What’s the worst sex you ever had?

Now imagine having it for a decade.

Dear Chloe,

You’re going to lose your virginity tomorrow. That’s the expression you use, because although you’re a baby feminist, although you read The Beauty Myth and The Feminine Mystique in 11th grade and have spent the last year cultivating a healthy sense of feminist outrage about body image and sexual violence and, many, many other things (seriously, ask your parents and friends how fun you are to hang out with), you haven’t yet realized how silly the terminology of “virginity loss” is. Like, Oops! My virginity fell out! Does anyone have the number for Lost and Found? Like it’s something you misplace, passively, rather than actively getting rid of. Like it’s an actual tangible thing you could get rid of — or misplace — at all. Also, please stop telling people you’ve read The Second Sex. We both know that’s a lie.

Anyway, if pressed, you might say that you’re going to have sex for the first time tomorrow, which, again, is kind of absurd because you have had a lot of sex already. But because you think that putting a penis in a vagina is the pinnacle of human sexual experience — not entirely your fault, as 90% of the world around you seems to feel the same way — you don’t really think that any of the sex you’ve had so far counts. It will be a while before you learn about heteronormativity and realize that this definition of “sex that counts” leaves out the many women whose vaginas never have penises put in them, and the many men whose penises never come within a five mile radius of a vagina. I wish you’d figured it out sooner, for many reasons.

Regardless, at 16, you have already had quite a lot of sex, even if you wouldn’t call it that. Those BJs you gave your boyfriend? Sex. That inexpert cunnilingus he performed on you, as you laid there hoping he wouldn’t notice the stretch marks on your inner thighs and asking yourself if this was meant to feel good, because it mostly felt like he was writing the alphabet with his tongue but with the goal of trying to carve a new Rosetta Stone? Sex. Shitty sex, but sex nonetheless. It all counts. And you should have figured out that it counts, because it was nerve-wracking and thrilling and after you did all those things for the first time, you felt as if some rubicon had been crossed. It meant something to you, and to him. Because it was sex.

Yes, you say, but that was oral sex. There’s sex, right, and then there’s oral sex. To which I’d say — if I could talk to you face-to-face without breaking the space-time continuum and dooming you/me to a future in which Christina Aguilera is President and Barack Obama is a judge on The Voice — yeah girl, oral sex has the word “sex” right there in it. It totally counts.

Anyway, tomorrow you’re going to have vaginal intercourse for the first time, unless that phrase has caused your vagina to dry up for all eternity, which would be totally understandable.

Here’s how it’s going to happen. Your boyfriend of thirteen months, your first serious boyfriend, will be over at your house, and Mom will be out for the day, and then Dad will go out to the hardware store or somesuch. In retrospect, you will wonder if he knew exactly what was about to happen as he walked out the front door and got into the car. Not that it was hard to predict that in his absence, you and your boyfriend would go to your room and make out a bunch on your single bed. And then, on top of him, you’ll stop, look him in the eyes, and say, “today.” He is eighteen and has been waiting twelve months and twenty-nine days for this green light, so he will be delighted. In the moment, he’ll also be dick-shrinkingly nervous. Once he gets over that, though, and manages to get the condom on, you will “have sex” for “the first time.”

And it will hurt like a motherfucker.

It will hurt so much that you’ll wonder if he’s putting it in the wrong hole. It will hurt so much that it will feel like he’s stabbing you in the vagina. It will hurt so much that you’ll stop long before he gets close to coming. And that’s how you’re going to lose your virginity.

When you tell your friends about it, you’ll lie about how it went. You’ll tell them that you were both nervous, but that you both enjoyed it. Inwardly, you are baffled that this activity could ever feel good for a woman. The space between what you just experienced and good — let alone orgasmic — is a wide, yawning gap. “This sex thing is pretty great,” you’ll tell your two best friends, feigning both a satisfaction and a nonchalance that you do not feel.

You will try again in the coming weeks — in fact, you’ll try many times, hoping that the pain was a first time thing. You’ll tell yourself that it probably hurt the first time because your hymen was breaking, which is highly unlikely. You are an ex-gymnast, and you fell with one leg on either side of the balance beam a few too many times for that to be a plausible explanation. Still, you’ll keep trying, and at your insistence he will keep ramming his penis on in there, even as your vagina burns and screams in protest, feeling like it’s tearing with every thrust. It will hurt enough that you wouldn’t be surprised if he pulled his dick out to find it covered in blood.

