Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. (It’s anonymous!)
Dear How to Do It,
My wife and I (cis male), both 43, have been together since high school and married for 15 years. We are the only sexual partner each other has ever had. Some years back, I realized that I had a fantasy developing of her getting with another man.
For a while, I felt ashamed of this and because of this, I kept it to myself. Then upon doing some research I realized this is not uncommon at all! A few years ago, after a couple of cocktails, I shared this fantasy with my wife. To my surprise, not only did she not judge me over it, the idea excited her too! She confided in me that she has long had a fantasy about being with other men, and/or multiple men. Ever since then, we’ve talked somewhat openly about this (usually with or after cocktails), but purely as a fantasy for both of us. My wife has said she has no plans to ever go through with anything like this.
I 100 percent respect her boundaries and know that the choice to go through with something like this has to be a decision that sits right with both of us. Because of this, I’ve put zero pressure on her over the idea of actually doing it, and we’ve had fun just discussing it openly from time to time.
But I actually do want to go through with it. I’ve never really gotten a solid answer from her as to why we always stop short of actually doing it. Some theories are that she is worried about what it would do to our relationship/family (we have three kids) or that I’d want to do something with another woman as a trade-off. I can assure you, having thought long and hard on this, I would not be jealous in the least bit, only incredibly excited were it to come to fruition. I also have absolutely zero desire to be with anyone other than her intimately.
How can I advance our dialogue here without coming off as pressuring her? I’m very interested in how we can evolve this fantasy into something that can be on a path closer to becoming a reality. It also might be time for me to accept in my own head that it isn’t going to happen, but I fear that given both of our strong interests in this, we both may regret it later if we don’t explore it further.
—Ready to Share
Dear Ready to Share,
At the moment, you’re doing it right. I advise you to keep at it. “My wife has said she has no plans to ever go through with it” (your words) is pretty definitive to me. Whys are nice to know but they aren’t necessary for honoring someone else’s autonomy and consent. You aren’t entitled to any explanation beyond, “No.” Attempting to negotiate that points you in the direction of pressure/coercion, and this is especially so because the sex you’re pushing for would only involve her directly. This is entirely her shot to call.
I don’t think you’d be a bad person for expressing the desire to realize your shared fantasy, but it seems like you already have your answer. Expanding the conversation could actually end up turning her off from sharing this fantasy with you at all, leaving you with absolutely no outlet for it. Still, wanting to eradicate ambiguity is understandable in the event that she doesn’t realize how serious you are.
It’s a risk, but if you attempt this you must tread lightly with something like, “I know you’ve said you don’t actually plan on going through with this, but I’d really like to make it happen if you’re interested.” And that’s it. Any further resistance from her must be respected if you are to maintain a peaceful relationship. I don’t really recommend saying that, even, but if you need to be told “no” one last time to get it absolutely out of your head, approaching the conversation that way (and with brevity) might be the way to do it. And who knows, she might surprise you.
—Rich Juzwiak
From: I Think My 15-Year Fantasy Might Be Borderline Creepy. (September 28th, 2022).
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Dear How to Do It,
I can’t stop fantasizing about having a dick and penetrating a partner. I like using a strap-on, but in my fantasy life, I can’t help but imagine myself as a cis man. I’m bi, femme, and probably not exactly a cis woman but close enough to identify that way out of convenience. These fantasies are sexually gratifying and kind of welcome, especially since they’ve helped me re-embrace fantasy life after some sexual trauma in the past. My question is: Are they within an existing category of kink? Or just reflective of some gender stuff I need to process more?
—Penis Envy
Dear Penis Envy,
I wasn’t able to find a particular word describing sexual fantasies of being the opposite gender, but I did see posts on Reddit from women and men describing these fantasies. Some question where they fit in the gender binary, others question whether they fit in the gender binary at all, and we might all question whether the gender binary has enough purpose to outweigh the harms it contributes to. Labels are absolutely great for easily finding other people we may match with, sexually speaking. They also constrain, confine, and cause a lot of consternation over which labels to apply to ourselves.
Whether you need to process gender stuff more is your decision. There’s so much in the world to process. You make your own choices about what takes priority. If this is weighing on you, or you’re curious, go for it. If you feel like you should, but aren’t inherently motivated, give yourself permission to think about anything else—meditate or watch some TV instead.
The first resource coming to mind is Fiona Giles’s brilliant 1997 anthology Dick for a Day. The premise was women writing about what they would do if they had, well, a dick for a day. Notable contributors include Germaine Greer and Pat Califia. The book might spark some thoughts, it might spark some great masturbation fantasies—or I’m hoping it’ll do both.
The next resource I’ll point you to is Kate Bornstein’s My New Gender Workbook. Like most workbooks, you’ll get the most out of it if you do the exercises. You’ll likely come out of the experience with a more detailed picture of your relationship to gender. (And you’ll definitely have the opportunity to read one of the best explanations of kyriarchy—a multi-dimensional system for understanding privilege—that I’ve encountered.)
