>>280059178
Because that's part of the power dynamic.
He's a boy who "isn't manly enough" and is insecure about it.
He's submissive to women (until eventually he fucks them hard, which may be before or after they restrain him and make him squirt, or dress him up like a girl). They have him on a "punishment system" that he clearly enjoys.
This particular chapter they are kind of fucking with him, which is unusual at least to this extent.