In fairness we have no idea if some of the aliens he's expressed an interest in even have a vagina...
As I've probably said before, I like the scene in a Star Trek novel where he attends an ambassadorial dinner being hosted on the Enterprise and attempts to chat up an attractive female amphibian delegate, only to be told that she's flattered but really isn't into mammals, and is far more interested in the piscine ambassador floating in a nearby tank. When she also notes that her species doesn't have intercourse (Which she finds a rather repellent notion), but spawns, with the male fertilising the egg cluster some later, even Kirk backs down.
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Ms. Spock should just be glad her captain is there, because you know she's Jim's second choice.
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As I've probably said before, I like the scene in a Star Trek novel where he attends an ambassadorial dinner being hosted on the Enterprise and attempts to chat up an attractive female amphibian delegate, only to be told that she's flattered but really isn't into mammals, and is far more interested in the piscine ambassador floating in a nearby tank. When she also notes that her species doesn't have intercourse (Which she finds a rather repellent notion), but spawns, with the male fertilising the egg cluster some later, even Kirk backs down.