How to Do It

I’ve Been Living a Lie With Well-Endowed Men. My New Boyfriend Proves It.

A couple interlocking legs under an eggplant emoji.
Photo illustration by Slate. Photo by PeopleImages/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 have been dating an amazing man for about six months. After a long line of hookups and failed dates I was getting jaded when I swiped right on my man and we hit it off. Safe to say we are in the puppy-love phase.

Before him, I would have said big dick was a necessity. Deep and intense penetration was hot and essential to me. The term “size queen” comes to mind. I know it’s not fair, but “little D” was a deal breaker. That’s just the way it was for me. Until now. My boyfriend’s penis is small and on the soft side during erections. And sex with him has been 100 percent amazing. Our focus is not on penis-in-vagina sex, and I have never cared less about it. The sex we have is passionate, creative, and fun—my boyfriend is skilled and generous. He gives me the most intense orgasms I have ever had. I feel comfortable and uninhibited with him. I also love his dick. (Side note, it’s actually much more fun to blow a smaller dick—the things you can do!) My question is, WTF, have my supposed preferences been reset by my skilled lover? Or after the flush of new love wears off, will I start to miss big D? What do I do if that happens? I want to be prepared come what may, because I think this man is a keeper.

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—Big D, Little D

Dear DD,

I spend a lot of time reading books by sex therapists. Whether it’s Ian Kerner or Emily Nagoski, Barbara Carrellas or Tina Schermer Sellers, they tend to encourage people to enjoy the full range of sex, not just the thrusting of a phallus into an orifice. Whatever the contributing factors, you’re now enjoying a wider range of sexual activities as the main event, and it sounds like you’re having a blast with it. For some people, changes are abrupt, and for others, changes are so subtle and slow they’re barely noticeable, but most of us have sexualities that shift over the course of our lifetimes. As you age, that broad sexuality you’re experiencing will help you maintain sexual connections with your partners and with yourself.

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New Relationship Energy does have a way of making every little touch as titillating as one could possibly want, and that effect does tend to lessen after a while. One thing that seems to help is prioritizing variety in your sexual interactions, which the two of you seem to be really great at. It’s possible that after another few months you’ll be pining for more protruding penises. It’s also possible that you’ll never look back, though likely it’ll be something in between.

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As for what to do, it depends on what you miss about big dicks, and to some extent the dimensions of his hands. I’ll do this in reverse order so you don’t spend the whole paragraph wondering about that last one. When I hear “deep and intense” penetration, my mind goes to fisting, which is a very slow and gentle process of taking a person’s whole hand into your orifice. You’ll need lots of lube, to be very turned on already, and to go incredibly slowly. Queer porn brand CrashPad (NSFW) has an extensive video guide, and this is something you’ll want to research beforehand. If it hurts at all, stop and disengage slowly. If this is more about the penis being a penis for you, and being attached to your lover, there are penis extensions that strap on with a hole inside for the person’s dick. You don’t mention whether he’s sensitive about his measurements, and if that’s the case, this suggestion may cause more trouble than it’s worth, but it may be an option. It’s worked wonders for some readers.

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Mostly, for now, I think you should focus on the present and keep up your exploration. You’ve got a great guy and you’re having great sex. And for what it’s worth, I agree: a smaller penis is much easier to maneuver in my mouth.

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Dear How to Do It,

I am suddenly very confused about my sexuality. I have a very good friend I’ll call “Lisa.” We’re walking buddies, tennis partners, coffee/tea/wine friends, and a lot of that kind of stuff. Lisa is in her late 40s with a grown kid, and I’m in my early 40s with a couple of kids still in school. Lisa is very outgoing and has a big personality. I consider myself way more average socially. Not a wallflower by any means, but I also usually let her be the more visible one. Lisa is divorced, and I am not. My marriage to my husband is great, but not remarkable. Our sex life is good, if you think sex four to six times a month is good (I do!).

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I have never experimented with another woman, and have never really thought about it seriously. My husband is “typically male” in that he has lightly hinted at wanting some kind of threesome that involves another woman, but we’ve never seriously pursued it. A big reason I’ve always shrugged it off is that I was never interested in having another woman in our bed—to share my husband with her or to having sex with her myself.

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Well, Lisa had a small holiday party before all the omicron craziness blew up. I was talking to some people and waved my arm around for the story I was relating and accidentally grabbed Lisa’s breast, because I didn’t see her next to me. She made a joke about that being more action than she’s had in a long time and we all laughed. I wasn’t even embarrassed about it because it was a complete accident. Thing is I could swear I caught her looking at me a couple of times after that because we locked eyes. And when we were leaving, we hugged and again it seemed to me that she looked at me differently and her touch lingered. Not necessarily inappropriately or in an overtly sexual way, but it felt different.

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Obviously, it’s been on my mind, and I’ve been ruminating on it for weeks. I haven’t said anything to anyone about it, including my husband. She’d been away visiting her daughter over both the holidays, and we’ve texted back and forth since her party, but I haven’t actually seen her since then partly because I’m trying to process this. What I’m processing is that I think I am feeling some sexual attraction to her, but I am pretty sure I am not feeling attraction to women in general. We are close friends, and I have seen her naked or near naked a number of times in the past. But that did not result in any sexual response from me at the time. I’m feeling one now to the point where I actually masturbated to it. I am feeling really stuck about what to do about it, though.

