How to Do It

I Think My Fantasies Are Trying to Tell Me Something Deeper About Myself

I might need to process this more.

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Photo illustration by Slate. Photo by Poike/iStock/Getty Images Plus.

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 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?

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—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.

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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.

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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.)

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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.

Dear How to Do It,

I’m a 45-year-old woman with an active and very enjoyable sex life with my (male) partner. I’m also a couple of years out from a 23-year-long, extremely psychologically abusive relationship with a man who, it turns out, has built his life around grooming his 18-24-year-old female students. (They don’t have to be his students if they have the right kind of father-based trauma, to be fair.)

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I’ve always enjoyed erotic films/porn and they’re effective for me, and I see no ethical issue as long as the performers are of age and treated right, and are enthusiastic in their consent. At this point, I am utterly disgusted and triggered by watching any porn with youth fetishization, power imbalances, and/or plots that revolve around any kind of deception or cheating. I would like to see female performers who are around my age, or at least full adults, to pair with the men I see, who often sport gray hairs. I’m willing to pay, because, of course, if it’s free, someone is getting exploited, and in the case of porn, it’s probably a teenage girl. I’ve found places that are not heteronormative and celebrate different types of bodies. But I haven’t found anything that is just regular, basic porn, but with women performers who are clearly not teenagers or very young women, and/or plots that don’t revolve around betrayal as their source of erotic tension. Can you recommend any sites?

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—Grown Ass Woman

Dear Grown,

I’m sorry you went through that relationship and glad to hear you’ve found a partner with whom you have what you describe as a very enjoyable sex life. I reached out to feminist and ethical porn maker Jennifer Lyon Bell of Blue Artichoke Films because her work immediately came to mind as likely to fit what you’re looking for.

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“While none of my performers were in their 40s at the time of shooting, several were in their mid-30s. I’m thinking especially of Sadie Lune (Adorn), Liandra Dahl aka Helen Betty Corday (Silver Shoes), and Kali Sudhra (Wild Card), all of whom are charismatic, beautiful, and extremely sexy,” Lyon Bell says. “So I think you would still like it. I enjoy seeing women who clearly are in touch with their own sexual desires and like asking for what they want, but still have a vulnerability and openness that make you feel like they are being very pleasantly surprised at how the sexual situation is playing out. The emotional realism of the sex is very important to me. I don’t think that ethical porn necessarily has to have a real-life feeling, but mine does because I like it that way.” She warns that “adorn does have a little bit of ‘switch-y’ power dynamic in a playful way, but mostly with Sadie in charge and with an intimate vibe!”

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Let’s talk about exploitation next. Tube sites and forums that allow unverified uploads exploit a big percentage of everyone, including women in their 30s and older who create their own work and distribute it on sites like OnlyFans, their own websites, through clips sites, or even DVD distribution—whatever that format is worth nowadays. Other exploited groups in the adult video industry include crew, who are not protected by the unions that protect crew members on Hollywood and TV productions in the United States. And, of course, there’s the exploitation we all inherently face under capitalism. But that’s a digression we’ll have to save for another day (and yes I am fishing for letters about capitalism and recreational sex).

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Jennifer Lyon Bell explains this a bit more:

I want to thank you for already understanding that paying for your porn is the best way to ensure that you’re 1) more likely to be looking at ethical porn, since all ethical porn sites charge a little something for streams/downloads/subscriptions and 2) helping create an economic production cycle that lets alternative/indie/ethical/feminist porn companies be able to make more films because of your support.

I do have some bad news about “regular, basic porn” though, which, without more detail, I can only interpret to mean mainstream porn. Most of it runs on one of these things; youth, power imbalances, and plots that involve cheating. “I won’t lie—it’s hard to find movies featuring female performers in their 40s that meet all your needs,” Lyon Bell says. “That’s because films in the common porn category MILF subsume most of the performers in that age bracket, such that MILF adult work is most of what they book. Unfortunately for you, the kind of storylines featured in the MILF category are often going to be upsetting for you. And that’s a shame for all of us because I would love to see more female performers in their 40s and 50s in more diverse roles.”

