The Other Sister Pt. 2 [MF] [Cheating] [Handjob]

Comments and feedback are greatly appreciated as I continue this WIP story. Definitely helps in terms of motivation and encouragement!

Part 1 linked in comments!

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Three days later, Ashley got her chance. Over the last few days, she had masturbated herself to sleep every night and on at least two occasions during her morning showers. The memory of her forbidden and taboo encounter with her sister’s boyfriend brought her to a powerful orgasm every time, but it wasn’t even about him. She barely thought about his cock or his face as she came. Instead, it was always about the twistedness of the events, of the act of pulling attention away from her sister and toward herself, and deep down inside, in a place she would have never willfully uncovered, of degrading her prude of a sister, her sister that always came in first… except for now.

So, when Dan approached her while Maddie was in the bathroom one night and said he’d been thinking about what they did and that he wanted to do it again, Ashley was more than ready and made plans for another night of debauchery. They waited until the next day. Dan was going to see Maddie for a date later that night and came by beforehand to meet up with Ashley while Maddie was still in class.

“Come on, let’s raid my sister’s panty drawer,” she said. The sneakiness of the situation already had her dripping and after she let him in, she tugged him toward the hallway leading to her and Maddie’s rooms, barely able to contain her excitement. “I want to see what other naughty pairs she has in there.”

“Actually,” Dan started, a slight note of hesitation in his voice worrying Ashley that he might have changed his mind. “I was hoping this time we might do it with one of your panties.”

Ashley let go of the doorknob to Maddie’s bedroom and turned to face him with wide, lust-crazed eyes. Her sister’s boyfriend was actively choosing her over her sister in that moment. He didn’t want to bother with her sister’s panties. He wanted hers. He’d rather blow his load all over her panties than Maddie’s, the one he was actually dating. Ashley let out a heated breath and said, “Yes.”

Ashley watched as Dan rifled through her open panty drawer. She braced against the side of her bed, arms supporting her lanky body, hips thrust outward. She resisted the urge to slip a hand down between her legs from how turned on she was as her sister’s boyfriend touched and explored her various underwear, occasionally pulling one out to get a better look before returning it and continuing his search.

“Are they better than the ones she has?” Ashley asked, voice heavy with arousal.

“So much better… skimpier, sexier…” Dan said holding up a black thong Ashley had bought some time ago but only worn on two occasions previously, having only rarely gotten a reason to. He turned toward her, his choice in hand. “Like this one. Maddie would never wear something like this.”

Ashley grinned. She pushed herself off the bed and went at his pants, rubbing her palm against his length and making him moan. Her eyes burned with intensity behind her glasses, indulging in every detail of Dan’s face twisted in pleasure, all because of her. His eyes screwed shut, his jaw clenched, nostrils flared as she cupped the bulge of his cock and stroked her hand up and down. Ready for more, she popped open his button on an upward stroke, unzipped him going down, and then dove her hand inside to grip his warm shaft and tug him out of his pants.

Beating him off with one hand, she led him over to the bed and grabbed her panties with the other, skillfully laying out the risqué garment without missing a beat on his cock. Dan gasped and moaned, Ashley’s hand jerking him intensely. “Are you enjoying this? Are you enjoying me pumping your dick instead of my sister? Jerking you until you spill your load all over my slutty little panties?”

“Oh god, yes. Fuck, you’re so hot,” Dan groaned, making Ashley squirm from the heat building between her legs. Once again, the depravity of hearing her sister’s boyfriend talk about her like that drove her wild. It nearly gave her a mini-orgasm when he added, “I jerked myself off so many times over the past few days thinking about you in a pair of panties just like these.”

“Ooohhh, that’s so hot,” Ashley hissed into his ear, the steady rhythm of her jacking picking up in pace, the fapping of her fist against him like the beat of a perverse drum. “Did you really jerk yourself off to me that much? You didn’t jerk off to Maddie at all?”

