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Smutember 2022
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Published:
2022-09-01
Completed:
2023-02-07
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23,266
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30/30
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178
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KidCapri's Smutember 2022 Shorties

Summary:

A collection of short & smutty one-shots based on the Smutember 2022 prompt list.

Pairings, characters, and content will vary by story. Pairings and characters will be tagged as added. Content will be noted at the beginning of each chapter, but will not be tagged due to AO3's 75-tag limit.

Chapter 1: Library [Kim/Ron]

Chapter Text

Sept. 1 - Library

Kim/Ron

Content: Public Blow Jobs


It may have been 10:30pm on a Tuesday night, but Ron Stoppable was at the ready. He sat next to his long-time best-friend-girlfriend in a secluded corner of Go City University's main library, but his eyes were locked on the closed dictionary in front of him. His fingers were poised to thumb through the massive book at his lady's command, and he couldn't wait.

Ron loved study sessions.

That could not be said during his Freshman year, when he had to do a lot of studying to catch up with his honor roll girlfriend. Thankfully for him, Kim was able and willing to create a way for him to develop good study habits. Now in his Junior year, Ron was a model student, yet the pair continued to use the same study training methods.

"You have 60 seconds. Are you ready?" asked Kim at half-volume as she eyed a small piece of paper in her hand.

Ron slid a small stack of adhesive note paper into position next to his book, then nodded. "Ready, willing, and able," Ron whispered back.

Kim brought out her Kimmunicator and set it on the desk. She brought up its timer function and positioned one hand over its start button. The other continued to hold her paper. "Five, four, three, two, one…"

Kim used her coordination to accomplish two tasks at once. She placed the paper face-up on the table with one hand and started her timer with the other. Ron's eyes rapidly scanned the page, taking in the puzzle he was supposed to solve:

Verb from the Germanic word schwelgan; Can also refer to a small, forked-tail bird.

Ron may have considered taunting Kim had they been anywhere else, but he didn't want to draw any attention to their corner of the library. Instead he opened his dictionary and quickly turned to a page three-quarters of the way through the book. He saw the word 'sharp' and knew he had to keep going. He thumbed through pages at a rapid place but slowed down as he approached his goal.

Skill. Smack. Spindle. Squire. Stardust. Superb. Svelte.

Ron's eyes lit up. He grabbed the sticky note and placed it near the top of a page. He reached over to Kim's device and hit the stop button to freeze the timer at 33.8 seconds. With an ear-to-ear grin he handed the book to his girlfriend. She took the dictionary, found the note, and read the word directly above Ron's mark…

…Swallow.

Kim gave her man a nod. She took a quick scan of her surroundings and saw that nobody was close enough to pay attention to them. With the coast clear, she dropped to her knees and crawled under the table between Ron's legs.

It would be ten minutes - and a few close calls from passing students - before Kim emerged from underneath the desk. And when she did, she proudly opened her mouth and showed that none of his essence remained.

She had made sure to schwelgan every drop.

Chapter 2: Partner Swap [Shego/James, Drakken/Ann]

Chapter Text

Sept. 2 - Partner Swap

Shego/James, Ann/Drakken

Content: Anal Sex


"That all you got?"

Shego's taunting did little to dull James Possible's enthusiasm. The villainess was bent over the side of his bed. He stood behind her, hands gripping her hips, plowing his cock into her tight ass. Shego held her cheeks open, which gave James easy access to her tightest orifice. All he could focus on was giving her everything he had.

Shego, meanwhile, constantly reminded him that 'everything he had' didn't amount to much.

"I said 'fuck my ass,' not 'make love to my ass,'" she snarled.

James was sure she was just teasing him.

He was mostly sure.

Pretty sure.

Still, he upped his tempo just in case. He couldn’t increase it much since he was already close to full bore, but he dug deep and found the will to thrust as quickly as he could. He held nothing back as he slid his length in and out of her pucker.

James would never dare plow his own wife’s ass nearly as hard as he was thrusting into Shego’s. Ann enjoyed letting her husband enjoy her ass, but she could only handle slow, shallow strokes until she was close to orgasm. Shego, with her comet-induced strength, had no such limitations.

Shego stifled a moan. "That's a bit more like it," she uttered. As much snark as she gave the older man, she did enjoy his attentions. She began to buck against his hips in time with his thrusts. She didn't move much, but she didn't have to. Her simple motions made things all the more enjoyable for him, just like they always did 

"Shego, I'm gonna…" He pressed his fingertips into her hips and pulled her back as he made one final thrust. He let out a mighty yell as stream after stream of his spunk filled the tip of his condom. Shego rode his shaft for a few more bounces to ensure that he was fully spent. She then pulled herself off of her partner, stood upright, and turned to face him.

"Good job, James," she said as she pulled the condom off of him and tossed it into a nearby waste bin. "You've been practicing with Ann, haven't you?"

James shook his head. "Oh no," he panted. "Not like this. She can't handle anything like this."

The villainess's eyes bulged in shock. "You sure about that?"

"Of course," he replied with confidence. Said confidence disappeared when his mind wondered why Shego would ask that question. With less gusto, he spoke again. "Should I be sure about that?"

"FUCK ME FUCK ME FUCK ME FUCK ME FUUUUUUUCK MEEEEEE!!!"

As she laid on the bed in Drakken's playroom, Ann Possible repeated the only two words she remembered how to say. The rest of her brain power was focused on savoring the sensation of 11 inches of one of the scientist's thick tendrils mercilessly sliding in and out of her ass.

Chapter 3: In The Rain [Ron/Tara]

Chapter Text

Sept. 3 - In The Rain

Ron/Tara

Content: Wet T-Shirt


The good news for Tara was that her plan was working.

The bad need for Tara was that her plan was working too well.

She wanted to tease Ron. They were both newly single and about to start college. He'd likely have no problem finding a girl that would be into him, and in all honestly she probably wouldn't have any issues finding a guy. Part of her hoped that Ron would be that guy, but she didn't want to push the issue.

Her solution was to tease him. She asked him to help her clear her parents' lawn. She could wear something a little more eye-catching than usual, and if she caught his eye, great. And as best as she could tell, her white t-shirt worth no bra underneath did get him to try and steal a few extra glances at her, just as she hoped.

But then it started to rain.

And then her house key broke.

With no shelter nearby, all Tara could do was stand there as Mother Nature turned her yard work session into a wet t-shirt contest.

Ron took her by the hand and led her to his motorbike. The pair rode through the rain to his parents' home.

And then his house key broke.

Which led to this moment. Tara was in Ron's treehouse. She was sitting on the couch next to her crush, who was looking at everything in the shelter except the woman in a translucent shirt with no bra underneath. And to make matters worse, neither of them had uttered a word for the last five minutes.

"I'm sorry."

Tara's jaw dropped. She heard those words come out of Ron's mouth, even though he did nothing wrong. In fact, she was a couple of seconds away from saying those words herself.

"Why are you sorry?"

Ron blushed and gazed at the floor in front of him. "Because I… kinda… sorta… looked… at your…" He sighed. "Ya' know, your… boobs."

Tara was dumbfounded. She had seen this day going in a number of different ways, but none of them involved Ron apologizing for looking at her. She shook the thoughts from her head, however, as his apology brought a new question to the fore of her thoughts.

"Ron, I need you to answer this honestly," she said. "Are you apologizing because you didn't want to see them or because I didn't want you to see them?"

"Oh, I definitely wanted to see them," he replied without thinking. An instant later his mind processed the response he gave and he turned red. He slapped his hands over his mouth and eyes to prevent himself from digging his grave any further.

The sight was enough to get Tara to giggle. Even in this strange, awkward situation, Ron was still Ron. That thought made her next move much easier. She stood up and faced him, even as he kept his face buried in his hands.

Ron was shaken from his panic attack by the sound of something hitting the couch near him. His head shot up and he turned towards the source of the sound to see a piece of white fabric hanging over the back of the couch. A moment's inspection revealed that it was a shirt. Specifically a wet, white t-shirt. The gears in his mind turned as he realized where that shirt had been moments ago. He slowly scanned the rest of the structure until his eyes settled on the now-topless Tara.

"Ron," she said gently, "I want you to look. In fact…" She slowly walked towards him, grabbed his wrists and pulled his hands towards her breasts, leaving them hanging just inches from her skin. "If you want to do more than just look… you can do that too."

Ron looked her in the eyes, and she responded with a nod. Without another thought, he closed the distance between his hands and her breasts.

That afternoon, he did much, much more than just look.

Chapter 4: Cruise [Junior/Male OC]

Chapter Text

Sept. 4 - Cruising

Junior/Male OC

Content: Cruising, Cheating, Oral Sex, Cum Swallowing


Senor Senior, Jr. was unrecognizable in his nondescript gray hoodie and sweatpants and his dark sunglasses. This was by design. The order of the day was anonymity. All of his clothing was designer, of course, but the day's ensemble was all about blending in.

The one part of his look that did stand out - both metaphorically and literally - was the bulge of his half-hard cock unrestricted by underwear. This was also by design. The more focus on his dick, the less focus on his face and the less likely be was to be found out.

Junior walked down the park path to a bend in the trail. If what he read was true, it was the place where like-minded people gathered at all times of the day, even at this early hour just after sunrise. He rounded the corner and saw another person staring at their phone while aimlessly wandering around.

A cursory look at the stranger confirmed that they were lanky but in-shape, and the slight dashes of white peaking through his black goatee erased why doubt of their age. Beyond that, Junior only noted their lips; namely that the stranger licked them when they gazed at his crotch.

Junior looked in both directions of the trail, checking to see if anyone else was in the vicinity. Finding nobody else, he locked eyes with the stranger and jerked his neck to indicate where they should go. The villain walked off the path and into the surrounding wooded area. He found a clearing and stood behind a tree at its edge, hiding him from view from the path.

Seconds later the stranger was with him. They dropped to their knees and pulled Junior's sweatpants down to expose his thick, shaved cock. At once they swallowed its length in one go. Junior grabbed the back of their head to help them in their efforts, then quickly set the pace of their bobbing. The villain was fully hard within moments, but the stranger had no problems accepting his full size in their throat.

Junior wanted to get lost in the pleasure and allow his partner to savor the taste of his cock, but he couldn't afford to. He kept his head on a swivel, constantly on the lookout for anyone who might intrude on their fun. That task grew more and more difficult as the stranger used their skills to the fullest. One hand massaged his balls while the other worked whatever part of Junior's shaft they couldn't fit into their mouth.

A few minutes of work were all Junior could handle. He tapped his partner's shoulder to inform them of what was about to happen. The stranger pulled their mouth off of his cock and left it open wide at his tip. Junior grabbed his own shaft and worked it hard and quick. It was a matter of seconds before he let out a grunt and began to shoot his seed into their waiting mouth. They let several strands of his cum pool in their mouth before swallowing down his essence. They gave his cock a couple more quick sucks to ensure that he was fully spent.

Then it was over. The stranger walked away without a word. Junior quickly pulled up his pants and waited in place for about a minute. Satisfied that his playmate was far enough away that he wouldn't arouse suspicion, he made his way back to the path.


From atop a distant hill, Bonnie Rockwaller watched the scene conclude through her high-powered binoculars. She wished she could be shocked, but what she had just witnessed answered so many of the questions that had hung over their relationship. If she was upset about a, it was that he hadn't told her about his desires. They could have worked something out that would have allowed him to have his fun and keep up appearances for the public, so long as she had the same opportunity. But now?

In truth, she would still be willing to play ball. She did love him, even if their relationship had been barely romantic and completely asexual for months.

But without his honesty, it was no longer a relationship. Now it was a transaction. Her cooperation was now a business transaction, and he would have to pay top dollar to get it 

Chapter 5: Don't Get Caught [Ron/Yori]

Chapter Text

Sept. 5 - Don't Get Caught

Ron/Yori

Content: Oral Sex, Tentacle Sex


Yori's plan was almost perfect.

The ninja woman laid out her plan for next evening's mission while the pair shared a bed. She and Ron would take a boat under the cover of night to Nagata's floating lair. They'd infiltrate the structure through an exhaust pipe, find the magical katana which Nagata had stolen, sneak out, and return the treasure to its rightful owner. Everything was going to go perfectly. Yet there was one thought gnawing at Ron that he just couldn't shake.

"Hey Yori," he began, "what do we do if we're on the boat and we get caught by the takokaiju?"

Yori turned towards her partner with a questioning look on her face. "Takokaiju? An octopus monster?"

Ron nodded. "I heard stories of them jumping out of the water and grabbing beautiful women and..." His cheeks took on a crimson hue. "Having their way with them."

Yori gave her boyfriend a suspicious eye, then broke into a soft fit of laughter. "You and your American-style jokes."

Now it was Ron's turn to sport a confused look. "What's so funny?"

She placed a hand on her boyfriend's shoulder. "You do not need to worry about these octopus monsters you speak of. They are not real."

"They're… they're not?"

The ninja shook her head. "They only exist in old art and movies." Her eyes narrowed. "Especially the movies in the folder of your computer named 'Not Ron's Porn.'"

Ron's face turned beet red. "You, um… found that, huh?"

Yori couldn't help but smirk. "We can discuss that later. What matters now is that you have nothing to worry about. There are no tentacle monsters that will have their way with me."

Hearing Yori utter his fear aloud made Ron realize how absurd he sounded. "I guess I'm being silly again."

"You are," she said flatly, "but I'm flattered that you care."

"Of course I care," he replied quickly. "I love you."

"I love you too, Ron-kun." She smirked again. "But I hope you aren't just saying that because you'd like to have your way with me with your tentacle."

He shook his head. "As much as I'd like to, I figured that it's off the table after you found those videos."

"You attacking me with your tentacle is out of the question tonight… but I said nothing about me attacking your tentacle."

