Ms. Jones and Kenny Ch. 01

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In an alternate world, Kenny is Ms. Jones's teacher aide.
6.3k words
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Part 1 of the 2 part series

Updated 08/09/2023
Created 06/26/2023
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"That's the bell! Remember to turn in your rough draft before class on Monday because I will not be extending the deadline again!"

Ms. Jones's reminder was washed away in the surge of students hurrying out of her classroom, eager to start their weekend. With a sigh, she aligned her stack of papers and started grading the quizzes from earlier. Glancing up, she took note of the last student leaving.

"Finally!" She said under her breath.

Ms. Jones took her phone out of her desk and pulled up a particular email she had received earlier in the day.

"Status: delivered. God, I can't wait to ride this bad boy tonight!"

Ms. Jones smiled as she bit her lower lip. She couldn't help but look at the many display images of the big, rubber cock she had ordered after a lengthy, personal debate.

"It's the first time in years that I've been horny enough for fingers and tit-rubbing to leave me wanting more..." she thought to herself.

Ms. Jones gently caressed her breasts, encircling her nipple with a fingertip, while still focusing on the highlights of her purchase.

"I'll yank my clothes off, get on the bed, slide him in, and just shout, "fuck me, fuck me, fuck me" over and over until my hips stick straight up in the air!"

Her free hand was reaching towards her crotch when the doorknob turning caught her by surprise. With a small yelp, she quickly locked her phone and put her hands on her desk. Her racing heart was calmed when she saw that the person who had walked in was just her teacher aide, Kenny Thomas. Kenny Thomas was a college kid in his early 20's, slightly above average height and build, and currently the recurring focus of Ms. Jones's late-night fantasies.

"All done with the front office?" Ms. Jones asked, resting her head on her intertwined fingers.

"Yep. Yet again, the power cord just slipped out so there was no need to have me reset all of the computers..." Kenny said in sigh.

"Was it Linda? She always takes the nuclear option," Ms. Jones added.

"Yeah, exactly! Like, check the damn cords first if the printer isn't on!"

Ms. Jones always enjoyed gossiping with Kenny. At first, she was weary of having an assistant but almost immediately grew to enjoy his company after hearing his remarks about the staff she didn't get along with.

"Oh, let me help you with that!" Ms. Jones said as she saw Kenny wiping down the whiteboard.

Ms. Jones joined Kenny before he could interject. As they cleaned the board, her off-balance constantly threw her against him.

"So sorry, 'hun! These are my favorite shoes but damn are they hard to stand in," Ms. Jones said before adjusting the straps on her shoes.

Ms. Jones wasn't the only one with a crush on her coworker, however. Kenny came to a stop as he looked over at her bending over. He looked her up from shoe to bottom, appreciating every aspect of her lower body for the short time he had. The fabric of her jeans stretched as she leaned forward more. Kenny was full-on staring when he noticed the outline of her panties pressed against her pants.

"Fuuuuck, her ass is packed in those pants!" He thought to himself.

"Dammit, Ava! Stop bumping into him! He doesn't want a sweaty teacher all over him!" She thought to herself in embarrassment.

Ms. Jones stood up fast, wanting to finish up cleaning to hide behind the safety of her desk. However, her feet were slow to catch up with her brain and she was now headed head first to the ground.

"Ms. Jones!" Kenny exclaimed as he reached for her.

Luckily, he was able to catch her by both of her arms and pull her up into his. Ms. Jones's mind went blank as she was enveloped by the firm embrace of young stud who had just saved her. She giggled with a goofy smile as she squeezed his arms and nearly fell weak in the knees. Kenny's calls to attention gradually brought her back to earth and she hastily stood back up with some assistance.

"Are you ok? That would have been bad if you smacked your head on the floor," Kenny said with concern.

"F-Fine! I'm fine! It's just I tripped over my own feet!" Ms. Jones said flustered.

Ms. Jones turned her back to straighten out her clothes while Kenny turned around to hide his growing sign of affection. Both him and her quickly wiped the board down then returned to their respective seats to finish up any remaining work for the day. Ms. Jones could barely concentrate on grading, minutely twitching when the intrusive thought of Kenny embracing her again crossed her mind. Soon, she started writhing in her seat.

"So, any plans for the weekend?" Kenny asked her.

"Plans! O-Oh, we'll I maybe had some errands to run," Ms. Jones said, sitting up straight.

