58 comments/ 460473 views/ 271 favorites Wicked Stepsister By: en_extase Do not reprint this work on any other website, or any medium, without the express consent of the author (me!). Synopsis: Madison's parents are away, and she is planning on spending a summer day at her house with her boyfriend. Her antagonistic step-sister schemes to drug them both in an attempt to sexually manipulate the two of them against their will. Wicked Stepsister "Hmmmm…" she mused. "Maybe take a little nap first? It feels nice…" She flattened out her chair completely and turned over onto her stomach. "Gimme some more sunscreen…" He tossed the bottle over to her. "Hey! Put it on my back!" Her pout did not go unnoticed. Tyler lazily got out of his chair and kneeled over her, pouring more lotion into her skin, rubbing into her back. "Mmm… That feels perfect…" He bit the back of his tongue to prevent a sigh. There was no denying he'd been turned on all day, and straddling his girlfriend wasn't helping. I can't wait 'till we finally go to her room… His inhibitions were still too loose for him to care about his growing erection at his trailing thoughts. It didn't go unnoticed. "I can feel that," Madison purred. "Yeah, uh, well…" "Better relax," she sighed, her eyes still closed. "You don't want me while I'm all sleepy, right? You want me to be your energetic little kitten…" Hell yes… "Uh huh… So take your nap and I'll play with you later…" Just play it cool. Good things come to those… So he reluctantly rose away from her and fell back into his own seat. Closing his eyes, he tried to breathe deeply and relax, tried to nap a little and pass the time. But he could still see his girlfriend's body; still feel the need between his legs. Just gotta chill for a little while… He tried to push his mind to think about anything else. He listened to the breeze, a bird chirping… I hope her sister doesn't come home and interrupt us… The tent in his shorts, which had finally subsided a few minutes earlier, suddenly began to stir back to life. The corners of his lips curled into a small smile as he recalled seeing her earlier that day in that little outfit. Suddenly he was picturing her in his girlfriend's swimsuit… He shook his head. Bad Tyler. He switched to the old standby of dully counting backwards from one hundred. Somewhere in the seventies he managed to stop thinking of Amber, and he finally dozed off like his girlfriend nearby. Wicked Stepsister He reciprocated in kind, and the two went through the motions of having a fun water fight… Although neither of them was fully convinced the other was being genuine. Amber had left an uneasy tension over both of them, and the moody cloud wasn't easy to shake off. Tyler, with a goofy grin, said, "Hope we don't get in trouble!" "What do you mean?" "Well she did say no more horseplay…" He could see Madison's entire expression drop from her face into irritation. "What do you care what she says?" "I- I was just being funny…" He realized his mistake. She stared at him, unflinching, until he cast his eyes away. "Whatever. I think I'm done with the pool. Did you want to stay in?" "Uh, no we can get out." "Okay." Madison pulled herself out first. She couldn't quite decide whether to try and look cute as she did so or not. She was upset at Tyler, and wanted him to know it… But at the same time, she knew she needed to keep his interest and keep him happy. Otherwise Amber would have succeeded in ruining the whole day. The two ended up back on their sun chairs, sitting up to face one another. "So what do ya wanna do now?" Tyler asked. "Hmm…" she struck a thoughtful muse. "Well do you want to stay outside? If we go in, we could… watch a movie, maybe make some lunch…" She let her words hang for a moment, and then, "…or maybe we could just go up to my room." Tyler's eyes lit up immediately. "Your room, huh?" "Mm hmm. I know it might not be the most exciting place… but at least we can finally have some privacy?" She was finally regaining her flirtatious confidence. "Privacy would be nice." "Yeah…" she leaned forward and put her hand on her boyfriend's leg. "I'm sure we can find some way to pass the time." Her fingers slid up to his thighs, and the corners of her mouth crinkled up even further as she saw the twitch in his shorts. He swallowed in anticipation. "Definitely…" Looking around briefly, he grinned, "And it's getting pretty hot out here anyway. We probably shouldn't waste any time." Madison let her fingernails trace off of his skin as she stood up. "Kay… Let's also make sure we don't, um, dehydrate?" She motioned toward the wine coolers. "Got it," he rose himself and grabbed the container of