The Best Literary Masturbation Scenes of All Time

Rebecca Rukeyser, author of the sleaziest book of the year, recommends stories dripping with lust and existential angst

Natasha Lyonne in The Slums of Beverly Hills

Masturbation scenes run contrary to the standard rules of writing good fiction. There’s not a whole lot happening, plot-wise. The character involved is hardly moving, their thoughts are both incoherent and numbingly predictable. Nuance is abandoned, Gods rise from a variety of machines, clichés proliferate. What a shocker: the pool boy is sweaty and needs to take of his shirt.

But this is exactly what makes masturbation scenes so interesting: they’re evidence that desire exerts enough pressure to not only immobilize a character, but also take the narrative within their head and distort it, chop it, repeat. The pool boy, already shirtless, needs a glass of lemonade. No, now he’s clothed but oops! the lemonade spilled on his shirt!

At first glance, a masturbation scene is uncluttered: a monologue on a bare stage. A character negotiates with what they want, and how they want it. But there are always other desires caught up in the sexual and masturbation becomes an act of boredom, loneliness, depression, love, excitement, fury, sorrow, celebration, grief, insomnia—sometimes all at once. 

These scenes are ambivalent, offering evidence of our self-sufficiency and searing need for other people, our capacity for both empathy and objectification. Both the character masturbating and the reader reading are made aware—often uncomfortably—of both the locked box of their own minds and the fact that they’re participating in something universal. 

My interest in both ambivalence and desire-fueled narrative distortion is one reason I wrote a novel, The Seaplane on Final Approach, preoccupied with masturbatory fantasy. Obviously, I’m not the only one: here are ten novels with scenes that portray masturbation exceptionally well.

Lightning Rods by Helen DeWitt

“The problem with this fantasy was that it was hard to get the wall right.”

Joe is a sad-sack stuck in two repeating loops. One: he tries to sell vacuum cleaners, gets invited in for dessert, returns to his rented trailer in a sugar-bloated fugue state. Two: he masturbates imaging his ideal, deeply specific scenario.

The problem is Joe keeps getting bogged down in the details of his fantasy, constructing backstories, imagining complex setpieces. But his tendency to embellish marks him for success. Joe markets his fantasy—a kind of deluxe glory hole—as the ideal solution to workplace sexual harassment in this deeply strange, discomfiting, hilarious novel. 

Milk Fed by Melissa Broder

“Feed me, Mommy! So that I may live!”

Rachel, who struggles with disordered eating, has, on the advice of her therapist, started a 90-day “detox” from her cruel, fat-shaming mother. On day four of the detox she starts fantasizing about her boss Ana.

Rachel imagines lying bed with menstrual cramps, “Mommy Ana” soothing her by rubbing her tummy. Things progress, and Mommy Ana takes complete control. She assures Rachel that she’s innocent, and things build into a fully imagined (and very funny) scene of submission, care-giving, and filthiness.

Private Citizens by Tony Tulathimutte

“Better than having sex, you could make sex.”

Will’s girlfriend Vanya is away and he takes the opportunity to revisit his vast, lovingly collated porn collection. Will is no stranger to creatively straining the limits of porn consumption: he’s already learned to create jury-rigged 3D porn by watching two clips side-by-side with his eyes crossed. When he realizes he wants to see a representation of his and Vanya’s sex life onscreen, he turns to editing. 

In this manic, virtuosic scene, Will spends a week in a vortex of image stabilizing, compositing, carpal tunnel flares and increasingly strained orgasms. And then he’s left emptied of lust, with no friendly buffer between himself and reality.

1982, Janine by Alisdair Gray

“Most pornography fails by not being dramatic enough. There are too few characters.”

Jock McLeish, a mid-aged alcoholic businessman, is in a non-descript hotel room in a non-descript Scottish town. He’s constructed a sort of ongoing pornographic mega-novel in his head, filled with a huge cast of hotties, including Janine, who’s based on a childhood memory of Jane Russell. 

But the evening of self-love becomes a dark night of the soul, as Jock starts to realize that his fantasy babes are all, in one way or another, figures from his past. 1982, Janine unspools, from drawn-out masturbation scene to existential reckoning to regretful-yet-hopeful quietude. 

