Common concerns that seem to come up time and time again with the SOs stems from lack of education about just what crossdressing is all about.* The media is fond of broadcasting all the sensational stories of transgerderism but never focuses on the the reality that the vast majority of us live in. For you to ever reach a level of understanding you need to become as educated as you can about the subject. That of course requires you to have knowledge about which sources are accurate. I can tell you for certain the media is not one of them,
I have stopped trying to figure out why I like to CD. I have come to the realization it is lke trying to determine why one person likes the color blue and another likes red. If the person who liked red was told from youth it was wrong to like red they wouldn't stop liking red but they would certainly grow up having a guilt complex because they do. Our society has decided men and women should dress a certain way. Does that mean it's right? Women have made it clear they don't want to have to wear dresses all the time or even bras. They don't want to live up to those societal expectations because they are too restrictive. They won the right to dress as they want. Men have not.
The vast majority of men who CD aren't going to have a sex change, start a gay relationship or go out and try to pick up a man and they certainly aren't trying to compete with women. The clothing is just an expression of the inner self. Imagine women's reaction if men would have asked them the same questions when they started wearing pants on a regular basis. The women would have thought the men were overreacting and maybe even hysterical. Women know wearing pants and suits and even menswear clothing are all options they have to express themselves.
So why not allow men the same options? Yes, it will take some getting used to. You first have to get over your fears that your CDing SO is going to change. He's the same he always been but now you just know him better. The better you know him and the more you accept him the better your relationship will become. There may be an initial surge because he has kept this buried for most of his life, but is should subside. I'd even say go overboard and push him to do it. He may not like doing all that work all the time and find just what woman discovered, pants and a loose sweatshirt really are more comfortable. You'll never know until you try. Look at it this way, imitation is the sincerest form of flattery.
*After re-reading this sentence I realized I stated it poorly. I was not trying to say SOs were uneducated about crossdressing. In my mind I was looking at how so many things we once thought were so horrible have come to be openly accepted. This acceptance comes from a eventual reality about what that once horrible thing is really about. Once we find that (outside society's attitude) it is really harming no one, we will ease up on our prejudices. To me, that's the reality of crossdressing; it is truly, in it's base form, harmless. If there wasn't such a stigma, my dressing as a woman in public wouldn't hurt a fly. When you look at a group of Goth teenagers with all their body piercings, wild hair and all, you might think it strange but as long as they hurt no one, what's the problem? I believe the time will come soon when we will look back and ask, "What were we all so worried about?" I'm just trying to help that evolution along.
I want to apologize to anyone whom I may have offended. My typing is slow and can't keep up with my thoughts and I miss putting the words down that properly reflect my thoughts.
I'll put more into re-reading before I post. 
