KIRK NO
KIRK YES
Going to boldly get it
The whole “Kirk is a lady’s man” thing is almost entirely the invention of fans.
What Kirk actually does is much more interesting: his instinctive response to being cornered, trapped, or otherwise helpless is to try to flirt his way out. He almost never actually sleeps with the targets of his flirtation–he just tries to get them flustered and off-balance.
It usually succeeds.