Before Ron could realize what was happening, Yori had already yanked the covers off of him and pounced on top of his legs. Her mouth quickly enveloped his shaft, which sent Ron into a tizzy. He hardened quickly in her mouth, but her deft skills ensured that she would be able to accept his entire length, even at its full size.

Most of Ron's brain was focused on keeping himself from cumming immediately. What little free brain energy he had was spent on kicking himself. Why did he doubt his girlfriend's abilities? He wanted to keep her safe, but Yori needed no protector. She was fast and nimble, and could easily take care of herself.

Clearly he had nothing to worry about.

Still, he thought that he'd take a moment of the next day's training session to figure out how to turn the Lotus Blade into a harpoon gun. Just in case.

Chapter 6: Just One Bed [Shego/Drakken/Ann/James]

Chapter Text

Sept. 6 - Just One Bed

Shego/Drakken/Ann/James, Shego/Drakken, Ann/James

Content: Implied Swinging


The check-in agent tried to be as tactful as she could, but she was in a bit of a predicament. "I'm sorry," she said, "you wanted the… Riverwalk Room?"

"Yes," answered James. His wife Ann nodded in agreement beside him.

The check-in agent turned to the other couple at the desk. "And… you wanted the Riverwalk Room as well?"

"We did," Drakken replied. Shego was thumbing through her phone a few steps away, close enough to hear the conversation but far enough away to stay out of it.

The agent's head swiveled back and forth between the couples as she struggled to find her words. "I'm sorry, but… I must inform you that the Riverwalk Room only had one bed."

"We're aware," chimed Ann.

The worker gulped. She wasn't sure she was making the situation clear. "The, um, couch… is rather small, and it's not a pull-out sleeper."

Drakken nodded. "We figured as much."

The staffer started to really sweat. "There are no… connecting rooms, so… you'll all be-"

"That's it!" Shego shoved her phone in her pocket and stormed the short distance to the desk. "Listen here… Connie ." Her voice dripped with disdain as she read the worker's name tag. "We know that there's only one bed in that room, and we're okay with that. You wanna know why? Because we're going to fuck."

Connie began to pale as the subject she tried to avoid was broached. Shego paid the staff member no mind as she continued her rant. "Yeah. We're going to fuck . A lot. First me and my man are gonna fuck while those two fuck. Then I'm gonna fuck her man and she's gonna fuck mine. Then I'm gonna fuck her while the guys watch because they aren't into each other even though I think it would be kinda hot.

"Then it's gonna be a free-for-all and we're all gonna fuck each other until we fall asleep. Then you know what we're gonna do?" Connie, who was white as a ghost, shook her head. "We're gonna wake up, come downstairs, eat your crappy continental breakfast, then go upstairs and fuck again until it's time to check out. So yes, Connie, we are fully aware that there is only one bed in the Riverwalk Room."

Four sets of eyes settled on Connie to see what she would do next. She struggled to regain both her composure and the color in her face. After a deep breath to collect herself, she did the only thing she could: She activated four room keys, placed them in an envelope, put on a professional smile, and handed the envelope to James.

"Breakfast starts at six," she said.

Chapter 7: Special Occasion [Kim/Ron/Josh/Brick]

Chapter Text

Sept. 7 - Special Occasion

Kim/Ron/Josh/Brick

Content: Gangbang, Triple Penetration, Anal Sex, Oral Sex, Vaginal Sex, Creampie, Ass To Mouth, Cum Swallowing


Ron had said that it was a special reward for a special occasion.

Josh called it a chance to reconnect.

Brick referred to it as a night to blow off steam.

Ultimately, Kim didn't care what any of them called it or how they referred to it. All she cared about was that it didn't end anytime soon.

All four college students found themselves nude and entangled on Kim and Ron's thankfully-large bed. Ron was on his back with Kim leaning back on top of him, her ass traveling up and down his shaft. Josh was on his knees between their legs and driving his length in and out of her folds. Brick was beside her head with a firm grip on her hair. He guided his thick cock down her throat whenever she wasn't moaning in absolute ecstasy.

Kim wasn't sure how many times she had orgasmed already. So many of them had happened back-to-back that she wasn't sure when one ended and another began. The physical pleasure was a big part of her enjoyment to be sure, but she also enjoyed how deliciously naughty it was to be the center of attention. She knew there were lots of guys in the world who would do anything to be a part of this moment with her, but the fact that all three guys involved genuinely cared about her let her relax and truly enjoy herself.

Ron wanted to do something special for her 20th birthday. His big idea came when he heard her mumbling during what appeared to be a very good dream. After a couple of delicate and difficult conversations, Kim gave her boyfriend the go-ahead to set something up. She assumed that he would reach out to people they barely knew. Instead, he talked to old acquaintances who happened to have become good friends in college.

For that, Kim was incredibly thankful.

"Cool if we switch?" asked Brick. He looked around and saw nods of agreement from each of the other guys. He and Josh each took a step back to give everyone the chance to untangle. Kim let out a whimper when each of her playmates pulled out of her. She positioned herself to push off of Ron, but took the opportunity to rock her hips and take Ron's full length up her ass, much to her boyfriend's enjoyment. She bounced on his length a few times before finally sliding off of him.

The guys wanted to make the pause as short as possible, so they moved quickly. Brick laid on the bed the moment Ron got up. Kim quickly pounced on top of him and straddled him. She positioned her snatch to meet the tip of his shaft and slowly slid down as much of his length as she could. She bent forward and spread her ass cheeks apart, letting Josh know exactly where she wanted him. He quickly grabbed the nearby bottle of lube and prepped both his shaft and her entrance before fulfilling her unspoken request.

Ron began scanning the room for a washcloth that he knew he had brought in before things started, but his search was interrupted by a hand grabbing his wrist and pulling him back towards the bed. Once he was close enough, Kim grabbed his cock and tried to take it into her mouth. Ron quickly took a step back.

"Kim, I didn't get to-"

"Don't care," she said as she yanked him back towards the bed. She took his cock head into her mouth and began bobbing up and down his length, taking more and more of him down her throat each time. Ron's concern about hygiene lingered, but the familiar feeling of Kim's throat around his dick quickly pushed everything else out of his mind.

It wasn't long before Kim felt Josh pull out of her ass. She whimpered at his withdrawal, but she thought she knew why he did it. Seconds later, a loud groan and the feeling of something wet splashing across her back confirmed her guess.

The one benefit of not having a cock in her ass anymore was that it freed her hips to match Brick's rhythm. She set a torrid pace in hopes of making up for the fact that he was too thick to take completely. Brick's tone changed instantly, and he grabbed her hips in an attempt to slow her down a bit.

"You're gonna make me pop if you don't slow down," he pleaded. Any doubt about her intentions disappeared when she somehow bucked even faster on him. He now understood that holding off was a losing battle. He tightened his grip on her hips and pulled her down as far as she'd comfortably go before unleashing his cum inside of her. She grinded her hips to milk every drop she could from him. Once he was fully spent, she scrambled off the bed and onto her knees to give Ron her full attention.

Once she was in position, Kim bobbed her head up and down his full length, her nose smashing into his pubic hair again and again. This was her cheat code to get him to cum hard, and she was about to get what she wanted. He pulled back enough so that his tip was positioned at the entrance of her mouth before he began to fill it with his hot seed. Her hand worked his shaft to pump every drop of his essence. Once he was fully spent, she showed him that her mouth was full of his seed and made a show of swallowing all of it down.

"Hey Josh." She made sure she had Josh's attention before running a finger across her back, gathering up some of his cum, and licking her finger clean. She turned to Brick and saw that she already had his attention, so she gathered some of the cum dripping out of her pussy and gave him a similar show.

"Is it cool to say 'happy birthday' after all that?" asked Ron. The other three participants chuckled.

"I think so," replied Kim, "but I want to say 'thank you' first." She got up from her knees and kissed Josh on the cheek, then did the same for Brick. She then turned to Ron and kissed his cheek. "You get a special 'thank you' later."

Ron blushed. "I don't know what would be more special than this, especially after you… right after it was in your…"

Kim ran her fingers down Ron's chest. "Since you got a couple of friends to help celebrate my birthday, I was thinking about getting a couple of my friends to help celebrate yours ."

Ron smiled the biggest smile he had ever smiled. "Booyah!"

Chapter 8: Be Quiet [Ron/Monique]

Chapter Text

Sept. 8 - Be Quiet

Ron/Monique

Content: Vaginal Sex


Monique couldn't speak. She couldn't scream. She couldn't yell. She couldn't make a single sound.

Ron's hand over her mouth was a reminder. It didn't stop her from making noise, as his grip was relatively gentle. But it was enough of a reminder to keep her silent. Or at least as silent as she could be, considering that Ron was fucking her doggy-style and sending jolt after jolt of pleasure through her core.

Her parents were just down the hall, a few steps away at any given moment. They should have been asleep by this time of night, but she couldn't be sure. They'd check on her if something was amiss, and the sounds of her having an earth-shattering orgasm at the hands of the boy she insisted was just a friend would definitely fall under that category.

Part of Monique's mind wanted to be as loud as she wanted to be. Part of her wanted her parents to see this. Okay, not actually see it because that would be gross. But know it was happening. Know that she was an 18-year-old woman. An adult. To understand that she was not a kid anymore. To stop assuming that she was some naive kid that the world would chew up and spit out once she left the protection of her parents' roof. To know that she was going to live her own life she make her own choices.

But the time wasn't right. She knew that her parents had a strict 'our house, our rules' mindset, and she wouldn't be out of their house for a few more months. As much as she wanted to show off Ron, it was a fight that she knew she couldn't win just yet.

But once she was in her own place, it would be 'Monique's house, Monique's rules.' Those rules would include that she gets to be an adult. She gets to make her own decisions and, inevitably, mistakes. Ron gets recognized as more than just a friend. Nothing gets to stand between her and Ron as a couple. Once she gets to take the medicine her parents insisted she didn't need yet, not even the thin barrier they relied on now would come between them.

And they'd get to make all the noise they want.

But that was the future. For now, all she can get is the silent pleasure of his warmth behind her and inside her.

Moments later Ron would plant his lips on her neck to keep himself silent. He would freeze up and she would feel the sensation of warmth at his tip, albeit dulled through a layer of latex. She'd fell kisses on her neck, then on her lips. Then he would pull out and throw the condom in a small plastic bag that he'd throw in the garbage at his own place. He'd get dressed, give her another kiss, then climb out the window as silently as he had entered minutes earlier.

She had succeeded in staying silent and not getting caught, and she was glad that she got at least some time to be intimate with her man. But she longed for the day when she could cum hard on his dick and let the world know how good he was to her.

That day couldn't come soon enough.

Chapter 9: Surprise Sex [Kim/Ron]

Chapter Text

Sept. 9 - Surprise Sex

Kim/Ron

Content: Hand Job, Domestic Fluff


Few things were sexier to Kim than the sight of Ron cooking in a t-shirt and boxers. It was just the right combination of the best of her boyfriend's best physical and emotional qualities that hit her in all the right ways. It was the image that blessed her vision when she entered the kitchen, and it inspired her to try something a little different.

Ron jolted when he felt something against his back. It took half-second to realize that it was Kim, and another half-second to realize that she was topless. “Good morning, KP,” he said once he had his bearings.

Good morning?” she said with a hint of playfulness in her voice. “I was hoping for a great morning.”

“Well how can I make it-” Ron’s eyes bulged when he felt Kim’s hands snake around him below his waist. They quickly reached the front of his shorts and reached inside its opening to find the prize inside. “Kim, what are you doing?” he asked.

“Making it a great morning,” she replied dreamily as one of her hands took hold of his cock and began to slowly jerk it to life.

Ron held back a groan for a few moments before eventually caving to her wiles. He relaxed into her as she began to up her efforts to get his cock to stiffen. But just as quickly as he relented, he shook himself free of her grasp and stepped away from her. He had a look of regret across his face when he turned to face her, and that look only grew stronger when he saw a bit of hurt in her eyes.

“Did I… Did I do something wrong?” Kim asked meekly.

“Nonononononono!” Ron shook his hands in front of himself in a panic. “You didn’t do anything bad, just… maybe not the best timing?”

Kim nodded. “Sorry for just assuming you’d be okay with that.”

Again Ron shook his hands. “Nonono, I’m okay with it. I’m totally okay with it.” He took a deep breath. “Just maybe… not when I’m messing with hot oil?”

Kim arched her brow in confusion. That confusion gave way to understanding when Ron stepped aside to reveal that he had a deep pan full of bubbling oil and diced potatoes.

“Yeah, I’d rather not have to call your parents and explain how you got second-degree burns on your breasts.”

Kim let out a chuckle and kissed his cheek to let him know that everything was okay. “I love you.”

“I love you too,” he replied before turning his attention back to his potatoes. After a moments thought, he turned back towards Kim in a panic. “I can make cold cereal… tomorrow… for breakfast… if you want to… y’know…”

Kim smirked, then began walking seductively back towards her husband. "I think that might work…" She brushed up against him. "As long as you can serve up a side of hot… thick … sausage." She punctuated each of her last words with a rub against Ron's shaft.

"I think I can serve up some-"

POP

Ron's head snapped back towards the stove top at the sound of oil popping. He adjusted the knob to turn down the heat, then gave everything a stir.

Kim let out a chuckle. "I think this is the cooking gods telling me to leave you alone…" She leaned into him and placed her lips next to his ear. "...Until after breakfast."

"Booyah."

Chapter 10: Double Penetration [Ron/Shego/Drakken]

Chapter Text

Sept. 10 - Double Penetration

Drakken/Ron/Shego

Content Tags: Threesome, Double Penetration


"I don't think this counts!" cried a naked Ron as he sat on a chair in Shego's bedroom.

"It undoubtedly does," Drakken replied. He stood at the side of the room as one of his vines was spiraled around Ron's shaft. Shego had straddled Ron and was slowly riding their combined manhood.

