The Other Sister Ch. 02

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A walk on the dark side leads to firsts.
6.9k words
4.38
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Part 2 of the 2 part series

Updated 06/10/2023
Created 10/26/2020
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DISCLAIMER: Nothing in this story is real or should be considered as such. This story is a little unusual and is based on a fantasy I concocted that brings together some fetishes I'm into, and yes, features sexual acts between consenting adults. 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 different events, relationships, and couplings.

THE OTHER SISTER CHAPTER 2

"Can I get your advice on something?"

Tiffany lowered her phone and turned to face her sister. For the past hour or so, the two had been mindlessly staring at their screens. Or rather Tiffany had been. Maddie, on the other hand, as Tiffany had noticed whenever she glanced her older sibling's way, had spent most of the time staring off into the distance, something clearly on her mind. Apparently, she had finally decided to get whatever was on there off of it.

"Of course," she said. "Dress sexier. Always good advice."

"Ha. Ha," Maddie deadpanned with a roll of her honey eyes. "It's about a guy."

Tiffany had assumed as much. Over the past few months, she had become Maddie's confidant whenever it came to the subject, and advice had basically turned into code between them for guy talk. However, it had been some time since her older sister had come to her for "advice," and the prospect of Maddie at long last needing some got Tiffany extremely excited — in more ways than one.

Her sister hadn't gone on a date in several weeks, which for Maddie was an unusually long time. Guys tended to ask her out on a near weekly basis but ever since her breakup with Emmet — a bear of a guy with a disappointingly small dick — no one else had apparently made a move. Which meant, in that time, Tiffany had been just as untouched as her pure, virginal sister. Figuratively speaking. Tiffany had touched herself many times in the intervening period, but instead of fingering herself to all-new twistedly perverted encounters between her and Maddie's boyfriends, it was to the memory of previous ones.

Sure, she enjoyed every moment of lustfully pumping her wet hole while reminiscing about stroking Maddie's boyfriends' cocks until they exploded rivers of hot, sticky cum all over her sister's stuff, but a girl could only hit replay so many times before the song got old. If Maddie was coming to her for advice, it meant that it could be time to queue up something new and Tiffany's panties grew damp at the thought.

"If it's about a guy," Tiffany said and pretended to turn back to her phone, "dress sluttier then, not sexier."

"I'm serious!"

"Okay, okay," Tiffany relented. In truth, she was also serious about wanting her sister to dress sluttier, secretly finding the idea of the sweet, innocent Maddie showing off her body in an attempt to do the type of dirty and debaucherous things that she did immensely appealing. However, for the sake of the matter at hand — and to avoid delving too deeply into her own psyche on why exactly she felt that way — she played the comment off like a joke. "What's up?"

"Jamal Bryson asked me out."

Tiffany's jaw dropped. Of all the things Maddie could have needed advice on, that was one she did not expect.

A member of the school's track and field team, Jamal Bryson was well known on campus. He wasn't a college celebrity by any means, but when you said the name, most people knew who you were talking about. He was tall, fit, and carried himself in a way that parted seas of people. Above all though, he was fucking hot. The possibility of her sister dating the attractive athlete, and of she herself getting a crack at him, nearly made Tiffany slip her hand into her pants right then and there to relieve her suddenly pulsing pussy. Instead, she simply said, "Holy shit. When are you guys going out?"

"Well, I haven't accepted yet," Maddie admitted, darting her eyes away and missing her younger sister's furious glare. "That's what I wanted your advice on. I'm not sure."

"Why the hell not?" Tiffany couldn't believe Maddie would pass up the chance at someone of Jamal's status. She would kill for someone like him to notice someone like her, and here was her sister, wondering what to do instead of immediately throwing herself at the handsome runner. Not to mention that Maddie's hesitation might end up costing Tiffany the only shot she'd ever get with him as well. "Is it cause he's black?"

"God, no!" Maddie exclaimed. "Nothing like that."

Tiffany was relieved by her sister's obvious and immediate horror over the suggestion of her being prejudice. Not that Maddie ever exhibited those types of thoughts and feelings. But they did grow up in a rather small, conservative town, and while she and Maddie might not have taken issue with dating someone like Jamal, the rest of their town would have and absolutely judged them for it. However, loathe as she was to admit it, Tiffany had to acknowledge that the level of her attraction to Jamal stemmed from its own type of prejudice. The taboo nature of hooking up with a black guy made her even more interested in him and made the thought of his thick, dark cock in her pale, white hand even more arousing. But philosophical debates about prejudice aside, she'd be damned if she let her sister ruin an opportunity like this.

