Human's are very funny animals. Which makes all of this, impossible to really say. I think there are two reasons for that. First, within any activity there is a range of behaviors. So it could range from wearing panties - something so common its become a clichie, even the Simpson's joke about it - to being a Drag Queen or Beauty Queen in contests. And yes, they have them. It could go beyond that into transexualism also. That's truly a horse of a different color though. So I'll confine my remarks to the crossdressing aspects of this only. But the real question here is "How Far Does This Go?" And no one, not even that other person knows. Which is, or can be, scary.
The second, is that no one knows who/what/why any of this exists, though we can be pretty sure that it manifests itself in different ways. Some people in the transgender spectrum have backgrounds that include child sexual abuse as a victim. Is it higher than the regular population, I don't know. But I can see where how and why you choose to express what you do can be colored by a past sexual experience that was highly bad rather than being good, and reaffirming. I'm sure many CDs have some past bit of sex stuff, perhaps and most likely, not even sex itself but a symbolic linking that plays out in all of this. I'm also sure that most don't remember what it was. The event stuck as an ideal not as a reality.
So, the person dressing might feel liberated, or humiliated, or sexy, or protected, or fulfilled - and perhaps even more than one of those at a time, so being humiliated can become liberating (sigh, I'm not sure how either, but I've seen it happen, so I tend to think it's true - it has to do with playing out our own visions and lives.) Sexy for sure can be liberating, humiliating or fulfilling depending on the person its happening to.
So, you've got something that has a wide range of expressions. That has a huge number of factors going in that shape and color the end goals and desires. So, no one outcome is predictable. There is a very large number who just do the lingerie deal. Others want a complete outfit, some seek special outfits, costumes if you prefer, and just want to lounge around the house in them. Others want to go out to some 'safe' place, others out in public, some even want to perform. Thankfully that number is small.
And, we all know that a lot of our dreams and desires go away after we fulfill them. Doing something a few times is as likely to make it go away as it is to enhance the desire. That and people like to experiment - the scientist in us all - and will often seem to be going overboard when they are just working to set their own boundary.
because he's a CD does this mean he likes men or is Bi given that our itimate life has been so sporatic?
Most CDs are hetro if the stats are to be believed. That they like all the feminine stuff, does not mean they like men too. I think in many ways, its not hard to see it as an escape from the world of men, not a way into it. Given his current life, its not that hard to see that longing for, and obtaining a 'softer' side of life has some merit to it.
"thrill was the attention"..What attention?
Most likely its just attention for the sake of attention. We're all kids at heart after all. Everyone has a touch of Drama Queen about them, and are moved by the Diva spirit now and again. Everyone wants to shout at the world "Yo, Hey Bitch, dig me!" once in a while at least. It in no way means that he wants to dress as a women to have sex. There might well be a strong sexual component to it, but that does not equal sex per se. Ballet and modern dance have strong sexual components to them also, but the audience is not humping like bunnies. I think that a lot of people, really like to be the center of attention once in a while. When you think of all the ways there are to get to that spot, if only for a moment - performing, art, music, theater, Karaoke, making speeches, being a key player at a religion deal-reading the Gospel or something, political stuff, sports - yeesh, the list is endless. Heck, we even have star chiefs, designers and Ice Road Truckers. Everybody needs a little light under the sun.
Though communication is hard, you do have two things going for you. One, the time you have in together, and the second is time for you to think about it from a more relaxed and for the moment, more distant perspective. Having a bit of time to sort it out is a luxury that I'm sure that many in your place would have wished for.
Last, if he is overseas at this time, under that kind of stress. It could be just the way the mind will do something, anything to get around the reality. It might just be a passing thing.