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,
My partner (cis male) was on the Walgreens website and was VERY excited about the pickup feature. Lo and behold, even condoms can be ordered at the drive-thru! The problem lies in that he might be a little too excited about this newfound convenience. He clicked into the condom category and was overwhelmed by the options! “Do I get the ultra-sensitive? What about the ribbed? Hmm, maybe it’s time I try the extra thick with the glow-in-the-dark lubricant!” I’m at my wit’s end! I don’t know how to advise him. I don’t know what’s good for a peen. Is this a normal question? Am I supposed to have an answer? Is ribbed better than ultra-sensitive? Are ribbed and ultra-sensitive the same thing? I hate to feel like a prude, but I think I’m out of my depth here.
—To RIb or Not to Rib
Dear to Rib or Not to Rib,
Let’s start with “normal.” Sometimes people use this word to ask whether something is typical. We might know the average viewing habits of users of a certain porn site, the average issues a couple’s therapist encounters, and the average type of condom purchased. But each of these points of data is inherently biased in one way or another. Sometimes people use “normal” when they really mean “Is this OK?” From what you’re saying, this question is stressing you out. Being stressed out by an overwhelming amount of options, or questions that feel like they require decisions is a part of the human experience. And when we’re talking about sex, it’s OK to feel overwhelmed.
I see you saying that you don’t know what will be good for your partner’s penis, and I want to remind you that what’s good for your vagina is relevant as well. I don’t know your vagina or your partner’s penis, so I’m not able to make any quality guesses about what you’ll enjoy. It sounds like you don’t know how you feel about condoms that are ultra-sensitive, ribbed, or extra thick. It also sounds like your partner is pretty excited by all the options, and wants to share his excitement with you. And there’s a significant chance that he’s asking you these questions because he wants to try something new while being respectful of your preferences.
This is not a math exam. However, it could be a relaxed experiment. Are you open to trying some different condoms? If you aren’t, communicate that you’d prefer to stick with what the two of you know works, which I would categorize as more prudent than prudish. If you are open to some novelty, start slow. Maybe a variety pack. Maybe a pack of condoms you’re familiar with and a three-pack of ribbed ones. Having a small conversation about what to try first might be fun, but that conversation doesn’t need to be an exhaustive weighing of all possible options. Start with something like “I don’t know, so let’s find out.”
Dear How to Do It,
I (25F) have recently started dating an amazing guy (26M). It’s my first relationship ever as a late bloomer. He’s smart, witty, sweet, and even cuter in person. I honestly thought people were making up the whole “butterflies in my stomach” feeling until now. But I am having a lot of anxiety around the relationship and the potential for physical intimacy. I’ve never gone beyond a quick kiss at prom and didn’t really start exploring my sexuality at all until I was 22 and realized I was bi. The most I’ve done is masturbate on my own. I always pictured my “first time” with another person in the context of a serious relationship rather than a casual hookup as I really wanted to trust the person I was with. He has more sexual experience than me though we haven’t talked in depth about it yet. I do know that he has had more casual sex outside of established relationships and is pretty comfortable with his sexuality. Additionally, he is trans and has cerebral palsy. He has some difficulty with speech and uses a wheelchair.
I tend to be a worrier in general. I work in health care and have seen firsthand how often disabled folks are let down by the people they trust the most, or by our ableist systems in general. I’m terrified I will hurt him somehow by asking the wrong question or not supporting him correctly. I’m afraid that my own lack of experience will hurt us as I don’t really have a baseline of what I like in bed to compare to. I know everyone’s preferences are different regardless of whether someone has a disability or not, but in a weird way, I feel like the stakes are higher somehow. I have a therapist for my anxiety but she’s given more generic advice just reassuring me that good intentions are enough (which I know for a fact is just not true). How do I navigate sex/intimacy with a disabled person when I don’t have any experience myself, and how do I build a solid foundation for a relationship in addition to sex?
