I was gonna say "a tick" but then I realized it was backwards. They once were black but become red after sucking blood from your scalp.
Through the previously open window.
Scenario 1:
The pencil was used to prop the window open. The man was looking out the window, facing the pencil. The bullet came through the window, hit the pencil (breaking it), and hit the man in the head. The window fell closed.
Scenario 2:
The man was holding the window open by hand, with the pencil in his teeth. The bullet came through the window, hit the pencil (breaking it), and killing the man. The window fell closed and the pencil pieces scattered.
EDIT: added
Three strikes and you're out.