I've enjoyed reading this thread so far, because it seems to have attracted a lot of people from completely different perspectives, thus the overall answers seem to show that the question, while apparently innocent, has a lot of possible answers, none of them "right" or "wrong". It's just that the question is, indeed, pertinent, and lots of us feel prompted to answer them according to our own perceptions.
I found it extremely gratifying to read so much variety. I tend to agree pretty much with everybody else, even though I have a different opinion! That's just because each view, each argument, seems so mature, well-elaborated, and correctly presented. Of course each of us is biased. But it's refreshing to read on an Internet forum that there are so many intelligent people who have given to such a (apparently) simple question so much thought and willing to share their own conclusions.
I feel a bit humbled to give my own answers. I usually label myself as "mostly a crossdresser", but, as ThePhoenix points out, I certainly don't "fit" in the type of crossdressers that he described seeing around in the late 1990s. In fact, among my own online friends, I just "fit" within a very small group. Crossdressing, for me, has nothing explicitly "sexual" in the usual significance of the term, but that's just because I happen to have an unusually low libido. I say "unusual" because, as a sociologist explained to me when I was being interviewed for scientific research, the "usual" pattern for male crossdressers is to have a diagnosis of hypersexuality (very high libidos).
So it would be quite logical to ask: "Sandra, if you have no sexual urges at all, and crossdressing doesn't even trigger that, why crossdress at all?" (in fact, tons of hypersexual crossdressers ask me that lots of times).
I wish I could answer more clearly, because my opinion has varied over the years (but the urge to dress and present myself as a woman has only increased!). In my very early years as an adult crossdresser, the usual explanation I gave to myself was to get a respite, or a relief, from "being male all the time". I'm now talking about "male" as a gender role and not as a sexual function. Males are definitely socially pressured to fit in certain standards of behaviour (and, unfortunately, presentation and dress as well). At that time I was experiencing intense work-related stress (which never stopped since then), and, as I had the role of a general manager and senior partner of a company I had co-founded, it meant bearing the burden of all decisions (good or bad) and standing by them "solidly as a rock — just like what we expect from a man". It was quite obvious to me that I hated that role. Ironically, I had a much more easy-going job before that, and it was my girlfriend of that time who pushed me into launching my own company. "Men", she said, "ought to take risks. If you don't risk anything in your life, you're a nobody." In a way, most of the things I had to do (and still do!) were always felt that I had somehow constantly prove to everybody that "I was a real man".
This was just a culmination of a long process of "proving to be a man" which started during my teens. Back then I was skinny and had luscious lips (I still do!) and long eyelashes. I thought I looked "too feminine" and strove hard to change that, because at that time I was scared of being labeled as "gay" (specially because I feel strongly attracted to women, not to men, and wished to be seen as a very heterosexual male and a desirable partner). I grew a beard to cover up my appearance. While my mother recommended me, after my teens, to take care of my skin, and even forced me to go regularly to a manicurist and pedicurist, I feigned to hate that and never told anybody how much I actually enjoyed being pampered.
Much later on I was drafted into the military (fortunately for a short period only) but made sure that every women I met knew that (ironically, the Portuguese Army is about 2/3 female, so the argument that "the military turns boys into men" certainly doesn't apply any longer). So most of my life, since my teens, I always felt that I was constrained by society to "fit" into a certain role, but one that I'm not particularly well-suited to play. It's just that I'm a bad actor. I try my best to present myself as male, but I'm always disappointing everybody because I'm so bad at that role (most people don't really figure out why I'm so bad at playing the male gender role; they just see me failing at things that "every proper man should do").
But here the question is, "do you hate being a man?" The answer, for me, is not quite clear. If the question is posed to many unambiguously transgendered people, they will have no doubts and answer "yes". In my case, I definitely hate the male gender role, but being a "man" is more than that. I have also no use for "having sex as a man" because of my incredibly low libido (I cannot truthfully say that I'm asexual — because everything feminine, from clothes to appearance, from presentation to the gender role, truly excite me), so I'm not even one of those people who would say "I hate the male gender role, but love sex as a man". Sex is something which I find no use for, and while obviously I can get excited by attractive women (or not-so-attractive ones who know what they're doing), the act in itself is just a bodily function that leaves me indifferent — in case of doubt, I prefer to avoid it. I have lived with my wife for 16 years, and in the past 7 or so we have had no sex at all (and even before that, it was a very rare event). Neither of us misses it because we both have almost zero libido.