"Yeah, maybe by the letter of the law, but not the spirit ," Ron countered.

"Nyah , the letter of the law is the spirit of the law. That's how laws work."

Shego let out a groan of annoyance and dismounted from Ron. "What are you two arguing about now ?"

Drakken pointed at Ron. "He's saying that this doesn't count as double penetration, even though both of us are penetrating you."

"It's supposed to be two things!" Ron whined. "Right now it's just one thick one."

"It's your penis and my tendril," the scientist replied smugly. "That's two."

"We're both supposed to be inside of her," Ron said with a shake of his head. "Right now I'm inside of you and you're inside of her."

"That means we're bo th inside of her, doofus!"

"You're inside her. I'm inside a thick, viney condom that doesn't let me feel anything."

"Well I don't hear you complaining about it."

"I'm complaining right now! "

A nearby lamp exploded into cinder in a flash of green, bringing a sudden halt to the argument. The two men turned to see Shego with a look of near-disdain on her face. With full command of the room, she untangled Drakken's tendril from Ron's shaft. She brought the two together so that they were side-by-side with their tips aligned.

"I'm only going to say this once," she stated. "I'm going to hop back on and ride you until I'm done, and I don't want to hear another word out of either of you until I say you can speak. Is that understood?"

Both men nodded.

"Good." Without any further delay she jumped back on top of Ron and slid herself down both shafts. She needed a moment to adjust to their combined girth, which stretched her in a different way than the previous setup. But it only took the villainess a few moments to get used to the feeling, and she was soon bouncing on both phalluses at full blast. Both Drakken and Ron remained silent as she rode, although it was a greater challenge for Ron since he got pleasure from the feeling of Shego's folds that Drakken couldn't.

Between the sensation of being completely filled, the feeling of Ron's cum splashing inside of her repeatedly, and the lack of annoying comments from either of her partners, Shego found the proceeding hour to be absolutely perfect.

Chapter 11: Just The Tip [Bonnie/James]

Chapter Text

Sept. 11- Just The Tip

Bonnie/James

Content Tags: Older Man/Younger Woman, Daddy Kink, Dom/Sub


"Please, daddy," whined Bonnie. "Just the tip… pleeeeeease… "

James Possible knew that line well. Hell, he used it himself a few times in his younger days. He knew damn well that 'just the tip' never really meant 'just the tip.'

So why couldn't he resist playing along?

James knew he shouldn't even be in this situation in the first place. He should have been able to resist the urge to cheat on his wife. He should have been above bringing a barely-legal 18-year-old to his hotel room. He knew better than to get involved with someone in his own daughter's circle of influence.

Yet here he was, kneeling above a nude Bonnie Rockwaller, gazing at her perfectly-sculpted body. Her legs were open just for him. Her smooth, wet pussy was aching to be filled by him. Even though she said that she just wanted to sample his shaft, he knew she hungered for its full length.

James wasn't dumb. He knew she didn't see her as anything more than Kim's father. He was nothing more than a prize that she would happily hold over his daughter. She was only interested in him as a tool to do what she had so often done: make Kim's life a living hell. All he had to do was say a simple 'no' to keep himself from throwing away so much he had worked for in his life.

James wasn't dumb.

But he was weak.

"You want the tip?" he asked.

"Yes , daddy," she replied hungrily.

James nodded. "Then I need to grab a little something from my bag. Spread your legs and close your eyes."

Bonnie nodded and complied. She grabbed her ankles and held her legs as wide open as she could with a flexibility that only cheerleading could give her. She waited impatiently for Kim's dad to slide inside of her tight pussy and turn into putty in her hands.

CRACK

Her thoughts were interrupted by a loud noise and a stinging sensation on the inside of her thigh. She opened her eyes to see James poised above her, but holding a small whip instead of the condom she thought he was fetching.

"Do I have your attention?" commanded James.

Bonnie nodded, too startled to do anything else.

"I know you expected to run the show with your 'daddy' act," he said sternly, "but that's not how this is going down. You've got two options and only two options. One: Daddy is in control. You do what he says and he rewards you. You don't do what daddy says…" James let the crack of the whip in the air finish his sentence.

"Or… we can stop right here and go our separate ways, and we never speak of this night again. Your call."

James was ready for everything to blow up in his face. His idea was that if he dove fully into the idea of a dominant daddy, Bonnie would not be able to control things. She'd either walk away and be quiet, or walk away and tell Kim, and he figured that Kim wouldn't believe her. Either way, he'd be in the clear.

"Yes."

Bonnie's response caught him by surprise. "What was that?"

"I… I said yes." Her response was breathless.

James was shocked, but he quickly reigned in his emotions. He cracked the whip to his side, which elicited a yelp from the young woman. "Yes what?"

"Yes… daddy."

James smiled to himself. He was weak, and he was horny as hell.

But he wasn't dumb.

Chapter 12: Give It All [Bonnie/Junior]

Chapter Text

Sept. 12 - Take It All

Bonnie/Junior

Content Tags: Pegging, Dom/Sub, Ass To Mouth, Prostate Orgasm


Bonnie grabbed the purple rubber phallus hanging between her legs and slapped it across Señor Senior, Jr.'s face. She repeated the move twice more, then tapped it on his lips. He took the hint and accepted the shaft into his mouth.

"Not so big and strong now, are you?" she taunted. He made no reply, his mouth fully focused on working the first three inches of her dildo. "I said, not so big and strong now, are you?" She emphasized her point by sliding most of her rubber cock down his throat. Junior gagged for a few moments but quickly recovered and adjusted to the additional length.

Seeing Junior submit to her once in a while was something Bonnie desperately needed. She loved when her big 'alpha male' took control, but she enjoyed being in charge as well.

She needed balance.

She needed variety too.

Nearly all of her encounters with Junior ended with him pounding her from behind, digging his fingers into her hips, and commanding that she "take it all" as he came inside of her. She needed something fresh, especially if that came in the form of being able to "give it all" instead.

Once she judged the dildo to be sufficiently wet, she pulled its length out of Junior's throat. "Knees, bitch," she demanded, and the massive man complied. He crawled onto his hands and knees, well aware of what was to come. She positioned herself behind her boyfriend and rubbed the tip of the rubber cock against the pucker of his ass. Moments later, she pushed the tip inside. Junior let out a groan, one that only grew louder and lower as more of the toy slid into him.

"Good boy," said Bonnie as she ran her fingers through his hair and took firm hold. She began to awkwardly buck her hips and slide the phallus in and out of him. It took a few moments for Bonnie to thrust as smoothly as she wanted to. Her brain kept telling her to move her hips as if she was the one being penetrated instead of the one doing the penetrating. Eventually she found the rhythm she was looking for, which allowed her to fuck her boyfriend's ass with ease.

Junior was a whimpering mess. He whimpered and mewed with each and every one of his girlfriend's strokes. Part of it was the submission itself; There was something thrilling about someone half his size taking control of him in such an intimate way. But Junior got physical enjoyment out of the encounter as well. Each stroke plunged his depths and brushed against a spot that made him feel so much more pleasure than he thought possible.

If Bonnie wasn't sure about whether or not he was enjoying this, the cum that oozed out of his cock and pooled beneath him made it clear.

Bonnie took just a few more strokes before withdrawing the rubber shaft from him. She reached down between his legs and gathered up a good amount of his seed on two of her fingers. She brought them up to Junior's mouth and he, after taking a moment to fully realize what she was doing, swallowed up her offering. The taste was far from his favorite, but he was eager to please Bonnie however he could.

"Good job," she said as she patted his head. "You did really well." She made an adjustment to the harness that she was wearing and removed the dildo from it. She tossed it aside and spread her legs, revealing a dripping-wet slit beneath a small, nearly-trimmed tuft of hair. She again grabbed his hair and guided him towards her hot core, face-first.

"In fact, I think you deserve a reward…"

Chapter 13: Put It In... Writing [Kim/Shego]

Chapter Text

Sept. 13 - Put It In... Writing

Kim/Shego

Content Tags: Anal Sex, Embarrassment


Shego was bored. This was the fourth diamond shop she had busted into, and the man approaching her was the fifteenth guard who tried to stop her. His attack was the same as the others: a lame yell followed by a slow hook punch to the head. Yawn. A quick dodge and leg sweep meant that another guard was dispatched. Whoop-de-doo.

Princess was the only one who could make it fun.

Alas, she was nowhere to be found. All she had to do was snag the golden-hued diamond and she'd be one step closer to accomplishing Whitney one of Drakken's inane-

"Yellow just isn't your color, Shego."

Finally things could get interesting.

"Took 'ya long enough, Princess," Shego replied icily. She turned around to find the pair of heroes that could finally present somewhat of a challenge. "Lemme guess: your idiot boyfriend forget where his pants were."

Ron's eyes narrowed. "Shego, your words are hurtful." He let out a sigh. "Still, I appreciate that you remember my presence."

"She'll do more than remember it when we take her down," Kim cried before turning towards her rival. "Because it ends tonight."

It was Shego's turn to narrow her eyes. "And how do you think you'll manage that?"

Kim joined in on the eye-narrowing party. "Because you're going to give in to our list of demands… or else."

Shego smirked. "As if you two could make me do anything. Well, maybe throw up when you kiss."

Kim rolled her eyes. She reached her hand back to Ron and made a grabbing motion. Ron took this as his cue to reach into his backpack and pull out the envelope marked 'List of Demands.' Kim snatched the envelope, marched across the room, and presented it to her nemesis.

"This 'otta be good," mumbled the villainess as she grabbed the offering. She opened the envelope and eyed the letter inside. As she read, her eyes grew and grew in astonishment. Then suddenly…

She laughed.

Hard.

Shego clutched her sides and fell to her knees. She struggled to breathe through her unhinged fit of laughter. Tears fell from her eyes as she collapsed onto the floor and rolled around on it. She was completely unable to contain herself.

"'Ya know, a simple 'no' would have done the trick," said Ron.

"Hell no!" gasped Shego. "I'm not gonna-" She exploded into another fit of laughter. She tried to regain her composure, but fell into another tizzy each time.

Kim crossed her arms. "These are serious demands."

"I bet they are!" whimpered the villainess as she wiped tears from her eyes. She was almost back under control. "I mean, I knew you had a thing for me, but I didn't think you wanted me to have a thing for you!" She barely finished her sentence before another fit of laughter overtook her.

Kim furled her brow. "What in the world are you talking about?"

Shego finally collected herself, the held the paper in front of her and cleared her throat. "This coupon entitles the holder (snicker) to one month… of ANAL SEX…"

Shego could get no further before laughter overtook her again. Meanwhile, Kim was hoping to be overtaken by something along the lines of death or an earthquake. She did not want to be on the planet anymore.

Shego gathered herself to continue reading, as much for her own enjoyment as it was to twist the knife in her rival. "Anytime… (guffaw) anywhere… (guffaw) The receiver of anal sex is required to carry lubricant… at all times-" She fell back onto the ground in hysterics before she could finish reading the fine print.

Kim, pale as a ghost, was aghast. She had no idea how her enemy had pulled that off. Either Shego had somehow gotten a hold of her private writings, or…

"Ron," she said flatly, unable to even look at him, "do you have the birthday note I gave you?"

Ron shook himself from his own stupor, as his brain shut down to avoid wondering why his girlfriend was offering up her body to her enemy. "What? Oh, you mean the one you told me not to read until we got home?" He dug through his backpack and found the note that said 'For Ron XOXO.'

"Got it right here."

"I need you to open it and read it. Right now."

Ron shrugged and complied with his girlfriend:s request, not wanting to upset her further. He opened the envelope and began reading the enclosed note aloud. "We demand that you give up all diamonds and other jewels you have stolen. We also demand that-"

Kim snatched the letter from his hand. She marched towards the still-laughing Shego and ripped the note from her hand, then shoved the actual demand letter into her enemy's chest. She then walked back to Ron and, still unable to look him in the eye, slammed the other note into his chest.

Ron eyed the new note and read it to himself. "Oh, that makes much more sense," he said.

Chapter 14: Show [Kim/Ron/Shego]

Chapter Text

Sept. 14 - Show

Kim/Ron/Shego

Content Tags: Public Sex, Dom/Sub, Oral Sex, Cunnilingus, Rimming


"Tell me when we're live, Nerdlinger," Shego commanded into her handheld communication device.

"Thirty seconds," replied Wade. "There's a red light against the wall that says 'On Air.' When it's on, you'll be in every home in the country."

"Good job," she said. "You'll do well in my government." She was about to pocket the device when a thought crossed her mind. "By the way, how old are you?"

"Fourteen," Wade answered.

"In that case, cover your eyes when I tell you to." She shrugged. "Or don't. I'm not your mom." With that she shoved the device into her pocket and strode to the center of the television studio set. She hit her mark and waited for the 'On Air' light to turn on. Once it did, she began her first national address as de facto ruler of the United States.

"Good evening," she began in a tone that was soft for Shego standards. "My name is Shego. You may call me Miss Shego. If you can see this broadcast, that means that you are now under my rule.

"My operation to take control of the United States only began a week ago. In that short amount of time, my private army has captured ninety percent of the country's military personnel, including ninety-seven percent of its leadership. The rest will fall within the next day or two, along with any civilian resistance that wants to try their luck. In fact, speaking of civilian resistance…" Shego hesitated. "If you're under 18, you'll probably want to cover your eyes for this next part. That means you too, Nerdlinger."

The villainess gave her audience a few brief moments before she snapped her fingers. Seconds later she had a pair of well-known heroes by her side, each wearing a smile and nothing else. "You might know these two. This is the world-famous Kim Possible," she said as she pointed to the woman on her left. "And this is…" She pointed to the man on her right.

"My name does not matter, Miss Shego," said Ron.

