Category Archives: oral sex


I have had a totally INTENSE past few days. On Thursday I did a talk on positive sexuality that resulted in a half dozen women in their 40s, 50s, and 60s, discussing places to find women-friendly porn and erotica. Totally great.

And I gave about 15 seconds of advice about fellatio (“Don’t neglect the scrotum as an option – not all men like it, but some men REALLY like it, so give it a try.”), which resulted in the question, “Where can I find more about that, about… you know?”

(Why, my little Fellatio Guide.)

The thing for me: how do you get to your 40s, 50s, and 60s without knowing to try the scrotum? Who can’t go to a bookstore and look in the sexuality section – and especially now, who can’t just google “feminist fellatio” or whatever? How can it be that there are women in America who don’t know that good, women-friendly, sex-positive information is readily accessible? How do you get to middle age without knowing where to go to get it? What would be missing to prevent that?

I think most of what would be missing is confidence. Confidence to try new things without worrying about “getting it wrong,” as though it’s possible to get anything “wrong.” Confidence that looking like a porn star is not required to give head like one. BETTER than one.

Which makes me cry, how do you teach confidence!? How do you learn it?

I talked to someone else on Saturday, an old friend who has broken through a whole lot of psychological noise to get to brand new a level of openness and creativity and pleasure in her sexuality. How did she do it? I asked, and she said she just… decided she’d had enough of worrying about whether or not she could please a man, whether or not she was adequate. She just let it go, the decades of negative messages.

Crikey! Talk about power!

I suppose it’s a readiness for change thing: when life has prepared you to change, you will. Before then… you’ll stay stuck. But I suppose folks who read the blog are ready. Folks who find and read the fellatio guide are ready. Which means that I never see the people who aren’t ready.

And I forget how far many people have to travel before they get to healthy joyful sexuality. I forget how revolutionary it is to suggest that your body belongs to you and no one else, that you’re allowed to do ANYTHING you want in bed, and that your own enjoyment of pleasure – your own and your partners – is the one and only measure of success?

How do we get them ready?

make a penis happy

Enough with the political blah blah blah, eh? How about some straight up Sex Advice for Having Better Sex? Here’s one for the folks who have sex with people who have penises.

It’s one that I always think everyone knows and then I’m surprised when it turns out people don’t. Quite simple, but it can make all the difference:

When you’re dealing with a penis, squeeze up, relax down.

Squeeze up.
Relax down.

Whether using a hand or a vagina or a mouth or a mechanical device…

Squeeze up.
Relax down.

(Not so much with anal sex, you mostly just want to let the anal sphincter relax during penetration.)

Squeeze up.
Relax down.

With manual sex, a wrist-twist is a very fine thing to add, especially swirling over the head, where the bulk of the nerve endings are clustered.

With the vaginal muscles, you relax as he (or you) thrusts in, and squeeze as he (or you) pulls out.

With oral sex, you suck on the up, and relax a bit on down. This is particularly useful because it can save wear and tear on your jaw, so you last longer. (Really you should save the sucking for the very very end, and use your hand on the shaft throughout the blowjob.)

Squeeze up.
Relax down.

It can make all the difference.

The reason it works is straightforward mechanics. The shaft doesn’t end at the pubic bone; it extends deep into his abdomen, like this:

penis anatomy

Squeezing up tugs the whole shaft, which feels nice. Squeezing down would sorta jam all that extra, interior shaft down into his body, which, ya know, doesn’t feel as nice.

Squeeze up.
Relax down.

Makes a penis happy. And when the penis in your life is happy, doesn’t the sun shine just a little brighter?

excellent torture

I’ve been pretty heavy on the nerd lately, and not paying as much attention to the sex. Let’s fix that.

How to maximize your torment of your partner.

Haven’t you wanted to be in that position of power where you stand at the gate of your partner’s orgasm, tempting them gradually closer, then wickedly slamming the gate in their face and sending them to the back of the queue, only to draw them, even more eager, forward, over and over, until they hate you and love you in equal measure and they can’t think and can’t move and are begging you in choked gasps in end their torment?

Sure you have. Here’s how.

When you partner is at the breath-holding stage of the proceedings, that indicates that waves muscle tension are causing the contraction of both the thoracic diaphragm and the pelvic diaphragm. If that sentence made no sense, don’t worry, just notice that your partner has gotten to the breath-holding stage of the proceedings. Each held breath slightly escalates tension, edging your partner closer to the threshold of orgasm (which is not a fixed point, but don’t worry about that for now).

