Wife (F40) wants anal but it hurts

The first time I tried to fuck my wife up the ass, I was rough and she said it hurt. I didn't even get the tip in.

I've fucked other women in the ass before I know it hurts but the pleasure takes over. Pleasure and pain. And eventually I get to slam their ass hard and give her an anal creampie.

Last week, during a dirty weekend, my wife was super horny and begged me to try her ass again. I fuck her pussy. Pull out my cock and rub it against her asshole. I stick it into her pussy again. I do this over and over. This is driving her crazy cock and pussy both wet and juicy. She squirming her asshole onto my cock. The tip pushes into her ass. We pause. She holds for 5 seconds, and then tells me to withdraw.

We do this all night until I just cum on her ass and pussy.

I want to fuck her hard. It will happen over time. But I'm happy with the progress