Obsidian is thinking of having me try *one* stroke of the cane on her, so that she knows what it feels like, and the thought of that makes me uncomfortable, too. On the other hand, I *would* want to practice first, if only so that I would not accidentally hurt her (beyond that which was intended, of course). While practicing would be uncomfortable, I would feel absolutely horrible if I really hurt Obsidian in anyway, and it is my understanding that the cane can do some real damage if not used correctly.
When Obsidian was learning, she practiced with a pillow and on the bed. Conveniently, we have a plaid bedspread, so that she could see where she hit against a straight line, so was able to see how straight her strokes were and could check to see if her was aim right. After she was comfortable with her aim, she tried some really *light* strokes on me to check for evenness.
I will tell you that, to my surprise, the light practice strokes DID hurt. Not nearly as much as the later real strokes, but I certainly did feel them. So, you would get a sense of the feeling from even light strokes.