Physically, you should work on building up to the experience with your partner. If he has little or no knowledge of anal play, then you don't want to start with pegging but work up to that as the 'end goal'.
Begin with introducing a well-lubed finger during oral sex.๐
The truth is, he wants you to be firm with him. He might say he wants to climax but he craves you to deny it. This canโt be stressed too much. The male chastity lifestyle is thrilling, enjoyable and extremely rewarding for both you and your lover๐