Head Games

I’m Alexander Cheves, a sex writer, worker, and educator. Friends call me Beastly. I answer sex questions. My debut book, an erotic memoir titled My Love Is a Beast: Confessions, will publish next month on October 12th.

I normally use this space to ask for support on Patreon — every dollar helps me run this site. But today, I ask you to pre-order my book. Pre-orders are shipping out now.

Come see me! We’re starting a book tour in partnership with The Advocate and Out Magazine. All events are free, but are ticketed to comply with local occupancy limits. Attendance will be limited due to the pandemic (proof of vaccination is required at all events), so get your tickets now. Most events will have a virtual component — follow my Facebook page and Twitter for updates.

I stumbled upon your tips for giving amazing Head while searching for an answer to my question. Superbly written article, btw! My question is, what feels best in general when the moment of orgasm actually occurs? I don’t have a penis so I’m not sure when he begins to cum. Do I keep pumping with my mouth? Sometimes there’s no choice as he grabs the back of my head and forces me to take it however he gives it but if he doesn’t do that I’m not sure if I’m ruining the orgasm by continuing to pump or if I should let him guide the whole ending. I never had a complaint about how I handle it but seeing as I don’t know how a penis feels when it ejaculates, its very difficult to figure out how to maximize the experience. I could be totally overthinking this and should just go with the flow, but I don’t want to give great head only to blow it at the end, all pun intended lol. Thank you and I’m sorry this went over the 200 words, but it’s kind of a complicated question.

Hi comrade,

I should probably tweak the wording on my Ask Beastly submission form.

For everyone considering asking me a question: Don’t stress over the stated word limit. I set it because I have gotten questions that are so long that they could fill several pages. With eight paragraphs of questions, it can be difficult for me to know what to answer, so the word limit helps me, and I believe it helps you, too. It’s a good exercise to try to distill one’s problems down to their shortest and simplest presentation. If you’re unsure how to approach this, consider focusing on a goal — however unattainable it might seem — rather than the problem(s) at hand. For example, if you’re dealing with some painful feelings about your monogamous relationship that you wish was a bit more open, it can be helpful to discern your desired outcome: “I want my partner to be okay with me having sex with other people.” Presented that way, you’ve already started working on your problem. You must have an idea of a solution before you can work for it.

I’m glad that folks feel safe spilling their most painful tribulations (and deepest, darkest desires) to me, so this advice on how to ask a question is not meant to dissuade anyone from doing so. It’s just me trying to help.

I’ve not mentioned this yet on this blog, but I have a business of “consulting” on matters of love and sex. I can’t call myself a therapist because I’m not licensed, but I do have clients who call me regularly to talk and pay an hourly rate for my time. This began as an extension of my sex work — naughty phone calls are part of the gig — but has become something more like therapy since the pandemic. If you feel you can’t express everything you’re dealing with in an email, message me via the contact form and tell me you’re interested in calling.

Now, comrade, on to your question. No two penis-wielding people are alike, so there’s no rule for what blowjob methods work best. That said, in most cases, when a person with a penis ejaculates, the tip (the head) becomes hypersensitive, and stimulating it at that exact moment can be un-pleasurable. I asked some dedicated blowjob masters their recommended practices for what to do when someone is cumming, or about to. They all consistently said that they stop “pumping” and take the cock as far back in their throat as they can or they pull off and let the love splash across their face.

This holds with my experience. I’m not a head master, but I sometimes like getting sucked off. When I cum down someone’s throat, I like to push in as deep as I can, hold their head there, and unload. Or I like to cum on their face. Either of these options is better than someone continuing to stimulate my dick — continuing to “pump,” as you say — especially if they like to linger over the head. When I’m close to cumming, my head gets too sensitive.

No matter what, I always say when I’m getting close to see if they want my kids in the first place. When I give oral service, I don’t really like eating cum, so I appreciate guys giving me a warning — I’d rather someone shoot on my face than down my throat. As a top, I always supply that courtesy and ask first.

Your impulse is right: let him guide the ending. Unless he’s a randy 22-year-old, most penis-bearers struggle to cum and have certain sensations that they know work best for them. This is why we often have to take it out and stroke for a bit to “work it back up” and to get close. Orgasming from oral is no different: he knows he what sensations his dick must feel in order to cum, so it’s probably best to let him take over when he knows he’s close. It also sounds like he’s a little dominant, so this appears to be the way to go for you. (Dominant throat-fuckers still need to negotiate limits regarding where they cum — in the throat or on the face — though they usually don’t say when they’re about to blow.)

That said, letting him take control is for someone exploring oral submission. If you want to be dominant and take control away from him — if you want to tease and milk him with your mouth — you can do that, and in that scenario you can use the hypersensitivity of the penis head to your advantage. Stimulating the head when someone’s close to cumming can almost be tortuous, and this is a method used by edgers and milkers within power-play scenes. Skilled oral dominants can drag out the pleasurable sensation for hours until they become nearly excruciating and their subs are literally begging to cum. This is really only doable if his hands are tied and if you know how to vary up the stimulation so that nothing starts to feel repetitive or taxing on his dick (raw, over-rubbed).

