The Great Blackmail – Brother sex with Sister

The Great Blackmail – Brother sex with Sister

“Are you a virgin?”

I tare my eyes from the screen of my Mac to see my little sister, Maddie, standing at the foot of my room, blank eyed, looking back at me, and I sigh hard. Now it’s important to understand that Maddie and I have an understanding when it comes to each other. She doesn’t come into my room and I don’t come into her room, so this sudden intrusion was a surprise to me. It’s not as callous as it sounds though, we just don’t get along. She was born when I was seven, so either I was early or she was too damn late. A brother I could probably have handled, but when you’re seven and all of a sudden fucking Princesses and shit start popping up all over the goddamn place, it can piss you off.

And it’s not that I’m introverted either, I just like my own space. Space, which the luxury of a little sister does not permit. So we decided on the rules early on and we got on with it. I didn’t know her, and she didn’t know me. We kept ourselves to ourselves, and we only interacted when we had to, like at family gatherings, Christmas, and when our parents made me the designated taxi driver.

“What?” I ask, taking my headphones out. “Can’t you sleep?”

She’s in a thin nightgown that is about two sizes too fucking small and her long blond hair is in a rushed ponytail. Maddie is now well and truly past the Princess nightgown phase, and she looks utterly ridiculous right now. I take a drink from the beer on the table next to my bed. I’d been writing all afternoon and my head hurt, so perhaps her distraction had come at a good time. I was getting tired anyway.

“Are you a virgin?” she asks again, and I splutter through my mouthful. No, I’m not a virgin, thank you very much, I think in my head. Followed by: Did she just fucking ask me that?

Jesus, I really was tired. “I didn’t hear you,” I say and she smiles.

“Yes you did.”

I know smiles. And I know girls’ smiles. This was no innocent sisterly smile. This was a completely different fucking smile, slightly innocent, but with some seriously sinister undertones.

“That’s none of your business,” I scowl. “Now go back to bed before I get Mom up here for you bothering me.”

“Mom and Dad are out for the night.”

Great, nice of them to mention. Then I thought that perhaps they had, maybe I just wasn’t listening. It wouldn’t be the first time I’d gone downstairs to find the place vacant.

“Why do you want to know?” I then ask.

“So you have. What’s it like?”

“It’s different for boys than it is for girls.”

“What’s it like for boys?”

If she got anymore excited I could have sworn her eyes would pop out of her head or something. She was practically bouncing in the doorway. I find myself stuttering now, and I can feel my cheeks starting to go a little red. This was not a conversation I was prepared to have with my little sister.

“Fine. Yeah, it’s good. Now go away, Maddie, I’m trying to work.”

“I want to try it with a boy,” she says, matter-of-factly and I just look at her. If my mouth could hit the floor like it does in those Cartoons she always watched (or used to watch. Whatever, I don’t even care what she watches) then it probably would.

“Well you better not tell me the little fuckers name or else I’ll kill him.”


I scoff so hard she flinches. “Fuck right off, kid,” I say.

“I’m not a goddamn kid, Charlie,” she says and I scowl at her. She stares at me, blank eyed, again and then says something so matter-of-factly, so nonchalantly that I actually thought for a moment that I was dreaming. You know when you hear something so absurd, so ridiculous, and so beyond belief that you have to do a double take? That it takes just that little bit longer to sink in? That is the sort of shit I was dealing with. “Anyway, it’s you,” was her answer, and I laughed so hard that for a second I didn’t think I was ever going to stop, like I was going to laugh until my insides exploded. “You’re the boy.”

I mean, kudos to the way she played the situation. It was something she clearly had been planning for some time. About a million things run through my mouth at the same time and a verbal shit stream of nonsense spews out. In the end I just look at her and say; “Me brother. You sister. That is wrong on every level. We’ll never speak of this again. You’re insane. Goodnight.”

