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After a brief farewell toast at the office, I convinced Kimberly for one last drink at my favorite sports bar, its air thick with the tang of beer and the hum of raucous cheers. With my new job secured in another city, tonight was my only shot. We’d shared playful banter at work, her laughter a spark that lit up the break room, but I’d kept my distance. Never fuck the company. A one-night stand wouldn’t have been worth the risk. Despite our age gap, I had to test my chances, especially with the odds in my favor. Word was, Kimberly was sexually adventurous, but choosy with her partners. Even a knockout like her needed to blow off steam with a raw, no-strings fuck now and then. Nothing beats that primal thrill.
Petite and curvaceous, Kimberly’s figure turned heads, her polished look rivaling any model. I’d stolen glances at her smooth skin and long, unbound hair, cascading like silk. Her tailored skirts and blouses, professional yet teasing, fueled fantasies of hiking up that hem, tearing her top open, and giving her the rough fucking a tease like her had coming. Those thoughts surged back as she raised her glass, her smile wicked, toasting our future. Our talk flowed, laced with flirtation, but her playful tone told me it was just a game—maybe a tease to get herself off later or to lure a younger fuck buddy. Fucking slut. She thrived on the attention, her every move calculated to leave men panting, cocks hard and hearts desperate. Sure, I could afford hookers, but I’d have dropped thousands to put this little bitch in her place, no matter how much I respected her as a colleague. I’d never hurt her, of course—just humble her, make her as open as her beauty demanded. You don’t flaunt a body like that, teasing every bastard in sight, and walk away unscathed. Someone’s bound to fuck you up.
The golf game on TV faded, replaced by election updates, just days away. Kimberly’s eyes narrowed at the screen, her lip curling. When I prodded, she scoffed, calling the frontrunner’s lead absurd. There should be a law against Ex-President's wives running for office. We are not in Russia, where couples just change seats. Surprisingly the topic did upset Kimberly. When I provoked her, she found the thought of Trump as President ridiculous and unbelievable. I saw my opening and proposed a bet on the outcome.
She laughed when I named her forfeit: “I want to fuck you.”
But she didn’t back down. Instead, she countered: “Fine. You lose, you bankroll a full day of shopping, my choice, up to your credit card’s limit.”
Maybe she thought I’d balk. “Alright, but yours is me fucking your ass until I cum. Deal?”
I extended my hand. She raised an eyebrow, pausing as the TV flashed odds heavily favoring one candidate.
Then she met my gaze, shook my hand, and grinned, her face alight with mischief. “We have a bet.”
I hadn’t expected her to bite, but I was game, even delaying my move to see it through. Three days later, I called, laughing my ass off at her expense. Once I calmed down, we set the time and place: her apartment, tomorrow.
The next morning, I took my time, shaving smooth and splashing on cologne, looking as sharp as a man my age could. I arrived punctual, roses in hand to coax a smile despite her loss. She knew me as solid, dependable, and let me in.
“Bet’s a bet, Kimberly,” I said, voice steady. “But I’m reasonable. You can buy out for $10,000.”
She rolled her eyes. “I don’t have that kind of cash.” Her modest apartment confirmed it—she was leagues below my pay grade.
“You’re young, with a good job,” I pressed. “Any bank would loan you that in a heartbeat.”
She waved me off. “True, but it’d take years to pay back. You didn’t bet for money, right? Let’s get it on and done.” Her eyes twinkled, that cocky pride in her body flaring again.
Maybe she was throwing an old pal a bone, a memory to jerk off to for life. Whatever her game, I wasn’t asking twice.
She dropped to her knees, yanking my pants and briefs down in one go.
“Wow,” she murmured, eyes wide at my cock. I didn’t hesitate, ripping her blouse open to grope her tits.
“In Texas, everything’s big,” I teased, chuckling as her brow furrowed.
I caught her swallow hard, likely sizing up how my dick would stretch her ass, make it sting. Size wasn’t everything to me, but I’d learned early I was packing—most guys envied my length and girth, a blessing and a curse.
“Please be gentle,” she begged.
“Not part of the deal, baby,” I shot back. “I’ll fuck your ass till I cum.” I laughed, her unease getting me harder, her trembling a fucking turn-on for what was coming. “Want to lube it with your mouth? Otherwise, I’ll just spit once on your hole to make it work.”
She rolled her eyes and started sucking, hands gripping my shaft. I grabbed her head, brushing her fingers away. “No hands or teeth, honey. Or you flip over now. Open wide and look up.”
She obeyed, and I took control, shoving her lips down to my balls, holding her there as she gagged, eyes pleading. “Admit it, you’re trying to cut my time with your mouth, right? Smart girl.” I moaned, loud and real. Her wide-eyed struggle confirmed it.