“Just, ungh, once,” Dan admitted. He opened his eyes to stare at Ashley’s hand pumping across his shaft, the tip sticking out beyond her fist and pointed at the skimpy pair of black fabric on the bed. “I tried to think of her in a sexy pair of panties but, ah, after last time, I couldn’t help checking and, ohhhh fuck, you were right. Her ass is kind of flat. Big, wide, and flat. Fuck! Not like yours. Your ass would look so much better in a thong than, shit shit shit!”

Dan could barely finish his thought. Ashley was in a frenzy, feverishly jerking him off at this point, almost flooding the panties she was wearing with her own cum from hearing Dan talk about Maddie’s butt and saying he preferred Ashley’s. Before she could reach her own orgasm, she felt the first pulse of Dan’s cum rocketing up his shaft. She quickly snatched her panties off the bed, bunched them up, and held them against his tip, allowing him to spew his thick load directly into her thong. “That’s it. Soak my panties.”

After he finished coating her underwear and hand in sticky jizz, Dan put himself away and checked the time. Realizing the late hour, he quickly ran off to meet Ashley’s sister for their date, apologizing for having to dump and dash. Ashley didn’t mind. She needed to clean up and then get off herself. Unlike last time, Ashley did decide to do a load of laundry and made her way to her sister’s room to grab her dirty clothes as well, her messy panties still in hand. She pushed open Maddie’s door and walked toward the closet. Opening Maddie’s clothes basket, she dropped her cum-covered panties on top of her sister’s dirty laundry… and then froze in her tracks.

There, right near her deposited thong, was the green pair of Maddie’s panties Dan had cum on days previously. Ashley flushed, the desire emanating from her sex hitting a boiling point. Short, fast breaths rushing past her lips, she was about to lower her hand into her tights when she remembered their sticky state. Darting her head around, she saw a slinky dress hanging nearby, a revealing number Maddie had purchased under Ashley’s encouragement but never worn. Using the inside of the dress like a rag, Ashley wiped her herself clean.

Satisfied, she licked her lips and slipped her hand down to her wet and waiting lower lips. She gasped as she frantically slid her increasingly slick fingers across her cunt and over her clit, eyes concentrated on her sister’s panties.

The knowledge that Maddie had worn them, the very pair Ashley had jacked her boyfriend off onto, that her sister had unknowingly had Dan’s dried cum against her, cum that Ashley had coaxed out of him while he thought about her and not Maddie, that very pair itself right next to Ashley’s cum-soaked ones, also drenched from Maddie’s boyfriend getting off to Ashley and not her. All of it swirled and mixed together in Ashley’s mind, driving right to her flooded cunt until less than two minutes later she was screaming in orgasm, legs quivering and shaking, inside of her sister’s room.

By the time Maddie returned home later that night, she had frigged herself to two more orgasms. Once while sitting on the vibrating washer and then again while folding their clothes, the now clean green panties sitting at the top the pile.

Ashley began formulating plans for future fun, but her and Dan never got another chance at their masturbation play. Maddie broke up with him a few days later, much to Ashley’s surprise. Usually it was the other way around, with the guy breaking up with her, likely as Ashley surmised because of Maddie’s reluctance to do anything sexual. Even more surprising to Ashley was Dan messaging her online shortly after the breakup and asking her out. Naturally, she declined, feeling that it would be inappropriate to go out with her sister’s ex. Plus, truth be told, she wasn’t even interested in him. What really turned her on from their time together wasn’t him, it was what they were doing, and how it related to her sister.

“So, what happened with Dan?” Ashley asked a few days after the breakup while she and Maddie sat reading on the couch. She wondered how Maddie would react. Ashley almost never talked to her about her boyfriends or dating life, but she was genuinely curious and was admittedly a little worried about what Dan might have told her after. “Sorry if I’m prying. You don’t have to talk about it if you don’t want to.”

