get a new girlfriend that knows how to relax her sphincter. from my experience, women can either do it or not. you can't train them to.
Sure you can. You just explained how every girl can do it. They just need to relax, period. The women that don't like to do it are the ones who refuse to relax and get in to it. The sphincter is a muscle, obviously. If she relaxes and feels comfortable while you ease it in, any woman can be taught to enjoy it. Use WET lube, it's water-based and not sticky, like astroglide and K-Y.
Get her drunk also!