"Damn right it doesn't," she responded. She turned her attention back towards the camera. "These two saw what I was capable of and decided that it wasn't worth it to fight me anymore. They have pledged their loyalty to me, and if you're smart you'll do the same." A sinister smile crossed her face. "But don't take my word for it. Let me show you how loyal they are."

Shego snapped her fingers again. Kim and Ron turned their bodies so that they faced their new leader, and Shego turned to face Ron. The now -former heroes dropped to their knees. Ron gently opened Shego's pussy lips and darted his tongue out to lap at her core. Meanwhile, Kim spread Shego's ass cheeks apart and shoved her face between them, her tongue dancing around the dark pucker.

The villainess rolled her head back and let out a moan. She enjoyed both physical sensations, but one was far more exciting to her than the other. She reached to her backside, grabbed Kim's hair, and pulled the redhead as deep between her cheeks as she could.

Shego licked her lips before regaining her composure. "As you can see, my greatest enemies have submitted themselves to me and allowed me to do as I please with them. They are smart. Hopefully the rest of you are as well.

"My demands to the President are simple," she continued. "Just name me Queen, give me as much money as I tell you to, and do what I say. Do that and your people will be able to live their lives like normal. Hell, if you're really good, you might be able to do what these guys are doing." Her eyes narrowed. "If you try to stand against me, well… let's just say that I wouldn't advise doing that. Not if you value your-"

Shego paused her address to let out another low moan. She gripped Ron's head and shoved it deeper into her crotch, willing his tongue to prove deeper. She began to buck her hips hard against his face, occasionally shoving her ass backwards to give more depth to Kim's probing tongue. Her body froze and she let out a combination of moan, yell, and sigh as she hit her first of many orgasms. She took a few deep breaths as she rode the high of her pleasure in front of a national audience, then turned her attention back to the camera.

"Mister President, you must make your decision before I get tired of them making me cum, which should be about… two hours or so. Your people have my number. I'll be awaiting your call. Until then… Hail to the Queen."

Chapter 15: Hot Tub [Ron/Ann]

Chapter Text

Sept. 15 - Hot Tub

Ron/Ann 

Content Tags: Older Woman/Younger Man, Open Relationship, Anal Sex, Public Sex, Ass to Mouth


"Fuck me, Ron!" commanded Annie. "Don't hold back!"

If Ron responded, she never heard it. He had her bent over in the Possible family hot tub and he was fucking her ass at full speed. The constant splashing and swooshing of water created by his thrusting drowned out everything else. Even if it hadn't, Ann wouldn't have been able to hear anything over her own pounding heartbeat.

Annie felt alive when she was with Ron. She wasn't Mrs. Possible, mother of three and responsible adult. She wasn't Dr. Possible, prominent member of the Middleton community. She wasn't Ann, the loving wife of a sweetheart of a man who just happened to lose interest in sex. She was Annie, a woman who finally had permission to get her needs fulfilled and was taking full advantage of it.

The lack of a privacy fence meant that if any of her neighbors were home and heard the commotion in the tub, they could see the lewd spectacle. What would they think if they saw the respected and reserved Ann Possible getting her ass plowed in the open? By a man other than her husband? Who happened to be less than half get age? Would she ever be able to live it down?

But that was an Ann Possible problem, not an Annie problem. All that mattered to Annie at the moment was satiating a hunger that she carried for so long.

Annie broke their coupling and made her way to the shallow end of the tub, then bent back over and eagerly took him in her ass again. She bucked her hips hard against Ron, and this time she could hear the slapping of skin on skin as their bodies now met above the surface. The sound encouraged her to buck even harder, far more intensely than she ever had before for anal sex.

She knew that her inexperienced lover couldn't keep up his current pace for much longer, so she wanted to make him explode inside of her. Even with his lack of technique, he had been able to make her cum a few times through enthusiasm and a willingness to learn what she enjoyed. She wanted to make sure that he got as much out of their time together as she did.

When she felt Ron's hands dig into her shoulders and a warmth inside of her, she knew she had done just that.

Annie continued to rock her hips to milk him completely dry. Once she thought she had accomplished that task, she slid off of his cock and turned around to face him. She dropped to her knees, took his dick into her mouth, and bobbed up and down to milk every drop of his essence out of him. His seed tasted heavenly enough to overpower the bitter and acrid presence of her ass and chlorine. She didn't care. Ron's cum was the nectar of the gods, and she was so very very hungry.

Once his partner had her fill, Ron gripped the edge of the hot tub and took a seat to get off of his wobbly legs. Annie sat beside him and gave him a kiss on his cheek. He would give him all the time he needed to recover, but she hoped that he would be up for another round soon. She was, after all, still hungry.

That was an Annie problem.

Chapter 16: Something New [Kim/Ron/Yori]

Chapter Text

Sept. 16 - Something New

Kim/Ron/Yori

Content Tags: MFF Threesome, Cunnilingus, Fellatio, Creampie


For years, Yori dreamed of a gorgeous wedding. She imagined herself dressed in a beautiful white dress, standing side-by-side with her husband, in the middle of a Western-style ceremony, surrounded by family and friends, in a picturesque location at sunset.

Her reality was nothing like her dream. She was wearing nothing. She was lying on her back with her husband between her legs and her wife straddling her face. It was the middle of the night, and the trio were making their bond official - at least, official in their eyes - in a nondescript hotel room with only themselves as witnesses.

For Yori, it was somehow more beautiful than she ever imagined.

The ninja's legs were spread wide open as Ron drove his shaft deep inside of her folds. Thanks to his Mystical Monkey Power, he had already filled four condoms that night and was well on his way to a fifth. At the same time, her tongue was probing the depths of Kim's slit. The redhead bucked her hips and pressed her core hard against Yori's face, which she happily accepted.

This was far from the first night that she was making love with both Ron and Kim. She had kind their already-established relationship a few years ago and the trio quickly found their groove. What started as a fun experiment soon turned into a serious relationship, one which all three wanted to last forever. This night was their own nontraditional way of announcing their forever bond.

Yori did insist on one nod to tradition. She wanted to include four things that would bring their relationship good luck: something old, something new, something borrowed, and something blue. Typically these things would be part of the bride's dress, but the trio opted to utilize the tradition a little differently.

The old was represented in the bracelet around Yori's wrist, which she wore on her first date with the established couple. Monique lent Kim a length of rope, which she and Yori used to keep Ron in place earlier in the evening during a double blowjob. And when he covered Kim's face with his seed, Yori grabbed the redhead's blue leather collar and held her in place while she licked up every drop of Ron's essence.

All that was left was something new.

Yori gently pushed Kim away from her mouth, then reached down to grab Ron's hips and hold them in place for a moment.

"Ron-kun," she said between breaths, "I am ready if you are."

Ron turned to Kim to see if she had any reservations, only to see a smile and a reassuring nod. He turned his attention back towards Yori and withdrew himself fully from her. He reached down and made a couple of movements below Yori's line of sight. When his hands reappeared he held up the condom that he was just wearing and threw it in the direction of the garbage bin.

He reentered Yori slowly. The ninja let out a loud gasp when he split her folds and immediately wrapped her legs around him. The difference in physical sensation was minimal, but emotionally it was significant. Now, both physically and metaphorically, there was nothing between them.

Kim watched in awe as her husband sent her wife into hysterics. The redhead moved from her position and began to roam around her lovers, planning kisses on their necks and whispering lewd encouragement into their ears. Her cheers were unnecessary, as the mere sensation of Ron's uncovered cock being inside of her brought Yori to a hard peak. Another was on its way as Ron was unrelenting in his strokes. His will to please his new wife was only matched by his will to extend his endurance, but the new sensations were doing a number on him as well.

Ron reached his peak, and the new warmth that filled Yori brought her to one of her own. And with that, the trio were forever joined.

Chapter 17: Take Charge [Kim/Ron/Bonnie]

Chapter Text

Sept. 17 - Take Charge

Kim/Ron/Bonnie

Content Tags: Dom/Sub, MFF Threesome, Vaginal Sex, Cunnilingus


"Oooh, right there Ronnie," cooed Bonnie as her lover hit her sweet spot. Ron was taking her from behind and had just shifted his angle of penetration. The change made all the difference. "Just like that."

Ron grimaced, both from the incredible sensation of Bonnie's pussy and from a level of discomfort in his legs. "Bonnie, I'm on my tip toes," he said. "I don't know how long I can keep this up."

Bonnie whipped her head around and stared daggers at Ron. "You'll keep this up as long as I tell you to," she commanded.

Ron gulped, then nodded. He knew failure was not an option. "Yes, Miss Bonnie." He then put his head down and focused everything he had on remaining in his current position.

The harshness in her face soon turned into a self-satisfied grin. "Good boy." She then turned her attention to the third person in her bedroom. "See what happens when you know how to take charge, K ?"

Kim watched on in stunned silence, just as she had from the moment their group project work session turned into… this . The idea of her best friend doing anything with her biggest non-villain enemy was too improbable to even think about, yet here she was, watching it in explicit detail.

"Nothing to say, K?" taunted Bonnie. "Then maybe you need a better look." She reached back and gave Ron a slight push backwards. He let out a small sigh of relief as he was finally able to put his feet fully on the ground again. Meanwhile, Bonnie made her way towards Kim. She stopped about a foot away from the redhead and motioned for Ron to join her. She placed both her hands against a wall and lifted the leg closer to Kim into the air. She called back to Ron, and the blonde stepped forward, grabbed the lifted leg, and once again slid his shaft into her.

"Mmmmmmm." The brunette tossed her hair back and licked her lips before once again looking at Kim. "Ronnie is so good at following commands."

Kim wouldn't have been able to look away from the scene no matter where it was in the room, but being inches away from the action let her see every detail. How much the pink of Bonnie's folds stood out from her tanned and completely-smooth skin. How tight her lips gripped Ron's shaft when he pulled back. How thoroughly she was coating his cock with her juices. The droplets of sweat that formed on her large breasts. It was all so incredibly mesmerizing.

Bonnie saw the expression on Kim's face and knew she had her rival right where she wanted her. "Don't you wish you had someone like that, K?" Her lips curled into a devious smirk. "Or maybe… maybe you wish you were someone like that."

Kim continued to stare intently at their coupling, but she made no motion to suggest that what Bonnie said repelled her. In fact, Kim was starting to lean forward ever-so-slightly, closing the distance between herself and Bonnie's crotch.

"Or maybe… maybe you are someone like that.”

Kim’s lean was much more pronounced now. She was nearly face-to-face with the point where Bonnie's and Ron's bodies intertwined. The smell of sex filled her nostrils. She saw every detail of what her best friend was doing with his cock, and she saw every bit of Bonnie's pink slit stretching and collapsing around him.

This was Bonnie's chance.

"K…" The brunette's voice was authoritative. "Lick."

There was no hesitation. Kim lunged forward and began lashing her tongue against the top of Bonnie's folds. The redhead swirled it around the hood that hid her rival's nub, mixing in the occasional slight lick across her most sensitive button.

Bonnie grabbed a thick handful of red hair and firmly held her new playmate in place. It was more out of habit than necessity. Kim wasn't going anywhere. Bonnie's natural magnetism drew Ron to her and turned him into a serviceable lover, and that same magnetism had its hooks in Kim. She may have played second fiddle to Kim in high school, but college was going to be a much different story.

It really is amazing what can happen when you know how to take charge.

Chapter 18: Movies [Solo Tara; Implied Tara/Ron]

Chapter Text

Sept. 18 - Movies

Solo Tara; implied Tara/Ron

Content Tags: Voyeurism, Cam Girl, Masturbation


 

Username: misterbooyah05

Password: ***************

Ron logged into his FanFavorite account to look for new posts, just as he had every night for the past five months. He saw that she had just posted a new video that evening, just as she had every night for the past five months.

The view count was still at zero for her newest upload. Yesterday's was still at one, as was the day before and the day before that. Older videos had more views, but they were ones that Ron had rewatched one or twice (or, in one case, 38 times). All told, Ron accounted for every single view on the page.

He imagined that his feed looked very different from most of the other users who used the site. He knew some of his friends were users who followed dozens - even hundreds - of amateur porn creators. He even knew that at least one of his inner circle posted his own content for others to see. Ron's feed, however, consisted of posts from only one user: CheerMeOn18.

A.K.A. Tara King.

The ritual began five months ago. Tara had passed out a pack of kids Valentines cards to all of her friends. Ron's card included a handwritten website address and a long numerical code, with "For Your Eyes Only" underneath. When he went to the site and entered the code, he was granted a complimentary lifetime subscription to CheerMeOn18's FanFavorite page.

Each video she uploaded sent his blood from the head above his neck to the head below his belt. Some were simple series of poses, in and out of various clothes. Others featured her playing with herself with fingers or toys. His favorites were when she talked to the camera and told the viewer that she wanted him to cum. She’d show off all the places where she wanted to feel his seed. Ron found himself going back to those videos again and again, timing them so he would finish when her face was on-screen.

Surprisingly, Tara acted no differently towards him when they interacted in real life. She never brought up her FanFavorite videos when they talked, and she treated him just as she had before. Ron largely did the same, although he often fought back thoughts of her begging him to pop his load while they discussed their Biology 102 homework. Ron assumed that she wanted to show off but go no further, and he was fine with that. Having a beautiful woman show off for him and him alone was an incredible feeling. If he pursued anything, he feared that he would make her uncomfortable, and that would mean no more shows.

Looking and not touching was a lot better than not looking and not touching.

Ron wondered what kind of video she had in mind this evening. Once he opened her page, he was a bit shocked to see Tara in… well, regular Tara clothes. Sweatpants and a boxy t-shirt were the order of the day, a far cry from the typical lingerie set or cotton panties that usually greeted him. She was sitting on her bed as she had done many times before, but usually in videos titled “Soaking Wet Panties” or “Riding my Thick 8” Toy.” The fact that this video was a 61-second clip called “Tonight Only! Contest!”, combined with her dress, led Ron to believe that sitting would be all she would do in this video.

