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 got assigned a roommate when I started college. He’s a cool dude and we’ve become good friends. He’s gay and I’m OK with that but he’s also shy and doesn’t get any action. Problem is that he admitted that he’s attracted to me and really wants to get it on. I’m straight but gay stuff doesn’t disgust me. Should I give him what he wants? I want to keep our friendship but I don’t want him to completely fall in love with me. But I’m also interested.
Dear Friendly Roommate,
In seven sentences you say “gay stuff doesn’t disgust me” and “I’m also interested.” There’s a pretty big gap between not disgusted and interested. This guy is your roommate—which is not necessarily impossible to change if the situation gets unbearably awkward but will be an awkward process itself, involve procedures and paperwork, and generally be a disruption. And, whether you’ve got some preconceived notions or he’s prone to intense unrequited crushes, your concern that he might “fall in love with” you gives me pause. This could get very messy.
Let your roommate down firmly but gently. Tell him that you think he’s a cool dude, you’re happy to be his friend, and you don’t want to pursue sexual interaction. If you’ve got the time, do offer to go out with your roommate to places where he can talk to men who might be interested in him and be there for moral support. If you decide that you are interested in having sexual interactions with men, you’re best off with someone you aren’t currently living with.
Dear How to Do It,
I’ve been with my boyfriend for seven years, and recently we’ve been able to get a place by ourselves, so we have privacy now. We’ve been exploring and experimenting sexually with each other. It’s been great, but sometimes after sex, and he always gets off, my boyfriend gets on porn. It’s always oral, and that’s my weak area. I’ve only ever done oral on him, I’ve read and watched stuff to try and get better. It definitely helped, but I still feel average. Should I be feeling as hurt as I am by this? Is it normal? How can I get better at oral, or get rid of my gag reflex and learn to deep throat and swallow?
—Swallow My Insecurity
Sometimes, after you and your boyfriend finish having sex together, which includes him having an orgasm, he watches porn. Have you asked why? I can imagine several possibilities. For instance, if you are finished with sex after a certain period of time, after a certain amount of your own orgasms, or after his orgasm, it may be that he isn’t finished and is respecting what he perceives as your lack of interest. In the totally opposite direction, he might be actively trying to hurt your feelings. Are there other areas of your relationship that hurt your feelings or fuel insecurity? If so, whether it seems mostly self-generated or mostly in response to things he says and does, find a way to have several sessions with a therapist to talk this through. If not, ask your boyfriend directly what he gets out of porn when he’s just gotten off.
“Should” and feelings are sort of at odds with each other. Feelings happen, without our permission. Where concepts like “should” apply is our actions. You’re hurt. That’s OK to feel. You could also feel glad or aroused or disgusted. All of those feelings would be OK too.
“Average” and “better,” with regards to dick-sucking skill, are absolutely subjective, and, while I do have thousands of words in me about the concept of “normal,” that’ll have to wait for another time. More experience might mean you have a wider variety of ideas and more practice implementing them, but no matter how many penises we’ve fellated, we must all start at square one with a new partner and find out what they, specifically, like. Asking directly is one way. Asking about other blowjobs they’ve enjoyed is another. And trying all kinds of stuff while watching their reactions and soliciting feedback is a third. The trifecta, altogether, is ideal, as is finding the balance between what your partner enjoys and what brings you joy. So, is this goal of getting rid of your gag reflex, deep throating, and swallowing coming from things your boyfriend and you have discussed? Or is it based on a bunch of assumptions about what men enjoy formed by porn and copies of 90s-era Cosmopolitan Magazine? Rich and I did have a chat with several tips a couple of years ago, which includes a bit of discussion of the merits of gagging. I’ll add that there’s often a lot of room between the point that you gag and the point that you vomit, and, for me, it was less about getting rid of the gag reflex (which, if you’re choking on something one day, will be useful) than accepting gagging and thinking of it as a thing bodies do that can also squeeze a penis in a way that some find interesting and produce that “throat slime.”
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Dear How to Do It,
Is there any way to stop feeling like an imposter or an idiot when you’re dominating someone?
I’ve (she/her) recently entered a relationship with a gorgeous, wonderful man. I’ve always been… latently kinky? I mean, I had a lot of fantasies that very much involved heavy power play elements, but due to previous trauma, I’ve only actually started enjoying sex at all in the last year. Previous partners have had the casual kink levels that all Millenials have, and they’ve always taken a dominant role—choking, name-calling, nothing wild. My new guy is a serious switch, and he’s made me realize that I really want to dominate him. The fantasies I have about it are amazing. But whenever we’re having sex and it starts turning in the direction of me being dominant, I remember that I’m…me? And I just can’t take myself seriously in that role. So far I’ve had a blast hand-cuffing him and scratching him while I’m on top, but I want to be leading him around with a collar and getting worshipped. I buy rope, I practice my knots, and then I bottle it and never tell him. How do I stop feeling like he couldn’t possibly take me seriously? Are there books?