"I don't have much either. There's no tests right now, so I'm just stuck at home," Kenny said with a sigh.

Just then, Ms. Jones got a spontaneous idea.

"Uh, hey! You know, since you've helped me out so much, how about I do something nice for you?" Ms. Jones suggested.

"Something nice? Oh, but I don't need a reward! This is part of my schooling, after all," Kenny said, refusing to accept any flattery.

"Nonsense! You've helped me out, the teachers out, and anyone else who's having issues with their computers. Besides, we're friends, right? We could spend a day getting to know each other better!"

Kenny reconsidered Ms. Jones's offer.

"Actually, I'd like that a lot!" He answered.

"Great! How about tomorrow? We could go to the shopping mall, get something eat, go back to my pl--play games at an arcade or something!"

Ms. Jones had a nervous smile as she wondered what Kenny would think about her freudian slip but honestly, he was too happy with the thought of spending time with his crush to pay attention to the suggested itinerary.

"Tomorrow's good for me. Although, we better do stuff in the afternoon since it's supposed to be bad weather in the morning," Kenny said.

"Ah, yes. Very true. Yes. Mmm..." Ms. Jones said, blindly agreeing with anything Kenny said while shoveling her work into her bag.

"Well, we better get home before someone drops in and asks us for help with something. I know Linda stays late on Fridays for office work and there's no telling what else she accidentally knocked out of place," she said while leaving the room.

"Oh, absolutely not!" Kenny said in a rushed tone, cramming his belongings into his backpack while chasing after Ms. Jones.

*****

The door to Ms. Jones's bathroom opened. Steam from a fresh, hot shower poured out into the bedroom as she walked in the midst of it. Sitting down on the edge of the bed, she reached over and picked up the package that was delivered earlier in the day. Her heart was racing as she tore the package open, pulling out the dildo she had ordered. Ms. Jones giggled as the toy smacked against her hand after she had dumped it out.

She was in awe as she worked her hands across the entire toy. From the big balls to the thick shaft, it was the first time she had ever had a toy like that and already knew it would leave her wanting more.

"Fuuuuuuck! Robert wasn't anywhere close to this! I don't think anyone else has been either, if I'm honest," she said to herself.

Despite her reputation amongst the student body of being an absolute femme fatale capable of taking down a 50-man gangbang with ease, she had actually been quite monogamous. While she was interested in trying out the many different acts she had seen in various porn videos on the internet, she never had the courage to ask or inquire for them.

Ms. Jones's smile soon faded into a grimace.

"Wait, how do I use this thing?" She said to herself.

Even with the knowledge of certain sex toys, the only other toy she had ever used was a back massager that she repurposed for clitoral stimulation.

"I can't just shove this thing in, so... maybe I need to warm up first?"

Ms. Jones took her bra and panties off, then lied back on her bed. Spreading her legs apart, she reached down and massaged her lips with her fingers. As her body started heating up, she stared at the blue dildo she held in front of herself. Gripping it by the base and pointing the tip across her torso, the thought of Kenny kneeling bedside her came into her mind. Her breathing became ragged. Her pussy dripped as if she had been going at it for hours. Ms. Jones had the uncontrollable urge to pleasure the rubber cock as if it were the young stud of her fantasies.

She licked and sucked on the tip of the cock, giving it wet kisses as she fingered herself deeper.

"Oh, fuck! I never knew sucking a cock could heat me up like this!" She thought to herself.

She looked up and imagined Kenny looking back down, panting with a pleasured look on his face.

"You like getting your dick sucked, baby?" She asked her fantasy. "I'll make you feel even better!"

Ms. Jones gave the dildo long licks down the shaft until she reached the balls. She pressed her lips against each ball before enveloping it into her mouth. Her pussy throbbed as her tongue traced each one before both at the same time.

"I... I'm gonna cum? So soon, too!" She thought to herself in surprise.

Imagining Kenny again, she took the dildo as deep as she could in her mouth. Her hips lifted in the air as she squeezed her clit between her knuckles. Her pussy clenched and relaxed as also squirted across her bedsheets. Opening her eyes, she imagined Kenny now kneeling over her torso with his cock in her mouth; which intensified her climax. By the time she had finished, she had came so much that she was utterly exhausted.

"Oh, my god... all I did was suck on the thing and it turned me into a mess," she said to herself.

Looking at the dildo, she once again imagined Kenny being the one attached to it.

"Oh, baby... The things we'd do if you were here..." She said to herself.

