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A previous slave set the standard I use to decide if I'm hurting a slut's tits enough. I had her hanging by her tits, only the tips of her toes touching the floor. I caned her tits hard, put the harshest clamps I had on the tips of her nipples, then used her tits as pincushions. After almost an hour of screaming, hysterical sobbing, and begging, she choked out "M-master, just cut my fucking tits off! I can't take it anymore!!!"
I pulled the whore up until her feet were flailing above the floor and left her for another hour.
If a slut doesn't beg you to cut her tits off so you can't torture them any more, you're not hurting them enough.