In addition to Carol, Miramanee, and Deela, we can make a good case for Drusilla, the Roman slave girl from “Bread and Circuses.” We see them making out, then there’s your classic “lamp burning down” dissolve to show the passage of hours, then we see Kirk asleep in the same room. It’s not definitive, but the implication is clear.
It’s also a safe bet that he got laid by one or more Argelian women while on shore leave after “Wolf in the Fold,” given that Argelius is a hedonistic, sexually liberal culture. But we never met any of them on camera.
Women he probably slept with:
Areel Shaw – Described Kirk as “my dear old love,” suggesting they were closely involved for a time.
Janet Wallace – Another old flame who keeps track of how long it’s been since they broke up, so it must’ve been pretty serious.
Janice Lester – She and Kirk were together for a year, according to her.
Women he kissed but definitely didn’t sleep with:
Eve McHuron – She tried to seduce him but couldn’t go through with it.
Janice Rand – The evil Kirk’s rape attempt didn’t get past first base, and the intact Kirk was too much of a professional to even let himself look at her legs.
Andrea – Doesn’t go beyond kissing because she’s “not programmed for [him].”
Helen Noel – People often think they were an item, but that was an illusion planted by the neural neutralizer. In reality, they only flirted and danced at the Christmas party, and the brainwashed Kirk kissed her briefly before coming to his senses.
Sylvia – He tries to seduce her to gain an advantage, but she catches on before he gets past first base.
Marlena – He simply doesn’t have time. The only gap in their scenes together is the act break after Spock warns Kirk he’s been ordered to kill him, and when we come back, Marlena’s still in uniform and reacting to that event. So there’s no opportunity for sex.
Nona – They’re definitely headed that way, but it’s scuttled by a case of mugatus interruptus.
Shahna – Ditto, except this time it’s Galtus interruptus.
Miranda Jones – His seduction bombed totally.
Uhura – They were forced to make out by the Platonians, and Kirk regained control of himself before it could go further.
Marta – She interrupted their makeout by attempting, err, premature evisceration.
Martia (from ST VI) – They only kissed once and then she left.
Uncertain cases:
Lenore Karidian – They fell into an embrace at the fade-out and we didn’t see either of them again for some time. But he was just using her to get to her father, so the question is, how far would he take it?
Ruth – With the fantasy version, probably yes, eventually. But the real Ruth was a memory from his Academy days, yet she was played by a 32-year-old actress. So she would’ve been an “older woman.” Was she his Mrs. Robinson, or just someone he worshipped from afar?
Edith Keeler – She was the love of his life, but would a “Sister” Edith from 1930 have been willing to have sex before marriage? The Crucible trilogy by David R. George says yes, and it’s true that sexual values in that era were probably more flexible than we assume (and more liberal than later in the '50s, say), but it’s hard to be sure.
Kelinda – Very probably not; they still seemed to be at first base when interrupted by Rojan. But there was a cutaway, so it’s theoretically possible they could’ve gone all the way, gotten dressed again, and started over again with the kissing.
Anne Mulhall – If it did happen, it was while their bodies were in use by other minds, so it wouldn’t really count anyway.
Elaan – Again, probably not, since they always seemed to be getting interrupted, but we can’t be sure how much time elapsed between scenes.
Odona – There’s an act break in which it might’ve happened, but it doesn’t seem too likely that they had time.
Rayna Kapec – They probably didn’t have the time or opportunity, since the whole whirlwind courtship takes less than four hours, but it can’t be definitively ruled out.
So the breakdown, for women appearing on camera:
Definite sexual intimacy: 2
Near-certain intimacy: 5
Indeterminate: 8
Kissing but definitely no sex: 12