OK, I'll bite. Is crossdressing OK?
Of course it is. They are just clothes, and the standards for what we wear are entirely arbitrary. Take a look at this guy:
jacobean-man-1.jpg
Oh, back in the day he was a stud. Now? While this wouldn't be crossdressing, I don't think most of you would be viewed as being hyper masculine while wearing this getup to the office...
Being yourself is OK. Our society says it's not OK to be yourself. It doesn't just do this to CDs - there are all sorts of people who are discouraged from being who they really are:
gays
lesbians
transgender people
asexual people
and scores of cisgender, heterosexual people who are forced into lives they DETEST because they want to be seen as "normal."
Y'all are mostly feminine men, or gender fluid trans, or bigender trans, or a few of you are actually women, but just don't know it yet. Or perhaps some of you are simply fetishists. None of that matters, really. Because you aren't hurting anyone. Oh sure, other people may take great umbrage at your presentation. I've certainly experienced this first hand. But the thing is - I didn't DO anything to them, and neither did you. It isn't my fault that they freaked out over the way I looked. And sure, you may take negative social consequences for being out and being gender variant. I sure have! But again, that doesn't make it wrong - it makes the people who did those things to me abusive.
Now one argument some might make is "what about our spouses? Don't we hurt them?" Well no, not really. Yeah, some of them freak out when they find out about this stuff. This is really unfortunate, and a really good reason for coming out BEFORE you get serious with someone. But at the end of the day, you are under no obligation to hide who you are from someone else.
So you might then ask, "What if my spouse suffers bad social consequences because I'm a CD? Doesn't that make it bad?" Again, no, it doesn't. It would be awful, and I have NO DOUBT that it happens, that some spouses do suffer if their gender variant spouse becomes known. My own wife claimed this happened to her. I think it's horrible. I also think it's not my fault. Let me give you an example of why it isn't.
Imagine a really dysfunctional and abusive family - drunk Dad, mousy mom, and junior. Suppose that every time junior gets a bad report card (junior is ADHD, so umm, his grades aren't the best), drunk Dad ties one on and beats the living hell out of mousy mom. Is junior to blame for the horrible treatment his mother receives? No, he really can't help being how he is. And his home life probably doesn't help either... No, the fault in all of this lies with the abusive Dad who feels the need to exact vengeance on SOMEONE - doesn't matter who, really.
Our society, and an awful lot of people in it, are like the drunk Dad in my example. They lash out sometimes for basically no reason - just because someone is different. And while I think anyone should absolutely consider the safety of themselves and their family before coming out as some form of trans, at the end of the day, what happens in the aftermath of people discovering this about you is just not your fault.
Providing you aren't violating someone else's boundaries, it is OK to be yourself. In fact, being yourself is a really fundamental boundary. We need to be who we really are. So crossdressing is "OK", because make no mistake, it is a part of who you are. That society often seems to say this is "not OK" is abuse. It will be argued by those who are transphobic, that by appearing CDed, you are violating their boundaries - you are hurting them. I assert that boundaries like that are UNHEALTHY - "you must look and act a certain way, or my boundaries are violated!" A boundary like that, which attempts to manipulate your behavior, is abuse.
Unfortunately, in these racist, sexist, ableist, homophobic, transphobic and increasingly narcissistic times we live in today, healthy boundaries are often scarce.