From One Sister to Another Ch. 01

DISCLAIMER: Nothing in this story is real or should be considered as such. This story is very odd and is based on a strange fantasy I concocted that brings together some fetishes I'm into. This first chapter introduces the characters, sets up a little bit of where the story will be going, and yes, features hardcore sex between consenting adults. I do know where the story is going to be headed and have the future chapters mapped out in my head. However, I welcome any feedback and I'm always excited to discuss the story and characters, and chatting/bouncing around ideas for future stories. I hope you enjoy delving into my insane mind.

NOTE: This story features characters that appear in my other stories. They do not take place in the same continuity. Each series can be considered its own universe of sorts, with difference events, relationships, and couplings.

FROM ONE SISTER TO ANOTHER CHAPTER 1

Maddie should have just kept walking. She never should have peeked into the opening of her sister's bedroom door. Curiosity killed the cat, after all, and right now, sitting on the floor outside of Tiffany's bedroom, back braced against the wall, Maddie herself might have still been alive, but her entire worldview was buried six feet under and never coming back. That murderous curiosity had driven her to look, and because of it, she learned three important things that ended her, that effectively killed the Maddie that existed before that moment.

The first, was what her sister's naked body looked like. Sure she'd seen her sister naked before but that was many years ago, back before they fully developed into the women they were now, and certainly never, ever like this. Never while she rode on top of a guy, rocking her hips back and forth while crying out in pleasure.

Their entire life, Maddie was always the more attractive sister. She took pride in her wide hips, shapely thighs, and thick dark blonde hair that ran down to her mid-back. Not to mention her undeniably cute face with vibrant honey-colored eyes, plump lips, and an awkwardly shaped but alluring nose. Even after she finally filled out, a good handful of years after Maddie, her younger sister just never quite hit the level she did. And that's not to say that Tiffany didn't have her own appeal. It was just different. She was long and lanky, her individual parts not as exaggerated as Maddie's. But right then, in that moment of nakedness, her proportions seemed exactly right.

Her breasts, much smaller than Maddie's own, looked perfectly suited to her frame as they bounced up and down on her chest, their perkiness indisputable. Her legs, with its gap right between her thighs where they met her mound, seemed exactly contoured for straddling the man beneath her. And her small ass appeared thick and plump as it gyrated back and forth.

While Maddie was undeniably the more attractive sister, there was no question how goddamn sinfully hot Tiffany looked fucking someone.

The second thing Maddie learned was what her boyfriend looked like fucking someone, in this case, Maddie's very own sister. Because it was definitely Kyle that was underneath Tiffany's rocking body, teeth clenched, strands of dark hair plastered to his forehead while he gripped Tiffany's jerking hips. He was naked as well, somewhat new to her also, though she'd seen enough bits and pieces separately to have formed a picture. She'd seen him shirtless before, from the back as he changed underwear, and on only a handful of occasions she'd seen his erect penis. Ironically, that last bit was the one part of him she couldn't see at the moment. But she'd never seen him have sex before and certainly never with someone else.

In the entire time they'd been dating, coming up on four months in about two weeks, Maddie and Kyle had only ever really gotten as far as handjobs. And getting to that point took about three weeks in itself. Kyle never pressured her to do anything and the first time she ever reached for his pants to unzip him and slink her hand inside to grab his stiff prick, it was entirely her own choice. That first time had been a little awkward; she was a bit unsure, but Kyle's groans and eventual climax were nothing if not encouraging. Since then, she'd jerked him off a few times, gaining more confidence with every stroke and every moaning explosion from her boyfriend. But even after all that, she had to admit, it was mostly for Kyle's benefit over hers.

Yes, Maddie was attractive. Yes, she was aware of how hot her body was. But she also was just not that interested in having sex. Maybe it was her inherent shyness, a level of modesty and traditionality that blocked her from finding immense pleasure in the idea of spreading her legs for someone. She knew she'd eventually do it for Kyle, but she had put off progressing past handjobs because of her unusual lack of interest. Kyle had never complained about it, never tried to force her face closer to his cock the times she beat him off while on her knees, but maybe now she knew why.

