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Leon wasn’t cool. He was never popular back in school, let alone with his colleagues. He was typical, with the whole boy next door look. If he weren’t so socially inept, he could have any girl he wanted. But he didn’t want just any girl. He wanted you. His older sister. Step-sister. The part he always left out. He had a crush on you. A downright fucked up, nasty one.
He was a pervert. A self-admitted one too. He’d steal your used panties from your laundry basket and sniff them, or use them as a cum rag. He’d cum all over the fabric, smearing it in and wishing it was your pussy. He knew that you’d think he was a total freak. But that was the appeal. You were mean. A real bitch, but Leon would never call you that.
From day one, you hated him. The day his mother met your father and stuck you together as step-siblings marked both your fates. You didn’t want Leon, didn’t want a brother. As you grew up together, not much changed. You still called him names and ate his leftovers. You’d push him out of the way and point the finger at him. The difference was that he let you. He let you walk all over him because he’d never felt this way about anyone else. He certainly didn’t want to either.
Leon was your so-called brother, and there he was. Pining over you and your pretty face. Your snobby attitude and cruel words. Your body. The suspicious amount of times he’s walked in on you changing. You never questioned that, never questioned small things that went missing either. If you ever asked, Leon would say you must’ve lost it. That was another thing you didn’t know about. You’d never guess that your step-brother jerked off in your bed when you weren’t home. That he humped the pillow you rested your head on.
You’d never know that your missing lip gloss and necklaces were residing in his bedside drawer. Anything that had touched your skin, anything he could get his hands on. Leon knew it was wrong. He knew he was weird. He knew it wasn’t normal to act overly affectionate with his bitchy sister. To be at your beck and call, ready to do anything you asked. Maybe you were too blind to see it. But who in their right mind would suspect something like this? It’s why you were so careless. You never thought your brother would be such a pervert.
It was a winter's day, you’d been out with your friends. You were off on winter break from college, and Leon was a rookie cop. You always had something to say about his line of work, but never in your life would you admit that he looked attractive in his uniform. Another thing you pushed from your mind.
You came home early, not announcing your presence. You’d always retreat to your bedroom or bug Leon. Oftentimes, you’d stand in his doorway and tell him he should clean his room. But ever since you walked in on him-you didn’t visit so often. You recalled the moans on his laptop, girls with fake tits whining for their step-bros. He thanked god he saw you in time to shove his dick under the covers. You’d never forget the look on his face. Blushing like a fool, sheer humiliation in his eyes.
You tried to forget about it. That was until the day you came home early. The house was quiet as you carried your shopping bags upstairs. Quiet, until you reached the top of the stairs. You heard something coming from your bedroom. The door was wide open, yet you’d shut it when you left. It confused you, the debauched noises. Whimpers. Breathy little moans of your name. You thought you were hearing things until you walked right into something truly abhorrent.
Your eyes went right to your bed, the source of those pornographic noises. Leon, your step-brother, on your bed. You looked at his face first, flushed a blotchy red. The blonde strands of his fringe stuck to his sweaty forehead. His blue eyes were shut as breathy chants of your name fell from his lips. That’s when you looked lower.
You couldn’t believe your eyes as they trailed down his body. His shirt lifted to his navel, thighs creamy and legs spread open as he got himself off. Sprawled on your bedspread. He had his pants down to his knees, pumping his cock fast and hard. The sight made your blood boil, watching pre-cum drool down his fingers with every pump and buck of his hips into his own fist.
“You filthy pervert!” You raised your voice in a shrill noise that made Leon jump. His eyes darted to the doorway, his cruel sister standing there. Staring at him with his dick in his hand. In her bed, moaning her name. He looked terrified yet strangely aroused. “Leon! What the hell?!” You dropped your bags on the floor and stomped over to his side.
“What the fuck is wrong with you?!” You slapped his blushing face, snapping him out of it. He looked up at you, sweat beading down his forehead. “Sis? Oh god-,” He panted, cock throbbing in his hand. As soon as you spilled out a slew of curses, beating at his shoulders to get the fuck out, he got it together. You were pissed. He frantically pulled his sweats back up, almost tripping over them as he scrambled to his feet. “I’m sorry. I swear it’s not what it looks like! I-I didn’t mean to-" He sputtered, tears welling in his eyes. He was grasping at straws, begging for forgiveness.