Dear Disappointing Dominatrix,
You are you, and you have many facets. A few acting classes might help you feel more comfortable with stepping into a role. Sanford Meisner on Acting might help you start thinking about how we can build characters from parts of ourselves. Mostly, though, the more experience you have, the more confidence you’ll develop.
Generally, I’d say keep taking small steps. You’re hand-cuffing him and scratching him now… so how about collaring him and then leading him to where the hand-cuffing and scratching will happen? You can build slowly toward more complex sessions or more intricate props and implements. Asking your partner to define a feeling they want to experience can be a navigational point to return to if you’re wondering what to do next, and blindfolds are great for preventing them from seeing any facial expressions of “Oh god, oh god, what do I do/say/think?”
Books and workshops abound. 7 Days of Domination, while it leans toward an audience of sex workers, has several video classes that may be useful for you, including one by Isabella Sinclaire on scene choreography and keeping the flow going. The area you live in may have one or more groups that offer live workshops. And, if this is within your budget, you may be able to hire a professional dominant for coaching sessions.
Most importantly, remember that you’re both engaged in a fantasy—he probably won’t take you 100 percent seriously, and even if he’s only taking you 40 percent seriously he’ll likely try to play along as though it’s double that amount. And do have a discussion about this. The more of a foundation of communication the two of you have, the richer and safer your sexual interactions are likely to be.
Dear How to Do It,
I could use some advice on having sex with a new guy for the first time since my husband’s death. The first time I had to fill out a form and mark my marital status as widowed, I burst into tears. The first time my gynecologist asked about my sex life after my husband died, I started bawling. The first time I had to list someone other than husband as my emergency contact…three guesses. I couldn’t even say the “w” word without choking up for at least two years. So I think we all know what’s going to happen the first time I (try to) have sex now.
The obvious solution would be a chill male friend or ex-boyfriend. But all the ones I would feel comfortable with are partnered. Tinder doesn’t strike me as a great place to look for a guy who would be cool about me crying before, after, or God help us, DURING the act.
What I really need is a straight-ish or bi-male prostitute. That way, if I start crying, I can just say, “Here’s your cash, I’ll call when I’m ready to give it another shot.” But my online searches on male escorts for women so far show mostly a bunch of testosterone types with the whole “you’re paying for a date, not for sex” disclaimer. I did find one local guy on a mostly gay escort site who seemed to have a much more laid-back “let’s respect each other’s boundaries” vibe and who was open to working with men, women, and trans, but I’ve been told when finding a pro it’s best to find someone with their own website and I can’t seem to find any other info on this guy, even though he claims to be on Instagram under the name he used on the site. Because prostitution is illegal here, I can’t really ask around for what I need. What should I do?
—Fear of Tears
Dear Fear of Tears,
I’m sorry for your loss, and for the emotional distress you’ve been experiencing. I see two big assumptions here. One is that you’ll burst into tears the first time you have sex with a new partner, and the other is that you need a friend doing you a favor, or a hired professional, to find someone who is open to that possibility. It is possible that you won’t burst into tears, and it is possible that you will find that a partner you’ve spent some time with, formed a rapport with, and shared your fears about sadness with will be understanding. I think the first service worth patronizing is mental health support, to help you work through these beliefs and come to terms with the way that grief, as Sherry Walling recently described, “gets absorbed into you until it’s part of what makes you whole.”
The same illegality and stigma that makes it difficult for you to ask around, or vet a potential provider—the vaguely worded April 2018 amendment to a law commonly known as FOSTA-SESTA—also makes it difficult for providers to openly discuss services they offer, and share safety tips among themselves. And it leaves me, in the course of attempting to provide you with advice, trying to guess what I am and am not legally able to say here—what kind of speech I am able to engage in. So, if your work with a therapist doesn’t shift your ideas about your options for sexual encounters at this stage of your life, I suggest you save up and take a vacation somewhere with less restrictive laws around sexual labor. The U.K., excluding Northern Ireland, seems like a great place to visit any time of year.
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I’m a 40-year-old guy who’s been reading a lot about sex in the last year trying to become more sex positive and also improve my sex life. I’ve been married for 13 years to an amazing woman. I saw a phrase in a book this week and I had a huge “aha” moment.