How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to email@example.com. Nothing’s too small (or big).
Dear How to Do It,
This is by no means a major problem, but it does involve the issue of consent, which is, of course, major. I’m a straight, single guy in a casual relationship that’s been going on for almost a year. “Peggy” and I hang out two or three times a month—drinks or a movie, conversation, then ending the night in bed. Neither of us wants anything more serious, but we enjoy each other’s company tremendously and the sex is great, especially oral, which we both dig giving and receiving.
Here’s the issue: The last time Peggy slept over at my place, she woke me up with a blow job. Now, being asleep, I couldn’t technically give consent. I didn’t feel violated or victimized though; actually, I felt fantastic—it beat the hell out of any of my phone’s ring-tone alarms. After she finished, she acted like it was no big deal and we snuggled until I was ready to reciprocate. My question is this: Since she introduced the act, is it OK for me to return the favor by going down on her the next time I wake up before she does? My instinct is that since she’s already taken the initiative with me, she’ll be receptive, but I’m concerned about the questions of consent and physical power imbalance, and I certainly don’t want to do anything to make her feel violated or victimized. (I know that the obvious answer would be to ask her permission the night before, but that’d spoil the surprise.)
Dear Wake-Up Call,
She took a gamble with your feelings, and I’m glad it worked out OK. Even though you don’t feel violated or victimized, I urge you to at least mention consent to her. Start with the blow job that happened. You might say something like “Hey, that time you woke me up with fellatio was really hot, and I feel totally fine about it, but I do want to address that this could have gone differently.” Or even as subtle and positive as “I loved that alarm-clock oral, and I’d like to give you consent to do more of that in the future because consent is important and I definitely want more of that kind of interaction.”
Presuming she responds appropriately—asking questions, some signal she’ll be more cautious in the future, whatever expresses safety to you—you might start moving the conversation toward how she’d feel if something similar were done to her. She might volunteer that she’d like to be woken up erotically.
At this point, specifically ask if she’d like you—particularly you—to wake her up one morning, and inquire whether she would like it to be a surprise. Yeah, you’ll tip your hand by having a discussion first, but you can mitigate that by waiting a few days to let the conversation fade. We don’t really expect things when we’re asleep, do we? I think losing the surprise factor is worth it to prevent potentially hurting someone, or even just to stick to best practices. Otherwise you’re taking a gamble with someone else’s feelings.
Dear How to Do It,
My boyfriend is one of those guys who says he likes oral sex, but he never orgasms from it. I’m not fixated on this; I know orgasm isn’t the end-all, be-all, and all guys are different. But I really love the sensation of bringing a man to climax in my mouth, him finishing there, and swallowing. He says he’s game for me to do my best, but it just hasn’t happened for him. I’ve never encountered this issue before personally, so I’m wondering what conditions will be most conducive for me to work magic. Should I spring it on him at sudden times so he’ll be caught up in the moment and feel no pressure? Have a technique checklist? Suggest he go a week without coming and see if that tilts him over? I totally get that this may never happen, but I want to have a game plan, since he seems down to try for it.
Dear Oral Direction
Is it the process that works for you? Or the seminal result? See, if it’s the latter, your issue is simple. Have him get close to orgasming—maybe while he’s penetrating you, maybe while he’s jerking off—and then get the tip of his dick in your mouth before the eruption commences. Boom. Delicious.
If the process is what gets you going, or the satisfaction of feeling responsible for this flood of semen, things get a little more difficult. Our friend the prostate may be able to help. Depending on how butt-shy the guy is, pressing on the perineum (also known the taint, that space between the testicles and anus) might add a boost to your blowing. If he’s chill about it, you might ask about pressing on his anus or penetrating him with a finger to reach the prostate from the inside.
But maybe your guy isn’t into that. That’s OK. You’ve still got the testicles and penis to work with. By now, you presumably have an idea of what your guy likes. Start experimenting. Run through all the different ways: sucking, tongue-flicking, squeezing, stroking fast, stroking slow, combinations of these tactics, and ways of stimulating a penis I’m not even thinking of. Make note of what he responds to most strongly. Find the range of pressures and speeds that seem most pleasurable, and ask for feedback.
