What is the most comfortable, and most uncomfortable position you have ever experienced? Also what do you feel is the most painful, and least painful thing you have ever experienced? The most comfortable position I was in was being tied to a chair, and it was extremely tight, as I was having problems breathing, from my belly being squished. The most uncomfortable would be the time I was tied in a split position, as I cannot do the splits. The most painful? Same as the most uncomfortab;e. Least painful..., l;et's see........ I know....., A hogtie.