well i think they figured out that humiliation kink is at play. i believe the top goes for extremes one because that’s the ‘logical’ or ‘makes sense’ way to get the bottom humiliated. but actually it’s the humiliation that gets him spurred up! i think he essentially doesn’t really need to go for extreme plays. because just through the chapter we see crossdressing is enough and that’s not an extreme play.
i think that going forward, they’ll have to discover a middle ground. something that fuels his humiliation/degradation kink. and for the bottom, something that is embarrassing but he’s willing to commit (since they tried crossdressing, it’s tame but he’s uncomfortable by it) so yeah! a middle ground that fits both sides.
the way im analysing their kinks as well. this is actually so fun!