How to Do It

I Know My Taboo Sexual Fantasy Is Unusual for a Woman. How Do I Do It Anyway?

A woman with hearts around her.
Photo illustration by Slate. Photo by Vadim_Orlov/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’m a 25-year-old bi woman who, ever since I was a young teen, has had a persistent sexual fantasy about older women—like, 40 and above. It’s been a constant thing that I fantasize about, and the only kind of porn I enjoy is lesbian porn that features this mismatch in ages. I know this isn’t the usual “MILF” situation, but I’m strongly into it. I have only ever had one sexual experience with a woman, and I mostly date men (my interest in women is mainly sexual). Now that I’m newly single, I want to explore this fantasy in real life, but I have no idea how to meet or advertise myself to older women. I have browsed Tinder and Bumble for a little bit while setting the filter to ages 40+, but the pickings were surprisingly slim for a big city. I’m not part of local queer scenes at all and don’t know how I would go about meeting a lesbian cougar in real life. But I really, really want to, before I age into a MILF myself!

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—Craving a Cougar

Dear Cougar Craver,

Balancing strong, recurring fantasies about a specific kind of person against objectification is a delicate endeavor. And dating apps inherently encourage us to make snap decisions about people based on a frequently cursory profile. If you want to go that route, you might have better luck with one of the many options discussed here by Autostraddle.

If you’re aiming for a physically driven hook up—which seems to be the case—be up front about it and save yourself a lot of inefficient back-and-forth with people who are looking for something with more depth. Disclosing your experience level will alienate some but might entice others. Remember, as much as these older women are the pinnacle of your fantasies, they’re human beings with their own criteria. No-strings-attached sex can still be respectful, connected, and intimate.

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I think your best bet is to get out there and do get involved with your local queer scenes. Make friends. Encounter new people. Show up, be interested, be honest about what you’re looking for, and you’re more likely to meet someone you mesh with.


Dear How to Do It,

I’ve been with my boyfriend for a few months (22-year-old man and 22-year-old woman). We recently went online shopping for sex toys (yay). I said I was interested in reversing the sex power dynamic and maybe trying peggingm and he seemed up for it, but he wanted to start slowly so we bought some butt plugs. And now they are here and I just don’t know what to do? I’m a long-time reader of this column and you guys talk about ass play all the time but I just—I don’t know where to begin. Do butt plugs feel good, or are they mostly to loosen the butt muscles before other stuff? Do I use lube and then put them in and then what? I really do want to try pegging eventually and my boyfriend seems interested too but I feel like I’ve got stage fright because of my inexperience.

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—Butt How?

Dear Butt,

Your stage fright, given your inexperience, is reasonable. Your concern is serving as a valuable protector of your boyfriend’s anus—that it’s your wisdom saying “whoa, there, we need to get some information first.”

Always use lube for anal. I wouldn’t recommend anything marketed as “warming” or “tingly,” and I consider numbing lubes a safety risk—because if you can’t feel what’s going on, you can’t feel your body’s limits, and you certainly won’t be able to communicate them to your partner effectively. You’ll also want to take care to match the material of the toy you’re using to the type of lube. Epiphora, of the sex-toy review site heyepiphora.com, told me that “silicone-based lubes offer more longevity—the synthetic ingredients don’t absorb into the skin—but can be tricky to combine with silicone toys specifically. You run the risk of the lubricant binding to the surface of the toy, creating a gummy mess. Some high-quality silicone lube are compatible with high-quality silicone toys, but you should always do a patch test on the toy first.”

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Epiphora continued, “Water-based is the most common type of lubricant and can be used with all sex toy materials. Being water-soluble, it washes off easily, but it dries up faster and needs re-applied more often. A thick, gelatinous lube like Sliquid Sassy works well for anal, as it provides extra cushioning.” And oil is a possibility—sometimes. “I wouldn’t recommend using oil-based lube with a porous sex toy material—such as rubber or ‘jelly’—because the lube could get trapped in the pores. All non-porous materials are fine, though: silicone, glass, stainless steel, hard plastic.“

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Butt plugs can feel good, and they can also help the sphincters relax. In people without prostates, like myself, the good sensation might stem from a fullness, pressure, or the still marginally taboo nature of it. In people with prostates, that little walnut is usually very pleasurable when stimulated. Now is a good time to do a web search for the anatomy of the prostate—“prostate anatomy” will turn up some reasonable diagrams, and you’ll be able to get an idea of what direction you’re searching in. It’ll be a few inches into his rectum, and you’ll want to feel around towards his pubic bone.

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I think it’s great that you’re going slow in the grand sense—starting with butt plugs, gathering information first—and I want to encourage you to also go slow in the moment. It might be tempting to thrust vigorously, but it’s best to restrain yourself until his sphincters have relaxed and he’s very turned on. With a butt plug, the pleasure is likely to come more from fullness and pressure than friction; dildos are a better tool for that. The flared base is very important for anal insertion, as it’s possible to lose an object and need a trip to emergency medical services. Communication is crucial—especially if he’s going to be face down for easy access, you’ll need to stay connected verbally.

