Even better, imagine if the "bourgeois scum/corrupt nobility" wore super fancy costumes (and even some historically accurate costumes from Ulysses and the nerds), which only makes it more "distressing" when their lovely clothes, jewels, and accessories are stripped off their pampered bodies to be distributed to the oppressed working class before punishing & fucking each of the spoiled aristocrats until they give up their wealth and privilege and agree to be her comrades. Imagine Jett with a monocle and a top hat while speaking with a terrible British or French accent.
The spoiled and snobby nobles would be shocked and appalled that a mere peasant has the audacity to manhandle members of the bourgeois, strip them of all their finery, and even giving each of their beautiful bourgeois booties a spanking while the others can only wait in anticipation! Oh the indignity! What other cruelties will this revolutionary inflict on them? Will she teasingly caress their breasts and nipples? Will she force them to go down on her? Will she force them to wear cruel chasity belts or humiliating butt plugs while they wait for their punishment? Will she-
Cassidy: Wow, it's almost like you bourgeois scum want to be punished for your crimes against the people.
Even "worse," what if Cassidy brought in Jean's crew to help "break the arrogant captain"
Captain Amber similarly enjoys "breaking" the pirate crew until they each promise to change their ways, become honest sailors, and join her crew. Historian Eva (who would be the Pirate Captain in this scenario) probably is the most if not one of the most defiant...until Captain Amber recruits a recently converted Golfer to help her "reform" the pampered Pirate Queen.
Historian Damon definitely knows all the best spots and ways to "play" Lawyer Ingrid and Golfer Desmond, and they're all too happy to be played by him, Cassidy, and Ulysses (especially since they're used to being doms). MP Cassidy meanwhile definitely shows Historian and Mathlete Ulysses how to play Entrepreneur Mark, Marksman Jett, Fencer Eva, and the others. Fencer Eva probably plays up being a super defiant heroine captured by evil villains until she turns into a moaning, happy mess.
MP's partners definitely act super bratty after watching their poor boyfriend get such a harsh "punishment" and not even being allowed to join in. If Entrepreneur Cassidy's not careful, they might even turn the tables on her.
Of course, Matchmaker Cassidy still whines and throws a tantrum like a brat even after Drag Racer Wolfgang tells her he did his best, so he decides to punish Cassidy too until she learns to be grateful.
Likewise, Lawyer Cassidy is thrilled at not only taking down another corrupt sexy businessman and his equally sexy associates, but also getting to administer justice herself. Imagine if she put Entrepreneur in a chastity cage after his first spanking, blindfolded him, and forced him to stand in the corner while she punished (and rewarded) his associates.
Imagine if Fencer Cassidy was initially "captured" by villains and their were-coyote and forced to watch the poor damsels be "deflowered" while loving every single minute of it before the brave knight breaks free and defeats the villains, or if the damsels were forced to watch her be "tortured" until the brave Sir Cassidy turns the tables on her captors
As she stares at her students' red booties and smug smiles, Historian Cassidy wonders if she needs to try a different approach.
Historian Cassidy: Alright class, whoever can answer these questions will get a very special reward from me. Imagine if she initially gave the bright student a piece of candy to make them pout before really rewarding them. Mathlete Cassidy and Debater Cassidy's "teachers" probably do something similar after paddling (and possibly fucking) the bad girls if they're still up for it.