1. Pain is one of my favorite characters from Naruto. He's he second Naruto character that I draw in chibi style. So let's start. At the beginning draw a circle for the head and other body guidelines. Then draw facial guidelines.
2. To dress up your chibi, draw his coat. It's similar to Kisame's coat, but not such wide. Sleeves should be slightly bent at the elbows.
When it's finished, draw headband. Notice, that it's wider in the middle. Now, try to correct shape of the head, and draw an ear.
OK. it's time to draw pain's eyes. Rinnegan (that type of eyes) is a bit complicated. Sketch to medium semicircles and then put three or four more inside them. Paint the smallest semicircle in black and that's it :)
Sketch the mouth just above the collar. It will be nice to draw Pain's "earrings" now. He has some in his ears and nose ant two just below his mouth.
I think this step was the hardest one.
The coat isn't finished yet. So draw wide stripe along the whole length of the coat. Then draw Akatsuki's cloud on the coat's front and another one on Pain's left sleeve. When it's done, draw his hands and legs.
So far you've drawn Pain's body, clothes and face. Great! But he cannot be bald ;) He has spiky shag and bit of hair protrudes from the back of the headband.
There's only one thing left to do. The village symbol. It's rather easy to draw (four scratched rectangles on the 'swollen' rectangle).
Now, you can erase all guidelines and any other unnecessary lines, add some colors and shadings.
Have fun! :)