Young girl painful first anal insertion. First, remember that anal sex can include lots of different activities, such as penetration with a penis or the use of fingers, tongues, or sex toys. Manual sex feels fine but anal sex really hurts me. Why does anal sex hurt so much? Sex isn’t suppose to hurt, but for some teens that is the painful reality. o2302. The better relaxed, lubricated, and aroused you are, the higher the chances of having pain free intercourse. Heavy bleeding during bowel movements or any bleeding from your anus when you’re not having a bowel Victims of forced anal testing told Human Rights Watch that they found the exams painful and degrading; some experienced them as a form of sexual violence. The Anal pain or pain with bowel movements that doesn’t go away within 1 to 2 days after sex. This pain is felt at the entrance to your vagina during initial penetration. Dear Alice, I have never had sex, but I have tried now twice with my boyfriend, and it has been incredibly painful. It also looks into the reasons why doctors recommend them and explores some of the possible outcomes.