So that’s what the next few weeks hold for you. And also the next few months, and the next few years. I’m writing to you from a more than a decade into the future, hon, and I wish I could tell you that the pain will be over soon. But this is just the beginning.


Dear Chloe,

You sure do cry a lot after sex. This is still true in the future — my present — but in the future, you cry for good reasons: relief, love, compassion for past versions of yourself. Right now, though, at 19, you cry from the pain, and the frustration, and the fear of disappointing the man you love, and the dread that sex is always going to hurt this much.

It’s sure as hell not getting any better, is it? You’ve slept with four men now — three of them long-term boyfriends — and it’s hurt every time. Every single time. With condoms, without condoms, with lube, without lube. It doesn’t matter how turned on you are, how badly you want them, or how badly you want it to just please, for the love of god, work. It hurts every time. When he puts it in, when he thrusts, when he pulls it out, and for a half hour afterward. Sometimes it feels like your body just won’t let him in; the muscles that should be soft and giving, that shouldn’t feel like muscles, are tight and tense. You want to give him sex. You have no give. It’s like trying to dig change out of firm and tightly packed couch cushions, getting him in, and when you push him through the tension, you’d swear he’s tearing a hole in you.

You’re getting very practiced at gritting your teeth and digging your nails into his back, urging him to come quickly not because you want for him to orgasm, but because you just want it to be over as soon as possible. It stings, it burns, it aches. And forget getting off after intercourse; the pain numbs you to the pleasure. When it’s so bad that you have to stop — when your ex-gymnast’s high pain threshold doesn’t get you through — you’re getting very good at ignoring the lingering pain as you get him off with your hands and your mouth. You love him, and he loves you, and you also fear — no, you know — that it’s your job to get him off, no matter what. And if you can’t do it with intercourse, with “home base,” with the kind of sex that really counts — well, then you better give one hell of a blow job. You are getting very good at wiping your tears and getting on your knees.

He’s doing the best he can, this boyfriend. At 19, he hasn’t had a whole lot of sex, and he’s certainly never had a partner who’s as high-maintenance as you are. It can’t be that fun for him, having a partner who cries after sex, who makes him stop halfway through, or worse, when he’s so close, because she’s in pain.

Of course, you know this. You think more about his pleasure and his needs than you do about your own, feminist principles be damned. You took Intro to Women’s and Gender Studies this year, and you know what all the theorists would say — and you also know that men like sex, and men want sex, and men will get upset if they don’t get sex. So you don’t always ask him to stop. And I wish you would, little one. I wish you understood that every time you have sex that hurts, you’re teaching your body and your brain — they’re so connected, you know this — that sex hurts. Unlearning that will take years.

And before you can unlearn that — before you can break that psychosomatic connection — you need to unlearn so many of the things you’ve learned without realizing you’ve learned them. That intercourse is better than oral sex is better than other forms of sexual pleasure. That it’s your job to get him off, no matter what. That men are so fixated on sex that they’ll walk away if they’re not getting it. That you are broken and defective if you can’t give it to them, this thing they supposedly want more than anything else on the planet. I mean, what the fuck is wrong with you? This is the most basic thing in the world; it is literally how the species survives. I know you don’t think that women are only good for sex, but they are supposed to be good for sex! Why aren’t you? Why are you so bad at being a woman? And why are you so bad at being a feminist? Don’t you know you’re supposed to put your pleasure first? Why are you acting like his pleasure trumps your pain? You’re a traitor, lying there on your back, wincing, betraying your principles with every thrust.

Sometimes, when I have good sex now here in the future — not just nice sex, but good sex, as unimaginable as that is to you right now — I think about you, and I cry for you. I cry because want better for you, and I know how long you’ll wait for it. I think about how much pain you’re in, and how confused and alone you feel, because everyone around you is talking about how good sex feels. Hell, the man on top of you is telling you how good sex feels. And you feel utterly inadequate, and no amount of apologizing to him (for stopping) or to yourself (for not stopping) will make that feeling go away. Just like the pain won’t go away just because you will it so.

I wish I could scoop you up in a hug and tell you that you don’t have to keep doing this to yourself — but again, Secretary of State Katy Perry. What you need is for someone to hold your face in their hands and tell you, over and over again until you really, truly hear it, that sex isn’t supposed to hurt, and that you need to talk to a professional. You will need this person again when you actually do go see a professional and they are totally stumped. This person, I’m afraid, doesn’t exist. In an ideal world, your boyfriend would be that person, but your boyfriend is a 19-year-old boy who really enjoys coming inside you, so… yeah no. And it won’t be the boyfriend who follows him, either. Or the one who follows him. That person is going to be you, little one. Eventually.


