This is Mac, one of the answerers.

I’m traveling, so I’m afraid this answer will be rather brief m(_ _)m For me, looks have absolutely nothing to do with it—it’s all about〘technique〙♡ (lol) Some men can make me climax repeatedly with just their fingers, while others can send me over the edge again and again with incredible oral technique. And then there are those who do nothing but hurt me because their teeth keep getting in the way… (⑅•ᴗ•⑅)◜..°♡ I’m not really into handsome men either. It’s all about technique♡

This is a bit of a trick question, isn’t it? LOL. Men in particular love fantasy, so we tend to be biased toward believing in a convenient future. There are so many tempting “facts” dangling in front of us—like “you can’t have multiple orgasms without love” or “handsome guys are bad at sex”—that just looking at them is enough to fill you up（笑） I do think it’s probably true that vaginal orgasms are harder to achieve than clitoral ones, since so many women online discuss that very concern. But honestly, I think it depends on the person. Some women may have multiple orgasms during penetration even without particularly liking their partner, simply because they’re sexually compatible. Others are sensitive with anyone and can respond that way as long as their partner has at least a certain level of skill. I’ve experienced both recently. Neither of them was particularly into me, either（笑） With the same woman, I do think it’s true that she may find it easier to orgasm when she feels more secure or has developed feelings for her partner. So if you keep observing the same person over time, it might appear that way. But there’s a problem: even if you meet the same person repeatedly, you don’t know what’s really going on in her life. So the cause-and-effect relationship between her reactions and the reasons behind them may not be what you assume. Once, a woman suddenly became extremely affectionate, and I thought, “Maybe she’s finally fallen for me.” Then she suddenly stopped being able to meet me. When we finally saw each other again after a long time, her reactions had become noticeably muted. I was disappointed, thinking that just when we’d finally gotten somewhere, she must have been taken away by another rival. But later, I found out that her supervisor at work had pursued her and sexually assaulted her in what was essentially workplace harassment. Maybe she became affectionate because, when she was cornered and about to be assaulted, she wanted to believe in love. And maybe afterward, sex itself became unpleasant to her, which caused her muted reactions. I never confirmed that, though—I couldn’t exactly ask. But at the very least, there’s no doubt that both her affectionate behavior and her later lack of response had completely different causes from what I assumed at the time. All of Mac’s theories are wrong. It depends on the person and the circumstances. Still, they’re theories we want to believe, and honestly, believing them might not do any harm. If believing them motivates you to work toward earning someone’s love and gives you a reason to love the woman you’re with, perhaps it isn’t such a bad thing. It’s an undeniable fact that faith has supported humanity since before recorded history. In that sense, I’d like to wholeheartedly agree with Mac’s question and say, “Exactly!!” Taro

> A sense of security and a relationship of trust are necessary. Hmm… That feels a bit like writing, “When X² = 25, X = 5,” and getting it wrong. I think some people can orgasm from penetration even without feeling secure or having a relationship of trust. What do you think? This may also have something to do with whether they’ve experienced that before—in other words, whether they’ve been sexually “developed,” so to speak. I also think the brain plays a major role for women, so I can understand the point that a sense of security and trust are necessary. But if that’s the case, then the second hypothesis would actually work in reverse. If a handsome guy is, in her eyes, the most attractive man imaginable, it seems like reaching orgasm from penetration would become easy for her. Thinking about how many women used to faint at idol concerts during the Showa era, it was apparently enough just to have their idol nearby to make them faint. So if they were intimate with someone they genuinely considered handsome, it wouldn’t be surprising if things became incredibly intense. That said, for a woman who hasn’t been sexually “developed,” she might faint from the excitement, but whether she could actually climax would still be questionable. Besides, some women pretend to climax, so determining whether they really did is quite difficult. Apparently, even women whose bodies visibly tremble and jerk can say they’ve never actually climaxed. Maybe that’s a case of their bodies reacting involuntarily…?

This may not be the answer you were looking for, but Tsubaki here—someone who considers herself pretty open-minded about sex (lol). As you said, being with someone you feel safe with and have a trusting relationship with can affect you emotionally as well as physically, so the pleasure may feel more intense! ----- The following is more of a collection of my thoughts and experiences, but I’m not very good at putting them into words, so I’ll lay them out point by point. In the case of handsome guys: Girls come to them without them having to try very hard. In other words, they may have less motivation to improve their skills. But they can gain experience, so they might still get better? In the case of unattractive guys: They need to make an effort to please girls through conversation, thoughtfulness, and so on. In other words, they may have more motivation to improve their skills. But since women may not be drawn to them in the first place, they might not get the chance to put their knowledge into practice? This is just my personal impression, so please keep that in mind. ----- *Just a little addition* After reading Maezawa’s answer, I started thinking that if a handsome guy and an unattractive guy had the same skills and equipment, I might climax more easily with the handsome guy. Maybe it’s the ability to focus on the experience, or the excitement of it all. I might find myself thinking, “A handsome guy is losing himself over me♡” And putting looks aside, when it comes to that same kind of excitement: People my age ≪ Older men Poor ≪ Wealthy Company employees ≪ Business owners I’ve realized that I get pretty excited seeing someone above me in status lose himself during the experience (lol). When an executive at a certain publicly listed IT company licked my toes, I felt more thrilled than ever before in my life… ----- By the way, I prefer being pleased inside rather than around the clitoris, so I’m an immodest girl who begs, “Hurry up and give it to me♡” I’m looking forward to hearing what the other respondents think, too~!

Some women do find it easier to orgasm when they feel a sense of security and trust. That said, there are also women who have internal or multiple orgasms the first time they meet someone, so I think it really depends on the woman. But I do agree that handsome, popular guys are more likely not to be very skilled. Maybe it’s because women are drawn to them without them having to put in much effort, so they never really improve their skills in bed. Well, that turned into the bitterness of an unpopular guy, lol.