I do think asking your dude to forgo ejaculating for a few days is worth a shot. When you’re both feeling ready, get in there and suck his dick like it’s your job. Suck it like you’re trying to get to the juicy center. Pull your hair out of your face. Use your hands. Touch every part of his body that you can reach and that he’s OK with.
You still might not get what you’re after, and if you do, you still might have to really work for it. Communication will be crucial. Without your boyfriend letting you know what’s feeling good or might make him ejaculate, you’ll be feeling around in the dark. But with proper communication, you will—at the very least—have a better understanding of how to make him feel great.
Dear How to Do It,
I’m the creator of, and an actor in, a forthcoming TV series. As it happens, I’m also dating one of my castmates. I’ve been thinking of writing a scene involving, um, physical intimacy between him and I, and although what I have in mind is fairly tame, I’m afraid of bringing it up. (My tolerance for doing vulnerable and even somewhat demented things on camera is high, but I absolutely don’t want anyone else to feel uncomfortable.) Any thoughts about how best to raise the issue?
Dear Screen Test,
Start with “Hey, what are your boundaries around sex scenes?” He’ll let you know whether that’s something he’s comfortable with at all. From there, if he’s open to the possibility, you can ask how he feels about performing a physically intimate scene with you, and both of you can discuss limits regarding what you’re willing to do on camera.
(If your partner is unable to set boundaries with you or be clear about his limits and “maybe” zones, you’ve got bigger problems and should probably reconsider.)
If he’s down to do the scene and you go ahead with it, be careful about respecting each other’s limits. You may even want to let the assistant director or someone in a similar position in on what the two of you have agreed to so someone else can flag it if things start to cross a line.
You also might consider going to a mentor or another experienced professional in the film industry for advice. Surely you won’t be the first on-set romance they’ve seen, and they may be able to save you a hiccup or two.
Dear How to Do It,
I’ve been married 24 years. I live in Alabama, Bible Belt. Problem is, I’m not really attracted to my wife anymore. There are a few factors, and I’m probably answering my own questions here, but I have too much resentment toward her over finances (she handles hers badly) and how conservative she is. I would love to have oral sex, but she isn’t into it, for example. Since she is so conservative, I can’t really relax during sex. Divorce isn’t an option because I know I’ll have to pay in court. When it’s all said and done, I want to find other women to carry on with, and that makes me the monster. If I knew where to go to find like-minded women, I’d do it. Maybe in essence, I want casual sex but have no idea how to find it. Any advice?
I don’t know where to find women who also resent their spouses and want to cheat casually. And since you don’t want to ask for a divorce, you probably won’t want to be caught cheating and find your conservative wife filing for one herself.
In case there was any vaguery, I’m not going to give you a blessing to step out on your marriage. It’s a tough choice, but I urge you to actually make one rather than sneak around and let fate decide. If you’re that miserable, isn’t your freedom worth a financial hit? Is the money more important to you than ever having a satisfying sex life?
Before it even gets there, though, have you made it clear to your wife that oral sex is important to you, and asked her to do it every once in a while? Since it doesn’t sound like she’s very sexually motivated, is there something nonsexual you can do to make her feel good, like a massage? This might even be something you directly negotiate—a monthly trade of oral for a back rub—depending on how you two feel about that approach. You’ve been married for a long time, but based on your letter, I wonder how connected and open you really are with your wife about her needs, and about yours.
More How to Do It
I’ve been married for about 10 years. About a year ago, I had a brief affair. We realized it was a mistake and ended the relationship. He lives far away, so I haven’t seen him since. Neither of us told our spouses about it, and we have no intention to. I’ve never done anything like that before, and I won’t ever again. I feel bad about it and wish it hadn’t happened, except in one respect: The sex I had with this man was off-the-charts amazing. Like, I didn’t realize that sex could be like that. Sex with my husband is fine—but I feel like I’ve been watching a black-and-white TV my whole life and I suddenly discovered Technicolor exists. I don’t want to go back to this ex, but I can’t stop thinking about the sex. I realized that I get very turned on by things that are out of my husband’s comfort zone. I can’t talk to my husband about it—telling him about the affair would only hurt him, and when this kind of topic has come up in the past, he has been very clear that if anything ever happened, he wouldn’t want to know. How can I get over this?