Dear Chloe,

Tomorrow is your first day of vagina therapy. After five years of painful sex, after half a dozen stumped NPs and OBGYNs, after one doctor who prescribed you a numbing cream to use during sex, for god’s sake, one gynecologist did you a mitzvah and recommended a physical therapy practice that specializes in “pelvic pain.”

It’s not covered by health insurance, of course. Also, you don’t have health insurance (thanks, future Obama).

At this point, though, you’re willing to fork over the money, and your parents are willing to help — especially since you told them that you’re considering opening up your relationship with your boyfriend, so that he can have sex with someone else. They were thoroughly horrified by the idea. So was he; in contradiction of every piece of popular culture you’ve ever seen, he recoiled, and explained that he doesn’t merely want to have sex, he wants to have sex with you. For which you at once feel gratitude and frustration. Thank god he wants that. But you can’t give it to him.

Not that the two of you haven’t tried. Of all the men you’ve been with, he’s by far the most patient and the most sensitive to your pain. Slowly, he’s helping you unlearn the idea that penis-in-vagina sex is the only sex that counts, that it’s the gold standard of getting off. But it’s also the only thing you can’t do, so, like the high-achieving Type A perfectionist that you are, you’re determined to do it.

So you’re going to physical therapy. At your first session tomorrow, you’ll arrive at the small office on Madison Avenue and sit down for a consultation — just a chat, no treatment yet. You’re skeptical that physical therapy could work on pain that doesn’t feel at all muscular, and before you hand over your money, you want to know that these people can actually help you. One of the therapists will sit you down in a dimly lit room. The whole place sounds and smells like a spa: calming music drifting out of the speakers, essential oils in the air. It looks a lot like a spa, too, with the crystals and the warm coloured walls. But for the crunchy annual pelvic exam paper on the massage table, you could be there for acupuncture or a facial.

The therapist, Rachel, will ask you to tell her about your pain. What does it feel like? When did it start? How often does it happen? How does it make you feel? How does your partner respond?

And you will lose your shit. The frustration and disappointment — in sex, in your body, in your partners, in yourself — will pour out of you. You’ll tell this complete stranger things you’ve never told your friends, or your partners, things you’ve never even admitted to yourself. That you resent your partners for feeling such pleasure at what feels like your expense, and that it breaks your heart that, when push comes to shove, their orgasm trumps your excruciating pain. That they say, “it’s ok if you want to stop,” but you don’t believe they really mean it. And you love them — after all, you wouldn’t let just anyone hurt you like that — but you hate them a little, too, and you feel that hate while they’re inside you.

Rachel will sit across from you and take notes and nod and ask more questions, and after thirty minutes of this, as you dab pointlessly at your nose with a soggy tissue in disbelief — this is a physical therapy clinic, not a therapy therapy clinic — she’ll say, “We can help you.”

And then you’ll lose your shit all over again, this time out of relief. No one has ever said that to you before about this particular problem. Half a dozen health care professionals have made flummoxed faces and shaken their heads. But Rachel, this tiny woman with curly hair and rising inflection? At the end of all her sentences? She says she can help you. And when she says it, it’s not a question. It’s a statement.

And so, vagina therapy begins. In the first session, Rachel will explain that even though the pain is a burning, stinging kind, it’s probably muscular in origin; your pelvic muscles tense up whenever anything penis-shaped comes near them, and with good reason. When you insist on putting penis-shaped things inside you anyway, the body reacts as a good body should, with pain, its way of telling you to stop. Your body is just trying to take care of you.

You’ve had a lot of physical therapy in your life — for your back and your knees and your wrists — but you’ve never had PT like this. Rachel puts her fingers inside you and presses on your vaginal wall, trying to get your muscles to release. They’re so stressed out now that they’re tight all the time. You are literally uptight (here in the future, you are only figuratively uptight). She can venture a diagnosis — vulvodynia, vaginismus — but chronic pain conditions, which mostly affect women, aren’t that well understood. What a goddamn surprise, you’ll snark as you lie on the noisy paper with your legs open, that a condition that largely affects women, and adversely affects their sexual pleasure, should be starved for research funding. What a stunning turn of events. Rachel will agree with you, nodding as she stands there with her latex-gloved fingers in your vagina.