When you say that you need to feel comfortable with a man—or have a sense of security and trust— that includes the women I married and the woman I was engaged to, so it’s quite a large number. Most of those relationships are still ongoing, so speaking from the perspective of the women I’ve loved (and had sex with): Sex with someone you love is, in a sense, the best, and it’s always satisfying. Among them, there was one woman who took more than ten years to reach orgasm through stimulation, while another never did. There were also women with whom I had great chemistry from the moment we met. One woman would become aroused just from my fingers touching her, and her internal orgasms were even more intense than her clitoral orgasms—we could climax together. She was the greatest, truly one-of-a-kind woman I’ve ever been with. Was that because we loved each other, or simply because we were compatible? Since I’ve never met anyone else like her, I now believe it was compatibility. Before joining the club, I thought sex was only genuinely enjoyable when you were in a relationship with the other person. I was taught that I was wrong. Sex between lovers is always wonderful and fulfilling, but I’ve come to realize that it has nothing to do with whether you’re sexually compatible. That’s right—if there’s love, compatibility doesn’t really matter. Love transcends differences in compatibility. From that perspective, I think this statement is fairly accurate: “Clitoral orgasms are a matter of technique. If you touch someone the right way, she can climax even without an emotional connection—just like men can with their penises.” As for internal orgasms, unlike when I was younger, I can no longer seek out women who are compatible with me in that respect. With the anxiety of losing my erection or being unable to climax, it’s simply not possible. Having sex for an hour on my honeymoon feels like a distant dream now. Unlike when I was younger, the focus naturally shifts toward clitoral stimulation and internal orgasms before penetration. No—increasingly, that’s all I’m capable of. Also, many women feel that clitoral stimulation is more pleasurable than internal stimulation. In those cases, they can’t climax internally through caressing alone; they can only climax through clitoral stimulation, or simultaneous stimulation of both areas. I’ve never seen a woman who believes that have an internal orgasm with enough certainty to convince me. Women who have unmistakable internal orgasms—accompanied by deep, obvious moans—also feel more internally and deeply than through the clitoris, even during caressing, and climax internally several times before penetration. How broadly does this apply? Or is it simply my own preconceived notion? I’ve shared even some embarrassing details in the hope that they might be useful to someone. This was Paper Airplane, who has also experienced a major relationship crisis involving a request to prohibit marriage registration—possibly due to bigamy? > Marika Thank you for telling me about what happened and how she reacted afterward. > The real thing Please do check for yourself. I’m looking forward to seeing you. In an earlier answer, I suggested that we could meet even just for dinner so you could confirm in person, but judging from how this question is unfolding, that may not be an option this time?? Either way, it could be interesting. > The second hypothesis As for that, I wonder whether it’s considered true even for handsome men—or men who aren’t handsome. The reason is that compatibility matters, but you also have to genuinely want to make that particular person climax internally. Even for a handsome guy, he’ll probably end up seeing more women he isn’t especially motivated to please, so if he cuts corners, the woman will naturally feel that way. In that sense, I think Marika is being cherished by someone who truly wants to give her an internal orgasm.

I should warn you upfront that this will be quite explicit and very long. First, the two men who can make me orgasm from penetration are my younger friends-with-benefits partner in his 40s and my papa in his 60s. Both are lean, muscular athletes with huge penises about the size of a bottle of Sara Curl-Water. I’ve been seeing my younger FWB partner for about six years. He’s quite handsome, with the refined looks of a classic leading man from years ago. I’m not usually into handsome guys, but he’s kind, and I genuinely like him. We’ve been together a long time, so I feel comfortable and secure with him. It was because of his size and firmness that I discovered how good it feels for me deep inside. That’s how I learned to orgasm from penetration. Since we go for a long time, I’ll have several orgasms from penetration that feel like riding over small waves. Then, after he focuses on my clitoris and G-spot until I’m so sensitive I don’t even want to be touched anymore, he penetrates me once more and usually comes about a minute later. That final minute is so overwhelming that I can’t tell whether it’s painful or pleasurable anymore. I completely lose control and end up utterly exhausted. When I thought I’d never meet anyone that incredible again, the papa in his late 60s whom I met last year easily surpassed my FWB partner(笑) His length and girth are impressive, but his corona is especially remarkable. He was the first papa who taught me how good that can feel. Of course, he thrusts all the way in, so I can orgasm from penetration with him too. And since he’s my papa, I’m sure my feelings for him give me a bit of a bias. His oral skills and hands are wonderful too. After watching me climax several times, he gets a little more intense and comes one or two seconds after I do. So there’s none of that unpleasant feeling of “Don’t touch me!” afterward—I climax with him, and the happiness lingers. Now, what about handsome men I haven’t developed feelings for? I’ve never met a handsome man with a penis as large as either of these two, so honestly, I don’t know whether I could orgasm from penetration with someone I didn’t have feelings for, even if he were well-endowed. I might still be able to climax from oral sex without any emotional attachment. As for the handsome man introduced to me by Mac-san, let’s just say he was lacking in various ways. (Please don’t read this, okay?) And I’m not sure whether they’re synonymous with handsome men, but the type commonly called a “player” tends to be bad at sex. They seem to have the attitude that as long as they feel good, that’s all that matters. I used to like being on top, and that was always my position when I came. I think it was because my clitoris was stimulated while we were having intercourse. Now, with my FWB partner and my papa, I can orgasm purely from penetration. Of course, I still like being on top too. So, any truly well-endowed men out there who are confident they can help me test whether I can orgasm from penetration without having developed feelings first—please volunteer. (Although, one way or another, I’ll probably end up coming(笑)) Marika