Category Archives: manual sex

how to break your hymen – sincerely this time

To my utter astonishment, my tongue-in-cheek post about how to break a hymen without a penis has become one of the most read on the blog, due to people actually SEARCHING THE INTERNET for the phrase “how to break a hymen.”

And I feel terribly guilty that there are all these women out there who want to break their hymens and the advice they get from me is slightly facetious.

I still don’t know why people are so worried about it, but clearly they are, so here’s the ACTUAL advice:

Option 1: Have a medical professional do it. If your hymen is imperforate, microperforate, or septate, definitely take this option. If you don’t know whether or not your hymen is any of these things, get a medical professional to check. If you’re thinking, “But I don’t have access to a medical professional” or “I don’t want to talk to my doctor about this,” then there’s something else wrong that’s more important than your hymen.

Option 2: Have intercourse. It’s how women have been breaking their hymens for ages. There will probably be a little bit of pain and a possibly (but not usually) little bit of blood, but it’s totally no big deal, from a physiological/medical perspective. If your partner doesn’t have a biological penis, use a non-biological one.

Option 3: Break it yourself. Which means you need to know both how to manage the pain and how to successfully break it.

(Actually it’s not really breaking, it’s stretching.)

To minimize pain, use either (or both) a numbing agent (you can use oral numbing agents they sell at the drugstore for canker sores and stuff) or a counter-irritant. A counter-irritant is some intense stimulation elsewhere that more or less distracts your central nervous system from the sensation happening at your vagina. The best counter-irritants will be sensations to the other highly sensitive parts of your body, like your face, feet, and hands. Deep touch sensations – pressure, massage, vibration – will be most effective. So, for example, hold a Hitachi Magic Wand between your feet.

Drinking a couple of glasses of wine – more than one glass, but LESS THAN A BOTTLE – can also help. Do not, whatever you do, exceed 4 drinks, and no more than 2 or 3 in a single hour. Don’t be stupid about alcohol.

And to stretch the hymen, you mostly need girth. Gradually increasing the girth of the thing you penetrate with will make things easier; contrary to popular belief, pulling off a band-aid slowly results in less pain than ripping it off all at once, so don’t try to put a mango in there all at once.

Another thing to remember is that the hymen is just one of several potential sources of pain with penetration – indeed it’s just about the least common source of pain. The most common source of pain is friction. LUBRICATION is absolutely, positively, unambiguously CRUCIAL. DO NOT attempt to penetrate your vagina without LOTS of lubrication. If you really can’t get lube anywhere else, some oil from the kitchen will do.

Another potential source of pain is muscle tension. Yes there is a vaginal sphincter muscle, and you must relax it in order to penetrate the vagina. You can find it by stopping yourself mid-stream while you pee – it’s the same muscle (different sphincter. don’t worry about the details.)

And finally, pull out a little mirror and LOOK at your vagina and your hymen before you start any of this. LOOK at it. See where it is, what it’s made of. Think patiently and non-judgmentally about your feelings about what you see. It’s a part of your body, just like your elbow and your toes. Be as kind and gentle with it as you would with, say, clipping an infant’s toenails. Be nice to your body.

I can’t even begin to write about the psychological noise that must be happening inside a person’s head if they’re searching the internet for information on how to break their hymen. What advise can I give for that?

Take a deep breath. Relax. Pay attention to your body and its sensations. Pay attention to your feelings about your body, and know that you are allowed – indeed, you are WELCOME – to love all the parts of you. Okee dokee?

how to break a hymen without a penis

[EDIT: If you're looking for ACTUAL advice about how to break your hymen, read this post instead. The one on this page is more fanciful than helpful.]

EDIT 2: MYTHS! about the hymen – totally crucial to understanding your hymen.

So there was some confusion during my class tonight; we were talking about hymens and a couple students asked about, like, how big something needed to be to break a hymen, and I was all like, “Well, that depends how sharp it is.”

Because I have a habit of answering precisely the question that is asked, I had no clue (until a student generously came up to me after class and explained) that what they were actually asking was, “Suppose a woman has pain with penetration, due to her hymen, but there’s no one with a penis she’s interested in having break it. What’s a girl to do?”

OHH! Well heck, next time just say so! Didn’t I spend 10 minutes at the start of class explaining that this is a sex-positive safe space where no yucks are allowed and everything is okay? Look, all I want in life is to give people the sexual health information they want, so just ask!

Anyway, the answers to that question are:

(1) Very carefully
(2) With a little help from your friend(s) and
(3) Make a night of it.

There’ll be some pain – heck, the pain is the reason you’re doing this, right? And the key to managing that pain is to close the gate by overriding the pain signals with OTHER sensations. You know how when you stub your toe, you rub it? That’s closing the gate – overriding the throbbing sensation with the rubbing sensation.

With loads of sensation elsewhere – and I’m thinking a vibrator on the clit, another on the anus, breast stimulation, inner thigh stimulation, feet stimulation, lots of OTHER sensations – you can reduce the pain sensations.

