Of course he gets it. He's probably the archetypal example of someone who has a lot of kinks that have been turned against him by various sadistic adversaries, and that's not even including a year spent being tortured by the Master. He's had to learn to get over it each time, and by far the best way has been to do something similar but pleasurable with someone he trusts.
"It's important to claim it back for yourself, to not let him win," he agrees seriously. "I'd really like to help you with that. Do you feel ready to try being tied up again? Let yourself lose control that much in the hands of someone you trust?"