—Scared to Hurt Him
Dear Scared to Hurt Him,
Not only are you in a relationship for the first time, but you’re also having your first giddy feelings toward another person. And you’re beginning to explore the possibilities of sex with partners. These are three big life changes. Lots of different ideas circulate in our culture regarding how a first sexual experience should be. Lots of people dream about what their first time will be like. And many put a lot of pressure on realizing an ideal. When we take into account all of these facts plus the anxiety you experience, I’m not surprised that you’re feeling fear—and what sounds like doubt. Do consider whether any of your therapist’s general advice can be applied to this situation. Anxiety around sexuality and relationships is still anxiety, and the ways we manage it in the rest of life are often applicable.
One way of building the trust that you picture as part of your sexual experiences is by being emotionally vulnerable. Regardless of what physical interactions you eventually have with the guy you’re seeing, you have an opportunity to practice that vulnerability together. If you haven’t had a talk about what level of commitment the two of you want, and how emotionally entwined you want to be, start there. If you have established that you’re both working toward building this kind of intimacy and trust, share your anxieties with him.
I reached out to Dr. Mitchell Tepper, sexuality educator and coach—and one of the directors of the documentary Love After War—for some additional insight into your letter. Tepper suggested over email that you voice what you’re experiencing. Tell the guy you’re seeing about the attraction you have toward him, the anxiety you’re experiencing, the ways that anxiety stems from your own inexperience, and, yes, the anxiety you’re feeling around the specific details of his disability and his gender identity. “By sharing your concerns upfront, it gives him a chance to respond,” Tepper said. “More likely than not, based on the fact that you say he is comfortable with his sexuality and has more experience, he will seek to alleviate your anxiety and share with you any special needs he has, and any of his own concerns.” Tepper advised that you consider how holding your feelings back may be another form of treating him differently, too.
Whether you compose a short essay, or note some key phrases, think through what you want to say before you broach the subject—and write it down. Beginning the conversation can be as simple as “I’m incredibly anxious about discussing what I’m anxious about, and have made some notes so I can remember everything I want to express.” Be as concise as possible with each thought, and ask for your partner’s responses as you go. Listen to what he says, and ask for clarification when you aren’t sure whether you’ve understood. If the first conversation covers the fact that you’re anxious and what his response is, that’s plenty. If you’re both feeling up for more, go for it.
Once you’ve had the conversation and it’s time for action, keep in mind that, we all have to start from square one with every new partner. We don’t know how we’re going to fit together, and how we’re going to rub at each others’ sore spots. We don’t know what the challenges will be until we encounter them. We find out and problem-solve along the way—regardless of the specifics of each person’s body, identity, and sexual and emotional desires. There will almost certainly be moments where you feel like you’ve made a mistake or you actually have. Lay the groundwork of open communication, and practice noticing when you’re overwhelmed. That’ll help you out when you do make a mistake, or when he does.
Start slow, and remember that both of you can always ask for a stop, a pause, or a discussion. The more practice you have at expressing your desires and boundaries, and listening to his, the stronger base you’ll have to build confidence on. You’re the best expert on what feels good for your body, and your guy is the best expert on what feels good for his body. Extend a little trust by believing that he’ll tell you what he needs, and telling him what you need, yourself.
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Dear How to Do It,
I am a gay trans man and I love being topped and penetrated in both my holes, but especially my ass. Unfortunately, a lot of my cis male partners aren’t used to topping someone with a vagina. Frequently when they are fucking my ass and their dick slips out, they accidentally push it back into my vagina instead of my ass. I think this keeps happening because when I’m all lubed up/self-lubricating, my vagina is just the path of least resistance. Sometimes it even takes a moment before either of us notices. I know it isn’t healthy for my vagina to go directly from anal, but what can I do after it accidentally happens, besides just switching back? Are there different positions that can help prevent this from happening?
—Slippery Situation
Dear Slippery Situation,
I suspect that there are positions that would reduce the frequency of accidental ass-to-vagina. There are probably also more specific angles and some variations in speed and intensity that could help. Think about all the times your top has slipped out of your ass, and look for common themes. Think about all the times it hasn’t happened, and look for common themes there as well. If you aren’t seeing any patterns, start making basic notes after sex. If you do notice patterns, you’ve got some idea of how to reduce this issue moving forward.