So. Have a partner… or two… or three… or more, to help you out. Get warmed up, very aroused in whatever way works for you.

Because there’s no certain answer to the question, “How big and forceful must a penetrating object be to break the hymen?” I suggest fisting as the foolproof strategy. Fisting is a whole post in itself, but in brief, you begin with just one finger and gradually increase penetration until your whole hand is in the vagina.

Once you’re well-aroused, your partner (using plenty of lube) begins penetration with just one finger. Keeping a palm or a vibrator over the clit, maybe with pressure on the pubic bone, they maintain sensation elsewhere during the penetration. Go slow. Keep that degree of penetration until it’s comfortable.

Add a finger. Increase stimulation elsewhere – like add inner thigh stimulation to the clit stimulation. Keep that degree of penetration until it’s comfortable. Remember lube!

Add a finger and increase stimulation elsewhere. This will be your three longest fingers, which you should sandwich together, with your middle finger on top and your ring and index fingers touching at the tip. Penetration will thus be narrower at the top than at the base of your fingers.

Breasts and feet and lips are excellent targets of stimulation at this stage. (You begin to see why having multiple friends involved can be handy!) Keep that degree of penetration (plus additional stimulation) until it’s comfortable.

Add a finger, a pinky tucked up against the other fingers, and further increase stimulation elsewhere. Well-lubricated external anal stimulation in addition to clitoral, inner thigh, breast, feet, and lips, for example. Also fantasy and talk. Keep that degree of penetration until it’s comfortable, from the narrow tip of the middle finger down to the broad base of the fingers.

Now your partner tucks their thumb against their palm and penetrates past the last knuckle. Lots of other stimulation, closing the gate. Vibrators on clit, anus, and breasts, a mouth kissing your mouth, another mouth on your earlobe, another mouth sucking your toes (which will be curling by now).

And that, my friends, is how you break a hymen without a penis. Carefully, with a little help from your friends, and making a night of it.

Take lots of time and use lots of lube and make sure you maintain a high level of arousal with clitoral, breast, thigh, and other stimulation.

Let it be ritualistic and important, like a birthday. After all, for all that the hymen/virginity thing is bullshit, if you’re breaking your hymen in order to expand your sexual horizons, heck this is a moment!! Make it a night to remember.

bend it like Beckett

Here is a handjob tip that causes people’s eyes to widen and their heads to tilt thoughtfully to one side.

As I’ve mentioned before, the shaft of the penis extends deep inside a man’s body. Much can be done with this fact.

So why not do this: once he’s got his erection, lay him on his back, lube up your hands, and start the clock. What I mean is, using upward strokes and alternating hands (right, left, right, left), point his cock toward his chin. Bend it right down so it’s nearly parallel to his body.

Then rotate, point it toward his shoulder (right, left, right left – go slow, be fairly firm),

then toward his hip bone (right left…), there you go, well done,

then to a 90° angle, toward his hip, then down toward his thigh, then straight down toward his feet, and around again up the other side.

Like his body is a clock face and you’re rotating the “big hand” around 12 hours. Gradually. With upward (as in, from base of penis to head of penis) strokes, alternating hands. And plenty of lube.

Feel free to include some wrist-twisting, if you feel it’s appropriate.

What this does is bend the shaft where it meets his body. This feels very interesting and good. You may notice that he’s particularly sensitive or responsive pointing in one direction or another. Tuck that information away for future use.

A slightly advanced technique, for those who feel they’ve mastered the basics: don’t grip the shaft in your fist, like you’re gonna lead a marching band with it; instead, allow the palm of your hand, your thenar eminence to be the primary source of contact, and curl your palm around the head of the penis, just resting your fingertips over the frenulum, which is exquisitely sensitive to light touch. While’s he’s rotated toward your right, it’s the right hand you’ll do this with; toward your left, your left hand. But you’re alternating hands, yeah, so when your opposite hand strokes upward, it’ll be an entirely different sensation – with the palm of your hand against the frenulum instead.

When you’re using this technique, use the hand that’s not stroking to press the shaft, near the base of the penis, in the desired direction. The combined sensation of the deep-touch bending and the light-touch stroking is very lovely and fine.

You can also try using your hands and your mouth. It’s a particularly excellent strategy for folks interested in preventing choking: you vastly decrease the risk of accidentally getting him too close to the back of your throat if he’s not pointing out, perpendicular to his body, but rather pointing down to his toes or flat against his belly or over to one side.

A further benefit of the “pointing toward his toes” position is that you can look up at him quite easily. Which is a pleasant and friendly-like thing to do.

So there’s a little something for you, to make your weekend move along with a bit of a swing.

(What has this got to do with Beckett? Well. If you do it right, it’ll seem surreal, and also he’ll feel like he’s about to meet Jesus. But mostly I just thought it was an entertaining [if elitist] title.)

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?

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.

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!