How to Do It is an advice column on intimacy.Got a question? Submit it here anonymously.
Dear How to Do It,
I recently hooked up with a guy who really caught me off guard. While we were talking dirty, he asked, “Am I the biggest you’ve ever had?” I was totally unprepared. I kind of just said “mhm” and tried to change the subject, but he kept pressing. Now, I’m left wondering if I should have lied to make him feel good or just ignored the question. The experience was otherwise enjoyable, and I’d like to see him again, but I dread the possibility of this question coming up again. What should I do if he asks me that again?
—You Don’t Want Me to Answer That
Dear You Don’t Want Me to Answer That,
This is a tricky situation. You’re being pushed into a conversation about penis size, something that often creates unrealistic expectations. On dating apps, for instance, guys typically inflate their sizes, so if you’re continuing that in real life, it feels a bit absurd. You don’t need to lie just to make someone feel better. Everyone knows that there are larger sizes out there, and if someone genuinely can’t grasp that, it’s a bit self-centered. It’s not your responsibility to keep someone’s ego intact.
I think you handled it well. You didn’t let it disrupt what was happening. But even if you had said something like, “Yes, definitely the biggest!” I wouldn’t have judged you. It’s possible that he’s inviting you into some fantasy. Maybe in that moment, he just wanted to feel superior, and indulging in that fantasy can be fun. While fantasies often stretch the truth, they aren’t lies in a hurtful way. That said, your situation is a bit complicated.
There’s really no clear right or wrong answer here. He could be looking for some sort of validation or just engaging in playful interest. If you suspect he’ll bring it up again and you’re keen on seeing him again, shutting him down might not be the best approach. You could acknowledge him by saying something vague like “It’s big” or “It’s up there,” as long as you feel comfortable with those responses. If you decide to go along with it for the sake of compatibility, I think that’s understandable.
Dear How to Do It,
I’ve recently tested positive for a high-risk strain of HPV. I often get tested for STIs, but I didn’t realize that HPV testing isn’t part of that routine, so my last test was during a pap smear a couple of years ago. Since then, I’ve had several sexual partners, but all were men with whom I used condoms. I’m not asking how I got it—I know condoms can’t prevent everything—but I’m questioning whether I should disclose this to past partners for the sake of their future partners. Should I tell the guy I’m currently seeing? What about future partners? Part of me thinks it’s pointless to inform men since they can’t get tested, but I also don’t want them to unknowingly put future partners at risk. Am I overthinking this? Is there some sort of guideline I should follow—medical, ethical, or just good manners?
—Don’t Want to Be HPV Mary
Dear Don’t Want to Be HPV Mary,
You’re not overcomplicating things. This question is quite valid and resonates with many. The issue of disclosure is nuanced and there isn’t a one-size-fits-all answer. You’re right that men can’t be tested for HPV in the same way women can, though there are options like rectal swabs, which may not apply here. Because of this gray area, the CDC has noted that the benefits of disclosing a positive HPV test to partners isn’t clear. What exactly can they do with that information? You’re correct that their understanding of HPV may vary; some might know about the risks involved and accept them. Although condoms help, HPV can spread through skin contact, so there’s still risk involved. Keep in mind that about 90% of HPV cases resolve on their own within two years.
Choosing not to disclose doesn’t make you a bad person, but if you do decide to tell your partner, you could use that moment to educate him about the virus and mention the Gardasil-9 vaccine, which protects against various strains. You could also share how common it is—most sexually active individuals will encounter it at some point. It sounds like you’d want to know if the situation were reversed. If he reacts negatively, that might reflect more on his maturity than your situation.
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Dear How to Do It,
I’m a 40-year-old trans guy in a two-year relationship with my girlfriend. The sex we have is enjoyable, but lately, my interest in it has waned. There are several factors: I’ve decreased my testosterone dosage, which has lowered my sex drive, and there are also aspects of our relationship at play. Before the dosage change, I felt the desire to engage in sexual activities frequently, but during a month when her drive was low, I suggested cuddling while I took care of myself. She agreed in theory but wasn’t really into it when the moment came. Another time, she was upset when I suggested a break during sex, recommending she take that time to pleasure herself instead.
She prefers slow, passionate lovemaking, which I also enjoy, but sometimes I desire a quicker, hotter vibe. When she wants to take things slowly, I find my attention drifting. She’s interested in exploring anal play, but it comes with many conditions, and she only tops occasionally, while I consider myself a true switch. We attend play parties, but I’m usually the one organizing everything, making sure she’s comfortable, which holds me back. I’ve considered going solo, but she’s not particularly keen on that, especially since I mostly connect with guys and know she’s uneasy about me being with femmes, which makes me feel restricted.
We’ve discussed the possibility of a threesome, something I’ve done before and enjoy. However, she hasn’t, and I worry I would have to bear most of the emotional load. Right now, our sex feels pretty basic, and it’s becoming less appealing to me. I know we need to talk about this, but I’m hesitant to sound like I’m blaming her. If she values her preferences, I’m fine with that, but I really need something to reignite the tension between us. How can I open this conversation without seeming accusatory?
—The Talk
Dear The Talk,
Your letter suggests there might be some core sexual incompatibilities between you and your girlfriend. First, consider why you want to stay in this relationship. It might help to write down the reasons you value your partnership; being clear about this can aid your upcoming conversation. You can mention these points either at the beginning or seamlessly in the discussion to lessen any feelings of accusation. Start by complimenting her or emphasizing what you love about the relationship; this could help her receive your feedback more positively.
Also, reflect on how reasonable your requests are. It seems that your girlfriend has firm boundaries, and while that’s okay, it’s also causing you some frustration. If she never feels completely comfortable at play parties, perhaps she’s only attending for your sake? If you feel like you’re always the one engaging, is it worth going? And can you accept letting go of certain aspects of your interests while with her?
Many people see openness not as limitless freedom, but rather as a negotiated agreement between partners with varying desires. It’s reasonable to feel like you’re giving more without receiving enough in return. Still, your girlfriend has made some sacrifices for you (like accepting her discomfort with you attending parties alone). This may be as far as she can go. A piece of advice from one of the subjects in Tristan Taormino’s book on ethical non-monogamy might resonate with you: “You play to the level of the least comfortable person if you want to keep everyone content.” You might be at that juncture now. Consider where to go from here and what options remain.
—Rich
