The Kept Man She Could Never Buy Back

1 I was the most disciplined kept man in our circle. I never checked her phone. I never asked about her whereabouts. I never expected to meet her family. When Victoria was busy, I dissolved into the background. When she needed a companion, I appeared on time, immaculately tailored in a bespoke suit, ready to intercept drinks, smooth over awkward conversations, and ensure she never had to lift a finger. Even Victoria herself used to say, "Nate, you’re less maintenance than my entire executive board." Our arrangement had worked flawlessly for five years. That was, until she picked up a college kid who didn’t know the rules. He snooped through her phone, drove her cars, barged unannounced into her corner office, and called her at three in the morning, drunk, demanding to be picked up. Instead of getting angry, Victoria just smiled and called him "youthful." The first time he attended one of our private industry dinners, he took the seat directly to Victoria’s right. Someone discreetly pointed out that it was my seat. He just leaned back against the chair, completely unbothered. "Victoria didn’t say I couldn't sit here." Victoria didn’t ask him to move. Later, he moved into the townhouse she had given me. He drove my car. He even cracked open the bottle of Macallan I had been saving for five years just to entertain his friends. He wrapped an arm around Victoria's waist, looking at me with a provocative smirk. "Nate's been with Victoria for so long, I'm sure he doesn't mind, right?" Of course I didn’t mind. I simply loosened my tie, unclasped the Patek Philippe watch Victoria had gifted me, and tossed it into a drawer. Then, I pulled out a pair of black obsidian cufflinks I hadn't worn in years and fastened them to my sleeves. I, Nate Hayes, knew how to play the game, which meant I knew how to walk away from it. In this world, you play the role you are assigned. A kept man can be greedy, but he can never afford to forget his place. Unfortunately, Oliver didn’t understand that. He thought Victoria breaking her rules for him meant he was special. He didn't realize the fatal truth about women like her: if she compromises her boundaries for you, it’s only a matter of time before she compromises them for someone else. ... "Mr. Hayes, the car scheduled for you tonight has been rerouted." Victoria’s assistant paused on the other end of the line. "Ms. Montgomery is already escorting Mr. Grant to the venue. You’ll need to arrange your own transportation." I stood before the floor-to-ceiling mirror, pressing the black obsidian cufflinks into place. The cold, heavy stone pressed against my wrist bone, sharp and sobering. "Understood." I didn’t ask why. Whether she picked me up or not didn't matter. Everyone in our circle knew Victoria despised the superficial pageantry of corporate galas. For the past five years, her only job was to sit at the head of the table and look unapproachable. The rest of it—the toasts, the small talk, the keeping track of favors and grudges—fell entirely on my shoulders. The moment I stepped into the banquet hall, an event coordinator hurried over, looking intensely uncomfortable. "Mr. Hayes, your seating arrangement has been adjusted." I followed her gaze. In the seat to Victoria's right, Oliver was leaning back, laughing at something she said. Pinned to his tie was a brilliant sapphire lapel pin. It was a Montgomery family heirloom, exclusively worn by the male companions of the Montgomery family at formal events. Three days ago, Victoria’s assistant had delivered it to my townhouse, instructing me to wear it tonight. Now, it was sitting on Oliver's chest. "Nate! You made it." Oliver stood up, waving me over. Half the ballroom turned to look. "This pin is gorgeous, though I'm not quite used to wearing something so flashy." He touched the sapphire with a dismissive little laugh. "Victoria said my suit was too plain and told me to just grab whatever accessory I wanted." Whatever. A symbol of status and belonging, reduced to a random trinket he’d just happened to pick up. Victoria lifted her eyes to look at me. Her gaze snagged on my empty wrist for a fraction of a second. "Why aren't you wearing the watch I gave you?" "I’ve worn it for five years. Thought I’d change it up." I smiled and took my newly assigned seat. I was placed three spots down from Victoria, right next to the foundation’s executive secretary. From her right-hand man to the staff section. A very clear demotion. Halfway through the dinner, Richard Caldwell, the developer handling the Southside Project, walked over with a glass of wine. Oliver immediately