He pressed play, and Tara appeared on-screen to confirm his suspicions.

"Hey lovelies. I've had a lot of fun showing off for you so far, but I’m taking a one-night break try something a little different. I’ve thought about it a lot and I really, really want to try making content with some of my followers. Just comment on this video and I’ll pick a few lucky guys at random, but do it quick because I’m picking the winners tomorrow morning. I’ve got three videos in mind so I’m going to pick three winners. Get your entry in and who knows… if you’re close enough, maybe we can start filming tomorrow night. Ciao!”

Ron blinked once, then blinked again. He double-checked Tara’s subscriber count and saw that it still read “1.” He triple-checked the number, then quadruple-checked it. A massive smile crossed Ron’s face as he posted a simple comment: “I’m in!”

He felt good about his chances of winning.

Chapter 19: Orgy [James/Ann/Drakken/Shego/Barkin]

Chapter Text

Sept. 19 - Orgy

James/Ann/Drakken/Shego/Barkin

Content Tags: Orgy, Double Penetration, Anal Sex, Double Blowjob, Cum Swallowing, Facial


Drakken was thoroughly enjoying the evening's festivities, but he had one minor complaint: He just couldn't see everything at once.

On his right were his girlfriend Shego and his rival-turned-friend James Possible. James stood behind the green-skinned woman and held her in the air with his hands under her bent knees. James had his cock inside of her tight ass and helped bounce her up and down his shaft. A pair of Drakken's flowery vines were focused on her as well, with one sliding in and out of her pussy and the other wrapped around her neck.

A nearly-identical scene was playing out Drakken's left, with Ann Possible impaling her ass on Steve Barkin's thick shaft. The teacher was able to bounce Ann at a much faster rate due to his incredible strength and size. Drakken had a tendril focused on pounding her snatch as well, but instead of Ann's neck, his second vine was teasing her rock-hard nipples.

Drakken was having trouble keeping up with the scene. He got lost in the sight of his own girlfriend being double penetrated. Moments later, a moan from the other side would draw his attention and suddenly he saw his old crush get deliciously manhandled. His head snapped back towards Shego when the green-skin woman let out a sharp gasp, but an equally-sharp gasp from Ann drew his focus again.

" Nnnnnnyah , it's too hard to keep track of both of you," Drakken huffed.

James slowed down his thrusting and turned his attention towards his former college mate. "You know, Drew, we could make this easier on you." He tightened his grip on Shego and began to walk towards Drakken, keeping his shaft in her ass the entire time. He stopped just in front of the blue-skinned man and slowly lowered Shego onto her hands and knees. Once Shego found her balance, she leaned forward and took her boyfriend's cock into her mouth while James restarted his efforts. Drakken let out a gasp when he felt the warmth of Shego's mouth surrounding his manhood. He withdrew the vine from around her neck, as well at the one that was aimed at Ann's breasts, but the ones in their snatches remained.

Barkin saw what James had done and made a similar move towards Drakken. Within seconds, Ann was on her knees beside Shego. The redhead began to plant kisses on Drakken's balls. She worked her way back up to the base of his sack, then up his shaft. She met Shego at his tip, and the two ladies both kissed and licked his cockhead. Their lips met and they kissed each other for a few moments, then they kissed each other and the tip of Drakken's cock.

The ladies split their work as best as they could. Ann bobbed her head up and down Drakken's length with practiced ease, while Shego sucked on his balls the way she knew he liked. They would occasionally stop and let out a gasp or moan in appreciation of the men behind them, but they spent as much energy as they could on making Drew cum.

James slowed his efforts slightly, then gave looks at the other men in the room. "Whenever you're ready," he said. Barkin nodded and slowed his own tempo to keep himself from going over the edge. They both turned their attention to Drakken, who kept his composure as well as he could. But the two warm, wet mouths were proving to be too much for the blue-skinned man to handle. His breathing changed in a way that signaled he was at his limit. James and Steve took that as their cue to pull out of their respective playmates and stand on either side of Drakken, stroking themselves as they moved.

Drew let out a loud groan and shot a stream of cum directly into Ann's mouth. Shego quickly pulled away from his balls and moved her head to be cheek-to-cheek with the redhead, mouth open and waiting. The villainess's mouth was blessed with a stream of cum of her own. A few weaker shots splashed across her face as well as Ann's, but a strong shot from James hit her tongue shortly after. Barkin let loose as well, giving her another load from another direction. All three men stroked themselves to make sure they were fully emptied, with every drop landing either in the ladies' mouths or on their faces.

Ann swallowed all of the cum that had pooled in her mouth, and Shego did likewise. The redhead then began gathering up whatever mess was left on Shego's face with her fingers and licking them clean. The raven-haired woman allowed her counterpart to finish her work, then returned the favor by licking Ann's face clean. It wasn't long before the exchange morphed into another make out session between the two women.

The action came to a screeching halt at the sound of a door unlocking. Five panicked sets of eyes fixated on the front door of the Possible living room, and all five grew wide with fear when Kim walked in.

The college freshman had her nose buried in her Kimmunicator as she entered, but she brought her head up to look for something in the living room. Her face turned white as she saw her mother, her father, her former teacher, and her former rivals all completely nude. The sweat on their bodies and the traces of white, wet goo on the faces of her mother and Shego confirmed her worst fears.

Kim took a deep breath and hit a big red button on her device. Her call went through just as she turned around and began to exit her parents' home.

"Wade," she said flatly as she turned back to exit the house, "do you remember when those guys in black suits gave us that memory device? Can you grab it and flash me with it? Please and thank you."

Chapter 20: Few Clothes [Ron/Joss]

Chapter Text

Sept. 20 - Few Clothes

Ron/Joss

Content Tags: Aged-Up Characters, Older Man/Younger Woman, Vaginal Sex, Creampie


Ron had an official reason for heading to the barn: His 'city life' body needed a break from the relentless work required for life at the Lazy C Ranch. As far as Slim and the rest of the Possible family knew, he was just a city slicker who couldn't handle country work all that well. He needed some time in the shade to recover.

Once Ron reached the building and found a dark corner near its rear, his unofficial reason for heading to the barn stepped forward and leapt into his arms.

Joss Possible tried to get her legs around Ron as best as she could. Her sundress was light and flowed freely in the wind, but it got a bit tangled up against Ron's denim overalls. She was still able to hang from the blonde man easily, as her arms were wrapped around his bare neck and her lips were pressed against his. His hands cupped her rear and easily held her aloft.

This wasn't a deep, undying love or anything like that. This was just a bit of summer fun for two people who happened to find each other very attractive. A nice way to make both Joss's final few weeks before college and Ron's three-week visit to Montana fun and memorable for both of them. The only problem was that time alone was hard to find, so they had to find creative ways to maximize what little they had.

For the most part, that meant limiting their clothing to one item each.

Joss couldn't pull off her sundress in case she needed to make a quick getaway, but she could get it out of the way. She reached down and pulled the hem of the dress above her waist. Her legs now free, she was able to wrap them around his waist. Her hot core was just visible underneath the garment, and Ron wasted little time in running a finger up and down its entrance. Joss threw her head back and covered her mouth to stifle her moan.

Ron shifted her weight towards and onto him to free his own hands. He reached down and pulled down the zipper, thankful that he owned one of the rare pairs of overalls that featured one. His hard cock sprang free from its confines and he wasted little time lining it up to its target and plunging into her depths. He felt her lips latch onto his shoulder as she held back a screech of delight.

Joss felt pleasure jolt through her body once Ron began to thrust. Each motion of his hips made her small frame bounce up and down his length. Joss tightened her grip around him and began to propel herself up and down in time with his movements. They quickly found a steady rhythm and worked to maintain it.

There was an odd sort of silence that filled the barn. The sounds of their skin slapping together was muffled by her thin cotton and his thick denim. Neither partner dared make any unnecessary noise, lest they draw unwanted attention. Instead they used kisses and nibbles to keep their mouths occupied and their coupling secret, and it stayed that way for a few minutes. But eventually, Joss's tightness and the intensity of her movements were too much for Ron to handle.

"I'm getting close," he whispered into her ear.

"You best not pull out this time," Joss whispered back. "I want every bit of it inside."

Ron didn't need telling twice. The extra motivation of knowing Joss wanted to be filled was enough to send him to the point of no return. He tightened his grip on her hips and held her in place as he held himself as deeply inside of her as he could. He let out a muffled grunt as he began to spill his seed inside of her. Joss smashed her lips into his to mute the sounds of her own orgasm. She bucked her hips to milk as much of his essence out of him as she could, as well as to ride her own wave of pleasure to its conclusion.

The entire moment felt risky, which added to their excitement. They risked getting caught by one of their respective family members, even though they were all likely on the other side of the ranch. They risked having their connection discovered by family, even though her not-so-secret crush on Ron had been a bit of a running joke. They risked the effects of having him cum inside of her, even though a copper wire inside of her would prevent anything from taking hold.

But the moment had to come to an end eventually. Ron gently lowered Joss to the ground as she untangled her legs from behind him. Ron stepped back and zipped up his fly, making sure no errant stains were visible. Joss took the opportunity to show Ron how much of his seed was dropping out of her slit and down her thigh. She readjusted her sundress and straightened it out over her to look just as she did before, aside from a few errant strands of hair.

Ron looked at Joss and sighed. "I, uh… better get back."

"Reckon you should," she replied.

He gave her a slight nod and made his way towards the barn's exit.

"Hey Ron!"

The blonde turned his head back towards Joss and saw that she had a smirk on her face.

"Twelve-thirty a.m. Right back here." Her smirk grew even larger. " No clothes this time."

Ron's expression matched his partner's as he tipped an imaginary cowboy hat. "Yes, ma'am."

Chapter 21: Balcony Scene [Kim/Shego]

Chapter Text

Sept. 21 - Balcony Scene

Kim/Shego

Content Tags: Older Woman/Younger Woman, Dom/Sub, Bondage, Cunnilingus, Public Sex


"Say it, Princess!"

Kim Possible refused to give her captor the satisfaction of admitting defeat. Yes, Shego had stripped her naked and held her captive on an open roof. Yes, her wrists were cuffed to a railing on the top floor balcony of Go City's tallest building. Yes, her ankles were cuffed to a pair of metal rings on the floor. Yes, she was positioned above a motorized piston with a dildo attached to it, and it was fucking her pussy relentlessly. But she was not defeated.

"What's the matter?" taunted Shego. "Cat got your tongue? Or should I say, toy got your kitty?" She turned a knob on her handheld remote and smirked as the piston's speed increased.

Kim threw her head forward to get her hair to cover her face. She wanted to hide the look of pleasure on her face from her captor. The machine was hitting all of the right places and easily brought her to the precipice of orgasm. Only her desire to fight against Shego kept her from succumbing to the sensation.

Shego approached Kim and stood behind her. The heroine could feel the villainess's hot breath on her neck, as well as her firm breasts pressed against her back. "You can stop this at any time, Princess," she said firmly. "All you have to do is admit that I beat you."

"Nnnn- noooooo…" Kim denied Shego a victory, but there was too much energy pulsing through her core for the redhead to fire off one of her traditional one-liners.

Shego shrugged. "Your call." She brought her fingers to the device in her hand and cranked the dial to its highest setting.

This time Kim did yelp. A loud one at that. Loud enough to be heard by half of Go City. She limited herself to one, but her body wanted to let out more. It wanted release. Needed release.

The dildo felt like it was splitting her in two, but in the most delectable way. Its base brushed against her clit and stimulated her in ways she had never before experienced. That alone would bring her to orgasm in her own bed. But in this setting? Where she was completely at Shego's mercy? Where anyone in the city with a decent pair of binoculars could see her? It made the thought of giving in all the more appealing.

But the fighter in her wouldn't allow it. She needed to hold strong. Needed to keep holding on. Even if just for a little while longer…

A sharp chirping noise interrupted Kim's thoughts. She turned her attention to Shego, the apparent source of the sound. The villainess eyed the pocket of her jumpsuit and fished a device out of it with her free hand. She brought its screen to life with the tap of her finger, read the notification, and frowned.

"Shit," she said in frustration as she shoved her phone back into her pocket. "You went fifteen minutes without cumming. Looks like you win, Kim." She twisted the knob on the handheld remote from its highest setting to its lowest, and the piston quickly came to a stop. Kim bit her lip to keep from revealing any sort of unintended reaction, as the dildo felt damn good while it was running. But her first priority was handling her would-be captor.

"Looks like I win, who ?" Kim said sternly.

Shego rolled her eyes in bemused frustration. Her girlfriend was not going to let her off the hook so easily. She sighed and allowed her features to soften. "Looks like you win, Mistress ."

Kim nodded. "That's more like it. Now…" The redhead cast an eye towards her shackles. "Free me." Shego advanced and unlatched the cuffs that bound Kim's wrists to the railing. The ones that held her ankles were also dispatched.

The moment Kim's ankles were freed, the redhead wrapped her legs tightly around Shego's head and pulled her face tight to her core. The former villainess's nostrils were instantly filled with the hot scent of sex, and she could feel the heat radiating out of her girlfriend.

"Lick."

Shego's ears may have been partially covered by Kim's thighs, but she heard her girlfriend's command loud and clear. She teasingly grazed her tongue over Kim's bright pink nub, and that was all it took to send the young woman into rapture. Kim finally allowed herself to cum, and the dam that held back her pleasure completely crumbled. She let out a guttural groan at the top of her lungs, then several more that were only marginally quieter. She bucked her hips against Shego's face to ride out one of the biggest orgasms she ever experienced.

Shego worked her head free from Kim's legs and gave her girlfriend a smirk. "The toy had you in a hair trigger, didn't-"

"Did I tell you to stop licking?"

