How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It, 

I’m an olderish straight man in a serious relationship with a woman about nine years younger, with an overall fantastic sex life. Last year, we broke up for a few months while we sorted out whether I wanted to have more kids or not. That is settled, we are back together, happy, and a kid is on the way.

During our breakup, I slept with quite a few women. My girlfriend knows the broad strokes, but doesn’t want details. No problem there—I respond honestly to any questions she has and keep my mouth shut about the rest. But here’s the thing: One of these women was able to make me cum from oral! Like a lot of guys, this happens only rarely—so much so that I usually tell partners something like, “Don’t worry, it feels great, I just don’t finish from blow jobs.” This woman’s technique requires no high-level skills or anatomy, and it isn’t because of some other particularly attractive attribute she had. I came “normally” from any other kind of sex with her, but her oral really got to me. My problem is about how, or if ever, to tell my girlfriend about a technique this other woman did to me.

I would love to walk my girlfriend through this technique, which again is not wildly demanding (if anything, it’s way less deep throating!), but I’m worried that if I do, it could set off a jealousy spiral. If nothing else, any time I came from this technique, I suspect she’d have a flash of thinking about me with someone else while we were broken up, which would, well, suck. On the other hand, she has said in the past that she would love to make me cum with her mouth.

I suppose one option would be to present it as something I saw in porn or received during a sex party (she’s not jealous when we are having sex with others together). I, however, don’t generally lie. I’m not good at it, and I deeply respect her interrogation techniques, which she literally does professionally as an attorney. Do I tell her, hoping that the tinges of jealousy fade over the years, but the oral orgasms keep cumming forever? Or just keep this to myself?

—Pandora’s Orals

Dear Pandora’s Orals,

I’m curious why you’re putting so much emphasis on how simple and easy you perceive this woman’s oral sex technique to be, and where that certainty is coming from. You mention having a girlfriend and having sex with several women while the two of you were on a break, but you don’t say anything that indicates you’ve ever performed fellatio. I can tell you, based on a significant amount of personal experience, that fellatio and cunnilingus put different types of strain on different body parts, especially the mouth, jaw, and yes, throat. (Eating ass is much closer to eating pussy, but also requires slightly different motions and muscles.) Add the fact that people’s mouths may have varying dimensions, and areas of comfort and discomfort, and it’s really impossible to say for sure whether your girlfriend would have as easy a time with this particular maneuver as the woman who introduced you to it.

Your girlfriend is currently pregnant, and after giving birth, she’ll have further hormone shifts while caring for an infant. Along with jealousy, broaching a discussion about someone else’s sexual prowess may bring up fears that are more existential and therefore persistent. She’s almost certainly handling enough upheaval right now, and studies back up the age-old wisdom of avoiding stressing pregnant women out. Now is not the time to bring up unnecessary, emotionally combustible subjects. When your girlfriend has balanced back out, and is happy to return to sexual activity after birth, there’s a chance that life will present you (whether through her own experimentation, an actual encounter with porn, or a sex party hook-up) with a less fraught version of the oral variation you seek to recreate.

If you’d included more information about the stimulation in question, I might’ve been able to help you find a way to casually request such a sensation, but you didn’t, so I can’t assist with that. In the event you decide to propose this particular action at some point, steer clear of implications that it’s a walk in the park, though—if your girlfriend’s experience of it turns out to be more challenging, you’ll have set up a very tempting framework of comparison in which she is the lesser.

Dear How to Do It,

I am a male who was diagnosed with a serious health problem, one that may result in a sooner than normal death. My wife is younger than me and says she has a very low libido. Last year, we had sex only four times. How bad would it be if I looked for another woman to have sex with for the time I have left?

—Not Ready to Give Up Sex

Dear Not Ready,

If this diagnosis is new, take a moment to breathe and let your initial reactions pass. Serious health problems are (quite reasonably) a shock, and can be overwhelming. Sometimes people behave impulsively and regret it later. There’s also the fact that you may not die earlier than normal, and be left with the consequences of actions you wouldn’t have taken if you’d focused on the possibility of living as long as you once expected. The hospital or clinic you were diagnosed at can probably refer you to a support group or mental health worker who can help you understand some of the feelings you’re having right now, and an online search can also connect you to those sorts of resources.

I get the sense that you were already frustrated by the amount of sex you and your wife were having before you received your diagnosis. When you’re able to understand how your medical situation is affecting your emotions and desires, think through whether you want to stay in your marriage at all. Why did you get married? What do you appreciate about your marriage and love about your wife? Are you willing to risk losing all of that by engaging in infidelity, or by bringing up the possibility of opening up your relationship?

As for your actual question, it’d be pretty bad to try to cheat. Whether before or after your death, your wife will probably find out. You’ll either find yourself having a discussion that is more fraught than one where you suggest ethical non-monogamy due to the unethical nature of what your wife will have discovered, or leaving her to mourn both the loss of you and the knowledge that you weren’t who she thought you were.

Have Your Own Story to Share With How to Do It?

Readers often have great suggestions for our letter writers, occasionally disagree with a point our How to Do It writers make, or simply want to provide some additional advice. Each month, Jessica and Rich will be replying to some of these comments and suggestions from readers, which will be featured on the site for Slate Plus members. Write to us!

Dear How to Do It,

I work in a shop that sells adult toys and videos, and I am entitled to an employee discount. The problem is that friends always ask me to buy stuff for them so they can save money. I’ve been obliging them, but lately, I’ve begun to think it’s dishonest. Not to mention the joking comments I receive from my colleagues on the volume of stuff I purchase (i.e., “Where’s the orgy?”). Is what I’m doing acceptable, or is it time to put my foot down with my social circle?

—The Sale Is Over

Dear the Sale Is Over,

Unless your employee discount was accompanied by an explicit statement that you can use it on behalf of friends, yes, this is stealing. In addition to the moral issue, your mention of your colleague’s makes me wonder whether the way this is affecting your reputation is bothering you. There you have two reasons why this discount free-for-all is making you feel uncomfortable, each of which alone is enough cause to put your foot down.

—Jessica

More Advice From Slate

My ex was very addicted to porn and hardly ever climaxed with me. He would masturbate downstairs and leave me upstairs waiting for him. He wanted to see other women online instead of carrying out his fantasies with me.

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