Landon:
I can understand your need to tell someone and transition. Is it our counselor you wish to tell, or perhaps you should be speaking to a therapist?
Also, what is it you are going to tell and what are you going to ask? Telling her is one thing, but are you, in fact looking for advice for how to transition?
Also you may want to investigate what your school's views on LGBT acceptance are. That may be a more crucial issue. If your school is accepting of LGBT youth, then, regardless of her personal views, your counselor would be required to accept and assist you. But even if the school and your counselor are accepting, neither of them, probably, have not had any experience with trans youth.
I would recommend that you speak to a properly trained gender therapist if at all possible first. If that is not possible, you could approach your counselor and simply ask her about the school's position on LGBT issues. You wouldn't necessarily have to disclose anything about yourself, or at most, simply say that you are questioning and are looking for more information.
Also, Landon, you didn't mention anything about your family, how would they take to this issue?
And since you have been cruising the forums for a bit you know that we like to get to know our brethren when they join. So take a moment, if you can, and tell us something about yourself. I'm sure one of our official greeters will be along and congratulate you.
It's good to have you here, Landon!
Talk to you soon!
-Sandy