There are other ways you can set yourself up for success. Have a bit of a talk with your cis male partners before you get started. Depending on your dynamic, this can be presented as a sex ed lesson, intimate emotional sharing, or a man giving a report on the needs and vulnerabilities of his equipment. However you do it, communicate that vaginas are easily harmed by bacteria and that you need your tops to stop when their dicks slip out of your, well, bacteria-filled asshole, and take a moment to make sure that they’re re-entering that same hole. You also might look for a jock strap that covers your vaginal opening but leaves your asshole open to attention. And if you’re into having both holes filled at once, a dildo that is approximately the length of your canal can occupy that space—it’s pretty hard to accidentally penetrate an orifice that is already full.
As for what to do after ass-to-vagina penetration happens, that’s a question for your doctor. If there’s a sexual health clinic near you, schedule an appointment. Regardless, do what you can to prevent it from happening in the first place.
Dear How to Do It,
My girlfriend and I are in a long-distance relationship. When we were living together, we would have sex maybe once every six to eight weeks, which was frequent for me and infrequent for her due to different sex drives. Now that we’re apart, and I only see her once every couple of months, something she used to do sometimes is now something she does almost every time I see her. She will ask to make out, and then when we’ve been making out for several minutes, tell me that she’s horny now. The thing is, 90 percent of the time, I would be fine with having sex if she just asked from the beginning. But I don’t really like being baited and switched. I do go along with it most of the time, but it feels like such a teenage boy move that I’m always a little bit put off. I’ve mentioned that I would prefer to just be asked from the start, but I really do think this is an organic thing from her—she’s not trying to manipulate me, she is just informing me that she wants to have sex now. I know she wouldn’t be upset if we didn’t, I just feel responsible to follow through with what we started. I do enjoy myself! So it’s more of a difference in planning preferences and spontaneity than anything else; if we’re having sex, I’d rather know from the start. Do I need to loosen up here and just go with the flow?
—Not Flexible (Physically or Mentally)
Dear Not Flexible,
In the middle of your letter, you express a feeling of being “baited and switched,” and describe your girlfriend’s expressions of sexual desire as a “teenage boy move.” Later on, though, you articulate that you suspect she is simply expressing her sexual desire when she feels it. Spend some time thinking about where your feeling about being subject to a switcheroo is coming from. Has this feeling come up in previous relationships? If so, what were those contexts like? Is the context of this relationship similar? Does your girlfriend have other behaviors that feel like patriarchy-flavored immaturity to you? If so, does your reaction to this situation indicate uncertainty about the future of your relationship?
The differences you mention in preferences for more planned or more spontaneous sex are another area that is worth introspection. What do you prefer about planning? What are your feelings toward spontaneity, and where do those come from? Try to get an idea of what you need, what your comfort zone is, and how often you can comfortably stretch outside of that zone. You also might think about what spontaneity does for your girlfriend. If you’ve had talks about this, do your best to remember what she’s said.
When you’re feeling like you understand some of what’s happening on your end, broach the subject with your girlfriend. Whether you do this in person, over video, or on the phone should depend on how the two of you communicate best. Whether you bring the subject up organically or ask her to set aside time to have a serious talk should depend on what works for the two of you as well. And if there’s a similar disconnect in preferences toward degrees of planning with conversations, that’s something to consider. Once the two of you have had some talks, I think you’ll have a better idea of whether you want to—and can, in a healthy way—go with the flow.
—Stoya
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I was 25 when I married my wife. I’m 44 now. She’s 47. We have two children together, and a grown stepson whose father is in prison. Both our dating and engaged relationships were full of shared activities and physical touching. We did everything together from cooking to fishing, playing cards, walking, riding back roads, having sex, and socializing with friends. She never told me “no” when intimate desires scratched me. Never. Not once. Our relationship changed immediately the day after our wedding—and I do mean immediately.