I pulled out, let her gasp three times, then drove back in, fucking her face full tilt, back and forth. Thick saliva coated my cock, dripping onto her chest—filthy, just how I like it. I kept going. Tears streaked her makeup, her nose ran, and I let her gulp, my prick deep in her throat. Fucking incredible. I choked her lightly, both hands jerking my shaft through her mouth. Her eyes reddened, her ass wiggling in pain.
I fucking loved it, especially since I never bragged about my stamina or cock. It was a rare payout when my fuck meat didn’t know I could go forever. Cardio, muscle cycles, a solid diet, and pelvic training kept me relentless, fat belly or not. I could hold a wet towel with my hard-on and fuck for hours. Kimberly was about to learn my real trick.
Mascara ran down her face, her throat raw after thirty minutes of my relentless pace. Despite my moans, I wasn’t close to cumming, though she hoped I was. She was breaking, damn near done. I could’ve convinced her to rather give me that $10,000 now if I kept at it.
Instead, I pinned her wrists with one hand, pressing her face to me with the other. “Want me to cum soon, Kimberly? Turn on a camera while I fuck you, and you can delete the file after. Agreed?”
She nodded, gasping. I released her throat, shoved her to the floor, and stripped her pants. She lay there, panting hard, barely moving. No rush now—she was spent. I set up three cameras I’d brought, their red lights blinking from sharp angles.
When I pushed my cock into her tight ass, she screamed, clawing at the clothes around her, biting her shirt to stifle the pain. I didn’t hold back, her whimpers stoking my arousal, though a twinge of guilt flickered—I knew her from work, wished her well. But now, she was my fuck meat, and nothing would ruin this. I pounded her ass, breathing heavy, then slowed to savor the tight warmth, her tits swaying, her muscles clenching, the cameras capturing every thrust. She’d prepped, keeping her floor clean. The red lights were a sweet fucking bonus, and we were far from done.
Give it to Kimberly—she took it like a champ, crying and whimpering for an hour before I made my next move. “Goddamn, Kimberly, this is fucking great,” I said. “I could go another hour. You want that? No? I’ve got cuffs and a gag—better than your shirt. Nod if you’re in.”
She nodded instantly. I gave her a breather, locking her wrists, ankles, and upper arms in black leather cuffs, their clasps snapping shut. I bound her wrists to her arms, her ankles to furniture with elastic bands. Then I forced an open ring gag into her mouth, its wide circle perfect for my cock. Time to let her taste her ass—her throat had rested enough.
I fucked her mouth for fifteen minutes before returning to her ass. I yanked her hair, slapped her cheeks. “Want me to spank you, baby? A break from the fucking, and it gets me hard. Might make me cum.”
She nodded slightly. I stripped my belt, expecting her to think I’d use my hand. Not me. One hand pulled her hair, the other lashed red stripes across her ass. I didn’t count, didn’t care—just whipped her struggling, cuffed body until I was satisfied. “Sorry, dear. Didn’t work. Still fucking worth it. Back to the fucking.” Poor Kimberly. Her suffering was my goddamn high.
I gave her another hour, switching between her ass and mouth, then sat back, pulling the gag to talk. “What a great fuck you are, Kimberly.” She whined, and I patted her head awkwardly. “You never stood a chance. Here’s my secret: I can’t cum without a specific trigger. I’ll share it, but only if you give in completely. Understand?” Her silence was all attention. “I can fuck you for hours, days even, with pleasure but no release. I’ve tested it. Great for me, shit for you. Comply now, or I’ll give you hours of hell. You know I can.” Tears streamed down her face, but she stayed quiet, my sincerity sinking in.
“Listen. Everything’s fine. Be brave a bit longer. I’m taking the gag off. Look at that camera and say you consent to me keeping these videos.”
Her eyes widened, she swallowed hard, but as I reached for the gag, she blurted, “Yes, I do.”
I smiled. “And can I show them to friends or post them online?”
Her tears fought to break free, but as I shifted, my cock twitching, she decided. “Yes, I allow you to,” she said, loud and clear.
I exhaled, steady and calm. “Well then, let’s finish this. Do what I say.”
I pounded her ass again, deep, slow thrusts. “Talk dirty. Beg me to fuck your ass.”
She whispered, “Fuck me.”
“Louder,” I snapped. “Be creative, scream it so the neighbors hear.”
She tried again: “Fuck my ass.” I upped my pace, moaning. “Fuck me rough!” she screamed, her voice breaking with potential. “I’m an anal slut. Take my ass. Give it dirty to me!” Painful cries slipped through as I gave her what she begged for. “Fuck this filthy whore, daddy. Fuck my ass! Yes! It hurts! More! Fuck my backdoor! Shag me! Fuck!”
We hit my best speed, her dirty words echoing, no doubt reaching her neighbors. I had everything but the climax. Leaning close, I whispered, “Someone needs to ask me to cum, darling.”
She lit up instantly: “Cum in my ass! Fuck my ass and cum in it! Fill me with your delicious sperm!” It didn’t take long. I spasmed into her, collapsing onto her back, squeezing her tits one last time. She didn’t even squeal.
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