So what else is attached to a "man"? Well, usual characteristics are things like strength and endurance. I have neither, and it's always humiliating to see my sister-in-law, who is 30 cm (that's a whole foot) smaller than me and very very petite, being able to lift a 3-person couch with one hand without sweating, and she has never done sports in her life. While I struggle to lift the smallest things, but I'm always being asked to do "heavy-duty" work because, well, I'm a man and I'm supposed tp be strong. I also have little endurance. I don't do sports (I have a problem with my spine which prevents me to do anything — not even long walks, which I used to love), so I have no endurance to speak of (although I can certainly walk for a long time — several hours — without getting much tired. Well, at least I could do that in the recent past). On top of everything I'm a smoker as well. So... everything related to fitness, strength, and similar "male" characteristics are definitely not part of my experience. But of course everybody thinks otherwise.
As a male, I'm also ugly. There are a lot of definitions of what "ugly" means in terms of "maleness", because sometimes you can be so ugly as to become attractive to the other gender. In my case, it's just an assortment of miscellaneous things that make me indifferent to others. If I had a good muscle toning, and possibly more hair, people might overlook my strange face. If I could disguise it somehow (which I can do so well when presenting myself as female!), I might not be disgustingly uninteresting. But I can't. And males don't do face surgery to look more "male-ish" — at least not around here, not even metrosexuals would do that.
But I can't honestly say that "I hate everything male". There are some advantages to the male gender role. It's fine for me to work with computers, for instance. At the office, we have two gorgeous female programmers — I can imagine that their competence and excellence is often ignored. I'm mediocre in most of my work, but people tend to have much higher expectations — just because I'm male. So that's a blessing in a way. If I transitioned and continued to do my job, I would have to perform much better than any other male in order to be accepted.
My personal experience is that people don't listen to me "just because I'm a male". I have seen so often this argument that women's opinions are disregarded, while men get all the attention. In my case, I have never experienced that. I'm usually completely ignored by everybody (specially by women), except on very rare occasions (when I'm a speaker at a conference where people have no option but to pay attention). So, here, once again, I don't "see" the advantage of being "male".
There are some cases where, however, I do feel this "advantage". When walking around dressed as a woman in the middle of the night, I feel much less secure. Every man I see looks like a potential rapist. When I'm far enough, they will see this strange, tall woman as a "target". If they come close enough then they'll "read" me, and I might trigger a strong transphobic hate. As a result of both, I fear walking around as a woman much more than as a man. So that's definitely an advantage that "men" have: because people expect them to be stronger, they are left alone more often than women (or people passing as women).
It's when I see those amusing lists that I ask myself what real "advantages" I truly have as a "man". I agree that those lists of advantages definitely apply to the average guy, and, if I were one of them, then I'd certainly see those advantages as well. On the flip side of the coin, even if some of those lists are very biased (and some are straight-out sexism!), I can certainly feel attracted to some of the so-called "female" advantages: people are fine if I'm sensitive or emotional. They are more interested in talking to me (I have profiles as male and as a female in several social sites; the difference is unbelievable; of course I understand that it's the male's role to initiate conversation and the female's role to accept or not, but, even so, it's amazing how incredibly huge the difference is). They have no problem in doling out flattery and compliments, when it's quite clear I'm totally undeserving. And, of course, I do get the opportunity to dress what I like, not what I was conditioned to wear, as well as easing myself into a role with which I'm so much more comfortable.
In the past, as said, I saw crossdressing mostly as "relief". I could take a break from all those "demands" placed upon the male gender in our society, and forget, for a bit, that I was supposed to behave like "one of the guys". Just for that, crossdressing had a huge importance to me at the time. Also, while not exactly sexual, I most certainly have very strong erotic feelings while being dressed and presenting myself as a woman. Not necessarily towards anyone in particular; it's more like self-satisfying. I enjoy presenting as a woman... because I like what I see. So, yes, that's totally narcissistic.
Also, in the past, while I was between girlfriends, there was a strong urge to somehow create the image of "the perfect woman". Obviously that image is biased, and it's just a projection of what I consider "the perfect woman" to be and to act — in reality, I obviously settle for much less. But that was one of the triggers that made me crossdress: I cannot get any woman (GF or not) to look and act like I love women to look and act, but, well, I can do it myself, and watch myself in that "ideal" role. Again, this is narcissism to an extreme.
There is obviously also some clothing fetish going on. However, I don't dress because that turns guys on. I dress because the clothes themselves also turn me on. But it's not just the clothes: I need the whole experience. I do partial crossdressing sometimes, when there is no time for full crossdressing. For me, it's not satisfying: panties or boxers, they're there to just fulfill a function. However, if I'm fully dressed and presenting myself as a woman, all the clothing acquires a significantly different meaning. It's not just about the clothes. But the clothes are most definitely the trigger: we're very visual beings, visual imagery stimulates us a lot, and for me, all these female feelings get mostly triggered by the visual aspect. So I dress mostly as a trigger to achieve that state of mind where I can completely "let go" of all the social conditioning as a male, and just become comfortable in my female role. The trigger is very powerful, so I cannot say it's unimportant. I can certainly use other triggers besides wearing nice clothes — the mind is powerful enough for that — but why not go "all the way" if I have that opportunity?
