In one of the first season episodes Kirk says he is married to the Enterprise, which was what Roddenberry originally intended. The Ellison version of “City on the Edge of Forever” makes it clear that the relationship with Edith Keeler was special, which came through in the broadcast episode also. But then a bunch of writers wanted the same thing.
Anyhow, don’t forget that Kirk had some fun times with the replica of his old girlfriend in “Shore Leave.” But I don’t think that counts.
True, but as you say, some of them are under some kind of mental or physical compulsion, and a few are with women he was either currently (Edith Keeler) or previously (Ruth) in a serious relationship with. And a couple of them were androids, although granted Kirk didn’t know that at the time.
Given 79 episodes total, smoochies in only 17 of them seems like a fairly low percentage for someone who’s supposed to be an inveterate ladies’ man. I wonder how Kirk’s ratio would compare to other TV action heroes of the day–Jim West or Napoleon Solo, for example.
Good catch! It might not have been a full on seduction, but kissing an android so well that it awakens womanly passions in her is definitely within the trope. Plus with that outfit, I think Andrea counts as a space babe. (I was misremembering the “kissing a female android to awaken her womanly passions” as having occurred in the Mudd android episode - or did he do it there as well?).
So, I think we have one solid example of the trope in the first season. Not nearly as prevalent as the trope would have it, but it did occur.
I had forgotten that, but terentiii already reminded me upthread 
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Kirk didn’t seduce any of the female androids in “I, Mudd,” probably because he knew in advance they were androids. (Chekov was certainly interested in them, though.)
He tried to mail Miranda Jones in “Is There In Truth No Beauty?” (I hate that episode! 
), but she saw through his BS immediately. (Couldn’t have been too difficult, since she was telepathic.)
Rayna in “Requiem for Methuselah” definitely had her womanly passions aroused, though I’ve always thought she was a genetic construct instead of a mechanical android.
Kirk had it so bad for Rayna that Spock had to mind meld with him and remove all the negative emotions associated with her.
Reminds me of that identity theft commercial from a long time ago: ‘My girl robot! Hee hee hee!’
Bugs Bunny and the robot bunny girl. “Heh. Mechanical.” Long pause. “So she’s mechanical!” and takes off chasing her.
The situation was already stressful, you didn’t need the landing party getting two tents!
Do you know what the penalty for puns is on Deneb IV?
Death by snu-snu.
Oh, BABY!!! 
Well, to be fair, she kissed him first.
She didn’t even ask. When you’re a robot, they just let you.
I beg to differ.
Okay, finished with Season Two. Gotta say, I have a vague memory of seeing the final scene of Assignment:Earth. While I was most impressed at the time with the IBM Selectric that could type what you spoke (leading me to hope that one day my typing speed would exceed ten wpm), Terri Garr qualifies me to submit an entry in the “Who Was Your Childhood Crush?” thread.
Since Spock’s Brain was what got me started on this binge, I gave it a miss, and proceeded directly to The Enterprise Incident. ISTM that the Romulan commander set the Romulan Women’s movement back two or three centuries with her antics (even though Romulan/Vulcan space nookie was a little tame by ST:TOS standards), and she might do well to just defect when the Enterprise drops her off at a Starbase.
Considering that she’ll probably be put to death if returned to Romulus and Remus, that’s sound advice.
“The Enterprise Incident” is a terrible episode. It was rewritten so many times, it bears little (if any) resemblance to the original story (which was based on the USS Pueblo incident), and it has holes big enough to slip a planet through.
Counselor Troi First Season
They actually started out the same way with Counselor Troi in the first season of the Next Generation. Marina Sirtis said she felt like “an intergalactic cheerleader” and was uncomfortable with the look. They toned it down fairly early on.
I read at some point that the budget for the original series was wretchedly low. I’m amazed that they were even able to do what they did manage to do. I think it is unfair to judge the original series in a modern context because the succeeding series not only had the original concept to work off of but also a ton more money. I think the original series was a landmark venture and probably before its time. If it had come out immediately following the moon landing instead of in 1967, it might have had more money and a longer run.
One thing I liked wasn’t in the episode but the Blish book. Kirk is questioning Starfleet’s plan to have him act crazy to run the Enterprise into Romulan space. He laments that if he did that enough, one day he might actually really go nuts and the crew would follow him blindly, figuring it’s just another secret mission.
If I were Kirk, I’d be more afraid of damaging my reputation as a career officer by being labeled a lunatic.
Starfleet wouldn’t come off too well either: “Why the hell was a man this unstable ever given command of a starship?”