He is so doom ridden. He manages to put a negative twist onto everything.
If I cook something I know he likes I get "Oh, no! Not this again." if its something new then he won't try it because he 'knows' he won't like it.
He won't play out in because the other dcs will be mean (they aren't, generally) but he doesn't want to stay in because he wants to play on his scooter, he can't play on his scooter away from other dcs because he will fall off (he never has).
He won't try new authors because he knows he won't like them but he won't re-read books because its boring.
He is having problems at school because he crys due to the work being too hard then when he has been persuaded to try he complains its too easy and boring. Any new experience is greeted with tears because he will be scared/won't be able to do it/everyone will be mean.
Familiar experience are greeted with a negative comment "I bet X won't be going/I bet it will rain/I bet you won't let us have ice-cream/I bet I won't be able to do X/Y/Z".
He is close to terrified about meeting new dcs as they will 'be mean'.
He has experience a little bit of low level bullying along the lines of a boy shouting "Oi" at him in school, a bigger boy who lives a few doors away telling him to get off the football pitch because he can't play with them but generally he has lots of lovely friends and goes on nice trips and is able to do his schoolwork well and can hold his own at sports.