Would he find comfort in a cuddle toy? I say this is as DD2 was really into her boob and snuggle overnight (we co-slept on and off for the first 2 years) and I recently found that when she has her teddy (that she shows no particular affection for during the day...in fact it is generally shoved in the drawer) for some reason at night it brings her comfort and she will, when i hand it to her, roll over and cuddle into it for the night.