In recent light of my best friend (Steve) situation, I have taken much thought regarding this issue and I wanted to share my feelings with all of you.
What does it feel like to be a woman?
This is a question that should be of profound importance to the CD community, although I have never seen it discussed in any depth. It may seem self-evident that, as a man, I simply cannot know what a woman feels. It may even be true that, as an individual, I can never truly know what any other individual feels. Yet it is commonplace to hear CDs talking about their 'female persona', their 'feminine side', or the woman 'inside them'. I don't want to deny that all these men feel something but how do they know it is anything like what a woman would feel? How do we even know that women feel differently to men?
I think that a significant part of the pleasure of cross-dressing for me is that, in some strange way, it frees me to experience myself in a different way. I can be more sensual, more auto-erotic and I can feel things that I don't usually feel: like feeling feminine. The more I cross-dress, the more this experience of myself spills over into my 'drab' times but it is still strongly associated with the dressing. Is this experience anything like what a woman feels about herself? Is this even the same experience that other CDer’s feel when they cross-dress?
In the end, I believe we can never know the answer. However, I believe that this feeling of femininity or of being a woman is very real and that it even has a certain validity. While a man can never really know what it feels like to be a woman, I believe there are some aspects of the experience of femininity that we can share. In particular, it is a sensation of being physically attractive as a woman that CDer’s crave and seek, through cross-dressing, to achieve.
It is the feeling of presenting to ourselves and the world as an attractive female that we call femininity and I want to argue that this limited way of experiencing the female condition is at the heart of what it is to be a crossdresser and is also the source of much of the confusion about gender identity that afflicts us.
If crossdressers feel the same way that women feel, we would expect the way they describe their feelings to be similar. There are so many dimensions to this that it is hard to know where to start.
One of the most common self-reports from crossdresser’s is that they feel so "feminine" when dressed. Do women report the same thing? I think they do - not so often perhaps and only when they are really dressed up in something special - but I have heard it often enough to believe it. So what do women mean by it and do crossdresser’s mean the same thing?
Feeling "feminine" is not like feeling sexy, or handsome, or 'cool', or any of the other things a man normally feels when he dresses up in his own clothes. Probably the nearest feeling a man could have that is still more-or-less gender-appropriate would be to feel 'elegant' but this is still a long way from feminine.
Feeling feminine is a heady blend of feeling pretty, desirable, submissive, delicate, touchable. It is about seeing one's self as something that could be desired and cherished for its very vulnerability. About relishing and emphasising one's own attractiveness and desirability. It is also very much about having the physical attributes and appearance of a woman.
How do I know? Well, of course, I don't. I only know how I feel when I'm feeling feminine and that the way I describe it seems to coincide with how some women describe it.
Another very common self-report by crossdresser’s is that they feel so much more "natural" when dressed. In reading such reports one can almost feel the sense of relief, the draining away of a pent-up tension as the female persona supplants the male. So we need to ask ourselves whether real women also feel 'natural' when dressed in gender-appropriate ways.
I think the answer to this is not very clear. Although there are clearly many women who are comfortable in feminine clothes, I have often heard women state that they feel more comfortable and more relaxed in traditionally masculine clothing. Some have also told me they feel very uncomfortable, exposed and even unpleasantly vulnerable in particularly 'dressy' outfits of the kind I would die for.
The situation is complicated. Personally, I regard the feeling of 'naturalness' that comes with cross-dressing as, at least partly, a feeling of relief and relaxation such as any addict feels when their craving is at last satisfied. The rest of the feeling is the reduction in the constant tension we experience between our true physical appearance and the appearance our instincts tell us we should have and which we can approximate when dressed.
If crossdresser’s feel the same way that a women feel, we would expect behaviours that reflect their inner states to be the same as those of women who feel the same way. There is, for example, lots of evidence in the psychological literature that women and men really do feel things differently.
An example I saw recently was the finding that men cry less than women, that men cry for different reasons than women (more often crying with happiness than with sadness for instance) and that women have more reasons to stop crying than men (for example, through being comforted). Of course, such differences might be learnt rather than innate but that doesn't matter. The point is that, truly to feel like a woman, the crossdresser would need to experience this different pattern of emotions. The fact is that we don’t.
I believe we cannot fully share the feeling of being a woman, not only because of the distinct differences in brain chemistry, hormonal make-up and physiology that nature handed us but also because of the very different lives that males and females experience. None of these things can be undone by dressing up and walking differently.
I believe we have many drives or urges that are part of the physiology of our brains. They make us social animals, they make us eat, they lead to sex and reproduction. Yet we experience these instinctive drives. They are not entirely subconscious. We feel hunger, we feel sexual arousal, we feel loneliness. Some of these feelings are integral to our gender identities as men or women. The drive that makes me competitive with other men, the urges that make me ogle women who pass in the street, the instincts that drive me to copulate, are all part of my identity as a man. To present to the world as an attractive female is, likewise, part of a woman’s gender identity.
As crossdresser’s, when we feel our inappropriate urge to present ourselves as an attractive female, we probably experience it in exactly the same way that women do—as something we—and they—would call femininity, or being attractive, or feeling like a woman. The fact that is only part of the full experience of being female escapes most of us and leads to confusions such as feeling that we are women "inside" while at the same time having primarily heterosexual desires.
Yet, our presented sexual self is such a big part of a human being’s identity, it is quite understandable how the confusion arises. Couple such a dysphoric instinct with below-average masculine drives in other areas (half the world is below average by definition!) and it is easy to see how many man would feel they were meant to have been women really and that their masculinity is some kind of horrible mistake.
So I have come back to the conclusion, at last. It is the actual sensation of presenting to ourselves and the world as an attractive female that we call femininity and this limited way of experiencing the female condition is both at the heart of what it is to be a crossdresser and also is the source of much of our confusion about gender identity.
I feel this to be of key importance to the whole experience of crossdressing and I hope you will share your own thoughts with me and the other ladies of this website.
Love
VickiCD
Still, as I was telling a friend this morning, I sometimes tend to get lost in my own brain. Oh well, I have no doubt that that very fact is also a part of who I am. Glad you enjoy my meandering musings, girl! 
You're missed! Glad to see you here! 
