Can you let an older man you don’t even like go down on you? I can’t.

Orgasming is connected to your emotions and controlled by your brain, so if you feel like you can’t, then you won’t. On the other hand, if you think you can, you probably will. It’s entirely up to you, but since you’re already doing this, you might as well enjoy the sex too. If you stubbornly refuse and keep assuming the worst, it doesn’t seem good for your mental health either. Personally, I feel like you’d be missing out. Getting an allowance, enjoying yourself, and having experiences you normally couldn’t—sounds pretty good to me...

I don’t climax from oral sex just because I like the person. With penetration, I think the chemistry and how much you like each other have a big impact, but with oral sex, technique—like the pressure and movement of the tongue—makes a bigger difference.

I’m dying over the mango, lol. I know an older mentor of mine who’s made cunnilingus his life’s work. Thanks to his instruction, I’ve improved quite a bit myself. He used to go on at length: Move the tip of your tongue very, very slowly and incredibly gently within a tiny 5mm-square area. Don’t retract the clitoral hood. And it’s not just about focusing on the clitoris, you know? Even with the same woman, her pleasure points can change from day to day. Figuring that out is the job of a cunnilingus expert. My mentor has a particular fetish: when he visits adult entertainment establishments, he doesn’t ejaculate. He simply performs cunnilingus until the woman climaxes. According to him, the odds of a sex worker climaxing are around 80%. There’s zero chance that a sex worker would fall for my mentor—a middle-aged man she’s meeting for the first time—so if the questioner happened to be with a truly skilled cunnilingus expert, the possibility of climaxing wouldn’t be zero. Apparently, there are even cunnilingus competitions.

I can’t help feeling there’s a hint of malice in the way you say “an older guy,” rather than simply “someone you don’t like.” So does that mean you could climax from oral sex with someone you don’t like, as long as he isn’t an older guy? This is actually an important point. It seems that, for women, mental imagery is more important than physical stimulation, so it probably depends on whether the person they’re with is someone they like or not. (Of course, there are exceptions, and I’m sure some women can still get aroused and climax with someone they don’t like.) Since I think it’s difficult for most people to do that with someone they don’t like, many probably share that view. However, even if the relationship started out as a paid arrangement, you can sometimes end up falling for the other person. In that case, whether he’s an older guy or not becomes irrelevant—if you like him, it’s okay. Also, I’ve heard that people who see their partner as money are suited to working in the sex industry. For someone like that, regardless of whether they actually climax, I imagine they may be able to do it for the money.

In my case, there are people I dislike, but there isn’t really anyone I particularly like. Basically, I like everyone I don’t dislike. Not in a “I wuv you so much♡” kind of way, though. What does it even mean to “like” someone? That’s what I’m more curious about than cunnilingus. If anything, when you keep having sex with someone, you gradually become accustomed to each other, until they feel like an extension of your own body. Then holding hands comes naturally, and it doesn’t make your heart race. It’s like touching a part of yourself. That’s why it becomes hard to tell the difference between climaxing through masturbation and being brought to climax by your partner. They become a part of you. It feels overwhelmingly better than masturbating, of course, but the sense of unity has to come first. It’s kind of like working together. Maybe the person asking this question isn’t unable to “like” someone so much as unable to accept the other person? A lot of women doing papa-katsu (compensated dating in Japan) probably don’t necessarily “like” their papas—they’re simply able to accept them. That’s why they can climax from cunnilingus. It’s almost like using the papa to masturbate. I think you should start by trying to free yourself from the urge to reject people. When I tell someone I’m seeing that I “like” them, it’s when I feel that sense of unity. I say it out loud, clearly. It isn’t always just physical, either. Sometimes I feel like our hearts have overlapped and connected, and that’s when I say “I like you.” To me, “I like you” is a blessing that means, “Congratulations—you’ve become a part of me. There are various benefits, so please enjoy them.” The physical side is easier to feel as a sense of unity. Feeling your hearts overlap doesn’t happen very often. Of course, there are also people who seem to overlap with you for a while, only for that feeling to disappear like a mirage—maybe it was just my own illusion, or maybe they were simply playing me.

Some women can orgasm that way, while others can’t. At swinger bars, some women climax from cunnilingus, while others do from fingering. Like Joe, I’m not really comfortable going down on a woman I’m not attracted to.

What a coincidence. I can’t lick the mangoes of women I’m not attracted to either. Despite appearances, I’m a bit of a germaphobe.