Anal sex can be enjoyed even if it has been consistently uncomfortable in the past.

Sufficient desire alone does not necessarily guarantee pleasurable anal sex. Nor is an uncomfortable previous experience always the reason for a lack of interest in or desire for anal sex.
Chronic anal tension is the most common cause of anal discomfort during sex. Hemorrhoids and constipation are usually a sign of this condition. Tension can be relieved by touching the anus and becoming more familiar with it. An ideal time to explore the anal opening is while taking a shower or bath. Deep breathing also affects the anal muscles. Tensing the anus and the letting go in another way of learning to relax it. Anyone who enjoys masturbation might want to experiment with some form of anal stimulation