It’s not easy to know when a cock-wielding person is about to cum without them saying so. The skilled oral queens I talked to can sometimes tell when someone they’re sucking is about to shoot — they feel the cock get super hard and the muscles tense — but they still prefer a heads-up.

When in doubt, ask a man you know who gives oral sex for advice. It is widely known and agreed-upon — by gay and straight men alike — that people with penises give better blowjobs, because having a dick helps you know how to please one.

I hope some of this helps. Happy sucking.

Love, Beastly

I think my husband is a voyeur. He jokes about watching me engage in sex with another man/men while he watches from afar. Whenever we are out and other men ogle me, he remarks how he would love to see me sleep with them. He never mentions participating, only watching. I would gladly indulge him in this kink, as he has indulged me in mine, but I don’t know where to begin. And whenever I tell him that I would be open to this, he dismisses the notion and changes the subject. Maybe he’s scared? Maybe he’s ashamed? Maybe it’s a test?

Voyeurism is topical now with the recent Falwell revelations. Could you please provide some insight into this kink, and offer up any advice that would encourage anyone to fulfill their voyeuristic fantasies? Thanks.

Howdy friend,

My posts are scheduled in advance, so by the time folks read this they might need a reminder about the Falwell affair.

Readers: Jerry Falwell was a Southern Baptist televangelist in the ’80s and one of the most vicious anti-gay crusaders in history. He famously said, “AIDS is not just God’s punishment for homosexuals, it is God’s punishment for the society that tolerates homosexuals.” Thankfully, he’s dead, but his son is alive and is, of course, a Trump supporter and conservative pundit. As always happens with these people, it was revealed in 2020 that Falwell Jr. and his wife had an ongoing affair with the pool boy at a Trump hotel, a sexual relationship that started when the boy was 20 years old. Reportedly, Falwell Jr. liked to watch. The headlines delighted over this nonsense and the word “voyeur” was everywhere for a minute. I’m sure that media moment sparked an exploration into voyeurism for some people, but in most cases it was simply used for shock value and clicks, smearing and othering the kink community in the process.

I hate kink-shaming in all forms, even when the alleged kinkster is a homophobic Trump cultist. So let’s talk about voyeurism here with openness and positivity. Voyeurism is simply the fetish of someone watching others being naked or having sex. The counterpart to this fetish is exhibitionism — these folks like to put on a show. Voyeurs are often misunderstood as “peeping Toms,” people who watch others without their consent, but most voyeurs I know go to places where sex is happening (sex clubs, slutty bars, public cruising spots) and, by being there, the folks they watch have consented to being seen.

I would not encourage anyone to approach something in a relationship as a “test.” Tests are for students, not partners. Tests are trickery and manipulation. Assuming you’re not dating someone who does that (if you are, leave), take his response to your probing questions about voyeurism at face value: he gets uncomfortable, waves the subject away, and expresses disinterest. Regardless if he’s actually into voyeurism or not, this means he’s not ready for it, and that’s that. There’s nothing you can do to change his interest.

The only thing you can do is require your partner to be honest and forthcoming, even when subjects are uncomfortable. People who are unwilling to sit down and discuss things openly do not, in most cases, make good partners. It takes an amount of emotional maturity to talk and share, and you’re allowed to make that a POA — a price of admission, something your partners must do to be with you.

So rather than asking specifically about voyeurism, it might be more constructive to schedule a time to discuss your kinks and the areas you want to explore and ask him if there are any fetishes or fantasies he wants to explore. If he refuses to have this honest talk with you, that’s a red flag: there’s a difference between privacy and secrecy, and you should require honesty in your relationship, particularly in matters of sex.

If he’s willing to talk and, in talking, confirms that he’s truly not into voyeurism, you must take that at face value too and believe him. As with any relationship issue, the only thing you have is his word. If you don’t trust his word, it’s time to leave.

It sounds like there’s a part of you that wants him to be into voyeurism. Sorry, but if he’s not comfortable with it, there’s nothing you can do to change that — no one can instill a kink, interest, belief, value, or relationship goal into someone else.

Love, Beastly

quick question. do you have a go-to guide on how to approach your partner about an open relationship.

couldn’t find much online. and i thought it’d be easier because we’re gay but its actually pretty hard for me to bring it up

Hi there,

I have written something like a how-to guide on this very subject in The Advocate, quite recently. Take a look. Becoming open should, in theory, be easier for gay folks, though I think that has become less true as gay life has increasingly looked more like straight life. For generations, queer people were barred from the dominant paradigm, from media and jobs and representation, from marriage, and from all the old, vanilla standards that compose life as a heterosexual person. Because we were outlaws in their land, we created a new culture, a new world, one in which we normalized relationships of our own choosing and design, and thus queers were always at the vanguard of social movements like free love and the advent of leather culture. We have always been masters of “non-traditional” relationships.

Kids who come out now will see a different picture, and there’s some tragedy in that. It’s nice to have gay people on TV and in the music industry, but these things have absorbed us into the dominant paradigm and made us lose much of our underbelly, our impulse to live against the grain. We’ve been declawed. I imagine young gay men today will struggle with non-monogamy in ways their predecessors from past generations would have simply shrugged and gone with it.

I hope my article in The Advocate helps you reignite your countercultural fire.

Love, Beastly

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