Q: "a skateboarder grinds a bench." Does this mean that "The skateboarder is performing a trick."?
A: yes

Q: "A child is wearing a red hat shaped like a hand." Does this mean that "A child has a red hand shaped hat."?
A: it is not possible to tell

Q: "A woman in tight, leather pants walks with a boy." Does this mean that "The boy is her son."?
A: it is not possible to tell

Q: "A little black boy with an orange tank top and shorts jumped to the sand below." Does this mean that "The boy is swinging on the swings."?
A:
no