drinks. Things are finally looking up… The two made their way to the house door, with his girlfriend leading the way. As soon as they opened it, the cheerful chatter and laughing of her step-sister drifted down the hall. Madison tried to ignore it, and hoped that they were at least in one of the side rooms; hopefully watching TV or something… A lump in her throat grew as they neared the kitchen and she realized that's where they were, and they'd have to pass through the room with them. Amber's friend Becca saw them first. She was standing near the doorway, some kind of drink in hand, and turned to look at them. Her face already wore a broad smile from laughing, and she casually greeted the two, "Hey guys, how are ya?" She had glanced at Madison, then briefly at Tyler, then let her eyes rest back on his girlfriend. It wasn't merely boyish wishful thinking when he wondered, 'Is she checking her out…?' "Hi," Madison replied neutrally. Wicked Stepsister Becca stood up straight and turned her back to her. Madison looked on impatiently, trying not to stare at her ass, barely hidden in the little skirt. She couldn't help wondering if she could pull off that look, and she thought she could… Focus, focus! "Okay, I have a… tiny confession…" she turned on the computer monitor sitting on the desk and tilted her body back to Madison. "There might have been a- um… little something extra in your drink…" Oh crap… Madison leaned her head forward, her hands pulling against the back of the chair again. "What…?" "Don't spaz out or anything." Becca sat down on her knees, her hands resting on her thighs. "It won't hurt you. It just, like, chills you out- you know?" She looked up at Madison in the chair, trying to be cheerful and innocent. What is she gonna do to me? Where's Tyler? "Why?" sighed. Becca almost blushed. "Come on Madison. You're too cute. I mean… When Amber suggested this little plan…" "What plan?" Madison managed to interject. "Well… I get to spend some time with you. I couldn't resist… I always see you when I come over, and, well, your sister knows I notice. You know how, uh- sexually tuned she is… I mean," she bit her lip and rolled her eyes to the side, "God, I can't believe I'm stuttering around you…" Jesus, what the fuck. She has a crush on me? I'm fucking straight! Get me out of this mess! "Ummm… So where's my… boyfriend again?" she tried to sound serious with the emphasis and hoped not to tick Becca off. "Okay, okay… Soooo… You want to see him? I mean, I guess I have to show you… It was part of the deal," she drummed her fingers on her skin as she rose back up to her feet. "Just… Try not to freak out, okay? I mean… Maybe you can't anyway!" *What* deal… Becca moved to the keyboard and started running some program. Suddenly a window popped up… Madison tried to look around Becca to see what it was, but she intentionally kept in the way. "So, this might seem kinda twisted… So I'm sorry for that part, but… Um…" She finally moved out of her view. Madison's jaw dropped. It was some kind of video feed from a web cam. It wasn't perfect picture quality, but it was pretty damn good. She vaguely recognized the room as her step-sister's. The enormous bed with the hot violet silk sheets was the dead giveaway. The rest of the picture didn't dawn on her right away. It was too ludicrous to believe. She went into instant denial. Tyler was on the bed, wearing just his shorts. His arms were stretched above him, slung to the bars of the headboard with pink fuzzy handcuffs. He was blinking hard and rolling his head back and forth. Amber briefly walked across the view of the camera, still just wearing her black panties and halter top. "See?" Becca chimed in, "He's totally fine!" Madison just stared for… she didn't know how long. Finally, "What… What is he doing there… With her…?" Becca was next to her now, trailing the tips of her fingers along her shoulders, down her arms. Madison tried to ignore it, but for some reason the ticklish touch sent electricity through her body. She felt her head buzzing again. "I know… It's kind of mean, isn't it? At first I thought… No way would I do this! Your sister can be really… sadistic sometimes. But…" she sighed, "She knows what I like. You have no idea what she can do, Madison… And once she agreed to let me have some fun with you if I played along… Well, how could I resist?" Her hands were sliding down Madison's sides now as she stood directly behind her. She squirmed in her seat. "B-Becca… Just- can you let me go? I mean… I'm not, um- that way… Okay? I just want to get Tyler and, umm… That'll be it," she was grasping for a solution, "Like it- like it never happened, okay?" Becca's