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When you start incorporating strap-ons, you’ll want to get a harness that fits you firmly—I’m partial to Spareparts’ Tomboi, but your mileage may vary—and an appropriately sized dong with a flared base. You’ll also want to get comfortable with your new cock. It might take some adjusting. Strap-on in a nonsexual context and wear it around for a while. And when you and your boyfriend are ready for penetration, consider having him take the active role at first so he can control depth and speed.

Dear How to Do It,

My partner is an incredible person: silly, sweet, and compassionate. As someone who spent her young life dating mostly jerks, it took me a while to get used to being treated well, but after three years, I know this the best relationship I’ve ever had. The trouble is I can’t seem to acclimate to having sex with a sweet man! My past partners have mostly been intense, aloof people whose affection I had to chase after. My current partner is extremely respectful and lovey-dovey. I’m also very kinky, and my partner is pretty vanilla. When I’ve asked him for BDSM play, he’s always down to try, but it’s very much for my benefit rather than his. It never goes well! When he orders me around, or tries to pull my hair or hold me down, it just feels silly because it’s so out of character for him. It’s also unsatisfying for me—my enjoyment comes out of seeing how excited BDSM makes the other person. He’s just trying to be dominant as a favor to me (which is very considerate, but not pleasurable) What can we do?

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—Respectfully Restrained

Dear RR,

Your enjoyment comes out of seeing how excited BDSM makes the other person. Is it possible that you can enjoy seeing how excited some other specific sexual act makes your partner in the same way? If so, that’s one course of action. You could inquire about what that might be for him.

If you do want to continue to try this, ordering you around, pulling your hair, and holding you down are all under the umbrella of BDSM, but that umbrella is very large. And for a partner without BDSM experience or natural inclinations toward a dominant role in sexual interactions, I think you might need to give him more detail and insight into what you enjoy about these things. Spend some time thinking about what you enjoy about each activity. When you were engaging in compelling BDSM, what were the experiences like for you? What did you feel? Think? How much did it turn you on? Share all of this with your partner. It’s far from certain, but it’s possible that he’ll be able to find enjoyment in dominating you sexually once he understands what it does for you.

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Depending on how the two of you feel about non-monogamy, you could find an additional sexual partner who wants the kind of interactions you’re missing. Non-monogamy isn’t for everyone, and my co-columnist Rich’s advice to err on the side of the most sensitive partner’s needs bears repeating here.

Dear How to Do It,

My boyfriend has never been terribly interested in sex. He never initiates it and is reluctant to do it when I suggest it. But he does, and while it’s not great, it is very loving and romantic and sufficiently satisfying for me. We have been together for more than two years, and I really want to get married. He thinks I wouldn’t be happy in the long run.

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I had a much more active and much more varied and physically satisfying sex life before him, but I’m not one of those people who needs wild sex all of the time. I’ve always been a realist and I’m able to be happy with whatever I have in life, even if I would prefer to have more. What I value most is our compatibility in temperament, our shared interests and values, and our truly deep love and respect for one another. And a weekly expression of that in love-making would make me content. He knows all of this and has said he’d like us to be together forever, but just doesn’t enjoy sex and doesn’t want to commit to continue doing it. He now is saying he thinks he’s asexual. I find that hard to believe. From when we first met there were sparks between us. I’d catch him looking at my breasts and legs all the time and he often got (and still gets) an erection when I hug him and sometimes even when we’re just sitting and talking. And when we do make love, he is able to keep the erection for the duration, is attentive to my needs, and we both come. So how can he be asexual? Could there be something else going on?

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—Asexually Dubious

Dear Dubious,

There absolutely could be something else going on. What I’m certain of is that he doesn’t want to commit to continued long-term sexual interaction with you. And trying to prove or disprove his asexual identity is inappropriate. His erections prove nothing. Arousal non-concordance is common in men. A boner is not a statement of desire.

Sometimes when we’re dealing with identity labels, we forget that they merely describe a group of experiences and characteristics. Binary categories, whether we’re talking about male/female, hetero/homo, or ace/allo—as asexuals generally use to refer to people who experience attraction, and people who don’t—can prevent us from seeing the nuance and complexity of reality. I think you should read Angela Chen’s ACE: What Asexuality Reveals About Desire, Society, and the Meaning of Sex before you speak with your boyfriend about this again. There’s also an audiobook version if listening works better for you. Think about what this really means for your needs, and his, and whether this can work for both of you. If your boyfriend’s relationship to sex feels like a judgement of your value or attractiveness, that’s worth investigating. Good luck.

More How to Do It

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. It just felt like a more intimate thing, and it hasn’t been an issue until our most recent encounter, where it all went wrong right in front of me.

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