When giving beginner advice, I generally say that breath-holding is exactly the time to KEEP DOING EXACTLY WHAT YOU’RE DOING. Same speed, same pressure, same everything.

For the more advanced student, you can use this phase to take the reins of your partners orgasm.

Necessary Supplies. In addition to the confidence and joy necessary for all excellent experiences, it requires a great deal of attention to muscle tension and breath. Those who practice mindfulness will therefore be better at this than everyone else because they’re trained to be more sensitive to sensory stimuli and I therefore suggest that all of you start practicing mindfulness meditation every day for the rest of your lives. (Also, with dudes you can pay attention to genitals as well as breath and tension. Not so much with chicks.) So:

Your supply list:

  • Confidence
  • Joy
  • Your willing, relaxed partner
  • Well-tuned Attentiveness to your partner

Arritey. Now.

Step 1. When they’re well entrenched in a pattern of breath-holding, notice how long your partner is holding their breath. (If noticing how long the breath is requires counting seconds in your head, that’s okay, but ideally you’ll be so intuitively connected with your partner that you don’t need to count. You just KNOW, you know?)

Step 2. When your partner is approaching the end of a long breath-hold – so they’ve been silent for, what, like 8 seconds-ish, that’s when you STOP. Make it nice recognizable full stop so they don’t think you’ve just made a mistake or are changing position or whatever. Just stop. Keep physical contact with them – if this is oral sex, keep a hand on their thigh or something; if it’s penetration, stay totally still but make direct eye contact.

You stop at the END of the held breath, because tension is at its maximum then. If you stop after they’ve released a breath, they’re already on a down-wave of arousal and you’re not interrupting anything.

Step 3. Wait. Without breaking contact, watch the tension ease from their muscles and face, listen to their breathing steady. If they ask what you’re doing, lie. Say, “Nuthin’” or just smile at them or say “takin’ a break” or “What are you doing?” If they say “I was about to come,” that indicates that your timing is SUPERB; feel free to boast about this. Give your partner a villainous grin and say, “Yeah I know.”

Step 4. Start again. When they’re less definitely aroused (but still SOMEWHAT aroused), start again, slowly at first. Gently. Gradually increase intensity. When they get back to a stable breath-holding rhythm…

Step 5. Near the end of another held breath, stop again. Stop. They may, at this point, give you a dirty look. That means you’re doing it right. Be sure to answer their glare with a smile. Shows you’re friendly. We don’t want open hostility after all.

Step 6. Wait again. Watch their arousal dissipate. Allow time for dirty looks, questions, bafflement. Be sure to stay in contact, physically and emotionally. Run your hands over any number of body parts not ordinarily considered “erogenous.” (Remember, arousal is context dependent, so by the time you get done, EVERYWHERE will be erogenous.)

Step 7. Start again. You may prefer to start VERY INTENSELY this time, to switch things up, keep them guessing. Or not. You decide. Don’t let anything your partner says sway you – unless you want to.

Repeat Steps 5-7 as long as necessary/fun/physically tolerable/your partner doesn’t grab you, pin you down, and either beat the shit out of you or torture you in return.

The art of this strategy lies in the management of your partner’s arousal level. Pay close attention, feel their arousal without becoming so aroused yourself that your judgment clouds.

Something to note: The longer you continue, the more slowly their arousal will dissipate and the faster it will return. Eventually you’ll be able to do almost nothing and send them instantly to the tearing, thrashing edge. That’s fun. Also, the longer you do this the more intensity they will (probably) be able to tolerate, so feel free to escalate if you like.

There you go. Some (nearly) science-free sex stuff. Happy Wednesday.

(Note: I recently learned that my mother regularly reads the blog, so I would therefore like to make it clear that I never have and never will do anything like what I’ve just described. And preemptively let me say: shut up Bill, that’s not funny.)

a burst of shameless self-promotion

Hey folks, I’m excited to be able to say that The Good in Bed Guide to Orally Pleasuring a Man is available in PDF and formats compatible with iPad, iPhone, Android, Blackberry, etc as well as Kindle.

And it’s only like 6 bucks!


I almost never ever write about fellatio, so if you want to know what I have to say on the subject, this is pretty much to way to do it.

Mine is the first guide available at Good In Bed, which is a site organized and edited by Ian Kerner of She Comes First fame.

So that’s all very exciting.

what women want (12): leave that clit alone

Women want…

… well, some of them want you to leave their clitorises WELL ALONE.