jumped up, smiling brightly. "Uncle Richard!" The smile vanished from Caldwell's face. He was thirty-eight, a tech-to-real-estate prodigy who notoriously despised having his age pointed out. Oliver didn't notice the freeze. He kept his glass raised. "I heard you yielded that plot of land to Victoria! And for twenty percent below market value, too." The table went dead silent. The acquisition was strictly confidential. The price was an absolute bottom line neither side was supposed to acknowledge publicly. Caldwell slowly lowered his glass. "The company Ms. Montgomery keeps seems to have very loose lips." Victoria’s brow furrowed, her expression darkening. I picked up my glass, stood up, and slid seamlessly into the silence with a practiced smile. "Please forgive him, Mr. Caldwell. Oliver merely overheard the foundation’s preliminary donation figures and got a bit too excited, mixing up the details." I turned my gaze to the executive secretary beside me. "Montgomery Holdings is increasing the equipment procurement budget for the Southside Children's Hospital by twenty percent, isn't that right?" The secretary froze for a second before nodding frantically. "Yes! Yes, the paperwork will be on your desk first thing tomorrow morning, Mr. Caldwell." Caldwell’s expression softened slightly. He clinked his glass against mine. "Mr. Hayes always knows exactly what to say." The crisis was averted. But Oliver looked humiliated. He sank back into his chair beside Victoria, his voice dropping into a sullen whisper. "I was just trying to help. Did Nate have to make me look like an idiot in front of everyone? Does he think I don't know anything?" I swirled the wine in my glass. He caused the disaster. I cleaned it up. Yet somehow, he was the one playing the victim. Victoria murmured something to comfort him, then looked down the table at me. Her eyes were sharp with disapproval. "Nate, it's his first time at an event like this. Was it really necessary to embarrass him?" I was suddenly reminded of three years ago. It had been my first time accompanying her to a chamber of commerce gala. I had accidentally mispronounced the surname of a partner's wife. Victoria had made me copy the entire guest list and their interpersonal relationships ten times by hand. “If you’re going to stand by my side, the most important thing is knowing the rules,” she had said. Now, a catastrophic breach of confidentiality was just "youth." Apparently, the rules depended entirely on who was breaking them. "Victoria, I was just smoothing things over for him," I said, my voice perfectly level. "Would you like me to repeat exactly what he just exposed to the room?" Her face tightened. Oliver immediately grabbed her wrist. "Victoria, let it go. Nate obviously doesn't like me. I'll just keep my distance from him from now on." He said let it go, but he ducked his head, his eyes rimmed with red. People at the neighboring tables were already staring. Victoria absolutely despised men losing their composure in public. In the past, if I even remained silent for a beat too long, she would sharply instruct me to fix my face. But this time, she gently pushed a glass of water toward Oliver, softly telling him not to overthink it. Then, she looked at me across the expanse of the table. Her tone was quiet, but it left no room for argument. "Nate. Apologize to Oliver." The entire table went completely still. Dozens of eyes pinned me down. Curious, mocking, waiting for the punchline. I swallowed the bitter acidity rising in my throat, slowly placing my wine glass back onto the table. The smile on my face remained flawless. "Victoria." It was the first time I had ever addressed her so casually in a setting like this. "You know exactly who misspoke just now." "I know." Her expression was a wall of ice. "And you know I just saved the Southside Project for you." "It's only eight million dollars," she said dismissively. "It’s Oliver's first time at a gala. You deliberately backed him into a corner in front of a room full of people. You were out of line." That short sentence felt like a shard of glass sliding between my ribs. Not excruciatingly painful, but a dull, agonizing ache. She knew everything. She knew he was wrong. She knew I was right. But she still chose him. Oliver tugged at her sleeve. "Victoria, please don't force him. Nate is so proud. He’d never apologize to someone like me." With one sentence, he hung me out to dry all over again. If I didn't apologize now, I was the bitter veteran using my five-year tenure to bully a young newcomer. The last shreds of Victoria's patience vanished. "Nate. Do not make me say it a third