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go for it and dont give yourself time to think about what could go wrong.
also a wise stoner once told me that if you keep putting it off today, your gonna find yourself with a bunch of empty yesterdays.
I usually just wait till I'm comfortable doing what I am doing, then when its second nature and I'm not ever really falling I step it up a notch. When I am out with people way better than me I always end up trying a bunch of crazy new rails and getting hurt though haha.
Another good one is "man is a pupil, pain is his teacher"
You could just remove your tampon, then take your ball out of your purse :P jj