On our second date, I invited her back to a room, and we went together. She told me that she hadn’t been intimate with anyone for six years—since her student days—and hadn’t even masturbated during that time.

It happens occasionally, doesn’t it? If there’s going to be a next time, you could either ask her to bring some or let her know that you’ll prepare it yourself. After five years in this lifestyle, I carry ZONE condoms and Lube Jelly (lubricant) with me. ZONE is a condom already coated with plenty of lubricant. From my past experience, I’ve met women who used lubricant themselves because they had difficulty getting wet. When I first offered an adult relationship to my current monthly partner, I placed some lubricant by the bedside myself. (We didn’t end up using it, though—bragging a little, lol.) I eventually parted ways with women who used lubricant because they didn’t seem to enjoy adult relationships very much. In this lifestyle, I find it more enjoyable to be with women who genuinely like adult relationships and are responsive… For monthly arrangements that continue, I choose women who look refined but are sensual, enjoy adult relationships, are sensitive, and feel tight. When she starts dripping onto my face during 69, I get excited, lol.

I’m not sure whether you’ll be seeing this woman a second time, but there are also lubricants that come in packages about the same size as condom packages, so you might want to try buying one of those. Shimaru Lotion https://www.amazon.co.jp/dp/B096KD3HQJ Pepe Lotion Massage Jelly 5ml, LAVALAVA, Omega-3, Classic Normal—3-Type Set https://www.amazon.co.jp/dp/B08PF9S1WR If a slightly larger package is okay: Super Premium Coco Lotion Energy 5ml https://www.amazon.co.jp/dp/B01EWKG1YW Honey Drops 20ml https://www.amazon.co.jp/dp/B01MA6S32P/ When you say ordering online would be difficult, is the issue where it would be delivered? With Amazon, you can specify a convenience store near your meeting place and pick it up there before heading to meet her. If there’s an Amazon Hub Locker nearby, you can also have it delivered there. If the problem is payment, you could buy an Amazon gift card and use that to pay. If you really want to buy it in person, you can check the adult section at Don Quijote. Drugstores such as Matsumoto Kiyoshi also carry regular lubricants. (They probably don’t sell the pouch-type ones, so they’ll be a fairly sizable package.) They even have a Matsumoto Kiyoshi-brand lubricant, so that could work too. That said, this person who always writes only what they want to say first and then adds “This is my question” afterward so the post won’t be hidden—haven’t they mostly posted pretty lousy, slapdash questions up to now? I wonder if they’ve started making their writing sound more authentic...

I’m Shirousa, a new answer contributor. There are also condoms that come with plenty of lubricant, so using one of those would probably feel natural without having to ask permission. If you’re still worried, I recommend Lube Jelly sachets or Pepe Lotion Prologue. Since you only need to carry the condom and a packet of lubricant jelly rather than a bottle, they won’t take up much space. They’re meant to be single-use, but there’s quite a lot in each packet. Applying about a soybean-sized amount to the glans should be plenty, and apparently it shouldn’t feel cold to your partner. They may not even notice that you applied it. Of course, using too much can make things overly messy, so be careful not to leave any leftover on the bed. In any case, no one has ever objected. I hope you’re able to build a good relationship.

How compatible are you with this woman? Do you really need to continue seeing a club woman if you have to use lubricant with her? Since club arrangements are supposed to involve mutual interest, I feel it would be better to first explore ways to help her get aroused, ask for her advice, or find the right spots to caress before resorting to lubricant. Also, love hotels usually provide lubricant, so I think it would be better to ask her about it and try using it then.

Thanks for the heartwarming question. Once, when I was dating a virgin, we ultimately couldn’t go through with it the first time. On the second occasion, I had the same idea as you: while she was taking a shower, I bought some lubricant from the vending machine in the love hotel room. It cost ¥1,600—so expensive, lol. We managed to get things started successfully, and ended up doing it twice that day. We didn’t use lubricant the second time, and she seemed to be enjoying it, so I went at it pretty enthusiastically. But when I asked her afterward, she said it hadn’t hurt. I think the pain probably comes from being tense mentally. As for your question, I think it’s fine to ask about using lubricant on the day itself. She apologized the first time, right? From her perspective, she probably feels bad about it too. Letting her know that you’re making all sorts of preparations for the second time shows that you’re making an effort, which isn’t a bad thing. However, it may not ease her anxiety about whether she’ll be able to do it properly—instead, your preparations and thoughtfulness might feel like pressure. You don’t necessarily have to say, “It’s okay, you don’t have to force yourself; let’s take it slowly,” but I think you should approach things with that kind of attitude. To be honest, she probably won’t refuse. Still, when bringing it up that day, it’s better to focus first on easing her anxiety by saying something like, “Would it be okay if we tried using this? If it hurts at all, I’ll stop right away.” You’re an experienced adult, so you shouldn’t be flustered. Take the lead properly. This is actually pretty important(^^) There are all kinds of lubricants, but you don’t need anything fancy—something standard like Pèpè is perfectly fine. It’s not like you’re going to have a conversation about which one feels more slippery, lol. The main thing is to avoid any mishaps. A regular product that many people have used successfully is fine. But warm it up a little beforehand. At room temperature, it can feel cold and make her go, “Eek, lol,” for a moment. Before she showers, fill a washbasin with hot water at the highest temperature and soak the container in it. If you take it out after she’s finished showering and dried herself off, it should be just right. Wishing you the best of luck. Taro