The Winner, page 12
He’d said it as a joke, but as they fooled around on his bed for a while, he wondered if it was good that she’d issued this early restriction. It felt natural to be with someone his age again. And someone who wasn’t paying him for the pleasure.
“Your bed smells like vanilla,” she said.
“I sprayed an air freshener before,” he told her.
Emily’s own mother had been on top of these very sheets twenty-four hours earlier. His college teammates would think this was the coolest thing ever, to get a hot mom and her daughter into his bed on successive nights. But what he was doing was sick, certainly unfair to Emily, even to Catherine, and if it had begun as a forgivable error, now he was willfully digging himself a deeper hole.
“Promise me you won’t look at me when we wake up in the morning and say, ‘Hey, you,’” she said at one point after Conor kissed her.
“You don’t have to deflect everything with a joke, you know,” he told her.
“Look, Conor,” she said after a moment. “You seem like a nice guy, and despite being grossly good-looking, you’re somehow not a humorless idiot. But you don’t want to be with someone like me. You’re a normal and successful member of society, and I’m kind of fucked-up inside.”
Conor had been shot down by girls before, mostly ones with boyfriends, but he’d never been spurned quite like this.
“I’ll be the judge of what I want,” he said. “And you don’t seem fucked-up to me.”
CONOR WOKE IN THE MIDDLE OF THE NIGHT FROM A VIOLENT THUNDERCLAP. Still half-clothed, Emily was sitting up in bed, resting on her bent knees in the wan moonlight coming through the window as rain pattered outside.
“Hey, you,” he said. She didn’t react. “Just kidding,” he added. When she still didn’t acknowledge him, he asked if something was wrong.
“I spent three months in a psychiatric hospital my senior year at Bard,” she said.
He couldn’t tell if this, too, was one of her jokes testing out his gullibility.
“Did you . . . why’d you go?” he asked when it became clear she was serious.
In an even-keeled voice, without dwelling on the details, she told him that she’d been diagnosed with “an inability to function,” or what was more commonly known as a nervous breakdown. She was involuntarily committed to a “luxury depression-treatment center” in Connecticut (she couldn’t hide her plain scorn for the term), where experimentation with different cocktails of drugs, plus half a dozen electroconvulsive therapy sessions, eventually restored her desire to get out of bed.
She’d graduated from college a semester late because of the time she’d missed, had worked for the woman on the Upper East Side for just two months before she was fired, and after a few weeks of lockdown, with no structure, she’d started feeling depressed again. Not knowing what else to do, she’d checked herself back into the treatment center. She didn’t tell her mother about this stint, just paid for her treatment herself out of her trust. When she returned to Brooklyn in June, she was afraid she’d relapse without any structure or seeing anyone regularly; after her first time in the center, everyone at school had treated her differently, and she’d kept just one close friend, who now lived in Boston. She’d decided to come up to Cutters, where, at least, she’d be around people she’d known her whole life.
“So,” she said, “do I still not seem fucked-up to you?”
She did, now, in ways with which he was unfamiliar. But whereas Georgia’s middle-of-the-night confession had turned him off, Emily’s drew him in. Even the electroshock treatment carried a certain mystique.
“Even if you are,” he said, “something about you makes me want to take care of you.”
He kissed her, running his tongue over the ridges of her perfect teeth as the rain thrummed and the western wind carried the cleansing scent of the ocean into his cabin.
He registered that he felt something momentous again, something he hadn’t felt in all his time together with Ally, something normal people probably experienced all the time: that, despite the greater safety of keeping it shut tight, one of you had opened your door a crack, and you and the other person were sharing something no one else in the world was sharing right now.
“You’re not an asshole who plays mind games, right?” Emily asked. “You don’t just say what you think girls want to hear?”
“No,” he said.
She looked out the window into the wet, black night. Then she turned back.
“Because that was pretty good, what you said,” she told him.