Ms. Jones brought the toy between her legs. She rubbed the underside of the shaft against her slit before taking herself by surprise and shoving it in. Immediately, she let out a loud moan while gripping the sheets with her other hand. It only took a few thrusts to make her cum once again.

"Cummiiiiiiiing!" She exclaimed.

Ms. Jones's hand quivered as she tried to resume fucking herself senseless. The rapid movement only brought her back and over the brink in a matter of seconds.

"Another one?!" She said.

After her hips slammed back down, she quickly pulled the dildo out.

"That... that thing is way too good..." she panted out.

"Fuck, just thinking about that being his dick was too much. What I'm going to do if that's the only way I'll cum now?"

Ms. Jones caught her breath before cleaning up her various messes.

"Well, I better stick to dreaming because it would take a real miracle or series or specific events to bring us together like that."

*****

Kenny couldn't stand still as he waited in front of Ms. Jones's front door. To his surprise, her house was on the street behind his own, just a house over from the backyard, too. Instead of driving over, Kenny opted to just walk the short distance. Even though he was an adult capable of making his own lifestyle choices, he didn't want to deal with his nosy parents prying into why he was spending the day with a much older coworker.

Kenny's attention was quickly brought from the welcome mat to the door as Ms. Jones opened it. Her attire wasn't that much different from what she normally wore at work. From top to bottom, she had on black sneakers, tight blue jeans, and a maroon sweater. Her curly, dark-red hair hung down to her shoulders instead of being bunched-up with clips. Her smile was just as warm as even, even if she was wearing lip gloss instead of her signature heartthrob, red lipstick.

"Ready to go, Kenny?" She asked him with a smile.

"O-Oh, definitely!" He eagerly responded. Ms. Jones grabbed her purse then locked the door. As discussed earlier, she would be the one driving today.

"The shopping mall, right?" She asked him.

"Yeah. You wanted to look around for a bit?" Kenny said back.

"Definitely! There's so much new stuff that came out that I haven't had the chance to check out."

With the first place of the day established, Ms. Jones headed off to the local shopping mall. Throughout the drive, she couldn't decide whether to make small talk or wait until they arrived at their destination.

"Shit, what do we even talk about?" She thought to herself. "We normally gossip about the teachers and front office. I wonder what kind of hobbies he has?"

"So, is there anything in particular you like to do when you're not working?" Kenny abruptly asked.

Ms. Jones's face lit-up as she eagerly talked about herself.

"Why, yes! I just love cooking! I'm always making and trying new things in the kitchen!" She said cheerfully.

"Now that you mention it, I don't think I've ever seen you leave to get lunch at work. Do you always make lunch for yourself?" Kenny asked.

"Yep! Every day! I usually make it the night before to sleep in some more in the morning... maybe I could make something for you sometime."

Ms. Jones nearly slammed her brakes when she realized what she had suggested.

"Oh, definitely! It would be great getting to try some of your cooking instead of just a ham and cheese sandwich," Kenny optimistically responded.

A confident smile crossed Ms. Jones's face.

"I might have to make a stop by that cooking-ware store while we're at the mall now~" she thought to herself.

Before they knew it, they had arrived at the mall. Upon exiting the car, Kenny gave Ms. Jones a quizzical look as she bent down then stood back up wearing sunglasses.

"What? So, this way no one will recognize me! It's not that being seen with you is a bad thing, 'hun, it's just that I don't want any rumors to spread about us if someone from the school sees us together," she explained.

Kenny thought that a disguise was useless since anyone from the school could recognize her from figure alone but chose not to say anything. Walking alongside her, he was thrown off by not hearing the usual click of her heels or wedges.

"Didn't you want new shoes since those other ones always throw off your balance?" Kenny asked.

"Oh, you're right! Yeah, I'm about to throw those things out! Should've never believed that $6 wedges would be good..." Ms. Jones said in a sudden realization.

"Those things are seriously a menace! Even though they go well with anything I wear, they put me on the floor sometimes. I remember the strap coming undone and putting me on my ass when I was leaving a pep rally one time. Thank god no one saw me because I was on my back, legs up and skirt hoisted over my a-"

Ms. Jones cleared her throat to prevent her from giving anymore juicy details about her spill.

"S-So, uh, how about a shoe store first?" She said, nearly blushing.

"Shoes would be good," Kenny absentmindedly said in agreement, his mind still fixated on imagining the sight Ms. Jones must have been.