"It's just that..." Maddie continued, drawing Tiffany's attention back to her sister and away from the fantasy of her on her knees stroking Jamal's dick. "He's an athlete and clearly experienced and confident and... I'm just worried he might have expectations for a date that I, um, can't deliver on."

"Good. Don't. Instead, you should wear your skimpiest outfit. Something that really shows off those tits. And when you walk in front of him, sway those wide sexy hips. Maybe even give him a flash of your panties, the green ones for sure. Get him all worked up thinking about you parting those fat lips for him, or even better, spreading those thick thighs. Get him hard and horny. And then bring him back here for me to take care of, since you refuse to just let him pop your cherry with his big dick. This is why your boyfriends like me more, Maddie. Because you 'can't deliver' with that body."

That was what Tiffany's lust-addled brain wanted to say. Her mind filled with a flurry of images, dirty thoughts her dripping snatch wanted and needed to become reality. Part of her even considered telling her sister to just do it, the idea of Maddie giving up her virginity on a first date making her burn with scorching hot desire. However, again Tiffany managed to restrain herself, this time her sisterly instincts kicking in and shoving her dark cravings to the back of her mind.

"Maddie, you don't ever have to do anything you don't want to. If you're interested in him, go on the date, but don't ever 'deliver' because you feel pressured to."

"Thanks, sis." Leaning over, Maddie yanked Tiffany into a hug. It was a surprising moment and it took Tiffany a second to return the gesture. She always thought she and Maddie were close, but it occurred to her that they never really hugged. It was nice. She squeezed her sister back. "I think I will go out with him. He is pretty hot."

"Right?" Tiffany said, her excitement on the rise again. "And remember, you don't have to go down on him unless you want to, no matter how big his dick is."

"Oh my god!"

Maddie shoved her away and they both burst out laughing.

Tiffany stifled her moans as best she could, her breaths coming out in heavy gasps. Her extra horny imagination had gone into overdrive the moment she was alone. As Maddie slept soundly next door, Tiffany's fingers played at her clit and occasionally dipped themselves lower to plunge into her wet hole. She meant what she told her sister earlier, but the fact that her advice also worked in her favor was certainly an added benefit. Her sister had decided to go out with Jamal, and in response, the second she had gotten into bed, she had let her submerged thoughts resurface and her mind went wild with lusty fantasies.

Eyes closed, Tiffany pictured her and Jamal in Maddie's bedroom, so familiar to her at this point that she had no problem envisioning the exact layout, the precise spot they'd be in as she gripped his thick cock in her hands. She imagined she'd need both to hold him, to adequately cover the length of his shaft if the rumors were true. She jerked him vigorously, her fingers in real life matching the pace of her pumps. She wanted to make him cum so bad. He'd asked out her sister, but it was her that was going to get Jamal Bryson to cum.

What if she wore the same outfit Maddie had on the date? A small "ah!" of pleasure escaped her lips at the thought. Still on her knees in front of Jamal, still jacking his dick with both hands, but now Maddie's dress hanging off her smaller build. Where the low neckline would have emphasized her sister's cleavage, it left Tiffany's smaller boobs almost fully exposed. She groaned. Her frantic jerks would cause the dress to slip, shift over to completely bare one of her tits for him. Outside the fantasy, Tiffany's hips rocked and bounced, her ministrations taking her closer to completion. He'd stare down at her, eyes locked on her stiff pink nipple, and say, "Fuck, you look so much sexier like this than your sister." Then... "unngghhh"... he'd cum, pulsing his thick load all over the dress and her tits.

Tiffany bit down onto her hand as she climaxed, nearly breaking skin from the sheer intensity of her walls spasming around her fingers. Waves of pleasure crashed her against the rocks until she lay there, broken and exhausted, falling asleep with her legs sprawled, sheets disheveled, and hand laying on top of her trimmed mound.