Over the course of your sessions, she’ll get you to stretch out all the muscles around your pelvis — in your butt, and your hips, and your thighs — and give you a dilator, a smooth white plastic phallus to practice inserting and holding in your vagina, to teach your muscles to stop freaking out. When they do, she’ll give you a bigger dilator; the first one has the girth of a pen, and you’re working up to one with the circumference of your partner’s penis. She’ll tell you to stop crossing your legs when you sit down, which will tighten one side up more than the other. She’ll suggest you switch to a hypoallergenic laundry detergent and cotton panties, and that you cut back on caffeine so you urinate less often and irritate your vulva less. When a condition is poorly understood, the treatment is holistic — which is code for “try everything and see what works.”

And some things will. Not unless you do, though, unless you do the stretches and the homework and above all, stop having sex that hurts. Therapy isn’t a miracle pill or a magic spell. This wound took years to inflict, little one. It’s going to take years to heal.


Dear Chloe,

Tomorrow you’re going to come during sex for the first time.

It has been over a decade since that sweaty, nervous, summer day on your single bed in your childhood home in Sydney. And it’s been over five years since you started writing publicly about your pelvic pain condition. You parents weren’t thrilled, just like they won’t be thrilled to read these very words — and who can blame them? It’s all awfully intimate. Still, you’ve stood on a stage on a college campus and talked to undergrads about how feminism can improve their sex lives — a sneaky way to talk to them about consent and communication in relationships — and you’ve told them about how grateful you are for the feminists who declared that sex shouldn’t hurt for women and that treatment for these conditions should exist. Your voice shook the first time you gave that speech, and afterward, you got to hug the female students who came up to you in tears and said, “I thought I was the only one.” When you wrote about it, friends you’d known for years emailed you to tell you that they’d been suffering in silence, too, and had now finally decided to seek treatment. That you were able to give them what it took you so long to find — reassurance that they weren’t broken or defective, and the names of people who could help them — made it worth defying your parents for one of the first times in your life.

You don’t write about your sex life all that often now. You do write a lot about rape and sexual assault, and about consent. In the last few years, the national conversation about sexual violence — in the military, on college campuses, around sports teams — has broadened and deepened. One happy result is that the idea of enthusiastic consent, long a dearly-held notion in feminist circles, has had a national hearing.

Enthusiastic consent, the idea that nothing except hell yes is a green light for sexual activity. Less no means no and more yes means yes. The framework of enthusiastic consent emphasizes that sex is only fully consensual when all parties come to the sexual table (or bed, if you’re vanilla like that) fully committed to making sure their partner is having a great time and really wants to be there during every moment of the sexual interaction. And it emphasizes that if you’re ever not having a great time and don’t really want to be there, you’re allowed to stop. It’s that simple. There are no grey areas, no blurred lines. Consent is sexy, and it’s straightforward.

When you write about sexual violence, and about consent, you often specify that you’re not a survivor of rape or sexual assault. Which is true. But you’ve had a lot of sex that felt like violence.

Sex that hurt. You weren’t having a great time. You didn’t want to be there during every moment. You were gritting your teeth and praying it would be over soon. And yet, as far as your partners could tell, you were enthusiastically consenting. You hid your pain from them, passing it off with moans and heavy breathing. You insisted they keep going, even when you were in pain. On some occasions when they knew you were in pain, you told them not to stop — and they didn’t. You consented. This wound was, in many ways, self-inflicted. You understand why activists insist that consent is simple — the mythology of the mixed message, of the woman who says no but means yes, is so powerful and so pernicious. And yet, you can’t agree with them. There is nothing simple about what you’ve been through, what you’ve put yourself through, what’s been done to you. There’s nothing straightforward about any of it.

Consent is complicated. Desire — to be close to someone, to hold on to them, to please them, to fuck, to come, to be normal — is so complicated. Your condition is complicated. Your treatment is, too. None of it is simple. None of it is easy. The promise of sex, before you lost your virginity, before you lost a decade of your life hurting yourself and letting the people you love hurt you, was simple: sex feels good. The promise was a lie.

But these days, you do find yourself enthusiastically consenting more and more. Things are getting better, finally. You stop when it hurts, and it doesn’t hurt every time. Sometimes it’s pain free, which is nice, and sometimes it’s actually good. Tomorrow it’s going to feel better than that.

Tomorrow’s going to be a great day, hon. An unexpected landmark, and yet another reason to cry after sex, this time from disbelief and from gratitude — and from the staggering realization of how damn much you love the man you’re with. From happiness that it happened with him, and not with anyone else on the planet.

I can tell you that it’s worth waiting for, little one. And I wish you hadn’t waited so long.