Chapter 10
After she left while he was sleeping, he didn’t hear from Emily all the next day. Maybe she was waiting for him to reach out to her first, after she’d opened up to him. He would have normally done so, but Catherine was coming over that night, and he now felt even more conflicted about what he was doing.
The honorable thing was to end his arrangement with Catherine. If it happened now, before he progressed further with Emily and before any harm was done, he could still feel all right about everything. She couldn’t be that upset by it; he was well within his rights to quit what was essentially a job, and she’d expressed no interest in him beyond his body. No one would be hurt.
When Catherine arrived, though, opening up a bathrobe to reveal lacy black lingerie with a garter belt, he caved. No harm in one final romp. They lunged at each other with more than their usual ferocity, as if Catherine, too, knew this was their last hurrah, with fingers slipping into various openings, until she procured, from a pocket in her robe, a bottle of personal lubricant. “I don’t think you need it,” Conor said.
“Not there,” Catherine said. “Here.” She got on her knees, reached behind herself, and applied a generous dollop. “Have you done this before?”
He nodded. Ally had emphatically refused, though he’d done it a handful of times with other girls. It was overrated, in his opinion, but if she wanted to try it, especially on their parting visit, he wasn’t going to say no.
“I haven’t,” she told him. “Go slowly.”
With plenty of lubrication, he coaxed himself inside, thrusting carefully, wondering why she hadn’t pursued this in the past if it was something she was interested in, then refocusing on the task at hand when that line of thinking brought him to Emily’s father and then Emily. Each of her moans began building on the last until, eventually, Catherine surrendered to an orgasm so convulsive that Conor, amid his own explosive unbottling, was unsure how much was pleasure and how much pain.
She’d been right that time she whispered into his ear, saying he’d wanted to do this. He’d never had a sexual escapade more intoxicating than to be the first man to plant his flag in the landscape of Catherine Havemeyer, beautiful insurance and shipping heiress worth tens of millions of dollars.
Conor had never cheated on Ally and had no experience with this particular set of emotions. He felt like confessing to Emily; he felt like confessing to Catherine; he knew that he’d do neither. This was his punishment, the anchor of guilt he’d have to tow around, even if he were never exposed.
The other thing he knew instantly was that he couldn’t give this up; it was too good. It was the sort of sex that people assumed someone who looked like him was having all the time—the sort of life they assumed he was leading. But he’d waited twenty-five years for this without even knowing it was out there, at the very end of Cutters Neck Road.
He’d put a stop to things with Emily, then, if her daylong silence wasn’t an indication that it was already over. Whatever he’d felt for her the previous night must have been the romantic atmosphere, the rainfall, the dramatic story of her breakdown. It wasn’t real. It couldn’t have been—not like this.
When Catherine left, Conor disabled airplane mode on his phone, which he’d activated beforehand, to send Emily his deferred breakup text. But there were already three messages waiting from her. The first read, simply, “Hey, you,” in scare quotes. The second apologized for interrupting him if he was working. The last was a GIF of Glenn Close from Fatal Attraction with the captioned threat, I’m not gonna be ignored, Dan.
He’d been lying to himself. What he felt for Emily was genuine.
When you finally find the girl you want to marry, don’t blow it—they don’t come around often, Richard had advised him. Another Emily might not come around in his life.
But neither would another Catherine.
The hazy outlines of what he was considering were impossibly foolhardy, not to mention impossible to pull off. It was bound to combust spectacularly. And he wasn’t the kind of guy who could do it, as a matter of conscience, to either woman.
Except he’d already been doing it the last couple of nights.
If they ever did find out, they could handle it, even Emily. They had more money than anyone could ever want—that cushioned nearly all of life’s blows. And, he was now starting to think, there was a way to arrange it so that they wouldn’t find out.
He could really do this.
I was studying, just saw these, he wrote. Want to get together tomorrow?
He deposited Catherine’s check on his phone and, once he received the email notifying him of its receipt, ripped it into pieces and buried them in the trash under paper towels and coffee grounds, where Emily, who confirmed that tomorrow worked for her, would never see them.