time." She looked at me the way she would look at a subordinate who had suddenly lost their mind and embarrassed her in public. Oliver looked down at the sapphire lapel pin on his tie, then at the empty space at Victoria's right hand. "It's all my fault. I shouldn't have worn Nate's pin, and I shouldn't have sat next to you. It made him upset. Maybe I should just give it back to him." He reached up as if to unclasp it. Victoria caught his hand, pressing it down. "I gave it to you. Keep it on." Then, her cold eyes locked onto mine. "It’s just a seat and a piece of jewelry. Do you really have to ruin the night for everyone over something so petty?" I lowered my gaze, my thumb brushing against the cold obsidian at my cuff. So that was it. The position I had meticulously guarded for five years was, in her eyes, just a trinket she could casually toss to someone else. "I'm not ruining anything," I said quietly. "In fact, I'm saving you both a lot of trouble." I picked up my wine glass and tipped it over, pouring the expensive vintage straight into the silver ice bucket beside me. "Since Oliver likes that seat so much, he can keep it. From now on, he can memorize everyone's dietary restrictions. He can intercept the drinks. He can learn which board members can't be seated next to which rivals. Let him learn." Victoria stared at me. "What are you talking about?" "Exactly what it sounds like. You think I’m too harsh on him? Fine. Consider me entirely removed from your social calendar." She let out a dry, incredulous laugh. "Nate, what kind of tantrum is this? Don't forget who pays for the townhouse you live in, the car you drive, and everything you've consumed for the last five years." Someone nearby sucked in a sharp breath. With that single sentence, she ripped away the last veneer of my dignity. I nodded slowly. "You're absolutely right, Victoria. Since you gave it all to me, we should probably do a proper accounting." I pulled out my phone and, right in front of her, dialed my assistant. "Emma. I need an itemized list of the properties, vehicles, watches, and any other assets gifted to me by Ms. Montgomery. In addition, I need a comprehensive ledger of every corporate gala I’ve attended on her behalf, every favor I've called in over the last five years, and the eight million dollars I just saved her tonight. Pull it all together." Emma hesitated. "Nate? What’s going on?" "We're cashing out." Victoria’s eyes turned glacial. "Are you determined to lose your mind tonight?" "Calculating what I'm owed is losing my mind?" I pocketed my phone and gave her a polite, hollow smile. "Victoria, the biggest mistake we ever made was blurring business with affection. Since this is a partnership, let’s play by corporate rules." I picked up my suit jacket and turned away from the table. Just before I stepped out of the banquet hall, I paused and looked back. "I expect the invoice settled by the end of the month." At nine o'clock the next morning, I didn't receive a settlement sheet. Instead, I got a notification that my black AMEX had been frozen. Right after, the doorbell rang. "Mr. Hayes, I need the keys to the Aston Martin." I walked out of the townhouse to find Victoria's driver standing at the bottom of the steps. Behind her stood two corporate aides, one holding an asset registration clipboard, refusing to meet my eyes. The driver lowered her voice, sounding apologetic. "Ms. Montgomery canceled your supplementary cards, and the vehicle is being temporarily recalled. She said when you’ve cleared your head, you can contact her directly." Victoria actually believed that without her credit cards and her cars, I would crawl back and beg for forgiveness like a disciplined dog. I dropped the AMEX and the car keys into the driver’s palm. "Is there anything else?" The driver blinked, startled. "No, just these for now." "Good. Don't lose them." She looked at me, her expression complicated. "Mr. Hayes... do you need a ride somewhere?" "No." I pulled out my phone to hail an Uber Black. Victoria could freeze the cards and take the cars. But the real estate already transferred to my name, the watches, and the hard cash she owed me for five years of labor? I wasn't backing down on a single cent. I could walk away from the feelings. But I wasn't walking away from my money. I had played the perfect companion for five years, but I wasn't running a charity. My Uber pulled up to my private event studio. Emma practically sprinted out the front doors, clutching a termination notice. "Nate, The Plaza just broke our contract. They’re refusing to give us the ballroom." In three days, my firm, Hayes Events & PR, was