I'm a man in my early 40s. I have never been able to give any woman an orgasm with my penis. I can give orgasms via oral every time but I feel inadequate because of my inability to get the job done. I've read everything I can find on the internet and still there's no magic. If it was just one or two women I would think it was not a big issue, but obviously, I am doing something wrong. How do I fix this?

Lots of women need more than penetration to orgasm. This isn't about you so much as it is about anatomy. I'm guessing a lot of your education around sex comes from porn and television, which, when untempered by reality-based sex education, can lead to some impossible standards for ourselves and others. While both types of video can be great for fantasy, escapism, and entertainment, neither is great for learning. I'd start with Scarleteen, even though you're very much an adult, to begin learning about the realities of bodies and sex.

If you're finding yourself feeling like you don't measure up in other areas of your life as well, or are having a hard time accepting that women's need for clitoral stimulation has nothing to do with you, your penis, or your thrusting technique, talking with a therapist might help. You can search for therapists who specialize in sexuality on directories like Psychology Today, or use the American Association of Sexuality Educators, Counselors, and Therapists' database.

Lastly, I suggest you take a moment to be proud of yourself for your oral skills. You clearly care about giving pleasure, and have put in work to acquire techniques. Not everyone manages to figure out how to give women orgasms at all.

Dear How to Do It,

I am a 65-year-old woman and my husband and I have been together for over 40 years. We have been lucky to have a fulfilling sex life as a key component in our relationship. I will soon have to have a double radical mastectomy and have chosen to "live flat." I am looking for resources and guidance on dealing with rebuilding our sex life and my general searches are helpful but not well detailed. Any ideas?

When it comes to women's health, subreddits can be a place to connect with people who are experiencing similar circumstances in order to swap information, experiences, and tips (I've linked to a thread about having sex after breast cancer). You do have to take things with a grain of salt -- these are strangers on the internet, with either no credentials or credentials that are difficult or impossible to verify. With a judicious application of critical thinking skills, these forums sometimes turn up useful tactics, and there's something to be said for the benefits of commiseration among peers. You can also ask your treatment team about whether there are support groups they can recommend.

Meanwhile, the Wake Forest National Cancer Institute is working on providing better sexual health support for breast cancer survivors, so at least things are moving in a better direction, though results from the study they're conducting about the best ways to deliver that information aren't anticipated until 2027. Your treatment team may also know of similar studies that you might be able to get into.

Mine the robust sex life you and your husband have already had for ideas about what might work well now. I'm guessing communication, connection, and acceptance will be on that list. Remember that sex includes a whole range of possibilities that can engage many different body parts, and stay open to new pleasures. As much as you might need to mourn, and give yourself patience and time around that, there's also an opportunity to discover what works for you now. Keep communication with your husband flowing, and collaborate on this project. And if you're feeling stuck, there are professionals out there who have experience working with cancer survivors and sexuality -- the Dana-Farber Cancer Institute offers one of such programs, and their blog may have some useful information for you.

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Dear How to Do It,

My wife and I, both in our mid-40s, have been married for nearly 20 years and sexually active a bit longer than that. While our intimate contact isn't super frequent, we truly enjoy each other's company both in and out of the bedroom. Amazingly, since our youngest and final child (of several) was born about four years ago, the passion behind our foreplay and lovemaking when we do get it on has gone through the roof. We have both always enjoyed pleasing the other and that has become even more intense, to the point of shedding some of our inhibitions. My wife has developed something of a penchant for blowjobs.

I have always enjoyed going down on her as well, and while she has to be in the right mood to let me do that, I can often bring her to orgasm with my mouth. Her most reliable and intense orgasms, however, are always from my "magic fingers" as she calls them. But, while she enjoys those things, what she really wants (she has told me) is to orgasm during penetrative sex. She has in the past, and she can still have "maybe" and "kind of" orgasms with me inside her, but it can be difficult and exhausting, and when it doesn't come, downright disappointing for her.

It is not an issue of sexual discomfort -- the sex feels really good for both of us. Our positions aren't many but have some variation, and it doesn't seem to make much difference whether I'm on top or she is, although she can more easily control what feels good when she's on me. We have tried some vibrating rings, and while she enjoys them, they don't get her any closer than without. I have also tried using my fingers while penetrating her, but she finds that too distracting. She enjoys me stimulating her nipples and breasts, but that doesn't really push her over. Neither of us is interested in any kind of anal play, digital or otherwise.

The timing of this change does seem to roughly coincide with the change in intensity of our lovemaking. Her period has also become usually infrequent, which we understand is a likely sign of perimenopause (if that makes any difference). So, what do you think? Is there something else we can try? Is there something else I can do as her partner? Could it be a head game, or even just a general decrease in penetrative stimulation for her?

Pregnancy and childbirth can have some profound effects on the mother's body, and therefore on their sexual response, as can perimenopause. This change your wife has experienced absolutely could be more mental -- what you call a head game -- or more physical. Regardless of the catalyst, though, your best bet is to experiment together and see what might work for her now.

You describe having tried variations during genital touching, but you don't mention much exploration of sensation outside of the "erogenous zones." Sometimes a slow burn, by which I mean taking a lot of time before touching someone's breasts and genitals, can set the person up for a much stronger orgasm later. A full body-mapping exercise, where you intentionally and methodically try various sensations on every body part, could turn up some new spots or ways to engage which might be fruitful. Barbara Carrellas' Urban Tantra or Annie Sprinkle and Beth Stephens' The Explorers' Guide to Planet Orgasm both include useful guides to body-mapping. And engaging in a lot of teasing before penetration -- where you stimulate arousal but don't cause an orgasm -- can lead to stronger orgasms as well.

You also might try a stronger vibrator, such as the Magic Wand, as vibrating cock rings tend to be fairly low-power. The Magic Wand's shape lends itself well to being used during penetration, too.

-- Jessica

I (65F) have been seeing a much younger man (37) for eight weeks. We agreed in the beginning it was just a sexual/casual thing, no strings. I told him my true age after our first time together, but in a subsequent text I made a typo and put 55. I never bothered to correct him.