I’m asking because I thought the answerers here might have some good ideas.

I’m Saito, a column writer♪ I’m completely against using condoms, but if she says no, I’ll use one (the only consequence is that there won’t be a next time), and I’ll still give her the allowance she asked for. How many men actually force themselves on a woman without a condom after she firmly says, “I don’t want that”? Isn’t that basically rape?

Maezawa from the Corporate Planning Office here as well. I’m afraid I agree with Mack-san, but I think it’s perfectly fine to be straightforward with men who won’t use protection: “I can’t do it unless you wear a condom.” That won’t hurt their feelings. (They’re probably used to hearing it by now.) But perhaps what you really want isn’t a way to say it without hurting him—you want to make sure a man who refuses to use protection does use it, and still receive your allowance, right? In that case, you first need to master some advanced techniques yourself. If you learn how to put on a condom without the other person noticing, he may think you were having sex without protection, only to realize afterward that it had somehow been put on. Apparently, there are women who can actually do this. It may be difficult, but that could be one option.

This is Joe, a column writer. I agree with Mac. If he refuses to put on a condom even though you asked him to, he’s already hurting you! You don’t need to show him any consideration at all. In that situation, just channel the late Okahachiro and say, “Want me to reach up your ass and make your back teeth rattle?” Problem solved, haha. Wishing you many wonderful encounters and a lasting relationship.