The day of Jamal and Maddie's date, Tiffany did her best to dress provocatively without making it obvious. She searched her closet for something casual yet enticing, an outfit that would catch Jamal's attention when he came by to pick Maddie up. She ended up going with a pair of shorts that barely came down past her crotch, putting all of her long legs on display, and an oversized top made of sheer but darkly colored fabric. At the last minute, she also decided to forgo a bra, causing her nipples to push out at the top in a not-immediately-noticeable-but-naughty way.

Pleased with her choice in wardrobe, she sat on the couch with a small smile on her lips, but when Maddie emerged from her bedroom, it became clear that if she actually wanted to stand at chance at getting noticed she might have to go topless.

Maddie did end up wearing the stylish dress Tiffany had convinced her to purchase so long ago and it elevated her attractiveness from pretty to sinfully seductive. The dress clung to her chest, giving her sister's moderate bust a more pronounced appearance. It followed the curve of her waist but not so close that it over-emphasized anything, at least not until her hips, where it flared out before flowing down her thighs. Tiffany had half a mind to ask her sister to turn around so she could check out her ass, which probably looked equally incredible in this magical outfit despite its usual lack of pertness.

"What?" Maddie giggled when she caught her sister's stunned expression. "Is it too much?"

"Maddie, you look great." Tiffany scanned her sister again, thinking to herself that if she were a guy, her erection might have burst out of her shorts from how hot Maddie looked. "Like, really great."

"Thanks. You're the one always telling me I should wear this. I guess I should listen to your advice more often."

That old sting of jealousy came rocketing back and for the first time in a while, Tiffany felt like there was no way she'd be able to compete with her sister. Jamal wasn't going to even glance her way with Maddie around. Yet, at the same time, a sense of pride and elation filled her. Maddie had taken her advice and was thanking her for it. She was actually helping her sister, in the one area that Maddie, despite her superior looks, was lacking compared to her.

"You should. Maybe then you might finally get laid. Or at the very least see your first dick."

"Tiffany!" Maddie exclaimed, seemingly appalled.

She was about to apologize for the comment, feeling bad about embarrassing her sister like that during a shared moment. But then she noticed the flushed color to the older girl's cheeks, and instead of saying anything, she let the silence hang in the air. A professor once told her that if you wanted someone to continue talking, say nothing and eventually, they'd break. Sure enough, after a beat, Maddie continued, her words flying out in a rush.

"Can I get your advice on something? How do you—"

A sharp knock cut Maddie off, startling them both. Jamal was here. With one last glance at Tiffany, Maddie ran off to let him in.

While her sister unlocked the front door, Tiffany considered escaping to her room, hoping to avoid the now less common but still all-too-familiar experience of Maddie's dates treating her like a living ghost. However, she decided to stay, figuring she could at least get to see and ogle Jamal up close, and make some deposits into her spank bank for a later withdrawal.

"Damn, girl," Jamal said as Maddie greeted him, the rumble of his deep voice making Tiffany quiver. "You look fine as hell."

"Thank you," Maddie gushed, leading the tall runner into the living room. Just seeing Jamal made Tiffany's decision to stay worth it, his toned physique apparent even under a pair of dark jeans and a tight purple polo. Her imagination was already conjuring up some ammunition for later that night. She fully expected them to mostly ignore her, as had happened so many times before, but Maddie surprised her by gesturing over and saying, "This is my sister, Tiffany."

Jamal's dark eyes turned toward her, and Tiffany's heart pounded in her chest as his gaze roamed across her body, tracing the length of her exposed legs and briefly pausing when he reached her breasts. "Apparently hotness runs in the family."

If the peaks of her nipples weren't visible before, they certainly were now.

"Thanks, Jamal," Tiffany said, as it abruptly occurred to her that maybe, just maybe, she still might have a chance. "You're bringing some heat yourself."

Jamal responded with a half-smile that nearly made her melt into the cushions.

"I still need a few more minutes to finish up my make up," Maddie said, apparently oblivious to the sudden electric tension between her sister and her date. "I'll try and be quick. Okay waiting?"

"Yeah, not a problem," Jamal said, eyeing Maddie's ass like a panther tracking its prey as she left the room. Tiffany couldn't blame him. Glancing over as well, she saw the obvious outline of her sister's bountiful butt beneath the slinky fabric, confirming her earlier suspicions about the dress's impressive effects. She was in the middle of telling herself that maybe Jamal really was out of her reach when Maddie's door clicked closed and he returned his attention back to her.

