Better Start Karen

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A Karen and an employee learn to get along.
2.9k words
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Jimmy, like many other people on this planet, hated his job. To him, the position he found himself in ran off of what he calls the three A's; aggravation, agitation, and aggression. Every word has constantly remained applicable to every facet of his workspace and the people within.

What, pray tell, is this catastrophic career choice of his? None other than retail work. He has faced it all; the incompetent supervisors, the coupon hoarding customers, the lazy coworkers, and last, but certainly not least, the Karens.

If you had asked Jimmy, he'd tell you there must be a nest of them hidden under the store's foundations. It's almost as if one shows up every day to suck the positivity out of all humans around it.

Expectedly, past events caused Jimmy's temper to be less than subpar. His lack of patience and care with non-Karen customers puts him on the brink of unemployment. The only reason management keeps him around is to deal with all the Karens, so they wouldn't have to.

And that has been the norm for the three years Jimmy has worked at his register. He'd love nothing more than to leave this joint and move to preferable opportunities. Alas, there were none for his lazy self. That was about to change.

On a particularly warm Friday in July, Jimmy was on the verge of breaking down. His ineptitude led to poor planning; having forgotten to bring a drink from home to work today. Without a chance for any breaks today, he was just about to faint.

The warm wave of sweaty customers all packed into the store did little to help. Caught between the heat and the consistent business, Jimmy was raring to go off. And go off, he did.

"Uh, excuse me," Uttered a melodious, yet irritating voice. "I need help finding the paper towels that are on sale, but I didn't see them."

Not looking up at the woman who dared make an inquiry to Jimmy, he sighed out loud. "There are signs everywhere and you can ask someone else!" He rudely replied.

Honestly, he half expected that remark to push this obvious Karen off to someone else. Proven wrong when he felt her grab his chin, pushing up his head to face her.

Despite her clearly rank personality, she was quite stunning to behold. This Karen stood much taller than all the others Jimmy has seen, reaching heights above most male customers, too. Her short brown hair had clearly been treated at salons daily, for who knows how long. And her plump lips, shaped into an angry pout, were just begging to be kissed or forced to suck on something.

With her arms at her sides, this Karen was aghast by Jimmy's attitude. Yet, in this pose, he could observe her entire form all he wanted. Her tight white blouse could barely contain her massive G cup breasts, for the buttons looked about ready to give.

A tight black skirt covered her lower body, although really didn't. The attire had such a short length, it couldn't even cover up more than half of her plump rear. With her long, shapely legs on display, they ended at petite feet, wearing a pair of lavender heeled thongs. With fake pink gems adorning the center of where the straps connected, it created an image depicting the feet of a goddess.

The clearing of a throat snapped Jimmy back to reality, remembering this beautiful mature form was inhabited by a demon. He stared into her sapphire blue eyes, feeling his will fall into their depths.

The Karen pulled Jimmy up and forced him out of his register station, allowing her to walk around to invade his personal space even further. And then it happened: he felt her point a finger to his chest.

"How dare you?" The rotten goddess exclaimed. "Who do you think you are to talk to me in such a manner? I am a paying customer; one who's worth more than your whole lifetime, five times over!"

Her words did nothing to Jimmy's ego, but they did serve to piss him off.

"I couldn't give a shit." He responded, it now dawning on him that he was looking up to this woman, due to her immense height. "You're the one who can't even read obviously marked signs and labels! Get out of here with your entitled, illiterate ass."

Turning to resume his shift, the Karen wrapped one of her long legs around Jimmy, pulling back to prevent escape. This allowed her to really get close to his face.

"And don't think I noticed you ogling me. You stupid, little creep! I could have you arrested for that." She hissed, nearly turning him to stone with her sapphire gaze.

At such close proximity, Jimmy was able to take in the scents emanated from this woman. Obvious fragrances of conditioners, lotions, mints, mixed in with the smell of smooth sweaty skin. Clearly the heat had gotten to her.....or perhaps it was from lust?

No, Jimmy threw away that thought. But his attempts to forget this woman's attractiveness failed. Blood flowed to his loins, steadily raising his manhood further and further.

The Karen gasped, feeling the warm rod slip between her thick thighs. Every minor shift of her position resonated through to Jimmy's tent, providing him tiny bits of pleasure.

"You gross pervert!" She shouted, pushing him away. "I demand to speak with a manager about this!"

As if on cue, one does arrive, more than likely having heard all the commotion already. "What's going on here?" He asks.

The Karen steps forward to explain what she suffered at the hands of the unruly employee, who still couldn't keep his eyes off of her. Getting to gaze upon her voluptuous body, ripe for mating, contained within too tight clothing, was just what he needed after this terrible summer day.

"These are very serious allegations, Jim." The manager spat, snapping Jimmy back to his senses. "We may have overlooked your actions in the past, but this time HR will be involved."

