For the pillow case, I used his current case and cut the fabric a bit bigger.
Next, I sewed a hem for the opening, and then stitched down a length of velcro that covered the entire width of the opening.
Finally, with the inside facing out, I stitched the bottom and the long side closed. Then I just flipped it right-side out, put the pillow in, and closed the velcro.
For the small pillow, I just trimmed out my remaining fabric to a small rectangle shape. Again, with the inside facing out, I stitched around all edges, leaving just about a 1/2" hole for stuffing. I flipped the fabric right-side out and stuffed the pillow as full as possible.
Once it was completely stuffed, I just hand-stitched the hole closed.
Little Man loves the small pillow because he can stuff it anywhere to get comfortable, and he often uses it on the floor when watching TV. And it only took about 20 minutes total to complete!