I grab my headphones, still laughing to myself when she pulls out another blockbuster of a comment. “If you don’t then I’ll tell Mom about that stash of weed under your bed, and I’ll tell Dad about that porn stash you hide in your bottom drawer. And you’ll lose your car and your allowance and you know it.”

This time my jaw does hit the floor. Touchdown, Maddie.


I stare at her in amazement for what feels like an age until Maddie glares at me, hands on her hips. “Well?”

I was still trying to wrap my head around the idea that my sister was trying to blackmail her older brother into having sex with her. Where the fuck did that warped, absurdly crafted pan of insanity come from? I’ll also clear up the two points Maddie raised. 1) The weed is medicinal, naturally. (And providing that bullshit doesn’t wash, I’m not going to justify it to anyone. I’m not a fucking kid. I like what I like. Who doesn’t like a joint every now and then? And it helps with the writing) 2) As for the porn … who doesn’t?

“Well what?”

“I want a boy to have sex with me, Charlie, and I want it to be you.”

“No!” I yell at her. “It’s crazy. It’s insane. It’s illegal. It’s sick. It’s wrong. Do you need me to fucking continue? I’m your fucking brother, Maddie, for fuck’s sake. It’s incest.”

“So?” she retorts. “Brothers and sisters often experiment with each other. It’s natural. I’m a girl, you’re a boy. Brother–sister incest is actually considered to be widespread but rarely reported, you know.” So many questions were running through my head right now. This crazy bitch had even Googled it, for fuck’s sake.

“That doesn’t fucking mean we’re going to,” I say back.

“Don’t you think I’m pretty?” she asks and I swallow, hard. A simple response. She isn’t leaving here without getting what she wants, I say in my head. I’d never even looked at my sister as another human being before this moment. I’d just considered her an annoying little fucker that lived in the room at the end of my corridor, and now I was looking at her the way no brother should ever look at his sister. “Well,” she presses, “don’t you?”

“Aahhh,” I stutter as I look on at this little blond bombshell. Maddie is beautiful, I concede as I look past the prejudice of being an older brother. She’s small and petite and delicate, like a flower. She has big caerulean blue eyes and she is lightly freckled across her now blushing cheeks as she realises I am actually looking at her. She just aches with natural beauty. She is actually one of the most beautiful girls I’ve ever seen (not that I’ll ever tell her that). The nightgown she dons is a little tight, and it accentuates the curves on her young, nubile body. Her breasts are small, no more than pre-pubescent buds but what did I expect? “Yeah, I think you’re pretty,” I say. “Real pretty.”

She blushes some more. My mouth feels dry and I reach for the can and take a generous mouthful. I’m starting to think about her now, and I feel myself growing a little. This is so fucked up, I keep telling myself. This is fucking insane. “I think you’re pretty too,” she says. “I see you coming out of the bathroom sometimes, I’ve seen your body. I think about it sometimes and I know we never speak to each other but you’re my big brother and I love you.”

She’s moving into my room now, staring me down with those big blue eyes and I find myself paralyzed, unable to move. Did she actually just say she thinks about me sometimes? She reaches the foot of the bed and jumps up onto it, kneeling her way towards me like some fucked up nympho. “Do you love me?” she asks.

I swallow hard and take another long drink. “Of course,” I stutter.

She’s inches away from me, now, and she pulls up her nightgown, flashing me the bottom of her floral print panties. “And you think I’m pretty, right?” The nightgown goes higher, showing off her taut stomach forged from years of ballet and gym class.

I gulp. “Yeah.”

Her hand starts to graze across her stomach, and then it slips into her panties and she moans silently and she brings it out a moment later.
She moves again, so that she’s straddling one of my legs. I can feel her breath on my face. She pushes me back and then leans over me, our lips almost touching and she puts her finger into my mouth. “Do you want me?” she asked in a husky whisper, as I taste the bitter juice on her fingertip.

