Since writing (or typing) is so hard for him, that means his process is too slow to get his mind to wrap around the stuff to be communicated and hold it there. So he doesn't know how to outline (a common problem among kids his age, just exacerbated in him by his disability).
He has been assigned a monster essay that must use primary sources. He had the primary sources in hand, and he understood them, but he couldn't reduce the complicated verbiage of the teacher's assignment to anything he knew how to write. So, we sat down and I broke up the teacher's assignment into its components and made a grid for him. Then I asked him to list the primary sources he was given and we talked over which sources addressed each part of the grid. Having put down on paper (well, on my computer screen) the issues, we put down the outcomes and their portents for the future of America (which the teacher also asked for).
In the end, we had a 13-19 paragraph outline (depending on the level of detail T.J. can sustain). Each paragraph should have 3-4 sentences in it. Extended citations form their own paragraphs. And I told him, all you gotta do is answer the question asked -- that's what a college-level essay is about.
If T.J. can be taught to outline properly, he should be able to dictate his essays to his mom (or to Dragonspeak, which he's trying to get a copy of). After all, he does know his stuff; he's just never been taught how to get it out of his head and onto the paper.
* * *
I enjoy helping kids with their schoolwork. Back in Days of Yore, the Doctor, the Lawyer, and the Preacher were among the only members of the community to have any higher education, so they would frequently help young people prepare for college. That's a vanishing tradition I'm afraid, but then, I always had an antiquarian streak in me.