I have sex with a man I’ve met several times, and he tells me almost every time, “I’ll teach you what really feels good,” but it honestly doesn’t feel that way.

Maezawa from the CEO’s Office here. Thanks for your question. Everyone’s sharing some pretty incredible stories. What exactly are you trying to brag about here? (lol) > Men often tell me that we’re really compatible. From a man’s perspective, you’re probably a woman he doesn’t want to let go of because the fit is amazing and you’re also good at putting on an act. Normally, I’d say you should tell him that it hurts, but in this case, it seems he likes you partly because of that performance. So your choices are either to put up with it and keep seeing him, or end things. If you’re okay with the possibility of ending things, you could say something like: “I’ve recently been having trouble getting wet, and it’s been painful down there… Maybe you’re just too big for me? Would you mind using some lubricant for a while?” Then it would be fine to have him use lubricant.

I’m Kamihikōki, a male club member. In the club world, neither side feels able to voice their dissatisfaction. But you shouldn’t keep putting up with things. At the very least, let them know when something hurts.

I’m Flagmaker, a columnist. I’m actually writing a column for men right now about situations like this. It may not be published for a while, but I hope you’ll find it helpful. When there’s an allowance involved, women often feel unable to say anything, while men don’t notice. I think this happens quite often. In my case, they’ll openly say things like, “I’m not feeling well today,” or “It’s sore down there (or inside), so let’s take it easy.” Maybe it’s because my allowance is low（笑).

I’m Jasmine. There’s no such thing as a decent person who says, “You just haven’t experienced the real ○○.” They annoy me about as much as people who say, when I mention a food I dislike, “That’s only because you’ve never had truly good ○○.” If the allowance is good, why not just put up with it? Personally, if the intimacy was mediocre and their personality was awful, I’d probably end things.

I’m Kazu, a male member who believes it’s rare for an overconfident man to provide good sex. As Mac said, I don’t think being bad at sex is something you can fix. I’ll probably fade into the background after Riichi’s story, but I’ve also had an experience at a niche adult entertainment establishment where I was told, “I’ll teach you how pleasurable anal can be.” They put a finger inside my anus while I was nervously excited. It wasn’t pleasurable at all—I paid money to experience the uncomfortable sensation that I might need to poop. It was so unpleasant that I just wanted it to end quickly and wanted to go home. For a brief moment, I understood how women must feel. And since I was paying for it too, that made the whole thing even more miserable. Sometimes I wonder why women put up with being treated that way. But whenever I remember my own miserable experience at that establishment, it starts to make sense. Even though simply saying, “I don’t like this, so I’m leaving,” should bring things to an end, people sometimes make the strange choice to endure the situation and wait for it to pass. I’ve also had a gorgeous trans woman with a huge penis tell me, “I’ll teach you how pleasurable anal can be,” and nearly insert it. That time, I said, “I can’t!” before the head could fully enter. She gave up on penetrating me and instead brought me to orgasm with an incredible blowjob. Thanks to that, I didn’t have a bad taste in my mouth afterward. The trans woman with the huge penis was much more skilled than the niche establishment. In the end, I think truly skilled lovers are the ones who watch their partner’s reactions and prioritize their partner’s pleasure, at least for the moment, over their own desires. It doesn’t seem likely that I’ll ever discover the pleasure of being penetrated anally. Having experienced it firsthand, I have no intention of penetrating anyone who isn’t open to anal sex. > Mac Come on—ordinary people don’t have group sex involving a virgin or create something resembling a Magic Mirror bus! That said, I think those spectacularly awkward mishaps happen precisely because it’s an adult entertainment establishment. In papa-katsu (compensated dating in Japan), most women are perfectly normal, so I’ve never experienced anything like that.

Seattle. Overconfidence is embarrassing. If you don’t have any other source of financial support, bring it up carefully—maybe start with something like, “I bought some lotion and would like to use it.” Riichi, that made me laugh and cry. Mac and Kazu’s stories were funny too. I wonder if I have anything like that. A representative from my securities firm once told me that a friend of theirs worked as a dominatrix and asked if I wanted to give it a try, so I went to an SM club. They licked my eyeballs and ear holes. It was unbelievably disgusting—I felt like I was being tortured and just wanted it to end. Maybe I really was an M, since I put up with something so painful.