III
Chapter 11
July’s blinding glare slanted into the coppery haze of August. The days slumbered from the heat that had accumulated from all the summer’s blazing afternoons like layers of dust in an untended house; the ocean warmed to a bath-like temperature; the crickets trilled in a shimmery chorus each lengthening night. It was a glorious spit of land, worthy of each extravagant dollar in the tax assessment, and it would have easily been the best summer of Conor’s life were he simply giving the occasional tennis lesson, preparing for the bar, and either enjoying his burgeoning relationship with Emily or having enormously pleasurable and remunerative sex every few nights with Catherine.
Instead, over the next several weeks, he had to negotiate between the two women with vigilance and skulduggery. He soon found that his cautious temperament transferred well from tennis to infidelity. His trysts with Catherine were only at his place; when he went to Emily’s, he arrived on foot after dark (the entrance was, as she said, not visible from the big house). As an antivirus measure, but also a convenient pretext for them not to talk, Emily and her mother communicated mostly by text, infrequently by phone, seldom in person outdoors, and never indoors together. This made sleeping at Emily’s cottage safe, as he didn’t have to worry about Catherine’s barging in (though, if she ever did, he was prepared to run into a closet). Emily, in turn, was very respectful of his need to study—and to hide their relationship from John Price—and never visited his cabin unannounced. Even though she didn’t come over much, he was nonetheless careful to spray down his cabin and bed with Febreze to mask her mother’s perfume each time (he also purchased a vanilla-scented air freshener spray as a decoy). Whenever Catherine demanded a “lesson” on a night he had plans to see Emily—which became, in time, every night—he canceled with the latter, begging off with deficits of work and sleep. He changed their names in his phone, which he set to airplane mode before seeing both, and deleted texts from them immediately on receipt.
Because he was so conscientious and clandestine, because he never took any undue chances or committed a single unforced error, and because there was a pandemic that disrupted normal social patterns, it worked flawlessly.
HE BARELY THOUGHT ABOUT COVID ANYMORE ASIDE FROM WHEN HE talked to his mother. He supposed this was what normal life was like for people this rich: so removed from the ravages of the world that to be concerned by them would be like fretting over natural disasters on Mars.
It was pure bliss on the neck, surrounded by endless ocean in endless summer. Kids biked and scootered unsupervised without helmets, perfectly groomed dogs roamed off leash. Before the dinner hour, residents sat on their porches with wine and cheese brought out by their personal (masked) cooks. A community vegetable garden yielded cherry tomatoes that burst in your mouth as sweet as candy. Saturday mornings there was a boat race, the winner of which was announced in the neckwide email disclosing the new gate code that Conor now received with a sense of pride (and relief, as he imagined Charlie rolling up in his Buick to commit more crimes and being denied entrance). There were magical spots everywhere he turned: untouched fields where deer romped in rainbow arcs; winding paths through the woods, one of which led to a tiny cabin built right into a hillside; a salt marsh on the beach filled with crabs; and a glade of purple clover near John’s house he tried to visit each evening, where the sunset bronzed the stone wall that set it off from the road and shot pole vaults of light through the clustered trees.
Being on Cutters brought to mind something a professor had said during his freshman-year sociology lecture that he remembered every time he went to the airport. The airline industry was a microcosm of American society, with each stratum marked by a corresponding level of visibility: there were the working-class masses, many of whom the passengers never saw, who slung food in the air and on the ground, serviced the planes, and so on; the sizable middle class, who sat very noticeably in coach and played a pacifying role by giving the workers the meager dream of airborne travel to aspire to; the more exclusive sliver of the upper class—subdivided between the amenities of business and the opulence of first—who were hidden mostly out of sight behind a curtain as they dined on their restaurant-quality meals; and finally the minuscule population of the .01 percent flying private out of their own airports and thus, for very different reasons, more unseen by the rest of the ecosystem than the most subterranean of baggage handlers. Air travel, the professor told them, catered to the upper class and even more so this last microclass, because that was where maximal profits lay. The rest of us were losers whose taxes subsidized the flights of the ultrarich, either laboring away to prop up the industry or reduced to begging for an entire can of soda and a second package of cookies from our cramped seats, literally unable to see how much better the people on top of the pyramid had it.