Have I mentioned lately that WOMEN VARY? One of the ways that women vary is in the directness of clitoral stimulation that they enjoy/can tolerate.

Some women are enthusiastically pro-diddle – they are strongly in favor of you planting a fingertip lightly but firmly just south of the glans clitoris and bobbling it rapidly up and down. Indeed, you may feel very pleased with yourself that you’ve found that a flicky tongue along the clitoral shaft can get your gal to the heights of ecstasy – very good, congratulations – but if that relationship ends and you find yourself with a new woman, you CAN’T assume that what worked for Lady A will also work for Lady B. Lady B might HATE IT when you flick her clit. Lady B may want you to leave the clit utterly alone and run your tongue in soft circles along her left labium.

For women like Lady B, direct stimulation can be irritating or even painful. Direct stimulation like that is way, way, way too much. You can’t know until you get there (or until she tells you, which is even better) whether or not she’s a direct stimulation kind of gal.

One clit-related truth that is nearly universal (of course nothing is truly universal among the female-bodied) is that you must pre-heat the oven, as it were.

This one Monty Python got genuinely right:

“What’s wrong with a kiss, boy? Why not start her off with a nice kiss? You don’t have to go leaping straight for the clitoris like a bull at a gate; give her a kiss, boy!” Then: suck the nipple, stroke the thigh, nibble the earlobe, knead the buttocks, “and so on and so forth. So we have all these possibilities before we STAMPEDE towards the clitoris, Watson.”

All in aid of getting the “vaginal juices flowing.” (Except of course we all know by now that just because a woman is well aroused doesn’t mean she’s necessarily well lubricated; and vice versa.)

A decent rule of thumb is to begin peripherally, delicately, and slowly, and gradually work your way closer to the clitoris, with increasing intensity and speed. Just HOW close, intense, and fast will depend on the woman, and will vary greatly from woman to woman. You have to play close attention to her arousal level and get all the feedback she’s interested in giving you.

(This is a classic men-women difference. With guys – again it’s not universally true, but it’s a decent rule of thumb – you can accost him after a shower and just put his whole, soft cock in your mouth if you like; you’ll catch him off guard, but the penis doesn’t need the warm-up act in the way the clit does.)

Context, context, context. Create a sexy context first, then commune with the clitoris.

questions that don’t matter (1)

I firmly believe there’s no such thing as a stupid question.


That doesn’t mean that all questions are important. There are a lot of questions whose answers just don’t matter – especially questions about sex. There are all these deeply unimportant questions that people are burning to ask, because these are the questions the ridiculous media present as being important.

People ask them all the time and I try REALLY hard not to roll my eyes or sigh heavily or otherwise indicate how little I care about the answer, how little the answer will make them healthier or happier, and how little the answer will make the world a better place. I’ve got a list of them, these questions that don’t matter.

Here’s one:

Is oral sex/anal sex/manual sex “sex”?

Who fucking cares what “sex” is? Why does this matter? Why is it important that 80% of young adults don’t think oral sex is sex? So what?

The claim I hear to justify this question is related to prevention of STIs: if a teenager doesn’t think anal sex is sex, won’t that mean they think they can’t get a sexually transmitted infection?

I have yet to see a single study that indicates that identifying a behavior as “sex” increases the likelihood of using protection with that behavior. If you know of that study, PLEASE, for the love of mike, send me a link. Until I see such evidence – and I doubt I ever will – I’m bored out of my mind by this question. I just don’t care if oral, anal, and manual count as “sex.” I’ve never seen any evidence that these artificially imposed categories are important from a (physical or mental) health perspective.

The important question, instead, is “Are there any STI risks associated with oral/anal/manual/vaginal/whatever sex?” So ask that one and report about it. The answer would tell us a lot more about what young people do and don’t know, and tell us more about what we need to teach them.

I’d like to take this opportunity to add that, in fact, manual and oral sex, while not remotely “risk-free,” ARE lower risk for STI transmission than penile-vaginal intercourse and they are superb contraception. So from a harm reduction perspective… right on.

EDIT: It is a strange and bewildering coincidence that the same day I post this, Heather Corinna’s very thoughtful article on “What’s Sex” was also published.

Orgasm 10: simultaneous

(Apologies in advance for the heteronormativity of this post. Simultaneous orgasms are easier for same-sex couple because they aren’t necessarily facing the same biological differences that curse the straighties. Not to say they’re EASY for same-sex couples. Just a bit less difficult.)

