I have my second date with a B-type woman tomorrow. She’s agreed to an adult relationship (intimate), but says she still feels a little uneasy, so tomorrow we’re going to Ginza for cake. (I found this shop through the earlier “Tokyo date...” question. I always read this Q&A site, so I found that really helpful and thought it might be a good idea.

If she says she’s feeling anxious, then as the other responders have suggested, maybe just have some cake and call it a day? And as Marika pointed out, are you thinking of going without protection because you can’t stay hard with a condom? Please make sure you use one. Don’t let her lick you all over, either. Instead of worrying about pregnancy, you should be worried about STIs. Actually…sorry to ask, but does your dick even work? It’s not just a matter of you passing something on—you could catch something from her. Don’t blindly trust people, either. Always stay cautious.

> She says she’s okay with an adult relationship (intimate), but still feels uneasy. I’m not really sure what she means. If she still feels uneasy, doesn’t that mean she isn’t actually okay with it yet? Does “okay with an adult relationship” mean she might be okay with it someday? If that’s the case, then there’s not much you can do. Go on the date assuming you’ll just have some cake and part ways that day. Pay close attention to her and see whether she’s truly comfortable or still feeling anxious. Please show enough consideration and emotional awareness to pick up on those things and put her at ease.

A person to avoid is the type of older man who says, “I can’t stay hard with a condom on,” and insists on going without one. Your circumstances aren’t my concern—take medication or whatever you need to do, and use a condom properly. Marika

An adult relationship with a Type B woman sounds exciting. For the first time, it’s best to stick to something fairly standard. I also go to hotel dessert buffets and afternoon teas quite often. Though I more often invite them to have cake together at the hotel…

Since this is a dating club, there are plenty of women who are open to an adult relationship (intimate). So don’t focus too much on looking forward to that—just enjoy this current “who knows where things will go” stage to the fullest. I personally like Type A women the most. For a Type A woman, something as simple as “having her come to my place” can be a major event. I enjoy seeing her get nervous and wonder, “Is this really okay?” And although I’ve decided not to make a move, it’s genuinely fun for me too, because it reminds me of how innocent I was back in school and when I had just started working. For your next date, don’t rush things—prioritize her feelings. If she still seems nervous, you might show some restraint and say: “You still seem a little nervous, so shall we save it for next time?” She may also be expecting an allowance for an adult date. So if you gave her 10,000 yen for transportation last time and spent two hours together, you could give her 20,000 yen this time and let her go home. She may think, “What a gentleman.” Take your time and enjoy the present moment. If you really need to satisfy your urges, it might be a good idea to make an offer to a Type D woman at the same time.

You mentioned that he’s in his 70s or older. I don’t know how old the woman is, but I do think he should show a little more composure. If he genuinely wants to treat her well, then for a second date with a woman who’s feeling anxious, it might be better to skip the adult relationship. That said, please still give her the allowance. Whether or not to take things further should be something you sense from the atmosphere between the two of you. Since you said you don’t want to encounter a person to avoid, here are some things I personally disliked: - Persistent deep kissing - Sucking on my nipples until they hurt - Dirty talk Like, “Feels good, right? Say you want more!” - Taking the condom off halfway through - Trying to do it over and over again Things I was happy to have done: - Being held gently - Having his arm around me as a pillow - Asking what positions I liked and then doing them - Giving me lots of compliments And various other things. P.S. Paper Airplane, So a massage is foreplay before foreplay! I read your comment thinking, “That makes sense.” I’ll also take Marika’s advice about using pleasantly scented oil and try my best to help her relax and feel good in a gentle way. Thank you! :)

If you have the patience, you can simply wait until the woman makes the first move. Since so many men pressure women, that alone could make you stand out in a meaningful way. And for a cautious woman, the impression made by the first intimate encounter is especially important. But there’s no need to lose your nerve. > “I’m feeling nervous…” Those words may actually be an opportunity. Because they probably mean she hasn’t yet met a man who made her feel comfortable—perhaps someone who went on too long, took too long to finish, wasn’t particularly pleasurable, or wanted intimacy every time. If you can give her a sense of comfort and trust the first time, she may end up thinking, far more than expected, “Wow, he’s actually great.” You also need to figure out whether she’s the type who wants to continue enjoying fun dates even after having an adult relationship (intimate), and whether that matches what you want. To be specific, this applies only to cautious women who have gone on at least three or four dinner dates with you: 1. Don’t spend too long on foreplay. 2. Stop when she says she’s finished. 3. Move on to penetration fairly quickly and finish inside her sooner rather than later. The key is to keep the sex from going on too long, while showing that you’re satisfied and making her feel validated, so she can relax her guard toward intimacy even a little. I imagine her wariness comes from having experienced the opposite of these three points many times. First, give her a positive experience the first time—sex that doesn’t last too long, with the man satisfied as well. That alone can earn you significant points, and gradual progress can help deepen the attraction between you. > Miseki-san, Wait, the questioner is in his seventies? I don’t know whether you’re a formidable senior in the field, but young papa-katsu women are happier to go on dates with older men. I simply can’t compete with that. “They’ll give me 40,000–50,000 yen just for dinner.” So if there’s a possibility that you might not be able to finish quickly, a dinner date may be the better option. Miseki-san, a massage is like the foreplay before foreplay, so turn off the lights and create a nice mood. Wearing a bathrobe, yukata, or loungewear, start from her back, then move around to the front and work your way up to her décolletage. It originally started because, when traveling, I would massage my wife and wait for the right moment when she was feeling relaxed enough to be intimate with me. I used to get massages every day, sometimes twice a day, so women appreciate it when you loosen up the areas that feel good to you. Apparently, everywhere I touch feels good to them—which makes sense, since I only touch the places that feel good to me.

Oh, is that my comment? Am I being a little self-conscious? (lol) If the person you care about is feeling uneasy, I think it would be best not to pressure her into anything tomorrow—just enjoy some cake and call it a night without staying too long. If possible, try to find out what’s making her anxious and take steps to help put her at ease. That would be an even better way to show your sincerity as a papa (a male supporter). Things will surely be dozens, even hundreds of times more enjoyable once you’ve grown closer, rather than acting on impulse while she’s still feeling anxious. I hope you have a wonderful date tomorrow—and, ultimately, a long-lasting relationship.