How can I make anal sex less painful for me? We use lube but it always seems to hurt still.

sadisticgames:

Lube is always the first step. 

The next thing I would recommend would be investing in a plug set. 

Something like this.

https://www.extremerestraints.com/butt-plugs_1/anal-trainer-set_801.html

The multiple sizes allow you to gradually increase the width that you’ll be maintaining. 

The more time you spend plugged the more relaxed you’ll be with something in your ass.

I’ll go ahead and add this to the original post. 

https://enemasupply.com/products/rectal-dilator-set

I agree that these are good, but it does depend on your time commitment. 

I like the plugs because you can wear them around the house while cleaning or working. 

The dilator set I feel would work better if you can devote a period of time to either sitting or have a chastity belt or harness to hold it in place. 

To each their own of course.