“Didn’t mean to? You accidentally went to the wrong bedroom to jerk off?” You asked in a sarcastic manner. His lips parted to say something, but he choked up at your glare. “You’re sick, Leon. Sick in your head.” You scowled, looking down at him like he was nothing more than a nuisance. “Sis, don’t be mad at me.” He grasped your hips, burying his face into your shirt. His nose bumped your stomach, choking back a sob. He loved your teasing and attention, even if it was negative.
But this time was different. He’d really fucked up. He didn’t know if he could come back from this. “Get off, you creep! Aren’t you ashamed?” You tried to push him off, but he clung to you. “It’s not like that! I-I just,” He fumbled over his words, unable to talk his way out of this. Leon was a disgraceful incest freak. Related by marriage. Nonetheless, the same girl he called his sister.
Your words stung, and he was humiliated. It didn’t stop his cock from tenting in his pants. A bulge beneath the fabric, twitching and needy. He loved when you were mean, flinched when you were nice. “Sis, m’ sorry, I’m so gross.” He apologized again, whined as you yanked at his hair. “Sorry?” You repeated, brows knitted together. “Uh huh, I’m sorry..” He pleaded, wincing as you held his head up by his fringe. “Is that so? Oh, please. I’ll make sure you’re sorry.” Your words made him tremble, anxious as you sat beside him on the bed. He looked down at where your thighs touched, then back to your face. A pretty blush on his face at the slightest contact. What a virgin.
“You’re nothing but a nasty pig.” You hissed, making his lower lip quiver. It seemed to hurt his feelings, but not as much as it made him hard. You glanced down at his crotch, his arousal making itself known. “Ugh, Leon. Can’t you control yourself? Or are you too horny for your big sister? You should’ve heard yourself.” You smiled, wicked and mocking. “Oh, oh god, sis, gonna cum!“ You put on the fakest moan to imitate him.
“Stop it!” He blushed a deeper shade of red, his embarrassment doubling. “What’s wrong, baby bro? You can dish it, but you can’t take it?” You coo, squishing his face in your hands. Your fake nails dug into his baby face, but he found himself leaning into it. His eyes closed, shoulders relaxed. “I-I thought .. Thought you wanted me out of here.” He spoke in broken words. Your touch had a way of breaking him down. He was a bit confused, a little scared as to why you hadn’t kicked him out yet. Despite this, it was exhilarating. A fresh blurt of pre-cum leaked in his pants at your touch.
“I love when you touch me, sis.” He mumbled his pathetic admission. All breathy and slurred. “Especially when you’re mean.” He opened his eyes, blinking away tears. Leon looked so pretty with tears in his eyes, staining his cheeks. “Ew, Leon.” You sneered. “Are you some kinda masochist? You get off on this?” You accused. He nodded shyly. You’d caught him jerking off in your room, there was no use in denying it now.
“That’s disgusting. I should go tell mom and dad what a pervert you are.” You wiped his tears, catching the fear in his eyes. Pupils dilated, wide and darting away from you. “What? No, don’t tell ‘em. Please.” He pleaded. He knew you well enough to know you weren’t fooling around. “Why shouldn’t I? You were bold enough to jerk off in my room. But now you’re too pussy to face up to what you did?”
He whined, “I’ll do anything, just don’t tell anyone.” He grabbed your free hand, squeezed it tight. You scrunched your face. His fingers were sticky. “Anything?” You asked, a nefarious grin on your face. “Anything. Promise.”
You hummed, looking down at his lap again. He was so hard, it made him squirm beside you. “Okay. I’ll take you up on that. I think a little punishment is just what you need.” You settled it.
“Oh, sis..” He practically moaned. This was just like the porn he watched. “I want you to punish me. I’ve been so bad, I know it.” He was all the way gone, moving your hand to palm at his bulge. “I don’t care what you’re gonna do to me. Hurt me, call me names. Just touch me.” He was pleading, a pathetic whimper at the slightest of friction. He was sure you were going to up and leave. Run and tell your parents what a degenerate their son was. But you had a better idea. “I won’t do anything if you don’t stop that whining.” You complained, tired of his mouth.