scheduled to host a massive international brand dinner. We had paid the deposit six months ago. "Reason?" "Montgomery Holdings booked the entire floor. They’re throwing Oliver a 'youth charity art exhibition.'" Emma handed me her tablet. "They also demanded we hand over our guest list and media contacts. They said since you're essentially Montgomery personnel anyway, there's no need to draw lines." Stealing my venue. And then trying to hijack my network to pave the way for Oliver. Victoria was nothing if not ruthlessly efficient. "Don't give them a single name." I dialed the director of a private contemporary art museum in the West Loop. They had been trying to poach our events for years. The moment I mentioned we were relocating the brand dinner, he agreed to close the museum to the public for three days and open their brand-new wing just for us. Half an hour later, the backup plan was locked in. Emma let out a massive sigh of relief. "What about Oliver's charity event?" "Whoever stole the venue can handle it. I'm not cleaning up his mess a second time." That afternoon, Victoria called. "Why didn't you give Oliver the guest list?" she demanded, skipping the greeting entirely. "Those are my firm's clients, not Montgomery Holdings' assets." "He just needs to borrow them once." Her tone was laced with irritation. "It's his first time hosting an independent event. Would it kill you to guide him a little?" It was his first gala, so his catastrophic mistakes were forgiven. It was his first event, so my hard-earned resources were supposed to be handed over on a silver platter. "I have no obligation to teach him anything." Silence hung on the line for two long seconds. "Nate, are you purposely trying to humiliate him?" "He stole my venue. I found a new one. I didn't try to stop him, and I didn't sabotage him." I let out a dry laugh. "What, if I don't personally lay the red carpet at his feet, it counts as bullying him?" Her voice went dead flat. "When you've finally come to your senses, you can call me." The line went dead. She was absolutely certain I wouldn't last a week before breaking. I turned to Emma and asked for the equity transfer documents I had drafted weeks ago. "Once this brand dinner is over, put the firm on the market." Emma’s head snapped up. "Nate, you’re really leaving?" "Yes." I signed on the dotted line, instructed accounting to pay out all employee bonuses, and severed every financial tie connected to Montgomery Holdings. Finally, I booked a one-way ticket out of the city. After dark, an alert popped up on my phone: Suspicious Login Attempt. The device was an old iPad I had left in the townhouse study. It contained encrypted client files, as well as working photos of me—escorting female executives to dinners, walking them into hotels, putting them into town cars late at night. I was about to force-logout when Emma called. "Nate, we have a massive problem. Someone leaked your photos to a gossip blog." Seconds later, my phone exploded with notifications. I clicked on the trending tab. The number one headline burned in bright, sensational red: Five Years, Seventeen Female Tycoons. How Many Women Has Chicago’s Most Expensive Kept Man Really Serviced? The headline stayed pinned to the top of the internet all night. I didn't call Victoria. She knew better than anyone whether those photos were real or fake. I had Emma pull the exact login logs from the iPad and contacted the blog that broke the story. At first, they refused to reveal their source. It wasn’t until I wired them a "cooperation fee" and threatened a federal defamation suit that they handed over an email address. I recognized the phone number linked to the email immediately. Oliver. He had even hired a retouching studio to systematically crop out the Montgomery Holdings company logos on the cars and remove the legal and PR staff walking next to me in the frames. With the evidence compiled, I drove back to the townhouse. Oliver was sitting in the living room, wearing my cashmere loungewear, unboxing a delivery of new tailored suits. On the coffee table sat my five-year aged Macallan. The bottle was open, more than half empty. When he saw me, panic flashed across his face. "Nate... what are you doing here?" I tossed the wire transfer receipts onto the coffee table. "Explain." Oliver looked at the papers, and all the color drained from his face. "I don't know what this is." "Do you need me to pull the IP logs from your email account, too?" I stared at him, my voice dangerously calm. "You stole the photos from my iPad, and you paid someone to write the expose. Oliver, if you want my job, just say it. You