Kenny took looked around at the numerous shoes he had no intention of buying, a feeling he--as a son--was all too familiar with. Ms. Jones perused through the numerous heels and wedges that caught her attention, eventually holding up two that stood out the most.

"Which of these would look better on me? The red wedges or the dark-blue heels?" She asked Kenny.

Kenny honestly liked it when she wore wedges instead of heels.

"I think the wedges would look pretty good on you," he answered.

"Red ones it is!" She said before putting the heels back.

Kenny took the free seat next to Ms. Jones as she slipped out of her sneakers and into the wedges. She took a few test strides. Kenny struggled to be secretive as he watched her hips sway with each step and dared not to look at her dead-on when she walked towards him.

"These feel absolutely perfect! Way better than those other ones I wear," Ms. Jones said, looking down at her feet.

"And I'll make sure to take good care of them, especially since you picked them out for me~" she said with a wink.

Kenny blushed at the compliment. He patiently waited in his seat as Ms. Jones checked out, totally not because he had a boner.

"Ready for the next place?" Ms. Jones said.

Since they had gone to her store first, Ms. Jones wanted to take Kenny to one he could find something for himself at. Walking past the other shops, they took a sharp turn into the trendy clothing store. Ms. Jones took note of all of the tops and pants she was interested in as she ushered Kenny to the small corner known as the men's section.

Kenny flipped through the hanging shirts, not particularly caring about what he found. His wardrobe at home mostly consisted of graphic and plain tees that he wore to college, the high school and as well as bed. Ms. Jones, on the other hand, already had armfuls of clothing she picked out for him.

"Hey! How about trying these on?" Ms. Jones said.

Kenny was taken aback by the absurd pile of clothes Ms. Jones gathered. Had this been anyone else, he would have walked away with a scowl but since it was Ms. Jones with an eager expression, he swallowed his disdain and took on the clothing.

The next several minutes consisted of Kenny modeling each piece of clothing Ms. Jones picked out for him. Had this been an 80's movie, this definitely would have been a montage with H*ey L*wis playing.

"Uh, what about this?" Kenny said, looking down at himself in a red polo and slim khakis.

"Oh, yeah... I'd definitely like to see you in this," Ms. Jones said, unknowingly eyeing-up Kenny with a suggestive smile.

"Because it looks so good!" She suddenly exclaimed.

Kenny didn't have a lot of polos or khakis, so he figured since Ms. Jones picked it out, he may as well give it a shot.

"I'm gonna go look at what I saw on the way in," she said from outside the changing room.

"Ok? I'm still gonna try on some more clothes in the pile!" Kenny responded.

Kenny thought about helping Ms. Jones pick something else out, but felt that his mind would wander too much for him to face her straightforward and opted to stay in the changing booth until she was done.

After a while, the two purchased their items and headed out.

"Now, I was thinking of going by the coo-"

Ms. Jones cut herself off when she noticed the gray sky through the skylight.

"Crap. I guess that 10% chance of rain was really 90%..." she said with a sigh. "We better get home. I know how much our neighborhood floods when it even sprinkles."

Kenny was saddened that he couldn't have more of the day with Ms. Jones. She too was also wilted that she couldn't end the day with lunch, but would settle for texting him through the rest of the day.

"Maybe I'll even send him some pics of me in my new clothes~" she thought.

As they left the parking lot, the rain started to really come down. Lines of other patrons with same idea populated the street and parking lot, making it nearly impossible to leave before things really got bad. By the time they were anywhere close to their neighborhood, the streets were already flooding. As expected, the entrance to the neighborhood's entrance was too flooded to enter.

"Fuck! Looks like the streets are flooded. Luckily, the GPS will take us around it," Ms. Jones said as she tapped on her electronic dashboard.

Now redirected, she kept going down the road. The more she drove, the farther away from the neighborhood they seemed to be.

"Uhh, I don't remember the other entrance being over here," Kenny said.

"We just passed the bike shop... yep, this isn't the way, car!"

Manually rerouting, Kenny and Ms. Jones finally found their way to the other entrance of the neighborhood. However, they stopped with a sigh as they saw numerous city vehicles setting up barricades.

"Really?! Even the other side?!" Ms. Jones said.

"Now what do we do?" Kenny said.

"We could get a hotel," Ms. Jones absentmindedly suggested.

Her eyes went wide, her face turned red, as she realized what had suggested.

12