“You sound like a girl.” You taunted, rubbing the outline of his cock. It made him shudder, but he tried to spare his pride. He didn’t have much in the first place. “No, I don’t,” He defended himself poorly. Already a whimpering mess. “Yeah, you do. You’re nasty, and you moan like a girl. Maybe you’ve got a pussy under there.” You teased, loving his reactions. Oh, so responsive! Your words made him groan, and his hips bucked up against your hand.
His stiff cock that strained in his pants, desperate for more. “S’ hard .. Gonna cum if you keep talking,” He gripped you tighter, a wet stain tainting the fabric. “I bet you will. You gonna make a mess in your pants? Cum for your big sister like the pathetic baby you are?”
Leon nodded, “Uh huh.. Please, please. Don’t stop.” He humped against your hand. His fingers squeezed your wrist so you wouldn’t pull away. Leon was stronger than you. He could shove you down and take what he wanted right then and there. But you both knew he didn’t have the guts. “Big sister,” He mewled, shoving your hand into his pants without permission. You didn’t pull away, “Touch it, sis. Want you to jerk me off.” He begged. “Wow, Leon. You’re so forward. So naughty.” You wrapped your fingers around his cock. Hard and throbbing, you smeared the pre-cum over his tip.
It made his hips buck into your hand. He felt his face flush with embarrassment. Maybe you’d call him small or mock him for being uncut. “You’re leaking so much, Leon. Making a mess.. No wonder you’re a virgin. You wouldn’t last long if you got a taste of real pussy.”
Real pussy? Did you know about that toy he kept under his bed? He whimpered, squeezing his hand over yours. “Ohh-Harder,” He begged. It was uncomfortable to touch himself in his sweatpants, and he wanted you to see what you did to him.
“Harder? Aren’t you one to give me orders?” You narrowed your eyes, sliding your fingers down to tease his balls. All full and heavy, so backed up. “M’ sorry, sis. Can’t help it, you just… just..” He trailed off, struggling to use his words. He felt a thrill, hoping one day you’d step on his balls. “You can do whatever you wanna do. Just don’t stop touching me.”
“Poor baby. My poor baby brother.” You teased, taking your hand out his pants. He protested with a pitiful noise. “Nooo, Don’t, I need you, need it bad.” Fresh tears threatened to fall, his baby blues all glassy. “Shut up. Bad boys don’t get rewarded for being so dirty.” You scolded. He huffed, “I said sorry.” He sounded like a petulant child. “Look..” He attempted to resolve this by showing you what you were doing to him. He tugged his sweats down his thighs, exposing himself to you. Such a fat cock, thick and begging for your touch. “I’m so hard for you, sis. I jerk off to you all the time.” He admitted, more humiliated with each word out of his mouth. But he continued.
“I steal your panties and wish it was your pussy.” He began to pump his cock, lazy strokes. “Smells so good, want you to sit on my face.” He began to pump his dick faster, imagining that. You laughed, made him insecure. “As if you’d ever get the chance! Do you seriously think you could please me?”
Leon faltered, pausing his strokes. “I’d try to.” He looked to you, honesty in his voice. “I’d eat your pussy for hours. Do it til I can learn what you like best. Make you proud of me.” He sounded so sincere, so set on being good for his big sister. “Right.” You were skeptical.
“Lemme prove it.” He sat up straight. “I wanna taste your pussy. Want big sister to squirt on my face.” He placed his hands on your thighs, pushing up your skirt. “In your wet dreams.” You slapped his hands away. “You’re so full of it, Leon. Listen to you.. thinking I’d ever let you do that.” You paused. “Well, maybe one day.” You threw him some false hope.
Leon perked up, “Really? Can I?” He was like a puppy, eager to please. “No. Not today.” You shut him down fast. “When you behave, I’ll think about it.” You said, reaching up to brush his hair out of his face. Dirty blonde, a real looker if he wasn’t so weird. He smiled, relishing in your touch. He began to stroke himself again when you ran your fingers through his hair. “Keep touching me.” He whined. “I wanna cum, wanna be good for you.”
