So, I ask the question, what's the worst that can happen???
Telling my SO: this would be the hardest thing to do. I've tried telling her about my cross dressing before in the past, which was something that she didn't handle well. I feel that I need to try again and damn the consequence. The worst is that she breaks up with me. I love her and care for her very much, but I don't want to hide this part of who I am any longer. In the past, my biggest fear was that she would tell my friends, family and work that I was a cross dresser. This used to scare me a lot. Not anymore. However, if I really think about it, I don't think she would get too upset over the fact that I was dressing up... but rather the extent to which I've taken this and just the amount of femme stuff that I actually have. A huge difference from the days where all I would have is maybe a couple pairs of panties, some hose... maybe a silky slip. But now? Wigs, bras, forms, a full and complete wardrobe with shoes, boots, a ton of accessories... Sure, she'd probably dump me right there and then, but I just don't think I could handle seeing her hurt like that.
Telling Family: I have a great family and I feel that I could open up to either my mom or my sister. How would they handle knowing? Not sure... but I truly do feel that after letting it "sink in" that they would be understanding. Accepting? Maybe not 100% - meaning I don't think they would ever feel comfortable with me dressed up in front of them, don't think I would either for that matter, but in this case... that's probably worst case scenario. I don't think it would cause much upset or disappointment, it might generate some questions... but that's probably the extent of it.
Telling Friends: I have a great group of friends - sure they might make fun, give me the razz, but I highly doubt I would loose any friendships if they were to know. As a matter of fact, someone I know recently came out on FB. Not a direct friend of mine, but an acquaintance. He posted a pic of himself en femme and the reactions were all extremely positive! Not a single bad reaction. If that was the worst that could happen to me... then that's not bad at all. In fact, I was a little jealous to be honest.
Telling Work: I went into some detail in another thread about the reaction from work that I might get. We are a small, diverse group where individuality is welcomed! Of course I would expect some razz from work too.. but not malicious... all in good fun! If anything, I truly and honestly believe that it would not make one single iota of difference. Most of the people at work have already seen me with my nails done, eye makeup from the night before which I obviously missed... they already know that I am a little "different" anyways.
Really, the worst thing that could happen is the hurt that I might be causing my SO to feel. I really don't care what others think of me, and I don't want to hurt her... but it's becoming difficult to keep this secret. This, I suppose is what I need to figure out - how do I tell her? How do I minimize the hurt? The answers will come, but whether she accepts this time or not remains to be seen... at least this time, I will not make the mistake of telling her that this is just a phase and that I can stop. I know now that it just isn't true and that it'll never go away...