Chastity and orgasm denial discussion

A submissive facing four months of locking without orgasm, with just monthly prostate milkings—what would you suggest from either a Dominant or sub perspective to make his experience as maddening as possible regarding the method and timing of teasing? Assuming two teasing sessions each week:

1. absolutely no teasing
2. twice weekly caged teasing,
3. first week: two times caged, second week: one caged and one uncaged (repeating this pattern thereafter),
4. two times a week, uncaged with endless edging,
5. two times a week, uncaged but super soft, super slow, and spaced out movement that never quite hits the edge