Sandy and I get together to trim nails about every 3 weeks. Usually I hold the dog: I sit down in a chair without arms, and pick him/her up like a lamb... one arm around the chest/front legs and other arm around the fanny. The dog then rests between my legs, while the feet dangle in the middle. We do use muzzles. From this position, Sandy sits on the ground and clips and/or dremels to her heart's content. Even our drama queens can be done this way. Of course, a yummy treat is the reward for cooperating. Maybe this approach would work with your boy.