Lastly, I’m wondering how realistic your strap-ons are, and if you might enjoy going shopping for a more lifelike cock—what happens if you lean into your desires in a directly sexual manner? The NY Toy Collective, who once gave me a sample (which means I have to disclose that but also can speak personally to the quality of their materials), makes a stroker shaped like a realistic penis for $59, that can also be used as a packer. Transthetics, which has several positive reviews, has a few ultra-realistic play options in the $200-300 range.
—Jessica Stoya
From: I Think My Fantasies Are Trying to Tell Me Something Deeper About Myself. (September 13th, 2022).
Dear How to Do It,
Yay! I finally realized my ultimate fantasy of being gangbanged—and now I have some follow-up questions.
I’m a 34-year-old woman who’s always been kinky but never thought I could have a gangbang cause safety, and then got stuck in a series of vanilla relationships that had zero room for anything interesting (my last ex wouldn’t even touch my butt!) and then just got stuck cause pandemic/excuses/whatever. I now live in a liberal European city that has tons of swingers clubs and finally bit the bullet and went. I had an amazing time! I banged an actual troupe of firemen—I kid you not, and they even gave me a ride home in their ambulance. It was my best life.
So now I’m sore and happy but wondering about aftercare and planning for the future. Are there creams or oils I can use on my battered bits? I’m sore and it feels a little out of balance down there, but nothing alarming. Everyone used condoms without needing to be told. We didn’t do anal, but I’d be into that next time—how should I prepare? Can I safely DP (a huge fantasy) in a context like that or should I save that for when it’s just me and two dudes I know and trust? I’m afraid that it looks hot but is actually the Olympics and probably not easy to do comfortably.
Also, I don’t want to be single forever—are there men who will want to marry a woman like me? Can they overcome the Madonna/whore complex? I want to be a wife and mother but this is also who I am, my perverted side has always been there and isn’t going anywhere. I’m ready to let her be free but scared too.
—Kiss Kiss Bang Bang
Dear KKBB,
I am so happy for you.
For your soreness, I reached out to Dr. Stacy De-Lin, associate medical director at Planned Parenthood of New York City. She steered you away from coconut oil, saying it “won’t do much and some folks may be allergic or sensitive.” She does have several recommendations: “If there are any raw areas of open skin, a ‘sitz bath,’ a warm bath with a small amount of epsom salts, can be enormously helpful by bringing blood flow to the area to relax the muscles and to help to promote wound healing. For treating swelling, a bag of frozen peas, with a towel between the peas and your sensitive vulva, can help. Ibuprofen can help to reduce pain and swelling too.“
De-Lin has some advice for during the act, as well: “Having vaginal irritation and swelling might be a sign that you’re not using enough lubricant during intercourse. Be generous with the lube for future encounters, and be sure to always listen to your body: if it starts to hurt, then stop.”
As for double penetration, I recommend a less rowdy setting than the center of a gangbang at a club. Ideally you encounter a pair of people who already know they enjoy focusing on a woman together, and have had some practice with double penetration. Maybe you know another woman who has been DP’d in your town who can give a recommendation? If that doesn’t happen soon enough for you, look for two who get along and aren’t squeamish about touching other people’s testicles. It’s easiest to do a sort of body sandwich, with you in the middle, on something flat and wider than the people involved. The person on the bottom, or the “anchor,” should be OK with being squished, and able to stay hard without a lot of thrusting. Once you’ve got both dicks inside you, and they find a rhythm, both should be able to thrust. The less you wiggle, the easier it’ll be for them to stay in place.
And not only are there men who will want to marry you, there are men who will absolutely get off on helping you arrange these kinds of sexual scenarios and cheer you through them. You might meet these guys at the sex club, through a dating app, or by happenstance while you’re doing other things. In the meantime, you might consider what kinds of relationship structures are interesting to you. Give these concepts a web search: swinging, female led relationships, cuckholdry, vixen/stag, and polyamory. If any of those appeal to you, you might focus your dating efforts in areas that attract people who also want that framework, which could be a different sex club or a fully clothed community munch. If you’re on an app, you can include what you’re after in your bio. Enjoy!
—J.S.
From: My Friends Say I’m “Beyond Ridiculous” for What I Just Did to My Boyfriend. Are They Right? (March 23rd, 2022).
More Sex Advice From Slate
’m a young woman in my early 20s, who has recently started talking to a man in his early 30s. The age gap has not really been a big issue, but there’s one thing I find to be off-putting. It’s his use of Snapchat. It seems so immature to me, even though I know it’s irrational to think of it like that. It’s not the only medium of communication we use, but it does seem to be the one he prefers. Unfortunately, I haven’t really used Snapchat significantly since I was in high school. Whenever we interact on the app, I feel like I’m in that teenage mindset again. This has led me to restart behaviors that I thought I had left behind.