“You’re not doing a very good job.” You bluntly stated. He pouted, “I’m trying. It’s just .. hard to control myself with you.” He pumped his cock faster, his moans filled your bedroom. “Feel so dirty, big sister watchin’ me jerk off.” He panted, looking over at you. “You are dirty. You’re a perv, Leon. No better than a filthy maggot.”
He whined, throwing his head back. “Ohh, god. Yes, fuck. I’m filthy, a pervert.” He growled, pumping his cock harder. “Mhm.. A nasty thing. A very bad boy.” You leaned over and grabbed his wrist. “Not yet, Leon. Bad boys don’t get to cum when they want to.” You ordered. Not one to reward bad behavior. “What?” Leon tilted his head to see you, dazed and confused. “Sis, I dunno if I can hold off..”
“You don’t think so?” You asked, replacing his hand with yours. “Oh, oh! Not if you’re the one touching me.” His hips bucked up, seeking more. “Hush, don’t be such a baby.” You shushed him, teasing the underside of his cock. He shivered and let out a pathetic noise. “Sis, I’m gonna cum, I can’t..“ He whined, fucking his hips up into your fist. It was slick, his cock already leaked so much. If you didn’t know any better, you would’ve sworn he’d cum already.
“I can’t hold it. I-I don’t wanna be bad, but it’s too much..” He nuzzled into the crook of your neck, panting and drooling on you. “Can’t hold it in, oh, oh god,” He went on, cock throbbing and weeping under your touch.
“You’re so pathetic, you’re gonna cum already? Don’t you think that would disappoint somebody?” You asked, slowing your strokes down. “Yes..” He mumbled against your skin, lifting his head up to look at you. His face was flushed, tears staining his cheeks. “Exactly. It would disappoint me for sure. If I let you put it in, you’d bust in seconds.” You snickered.
Leon pouted, humiliated that you were right. He stared at your face, which was focused on teasing his dick. He wanted to kiss you, to lick your skin, cum all over it. That was all in his head though. He knew better than to tarnish you like that. His imagination ran wild at the possibilities of pleasing you. Pleasing you enough to let him do that.
“Try harder.” You gave his cock a hard squeeze that made him moan. “See? I didn’t know I had a sister.” You picked on him, finding those moans awfully high-pitched for a man. “Stop it, sis. You’re being so mean.” He sniffled, dropping his head back on your shoulder. “Stop? Why didn’t you say so?” You paused your strokes, leaving his dick twitching. He whined at the loss of contact. “No! No, don’t stop! I was so close,” He hiccuped a sob, itching to grab your hand and make you finish what you started. “Aww… I can feel that.” You say, ghosting your fingers over the veins near the base of his cock. “You must be sooo pent up, baby bro.”
Leon hummed, “Uh huh. Lemme cum, sis. I know I’m bad, but ..” He trailed off, unsure how to keep going. He’d been more than just bad. Of course he had a punishment come his way. “But what? You’ve been a degenerate. Jerking off to the thought of your own sister..” You said lowly, stroking his cock up and down. His eyes fluttered shut, fearing your words alone could make him bust. “I-I know. It’s so dirty, I’m such a pervert.” He breathed against your neck. You nodded in approval. “That’s right. You’re nothing but a pervert. One that deserves proper punishment.”
He nodded, a miserable look on his face. He knew you were right, but he was no match for his fantasies. To you.
“I think I should start locking my door at night. My creepy brother might get up to something dirty while I’m asleep.” You whisper, wrapping your fingers back around his length. He whimpered, desperately fucking your fist. He was shaking, breaths hitched and panting. “Mm, Yeah. I wanna sneak into your bedroom at night. Stuff my big sister full of my dick til you wake up,” He went on, his words hardly coherent. “O-Or suck on your tits, lick your pussy .. want too so bad,” He rambled, words slurring together. You dug your nail against his slit, made him whine extra loud.
“That’s so fucking gross, Leon.”
He ducked his head, ashamed—trembling under your cruel whims. “You know what kind of guys think that way about their sisters?” You asked. He shook his head no, leaking onto your hand. “Tell me, sis.” He wanted to hear you say it. Needed to hear you call him names and put him down.