fingers gingerly squeezed into Madion's skin. "Umm… Sorry but- I don't think so. I think that you'll… um, warm up to me pretty soon…" The way she said it left Madison with the eerie feeling that she had something else up her sleeve, something she wasn't fully telling her about. "P-Please Becca…" she stammered. "Shhh…" Suddenly Madison felt warm breath on her neck. She closed her eyes at the sensation, which sent way more tingles through her than it ever normally would… Then shot them back open when she felt a soft pair of lips press against her skin. "I- I… I'll scream…" she tried to warn, to reason… to anything… Becca kissed her again, further up this time, along her jaw. "No you won't… You can't…" Madison took a deep breath. Fuck this, if being nice won't work… She let it all out to shriek as loud as possible. It only came out as a sappy sigh. A little hummm… escaped her lips. Oh shit… Why can't I… "Mmm- I told you… Just relax, it will feel good. You won't be able to help feeling good…" It can't feel good. What the fuck is going on! She ignored the butterflies swirling in her stomach. It's just nerves… I'm freaking out… That's all… I just need to concentrate… She tried to tilt her head away from Becca and think. Her eyes narrowed on the computer screen. "Oh… I guess I forgot the volume," Becca mused. She walked back in front of Madison and reached over to the speakers, clicking them on. "This is gonna be like, a crazy show. I mean, you don't have to pay attention to it… I'll be perfectly happy if you, um- focus on other things…" Her smile showed a trace of devious confidence. She let her hands run along her legs to the hem of her skirt and playfully teased the cotton around her fingernails. Oh my god, oh my god, what the fuck… Becca took another step closer, and Madison couldn't take her eyes off her. What is she gonna do to me… She felt lightheaded again, unable to concentrate. And then she heard Tyler's voice through the computer. It was a little muffled, like the mic wasn't close to him, but he was clearly audible… "Come on Amber, just let me get up…" And she heard the unmistakable sound of her step-sister's cocky giggle. Wicked Stepsister "I thought you were showing off for me, you know. Lying out in the sun like that, just waiting for me to show up. You had to know I was coming back. And when you went in the pool with my sis? I saw you looking at me. Were you pretending it was me in the water with you?" She tickled the sensitive part inside his thigh and he groaned again. "Cause I was thinkin' it." Jesus mother fucking Christ… "Really…?" he grunted. Oh fuck, did I actually say that!? Her head instantly shot up and turned to meet his stare. "Tyler! Was that interest I actually heard?" She crawled back up onto her knees and leaned over him, her hands pressed against his chest for balance. "Do you like that I was thinking about you?" His head was swimming. "Uhh…" How do I get out of this… "Too late!" she grinned. "You admitted it." Her body was instantly straddling his again, and she towered over him triumphantly. "But Tyler… I have a little admission to make…" she bent her head down and roamed her eyes around, as if making sure they were alone, "…I already knew the answer." His face flushed hot again and he shut his eyes. God. Damn. It. "The real question is… Who do you like better? Me or my baby sis?" Her hands were running through his hair playfully, and he couldn't help but feel mocked. Yet his hardness wasn't going anywhere. "I mean, I'm not blind. I know she's cute." The way she said it was so derisive. "But she's just so boring. Don't you want a little more spice?" Her ass pushed backwards and began to rub against his erection through the board shorts. He couldn't swallow the huge sigh of desire in his throat. "Oh I'm sorry… I know boys can be kind of simple sometimes. I'll try to narrow it down. Let me ask a more direct question…" She leaned up straight and stretched her arms behind her, which pushed out her chest. "Are you an ass man or a tits man?" He knew there was no safe answer out of this… Her butt wriggled against his lap and teased his erection even more. His teeth silently ground in the back of his mouth, trying not to give in to the pleasure. Suddenly he felt all her fingers rake down his stomach. His whole body clenched and he let out a startled gasp. "Answer meeee…" she sang, and repeated the motion with her hands. Tyler coughed out a brief laugh. It tickled. Bad. And while the feeling made him squirm to try and get his abs away, it sent the blood rushing down between his legs. She did it again, and he shook his head, "S-stop it…" "Aww, are you ticklish?" Before he could