Hmmm interesting.
I'd suggest direct plain cut-to-the-point statements. Also, ask 'why' (tone is crucial when it's done though). Perhaps even frame it in a 'talking about your emotions is a feminine thing to do' discussion to help them learn to slowly open up. Many guys (skirts notwithstanding) are thoroughly emotionally repressed and have very little emotional vocabulary or self-awareness so that might be a slow process.If the SO understands how important crossdressing is to the CD, how does the SO convey to the CD that all of the other things in thier life are equally as important to the SO?
One thing I find is that when forced to hold my tongue about dressing or have to repress myself the last thing in the world that I'd want to do is go near womens clothing departments/stores. It's just too painful. Sort of like making a diabetic help shop for sweets. Lots of social events can be a nasty and cruel reminder of what I'm locked away from too and withdrawing, isolating oneself is sometimes the only way to cope.
The CD may feel less controlled if things are put as requests rather than demands. An appeal to fairness would probably work if it appeals to the notion of an opt-in bargain or trade. Like 'I'll go to this with you if you go to that with me' but not 'I went to that with you so you should want to go to this with me'.