This Christmas, I've made him an octopus.
It's really just a modified version of the snake I made last year. The head is like making a baby hat, instead of making a brim I tapered off until it closed. The tentacles (all 8!) are just small snake tails that I attached to the head with a tapestry needle and yarn. The eyes are felt. and sewed on. I stuffed the head and the tops of the tentacles with batting, but I left the bottoms empty so they are floppy.
Oliver might not appreciate handmade gifts filled with love until he's much older (I mean what kid isn't more interested in the AMAZING COOL THING that Santa brought?), but hopefully someday it will mean more. And in the meantime he can wear the snake as a wrap and give the octopus a cuddle.