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RE: The time I helped my friend lose his virginity....... and inadvertently turned him into a misogynist.
I don't know if doing it for the first time can flip a personality drastically like that unless some of that person was there to begin with. Maybe he had a hidden low view of women or even himself. By having sex for the first time it gave him an outlet to feel superior than someone else. By seeking out women he thought were loose he got a sense of being powerful which boosted his self esteem. I wouldn't blame yourself. You weren't the cause of his change in any way.
I suspect his first time should have probably been with a woman that was a little bit more conservative than Carolyn. It might have been better if they had dated 5 or 6 times before they had sex instead of having sex within a few hours of meeting.
That was the part of it that made me wonder. You're right though.......... he probably had something inside of himself that was already incorrect.