I used to hate his weekly milkings, so much work, just for some relief. But it has become a lot easier since I reduced his milkings to once every month or less.
Now I just have to tie him down, his cock hanging free. I take off his chastity device and wait. As soon as his cock has unfolded itself a bit from the long stay in the tight tube, he starts drooling cum. And once the first pressure is gone, each simple touch will make him drool a lot more. I can go on for as long as I like, and then just shrink his cock with an ice pack to lock it up again. No chance of an unintended orgasm, no pleasure for him, and a desperately crying slave for me; what more could any girl want?