“Oh, it’s okay,” Maddie said laying her book in her lap, her eyes brightening up just the slightest bit. “I don’t know. It sounds silly but I just got the feeling he wasn’t that into me anymore. Whenever we were together, like the last time we went out to dinner, he just seemed distracted. Like his mind was elsewhere.”

Ashley tried to stay as still as possible and not to react in a way that would give away her pounding heart and quivering sex, a rush of both guilt and excitement hitting her all at once. While her sister might not have known why Dan’s interest in her suddenly waned, Ashley was certainly aware. Never in a million years did she imagine someone would lose interest in her sister because they were busy thinking about her. To steal that sort of attention away from Maddie, from her sister who always ranked above her, it made her nearly drunk with arousal. At the same time, she felt guilty over what she did. Maddie used to do it to her all the time, but never consciously. Everything Ashley did, she did on purpose.

Worse than the guilt though, was how much the shame she was feeling was turning her on as well.

“I’m sorry,” Ashley told her sister. “But I’m sure you’ll find someone else.”

“Thanks. It’s fine. Honestly, I wasn’t that into him. I just get so surprised and excited whenever a guy likes me. I never expect it.”

“Are you kidding me?” Ashley said, with just a touch too much of irritation. She quickly corrected course, not wanting to betray the anger she was feeling over Maddie claiming to be oblivious to her own attractiveness. “Maddie, you’re hot. You just need to dress to show off a little more. Like with that dress we bought together and I’ve never once seen you wear.” A twisted image flashed into Ashley’s mind. Her innocent sister, seemingly unaware of her own beauty, wearing the silky dress, the fabric hugging her curves as she slowly sunk to her knees in front of a date. The idea of it slammed into her and her breath strangled in her throat. Degrading her innocent sister like that by imagining her doing something so dirty gave Ashley an unexpected thrill.

“I’m getting kind of tired,” Maddie said, too busy blushing to notice Ashley’s flushed state. She got up from the couch to head toward her room, leaving a frustrated Ashley behind, too annoyed at her sister cutting off their conversation just when it was getting good to register Maddie adding before heading in for the night, “Thanks for asking though.”

Instead, Ashley sat there, stewing in her displeasure. She wished Dan and Maddie were still together because with the irrational anger she was feeling, she would have called him over and jerked him off right outside her sleeping sister’s door. Standing behind him, her body pressed against his, she’d pump her fist onto his cock, one hand on his shaft, the other fondling his balls. He’d moan her name, getting louder and louder, until just as he was about to blow, Maddie would open the door and he’d blast cum all over—

Ashley gasped and arched her back off the couch, her hips rocking into the fingers hidden under the blanket she was using to cover herself. Quick hitches of breath entered her lungs, her orgasm barreling through her hard and fast, until she flopped back into the cushions, spent and satisfied. She really hoped her sister didn’t stay single for long.

After that night, Ashley and Maddie’s relationship changed forever. On the surface, they talked about the latter’s dating life a lot more. Ashley asked more often about how things were going with her and the guy she happened to be seeing at the time, she was always there to talk whenever they broke up with Maddie or she broke up with them, and Ashley gave her sister advice as best she could, always pushing for Maddie to open up more but rarely succeeding. Maddie seemed to appreciate all of it, happy over her and her younger sister talking more about things they never had before, even though Ashley got frustrated whenever Maddie’s shyness stopping her from venturing too far into the topic of sex.

Below the surface, Ashley’s sex life was better than it had ever been, propelled forward by numerous encounters with Maddie’s boyfriends. She usually waited until they’d had a few dates before making her move, knowing full well that Maddie’s purity left them pent up, wanting, and sexually unfulfilled. At first, it took a little work, with her dressing a little more provocatively or “innocently” bending over while in a baggy scooped-neck top. Eventually though, she was able to tell which guys she could be a little more direct with, the ones she could simply walk over to when her sister wasn’t paying attention and run her hand along their dick. One way or another, however, she’d sooner or later have them moaning and groaning while giving them what her sister wouldn’t.