“Perverted sickos like you,” You began to pump his cock faster. “But you like this. You love it when I’m mean. Don’t you?” You said softly, faux affection. It was so sweet and taunting, it made him melt. “I do, I love it, love you.” He pressed a kiss to your neck, open-mouthed and warm. “Love you so much, sis. I wanna be good, wanna make you feel good.”
You squirmed when he mouthed at your throat. He was sloppy, clearly had no idea what he was doing. “Leon! Stop that, you animal.” You pulled his hair roughly. He whined against your skin, something akin to a moan. It felt good to be hurt by you. He wanted to beg you to pull his hair, slap him silly. Whatever you wanted. “God, you’re a mess. You need a haircut, too. You’re such a pretty boy.” You let go, trailing your fingers down the slope of his nose. “A sissy, if you ask me.. And what do sissy boys do? Huh?”
Leon was at a loss, dumbed down and focused on your touch. “Dunno, sis.”
You rolled your eyes. Of course not. “Sissy boys take cock. I bet you’d like that. Bet you want a nice fat dick down your throat.”
He wheezed at your words, his stomach in knots. It caught him off guard, turned him on. “Nn-No! I don’t.” He was an awful liar. “I guess .. If it were you,” He added quietly. “If it was you, I’d let you do whatever you wanted to, sis.”
“If it were me? You’re saying you want me to fuck you like a girl?”
Like a girl.. you were insistent on that one. “You’d make a pretty girl, Leon. Would you like that?” You felt his cock jump under your touch, so close. “Yeah-Yeah..” He could hardly form a sentence. “Bet so.” You smiled. Your filthy words had him losing control, “I’m gonna cum, sis, you’re gonna make me cum. Don’t make me hold it in, I can’t,” He was blubbering into your neck, hot tears running down his face. “You better not cum, Leon. Don’t be bad.” You warned, a sharp bite to your words. It made it all the more terrible. The fact he couldn’t hold it in any longer.
“I’m sorry, ‘m so sorry. Big sister’s making me cum!” He choked out, hips humping frantically into your fist. He came all over your hand, warm and sticky. “Oh-Oh..” He panted, catching his breath. “I’m sorry, I’m so sorry, I couldn’t .. Didn’t mean to.” He buried his face in your neck, far too afraid to look at you. “I couldn’t hold it in it, sis.” He whimpered, his tears wetting your skin. “Felt too good.”
“Look at you.” You scoffed. “Came all over yourself. You’ve got no self control. No better than an animal chasing after its base instinct.” You gave his cock a couple lazy strokes, making him tremble. The overstimulation made him take a sharp breath, but he didn’t make any effort to stop you. “I’m sorry, sis. M’ sorry. I know I’m so pathetic.” He shook his head, his hair brushing your chin. You gripped him by his cheeks, smushing them as you forced his face up. “That’s right, Leon. You’re pathetic. I bet you’ve jerked off so much that you’ve ruined yourself for real girls.”
He gasped at your words, face wet with tears. “No, No.. promise I’ll do better next time.” He let that slip. Next time. He was already imagining a next time. “I wouldn’t bet on it.” You released his face and wiped his cum onto his shirt. “I’m gonna take a shower. Don’t wait up.”
“Wait,” Leon whined, reaching out for you. “Can I go with you? Please?” He grasped your hips, sliding his hands to the undersides of your breasts. “Get off, Leon!”You resisted to no avail. He wrapped his arms around your waist with a sigh. His cheek pressed to your tummy as he spoke. “Don’t go, not yet. Wanna stay with you.”
He tilted his head to look up at you, puppy dog eyes meeting a look of disgust. “Too bad. Quit stealing my panties while you’re at it.” You shoved him by the cheek. It hurt, but any pain from you was worth it. “Please?” He muffled, begging for a scrap of affection. Leon was acting like a clingy puppy. Or a stray cat. When you feed them, they always come back.
“Keep dreaming, baby bro.” You smacked him hard enough to make him yelp. He let go (with great remorse), and you turned your back on him. You kicked your bags out the way, heading to the bathroom without him. You left him alone, dick soft against his tummy, all sticky in your bedroom.
You were a cruel woman, but he loved every second of it.