Mia-
How is he with story sequencing? I'm wondering if you started with picture cards, then upgraded to sentences, then paragraphs- cut out and have him sequence them, if it'd help him get the structure? Also- how about Venn diagrams of characters that he likes- what they have in common etc?
We're in the same writing boat. A blank page induces a panic attack nearly instantly! But he is learning to expand a bit with guided questions. (of course- this is me not the school, but it's made a big difference). I use game characters a lot and I think it'd work with your DS too! So I'll say- do you think that "Joe" is more like Mario or Bowser. Tell me three ways. It gets him thinking about things he already understands and how new characters relate to those.
And I'm teaching him to type. Because frankly, other than school, writing has very little purpose that I can find! :-)