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Dear How to Do It,
I’ve been in a monogamous relationship with my boyfriend for several years. We have a great relationship in every way, including our sex life (the best I’ve ever had!). But there’s something unusual about him I’ve never experienced with another man. And I have no idea how I can say this to him.
He has never once come inside of me. Like, ever. He can go for quite a long time (awesome!) and always makes sure that I cum first (more awesome!), but when he is close, the only way he ever gets off is by jerking off while watching porn that he pulls up on his phone. Almost every time he is finishing himself off, my mouth or hands are on the head of his dick and/or his balls (he’s not into having his ass touched at all) but he HAS to be vigorously jerking himself off while he comes. I know what it’s like to only be able to cum under certain circumstances—for years, the only way I could get off was by masturbating with my shower head—so I have never said a word about it to him. The watching porn part doesn’t bother me, and as long as we both end up satisfied, who cares, right?
However, we have started talking about marriage and having kids, and I can’t see myself ever being “creampied” ever again! Plus, to make babies, he kind of HAS to cum inside me. Also, I think it’s incredibly hot to be creampied and would LOVE to have his cum inside me. Any advice for bringing this up to him, and/or some tricks or tips to make it happen?
— Creamless Pie
Rich: Family planning is the perfect time to bring up this conversation. It’s entirely relevant. Maybe you feel selfish for your personal needs, so you might feel inclined to hedge, but the greater good requires framing the conversation in these terms: “When we have sex, you don’t come inside of me. That is pretty important for conception.”
Granted, it is possible to get pregnant from non-direct, artificial insemination. You could even get pregnant if somebody comes on your vulva.
Stoya: I mean, artificial insemination is really expensive and the “getting pregnant from someone coming on your vulva” or from semen in pre-ejaculate is pretty rare. If you know you want kids, you really want the semen right up there next to the cervix, so the little sperm can swim up the cervical opening and get into the uterus and find the egg and do their fetus thing.
Rich: And so, because of that, it’s a completely natural question: “So how are we going to do this and try for a baby? Because I’ve noticed that every single time you’ve ejaculated, that’s never happened. What do you propose?” That’s the kickoff to the conversation.
Stoya: As far as the mechanics of this, I’m wondering how vigorous this jerking off is and how tight the hand is—you know, is it “death grip syndrome”? I also wonder if the writer is able to receive vaginal penetration that vigorously, if there might be some wiggle room and some possibility for retraining.
Rich: Yes. The death grip syndrome, a.k.a. idiosyncratic masturbation style, which is a term coined by sex therapist Michael Perelman. So there are a lot of men who, to complete the act, need to masturbate. Ian Kerner writes about it in So Tell Me About the Last Time You Had Sex, and it is a documented thing and far from uncommon. What Kerner proposes is to “take a short masturbation break and/or masturbate with your nondominant hand—if you’re right-handed start masturbating with your left hand.”
What I wonder is just how much this stimulation is part of the partner’s life. Sometimes all it takes to recalibrate is to take a little bit of a break, and then you really want sex and you’re more sensitive to it, and more sensitive to different kinds of stimulation. But that’s something that he has to work on.
Stoya: One thing that some porn performers do when the penis is too long is to put their hand around the base, and jerk off that like inch and a half or whatever. So I’m wondering, is it possible for him to maybe jerk himself off vigorously, just the couple of inches at the base, while the head of his penis is in our writer’s vagina, and start accustoming himself to ejaculating in a vagina?
And I’m also wondering if there’s something psychological. Has he trained himself not to ejaculate inside his partner because he didn’t want kids for so long, and now needs to re-acclimate to his new reality, which is talking about marriage and kids? I think it’s worth bringing up, having a real big, serious talk about kids and gauging how comfortable he is with that becoming a reality.
Rich: Yes, and to piggyback on your kind of human Ohnut technique—it would require a lot of good timing and careful alignment, but there’s a possibility that he could masturbate as vigorously as he prefers to the point of no return and then she hops on, or he puts it in just at that moment where he’s ejaculating. Again, this involves good timing and it’s not going to be the easiest thing, but it’s not impossible. That’s an option to pursue as well.
What I get from this letter is that this particular habit, this particular practice, has not been discussed. It’s just the way that it is for them. So it’s going to really require talking about this. You can’t jerk yourself off to the point of no return and then stick it in the vagina without a discussion about like, “This is what we’re doing,” you know? I think it’s just important to not shame him, let him feel comfortable, let him know all of what was said in the beginning of the letter: that this is the best sex ever, so much of it really works for her, etc. But look, we have a little issue here.
I also want to reemphasize the fact that, yes, while talking about family planning makes this conversation extremely practical, don’t feel bad about bringing up the fact that you want to be creampied for the hotness of it all. Like, that’s OK, it’s great that you do, you don’t have to downplay your desires.
Stoya: She says, “I have never said a word about it to him.” I get the sense that she is hesitant to have a conversation about this, or to have a conversation about sexuality in general. So I think we should do the “how to work oneself up to saying the scary thing” tips as well: Pick your time wisely so no one’s hungry, angry, tired, or cold, so if something goes sideways, you have plenty of time left to go like, “Oh, we’ve miscommunicated. Let’s pause, let’s untangle this.” Or “Oh, I touched a nerve, so we have to deal with fallout.” You don’t want to have this conversation 45 minutes before you have to leave for dinner with your parents. That’s not a good time. Do you have tips for saying the scary thing?
Rich: Leading with love, leading with the positives, I think that’s always a good technique. What I find useful to hear and say is often like, “We’re going to be together no matter what, this isn’t make or break. This is just something I’ve been feeling, something I’ve been thinking about that I’d like to pick your brain about. It’s a particular interest of mine. Do you think it’s possible to talk about it?” Men and their penises are really, really sensitive, so it’s going to be useful to affirm and let him know that you know that this situation is in many ways not just tenable, but attractive. “Can we work something else in? Can we do this? Because the idea of you shooting your cum into me is really hot. Do you have any particular desire to allow me to live that? And by the way, we’re also thinking about kids, so what do you propose to do about that?” You know?
Stoya: Yeah.
Rich: I think it’s the packaging. I think every single issue here is totally valid, it’s about just packaging it to be heard.
Stoya: And presumably they’ve been in this relationship for several years, so I imagine she has some experience with difficult conversations on other topics that she can draw from to figure out exactly how she’s going to phrase things and what the best approach is.
Rich: That’s what it is—you have to be judicious and careful and compassionate. And if things get too fraught, then just ease off—say, “Let’s talk about this some other time.” Don’t give up, but sometimes people can only handle so much in a single sitting. Shame can really color things and men can be incredibly shameful about what their penises do and don’t do. So unfortunately, sometimes you have to treat them like babies. And it’s really annoying, but if you want to get stuff done, you have to work with them, unfortunately.
Stoya: It’s true, it’s true.
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