Been with DP for a few months, so far we haven't done anything that adventurous but he has said a few times he'd like to try anal.
I've only done this once before, I was really young and we were both inexperienced. It hurt alot and didn't feel good at all, I've never wanted to try it again until now. I've just realised I don't even know if he's done it before!
What should we be doing to get it right? Lube? Positions?
Also worried about it being a bit gross afterwards... how messy is likely to get?
I'm prepared for it not to feel wonderful for me, but as long as its not painful and unpleasant I'm happy to try it with him.