Anal sex- female. Hurts.

What might help also is to have your BF lube up your rectum also.
This helps a lot with our anal sex sessions.
Once he has been inside you for a bit have him scoop up some thick lube (we use Alberto VO5 hair dressing) with his index & middle fingers and put this inside you.
I find it a huge turn on to lube my wife's inner ass and it slides in so well after this treatment.
I have found that some women like a little lube, some like a lot and a few can do it with none at all.

 

Where it's been a while your anus has obviously closed up a little. At the same time you can see that he is bigger so obviously anticipate some kind of discomfort so tense up when he is about to penetrate.

I'd say relax, ask him not to penetrate all the way, lots of lube and take your time.:afro:

 

So any update do you handle it