Interesting question, bobby. Usually crying (the real sobbing kind) is a cathartic experience and in My view is usually accompanied by some sort of challenge that breaks down a barrier - usually physical combined with mental.

I have a couple of small penis humiliation guys that cry but it's usually not when I am being verbally mean, but instead when I explain how it's all going to be okay because I have other uses for them and I accept them the way they are - small penis and all. It's their trigger so to speak.

I don't look at crying in session as a negative thing. Quite the contrary and in My opinion it should be a cleansing relief not a punishment or a goal just for the sake of making it happen. Does that make sense?