On the other hand, I certainly don't feel constantly depressed and frustrated for being "in the wrong body". I don't have suicidal tendencies because I cannot continue to live inside this body. Because I evaluate to carefully and rationally (a male trait!) the many disadvantages of transition — losing family, friends, a job, moving to another city or even country, starting from scratch in absolute poverty, undergoing painful and expensive surgery, being dependent on medicine (hormones) for the rest of my life (I already have genetic high blood pressure — which is bad if you take hormones — and I already need medication), and, more important, having potentially lots of complications due to SRS... well, I put all that on the scales and say: "Do I really, really want to do all that — just to become an ugly woman instead of an ugly man?" And, so far, the answer has been "not yet". So, clearly, I'm not a (primary) transexual. Just the ability to reason about that means that I fail some of the necessary pre-requisites.
I might be a "late transexual", though. I have always said that if my wife left me (which is highly unlikely; we have very strong bonds which, as said, have nothing to do with sex, but are purely at the intellectual and emotional level), and once my already demented father departs (or loses consciousness of what happens around me), then I would have no further bonds tying me to my "maleness". I have few friends, and most of them are shared with my wife. With her gone, I would feel little reason to keep many of those bonds. Bond-free, I would very likely transition — I would have nothing to lose. Except, well, my dangly bits, but I just use it to pee standing up anyway, so I don't feel uncomfortable about losing it (I do, however, feel uncomfortable with idea of having to tolerate the pain of post-op for several months).
So, to finish: I cannot utterly say that "I hate being a man". I hate the social conditioning that forces me to behave as a man — i.e. I hate the male gender and what it stands for. I hate some of the limitations of my "male" body, and rather prefer to look like an ugly woman than an ugly man. And yes, I'm shallow and vain enough to hate all male apparel — shopping for male clothes has always been for me a very unpleasant task, specially when I see all those gorgeous dresses on the other side of the shop... — so I have to admit that female clothes have also a very strong appeal to me, much more than what possibly most (true) transexuals would care about.
Given a choice, I would always prefer being female. Having no choice, I stick to acting as best as I can as a male for most of the time (thankfully not all the time!), but that doesn't mean I like it at all.
My wife (who is fully aware of my crossdressing but has serious doubts about my gender issues) has given me some good advice, a few years ago. She said that my problem is that I exaggerate all the advantages of being female, while downplaying all the disadvantages. Having three chronic diseases, two of which related to her biological gender, she knows what she's talking about. Being "forced" to endure life as an intellectual woman — while charming and delightful, she is no ravishing beauty, even though she has some very enjoyable curves — she scorns at my vain attempts to look elegant all the time, as if most women could do that (well, her mother does... and she's 60). Hating the time to "get beautiful" she laughs at my pitiful attempts which take eternities in the bathroom just to look minimally presentable; as she always says, "real women have not the luxury to waste so much time, they have too much to do, and have just to go along with casual clothing". So in a sense she says that I love to "look like a woman" because I can afford to do that for fun, wasting endless hours, but if I were really stuck in a female body, I'd quickly learn about all the disadvantages of being a woman, and understand (perhaps too late by then) how I have just been feeding an illusion, and illusions are not reality: when they shatter, people get hurt.
Obviously this comment of hers has struck a deep chord and made me think a lot. What it hasn't done is to persuade me to "act more like a man". Instead, to be honest, I make even less of an effort. I'm quite open with saying to everybody that I shave almost all my body hair, go routinely to the manicurist and pedicurist (at least I can have the toenails painted), get a professional to style my eyebrows, and use seven different types of creams and lotions every day. And I'm quite comfortable in discussing female fashion and female apparel in public with my friends (which sometimes they find a bit disturbing). I have no problem in talking for hours and discuss everything, even participating in typically "girl talk", without feeling embarrassed. All this was something I would be deeply ashamed about, but nowadays I don't care if they find it odd or not.
Sure, "hating to be a man" and "being a woman" is so much more than that. I'm aware of it! So, to be very truthful, I would say that I "deeply dislike being a man" (both in terms of social gender and physically), but I don't utterly loathe it to the degree of being obsessive towards changing gender as quickly as I can. While I get mildly depressed when I cannot dress and present myself as a woman, it doesn't shatter me and utterly devastates me. It's just one of the vast amount of things that frustrate me, but not the only one. Surely it's the more important one. But I'm also aware that discarding this male body and adopting a female gender will not make all the other issues go away. In fact, I would just acquire a new set of issues to worry about, and the net result is that I wouldn't be "intensely more happy" just because I switched genders: I would just exchanged some issues (with which I'm familiar with and have learned to deal with) with a new set of issues (which I would yet have to learn to deal with).