After a while, there wasn’t a single guy Maddie had dated that Ashley hadn’t brought to climax, almost exclusively in the most fun and twisted ways possible. Like with Dan, Ashley’s source of pleasure was never just the guys themselves, although under any other circumstances, she would have readily acknowledged how attractive they were. After all, her pretty sister wasn’t going to reel in schlubs. Their attractiveness helped but it only served an additional bonus to Ashley’s true thrill of taking away the attention and sexual excitement that belonged to her sister and redirecting it toward herself. She got off on Maddie’s boyfriends getting off because of her—and on multiple occasions there was an extra added layer that rapidly brought Ashley to her own series of thunderous climaxes.

Most of the time, Ashley would simply give Maddie’s boyfriend a handjob, beating them off as they panted and moaned and twisted in her pistoning grasp until they came fat, heavy ropes of jizz. At a certain point, she managed to get one of them off in every room of the apartment: her and Maddie’s shared bathroom, her sister’s towel “accidentally” receiving the brunt of many multiple cumshots as Ashley moved out of the way when they started firing off to avoid their blasts; the living room, where cum often splattered the coffee table; even the kitchen, where sticky cum blended right in with the dirty dishes in the sink. Those night, Ashley usually ended up convincing Maddie to do the dishes.

However, Ashley’s favorite place was her sister’s bedroom. She tried her own room twice more following that time with Dan, but when one guy managed to get a single shot of cum on her dresser, she placed her room off-limits. Ashley didn’t want their cum all over the place. They weren’t her boyfriends, after all. Since it was also always risky to do it in the living room or kitchen, Ashley convinced herself that Maddie’s room was the best possible option by default. It also helped that every time she jerked off one of Maddie’s boyfriends and their cum defiled her sister’s stuff—numerous loads having painted her bedsheets, panty drawer, carpet, and even desk chair—her orgasms that night were coincidentally extremely powerful.

Two occasions especially stuck out in her mind, prime examples of the other added layer that often enhanced the experience.

The first was with Edward, a somewhat dorky and lecherous guy that very obviously had a thing for breasts. Ashley constantly caught him staring at Maddie’s rack, and she was overjoyed when after a bit of convincing she actually got her sister to wear a somewhat revealing top around him, the neckline showing off some of her modest, but impressive when compared to Ashley’s, cleavage. When Ashley got him into Maddie’s bedroom the next day, she knew exactly what she wanted to do.

“You like Maddie’s tits, don’t you?” Ashley said, her fingers barely managing to encircle Edward’s fat shaft as she pumped her hand up and down. He was surprisingly thick for someone of his build. He nodded in response, gasping out a “yes” that made Ashley bite her lip and pump faster. “I get it. They’re bigger than mine, but I wonder how much bigger.”

Ashley let go of Edward’s cock. He let out a whine of disappointment but quickly replaced her hand with his own while she made her way over to one of Maddie’s dresser drawers. Pulling it open, she rifled around before grabbing something and bringing it back over. Edward’s eyes went wide when she held up one of Maddie’s bras.

“Hmm,” Ashley said, posing with the garment in front of her own chest. “Still a little hard to tell. Guess there’s really only one way to really see the difference.”

Dropping the bra down onto Maddie’s bed, Ashley yanked her shirt over her head, exposing her own smaller breasts to Edward’s eyes, her light pink nipples already hard from arousal. It was only for a brief moment, but Edward let out a “fuck” of passion, the precum leaking out from his tip lubricating his increasingly rapid strokes. Ashley could tell he was close. She snatched the bra off the bed and put it on, the bigger cups completely enveloping her boobs, momentarily hiding them from view.

“Yeah, her tits are definitely a cup size bigger,” Ashley said with a frown, looking down at her chest covered with her sister’s bra. She turned her eyes back up toward Edward, a wicked glint sparkling past her glasses. “I don’t know though. Hers might be bigger but I bet they’re kind of saggy. Mine are much perkier. No sag at all, don’t you think? I mean, I didn’t even need a bra.”

