I'm actually just commiserating... my own ds12 isn't Asperger's, but on the big spectrum, he and my ITguy dh are certainly to one side of the middle.
Last year I asked him multiple times why an online grade was zero... he kept insisting that he handed the paper in. Finally I emailed the teacher, who called me that night to say that she had indeed found the paper, lost in a pile. However, she added that she had been asking him for three days, "Do you have that paper?" "Grades are due soon, are you sure you don't have that paper?" Each time, he would respond "no," but at no time did he think to add, "Because I handed it in." When I asked him WHY, he said, "She didn't ask if I handed it in. She asked if I had it. I didn't have it, because I had already handed it in." It actually can look snarky or sarcastic at times when he responds that way, but it's truly just him being his literal self.
SIGH...
I think dh has trained himself to "decode" what people want and how to respond (even to add in emotion, lol, which is hard for both of them) but I don't think it comes naturally. They are both SOOO smart at many things, but at catching nuances and such, not at all.
I try to tell all of ds's teachers, "Please be explicit. Please don't make him infer stuff. Please write it down if possible," and I also have a lot of discussions with ds that start out, "okay, tell me exactly what s/he said..." (that's where having a great memory comes in handy :)).
Dh encourages me because he is so much like ds, but he has really successfully learned to broaden his communication style- both what he says and what he hears, if that makes sense. I just try to think about what I'm saying, and unlike some others have said, I find that being broad doesn't really work with my ds. He gets flustered if there is any interpretation to be done, so very specific directions work best for him. If I can hand him a list, all the better. I know that doesn't help for quick "go get these dishes" types of conversations, but it might work well for longer chores. We make to-do lists for everyone each weekend and we have a family meeting every Sunday, which helps.
I also find that he can't make the, "and so...." leap. You can say, "how much homework do you have this weekend, because we are busy all day Sunday" but he won't hear the implied, "so do it Saturday." You can say, "I'm going to the library during the day today" and he won't hear "do you need any books?" I have to be very explicit. I actually think in my head, "and so..." and I teach him to both think that and say that. It is a skill that can be taught to a certain extent...
Good luck smile You definitely aren't alone!