Lost: Orgasm. Reward if Found.

A yearlong quest to come after a bad breakup led me to BDSM dungeons, pegging parties, and eventually a pool of my own sweat, but I was no closer to the little death I so desired.

• • •

I lost my orgasm in 2007. On the spectrum of things I’ve misplaced, the event fell somewhere between losing my religion and my damn mind.
 
I had just broken up with my first girlfriend, Amanda. Before we dated I really, really did not want to be queer. In fact, even after we’d slept together, I sent her a bulleted list of “reasons” why I was not THAT WAY, including this gem of logic: “Lesbian sex feels shallow!” But it didn’t take me long to get over my prejudices. Although Amanda and I were both fairly new to sleeping with women, we were eager to try every sexual act we could conceive of, and even a few we could not. One disastrous attempt involved a pink rubber dildo-thong-vibrator combo with a blue tip. It was like a one-man band…or, a very thoughtful rhinoceros. Despite this and other amusing failures, I was finally having the kind of sex I’d always imagined—exuberant, budding, joyful, and full of orgasms. I’d found my North Star. And so, when our relationship began to fade after three years, my sexual compass went with it. Who was I? What did I want? Who did I want?
 
The day after the whole thing finally imploded, I found myself wandering a cemetery near my house in Chicago. My eyes kept coming to rest on graves that had my first name etched into the stone. My relationship was dead. Was my sex life dead too? I was 24. A baby. A morbid baby. But sex and death have always been inextricably linked. The French, in their divine explicitness, liken an orgasm—and its subsequent expenditure of life force—to “a little death,” or la petite mort. In my grief over the breakup, the best way I knew to reaffirm my aliveness was through experiencing these little deaths, so I set about trying to do just that.

Pam was first. She had small hands and a boy’s ass and was also coming off a failed relationship. Her ex-girlfriend couldn’t orgasm, so the first time we had sex and I didn’t come, I lied and said I did. I wanted to be everything her ex-girlfriend was not. I wanted to be what she wanted me to be—someone else.
 
I kept lying. Fake it till you make it, I thought, and so I did, over several months during which Pam and I had sex in my truck, on too-small couches, and in a YWCA. But then her ex decided she wanted her back, and our tryst, like my ability to orgasm, ceased to exist.  
 
Miles was next. He was a carpenter with a big laugh and the kind of body that would not be out of place on the cover of a paperback romance. We had sex once a week but knew nothing about each other. After two months, we were surprised to discover we were both vegetarians. We had never eaten a meal together.

It was around this time that I started to panic. From the age of 12 on, I could come easily and often from just about everything—hands, tongues, toys, a well-placed stuffed animal, even, occasionally from straight ol’ penis-in-vagina sex—but suddenly my old standbys were no longer working. I was standing on a cliff with neither the smarts to back away nor the wherewithal to jump. I was stuck, and decided something drastic needed to happen to pull me out of this crippling stasis. 

I started saying yes to everything: the domme who invited me to watch her sexually humiliate a submissive, middle-aged man, for which I was paid $50 and treated to a sushi dinner; the undergraduate student who enjoyed exhibitionism; the philosopher who taught me that, yes, Heidegger can be used as foreplay; and the man who desperately wanted me to peg him (and who did, indeed, get pegged).
 
Eventually there was Shana. Technically speaking, I was polyamorous for the entirety of this post-breakup dating free-for-all, but it was Shana who put a name to it and more formally introduced me to that world. Shana had fallen in love with a Canadian bus driver right before we met. She told me this on our first date, and I was both relieved and insanely jealous. I loved her almost instantly, but would not let myself be loved by her. I couldn’t be open in this way. It felt “like giving yourself to be flayed and knowing that at any moment the other person may just walk off with your skin,” to quote Susan Sontag. But, I could, it turns out, get flogged by near-strangers, and that was fine!
 
Shana took me to BDSM clubs and play parties. I received my first caning and was introduced to something called a “prison strap,” a leather paddle thick as a tongue and two feet long. No matter how much it hurt, I prided myself on what I could endure. The bruises on my body became a river of names I did not bother to learn. I told myself I was healed. I was sexy. I was alive! If I stopped to consider otherwise, even for a moment, the facade I had built would topple like a cake baked 12 stories high.
 
My sexual forays became more frequent, more reckless, more more. And still I could not come. I kept waiting for the sex to be a salve. I kept waiting to feel something other than loss. Five months without an orgasm became seven and then nine. Increasingly hopeless one night, I began to masturbate furiously, upping the speed and intensity on my vibrator until my entire lower body went numb and sweat pooled on my lower back.

A month later I met Jennifer, a pastry chef whose smile was like an embrace—one glimpse and I consented to the world. Jennifer listened to my stories with gentleness and concern. Our connection was swift and all-consuming. The first time we had sex (on our first date), she exclaimed, while on top of me, “Way to go, OkCupid!” I didn’t come this time, nor the one that followed, but over the course of about 10 days she dispelled the ugly myth I had been telling myself the past year: that my sexual openness was an adequate substitute for emotional honesty with others, or even myself. I was filling the spaces between my ribs with stories I wanted to read and beautiful untruths, and, frankly, a lot of unnecessary laundry.
 
The tight fist of my impermeability unfurled like a leaf bud under Jennifer’s steady hand. It was with her that I realized my attempt to outrun my grief only caused me to cave in on myself, stripping away those fundamental components of good sex: joy and trust. Vulnerability wasn’t a street fight—it was a necessity.

One night, two weeks into our courtship, we walked home from a date as snow fell in big fat flakes. In the shower, she washed my hair and rubbed my neck and shoulders with sesame oil. She touched the residual bruises on my thighs as though they were places on a map she could never visit.
 
On the bed, she took my face in both of her hands, and it was as though I was being held not by a person but by a silent, shared hunger. Suddenly I was softer than I’d ever been in my life. I felt uncomfortably exposed, the seams of my resolve fraying, until I realized my strength wasn’t gone—it was just in Jennifer’s hands. Likewise, I watched her tenacity curl like dried leaves, wilting in the heat of the radiator quietly humming beside us. She pressed her lips to my neck, erasing the night and the strains of the outside world, a cooing emptiness overtaking me.
 
Grasping lightly at the shirt bunching at Jennifer’s waist, I pulled her closer, steadying us both. The coming together of our hips sent a pulse straight down into my center. Everything became momentous—the cloudless night, the groan of the floorboards, my cells that seemed to reach for her, to ache for her aliveness, the tight, fevered grooming of skin on skin.
 
We stayed locked into each other for several beats. I held on tight, feet clutching, lips clutching as she sank into me, everything mottled, our faces so close, breathing in hair and salt and sweat. In the pulsing tide of her hands upon me, I let myself be baptized and washed away. The bomb between my legs filled us both, brimming and aching from the reach, all of it swirling inside, complex as a thousand-year-old stone. Everything fell away under the strange, ecstatic moon; our bodies distilled into a thousand points of energy, then faded soft as an echo. We began and ended only in each other’s sighs.

I died countless times that year, but when I finally came that night, in hot unceremony, it felt much more like a beginning.

Editor’s note: Some names and details have been changed to protect privacy.

ANNA PULLEY  is a writer whose heart blooms in its cage. 

PAUL WINDLE is a Los Angeles–based artist who works across a variety of media including animation, art direction, and illustration.