Tugging the straps off her shoulders, Ashley pulled the cups of her sister’s bra outward, forming two small bowls and re-exposing her tits to Edward’s gaze. Teeth gritted, he stared at the small, pale cones drinking in every inch of them.

“Ungh, yes,” he said, his hand a blur. “They’re… fucking… perfect. So perky and perfect.”

Ashley dropped to her knees. With one hand she held the bra down and with the other, she returned to stroking Edward’s cock. “Fill my sister’s bra in a way these perfect, perky tits never could. Empty your load into the bra she needs for those saggy tits of hers.”

Ashley erupted in orgasm as the first ropes of Edward’s cum landed inside of Maddie’s bra.

Ashley’s second favorite incident during this time was with Matt. Maddie ended up dating him for a while and Ashley thoroughly enjoyed her sessions with the sweet but very clearly horny honor student. Before this particular night, Ashley had jerked him off twice before and discovered that not only did he have an impressively sized cock, he also produced the biggest, heaviest loads of all of Maddie’s boyfriends thus far. He had completely drenched Maddie’s pillow on their first occasion and on the second had left her hair-ties swimming in sperm.

But Ashley had found out that what Matt really thought about often was cumming on Maddie’s face, and with the amount of cum he tended to produce, she imagined that he would absolutely be able to cover every sweet, innocent inch of her sister’s features. However, knowing that something like that sadly wouldn’t be happening anytime soon, she decided to indulge him in the best way possible while still getting her own pleasure in.

“She does have a really cute face,” Ashley said. She was kneeling on the floor of Maddie’s bedroom jacking Matt off, his lengthy member extending out from her fist and pointed at the iPad she held in her other hand. On the screen was a picture of Maddie, zoomed in on her face. She looked especially pretty in that image, the wind blowing at her long hair, eyes crinkled from her smile. The only thing, as always, was… “Except for her nose. It’s kind of big. I was always proud of my nose compared to hers.”

Ashley zoomed in a little further on the picture, focusing on her sister’s nose, the uniquely shaped feature taking up most of the screen. She adjusted her grip and jerked Matt faster, the thrill of calling attention to her sister’s imperfection making her hot between the legs. Yet, even with Maddie’s nose big on the screen, she still looked fucking cute.

“She’s really self-conscious about it,” Ashley continued. She turned her gaze away from the image of her sister and toward Matt above her. His eyes were near slits concentrating on the picture of Maddie, his breath coming out in ragged grunts. She heard him gasping under his breath, “oh fuck, Maddie,” over and over again, his hips beginning to rock toward Ashley’s fist, humping himself into her hand. “It actually kind of works for her though, you know? That big, awkward nose on that cute girl-next-door face. You would still do it, right? You’d still cum all over her and her awkwardly shaped nose.”

Matt let out a strangled cry and Ashley quickly angled his cock away, wanting to keep her iPad safe from the onslaught. Instead, she pointed his erupting tip at the nearest place she could, which just “happened” to be Maddie’s open clothes basket. Nearly 10 thick, gooey, heavy streams of cum fired out and landed all over her sister’s dirty laundry. By the time Matt was finished, it was like a branching river of cum was running across her clothes.

After Matt left, Ashley ended up masturbating herself to orgasm on her sister’s floor, her eyes on Maddie’s cum-drenched wardrobe. She was going to do the laundry afterward but told herself she was too tired after working herself through two incredibly powerful climaxes and decided to just do it tomorrow. To save herself from getting caught, she mixed all of Maddie’s dirty laundry together to spread the cum out and then tossed everything into the washer to sit until the next day. She ended up masturbating again before bed that night.

Things continued like that for a while between Ashley, Maddie, and Maddie’s boyfriends. It wasn’t until Malik that things finally escalated.

Source: reddit.com/r/sexystories/comments/jcm3qn/the_other_sister_pt_2_mf_cheating_handjob