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Chapter 37
by
Raljo
What's next?
Billy fights back, and tries to out-fuck this gorgeous milf
“Come onnn~, what are you waiting for~?” Kiara’s voice broke Billy out of his thoughts. He stared down at her open, waiting pussy, right between those thick milf thighs. It was so inviting… He needed it.
But he wasn’t going out like a chump. He wasn’t just going to stick his dick in her, and lose. He wasn’t going to cum like a one-pump nobody, then melt into her milfy body for cuddles. Something in him had snapped, and he decided he wasn’t going to give her control that easily.
“I’m gonna… Fuck you,” Billy dug deep, finding the strength to say the words. Between his legs, his perfect cock bounced with delight, as if excited after hearing his words. “I’m gonna… Make you cum. I’m gonna make you cum on my fucking dick, and scream my name.”
Kiara smiled, clearly not taking him seriously.
“Of course, honey. It’s only natural for you to want to serve me. I got into your brain,” she giggled. “Now… Why don’t you hurry up and… Mmmnnn~… Put it in me~?”
A fire was slowly building up inside Billy. The way Kiara was mocking him pushed him over the edge. Billy took a hold of her spread thighs, lining up his cock with her waiting cunt, and growled.
“Not… Your ****!” Billy yelled, as all as once he shoved his fat dick into the milf.
Kiara’s eyes bulged from the sudden insertion. The young man’s dick felt much bigger than she was prepared for, and even just from that one thrust was already stretching her walls so good.
“O-Oh! That’s-!” Kiara began.
Before she had time to get used to it, Billy had already grabbed her thighs harder and started pounding her. Deep, hard, and fast. His fingers sunk into her milfy thick thighs, squeezing tight as his fat cock assaulted her prized hole.
Kiara’s jaw dropped, taken aback by the strength and power this virgin dick was inflicting on her thicc milf body. A moan escaped from her lips, wavering in time with Billy’s rapid thrusts, as the young athlete just kept fucking her. It felt so good. His cock was poking all her best spots.
Seeing the effect his thrusts were clearly having on her, and watching as the dominance drained from Kiara’s face, Billy grinned. Happy to return the favor from earlier, he began taunting her, now that the tables had turned.
“You think you can just take my brain? Make it yours? Think again, bitch. I’m the champion for a reason. Your nerdy little certificate doesn’t mean a thing against my sheer power of will.”
His thrusts didn’t slow. Each powerful hip-connection was making the doctor see stars. She had never felt like this before - NEVER. And to think this young man was a completely inexperienced virgin, too… He really dick have the perfect cock.
Kiara was naturally dominant, but she didn’t mind switching things up every now and then. And with how fucking good this felt, she was more than happy to just melt into it and enjoy the rough fucking. She didn’t want to fight this. She wanted to bask in it. Her shuddering moans faded out for just a moment, her O-face lips moving to speak in a blissed-out voice.
“Yes… Yes… You’re so strong…” she mewled.
Billy smiled wider, enjoying the change in her demeanor. His cock was changing HER brain, now. Who was under whose control here, doctor?
His hips kept on slapping against that thick, soft ass, his dick relentlessly assaulting her experienced milf pussy. Plowing into her. He was like a beast. Kiara had never been ravished like this by anyone. She had even surprised herself in the way she had immediately fallen into her role, mewling and squirming cutely on her desk. The busty professional was completely at the mercy of his dick.
“Oh… Oh my god… You’re such a stud, you’re… OH!!!”
Shifting his angle a bit in response to her moans and reactions, Billy’s cock started reaching her deepest inner weak spot, and pounding at it. A spot that had only been touched by toys before, now getting exploited by a virgin. It felt so fucking good. His fat dick was mastering her pussy. Stretching her out so good, dragging along those sensitive folds with every brutish thrust.
How was a virgin making her feel this good? He had basically zero technique, just brute fucking strength. Exactly how talented was that inexperienced cock? Hitting all her best places, making her mewl, all without a thought behind his motions beyond “thrust, thrust, thrust”. Claiming this redheaded, intelligent milf for himself.
…Perhaps more importantly, what kind of a monster might he become if he became experienced?
The thought was dashed out of her brain as she just kept getting getting taken, getting claimed by a dick she had never expected to turn things around like this. The busty milf was getting fucked so good on her own desk, in her own office, completely stripped of her power. She was trembling, quivering, her dominant pussy squealing out in delightful surrender. This cock owned it, this cock fucking…
The rough motion of his thrusts naturally sent her big milf tits jiggling around on her chest. Billy reached out and grabbed one, presumptively, and gave it a nice squeeze that made Kiara whimper. Getting her hole pounded and her milf tits felt up by her patient - this young college athlete just taking what he wanted from her. Usually men melted in her pussy, but Billy was different.
He was just so determined. Just so manly. Out-fucking the milfy fox’s prized pussy, making her squeal on her desk. He had so much more willpower than she’d thought. She had underestimated him. Even after all her tricks, his brain refused to give in for her. All her smarts, all her gorgeous body, but he was able to resist. He was able to fight back, and fuck her hard, to save his mind from her educated clutches.
It was turning her on so much.
Such a brute. A barbarian. Making her submissive, taking what he wanted. She needed to serve. She needed him to feel the full weight of his victory, just as he was feeling the full weight of her hefty tit.
In a shaky motion, Kiara moved her face closer to his, taking it in both of her hands. She began laying sweet, trembling kisses all over his cheeks and his chin. Worshipful, delightful kisses from the milf he was fucking into total bliss.
Billy froze.