“Yes,” I whisper back before I can even think about the question and her lips curl into a satisfied smile.

“Then take me,” she says, “because I want you too.”

It’s lunacy, I think as our lips meet, sending jolts of electricity through both of our bodies. It’s insane. And then I find that I’m kissing her back, my sister, my own flesh and blood, and what’s worse is that I’m enjoying it. She must have been practicing on the boys at school because boy can this girl kiss! She puts everything into it, kissing me hard. Our lips lock and battle like professional lovers, as she dances those soft, baby-faced lips across mine with such precision. And then her tongue is at the door, breaking into my mouth and dancing around with my tongue, overlapping and caressing and fighting. My hands start to roam, up the softness of her legs to her sides, and then I’m pushing the nightgown up and my hands are on her panty-clad bubble butt. It’s firm and tight and she responds to my squeezes.

She breaks away and looks into my eyes. “I promise not to tell if you don’t,” she says.

“It’s blackmail,” I say back, although less adamant as I was before.

“But you want me,” she says, biting her bottom lip. God, it drives me crazy when she does that. She knows what she’s doing. “Remember?”

“Still blackmail,” I manage to say and she leans in and she’s biting my bottom lip now.

“But you’re the one with your hands on my ass,” she whispers in my ear.

I look at her, into those incredible eyes that I’ve never before noticed, and then I’m smiling too and I give her a playful squeeze. “You are a hundred and eighteen pounds of pure evil,” I say.

“Bite me!” she says. She’s still leaning over me and it’s a fucking absurd situation to be in.

“Fuck this,” I say in a hoarse whisper and I flip her clean over, so that I’m on top and she’s the one squirming underneath. I use my body to keep her down, and she giggles and moves her legs so my pelvis is resting on hers between her legs. “Better!” I say.

“You like to be on top, huh?” and I just raise my eyebrows at her.

“So what now?” she continues.

“Now you’re going to tell me what this is really about.”

“I don’t know what you mean,” she laughs.

“Oh, come on. You’re not six. You’re not fucking stupid. Why are you doing this?”

She looks at me for a few beats. “Leah has had sex,” she says. “And Chloe and Tanya. They’ve both been with Bobbie, but he’s …” she trails off.

Those girls are part of Maddie’s stupid ‘cool girl’ clique at school. Jesus, when I was her age I was thinking about cartoons and sports and shit, not girls and sex. “Go on,” I push.

“He’s stupid,” she says. “And he doesn’t have a body like you do. He’s not as attractive as you and…”

I fucking hate it when she breaks off mid-sentence. I frown at her. “Go on,” I say again.

“… and they all talk about how hot you are and about they want you and how I’m not allowed because I’m your sister, so I want to prove them wrong.”

“Seriously,” I say, my frown deepening. “You want to blackmail me into having sex with you because your slut friends have and because you think they’d try and make a move on me.”

Her silence is as good as an agreement. “You’re deluded,” I continue. “I prefer girls my own age, hell, I don’t even prefer them. I prefer older girls, let’s say. They’re more mature and more… anyway, that’s not the point. You have nothing to worry about. I have no intention of fucking your friends, and incidentally, ruining my fucking life in the process so please…” I motion for the door. “… get the fuck out.”

I look back at Maddie to find her laughing. “I don’t want to have sex with you because I’m jealous,” she says and I ask her what he reason is then. “I want to have sex with you because you are really hot. And besides, if you really didn’t want me then you wouldn’t still be on top of me, on your bed, with your crotch on mine. I know that’s not your phone, Charlie.” She starts biting her lip again and I feel the burning member in my pants growing again.

“So fuck me, Charlie,” she says, “Or I’ll tell Dad you touched me.” She has that evil look on her face again and I scowl at her. She’s easily the smartest girl in the fucking State, she knows how to get what she wants.

“You wouldn’t,” I say, leaning closer to her.

