I’m feeling conflicted because the papa who recently made me an offer keeps trying to put it in from behind. I don’t get many offers to begin with, so I’d like to stay on good terms with him, but I’m not sure what to do. How do you all handle someone like this? Is doing it from behind considered normal here?

I’m Meg, one of the female members. When I was younger, I had a Slovenian boyfriend. He was into anal, too. Personally, I sometimes enjoyed it, and sometimes I didn’t. The younger man I was seeing until last year also asked for it. He was large, and it hurt terribly even with lubricant, so I asked him to stop. I haven’t tried it with my current papa (a male supporter) yet, but I have a feeling he may be inclined that way too. Maybe I’m the type who attracts men who are into anal, haha. I’m not sure whether someone experienced can make it painless, though. If you’d like to take a peek into a slightly different world, you could give it a try. But if your attitude is, “No matter who it is, anal is absolutely off the table!” then I think it’s best not to. Either way, what matters is whether he properly listens to what you want.

I’m in Seattle. If you do it the usual way, it just hurts. You need plenty of lube and proper preparation. If you’re going to try it, charge an extra fee. I’ve tried putting it in from behind a few times, but it slips out right away and doesn’t feel good. I’m already bored with it and don’t want to do it anymore. Once you’ve tried it, you’ll probably realize that the front is best after all.

Maezawa from the CEO’s Office will answer as well. Thank you for your question. Anal sex isn’t considered normal here either. In fact, I think the only places where that would be considered normal are those where people with that particular interest gather. That said, just as in wider society, there are people with all kinds of preferences. Sometimes you may happen to meet a partner who is into that sort of thing. I think you simply happened to encounter someone like that. > I’d still like to stay on good terms with him. If you’ve already decided on your stance, the rest is simple. Try thinking about what you would do if this person were your romantic partner, with money having nothing to do with it. If you feel you could accommodate his wishes if he were your partner, you could try going along with them. Then, if you still decide it’s something you can’t do, you might explain that to him the next time you meet. If you would refuse even if he were your romantic partner, then I think it’s fine to refuse at this point. You may end up parting ways, but you don’t need to force yourself. Alternatively, it might be a case of “an eye for an eye”—you could try putting something in his anus, too (though I’m not sure what would be appropriate). If he enjoys it, you’ll know that’s one of his preferences (though in that case, you’d probably be expected to do the same thing every time afterward). If he dislikes it, perhaps he’ll understand how uncomfortable it makes you feel as well.

I’m Kazu, a male member. In most cases, someone inexperienced will need preparation, such as gradually loosening up, before doing it anally. A man who suddenly tries to do it without any preparation is simply an inconsiderate idiot. I say “in most cases” because apparently, if the man’s penis is small, there are occasionally women who can accept it smoothly without preparation. I can’t tell from your question exactly how he tried to enter from behind, but if he suddenly tried it without you asking for anal sex, he’s just an idiot. It would probably be difficult to continue seeing him while refusing to let him do it that way. Doing it anally isn’t something ordinary. It takes skill to have anal sex without hurting a woman.