“W-Wait…” he stammered, pausing his thrusting to moan weakly. It was the first time his rapid rhythm had stopped since he stuck that perfect dick inside the gorgeous psychologist.
Kiara tilted her head, curiously. She leaned in and kissed his face some more, softly smooching him on the cheek. As her soft lips made contact, Billy shivered, trembling in place halfway in her pussy, frozen mid-fuck. His eyes rolled up in his head.
“Uhhhhhh…” he moaned, his hands softly squeezing against her thigh and bulky breast as he struggled to hold something in.
“Oh?” Kiara said, curiously. It seemed she had made quite the discovery…
This was her chance. The manipulative doctor smirked, and continued to kiss him. Cheeks, forehead, chin, lips, nowhere was safe from her gentle, doting affection. She held the sides of his head and pulled him in for more, wrapping her legs tight around him to hold him in place.
Billy shuddered weakly, but didn’t have the strength to pull away. Her leg-wrap had pull his cock the rest of the way inside her, fully wrapped up in that sexy milf pussy once again, and Kiara began squeezing rhythmically around his cock as she laid kiss after kiss upon him. Her dominant fire was slowly returning, as a delighted smirk crossed over her smooching lips.
“Wait… Wait…” Billy shuddered under the **** of her love, his cock struggling and worming around in her pussy.
Kiara paused her kisses to throw her head back and laugh. Billy just groaned, growing unsteady. His legs were weakening.
Not wanting to bother holding him up, Kiara simply flipped him over and got on top.
“What’s wrong, huh?” she asked smoothly, as those powerful, wide milf hips began pneumatically bouncing up and down. “Are you starting to lose steam?”
The sexy redheaded milf was riding him cowgirl, a smooth sultry lilt to her voice, her confidence growing as she pounded the young athlete down into her desk. Finally fucking the brute strength right out of him. Breaking down those walls, to take his brain from him.
He had put up a good fight… But that was over now. She had him. And there was no fucking way he could resist her cowgirl.
“Am I too much woman for you?” Kiara gloated.
“No… No… How…” Billy shook underneath her. How had everything turned around so fast…?
Kiara giggled. Smirking, she lowered her face, lovingly caressing his chin with her soft lips as she slammed her hips down onto his trembling cock.
Now firmly in command, Kiara continued to press kiss after sweet kiss onto him as the young man began losing control of his own body. She was taming him with her gentle, loving lips.
She moved from his face to neck kisses, softly smooching him right over his jugular. If Billy hadn’t felt like a cougar’s prey before, he certainly did now.
Her dominant hips were making his body tingle. The milf was pounding him with experience. He had been winning, but he couldn’t win against this - his affection weakness.
Her luxurious milf pussy was overwhelming his noob cock. Maybe he could’ve fought back harder with a little more experience - but there was no winning for him here. Not anymore.
Kiara’s lips moved back to Billy’s, and pressed a deep kiss right against them. Her soft, smiling lips giving love directly to Billy’s.
“Mmmmmmwahh~!”
“Gak! Cumming-!” Billy sputtered.
His body was shaking and spasming as his cock finally tapped out. Losing everything and giving up, his dick jumped and a purted deep inside the dominant redhead, spending the last of his energy as she began to laugh down at his pathetic face.
“Oh my~! You nearly had me there! Ahaha~!”
Kiara slowed her bounces as Billy’s spasms and spurts slowed, until she was just gently grinding on his twitching cock as it began to soften inside her.
“So…~ It’s affection, hm? THAT’S your weakness? How interesting ~” Kiara’s gorgeous face beamed.
“No… No… You can’t…” Billy moaned.
“Oh, but I CAN,” she sighed, pleasantly. “You’re mine now, darling. Alllll~ minneee~~ Hah!”
She reached out with a delicate fingertip, tapping the young man once on the forehead.
“Your brain… It’s mine to play with,” Kiara said. She began swirling that single finger around, tracing little circles over his mind. “All mine… Mine to shape and reform as I like it. Now that I know just where to hit you…”
“Noooo…” a weak moan was all the resistance Billy could muster, as he lay weak and spent on Kiara’s desk.
The beautiful woman smiled, and gave him a gentle kiss on the forehead that made him shudder.
“Yesss…” she corrected, nodding her head up and down at him with a wide grin.
It was the last thing he heard before he drifted off to sleep, exhausted. He had been utterly drained of his energy by this stacked psychologist milf, and he just couldn’t stop himself from passing out beneath her, his half-chub still inside the redheaded milf’s experienced, overwhelming pussy. Defeated. His weak spot isolated, and ready to be spread across his whole body.
The sight satisfied Kiara, who allowed herself a pleasurable shudder.
“Hmmm…~ Did my pussy knock you out?” she asked, slyly. “Or was it my goodnight kisses that drained you?”
She elegantly lifted herself off of him, unsheathing his dick and allowing it to limply flop back against his tired body. Standing over him, she placed a hand on her hip, taking in her conquest. Slumped on top of her desk, pantsless, a shell-shocked expression frozen on his **** face. That perfect dick, that had almost defeated her pussy, wilting and drooling onto his thigh.
He had nearly done something remarkable, and overpowered Kiara’s dominant pussy. But in the end, he just couldn’t keep up…
“This session has been a real breakthrough, Billy,” she smiled.
What's next?
Loaded Gloves
She has the advantage
Overconfident men getting their bells rung
Updated on Jun 12, 2026
by Raljo
Created on Jan 25, 2022
by Raljo
With every decision at the end of a chapter your game state can change. Here are your current variables.
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