Yep, time for a major toenail trim! My mom has an African Grey that I grew up with from the age of 10, and when I was a teenager, especially after I could drive, I would take her everywhere with me, and that's how we gauged when she was due for a trim, when her nails hurt my arms! It was really bad in the summer when I'd have a tank top on, my shoulders and arms would have long scratches all over them! My step father does her nails with a Dremel himself, I used to do it prior. She's such a good girl! But if you're not familiar with doing it with a Dremel (or clippers for that matter) then you need either a good, experienced avian vet or possibly a breeder/groomer to do it. The avian vet is usually the best way to go. As soon as you get it done your macaw's nails should be nice and dull, rounded off, and you shouldn't need sleeves or anything, as his nails shouldn't hurt you at all.
It's also a really good idea to get all birds, but especially large birds, some perches made for nail filing. They make all kinds, all of my birds have one in their cages, my Senegal parrot has the largest one, it's a cement perch specially made for grinding their nails down. His nails grow quickly and for some reason they go right into a really sharp point, like a dagger. If he didn't have that perch in his cage I'd have to have him to the vet once a month for a trimming, that's how fast his grow. So the perches save me a fortune. All pet shops, bird shops, bird fairs, etc. sell multiple types, sizes, colors, etc. I always put the trimming perch as the perch they have to use to either eat at their bowls or they have to use to get a treat I hung up at the end of it, like a treat stick or something that takes time for them to eat.
"Dance like nobody's watching..."
The shirt normally Kris me from looking like a self harm addict ROFL. 
