Today we're answering a question about whether anal sex hurts and if it's pleasurable for women! Kim and Amy sharing their own stories, shift. "Pleasurable anal sex is 90% preparation, and that includes getting mentally prepared. That's even truer if you've had uncomfortable or painful. However, it's entirely possible for large objects — like a fist, dildo, or penis — to fit inside of the rectum, and cause "an exquisitely pleasurable. Unfortunately, anal sex is often depicted as something that's painful and/or done for him. So it's no wonder many women are reluctant to try it!