My name is Alexander Cheves. My nickname is Beastly. I write about sex.
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Your blog content is wonderful and I’m a fellow New Yorker. I’ve been dating my boyfriend for a year. It was just our anniversary last week!
I’m a top and not well versed in oral sex, which has been a point of friction throughout our entire relationship. He’s been frustrated with me as he gives me tips and I’m still not performing how he’d like me to. I’m worried this could potentially end our relationship or cause him to cheat if he’s unsatisfied.
He gives me amazing head and I’d like to return the favor. He says the biggest turn-off is that he doesn’t feel that I’m into the head, but the truth is that I’m so afraid to not please him that I get into my own head.
My past relationships were casual and I never performed oral sex on my partners. I’m sort of a virgin in this area. Any advice you can share would be helpful. PS – he’s into leather, so I bought handcuffs, a ball gag, and harnesses to use during our anniversary trip this weekend to Montreal.
My first question is: Do you like oral sex — or, at least, are you turned on by the idea of giving head?
That’s key. The best blowjob gods are simply guys who are very turned on by the idea of sucking cock. If that fantasy isn’t part of your erotic headspace, you may simply not be a fan of oral, and that’s totally fine.
Confession: I’m not a big fan of oral sex. It’s just not my thing. And if any guy I was dating made me feel like I was somehow inadequate or my sexual offering unsatisfactory — if he made my disinterest in oral sex feel like a dealbreaker for him — I’d leave him immediately. I won’t mold myself to be what my partner wants. Someone must want me exactly as I am or hit the road.
Let’s get something out of the way: If you really, truly fear your boyfriend will leave you — or, worse, cheat on you — because you don’t give him the oral sex he wants, you should leave him. Pleasure in sex is always a two-way street.
Now, if he’s simply expressed that he likes the idea of oral and you want to satisfy this for him — if this desire is coming from you, not him — and you’re getting some performance anxiety, that can be dealt with by practicing, sharing feedback, doing research, and trying some tips.
First: practice. All sex requires practice and training. No one is magically able to do anything sexual, because sex is complicated and difficult. It sounds like he’s been giving you some feedback already about what he likes, so it sounds like you’re getting some practice. Keep practicing and maintain patience with each other. Focus on “I” statements like “I loved when you…” or “I really liked the part when…” instead of “you” statements, which can increase pressure and feel accusatory (“You aren’t really into it and I can tell”).
A radical truth that people forget is that no one can make anyone feel a certain way — feelings (pleasure, pain) happen in our bodies, in our minds. They are fully self-contained. This means that even for a heavy submissive, pleasure is always, to some extent, active: they are actively giving someone else control which makes them feel pleasure, which is an experience that happens fully within their own body — pleasure is not “done to” them. (This truth is generally more employed in the service of navigating emotional feelings, not physical ones; a fighting couple can benefit from being reminded that we must own our thoughts and emotions because they are fully ours, contained within our bodies, and are not generated by the actions of someone else — and can be fully independent of what others say or do to us.)
In less cerebral terms, this means that it’s a fallacy to say, “You made me feel X” or to believe that someone else is capable of controlling your emotions. This is a lesson for him: Pleasure is active, so if he’s not enjoying your oral service, something is happening in him that’s not enjoying it, which he needs to take ownership of before critiquing you. Knowing this can make practice more productive and can help get out of your head — the blowjob success doesn’t depend fully on you.
Second: research. Look up blowjob tips online. I wrote one such article for The Advocate. Maybe talk to a friend who really loves giving head and considers themselves a head master. If this is really an issue that could drive a wedge between you and your partner, talk to a sex therapist.
Lastly: try my few tips. I am not particularly great at oral, nor have I ever particularly enjoyed it, but in the last year or so I’ve made a focused effort to improve, and the first step of that for me was to start watching blowjob porn, an area of porn I completely overlooked in the past, and trying to masturbate to it (it’s worked, particularly as I, in true kinky fashion, have explored more hardcore oral videos like skull-fucking, throat training, and so on). This is simply me building up a picture in my mind, a fantasy of oral that isn’t an obligatory and tiresome preamble to anal but a complete sexual experience in itself.
The second step for me happened by accident: I met someone who wanted to train me for oral service and has taught me some practice exercises.
First practice exercise: With your chin up and your tongue out as far as it can go, take a small dildo and gently touch the head to the tip of your tongue. Treat it like a real dick, and very, very slowly drag the head of the dick up the middle of the tongue about an inch, then stop. Then, keeping the dildo in the exact spot on your tongue, start to close your mouth, a movement that will naturally withdraw your tongue and pull it in. If that dildo stays where it is, when you close your mouth around it, it will already be in your throat — you’ll have naturally “pulled” it in. This exercise can help with a gag reflex and can be done with a partner.
The other exercise is also done with a partner — this one is meant to foster trust and connection, two key components of any rewarding erotic experience. Get on your knees on the floor (I recommend putting folded towels down so you don’t hurt your knees) in front of your partner and keep your hands held tight behind your back (pretend in your mind that they are tied). Go as far as you can on your partner’s cock — and then have him take slow steps back, holding your shoulders firmly. Keep your upper body rigid. You will tilt forward and you will feel your core and abs activated. Trust him to not let you fall. (You can’t easily fall because his cock is in your throat, literally supporting you up, and you can’t fall “through” his physical body). You’ll find as you trust him and tilt further forward that it becomes easier to take his cock in your throat because your neck and throat will be extended and opened up, creating a straight tunnel.
The fact is, it’s easiest to swallow a dick when your head is tilted back, which is why some guys lay on their backs on the bed with their heads over the edge, to create a straight tunnel for face-fucking. The same ergonomics apply here with the added benefit of building trust: the more you trust him and lean forward, the deeper his dick will slide in your throat, with less pain. I don’t actually suggest tying your hands in case you actually do fall forward and need to catch yourself. As you tilt forward, your impulse will be to put out your hands in front to brace you from hitting the ground, but doing that defeats the purpose of the exercise — try to see how far you can go.
That’s the best dick-sucking advice I have. Even with these new practices and renewed interest, I’m still not likely to hook up with someone solely to suck cock, because it’s still not my favorite thing — I’m a butt-focused person. If you just don’t enjoy sucking dick, don’t force yourself.
It sounds like he’s pressuring you a bit, which is not constructive and is the surest way to ruin sexual chemistry. Why do you have to be good at head? Why can’t that be his thing?
I gave you some tips, but I want to impart something important: You are a full sexual being and not lacking in any way. There’s no rule saying you have to perform a certain sex act at his skill level or at the level he wants. If he doesn’t like what you offer, that’s fine, but he probably shouldn’t date you. If he needs great head to stay in this relationship, the relationship is not worth preserving.
Lastly: consider opening up your relationship a bit (you used the word “cheating” so I assume you’re monogamous). Non-monogamy could solve this problem and make everyone happy, as it does with most relationship issues.
You could give your partner permission every now and then to get a world-class blowjob from a hungry cocksucker who wants nothing more than to milk a load with his throat. You probably wouldn’t feel comfortable watching that, at least not right away, but I can tell you that, as someone who enjoys non-monogamy, it can be beautiful to watch someone I love enjoying an experience with someone else that I can’t provide them. Watching lets me be part of that fantasy without having to directly supply it, and that might be a beautiful experience for you, too.