While my gut reaction tells me that “No, it is not possible to take tomboy humiliation too far”, I feel we must go into this question a little deeper before we can make a definitive statement on the matter.
If we presume a Christian perspective on morality looking at actions in a binary category of sin and non-sin, we can conclude very quickly that, since tomboy humiliation is not a sin, then we do not sin by doing it too much. An aristotelian view concerned with golden means and vices of excess will look at the question very differently, however. Certainly if every virtue lies between vices of excess then we must categorize both an excess of tomboyism or an excess of humiliation as vices. If we assume yet a third perspective, that of a platonic, pagan sort, we can see that tomboy humiliation is actually one of the most moral actions possible, as it brings the humiliator closer to being the most divine form of himself in a way that channels mastery, taste, knowledge, and dominance.
Of course this is looking at the question from a moral perspective. If we want a more pragmatic approach to the question then I believe Scurvy McMango’s hypothetical illustrates the potential problems of excessive indulgence rather well. He neglects, however, that his scenario only could possibly occur in an environment of Cybernihilism when tomboy humiliation is most necessary. Consider the following pasage:
Imagine having enough tomboys to start a softball team with. You could coach them all in how to play the girls’ version of baseball. And also go on dates with them individually and make them wear frilly dresses instead of their uniforms. . .
If every man had a softball team of tomboys to coach and make wear frilly dresses, he would never accomplish anything else.
Why the hell are we in a place where there are enough tomboys to start a softball team? Well because Cybernihilism is happening. Where are the white sharia patriarchs to control these women? Well of course it has to be you because you’re the one putting them in frilly dresses and dating them. We are not able to accomplish other things because we are engaged in total war against the Cyberdecline; the same thing we’d be doing otherwise. Except in this scenario there are more women involved.
Literally, there is no downside. It is the ultimate form of the ancient art of Thot Patrol.