I have repeatedly communicated to him that he is both free and welcome to speak to me in whichever degree of freedom he prefers.

[The "repeatedly" indicating that she is well aware of his hesitations to do so, but persists in her insistence.]

[Though the mentioning of Ben's stories gives her pause. She always listened to them. They had talked about some of her stories before as well, so this was nothing new either.]

Have you been able to sufficiently translate his meanings behind each of them?