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Lyon Bell shared some recommendations for specific sites:

Indie label Bright Desire, with, for example, their film Tease, is a good choice. Bigger platforms Joybear and Erika Lust’s XConfessions have lots you might like as well. The performers are usually not quite the age you were hoping for, but plenty adult. All have good stories that you’d like. You can usually find them on their own dedicated platforms, as well as on other multi-producer variety platforms like Cheex, Pinklabel.tv or Arthouse Vienna.

Another great option is to find movies that aren’t story-based in the traditional sense (so you don’t have to worry about being triggered), but which involve more drama and emotion than cutting right into a sex act already in motion. Well-regulated couples-only amateur sites can be quite charming and sexy. I like Lustery, run by a female founder, which is a platform featuring only real-life couples. Couples in their 40s aren’t so common there, but there are many in their 30s, and if you like you can hear them talking more about their relationship. Or you may like my film Skin.Like.Sun., which I co-directed with my friend Murielle Scherre (of La FilleD’O). It stars a real-life couple who, while younger than their 40s, are clearly adults in a fun, highly sexy relationship.

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And, while Women by Julia Ann does include some performers who appear to be in their early 20s, it includes many scenes between women in their 30s or above, and the pre-sex introductions are about getting to know each woman in a profound way.

While I’m happy to pass along Lyon Bell’s recommendations, I’m also encouraging you to work on your trauma. Sometimes it’s a hard road, but it’s worth traveling. I think you’ve got this.

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Dear How to Do It,

I have a non-sexy question, but it’s not something I know anyone to ask and you might know someone. My polyamorous triad has been together for four months, and it’s seriously the best ever. I’m so happy. Sex is great, domestic things are lovely, we’re planning trips as individual couples and a group, everything is rosy.

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I’m a snuggler by nature and I HATE sleeping alone. My ideal sleep solution is in a pile with my partners, but with enough space that folks can roll around. I’ve slept three and four in a bed no problem before, but my partners were all smaller and we were all in college and less bound by schedules and bodily needs. My current partners are both much taller and broader than I am, and fitting into a queen bed is not working. This usually means the husband (they/them) and I end up sharing the bed and the boyfriend moves to the couch once I fall asleep as he is the most fickle sleeper. I feel big sad because our boyfriend is left out despite expressing a desire to sleep together. Boyfriend is also a literal furnace.

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I’m going to be getting a new mattress, and I’m looking for recommendations on one that is cool enough for the furnace boyfriend, decently priced, and not awful to have sex on. (I tried a Purple mattress with other partners once and it was atrocious to fuck on.) I don’t know any other triads and I am not in a polyamorous community. Do you have any recommendations for mattresses or other ways to facilitate three-person snuggling?

—Struggling for Snuggling

Dear Struggling for Snuggling,

Much like concepts of “good porn,” which almost always means “got me off without offending me,” mattresses that are “good to have sex on,” are also highly subjective. You know you don’t like Purple’s mattress. Great! What didn’t you like about it? What did you like about other mattresses? Is it about general firmness? The firmness of the edges? The texture of the top? Reminisce about mattresses from your past, and make a list of what works for you. From there, go on a search for mattresses that check all of your boxes, within the price point that fits in your budget.

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You’ll definitely need a mattress big enough for all the partners involved if you want to comfortably sleep together. Measure the width of yourself, your boyfriend, and your husband, add it all up, add a few more inches for breathing room, and see what you can find in that width. Remember that length is important for tall people, too. You might look for a company in your area that carries “oversize” mattresses, and custom sizing is also a possibility.

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As for the cooling aspect of your needs, I’m thrilled to introduce you to the category of product known as a cooling mattress topper. New York Magazine recently did a run-down of the best available in the U.S., ranging from under $200 to almost $600. Keep in mind that any topper will affect the squish level and texture of what you’re sleeping and having sex on, and apply the same process of looking for something that fills all of your mattress desires. Before you go cooling the whole mattress, though, it’s worth thinking about how much heat you and your husband need when you’re sleeping. If the two of you are happy with the temperature while your boyfriend is overheating, it might make sense to use a half-mattress cooler, or even a topper meant for a smaller mattress than what you end up buying so that only his area of the bed is chilled. All it takes is a little bit of math and some effort.

