In Bread And Circuses we learn that bad guy du jour Proconsul Claudius Marcus owns slave Drusilla. For reasons that should be obvious, Claudius Marcus orders his slave to entertain Captain Kirk for a night. Kirk's reaction when he is first shoved into Marcus's quarters alone with Marcus's personal slave is to loudly protest TWICE that "It won't work!"
Drusilla tries to reassure Jim that the situation isn't an obvious setup (which it is) and she tries to seductively convince him that she is only his slave for the night, and therefore owes her loyalty only to him (which she doesn't), and furthermore she tells Kirk that she has been ordered to please him. Yeah, RIGHT!
Kirk doesn't bother to ask for the one thing that he really wants from this woman (his freedom) because he knows darn well that it's beyond her powers to grant that wish.
OBVIOUSLY Drusilla's true loyalty belongs to her master, Claudius Marcus, who just happens to be Kirk's enemy - and Kirk knows that. Kirk's no dummy. He knows better than to get too involved with this doll.
He lets her provide him with food and wine, and he allows that the food and wine is good. He kisses her a couple of times. That's as far as it went. There is no solid reason to believe that anything beyond that happened between them. To the contrary, we have good reason to believe that nothing much beyond that happened:
1) Kirk said from the start that "It wouldn't work!". He said it TWICE. He was quite emphatic.
2) There is no sign that any whoopee actually was whooped. The next day, Kirk was all alone, fully dressed, and in an apartment that was as neat as a pin. Kirk doesn't say or imply that any whoopee was whooped. There is no sign nor other solid physical reason to believe that Kirk did more than kiss Drusilla.
In any case, even if Kirk did horse around with her, it was a situation where he did not choose the woman for himself, he did not court her, he went to no effort to win her, and neither one of them had any choice about where else to be that night. She was never Kirk's girlfriend, and he certainly was not in love with her.
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