Sabbath’s Theater by Philip Roth

“He had only to drop to his knees to be as invisible from the road as any of those buried around him, and often he was on his knees already.”

This list could have contained Portnoy’s Complaint, because Portnoy’s Complaint. But in the attempt to showcase the range of masturbation scenes, I wanted to include something truly abject. And this nails it. 

Sabbath’s Theater is preoccupied with two abysses: lust and death. They’re portrayed as dual sources of murky oblivion and are treated with a lack of reverence so complete it somehow becomes reverent again—like when Mickey Sabbath, grief-stricken, ceaselessly repellent but with the same charisma as a black hole, masturbates on his dead mistress’ grave. 

The Color Purple by Alice Walker

“But when I hear them together all I can do is pull the quilt over my head…”

It’s a scene that starts full of charged optimism between two women who haven’t yet admitted that they want each other. Celie has never had an orgasm and always viewed sex with her husband as an ordeal to withstand. She reveals this to her more-than-just-friend Shug, who’s horrified and sits Celie down for a frank discussion about the clitoris.  

But then Celie gives Shug permission to sleep with her husband, and Shug takes her up on it. Later that night, Celie, listening to Shug and her husband having sex, masturbates and cries simultaneously, overwhelmed with a mixture of jealousy and yearning. 

English, August by Upamanyu Chatterjee

“From today, no masturbation. Test your will, you bastard.”

This is what Agastya Sen, nicknames “August” and “English,” writes in his diary after he gets to his swanky government post in rural Madna. But his will is broken almost immediately. Blame a combination of Madna’s infamous heat—the humidity is so powerful lizards peel off walls and land to the floor with a splat—Agastya’s daily habit of smoking heroic amount of weed, and the boredom of provincial bureaucratic life. 

English, August is filed under “coming-of-age” and “slacker” novel. And it’s both: it charts Agastya’s self-discovery, but also sees him spend a bunch of time lying around stoned and listening to music, naked except for a layer of sweat. 

Wetlands by Charlotte Roche

“I have to stop exploring the inside of my body. I need both hands now.”

When Roche talked about her ideal response to this novel, she imagined a reader alternating between arousal and complete revulsion. This was part of her project to make this book a realistic, honest book about the body, warts—or festering pustules—and all. And it succeeds. There are passages that make Ottessa Moshfegh seem like Barbara Pym. 

Wetlands’ protagonist, Helen, is in the hospital with an anal fissure but that doesn’t stop her from masturbating. A lot. And she details the minutiae (textures! movements! viscosity!) with both gleeful investigative curiosity and the dispassionate remove of an anatomist.  

Confessions of a Mask by Yukio Mishima, translated by Meredith Weatherby 

“I felt a secret, radiant something rise swift-footed to the attack from inside me.”

Kochan is flipping through art books and finds a reproduction of Guido Reni’s “St. Sebastian,” which stops him in his tracks. Reni’s Sebastian is naked except for a pale loincloth, his hands are tied above his head, and, even though he’s pierced through with arrows, he’s unbloodied and looks tranquil. And hot. 

It’s this image that spurs Kochan’s sexual awakening, and he has his first experience with what he refers to as his “bad habit.” This is scene is textbook Mishima, in that it’s weird, divisive as hell, the language is lush, and the erotic is blended with violence.

The Pervert by Michelle Perez, illustrated by Remy Boydell

“You’ve seen me do this a million times. I’m calming my nerves.”

So says the unnamed protagonist of Michelle Perez’ graphic novel, which follows a trans sex worker through the dreamscape of Seattle as she encounters a rotating cast—some despicable, some kind, almost all shattered by loneliness.

In one section, we see the end of a romance. The protagonist and her girlfriend, whose relationship has become sexless, take a weekend trip to Portland. The frustrated protagonist masturbates as a way of getting to sleep and her girlfriend gets upset. A bleak, familiar scene unfolds: a relationship’s final fight where both parties are too exhausted to be passionately angry, too exhausted to be gentle with one another. 

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