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Breakin' social taboos
Well, this is certainly the kind of situation I think most of us are trying to avoid when we choose not to disclose this particular behavior to our wives and girlfriends. It's remarkable that you are actually taking this ball and running with it, though, and that makes your finacee a very lucky person. The thing is, though, is that it's so often NOT "just clothes", but rather something that lives deeper down.
He may say to you that he doesn't want to be a woman, and that may well be true. But it's also the only answer that he knows you will accept. What if we were given the choice at birth, knowing full well beforehand how it would be with us? What would the choice have been then? I would have chosen female over male. But it's only a fictional concept. As for me, there are two different questions to consider. One is "Do you want to be a woman?" The answer to that is yes. But the other question is more pertinent. "Are you going to change to become a woman?" The answer to that is no. I will not pursue the path of transition, and will remain as I am. And I am my wife's husband. I choose her.
But when I'm dressed, I usually go the whole 9 yards. Except for the usual giveaways, the large hands, the broad shoulders, etc., I look like a woman, and have passed as one rather surprisingly easily. Not always, and not to everyone, of course, but still.....it's quite obvious that I'm presenting as female. It's not just the clothes. It's a desire to exist in the world as a woman. At least this is true in my case.
It's also important to understand that this does not change who I am one bit. It would only change my wife's perception of me. She need not ever fear that she will lose me to a gender reassignment. But I think most women want men who want to be men. I'm not adverse to being a man; heck, I am one, and I'm going to stay that way. But given the choice, I'd have opted for female, and for many women, if not most, that's a game changer. And that's too bad, too, because it doesn't make one a lesser person, or a different person, or unworthy of a woman's love and devotion. Remember that but for a genetic crap-shoot, you women might well have been men instead, and you'd be the ones looking at the pretty clothes and longing to be able to put them on.
Think about it.
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