Here's how I did it, rather embarrassingly, about seven or eight years ago:
- Wrote up a document confessing to my "unusual" interest in braces, laying out the background and details.
- Got drunk with girlfriend (now wife).
- Very nervously presented said document.
My girlfriend's reaction was basically, "That's it? That's what you were all freaked out about? That's no big deal. It seem pretty harmless to me." We probably build this up WAY too much in our heads.
Now, I will say that this girl is the most open-minded, sexually and otherwise, I've ever been with. Some women are obviously a lot more uptight, and I've experienced them, too.
Anyway, it's been onward and upward ever since, through fake braces and now with her in real braces. I'm VERY glad I "came out of the closet" with her. My life wouldn't be anywhere near as satisfying without this whole experience.