Shego quickly shook her head no and dove back into Kim's snatch. The interruption startled her for a moment before she remembered how seriously her girlfriend took their competitions.

Kim relaxed once again and enjoyed the feeling of Shego's tongue against her most sensitive of places, but something shiny caught her eye. She saw that the cuffs that had held her against the balcony railing were still in position.

Perhaps it was time for Shego to get a taste of her own medicine.

Chapter 22: Office Sex [Ron/Ann]

Chapter Text

Sept. 22 - Office Sex

Ron/Ann

Content Tags: Older Woman/Younger Man, Cheating, Vaginal Sex, Creampie


Ann's arm flew across her desk. Stacks of paper flew into the air and various knickknacks tumbled to the ground. She was turning her office into a disaster area, but she couldn't care less. All that mattered was grabbing hold of the desk's edge and steadying herself so that she could fully enjoy the pounding she was about to receive.

Her right hand found the far corner of the table and gripped it tightly. The fingers of her left hand wrapped around the desk's front edge. She pressed her chest against the table's surface and braced herself.

Ron moved into position behind Ann. Without a word, he flipped the hem of her lab coat over her back, then did the same with the skirt she wore underneath. He grabbed her panties and pushed them to one side to expose her molten hot core. He unbuckled his belt and pulled his pants and boxers down just below his genitals in one smooth motion. He gripped his dick by its base and rubbed its tip up and down her slit to make sure he was well-lubricated, then plunged forward to fill her completely in a single thrust.

Ann gasped and dug her fingers into her desk. She tossed her hair back, and was only moderately surprised when Ron grabbed her tresses as he established his rhythm. He pounded her at a torrid pace from the get-go, with each of his thrusts touching her in places that yearned to be touched for years.

This was what she had craved. Missed. Needed. For so very, very long.

Three years since her husband last touched her. Two years and three months since he promised that he'd work on his issues. Two years and two months since he gave up on said work. Three months since she could no longer pretend that she could live that way.

Six weeks since Ron turned eighteen. Two weeks since she decided to play along with his obvious crush on her. One week since she realized that it wasn't a one-sided interest. One hour since she sent him a nude selfie from behind her work desk captioned 'come get it.'

Ron's thrusts were wild and deep and powerful. They lacked the grace that a more experienced lover would possess, but that suited Ann all the better. She needed to be fucked, and Ron was doing it so very well.

The rest of it didn't matter. Not the mess that she'd have to clean up later. Not the noise that could surely be heard through the rest of the executive level of the Middleton Medical Center. Not the fact that her co-workers would have questions later about what she was doing with her daughter's friend. Not the fact that she hadn't even bothered to ask Ron to use protection.

All that mattered in the moment was the delectable friction that Ron's cock was creating inside of her and the feeling of being fucking desired for once.

Ann might have been able to cum if she played with herself, or if he could somehow keep this up for a while. She knew that wasn't going to happen, not at the pace Ron had set. Frankly, she was surprised that he had lasted as long as he had already. She could hear him straining his groans and feel him slowing his speed, and she knew what that meant.

"Don't pull out," she said without giving it much thought. Before she could reconsider, Ron pushed himself as deep as he could inside of her and began to fill her with his hot seed. She rocked her hips slightly to make sure he was fully spent before he pulled out.

She felt him withdraw from her and she suddenly felt so empty. The sensation of cum dripping out of her core and down her leg only made the emptiness more complete. She had dealt with going without for so long that it shouldn't have been an issue, but she missed his warmth instantaneously.

"That… that was…" Ron was still trying to catch his breath and make sure that he wasn't dreaming.

"Do you have anything else going on today, Ron?" She was too focused on her own thoughts to let him finish his sentence.

"Uh… not really," he replied unsteadily.

"Good," she said. "Do you want to go again?"

The young man's eyes bulged in shock. "You want to? With me?" He gulped. "I mean, of course I would, I just… I know I didn't… you know, last long, so I thought you'd-"

"Good." She reached over to her office phone - the only thing on the desk she hadn't managed to knock over - and hit a speaker button.

"Mindy, clear my afternoon. Something came up."

Chapter 23: Creative Procreation [Kim/Ron/Yori]

Chapter Text

Sept. 23 - Creative Procreation

Kim/Ron/Yori

Content Tags: Handjob, Threesome, Vaginal Sex, Cunnilingus


Kim found herself in one of her favorite places in the world, yet it felt so much stranger and more foreign than it had ever felt before.

Kim stood behind Ron in the bedroom of their apartment. They were both naked, and her arms were around his waist. Her breasts were pressed into his back while her hands gripped and pumped his shaft.

Jerking off her boyfriend was something that normally felt very comfortable for Kim, but there were two things that were contributing to the strange feeling that hung over the evening. Issue Number One: Ron was not hard. He usually responded eagerly to her touch, but it seemed that something was dampening his excitement.

Kim let out a sigh of defeat and leaned the side of her head into Ron's back. "This is awk-weird, isn't it?"

Ron shrugged. "I mean, a little ." He turned his attention towards the floor in front of him. "How about for you?"

Specifically, he turned his attention towards Issue Number Two: Yori.

The ninja was on her back, wearing a look of contemplation on her face and nothing on the rest of her body. She had lifted her legs above her head, effectively folding herself in half. Her hands were spreading her lower lips apart, providing Ron with a target for his essence.

"This is a bit odd," Yori admitted. "I thought that the suggestion was one of your American-style jokes at first. But if this is what is required of me…"

"It is," Kim insisted, although her features instantly softened after her outburst. "I mean, it's not. I mean…" She let out a frustrated huff and let go of her boyfriend's member to run a hand over her face. "I feel like this would go better if you weren't laying like that."

"Of course," said Yori. The ninja lowered her legs and bounded to her feet to be face-to-face with Kim.

The redhead let out a frustrated sigh. "Look, I know this is really strange. This wasn't my idea."

"Ummm… Kim?" Ron's interjection was a timid one. "This actually was your idea, remember? You wanted Yori to hold her legs open so I could cum in her and get her pregnant without me actually having sex with-"

"I know that was my idea," said a frustrated Kim. "I meant… all of this wasn't my idea. I didn't want the fate of the world to depend on my boyfriend knocking up a really hot ninja and fathering some magical savior. It's just…" She sighed again. "I know it sounds kind of silly under the circumstances, but I wanted to keep Ron to myself, you know?"

Yori nodded and placed a hand on the redhead's shoulder. "I understand. I have no intention of taking Ron-kun from you. I am simply here to fulfill my duty and return home."

Ron stepped forward. "Wait, wait, wait… Return home? I kinda thought that you'd want my help with… Not saying that you'd need my help, but-"

"Relax," said Yori. "You need not worry about any of that. Not for now, at least."

"That's not what Master Sensei told me," Ron countered. "He said that I need to create Yamanouchi's great hero inside of you, and that it will be my honor to guide him on the path to his destiny."

Yori took a deep breath and let out a heavy sigh. "Sensei's interpretation of the prophecy is… off."

"How… off … are we talking?" asked Kim.

The ninja took another deep breath. "Sensei is concerned about The Chosen One drifting away from the school, and that colors his interpretation of the prophecy. Ron-kun is destined to father Yamanouchi's hero. That is for certain. But he is destined to do so in his own time, with the love of his life."

"And that's… not you, right?" asked Kim, unable to hide the urgency in her voice.

Yori shook her head. "I know what you two mean to each other. I am fond of both of you, and I have no desire to occupy a place in someone's heart meant for another."

"I'm still confused," said Ron. "If you don't want to get pregnant, why are you here trying to get pregnant?"

Yori moved towards the pile of her discarded clothes in the corner of the room. She fished through her pockets until she found a packet of pills and tossed it towards Kim. "I can assure you that I'm not trying to get pregnant," she said. "My hope was that Sensei would realize the error of his interpretation when Ron's seed failed to take hold in me."

Kim looked up from the half-empty packet. "You could have just not had sex and told Sensei that you did. Why did you ask to sleep with Ron?"

Yori bowed her head and began to blush. "Like I said, I am fond of both of you."

Ron furled his brow in confusion. "Well why did you agree to Kim getting naked and doing all the fun stuff?"

Yori's cheeks turned redder. "Like I said, I am fond of both of you ."

Kim and Ron looked at each other questioningly.

"It's kinda funny," said Ron. "We've been through so many weird things in our lives, and yet this is almost the weirdest."

"I know," Kim responded. "It's almost like a plot of one of those late night cable shows."

"Not quite." Ron turned towards Yori, who was still too embarrassed to look at the couple. "If it was one of those shows, all three of us would be having sex with each other in about five minutes."

 


Five minutes and fifteen seconds later


 

Ron stood near the edge of the bed with Yori bent over in front of him. He has a firm grip on the ninja's hips as he thrust into her with everything he had. He sent shockwaves of pleasure through his partner's body with every motion, and the sensation of her tight pussy on his cock more than returned the favor.

Kim was getting her fill of pleasure as well. She was on her back on the bed with Yori's face between her legs. She held a fistful of black hair to keep the ninja's tongue in constant contact with her hot core and throbbing clit.

"KP," said Ron, "how did this even happen?"

Kim raised a finger to her lips. "Don't think about it. Just accept it and enjoy it."

Ron shrugged his shoulders and did just that.

Chapter 24: Lust at First Sight [Ron/Ann]

Chapter Text

Sept. 24 - Lust at First Sight

Ron/Ann

Content Tags: Older Woman/Younger Man, Altered Mind, Rimming


"He doesn't have to come in, does he?"

Ann Possible chuckled at her daughter's odd request. "We've had a lot of practice with tele-health over the last couple of years," she said, "but I think I need to physically see what's going on."

The younger woman sighed. "I knew you'd say that."

"Then why did you ask?" Ann chuckled again. "Besides, why would you have me come all the way out to your school if you didn't think I would see him?"

Kim slapped her forehead and dragged her hand down her face. She took one last look around the girls' locker room to ensure that nobody else was around.  "Alright," she relented, "but I've gotta warn you… he's not acting like himself."

The heroine stood up and approached one of the big closed lockers. She twisted its combination lock back and forth to unlock it and swung the door open. She reached into the locker and pulled out a blindfolded Ron. Kim guided her boyfriend to the bench and sat him down across from her mother.

Ann gave Ron a visual once-over and found no obvious difference. No apparent injuries, no cuts or bruises, and no changes in appearance. She reached towards him and pulled off his blindfold and was greeted with the same brown eyes she always saw.

Then those eyes flashed red for the briefest of moments.

The flash faded as quickly as it appeared, but it changed something in Ron's eyes. They were focused on Ann in a way that she had never seen from him before. He was leering at her the way some of her colleagues would when they thought she wasn't looking. He wore a lecherous grin as he eyed her body up and down.

"Damn," he said, "I might be half the age of Mr. Dr. P, but I can fuck you twice as good as he can."

Ann was taken aback, but quickly collected herself. She had seen her daughter and boyfriend go through significant physical and mental changes during missions, and her experience told her that this would be the same.

Kim sighed. "He got hit with the Lust-At-First-Sight-ulator. It's supposed to help couples reignite their lost spark, but Loverboy can't stop trying to spark nearly every woman he sees."

Ann nodded, relieved that her hunch was correct. "I can see how that would be a problem. And I'm guessing that you can't just give him another shot to get him back to normal."

Ron grabbed Ann by the wrist and stared deeply into her eyes. "Or… I can give you another shot… then another… and another…"

Kim rolled her eyes as she swatted her boyfriend's hand off of her mother. "Wade's working on reversing the polarity, but it might take a while. He said that we may have to wait until this… thing … burns itself out."

"Trust me," said Ron, "my thing never burns out."

"I'm tempted to grab a lighter and put that to the test," Kim grumbled before turning back towards her mom. "I hope you've got an idea, otherwise he's gonna be a pain in my ass for days."

"I can have my tongue in your ass for days," replied Ron as he gave Ann a lecherous wink.

The doctor blushed slightly, as Ron's comment caught her by surprise. She cleared her throat and refocused on her daughter. "Well, I can take Ron in to the office. I can check his blood flow, run some blood work, and see if anything jumps out at me. In the meantime…" She took a contemplative breath. "I can run him through an exercise program and see if him spending energy cools him off."

Kim gave her mom a weary smile. "Better than nothing, I guess." She walked over and gave her a hug before turning towards Ron. "No more funny business, understand? I've already got to explain the situation to Tara." She sighed. "And Hope. And Bonnie. And the lunch lady…" Her voice trailed off as she left the locker room.

Ann spied the entrance in the moments after her daughter's departure to make sure that she was gone. Her gaze then settled on Ron, who was still looking at her with a hunger that she hadn't felt in a long time. She closed her eyes and took a breath to either steady herself or allow the idea in her head a chance to fade away. When she reopened her eyes, she knew what she was doing to do.

"So you think you could eat my ass for days, huh?"

Ron smirked. "I don't think. I know ."

The older woman took off her white lab coat and snaked her thumbs under the waistband of her skirt. "I guess I've gotta keep you occupied somehow." She chuckled. "You know, I've been begging James for years to try it. You think you're really up to the task?"

"Absolutely," said Ron as he moved behind his girlfriend's mother and tried to make good on his word.

Chapter 25: Picnic [Kim/Tara]

Notes:

(See the end of the chapter for notes.)

Chapter Text

Sept. 25 - Picnic

Kim/Tara

Content Tags: Public Sex, Oral Sex/Cunnilingus, Fingering, Food Play


In the back of her mind, Kim knew that this wouldn't be a typical picnic.

Had her outdoor lunch with Tara taken place in a public park, then maybe things would have remained in the realm of the PG rating. But in the secluded patch of grass on the side of Mount Middleton, their date was destined to be an X-rated affair.

Tara was spread out in front of her on their soft picnic blanket. The blonde was completely naked, save for white lines of whipped topping drawn onto her body via Kim's fingers. Dollops of the sweet treat appeared on her nipples, only for Kim to make them disappear with her mouth.

