My boyfriend and I recently started doing.....you know the butt stuff. It just started with like while having regular sex he'd put his finger in occasionally and that felt nice until he asked if he could put his penis in there, so in my head I was sure what can go wrong. Oh honey I was very very wrong. It hurt so much, it felt like my virginity was being taken again. And then we tried it again the next day, and at times it felt good then it'd start hurting again... so is there anyone out there whose done anal who knows how to maybe make it feel better. When it didn't hurt it actually feels pretty damn good, but like what can I do for the pain? Does it go away after a while? We do use lube.....and loads of it.