Anal sex is one of the more high-maintenance sex acts. Sabat suggests massaging your lower back, caressing your inner thighs, and then slowly working your way up to massage the entrance of your anus. Don't be embarrassed! It might also be a good time to reflect on your technique to see if anything you tried could be the cause of your discomfort, like not enough lube or not taking enough time to relax and get into the moment. Sabat suggests thinking of a fantasy, reading or listening to an erotic story, touching yourself, or any other self-love activities that can make you feel excited and comfortable to explore.