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—Bi for One?

Dear Bi for One,

Any sexual frequency is a good frequency if the partners are both happy with it, including never. With that out of the way, let’s talk about the interaction between you and Lisa. Labels are great in a lot of contexts—sifting through dating apps or quickly establishing general interest at a party—but can sometimes feel like categories we’re trying to fit into, instead of words we’re using to approximate ourselves. Sorting people into the categories of male and female, homosexual and heterosexual, or any other binary, leaves a lot out. And most of us aren’t a hard 0 or 6 on the Heterosexual-Homosexual Rating Scale, otherwise known as the Kinsey scale, even if we are using that framework. You’re a woman who is suddenly sexually attracted to another woman for the first time, and you don’t need to have a word to describe your orientation now or ever.

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The first question to answer is “Do I want to have sex with Lisa in any context?” You’ve imagined her during masturbation. Spend some time imagining having sex with her, and waking up next to her. Think about all the ways this could change your relationship—positive and negative. What if you lose her as a friend? What if your companionship and lust come together to create deep feelings and attachment? Do you live in a town where this getting around could cause you issues, and do you think you can navigate this with your husband?

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If you do this and you’re still interested in pursuing sex with Lisa, the next thing to consider is what context you’d like that to be in. Do you imagine privacy, just the two of you? Is your husband there and watching? Is he participating? Are they both lavishing attention on you? You and him on Lisa? Lisa and yourself on your husband? Is it a spiraling group where everyone is making love to everyone else? Is this mostly physical, or also mental or spiritual?

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Then, assuming your relationship with your husband is healthy, talk to him about it. If the relationship isn’t stable now isn’t the time to approach this. Pick your time wisely—when you’re both comfortable, have eaten, have time to talk if things get complicated, and have privacy. Start with how much you love him, your commitment to your relationship, and then tell him your specific desires toward Lisa. Give him time to process what you’re saying, ask questions, and respond. From there you’ll have a much better idea of what your options are.

As for approaching Lisa, I’d choose a private setting that she can easily leave. Have this conversation when you’re both sober, with a comfortable amount of space. Tell her that your accidental breast grab has sparked a crush, and whatever else you want to communicate at first. You might write this out beforehand, and would definitely do well to consider what you’ll say first. Again, from there, you’ll have a better idea of what’s possible. Good luck.

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Dear How to Do It, 

I am a woman in my mid-20s and my boyfriend is my first sexual partner. He’s gentle and attentive and catches on quickly to what I like, but I haven’t been able to orgasm during partnered sex, even though he is doing all the right things and I am very much attracted to him. Certain touches and positions start off great, and then it seems like I focus too much on what he’s doing. The pleasurable feelings turn into normal “I guess he’s touching me” ones, kind of like how the only difference between tickling someone and just touching them is whether or not they expect it and (to some extent) how much intent is behind it—although my boyfriend is both persistent and goal-oriented. Arousal is not an issue, as we’re still in that new and shiny phase where sitting around together makes us both horny. I do take an SSRI that may affect things, but I can and do orgasm on my own (although I need help from porn). Any suggestions on how to keep myself in the right mindset during partnered sex? I still get a lot of pleasure out of our experiences, but this may become a bit deflating for boyfriend if it keeps up.

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—Mindful

Dear Mindful,

Focusing during sex can be a challenge. I’m wondering if the porn helps you by giving you something sexual to focus on as a way to keep your mind from wandering. If that’s the case, I have some ideas. You and your boyfriend could build a robust erotic vocabulary and fantasy life, keeping your brain and attention engaged in that interaction with him. You could turn the lights on and bring in a mirror, if you aren’t already doing so, to give you visual stimulation. And working off of your sign-off, you could try bolstering your mindfulness with physically focused activities ranging from body scanning—where you sit or lay in a neutral position and focus on each body part in turn—to mindful eating or walking. You can also focus on your individual body parts during the sexual interaction. Meditation outside of sexual contexts will help you use those skills when you are having sex.

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I’m also wondering how your control of your attention is in other areas of your life. If you’re struggling, and you haven’t brought this up with the person who prescribes your SSRI, please do. They may be able to make changes to your medication that are helpful.

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You may also not feel entirely comfortable with your boyfriend yet, or at least comfortable enough to let go. Orgasm is a powerful experience, and trust takes time to build. You might think back on whether this distance has increased or decreased over time or stayed consistent. And it’s worth asking yourself if you’re worried he may be bored or otherwise not interested in continuing to give you pleasure—that can really throw a person out of the ability to relax, receive, and respond, and can be remedied with a conversation and taking him at his word.

More How to Do It

I have a really thorny ethical question I can’t quite wrap my mind around. I was seeing a guy earlier this year. The relationship was long distance, which is why it took me way longer than it should have to realize I was his dirty little secret: He had a live-in girlfriend, despite pressuring me to commit to monogamy. As soon as I found out, I cut off all contact with him. Since we broke up, I’ve been dating around, and I recently made another discovery that I can’t tell if he deserves to know.

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