didn't need to play this dirty." Oliver’s lips pressed into a tight line, his eyes instantly welling with tears. "I just... I saw those photos, and they didn't look right. You were going into hotels with all those women, taking their money. How was I supposed to know what you were doing?" "You didn't know who they were?" I scoffed. "You transcribed the guest list for the gala by hand last week. All seventeen of those women were on that list. You knew exactly who they were." He just gambled that Victoria would protect him. "Hand over the uncropped originals and post a public apology," I said. "Or I will destroy you in court." Oliver clenched his fists, his voice cracking. "Nate, I wasn't trying to ruin you. I was just terrified Victoria was being used..." "That's enough." Victoria’s voice cut through the room. She strode through the front door, stepping directly in front of Oliver, shielding him from me. Her eyes swept over the evidence scattered on the table, her expression hardening. "Hasn't this gotten ugly enough?" she demanded. "You should be asking him that." I shoved the uncropped photos into her hand. "You know exactly who arranged those dinners, and you know exactly who those women are." Victoria barely glanced at them. "I know." "If you know, make him apologize." Oliver stood behind her, pale and trembling, his fingers gripping the fabric of her coat. Victoria was quiet for a long moment. "He was just being impulsive," she finally said. "The photos are already out there. Forcing him to apologize now will only pour gas on the fire." I stared at her. "And? Your solution is for me to just take the hit?" "I'll have the PR department kill the trending topics." Her voice was aggressively perfectly level. "The internet moves fast. In a few days, no one will even remember this. Oliver is young. He lacks boundaries. Let it go, Nate." I looked at the woman I had stood beside for five years, a deep, creeping cold spreading through my chest. "You want me to let it go?" Victoria frowned. "What else do you want me to do? Force him to make a public spectacle of himself and drag the company back into the mud? Nate, you've been in this circle for five years. You've heard worse whispers than this. The story will die. It's over." Because I never lost my composure, she assumed I couldn't bleed. Because I was always the "disciplined" one, she expected me to swallow every ounce of humiliation without a sound. Oliver gently tugged at her coat. "Victoria, maybe I should just apologize. Nate obviously cares a lot about what people think of him..." "You are not apologizing," Victoria snapped at him, before turning her cold glare back to me. "You were paid handsomely to attend those dinners for me. Now people are talking. Do you really need to take all your anger out on Oliver?" She took a step closer, her tone brooking no argument. "Drop the legal threats. Apologize to Oliver for cornering him. Otherwise, I suggest you pack a bag and move out for a few days until you calm down." I looked at her, and suddenly, I laughed. In her mind, all my resistance was just a temporary tantrum. She fully believed that once my emotions settled, I would slide right back into my designated slot. "I don't need a few days." I pulled my security keycard from my pocket and dropped it onto the coffee table. "I'll move out right now." Victoria’s brow furrowed tightly. "Nate, what kind of act is this?" "It's not an act." I glanced at Oliver, still cowering behind her. "He can have the townhouse. He can have the position. And as for your galas, your drinking games, and your endless messes—whoever wants to clean them up can be my guest." I looked directly into Victoria's eyes, perfectly calm. "I resign, Victoria." She stared at me for a few seconds, then let out a sharp, mocking laugh. "Don't try to threaten me with leaving." "I'm not threatening you." I smiled. "I'm notifying you." I turned and walked into the bedroom, pulling out the suitcase I had packed hours ago. My footprint in this massive townhouse was shockingly small. In my drawer, the Patek Philippe she had given me sat exactly where I left it. I didn't touch it. I dragged my suitcase down the hall and out the front door. Victoria never moved from the living room. She was probably waiting for me to reach the threshold, pause, and come crawling back. I climbed into the waiting town car and texted my lawyer. File the defamation suit. And send the final invoice to Montgomery Holdings. Every single cent. I turned my phone off. Outside the window, the warm lights of the townhouse faded into the distance. I didn't look back. "To the airport," I told the driver. 2