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Dear How to Do It,

All of my previous experiences with sex were in long-distance relationships or through mostly anonymous kink sites, and I’m having trouble adjusting to my first in-person relationship.

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My boyfriend of six months is great, I’m deeply attracted to him, we have great sex and communicate really well. I’m very happy with how things are, but he’s told me he wishes we would sext more because that makes him feel desired when we’re not together. I’m fully on board with this in theory, but in practice, I’m having trouble getting there. I was a fairly prolific sexter before—when it was my only form of sexual connection. I think I know what the main hurdles are, but I haven’t been able to figure out how to get over them.

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1) I have ADHD, so even when I try to make a point of sexting more, I just… forget until the next time he mentions it, which is probably because 2) having actual sex regularly has drained my sexual energy to the point where my daily masturbation is down to weekly, if that. (We have sex two to three times a week, depending on how much we actually see each other since we live about an hour apart.) 3) I’m pretty shy and anxious, and fully expressing myself without anonymity or distance has been a harder adjustment than I was expecting. He’s been great about it, but making the first move is still difficult. Do you have any tips or suggestions for me?

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—Wannabe Sexter

Dear Wannabe Sexter,

Let’s talk about the ADHD aspect first. “I just… forget,” is generally part of the life experiences of people with ADHD. You can set reminders, like an alarm on your phone with a note, or in your schedule if you use a digital calendar. I also think it’s completely fair to have a conversation with your boyfriend where you remind them that your (wonderful!) brain struggles with remembering things and ask him to broach the subject when he wants to sext. Take note of how this conversation goes—if he accepts you as you are and collaborates on solutions that are actually viable, great! If he’s holding you to standards based on people without ADHD, that’s something to pay attention to.

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In the same way that everyone has a different brain, everyone has a different sexual appetite. Yours might max out at two to four sessions of sexual activity, whether those sessions are partnered or solo, per week. One option is decreasing the amount of in-person sex the two of you have to make room for more sexting energy and desire. You also might consider having sex as often as you have been but with fewer orgasms, which has a way of generating sexual frustration and encouraging desire for sexual interaction.

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As for your third contributing factor, I’m curious whether you were initially hesitant with sexting when you started doing it in long-distance relationships and anonymous interactions. If so, you’ll know from experience that practice tends to produce ease, and you might be able to remember other things you did to help yourself feel more comfortable. If not, spend some time listening to the feelings that come up when you consider being vulnerable this way. I’d feel remiss if I didn’t bring this up; if you’re reluctant because you aren’t as trusting as you want to be, it’s worth treading carefully. Sometimes people who experience things like anxiety dismiss real warning signs when they do appear.

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You might practice writing sexts without sending them. A friend of mine who writes erotic fiction under the name Guy New York wrote one workbook called Write Till You’re Hard which might be useful. Guy also shared a few quick tips for sexting:

“You don’t have to be 100 percent honest when you sext. You can say, ‘I’m lying naked in bed, fingering myself,’ when you’re actually on the couch under a blanket drinking a glass of wine and playing animal crossing in the background. It’s a game. It’s for fun. Don’t let reality get in the way of enjoying yourself.”

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And, echoing one of Rich’s sentiments, Guy says go for whatever works. “You can talk about anything. Tell a story. Ask questions. What was the hottest threesome you ever had? What would you do to me if we were stuck in a hotel room for three days? You can role-play anything you want. Be a student, a daddy, a boss, a priest, a nurse, a sister, a fucking goat. I don’t care. If the two of you find it hot, go for it. No goats are being harmed.”

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With a little self-patience, I think you’ve got this.

—Stoya

More Advice From Slate

My husband and I have an amazing relationship, and I love him deeply. A few months ago, at my suggestion, we started trying threesomes (with another woman) and have really enjoyed it so far. It’s brought us even closer—it’s given me a chance to explore that side of my sexuality—and it’s been a really fun and positive experience. One of our boundaries concerns his orgasm, which we decided from the beginning should always be with me. Then… he immediately broke my trust.

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