Romance novels and movies are awash in simultaneous orgasms. Hero and Heroeen (read that like you’re Dudley Do-right) cross that exquisite threshold, launch themselves willingly over a trembling edge, and tumble downward in a spiraling, panting tangle of sheets and sweat and oxytocin.

Boy howdy, right? It’s terribly compelling, terribly romantic, this notion of fusing so utterly with your partner every barrier is shed, every defense is dropped, and your bodies lock into each other’s arousal. The boundaries of your very skin becomes permeable and you – almost literally – merge into each other, like the entrainment and synchronization of two rhythms or the joining of the Blue Nile with the White Nile or the microscopic union of egg and sperm giving rise to one new life or… whatever metaphor gets you.

But in real life, simultaneous orgasms are, like, hard. Both for emotional reasons and for straightforward mechanical reasons.

As we know from this weekend, there are some differences between men’s and women’s orgasms. Specifically, women take longer to orgasm and are less likely to orgasm from penile-vaginal penetration.

And if the goal is for two people to have an orgasm at the same time, then how long it takes you to come and what kind of stimulation gets you there, well those are things you need to be able to match up.

You need three things: You need a high degree of control over your own sexual response. You need a modality that provides enough of the right kind of stimulation to get you both to orgasm. You need a minute awareness of your partner’s level of arousal. Control, modality, attention.

This is the easiest of the three. If you read this section and go, “DUDE that sounds HARD!” perhaps the time is not yet ripe for you to pursue simultaneous orgasm.

Gentlemen: please teach yourself to maintain a high level of arousal without ejaculating. If you can stay pretty darn aroused for half an hour, that’s a good start. An hour is better.

Ladies: please teach yourself to masturbate with your hands efficiently and reliably. If you can come reliably in 20 minutes, that’s great.


I’m gonna say there are two primary modalities for simultaneous orgasm. There are more, of course, but let’s simplify a bit.

PENETRATION. If you’re one of the 25-30% of women who are reliably orgasmic from penetration, this will be a little simpler for you. If you are instead in the majority of women, we need to find a way to add clitoral stimulation to your intercourse. Lots and lotsa ways to do that:

  • Your hand on your clit
  • Your partner’s hand on your clit
  • You holding a vibrator on your clit
  • Your partner holding a vibrator on your clit
  • Sandwiching a vibrator between your two pubic bones
  • Angling penetration so that your partner’s pubic bone rocks against your clit (them on top)
  • Angling penetration so that your clit rocks against your partner’s pubic bone (you on top)
  • Your partner straddling your thighs so you can cross your ankles and grip your thighs together during penetration

You may also find that adding anal stimulation gives that extra oomph you need to have an orgasm during penetration. Try a buttplug (just plant ‘er gently in there and leave it be during intercourse) or have your partner use a finger on or in your ass during intercourse (may require long-armed or flexible partner).

All kinds of other stimulation can be useful too. Breast stimulation. Kissing. Hair touching/pulling/gripping/etc. Face and/or throat touching. And any number of psychological dynamics that might intensify the experience for you – pinning your partner down or allowing your partner to pin you down, fantasy and role play, a sexy venue… careful, though, that these add to your arousal without distracting you so much that you lose track of your partner’s arousal.

69. Mutual, simultaneous oral sex can potentially generate simultaneous orgasm. In some ways it might be easier – women may be more orgasmic from oral sex, and fellatio in particular gives you bunches of information about your partner’s arousal level and lots of control over how aroused you let him get, so you can make sure he stays on pace with you.

The trick with 69 is that it’s difficult to split your attention between what you’re doing and what’s being done to you. This diminishes as a problem if what you’re doing is just about as arousing as what’s being done to you. In other words, it’s easier to have an orgasm during 69 if you’re as aroused by the sensations of your mouth on your partner’s genitals as you are by the sensation of your partner’s mouth on your genitals.

I’ll get into more detail about attention soon. For now, begin practicing experiencing your partner’s genitals in your mouth, and their body’s responses to that, as part of your own arousal.

I’ve left this for last because it’s potentially the most difficult.

A common barrier in all orgasm challenges is mindfulness, paying attention to what’s happening in your body to the exclusion of anything else (e.g., not thinking about your fat, your kids, your to do list, your boss [except under sexy circumstances], or your car, instead of thinking about sex whilst having sex).

Attention is an order of magnitude more difficult during simultaneous orgasms because you have to pay attention to both your own and your partner’s arousal. I mean you have to pay all the necessary attention to yourself to get yourself to orgasm, AND you have to monitor your partner’s arousal, to get the timing right.

