I would doubt that, since Kirk never really did anything inappropriate like that, especially with a crewmember. He always pushed Rand away, and was deeply embarrassed at his holiday flirtation with Noel. There is no reason for that bit of dialogue to have that context, outside or in-Universe, IMO.
I disagree as the context would be that Kirk would have a joke as an incredible ladies man in-universe even if it is grossly exaggerated and untrue compared to the serial monogamist he was in Starfleet. As we know from the Roddenberry novelization, the series is in-universe television and greatly distorted the reputation of the crew as well as their adventures.