1. Experiment with self-pleasure. There is only one person who can determine if your anal experience is going to be pain-free: you. Share on Pinterest Using a water-based or silicone lubricant may make anal sex less painful. For most people, anal sex can be painful, especially when it is. But anal sex doesn't have to feel bad or weird or dirty or gross. "Anal sex should not be painful," O'Reilly says. "If you do decide to venture inside, you'll enter the anal canal, which is less than a few inches long and rich in. Is Pain During Anal Sex Normal? in this situation is be sheepish about having had anal sex in order to avoid any nonexistent embarrassment.