Kim gathered more cream with her fingers and drew a line from one of Tara's nipples down to her taught stomach, then down further to her clean-shaven folds. The redhead's tongue then took the same journey, dawdling at both its origin and its destination.

"So good," moaned Kim as she lapped at her lover's folds. Her tongue slid up and down Tara's lower lips, letting her juices mix with the taste of the whipped topping. Kim savored the sweet flavor of her lover, which was made all the sweeter by the dessert.

Kim snaked her tongue around the blonde's pink nub, which elicited a loud gasp and moan. It was music to the redhead's ears, and she slid two fingers inside two create more of that wonderful harmony. She had already drawn a masterpiece on her beautiful canvas. Now her focus was orchestrating a beautiful symphony.

The music followed shortly thereafter. Kim relished the feeling of Tara tightening around her fingers as she rode the first of many orgasms. The blonde was someone who peaked early and often, and Kim thoroughly enjoyed seeing how many times she could cum. Her first cries of pleasure rang out into the sky and through the mountain range. Her second soon followed, as did her third, fourth, fifth…

Tara eventually pushed her girlfriend away to give herself a break. Kim would have gone all day if given the chance, and Tara was half-tempted to allow it to happen, but she had her own hunger to satisfy. She kissed Kim and gently pushed her onto her back. She then reached into the picnic basket and pulled out a jar of honey.

Tara wanted to paint a masterpiece of her own…




Notes:

Life happens. I can't promise that there won't be more delays between chapters going forward. All I can say is I'm aiming for shorter gaps between these final few stories.

As for why there was a delay... It turns out that caring for a colicky newborn is not conductive to bring in the mindset to write erotica. Who knew?

Chapter 26: Up High [Ron/Shego]

Notes:

(See the end of the chapter for notes.)

Chapter Text

Sept. 26 - Up High

Ron/Shego

Content Tags: Bondage, Tit Fucking, Oral Sex, Anal Sex, Ass to Mouth, Pussy to Mouth


Any other man would have been dead by now.

Shego was not one to stand being tied up. Yet here she was, dangling ten feet above the floor of her blue-skinned partner's lair. She was bound at the wrists by a pair of shackles which hung from the roof of the cavernous building. Another pair were wrapped around her ankles and bolted to the concrete floor.

While she was held in place, her partner flew freely around her. Zorpox - the villain formerly known as Ron Stoppable - was using a pair of rocket boots to great effect. He buzzed from one part of her body to another, taking whatever pleasure he wanted from her. He pumped his cock in and out of her snatch one moment, and the next he pushed her breasts together and thrusted into her cleavage.

"Grrr." Shego struggled to hide her annoyance. "Can you slow down a bit? This ain't the Olympics so you don't have to set any wor-BLRRRRG! "

Zorpox rammed the entirety of his cock into Shego's mouth. He gripped the back of her head and held her in place as he began to pump his shaft in and out at full force. Instinctively she tried to push him away, but the resistance she felt in her wrists reminded her that she was held in place.

In the blink of an eye, Zorpox was out of her mouth. Shego gasped and began to breathe heavily now that she no longer had a thick cock blocking her airways. Those gasps turned into a shriek when she felt something warm and slick sliding between her lower lips and into her core. She looked down to see Zorpox floating on his back between her legs, his boots angled down to keep him afloat. The spit on his dick from the blowjob moments earlier had helped him slide in quickly, but her core was already plenty slick by her own juices.

"Delectable," cried the villain. He held himself at full depth for a moment to savor the feeling of his cock being fully surrounded by his subordinate's pussy. He enjoyed the moment in peace as Shego had yet to respond verbally, and he knew the quiet wouldn't last long. He decided to break the silence by beginning to thrust in and out of her. The rhythmic sound of his skin slapping against hers quickly filled the cavernous lab.

Shego stifled a moan. Being at the mercy of her boss felt surprisingly good, especially when it led to him filling her so deliciously. But she had no interest in admitting it to him… at least, not out loud. She hoped that her not instantly using her plasma to blast through the chains - or through him - was enough of a clue.

Without warning Zorpox withdrew himself from Shego's cunt. Before the move fully registered, Shego heard the whoosh of her boss's movement and felt something hard slip between her lips and into her mouth. Once again the villain had shoved his cock into her mouth and had started to fuck her face. The taste of his cock was tinged with her own familiar flavor, and she had no choice but to swallow it down.

Another whoosh gave her mouth relief and turned the focus of the action back to her pussy. Zorpox slid into her core once again without hesitation. Whatever juices Shego had swallowed off of his shaft were quickly replaced.

Another blink of an eye and he had positioned himself behind her. He gripped her ass cheeks, spread them apart, and pushed the tip of his cock against her pucker. She let out a loud gasp as he pushed through the initial resistance and slowly slid his length into her ass. He took a few tentative thrusts, pushing himself a bit deeper with each one.

As quickly as he had entered her ass, he exited. He was back at her pussy, instantly pounding away at her. But as soon as he got into a rhythm, he moved back to her ass. This time he was able to push more of himself into her rear, and his thrusts grew a bit faster.

The rhythmic thrusts came to an abrupt halt. She barely noticed the break before her mouth was once again filled with Zorpox's shaft. This time the taste of her ass overwhelmed his cock and whatever pussy juices remained on it. Her comet powers and her body's ability to burn anything harmful to her immune system meant that she wasn't in danger of getting sick from the act, but it was still a bit jarring to her senses.

Once again, his efforts quickly shifted. His shaft left her mouth and he flew around to get backside. He slid his cock into her ass, and this time he was able to push the entirety of his length into her. He gripped her hair and began to thrust at full speed. Only now did Shego let out a moan. A big one, in fact, then another and another.

The sensation stopped again. In another flash Zorpox flew in front of her. He hovered slightly onto his back and positioned himself somewhat under his captive in somewhat of a cowgirl position. He aimed the tip of his cock at her slit and began to thrust, much to the delight of the villainess.

"Move again and I'll kill you as soon as I'm free," she muttered between moans.

"You couldn't kill me if you tried," he taunted as he pounded her. "Besides, I doubt you want to right now."

Shego tried to stifle another moan but failed. She knew he was right on both counts. She was truly at his mercy, and she… didn't entirely hate it.

She just wished that Zorpox would stay put long enough to let her cum.

Notes:

Have you ever wondered if it's difficult to find time to write erotica while you have to take care of an infant? If you have, I can assure you that it is VERY difficult.

Chapter 27: 7 Minutes in Heaven [Kim/Ron]

Chapter Text

Sept. 27 - 7 Minutes in Heaven

Kim/Ron

Content Tags: Blowjob, Established Relationship, Public Sex


Kim practically shoved her boyfriend into the closet and followed him inside, slamming the door shut behind her. Ron stumbled a bit but quickly found his balance against a plethora of hanging garments. Kim had no such struggles as she quickly made her way to Ron's side. She found a hanging cord above her head and yanked it to turn on the enclosure's ceiling light.

"You've got seven minutes to knit," Bonnie teased from the other side of the door. "Or whatever it is you two do with each other."

Ron shook his head. "I don't think I'll ever understand why she's on us all the time," he said. "I mean, how did we even let her talk us into playing Seven Minutes in Heaven? You serve as her Homecoming king one time and she thinks that she gets to-"

His train of thought came to a screening halt when he felt a pair of hands on his belt. He looked down and found Kim on her knees in front of him, scrambling to undo his belt buckle. She was able to unfasten the halfiversary gift she gave him and pull down both his pants and boxers in one fell swoop.

"Ummm… what are you doing?"

Kim looked up, semi-hard dick in her hand, and smirked. "Exactly what it looks like." Her face quickly grew serious. "As long as you want to, of course."

"Well, yeah " he quickly replied. "I'm never going to say no to that. It's just… with this game and… and Bonnie and…" He gulped. "You're not doing this to play Bonnie, are you?"

Kim shook her head. "Look, Bonnie is annoying. Like really, really…" She sighed. "Really annoying. And yeah, she gets to me sometimes. But she's never going to get to me enough to make me do anything that I don't want to do. And there's nothing in this universe that would make me do anything with you that you don't want to do."

"So you doing this isn't for Bonnie," said Ron, halfway between asking and confirming.

"No," she replied assertively. "This isn't for her. This is for me." She emphasized her point by taking Ron's entire cock into her mouth.

Ron moaned at the sudden sensation. The moan turned into a groan when he felt her pull back slightly to let her tongue swirl around his hardening cock. It was a move he loved, but it was typically something he only got to experience after plenty of foreplay.

"Straight to the big guns, huh?"

Instead of a verbal answer, Kim tapped the watch on her wrist to remind him of their limited time in the closet. She then brought her head back further so that only his tip remained in her mouth. She cracked a slight smile around his shaft before she jerked her head forward and took his full length down her throat.

Ron shuddered. He immediately grabbed Kim by the top of her head, but nowhere near firmly enough to control her movement. She began to bob her head up and down the length of his shaft at a torrid pace. 

"Keep this up and I won't last very long," he hissed through gritted teeth, although he was sure that Kim was already aware. He never lasted more than a minute or two when she pulled out this move. Then again, she usually saved it for the end of their sessions when she wanted to get Ron over the proverbial finish line. He didn't know how long he could handle being deepthroated from a cold start.

From the feeling building in his core, the answer was 'not much longer.'

Kim's efforts were unrelenting. Every bob of her head sent another jolt of pleasure through Ron's body. Her lips effortlessly worked his full length with practiced ease, and her tongue brushed against the underside of his tip in just the way he loved.

It was all too much for Ron to handle. He gave his girlfriend a tap on her shoulder to let her know what was about to happen. Kim released his cock from her mouth and quickly grabbed it with her hand. She pumped his shaft while aiming his tip at her open mouth.

Her efforts were soon rewarded. Ron bit his lip to stifle a groan and keep those outside of the closet in the dark, but there was no hiding his pleasure from Kim. The first spurt of cum hit her tongue. A second, third, and fourth quickly followed, most of which landed in her open mouth. Kim allowed her boyfriend's essence to pool on her tongue until she was satisfied that she had extracted every drop. She closed her mouth and happily gulped down her gift.

"Ron," she said as she caught her breath, "that was for me."

"I don't know how I got so lucky," he replied breathlessly as he tucked his cock back into his pants and refastened his belt. He froze in his tracks when he caught sight of something on his girlfriend's lips. "Uhhh, KP? You've still got a little-"

"Don't worry about it." Kim quickly assured him.

"Kim, it's not makeup," he stressed.

"I know," she said nonchalantly.

Ron was nearly panicking. "Everyone's about to see-"

"-your cum on my face. I know." Before her boyfriend could object further, Kim opened the closet door and locked eyes with Bonnie.

The brunette stood in front of the rest of the onlookers, poised to taunt Kim for not doing anything in the closet. Her face froze in shock when she saw Kim's frazzled hair, and her eyes bulged when she noticed the splash of white near Kim's lips.

Kim couldn't help but smile. The smile grew even larger when she gathered up her boyfriend's essence with her finger and brought it to her mouth. The lewd act caused Bonnie to stamp her foot and turn away in a huff.

Kim turned towards Ron and pointed in her rival's direction. "That was for her," she said.

Chapter 28: Afterglow [Kim/Ron]

Chapter Text

Sept. 28 - Afterglow

Kim/Ron

Content Tags: Cuddling, Domestic Fluff, Creampies, Vaginal Sex


"I don't wanna move."

Kim's sleepy comment wasn't an answer to a question. It wasn't a response to someone or something calling for her, either. Rather, it was an unprompted bit of early-morning self-realization.

"I don't want you to move," mumbled a barely-awake Ron. His arm, which was gently draped around the waist of the nude woman on top of him, tightened its hold on her and pulled her closer to his own naked body. This was their first night together as roommates, and he was in no hurry to see the night end.

Kim melted into her boyfriend's hug and nuzzled her cheek against her chest before letting out a sigh. "I probably should move, though."

Ron gave his girlfriend a playful look. "How come?"

Kim shot a questioning glance back at him. "Did you lose your sense of… everything?"

Ron matched her expression. "...No?"

The redhead gently shook her head. "I'm sweaty."

The blonde shrugged. "Well, yeah. You did have a pretty big workout last night."

"Ha, ha," Kim replied dryly. "Just for that, I'm gonna stay here."

Ron smirked. "How exactly is that a punishment, KP?"

"It means that you have to deal with my sweat getting all over you."

"Already dealt with it last night, Kim," he replied as his smirk grew larger. "And it's not like you haven't been getting stuff all over me already."

Kim's eyes bulged in shock when she felt a pair of Ron's fingers brush the length of her lower lips. He then rubbed those same fingers against one of her ass cheeks, leaving behind a small trail of the last of the evidence of their early-morning lovemaking session.

"Oh, now I definitely need a shower." She pushed against her boyfriend's chest to lift herself off of him. As her body lifted from his form, she felt his stiff member brush against her. The sensation froze her in her tracks and sent a shiver down her spine. Once she recovered, she gazed down at Ron's face, and any desire to leave the bed disappeared.

Kim reached back and grabbed his cock, pushing it to her core's entrance. She slowly slid down his length, eliciting groans from both herself and her man. Once she was fully impaled, she leaned forward to allow her lips to meet his. They kissed hungrily and passionately.

Then they stopped.

Kim pulled away with a sour look on her face, one that Ron mirrored. They both had the same thing on their minds, and they verbalized their thoughts at the same time:

"Ugh, morning breath."

Kim pulled herself off of Ron's cock and plopped down onto the mattress in frustration. Ron let out a frustrated sigh before turning to his girlfriend, instinctively holding a hand over his mouth.

"I'm guessing you want to shower first?"

"Please and thank you."

