*hugs all of you* So many great suggestions, so much good advice!

I can see where this can get sticky: his "truth" is that he genuinely wants to please you, and walking with you (albeit on sore feet) is still preferable to staying at home when you expressed a desire for company. The truth you're curious about, on the other hand, is sometimes what he would actually want as an individual if you weren't a contributing factor to his decision making.
Exactly.

If I am understanding correctly, I can see where you, as the Domme, understand and appreciate his submission but are interested in knowing about him and his preferences more specifically and individually at times. There is a caretaker aspect and a protective aspect to being the one "in charge" and how can we care for a sub if we don't know accurately what they want and need and think about as well?
100%

Sometimes, being asked to arrange something can also be very scary.
Agree completely. He does not handle desicion-making well; I love to decide everything, so in this way we go together well. I just feel that in order to make the best decisions, I need to have all of the information. I think stressing to him that he is, in no way, making any decisions and that I'm just asking for information from him will help.

devilishsub, I can't say I'm glad the internet ate your post (I hate when that happens); but I have to say your abridged version is extremely useful. I think I'm going to print it, especially numbers 1,2, and 3. It's just beautiful.

Of course we were going for a walk anyway. But if he's going to suffer for my sake, I want to know about it.