a few people, the only people I would tell aren't gossipy, so the issue probably wouldn't be TOO serious. People just probably would never find out.
Above all, you need to evaluate your own gutsiness and your own ability to handle the difficult emotional situations you're likely to encounter should you deliberately "out" yourself. I can tell you from experience that outing yourself can be extremely satisfying but it is never, ever easy to deal with the consequences. There's just no way I would've done it at school when I was your age. But, then, I was fifteen during the macho 70's when John Travolta's "Tony Manero" was every guy's ideal role model (and here I wanted to be Olivia Newton-John! Laughing ). I'm thinking (and hoping) that things are slightly different today. But I'm not sure. You need to feel this out for yourself.
In this school if you are strong as well as different, then there is no problem. While normal people regard me as strong, but if this started to be known people wouldn't care about that, as none of them like me already. They didn't like me as soon as I started dating their good friend and wasn't good looking enough or wasn't them... to keep it short at least that was the basic bits of it. Certain things made it worse, but either way people somehow degraded their opinions of me because I was dating and in love with somebody "higher" than me. They'd probably try to take me for a ride, but fortunately the only times they could ever try to take a chunk out of me I'm armed and backed up. Things are different enough to where I don't think it would escalate that high, I've never seen it for those reasons, however with the last sentence you can trust it would be covered if it did escalate.
One thing's for sure, though: if you go public with this, you also force your SO to go public as a CD's SO, as well. This is something you'll also need to discuss with her.
I know. I don't plan on letting everyone on the planet know... but just a certain level. Semi-secretive. Some can know, others can not. I was planning on talking to her about that.
Survival is paramount!