even comprehend an answer, her fingers were dancing all over his stomach, his chest, his sides. She was practically riding a bucking bull as much as he thrashed against her touch. Sure, he might have been ticklish normally… But now he felt more sensitive than he ever had before. His head was tingling, his breath a literal pant. He cried out for her to stop again. "Okay okay," she soothed. "I'll ask again… Ass or tits?" A brief pause, and she dug her thumbs into the creases of his pelvic bone. "I'll tickle again…" He swallowed. "Okay, okay… tits. Happy?" She smiled triumphantly. "I kinda thought so…" She reached one arm behind her. "So whose are better? Mine or Maddie's?" He knew his girlfriend despised being called that. Fucking bitch. Fucking hot bitch. "Still no answer huh?" She flexed her fingers in front of him devilishly. "I- I dunno…" he stammered instantly. The thought of being tickled again mortified him. He could feel the pre-cum leaking against the insides of his shorts… He was glad the material was thick enough to hide it. "What's the problem? Just be honest with me… It's not like I'll get mad or anything…" Yeah, the hell you wouldn't. "I just…" his mind raced for an excuse, "…never thought about it." God. Lame. She raised her eyebrows in disbelief. "Tyyyy-ler… I don't know if I believe you. But since I kind of like you… I'm going to give you the benefit of the doubt. So what we're gonna do, right now, is think about it." Her hand reached behind her, and with effortless movement, untied the knot of the cloth behind her neck. The cloth fell forward off of her chest and landed on Tyler's stomach. His mouth felt instantly dry as he stared up at her naked tits. She brought her hands up to them, and held them up a little… Let them drop back down. They bounced slightly. "So what do you think? I know they're bigger than hers… Do you like big tits or little tits?" she screwed up her eyes like she was concentrating overly hard. Woah… "Tyler?" she asked innocently. "Yeah…" She leaned over slightly, making them hang over his face. One of her hands steadied herself against the bars of the headboard. She subtly moved her other hand back to his stomach, walking two of her fingers along. "Answer me?" He paused a little too long, and she dug back into his abs, tickling him again. He laughed and groaned at the same time. And shamefully, despite all of it, desperately pushed his hips up into her. Unabashedly trying to hump against her… "Ummm- I'm not sure if this is having the right effect anymore!" she teased. "Do I have to find some other way to make you talk?" "No! No… I like, uh- all kinds..." he panted as he caught his breath. "Just depends on the girl..." Okay, nice. That was good… It was a tiny victory. "I'm not laughing, Ty-ler. We're not talking about some girl… We're talking about me… Right here!" she brought her hand off the bedpost momentarily to swat the top of his head. "Now since you're apparently too dense to make a decision on your own… I guess you'll have to get a closer look…" His eyes widened as he realized she was allowing her body to drop down, bringing her tits right to his face. "Now tell me… Do you like them? Look… Not even any tan lines…" He stared mesmerized at her beautifully pale skin. Her nipples stood out invitingly… Is she horny? Does she actually get off on this? "I hate tan lines… I know Maddie has them… She goes through all that effort for that silly tan, and then you get her naked… It's like a funny tattoo or something… Don't you like this better?" her voice was low. Seductive. "Why don't you try a taste… Just a little kiss…" she leaned down lower, one nipple grazing his lips. "A-Amber…" "It's okay, Tyler… Nobody has to know…" Would she tell Madison…? "I can't…" He was clinging to his last shred of dignity. "Come on, I'm begging you… It's not like you have a choice… right? If I'm making you do it… It's not wrong…" She intentionally pushed her ass backward into his erection again, eliciting a hiss of delight from him. And then he lost it. He gave her a tender kiss on her breast. And with one, came another. And another. "Yeah… Kiss them all over… You can lick too…" she moved her chest side to side, forcing him to alternate his attention between her tits. "Don't forget this one… Mmm… So have you decided yet, Tyler? Do you like mine more?" In an attempt to not answer, he let out his tongue and began to enthusiastically lick across her nipple. She gasped out, "Ohhhh Tyler!" He had no will to stop his efforts with that kind of encouragement… And Amber's lips melted into a sultry, open-mouthed smile and she tilted her head to the side and stared directly into the camera.