Wrong choice of words for the Karen to hear, realizing Jimmy was even more unfit to work there than she thought. It wasn't just the manager who couldn't craft reasonable senses at this time, however.

"Sorry, but she's fucking smoking!" Jimmy retorted. "I would tap her all day, every day if I could. Maybe it would help change her attitude at least!"

The Karen and the manager's jaws dropped; Jimmy had basically confirmed his crimes of harassment. "That's it; you're fired." The manager said, without a second thought. "We don't want you here anymore and I'll have to call the police."

Surely this was the end for ol' Jimmy; done in by the very creatures he had always dreaded. Along with his terrible morals and work ethic, of course.

But, an angelic guardian stepped forth to redeem him. "Now, hold on a second." The Karen interjected, getting in front of Jimmy so his rod rubbed against her butt. "I am more than happy to drop all charges on this young atrocity and your establishment, if he agrees to my demands."

"He'll do it." The manager replied, before looking to Jimmy. "You're still fired; however, if you do what she says, we will consider this as having not happened, so you can use this job as a reference."

The manager walked off, leaving Jimmy alone with the statuesque savior of his. She ripped off his apron and poked him in the chest, "Follow me to the women's restroom, or else." She murmured.

He did follow, if only to discover what horrors she would have concocted for him. Pushed into the larger stall at the end of the restroom, Jimmy still didn't look too pleased about this.

"Can't believe it; fired and stuck as a lackey? I'd be better of in jail than this." He cursed. The Karen would have none of it and pushed him to the floor.

Slipping her left foot out of her sandal, she placed it on Jimmy's face, commanding him to kiss her sole. "You crazy bitch; what is this about?!" He demanded an answer.

"I'm going to have you live up to what you said earlier. Oh, what was it; something along the lines of fucking me all day, every day, perhaps? It'd be an honor to do so; so you better start kissing if you want that." She explained, wiggling her toes on Jimmy's lips.

Outraged by this situation, he had half a mind to push her off and go to the cops himself to get out of this nightmare. However, from the lower vantage point, he can see that she wore a dark purple g string under her skirt. Wedged between her moist lower lips, he became aware that she was turned on by this.

Something in him changed. Whether it was to get laid or to have a chance at putting a Karen in her place, he obliged and practically made out with her foot. Chuckling, she switched to the other so he can repeat worshipping his new goddess.

Jimmy's attempts must've passed her test, for she got him off the floor and into his birthday suit. "Why exactly are we going to do this here?" He wondered watching his new mate setting down her purse.

She was turned away from him, wiggling her voluminous rear and shaking her wide hips, as she scavenged the purse. "There we are." She whispers, having acquired what she needed.

Stripping herself, the devious babe held out her arms to show off her nude form. The gigantic gazongas swayed heftily, now free from their disproportionate confinement. Perfectly shaped and glistening with sweat in the light, Jimmy followed their teardrop shape, finishing at her perky nipples.

Reaching out with his hands, Jimmy played with them so innocently. Watching as the bountiful boobage spilled out of his grip turned him on even further. He couldn't resist his primal urge to stick both her nipples in his mouth, proceeding to lick and suck them.

The Karen bit her lip from his initiative, as her toes curled from the attention to her mammaries. But, this was not how she was going to have things go. Bending forward, she picked Jimmy up and shifted his position to situate his rod between her tits.

Rather awkwardly, she used her previously hidden strength to hold him steady, as she bent her head down and took his tip into her mouth. With his shaft completely contained past her dick sucking lips, she increased the suction before pumping her head back and forth.

Jimmy grit his teeth, as the fellatio commenced. This Karen in control was very skilled, whirling her tongue around his tip and slurping his meat like a vortex. He was surprised that she hadn't even commented on his length before sucking on his rod, but figured she didn't mind. She must get off more from being in control, then just having a well endowed partner.

Alas, Jimmy could not hold out forever, just about ready to nut into the Karen's mouth. But, she stopped. "No, please!" He desperately moaned, before quickly covering his mouth, as if in denial to how he just sounded.

Knowing she had him under her spell, the Karen put Jimmy back into a standing position, lining his shaft up with her lonely hole. "You know what to do." She stated, as Jimmy thrust forward; his whole length being engulfed by her warm insides.

Now that they had officially started mating, Jimmy found that even standing full height, his face came up to the Karen's chest. That didn't deter his gusto, for he pounded her pussy with animalistic instinct.

Slick sounds from their connected genitals echoed off the acoustic bathroom walls, driving home that he was here for just one reason: to fuck this mature woman.

Thrusting brought his rod deep into the Karen's snatch, making her interior twist and coil. Her cunt surely wanted to milk his rod for everything he had; he knew this wholeheartedly.

This Karen may have acted like a bitch, but that's how she must get off. Having a shorter guy fuck her still put her in charge; it was what she must've wished for deep down.