Which led to the third and final thing Maddie learned. The most world-shattering revelation: how insanely, panty wettingly fucking hot she found it all. How much it turned her on watching her sister fuck her boyfriend. That was truly the thing that put an end to the Maddie that existed prior to peeking into that doorway. The Maddie that watched for nearly a minute, taking in the sight of her sister and boyfriend's wild coupling before catching herself and spinning to brace against the wall lest they see her, was someone else entirely. The Maddie that quietly slid down to a seated position while listening to the sounds of the bed creaking and whose breath caught in her throat as she pushed her hand into her tights to find a slick, wet pussy waiting for her, was a brand-new Maddie. And as she rubbed her hand down between her slick lips and stifled a cry of joy, she knew the old one was gone forever.

"Uggnhh! Are you... close?" she heard Tiffany pant from inside the room. Maddie had covered her mouth with one hand while the other frigged herself harder, thick thighs spread to accommodate the erratic movements inside her tights. She'd been masturbating outside Tiffany's door for almost five minutes by this point, reveling in the moans, groans, and dirty talk between the two. "We gotta... finish... before she... gets home. Mmmmm!"

If only they knew that Maddie had been home for some time now, a mere twelve feet away listening in and getting off.

Her class had ended early and rather than stay on campus any longer she decided to head back home. Her eyes had nearly popped out of her head when she entered the condo she shared with her sister to hear the unmistakable sounds coming from upstairs. Maddie had never had sex herself, but she knew what it sounded like, and even though Tiffany wasn't seeing anybody, it was very obvious her sister was having some. As much as she felt bad thinking it, it wasn't that surprising to Maddie that Tiffany might hook up with a guy she just met. She could see Tiffany trying to use sex to compensate for the lack of attention she received compared to Maddie. And from the sound of it, unlike Maddie, Tiffany seemed to enjoy it, so she wasn't going to judge her sister that much.

Not wanting to ruin Tiffany's fun—and embarrass the both of them—she had snuck upstairs intending to head straight to her room. But as she approached Tiffany's doorway, she saw it wasn't closed all the way, with about a foot of space between the door and the frame. She could have just walked right past it and continue to her room but instead, Maddie had paused and with a curious smirk, had peeked inside to catch a reflection of the action in Tiffany's large dresser mirror.

"Yeah, I'm close," Kyle grunted in response to Tiffany's question. "I can't believe we're actually doing this. Ungh! Fuck! It's so wrong."

"Cause it should be my sister?" Tiffany said, the sound of her bucking picking up. "You probably wish it was her. She's... so hot. Hotter... than me. And so fucking proud of it."

It was true. Maddie was very prideful of her looks... and secretly took just the slightest bit of pleasure in that fact when comparing herself to her sister. She thought she hid this dark truth well but apparently not well enough. Part of her felt bad about that and the complex it must have created for her sister, but that part was buried under the sea of an orgasm desperately wanting to crash onto the shore.

"Right now... you look fucking hot."

"Ooohhhhh." The sound of the creaking bed was near constant now, barely a breath between each bounce. "Hotter than her?"

"Fuck yes," Kyle gasped. "Shit, I'm almost there."

"Me, too," Tiffany said at the same moment Maddie thought the same thing. Maddie desperately wanted to hear them cum, knowing it would push her over the edge. But then a thought suddenly struck her. If they finished, and she was still here... Maddie's clenched eyes flew open.

"Shit," she hissed. She forcefully yanked her hand out of her tights. Quietly and quickly as she could, she scrambled down the stairs and toward the front door, carefully opening it and sneaking back out. Though, truth be told, the volume of the "ah ah ahs" of Tiffany's fucking would have drowned out any noise she made.

Once safely outside, Maddie released the breath she was holding with a long sigh. She had successfully made it out. However, now she faced another problem: her lustful pussy was aching for release. The sudden stop of her approaching climax left her frustrated and flustered. But where could she go? Licking her lips, she walked to the community garage, trying to appear casual while still moving at an accelerated pace. By the time she got to her car, she was nearly running. She darted her eyes around the area to make sure no one was around, then swiftly entered and dropped the seat down into a prone position.

With a satisfied whine, Maddie returned her fingers to inside her sopping wet panties. Teeth clamping down on her bottom lip, she rubbed herself at a feverish pace. Her mind filled with the images and sounds she witnessed moments ago. Tiffany's hands on Kyle's abdomen, her hips pumping and grinding; her head down, dark short-cropped hair hanging in front of her face. The muscles in Kyle's thighs flexing as he met Tiffany's rhythm, his eyes locked on her body. The creaking of the bed springs working to support their animalistic mating. Their grunts and groans.

