This may sound silly, but it sounds like both of you are trying too hard to be considerate of each other's feelings, the end result being that neither of you can step forward and take control so no progress gets made. In other words both of you want to be submissive at the same time.
One one to get out of this rut is to agree to take turns on who takes control each night. By simply alternating this, you no longer have to negotiate who does what and when.
My other comment is that there is a lack of normalcy about the whole proceedings, in that Paige's crossdressing is seen as an event in itself. I think that is putting too much focus on it. I think it would be great if you guys could find more normal things to do socially. In other words let your SO decide what he wants to wear and then go out for a dinner, go to the cinema, go for a walk etc. I dont know how possible that is for you right now but I think that would be better than just staying at home. I suspect that Paige is getting bored with the current arrangement and wants some excitement. Are you not bored also?
Hope that helps. Otherwise you sound like a great couple.
