Sorry - Forgot to respond to your last post, too. I think with love, patience, a whole lotta foreplay and good lube (I'm talking good, not KY - "Slippery Stuff" was a good old favorite that never dries out and is tasteless. Not sure if they've come out with anything newer and better since I discovered that years ago), you can work through the size issue.
I understand why she might not want penetration every time, especially if it is painful. But, if I were her, I'd prefer that you initiate and let me tell you if it's not the right time.
Recognize the orange cones (like the size issue), identify the solution, and then look beyond it. Don't let that stuff turn into a wall of fear.
