I had been interested in anal for a while, but every time I tried to do it it was just too painful. So what I started to do was see how long it took to relax when I was taking a bath. The warm water helped, and a bath is relaxing anyway. This is the only way I can do it for now: I take a bath, finger my ass for a while, and then when I feel like I am ready, I get out, put lots of lube outside and inside, and then I have anal sex. I'm sure eventually it won't have to be such a long, drawn out thing for me, but for now that's the only thing that works. I've tried it without the bath first, but I always end up ripping my asshole a little so I don't particularly like that. Maybe you could try the bath thing..