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Male Chastity, Female Led Relationship
"We don't stop playing because we grow old. We grow old because we stop playing." (George Bernard Shaw) So, don't stop playing.
Threaten to out him for being cucked/caged/pantied/pegged/owned/tiny (whatever is true for you and would crush him the most to have known) to a professional rival of his who is a woman. Obviously, some occupations will make this more realistic than others to actually follow-through, but it's a great threat, one that will keep him on edge.
Currently locked (or retaining)
5 -10 days
Holy Trainer V3. Penis tube size "nub."
Clarity of power balance.