In her head she kept repeating the same phrase over and over again: her sister was fucking her boyfriend, her sister was fucking her boyfriend, her sister was fucking her boyfriend... and they looked so fucking hot together.

"Oh shit, oh fuck," Maddie panted and whispered. "Ungh ungh ungh... Oooohhhhhh YES! AHH!"

Maddie's body stiffened, hips off the seat and in the air, eyes rolling back into her head. Her orgasm slammed into her, paralyzing her completely as the electrical shocks ran through every fiber of her being. She vibrated and shook almost imperceivably before finally crashing back down, chest rising and sinking, breaths coming in labored gasps. God, she was glad she wore black tights today.

Fifteen minutes later, a re-put-together Maddie loudly opened the front door to their condo.

"Hey," she called out, eyeing up the stairs toward her sister's bedroom. "I'm home."

"In here," came a reply from the kitchen. At the same time, Kyle appeared from the opposite direction, coming out from the downstairs bathroom.

"Hey," he said, strolling over to give her a hug and a kiss on the cheek. "Sorry to surprise you. I came over a little early."

"Oh!" Maddie caught herself, faking surprise at her boyfriend being there despite already knowing that fact. "I wish you had texted. I could have hurried back sooner."

"It's okay. Tiffany and I hung out."

He said it so casually, so easily, like they were just sitting around playing video games or something while waiting for her to get home. Surprisingly, Maddie wasn't offended by the lie or angry about it. Instead, it again made her stomach do cartwheels.

"That's good." Maddie looked over to see Tiffany emerge from the kitchen area. Her body was now covered by a loose summer dress. She could see her sister's hip bones against the thin material and Maddie wondered if she was wearing panties underneath. "It's so nice to see you two together... hanging out."

"Your boyfriend is alright company," Tiffany said with a smirk. Maddie noticed Kyle smiling awkwardly out of the corner of her eyes. "I just started making dinner."

"Oh, great!" Maddie said excitedly, grabbing Kyle's hand and pulling him toward the kitchen. "We can help."

For the rest of the night, Maddie tried to see if she noticed anything between Tiffany and Kyle, something she may have maybe missed before. Furtive glances, hands brushing against each other, whispered secrets. She kept expecting them to do the type of things usually reserved for couples, things she and Kyle would sometimes do. While prepping dinner, she'd turn around and anticipate seeing Tiffany at the cutting board chopping carrots with Kyle pressed up against her, his hands on her waist, his crotch nestled between her flimsily covered butt cheeks. When they sat down to watch TV after dinner, she pictured them settling into the loveseat while she took the single-seater sofa. Even when they retired to their respective rooms later that evening, she envisioned Kyle breaking off from her as they passed by Tiffany's room to join her inside.

Naturally, none of that actually happened, but the thought of it all drove Maddie wild. With every odd fantasy that entered her mind, she felt her heartrate quicken and her panties moisten. She had no idea why these imagined scenarios between her sister and boyfriend had this effect on her, but by the time her and Kyle entered their room and shut the door, she was a ball of sexual energy.

"Tiffany looked nice today," Maddie said while they lounged in bed for a moment, both on their phones. However, Maddie was having trouble concentrating on the screen. "That dress looked really good on her. Don't you think?"

"Uh, yeah," Kyle said, still paying attention to his phone and appearing disinterested. "She looked pretty good. It was a cute dress."

"You should tell her."

That caught his attention. He placed his phone facedown onto his chest and stared at her curiously.

"What now?"

"If you think she looks cute, you should say something."

"You want me to... hit on your sister?"

"Not hit on her. I don't know." Maddie got up and headed toward her dresser. "I think it'd be nice. Sometimes I feel like she's insecure, you know, and you complimenting her or putting some effort into hanging out with her more like today, I think it'd be nice is all."

As she began pulling out her sleepwear, she heard Kyle get off the bed and make his way over.

"Sure. I can do that, yeah. I'll... tell your sister she's hot." Kyle chuckled, thinking he was making a joke. Instead, Maddie's mind went back to earlier, to Kyle telling Tiffany how "fucking hot" she looked. Hotter than her.

