I’m in my early 40s, and I really enjoy talking and having meals with this man. We get along very well, including physically, but there’s one thing that concerns me.

If it hurts, it’s not good for your body, so you should clearly tell him what you can’t do and ask whether you can continue the relationship without anal sex. Fuu likes anal sex, including standing from behind, so if that’s not possible, there’s no point in continuing. Neither of you should have to keep going while forcing yourselves to endure something. Be honest, and if either of you can’t accept that, unfortunately, it’s time to part ways.

I don’t know enough about the questioner or her big-dicked papa (a male supporter) to say whether this might offend him. But honestly, my reaction is: “Why not use your brain a little more?” If I may be so bold, today I’d like to present my very own “Ooh-La-La Strategy”: “Papa, yours is so big that Rie (not her real name) gets incredibly worked up. That’s why I get so tight—even though I’m usually so loose. But from behind, it hurts a little. If possible, could we do missionary instead—Seijo Ishii? No, I mean the missionary position! Ooh-la-la. Of course, cowgirl is more than welcome too! If Rie (not her real name) really gets serious, I’ll squeeze even tighter! Better be prepared. Oh, by the way, could you raise my allowance? Ooh-la-la.” No good?

Men are probably used to hearing this, so it’s perfectly fine to simply ask, “You’re quite well-endowed, so the regular rear-entry position might hurt a little. Would it be okay if we tried lying down?” I’m on the larger side too, and there’s a pretty good chance of causing discomfort from behind, but most women will say without hesitation, “Oh, this might hurt.” And I don’t think men are usually offended when someone points out that they’re large. If anything, they’re probably slightly pleased, thinking, “Well, I can’t help it—I’m big.” I’ve never taken it as a complaint. Personally, whenever I’m trying the rear-entry position with a woman for the first time, I always insert very slowly, move gently, and ask, “Does it hurt?”

Sex that you have to endure despite the pain is really tough. I think it’s best for both partners to tell each other when something hurts. Sometimes a partner’s teeth may graze me during oral, and if I just let it continue, it becomes painful, so I gently let him know. Most men probably get excited seeing a woman enjoying herself, so if you pretend to be enjoying it while enduring the pain, a man who doesn’t realize it’s an act may assume it feels good and keep doing the same thing. On the other hand, it’s also important to tell him when something feels good. I think that can lead to better sex. As for pain from behind, I’ve heard that regardless of the position, certain postures or angles can cause pain when there’s contact with the cervix. Even the position from behind can be angled in various ways, so why not experiment together? For example, if the woman keeps her upper body flat against the bed with her hips raised, and the man is half-standing upright, contact will be made with the lower, back side of the vagina. But if the woman raises her upper body as much as possible—on all fours, for example—and the man moves toward the bed, contact will be made with the upper, front side of the vagina. If she wants to raise her upper body even more, she can place her hands against a wall. I hope you’re able to have enjoyable sex.