Welcome advice and a somewhat recent scare (cont.)

(continued from my previous post)

Looking back, after I’ve thought in greater detail about all of this for a few weeks, the moment where I was “caught” earlier this year would/could/should have been the prime time to talk about this further with my girlfriend. But for one reason or another, it just didn’t happen. My being a little bit (ok, a lot) nervous and shaken up following the whole episode didn’t help either. So here I am today… still having not discussed what happened that night or the larger issue, the fact that I am a crossdresser, with my girlfriend fiancee.

Taking into account Janie’s and Gabrielle’s thoughtful advice, here are my thoughts…

• The trust issue/keeping secrets is bad.: that should go without saying. But in a way, it’s not quite a secret anymore, isn’t it? Granted, it should be openly discussed again with my fiancee, but that’s what I’m building myself up to with all of this rambling.

• How important is crossdressing to me? Do I understand why I do it?: These are tough, but necessary questions to consider. I have tried to understand why I dress for a long time, and when I started, it was probably for much different reasons than it is now. But in the end, the only thing that I can conclude is that I enjoy it; it’s not that it feels proper, but it feels good… I’ve always been fascinated by (even jealous of?) the female form, and they do say that imitation is the sincerest form of flattery, right?

  It’s fair to say that I’m in touch with my feminine side, the one that boys are raised to suppress as they grow into men, more than “normal”. I’ve always been willing to help my fiancee shop for new clothes (in fact, she prefers that I shop with her, instead of anyone else), and as I’ve mentioned in earlier posts, I’m intensely curious about what it’s like to actually be a woman. While men are tough, harsh, brutish and… handsome, women are shapely, sexy, classy and elegant, seductive and, well… beautiful.

  I have to admit, the idea of being seen as “beautiful” by someone brings a rush of excitement. I’m pretty sure this was the hook that drew me to crossdress when I first began. But as I’ve grown, my mind wanders to what it feels like for a woman to have sex with a man, the thought of being a woman during sex brings the same rush of excitement (more on that some other time). It’s supplemented my original desire to be seen as beautiful.

• Be prepared for questions and potential fallout.: As much as I love crossdressing and would love to continue to grow in that aspect, the thought of losing my fiancee because of it frightens the shit out of me. Actually, it’s so not even an option (losing her) that I’m willing to give it up, absolutely, no questions asked, if it ever came to that. However, I don’t think it will come to that because of how things have been since I was caught (in essence, a non-issue with her; admittedly, it’s more of a don’t ask/don’t tell kind of situation, but at least she’s still here with me now. That’s got to stand for something, right?). Nonetheless, I’m confident saying that when the topic comes up again, I am definitely prepared to answer the questions she will most certainly have.

• No surprises and timing is everything: OK, don’t worry, I’m not going to come home from work one day, kiss her hello, walk into the bedroom, change into a dress and high heels while she’s sitting on the couch, run out into the living room and yell, “Surprise!” It’s just not going to happen that way. However, I’ve run through my head thousands of different ways to tell her that I crossdress and I’ve got a few solid options. Again, timing is everything, but no matter how good the timing and the chosen conveyance, it’s still something that will take a leap to bring up with her. In a way, it’s almost as nerve wracking as choosing the right time to propose her and then actually getting down on my knee and getting the words to come out.

  And last but not least…

• Good luck, it’s a gift and not a disease!: This is obviously the most comforting piece of advice about the subject, and it makes me think that it actually might fly with my fiancee. I’m not expecting to end up at the point where I go out (ahh!) for drinks with her on a Friday night in girl mode, but I think that if she knows it’s something I enjoy doing, she might be able to accommodate it in some way. Of course, there is the ultimate plus side of a partner that is more in touch with her and the potential to spice up one’s sex life. Who knows…

So, I’m sorry it’s taken so long to get this out, but like I said, I’ve been thinking about it a LOT and I needed the time to kind of synthesize everything together. When the day comes, as nervous as I’ll be, I think I’m ready to handle the discussion. Now, when that actually does happen, I don’t know. But I will definitely keep you all posted.