Looked into it further, noticed that the reason crankmaster does not increase is likely because during these scenarios, even if triggered multiple times, handjob count stays at 1 for sexual experiences. Due to this, crankmaster can't increase like it can in the brothel outside of the brothel. Making it so that these increase the sexual experience counter for each occurance would fix this.
Handjob skill does not increase during handjob events:
"CATGIRL-WEREWOLF-HIRO-SPITROASTED-MUTUAL":
"CATGIRL-VICTORY-TOP-ORAL-HANDJOB":
"CATGIRL-DATE-BREASTS-HANDJOB":
"DULLAHAN-DATE-TEASE-TABLE":