Each time Conor biked around the gate with his cargo of groceries and was greeted by a current of uncontaminated ocean air and rabbits darting across the road, he still couldn’t quite believe he lived there, even temporarily: the real estate equivalent of a private jet, the kind of place that would never be glimpsed by most Americans—by, that is, the losers.
Although, of course, he had a claim only to a guesthouse and was therefore a quasiloser himself. Everyone else was to the manner—and manor—born. Someone in their deep past, as Charlie had probably accurately speculated, had committed a crime to enable their descendants to live like this; not a violent crime, likely not anything technically illegal, but cannily gaming the system so they would profit at others’ expense. When you got down to it, the crime of capitalism. And their offspring now feasted in perpetuity off the capital gains.
He wondered what he’d be doing now if he’d remained with Ally. She’d landed in Manhattan after graduation, working in marketing for an ecoconscious fashion something-or-other, and had likely fled the plague for her parents’ place in Albany, where he would have had to accompany her. He’d always liked his visits to their four-bedroom house, with pictures of Ally and her brother and sister lining the wall by the stairs, a small, fenced backyard where her dad would grill in the summer, a finished basement with a foosball table. They were the sort of family that went to the movies on Christmas. Very American, as Catherine would put it. Or, more bitingly, middle class.
He’d never had a problem with it in college—if anything, he’d thought it was something to aim for, even the overly cheerful extended family. But he couldn’t go back to that kind of life. Not after this.
And the only permanent way into an un-American—or, in another sense, quintessentially American—place like Cutters Neck, besides being born into it, was through marriage.
IF CONOR HAD WORRIED THAT MARRYING ALLY WOULD BE RESIGNING himself to a lifetime of tepid feelings, he had no such concerns with Emily. She was funnier, worldlier, smarter than he was. Respectably unimpressed by male beauty. She would challenge him, educate him, entertain him. She did a routine that made him laugh hard every time: wearing socks on the linoleum floor of his kitchen, she’d simulate her mental state of paralyzing uncertainty off her psychiatric medications by running in one direction, sliding, then cartoonishly reversing course and sliding again.
Emily’s political conscience didn’t manifest itself through grandiloquent, self-serving speeches or hectoring social media posts, like his more outspoken law school classmates. When reading the news, she’d become incensed by the cruelty, stupidity, and injustice of the world, though she had little patience for liberal bromides. “These people are fucking idiots,” she said one night, looking up from an article about corporate diversity training in the wake of George Floyd. “Teaching their employees not to be racist, or sexist, or whatever, it’s all a bullshit Band-Aid. They know the real problem is money, and the only way to solve it is changing who gets the money. But they don’t want to give up any of their own money, so nothing will really change.” Even if Conor didn’t share the fervor of her convictions—he didn’t have the luxuries of time and resources to concern himself as she did with the suffering of others—he admired her for it and for how she walked the walk with her frequently opened pocketbook.
She told him more about her family. Her father, the “great-great-whatever-grandson” of the second governor of the Plymouth Colony, had remarried a hostess from an Upper East Side cigar lounge, producing two young half brothers Emily barely knew. After her first stay at the treatment center, Emily had decided he was a “toxic presence” in her life (“I know how overused that word is, but it applies in this case”) and stopped talking to him.
Conor was careful not to display too vested an interest in Catherine, though at times he couldn’t resist asking questions; Emily was his only outside perspective. She had had some boyfriends when Emily was younger but nothing that ever took, partly because “she was always paranoid guys were trying to marry her for her money.” She’d trained to be a painter when she was young but had given it up when Emily was three or four. Hiding his surprise over Catherine’s artistic past, Conor asked why she’d stopped.
