The OP asks interesting questions. It seems, we are also expected to consider the questions from different perspectives.
AltanativeFTW:
Does anyone derive strong pleasure from male spankees being unable to live up to “boys don’t cry” in a story?
When you write "in a story." You're asking us to view ourselves as readers or observers. Can we take "strong pleasure" viewing another's pain? I think about a crowd gathering in the town square to witness a public whipping. The reactions can range from righteousness, to sympathy, to "glad it's not me", to orgasm.
AltanativeFTW:
having a female spanker tell her male victim that it’s okay to cry.
This is the point of view of the female spanker. It does emphasis that the power imbalance is so great, that "there is nothing he can do about it". That can be an act of additional cruelty or an act of mercy. She could be telling him to go ahead and cry, do whatever you have do to get through it. I won't think any less of you.
AltanativeFTW:
You’re going to cry no matter how hard you try to stop yourself
The view point of the male spankee. When this point is reached, does he even view himself as male. Male pride?? Can he even think? There may only be pain.
I'm thinking about this "in extremis". I prefer to step it back a notch. Leave the spankee with some skin in the game. I don't usually think about judicial spanking. My preference is F/M within a loving, caring, committed Consenual/nonconsent dynamic. Thinking about tears in that type of relationship is obviously controversial.
BTW kd, I think "Pride" is a great story.