"Great. Thanks," Maddie said, giving a sarcastic tilt to her voice to mask her growing arousal. She started undressing, pulling off her top and tights, unhooking her bra, when she stopped. Because of her general shyness, her and Kyle usually faced away from each other when they changed, but standing there in just her panties, she turned around to find Kyle in his boxers opening his overnight drawer to pull out some pajama pants. Maddie sauntered over to him, surprising both of them when she slinked her arms around his waist and slipped her hand into his boxers to grab hold of his cock, giving the slab of meat a slow jerk.

"Whoa," Kyle said in a shocked gasp, straightening up and leaning his naked back into her topless form. He closed his eyes and allowed her to increase her pace on his dick. She beat him off rapidly, her fist popping at the fabric of his boxers, the area growing and shrinking from her moving fist. It took her boyfriend a moment to realize her bare tits were pressing into his skin.

"Hang on," he hissed, pulling her hand out from his underwear before turning around to gawk at her naked breasts, which he'd only seen a handful of times before and only in the dark. Maddie bit her lip and stepped back, giving him a good look at her. She wondered if he was comparing them to Tiffany's. Maddie's were bigger, with more heft and just the slightest bit of sag. Her nipples were darker than her sister's as well, closer to a tan brown over Tiffany's light pink. Kyle reached out toward her boobs, ready to squeeze and fondle the mounds of flesh. "Damn. You are so—"

"Another time," Maddie interrupted, grabbing his arms, spinning him around, and pushing him toward the bed. He collided with the edge of the mattress and plopped down just as Maddie fell to her knees and yanked off his boxers, freeing his now fully erect penis. She grabbed back onto it, the turgid member already slick with precum, and resumed her fast pumping. Kyle groaned and shifted his hips forward while bracing his arms back, trying to give Maddie full access to every inch of his dick. The fapping of her fist drove him wild. He opened his eyes to look down at her staring at his member as if entranced, her cute, sexy face so close to its glistening tip, before he shut them again.

As Kyle basked in the ecstasy of his girlfriend's pistoning hand, Maddie wadded into the waters of her own pleasure. Again, she found herself unable to find arousal in her own sexual act. Instead, her mind wandered to the bizarre fantasies from when they were prepping dinner and watching TV. Kyle grinding against Tiffany's ass in the kitchen. Tiffany and Kyle making out on the couch. Kyle reaching under her sister's cute dress. She switched to an exaggerated version of the events she observed earlier. Tiffany and Kyle now fucking like wild animals, their grunts and groans turning into screams and ravenous cries of desire, their bodies bouncing and thrusting savagely. She licked her lips as Kyle dropped backward onto the mattress, hands covering his face, stifling his moans.

"Was that their first time," she wondered, her jerking hand mimicking the pace of their fucking in her mind. She thought it might have been. It sounded like maybe it was. "What else had they done? Had she done this to him? Had she done more?" Maddie panted, her quick, hot breaths right on the head of Kyle's cock. "She had," Maddie decided. She already imagined her sister was the type to put out after just meeting a guy, but maybe she didn't do it too often. The other guys, she took care of in other ways. "Yeah, Tiffany's definitely sucked a lot of cock," Maddie thought, her face inching closer. "...including my fucking boyfriend's."

Maddie dipped her head down with a wanton whimper, submerging the first two or so inches of Kyle's cock into her warm, wet mouth. She savored in the feeling of it for a moment before lifting her head up and sinking down again.

"Holy shit," Kyle gasped, jerking up from the bed to watch wide-eyed as his girlfriend went down on him for the first time. She gripped him with her hand, concentrating her sucking on the portion of his cock extending up past the ring of her index finger and thumb. Her thick hair draping across his thighs. Her awkward nose scrunching just the slightest bit. Her lips encircling his shaft, sliding up and down. He collapsed back, twisting the sheets in his hands. "Oh my god. Mmmm that feels so fucking good."

Maddie bobbed her face up and down, Kyle's groans and dirty talk spurring her on. His hips began to pop off the bed as he tried to fuck himself into her mouth. She was inexperienced and didn't want to take him too deep but clearly, he was enjoying it.

"I wonder if he's thinking about her," Maddie thought, her dipping head picking up speed. "I wonder if he's imagining Tiffany's mouth around him right now." An image popped into her head of Kyle cumming as she blew him: him reaching out to grab her head, holding her in place as he erupted, and calling out her sister's name.