The first woman I ever made an offer to.

That woman almost certainly has an STI, so the person asking should get tested. STIs don’t show up positive immediately. Unless you wait about two weeks after the possible exposure, you might test negative right away and mistakenly assume everything is fine. HIV in particular would be devastating. That’s why I take Tafero, which I bought from Osaka堂, every day as a preventive measure. There’s one girl who has sex without a condom with me and says she doesn’t do it with anyone else, but I can’t trust her 100 percent. I don’t take preventive medication for chlamydia or gonorrhea, since they can be cured with medicine if you catch them. Fuu probably likes doxy-PEP, so I’m sure he’ll write about that again. I’ve never encountered one myself, but apparently some HIV-positive people deliberately have unprotected sex to infect others and take them down with them, so you really need to be careful. This is unrelated, but apparently in some parts of the gay community, infecting someone with HIV is called “giving them positive seed,” and is treated like a kind of pseudo-pregnancy ritual. There’s apparently still plenty of bizarre stuff in the world. Don’t get drawn into it. By coincidence, the girl I have unprotected sex with was my lunchtime date today. For me, besides the psychological satisfaction, sex without a condom also feels physically better because I can directly feel her wet vagina. I pay for her STI tests and have her tested from time to time. If I want to keep having unprotected sex with her for years to come, I absolutely must not catch an STI from anyone else. That’s what I reminded myself again today. Having lots of girls to sleep with is nice, but one girl for unprotected sex is plenty. Her allowance is still 50,000 yen, but I’ll take good care of her. My current girl has little sexual experience, says she doesn’t have a boyfriend, and isn’t planning to find another papa (a male supporter). I took her to a doctor I know and confirmed that her STI tests were negative. Then, feeling worked up, I asked, “Since we both tested negative, would it be okay if I had sex with you without a condom?” She agreed, and we did. The next time we had sex, I said, “Thanks for the other day. I’ll use a condom again.” She replied, “If it feels better for you without one, I’m okay with it. After that, I went to the gynecologist and got prescribed the pill. If I catch an STI, I’ll get medicine and treat it. More than that, I want you to feel good.” The thought that I could meet a girl like this if I’m lucky makes me unable to stop looking for new offers—or rather, searching for a “winner.” Even after finding such a great match, I should just quit while I’m ahead, but the desire for an even bigger win keeps pulling me in. I guess that’s the thrill of gambling. “Sex” is also read as “saga”—human nature. Sex is simply human nature. I’d feel terrible if I had somehow passed an STI on to her. And since it’s possible she’s actually been lying and having sex with someone else, I sometimes take her for surprise STI tests. So far, she’s been negative every time, and at each test she grabs my arm and hugs me in public, saying, “I’m so happy you care about me.” She’s really a wonderful girl. I’ll continue to treat her well.

I’ve never had an experience like that. If you’re an adult man, wouldn’t it actually be kinder to stop her and say, “Wait a second”? Of course, women need to look after themselves, but I also think men need to be conscious of protecting themselves. If your partner was that unguarded on the very first meeting, I feel it would have been a moment to pause and think, “Is she okay?” rather than, “Does this happen often?” For both of you to feel safe and enjoy yourselves, I think the best approach is to check in with each other every time instead of leaving everything up to the other person.

It’s not frequent, but I think it does happen occasionally.

It probably depends on the person. Matching apps, papa-katsu (compensated dating in Japan), and street-based sex work are all booming. Love hotels in Kinshicho and Shibuya are fully booked even on weekdays from the middle of the day. There are probably girls who are doing it constantly and have gotten so used to it that sex without a condom has become the default. I once met an insurance saleswoman through papa-katsu who was like that. I guess she does it all the time to get people to sign policies. I couldn’t resist either, so we ended up doing it without a condom, lol. As for doxy-PEP, my go-to, Fuu, gets Vibramycin prescribed by a doctor she knows, so she always takes it whenever she has sex without a condom ^⁠_⁠^ Let’s manage the risks at our own responsibility. I’m waiting for HIV prevention medication to become a little cheaper ^⁠_⁠^

> Does this happen often? Almost never. > A woman I made an offer to for the first time. It’s possible she simply prefers first-timers and got carried away, or that she herself became extremely excited. In other words, she may be the type who’s okay with going without a condom if she likes someone, while insisting on using one with everyone else. Since we’re all human, I imagine many people would feel flattered by that. However, as Mac mentioned, you should be careful about STIs. She may do the same thing with other people she likes, not just you. Taking preventive medication beforehand might be worth considering. > She asked, “Is there an extra allowance if we don’t use a condom?” I think this is something she might ask when she isn’t actually satisfied with the allowance and wants a little more, but doesn’t think simply asking will get her an increase—so she wonders whether relaxing one of the terms might get her a bit more allowance. That said, most men would either be wary or lose interest when a woman brings up going without a condom herself. So I think women are better off not mentioning it until the man brings it up. > It was my first time hearing someone bring up going without a condom, so I was a little surprised. Somewhere along the line, I get the feeling there are women who do both sex work and papa-katsu (compensated dating in Japan) and preach that going without a condom costs more. Maybe women who hear that start bringing it up themselves. But I don’t think that’s what men are looking for in a partner. It also feels like both men and women are finding themselves in an increasingly chaotic world, with sex work and papa-katsu becoming more intertwined.

I’ve never had that kind of experience. I think part of the reason is that I always explain beforehand, to put them at ease, that I stay within common-sense boundaries—meaning I always use a condom. Of course, STIs and pregnancy are both frightening as well. The other day, I was matched with an especially lovely student. We had dinner, our terms matched, and she came back to my room with me. Then she suddenly asked, “Is there an extra allowance if we don’t use a condom?” I was speechless. Maybe she was simply a little too worldly for her age. Still, I told her that most men at dating clubs probably don’t prefer that, and that if a woman says she’s fine with it, they may be wary because she might also be doing it that way with other men, which increases the risk of STIs. She was exceptionally beautiful, both in face and figure, but I still haven’t arranged a second date with her. The only time I’ve ever had sex without a condom was when my wife and I were trying to conceive. Anyway, back to the topic. P.S. As Maezawa-san mentioned, I do think requests for an extra allowance often stem from dissatisfaction with the allowance. In the past, there have occasionally been cases where we agreed on an amount over dinner, went to a room, and then she said, “Other men give me this much, so could you pay a little more?” I generally try to accommodate what the woman wants, so I’d usually agree. But this was the first time someone brought up not using a condom, so it caught me a little off guard.

In papa-katsu (compensated dating in Japan), I’ve had unprotected sex at the first adult meeting at least a handful of times because the women wanted it. It was almost always cowgirl, too. I’d think, “Huh?” but my curiosity would outweigh my fear, so I’d just go along with it—that’s the pathetic side of being a man. *There were also women who preferred the missionary position, but only after telling me beforehand that they didn’t want to use a condom.*

They do exist—or rather, I get the impression there are quite a few. That said, if someone wants to go without protection from the very first meeting, I’d be 180% on guard. Because I’d assume she’s perfectly comfortable doing the same with other people too. If there isn’t yet any trust or established relationship, I think you should simply proceed with a condom. Hope this helps.