Anal sex is not painful, anal sex is fun and more sensual if done properly and with the help of lubricants. Hemorrhoids are a very common cause of rectal pain. The man needs to be a fountain of tenderness, self contention and common. Condoms--over the penis or toy--can also make entry easier. That lube may well need to be reapplied halfway through. This is known as thrombosis.
With a woman, clitoral stimulation at the same time is great, but be gentle and make sure she's nice and comfortable first.
What Causes Rectal Pain?
Getting comfortable with anal penetration solo can make the experience a lot more pleasurable when you eventually do it with a partner. Use condoms for health reasons but, importantly, so you can whip it off and do oral or whatever on a clean penis …. If it hurts, you're not doing it right. Almost half of abscesses around the anus develop into fistulas, or small tunnels that connect the infected gland to an opening in the anus skin. It is -- at first.