The people who find simultaneous orgasm easiest are probably people who find their partner’s arousal level to be highly, highly stimulating.

Fortunately, this is learnable. Begin practicing paying attention to your partner’s arousal level, and to experience it as a part of your own arousal. Imagine what it might feel like to be in their skin, what they must be feeling. Allow their arousal to feed and merge with your own arousal.

At this point, we get into the psychological part of it. At this point, you begin to shed the “my body/their body” dichotomy. At this point, you begin experiencing her skin as your skin – you feel both the firm softness of her abdomen under your hand and the warm pressure of your hand as she is experiencing it.

You live in two bodies at once. You feel with two bodies at once.

This is majorly advanced empathy. Most of us have experienced at some point – some of us experience it regularly, but most people have to work at it.

It’s good for you, this body empathy, like vegetables and jogging and 8 glasses of water a day – but more, it’s enriching, like a Jackson Pollack viewed with your nose 4 inches from the canvas, like Mozart, like a brand new idea. It’s good for you. Do it. Try it.

To conclude, allow me to say that this is all Extra Bonus Sexy Fun. Having or not having simultaneous orgasms is no reflection on your sexual health and wellness.

I think it’s worth trying though. What makes simultaneous orgasm so compelling, I believe, is the abandonment of the barriers we so often use to defend ourselves, to maintain our sense of identity, of separateness from others. It’s our task as adults to stay over our own emotional center of gravity, and simultaneous orgasm is about falling into each other at the bifurcation point between order and chaos, at the pivot between control and abandonment. It requires skilled neglect of your own personhood and precise, focused joy in your partner’s. In other words it takes practice.

Happily, every occasion that you practice can potentially improve your life and relationship – not just your sex life and sexual relationship, but your whole life, your whole relationship. It’s good. I think you should try it.

beauty… again.

Yes, my bit there last week about male beauty begs the question, “Is quaffed perfection what men want?” If it’s not true that straight women want the lapidary man of magazine covers and romance novels, could it be that men also prefer their women a little unkempt, a little degagee in their body maintenance?

Answer: yeah, could be! A recent Australian study apparently found that men prefer the average body size of ordinary women, around an American dress size 10 or 12, to the superskinny ideal we’re trained to venerate.

A substantial body of research about heterosexual men shows that men’s beauty judgments of faces are shaped by the faces they’re exposed to. In other words, men like what they see, and, no matter how media-saturated the culture may be, they still see more actual real women than images. So they like women, not perfection.

There’s other stuff that seems to be more or less hard-wired, like waist-to-hip ratio and facial symmetry, all generally indicators of health and fertility. (NB: That 10-12 dress size equates roughly to a 25ish BMI, technically “overweight,” yet associated with the longer lifespans than the obese, the underweight, or even the “healthy weight.”) But in the industrialized world of the twenty-first century, the superabundance of nutrition and medicine means nearly all of us pass muster on the fecundity front.

Anyway, I don’t think men pay close enough attention to tell the difference. If there is even one woman out there, even one, who has had a real life experience like they show in the movies, where the guy actually notices what it took you two hours, four gallons of hair product, and an industrial strength slimmer to achieve and then bursts out breathlessly, “Wow,” or “You’re so beautiful!” you must tell me. As far as I can discover, no woman has ever had her intensive grooming efforts explicitly noticed by a man without some kind of prompting.

Perhaps the straight ladies of the world long to believe that efforts to conform to some fictional standard of beauty will result in actually being more beautiful to the men in our lives… but the men in our lives aren’t too fussed about it.

See, c’z you know what men like? They like us in our bathrobes, dewily pink cheeked after a glass of wine and a soak in the tub, and actively interested in giving them a blowjob.

And that’s how it should be.

anatomy boggle redux

Purlicue. This isn’t quite a body part, it’s more a gap in body parts. It’s the space between your thumb and extended forefinger – it’s the L that indicates your left hand. It can also mean “a curl or flourish in writing.”

This is an absolutely crucial body “part” in the context of hand jobs and fellatio. That space right there? There’s magic there. The curl of your fingers around it, the flourish of your wrist, can turn that empty space into an adytum, the innermost sanctum of worship. Subtle changes in pressure, shape, movement, or lubrication can drastically alter the penis-owner’s experience, giving you unlimited variety and control over your partner’s arousal. Master the artistry of the purlicue, my friend, and you’ve mastered the cock.

Purlicue. You’re never gonna forget now, are you?

God how I love the English language. :)

PS – 5 points, children, if you can remember last week’s word without going back to look!