Pictures:

What 5 letter word becomes shorter when you add 2 letters to it?

The word 'short'.

988

What begins and ends with E but has only one letter?

Envelope.

950

What did the lawyer wear to work?

A lawsuit.

969

How do trash collectors learn their trade?

They pick things up as they go along.

973

What happened to the magician driving down the street?

He turned into a driveway.

966