I’d like to try using a toy for external stimulation during sex, but how can I bring it up without making him uncomfortable? I’m worried he might be put off.

I’m Shingo Lee, a columnist. I think it’s best to just be honest about it. Some men have an oddly high level of pride and may mistakenly think, “Is it because my technique isn’t good enough?!” So I’d be considerate of that. If you say, “I want you to watch me make a naughty face while I use a toy,” I don’t think any man would turn you down.

Maezawa from the CEO’s office here. As a basic rule, wait until you’ve become fairly close. If you’ve met fewer than ten times, I feel it’s probably better not to bring it up yet. Of course, if you can tell what kind of person he is, it might be fine even from the first meeting. But most men want to hear: “I prefer the real thing.” You may be trying to be considerate by saying that, since you’re more of an outside-stimulation type and prefer the real thing internally. However, some men may feel as though they’re being rejected when a woman brings this up. So I think it would be better to steer the conversation toward toys naturally. If it comes across as though he was the one who brought up the subject, then you could say something like: “I’d like to try one.” The important thing is to make it seem as though the man started talking about toys. That said, some men may have no problem with it at all, so it would be good to figure out what kind of person he is.

I’m Nana Ayase♡ It should be okay after you’ve gone on a few dates, but if it’s the first time, they might be seriously put off, so it’s best not to (not with younger girls). I haven’t had anything with my older husband for years. I use this to comfort myself, so wouldn’t it be okay around the second meeting?

I’m Kamihikoki, a male member. There are two ways to look at it. Personally, I wouldn’t like it. Having her bring toys along, I mean. Going shopping for one together would still be okay. But there are also girls whose chemistry with me is good enough that we don’t need anything like that, so these days, I just can’t do it anymore. I still have a low-vibration vibrator made specifically for the clitoris that I bought before in an effort to overcome bad chemistry… I hope I never have to use it again… When is the right time to bring it up—early on, after we meet, or once we’ve been seeing each other for a while? If you say it early, does that mean the chemistry isn’t good? If you wait, does that mean things haven’t been good up until then? Either way, it’s awkward… Use it from the very beginning? That would be really uncomfortable too…