"So," he said, dragging out the syllable and sauntering closer until he stood towering over her. Tiffany could smell the musky hint of his cologne, see the cords of muscle in his arms. With their height difference, and with her on the couch, she was in the perfect position to turn her head and stare at the bulge in his pants. But she resisted, despite the heat within her threatening to fog up her glasses, and once again kept silent, still, until Jamal continued his thought. "I heard a rumor about you and the guys your sister dates."

"Oh," Tiffany said, both her eyelids and voice dropping seductively lower. The implication in that statement sent her into a lust-filled frenzy, and she was already planning on tearing off her shorts and masturbating herself to a furious orgasm the moment Maddie and Jamal walked out the door. The idea that Jamal asked her sister out knowing, and maybe hoping, that Tiffany might make a move on him... "I heard a rumor about you as well."

At this point, Tiffany did turn her sight toward the sizeable swell in Jamal's jeans. She was tempted to unbuckle his pants and beat him off right then and there, and the thought summoned a twistedly perverted fantasy into her head. Tiffany sitting up on the couch and Jamal stepping between her parted legs. His black cock out of his pants and in her hands, the tip inches from her face as she jerked her fists rapidly back and forth. Maddie coming out of her room, fiddling with her purse, before looking up at them and nonchalantly asking, "Ready?" not even the slightest bit phased by her sister jerking her boyfriend off. Jamal grunting "Almost," Maddie watching his cock proceeded to hose Tiffany down with sticky bursts of cum, leaving her face and top a gooey mess. Tiffany lying back on the couch covered in Jamal's spunk, him shaking the last bit of it onto her panting body. Maddie coming over and taking his arm, the two of them heading out on their date, her sister adding as they left the apartment, "I wish I looked that hot wearing your cum."

Back in the real world, Tiffany reached a slender arm toward Jamal, a moan escaping her lips when her palm pressed against the absurdly thick snake hidden in his jeans. Her brown eyes burned with a horny hunger behind her glasses and she stared up at him with a savage lust. "Come by tomorrow and we'll see how true both rumors are."

Maddie's door reopened and Jamal stepped back to put some distance between them, reluctantly forcing her hand away from his denim-covered dick.

"Ready?" Maddie asked, making Tiffany shiver from the fantasy still at the top of her mind. Jamal nodded and the two walked hand in hand out the door, the athlete giving one last thirsty look Tiffany's way. Within ten minutes of their departure, she had already made herself cum twice.

Tiffany had difficulty concentrating the next day during her classes. The anticipation of meeting up with Jamal caused her mind to continuously wander and had her squeezing her thighs together in her seat. She ended up leaving her last class early just to get home and get herself off one more time before he came over, slowly rubbing herself on the couch while thinking about what last night must have been like for him with Maddie, how much her sister's revealing outfit must have worked him up.

One hand squeezing her breast and the other tracing circles on her clit, she pictured Jamal checking out Maddie's on display tits. She licked her lips remembering the cheeks of Maddie's ass and the way he focused hungrily on them. With two fingers inside of her, she edged herself while thinking about Jamal on his way over, equally excited for his hook up with Tiffany after Maddie failed to put out... or even more, only going out with Maddie in the first place just to get to her. By the time he knocked at their front door, Tiffany was so worked up and close to cumming that she answered dressed only in a pair of skimpy pink panties, the garment askew on her hips to the point that her sparse dark pubic hair stuck out the top.

"God damn," Jamal said upon seeing Tiffany's near nude form. She grabbed him by the hand and yanked him inside, slamming the door shut behind him. Telling him to come on, she quickly led them to Maddie's room, the pale cheeks of her small butt half hanging out from her underwear. With her long legs, flat stomach, partially exposed ass, and perfectly perky tits all bared for his roaming eyes, Jamal's cotton joggers were already tenting out obscenely by the time Tiffany dropped to her knees in front of him. "Shit girl. And I thought your sister was fine."

Tiffany let out a passionate whine at the pussy-gushing compliment and at the sight that greeted her down on her knees. A small animal could fit inside the tent Jamal had erected directly in front of her face. She could see its thickness molding the fabric of his pants and extending down, down, down. His dick had to be huge.

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