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Dear Miss Information,
I am a woman in my early twenties and, frankly, I really love sex. I recently started dating someone who turned out to be quite sexually repressed. The other night we "hooked up" and had sex, and it was good but not great. He went down on me — he seemed to know what he was doing — and I came during sex, but he had some trouble staying in the game. It took him quite a long time to come. He claimed it was hard for him to enjoy sex fully because of the past sexual repression he experienced in a religious Korean family and community.
I want to know how to get past this. I can be a very giving person in bed, and I enjoy when I'm able to make someone extremely happy, but he doesn't seem very receptive to my attempts at learning what makes him tick. If anything, he seems uncomfortable and weirded out by the idea.
What should I do? Should I continue to push him to let me do things for him and to experiment? Or should I let him come around and wait until he says he feels completely comfortable? How do I help a sexually repressed person enjoy himself in bed?
— Not Sexually Repressed
For starters, if he is saying or implying "no," respect it as "no." His repression is between him and his god; unfortunately, there's nothing you do can help it. If you put on your conductor hat and insist he hop on the Naked Train to Pleasuretown, it'll almost definitely backfire. Instead of merely contending with the naysaying voices of priests/parents/friends while he's trying to get down, he'd also have to contend with feeling rushed or pressured, or, worse, of not having his boundaries respected. Those kinds of emotions would likely take him off the Train and put him staunchly on a Handcar to Celibacyville.
Giving him space to experiment is a good idea, but he has to want the change for himself before anything can improve. And, as you pointed out, it could be a lengthy process. Ask him what he wants. If he's open to boundary pushing, by all means, give it a shot. But if he's really so uncomfortable that he shies away from your attempts to woo him, this might be a long, frustrating road for you.