Somewhere along the line, my son has decided that it would be a bad thing to go out with me when I'm en femme and it's probably my fault. A couple of years ago, he was misbehaving while I was getting ready to go out for a cafe night. From memory, I think that the issue was that he didn't like what my wife was planning to prepare for dinner for them while I was out, and was having a tantrum about wanting something else instead.
I don't remember exactly how I said it, but I asked if he would prefer to go out for dinner with me instead of staying home. The idea was completely impractical because he goes to bed around 8:30, and I typically don't get home from a cafe night until after 10pm. Add in the fact that it was a Tuesday night during a school week and he absolutely hated the idea. I think that he thought that I was threatening to punish him by taking him out with me, and at the time that might have been true.
Unfortunately, the side effect of that is that ever since, any suggestion that he might go out somewhere with Alice has been met with immediate rejection. He doesn't apparently have a problem with me going out en femme, but doesn't want to go with me, even if it was to somewhere such as a shopping centre where he has no reservations about going with me when I'm dad.
I'm still trying to work out if I can turn his attitude around, and if so, how. I've got him to see op shops in a positive light by taking him there on the rare occasions that my wife is away and I have to take him with me when I do banking on a Friday afternoon or Saturday morning. We browse the boys racks and pick him up a shirt or two each time, but that's always with me as dad. Perhaps one day I'll suggest that Alice can take him op shopping and his interest in op shopping will outweigh his dislike for the idea of going out with Alice. I don't know.
I'm not going to push him into going out with me en femme, but I'm hoping that at some point in the future he'll choose to say yes. It's a shame that nobody that I know seems to have fancy dress parties, as that might have provided a good opportunity that isn't threatening to him. Of course, Alice would have to dress up as something or somebody. I'd have to think about that if the opportunity arose.