Wrapping his arms around her soft body, he could reach her plush rear. Squeezing her cheeks, he used them for support to fully reach as far as he could into her. Yet it still didn't seem like enough. So, Jimmy decided to become even closer to her.

Lifting up his legs, one at a time, he too wrapped them around his larger partner's body. Clinging to her so desperately, he didn't relent in pounding her snatch as hard as he could.

She then interrupted, "I'm glad you figured out what I wanted." The Karen looked over her hands to review what she had pulled from her purse: a coil of polyester rope.

Smirking, she uncurled the fibrous material, before starting to wrap it around Jimmy and herself. Chuckling loudly, her blush face looked absolutely lost in this position of lustful authority.

Her submissive mate didn't bother look at what she was doing; too busy continuing his duties. Having lost all thought, thanks to the pleasure and pheromones of this woman, he remained still as she tied him to her body.

Effortlessly, she had tied herself and Jimmy up in some complex bondage. It held him so tightly against her body, even gravity couldn't undo these restraints. Even better was that it prevented Jimmy from removing his shaft from her pussy.

In anticipation of him trying to free himself, she had tied up his hands and feet behind her back, so he had no capacity to make any escape attempts.

"You're doing good, punk. Just keep going." She urged him; biting her lip more, now that this situation was completely in her control.

Jimmy, mindless drone that he currently was, motorboated her tits and kissed her skin, whilst his hips could not refuse crashing against hers. Her interior had gotten drastically tighter, pulling his shaft in to her furthest depths.

Sure enough, his tip poked against her cervix; the entrance to the place where he was to deposit his seed. With final grunts, Jimmy makes a few final rough thrusts, until his tip pokes through her cervix a tad.

Combined with her vice grip of a cunt, he shook as he unleashed a torrent of white warmth all over her insides. The Karen finally moaned as well, being filled up the finale for her to climax.

Jimmy remained taut for a bit, before going slack from exhaustion. This allowed his captor to fully redress herself, with her new mate safely secured underneath. This did little to make him less visible, however.

Now that Jimmy was done, he tried pulling himself out of this Karen. "Wait, what?" He wonders, finding his limbs locked in the same position. "What's going on?"

"Oh, you should know." She coyly replied. "I did what you said, and made it so we will have sex 24/7. You're my man now; my submissive little man that I've caught."

Jimmy struggles to free his hands. "You have got to be kidding me!" He cries, but starts moaning as the Karen walks out of the stall.

Each step sways her from side to side, making her interior change in tightness every so often. Every step effectively made her have sex with Jimmy, whether he wanted it or not.

"This is what we both wanted, sweetie." She mocked, grabbing his ass through her skirt. "Welcome to your new home."

Jimmy's vain attempts at struggling gave way to attempts at reasoning with her. But those too, ceased. His voice now taken up with moans and grunts, as the stimulation to his bits brought out his primal lust again.

He resumed thrusting, giving this milf what she wanted; portable lovemaking. Laughing evilly, she too occasionally moaned from the coitus they would be having forever.

Exiting the bathrooms, everyone they passed by were shocked by the sight. A tall milf trotting around, fucking a shorter man under her clothes was not on their list of daily occurrences.

Smirking, the Karen turned around once she reached the exit, ready to make a declaration.

"This here is Jimmy; he's my new companion. All of you remember, he belongs to me now!" She exclaimed, partially cut off by her own moans.

With that announcement made, she walked back to her car with Jimmy in tow. All this loving he was doing brought him to climax over and over. Steadily filling up this Karen's womb, he chuckled to himself.

He had succeeded in making this smoking mature babe his woman. She was keen on never letting him take his rod out, allowing him to blow as many loads as he wants into her.

Even though she believes herself the winner here, he realizes that is not the case. He had finally won against a Karen and would be able to enjoy the spoils of war, every second of his life.

She was all his now, and he'll be glad to fuck her all he wants. Her pussy agreed, clenching around his shaft to encourage more lovemaking. 'Of course, my love.' he jokingly thought. 'We'll never separate, ever again.'

Both of them moaned, locked in a prison of their own making. Never to separate; always cumming inside. But one thing's for sure; both of them are happier this way.

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AnonymousAnonymousover 2 years ago

Ok, I have a few issues with this.

The first being that you never gave a name to this woman that Jimmy hooks up with. Perhaps that was because you wanted to just make a character based around the Karen personality type, without making her relatable or redeemable.

Additionally, both characters seem to just be complete jerks. Especially with the ending, where you reveal that both of them are so arrogant, they each thought they won or were in charge. Clearly that was intentional, but it makes me wonder what kind of relationship you were trying to set them up with.

The woman sounds pretty at least, and their bondage situation is pretty interesting. Arguably it does sound a little more silly than sexy, since picturing a tall woman carrying around a shorter guy, tied to her in constant coitus, makes me laugh.

Focus on those points for any future bdsm stories you do; I think it would genuinely make for better content.

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