Which ever finger fits. You would not perforate, as pain would prevent you from going beyond your level of comfort. The idea is to dilate daily to prevent the stricture from reforming. Once it is there, you really do not want to be forcing anything in there. If you cannot get your smallest finger past the stricture and you are having symptoms, it is time to make another appointment. It is better for the doc to dilate again early than wait for it to become critical. At that time, you can discuss the possibility of home dilation to preserve your opening. If it is tight, you can expect some pain while dilating, but there is a limit and you need instruction.
Each case is different, and your doctor may feel that in your case periodic office dilations will eventually stay open. It all depends on the quality of the stricture. Plus, not all doctors are in favor of home maintenance. But, still worth discussing. My thought is the old proverb:
"an ounce of prevention is worth a pound of cure."
Jan
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