http://www.youtube.com/watch?v=Gg3xk...eature=related
http://www.youtube.com/watch?v=MpUww...eature=related
http://www.youtube.com/watch?v=6-d_c...eature=related
Here are several videos which will give you a good idea of stippling. Basically it is a free motion design that wanders or you can pretend as if you are drawing with your needle. The experts say don't come close to previous stitches, but it is really up to you. You usually use a darning foot, put feeds down, and guide fabric with your hands.
If you have a longarm or midarm you move the machine to do the wandering.