I strop on both sides of the leather. On a board, one side has the rough side out and the other has the smooth side out. Both are coated with green rouge. Another board has leather set up the same way and both sides are coated with white rouge. I rarely use both sides of either strop. I find myself stopping with the green rough side more often than not.

When stropping you should use only the weight of the blade during your strokes. Any more pressure than that and you risk losing the edge you acheived on your stones. There are some good links with instructions on stropping but I'm not where I can get to them now.
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DON'T BE SCARED
-Stretch