Chapter 29: Swallow It [Ron/Bonnie]

Chapter Text

Sept. 29 - Swallow It

Ron/Bonnie; implied Kim/Ron

Content Tags: Oral Sex, Facefucking, Cheating, Cuckquean


"Knees."

Ron's command was firm. There was no anger or fury in his voice, nor was there pleading or begging. It was simply a dispassionate statement; Bonnie was going to drop to her knees.

And drop she did.

"Mouth open."

The brunette did as she was told. The instant she opened her mouth she found it full of Ron's stiff cock. Bonnie assumed that she would have to take his full length down her throat, and it wasn't exactly something she was unfamiliar with, so his sudden move did not surprise her. Still, it took her a moment to adjust to the sudden presence of a dick in her mouth.

Luckily for her, Ron wasn't completely naive about what a person could and could not handle. He allowed her a few moments to catch her breath and get herself comfortably positioned. Once she was settled, he began to thrust in and out of her mouth, quickly reaching his top speed.

Bonnie was a bit annoyed. She preferred to be in control in most situations, including sex. She usually led the way with her partners and she had expected meek and meager Ron to be no different. As uncool and un-suave as he had asked her to his dorm to study while Kim was out of town, she expected him to bend to her will the moment she gave him the time of day.

Things weren't going as expected in that regard, but that was no problem. She could handle Ron thinking he was in control for tonight. All she needed was a few more minutes and a single incriminating picture. Then she'd be able to claim complete and total victory over her long-time rival and be the undisputed queen of Go City University.

A few minutes of being Ron's playtoy were well worth the reward.

"Keep sucking."

Ron's voice was more strained and his thrusts were more frantic. She knew he wouldn't last much longer. In all honesty, she was surprised he lasted as long as he did. One of his hands held her head in place as he continued to pump his shaft in and out of her mouth.

Then he paused on his backstroke, the tip of his cock on the tip of her tongue. He let out a primal groan and began to spill his seed into her mouth. Bonnie let Ron's essence pool on her tongue as more and more of his seed splashed into her mouth. Her hand worked to milk the rest of his cum out of him as he struggled to catch his breath. He then looked down and gave her another firm command.

"Swallow it."

Bonnie held up one finger, wordlessly asking Ron for a moment. She quickly grabbed her phone from a nearby table and opened its camera app. She then positioned herself next to Ron, her face resting on his hip with his still-hard dick dangling in front of her. Before Ron could react, she angled the phone to ensure that both of their faces were clearly visible, and opened her mouth to show off Ron's seed.

"Send me a copy," said Ron nonchalantly.

Bonnie blinked. She didn't expect Ron to be so calm about her getting photographic evidence of his infidelity. But ultimately she didn't care. She quickly snapped the picture. After double-checking that everything was clearly visible, she sent the picture to Ron's number then saved the image to her cloud storage. With her job done, Bonnie gladly gulped down the salty cum.

Victory never tasted so sweet.


The buzz of her phone's vibration pulled Kim Possible from the final throes of her sleep. She opened her eyes and adjusted to the bright sunlight in her Mumbai hotel room. The notification on her screen came into focus, confirming that she had a new message.

From Bonnie Rockwaller.

Kim's fingers went into overdrive as she entered the device's password to unlock her phone. She expanded the message and was greeted with the jaw-dropping sight of her boyfriend, naked, in their shared dorm, with Bonnie beside him.

A buzz announced the arrival of another message, also from Bonnie. It was a simple text consisting of two words:

"I win."

Seconds later, a message from Ron arrived. Kim opened it only to find the same picture as she had received from Bonnie just seconds earlier. Beneath the image was a bit of text:

"Does this work for you KP?"

She thought she would like being adventurous. She thought that she would like the sight of her boyfriend with another woman. She thought that she would like the fact that he was getting pleasure, even if she was half a world away, and she was thankful that Ron was willing to step out of his comfort zone for her sake.

But all of those thoughts were simply that - ideas. Now that Ron being with another woman was reality, Kim quickly found out that she did not like those ideas.

She loved those ideas.

Without a second thought, she threw her bed covers. She used one hand to open her phone’s camera app. The other made its way between her legs and came to rest on her pussy, which was quickly becoming wet..

She wanted Ron to see exactly how much she appreciated him trying something new for her.

Chapter 30: Free Day [Multiple pairings]

Chapter Text

Sept. 30 - Free Day

Content Tags: Open Relationships, Cunnilingus, Anal Sex, Ass To Mouth, Rimming, Bondage, Walk of Shame, Age Difference

Pairings: Surprise

For those who wish to be spoiled, pairings and some additional content tags related to the pairings are listed at the end of the chapter 


Kim Possible woke up to a heavenly feeling between her legs.

She felt a pair of soft hands on the insides of her thighs, and she felt those hands inch their way closer and closer to her pussy. She felt hot breath against her already-wet slit and she could tell that a tongue was inches away from her core. She opened her eyes and saw a patch of blonde hair between her legs.

"Mmmmm, I thought guests got to eat first in this house," cooed Kim.

Tara looked up from Kim's crotch and smiled. "Usually that's the case," she said, "but this morning I'm very… very… hungry."

With that Tara closed the gap between her upper lips and Kim's lower ones. The redhead let out a sharp gasp followed by a long sigh. Kim grabbed a fistful of hair and pulled Tara in as close as humanly possible, enjoying a wake-up call that could only happen once a year.

It was just twelve months ago that the anniversary of defending the planet from the Lowardians was declared Free Day by nearly every nation's government. How its meaning had shifted - within a year - from celebrating freedom, to celebrating freedom and love, to celebrating free love, was beyond Kim.

The feeling of Tara's tongue circling her clit made Kim eternally grateful for the shift.

The redhead let out a moan and threw her arms back to the bed. She attempted to grasp the bed sheet but instead found her Kimmunicator. The presence of the device suddenly reminded Kim of something she had to do.

"Mmmmm-Tara," she hissed through a moan, "can you stop for a sec? I need to do something."

The blonde girl gave Kim one last lick before pulling her head away. "Don't take too long," she said. "I'm still hungry."

"On it." Kim picked up the Kimmunicator and rattled off one of the fastest text messages she had ever composed.

 

KIM: Wanna meet up at the park @ noon?

 


Even in the familiar surroundings of his own room, Ron barely heard the buzz of his phone's message tone. He was so focused on his thrusting and controlling his body that nearly everything else faded into the background. He needed to make this last, and his partner was making that so very difficult.

Ann Possible's ass had that effect on him.

The mere sight of his cock sliding in and out of Ann's ass as she was bent over in front of him was enough to send him into overdrive on its own. Couple that with the sounds that the older woman made as she rubbed herself in time with Ron's thrusts and he was in paradise already.

But the feeling… how her rear entrance felt so tight, squeezing his member in all the right ways… That was enough to make him blow his wad instantly.

Ron had lasted quite some time already, but he could go no longer. He gripped Ann's hips tight, thrust himself fully into her one last time, and let out a howl as he unloaded his seed into her rear. Ann upped the speed of her own rubbing just long enough to bring herself to her own peak. She felt Ron collapse onto her back and quickly allowed herself to fall onto the bed as well, with her young lover's weight deliciously pressed against her. She savored the feeling for a few moments before bringing the rest of the world back into her mind's focus.

"I think your phone went off," said Ann, still recovering from her orgasm.

"Huh?" Ron shook his head to bring himself down from his high. "Oh yeah. Guess it did." He reached down to the part of the bed where his phone was while keeping his cock inside of his older lover. He saw the message from Kim and smiled. He quickly typed up a response to his girlfriend, then turned his attention back to his girlfriend's mother. "You need to text James? Er, I mean, Mister Doctor P?"

Ann chuckled at Ron's stumble. "Not a bad idea," she admitted. She slowly slid off of Ron's dick, allowing the cum he had filled her with to begin to drip out. She reached over to her own phone and scooped it up, then spun her body around to face Ron. She lowered her head, gripped the base of his shaft with her free hand, and began licking the tip of his cock.

Ron let out a hiss of pleasure before looking down at Ann. "I thought you needed to use your phone."

"I can multitask," she said before taking nearly all of Ron's cock into her mouth. As she began bobbing up and down his length, she glanced towards her phone and typed out a message to her husband.

 

ANN: 🏠 at noon or so. Brainloaf 🆗 for dinner?

 


James Possible already had his phone in hand when he got a message from his wife. He quickly flicked his thumb a couple of times to send off the suggested reply of "Yes" before returning his attention to the newest article on Sci-Fi Films Daily's website. As he stood in his bedroom, he caught up on the hot rumor of the day. Allegedly, the lead for the new Captain Constellation film was on the verge of quitting the film. Apparently the actor had yet another clash with the director, and this one was a doozy.

James broke his attention away from the article to look at the young woman on her knees behind him. "Faster," he said.

Bonnie Rockwaller looked up at James and nodded. "Yes Sir," she replied before letting her tongue return to James's ass. She used one hand to spread his cheeks as far apart as she could, then ran her tongue around his pucker as quickly as she could. Her other hand was snaked around the older man's waist as she pumped his cock.

Bonnie was not used to being subservient, but she got a crash course on the matter over the past 20-ish hours. James was firm and demanding and he made sure that she did exactly what she was told. He dished out punishments if she did not follow his commands, as evidenced by the handprints on her ass cheeks. But he also made sure that she was rewarded well for doing what she was told to do, as evidenced by the cum that was dripping out of her pussy and down her thigh.

James caught a glance at the time. He grabbed Bonnie's hand and pulled it off of his cock, then turned back to his younger playmate. "You should probably message your boyfriend."

Bonnie pulled her head away from James's rear and took a big gasp of air. "Yes, Sir," she replied before grabbing her phone from nearby. She began to type up a message when she felt a hand on her head.

"I didn't say to stop."

Bonnie found her face pulled into the older man's ass. She quickly darted out her tongue to return to her assigned task. As she did, she slowly typed out a message to Junior.

 

BONNIE: Tonight you're serving me. Understood?

 



Drakken snapped his head around when he heard a tone that sounded like a phone, but was not his own. He quickly realized that the buzz was that of his partner's device. Drakken shot a vine towards the nearby table and snatched up the phone, then offered it to his playmate. "It's for you."

"Can you answer?" asked Señor Senior, Jr. "I'm a little… tied up right now."

Drakken blushed in embarrassment. Junior was pinned against the wall of the doctor's lab. Four of Drakken's vines had shot from his neck and took hold of the young playboy, with one appendage wrapped around each limb. The end of a fifth vine was wrapped around Junior's cock and milking every drop of cum the man could produce. It had brought the bronzed man to orgasm five times in the past couple of hours and was poised to add to the total once the phone issue was taken care of.

"Oh. Right." Drakken turned on the phone and saw the message on top of the notification bar. "From Bonnie," he said. "Tonight you're serving me. Understood?"

"Tell her… I shall serve her as she wishes."

"As… you… wish," muttered Drakken as he typed out the last of Junior's dictation.

"Oooh, add some kissy faces."

Drakken rolled his eyes, but complied. "Kissy face, kissy face." 

"One more."

The doctor let out a huff. "Third kissy face," he said as he tapped the screen. "Sent." He stared at the screen for a moment in silence before turning towards Junior. "I should send one too," he said.

"Go ahead," SSJ encouraged.

The flowery scientist returned Junior's phone to the table before grabbing his own. He used a few extra tendrils to write a message and send it off in near-record time before returning his attention - and his efforts - to Junior.

 

DREW: Reconnect at 13:00? Your place or mine?

 


Shego grabbed her phone, saw the message, and let out a sigh. "It's the same place, Drew," she thought to herself. She quickly rattled off a message saying as much, then returned her efforts to getting dressed.

"Leavin' so soon, babe?"

Shego stopped in her tracks and shuddered as her hopes of leaving unnoticed went up in smoke. "Yeah…" She let out a sigh. "You know how it is. Early bird gets the worm and all that."

Motor Ed patted the empty space next to him on his bed. "You don't gotta go anywhere, babe. You can get the worm right here."

Another, heavier sigh. "Yes. Yes I do gotta go somewhere."

"Babe, when I said worm, I meant my-"

"I KNOW what you meant," she cried. "Still gotta go."

"Aww, don't be like that," pleaded the mulleted man. "We had so much fun last night. Your green magic, my… " He glanced between his legs. 'Mister Magic… All I wanna do is keep the party going!"

Shego shook her head. "Correction: YOU had so much fun last night. I was underwhelmed the whole time."

Ed laughed. "Killer joke," he said. "But c'mon, seriously, how good was I? Like, if you had to rate it on a scale from nine to ten, how was I?"

"NINE TO -" Shego choked back anger. "I gave you a shot last night and what did you do? You creamed your jeans twice, blew another wad when I touched your underwear, and when you finally did get around to actually fucking me, to would've had to last twice as long as you did before I could call you a two-pump chump. And you think that's a NINE?!?!? "

Ed bowed his head in shame. He took a moment before tilting his head back towards Shego. "Eight-and-a-half?"

Shego let loose a scream and a plasma shot, both of which were aimed at Ed. The gearhead rolled out of the way just in time. He eyed the mattress and saw a smoldering billow of smoke where his genitals were just moments ago.

"I'm out!" cried Shego as she turned on her heels and headed for the door. She pulled out her phone and furiously thumbed through her contacts before settling on a familiar name. She mashed out a message and sent it in hopes of somehow salvaging something from this Free Day.

 

SHEGO: Hey Princess, room for one more?





Pairings: Kim/Tara, Ron/Ann, James/Bonnie, Drakken/Junior, Shego/Motor Ed

Additional Content Tags: Older Woman/Younger Man, Older Man/Younger Woman, Older Man/Younger Man

 

...and with that, I have now written more than 100,000 words of Kim Possible smut. I'm not entirely sure what that says about me, and I'm not entirely sure that I want to know what that says about me.