“I really would,” she says, and I bring my lips to hers again. As we kiss I feel Maddie forcing her hips up, rubbing her panties against my jeaned-crotch and she must have hit her clitoris because she moans into my mouth and her body trembles.

“You like that, huh?” I say, taking my hand and slowly tracing it up her leg.

“Mmmhuh,” she coos, as I dance over her inner thighs. I feel her shiver at the touch.

“And what about this,” I say, as my hand reaches the fabric of her panties and I graze my fingers across her crotch. My heart thumps in my chest. This is so wrong I can’t even comprehend it. I’d never had incestuous thoughts before, but seeing Maddie at my mercy was turning me on. She inhales deeply as my fingers move over her clit and up to her bean. Her panties are drenched; the wet patch at the bottom of her slit is growing and growing.

“Yeah,” she says, as I rub her cunt from the outside. Her breathing is shot to fuck now as I circle and flick her through the material, her wet patch becoming darker and darker, growing and growing with each flick and each caress. She moans and coos at my touch, a soft, innocent sound that is just so beautiful, and she continues this cacophony of verbal pleasure until her body convulses and she shudders and cries out in orgasm. “Fuuuuuuuuck.”

I don’t know whether it is the sound of her orgasm, or the sound of her swearing, that turns me on so much, but I’m suddenly rock hard to the point of pain and my lips find hers and our tongues are battling again, this time rough and hard. Her body quivering at my touch was one of the most amazing moment’s I’d ever experienced, and now all I can think about is freeing the caged beast and pounding the fuck out of Maddie’s cunt. “Oh my God,” she says, breathless, “that was fucking amazing.”

“God sis, you’re absolutely drenched,” I laugh, referring to her panties, which were now two shades darker than they were meant to be. It looks like she has pissed herself.

“Whose fault is that?” she laughs, pulling me in for another hot embrace. She breaks off and stares at me with those eyes again. She bites her lip. “I need you in me, Charlie, so bad.”

“So bad?” I mock. I want her so bad too.

“So bad,” she repeats, clawing at my top and forcing it up over my head. Her hands come back down, running over my body and I thought for a moment she was going to cum for a second time, just by looking at it. I’m not a bodybuilder or a gym-freak or anything like that, but I’m not a fucking slob either and I keep in shape. As a result my body is pretty neat. I run quite a lot because it helps with the mental block being a writer brings, and to be a better runner you’ve got to work on body strength. It’s an hour or two hours a day where you can just be, not thinking about anything in particular. It’s relaxing, seriously. Try it.

Tee shirt now discarded on the floor, I feel the cold of the air on my skin and it feels great. I can hear Maddie’s heart pounding in her chest and I’m sure she can hear mine. We’re kissing again, and her hands explore my body for the first time. I push up her nightgown and move down her body, planting soft, warm kisses across the taut surface of her navel and she shudders again. I can smell the musk of her cunt and it sends me into overload, so sweet and intense. I’ve been with virgins before, but this smells like the sweetest cunt of them all. I can smell her juices as she continues to drench through her panties. Maybe because the cunt in question is that of my little sister and it’s the most dangerous, most taboo of pussies.

All I’m thinking about now is tasting her again, suddenly her finger in my mouth isn’t enough. I need more. I pull her nightgown up and over her head, and no sooner is it on the floor with my tee is Maddie riving at my belt, damn near ripping the thing off as she forces my jeans down and off until we’re there, facing each other on my bed, in just our underwear. Maddie isn’t wearing a bra, and I see her little buds up close. They’re hardly anything, just two perky pink nipples on her chest. She has Goosebumps on her skin, and we’re breathing heavy as we look at each other’s bodies in the sunset light for the first time. She opens her mouth to speak, but I think fuck it and the animalistic passion within me takes over and I grab her and pull her into me, forcing my lips on hers like some wild beast. She squeals in delight and our tongues do battle again. I’m ready to just fuck her as we are, kneeling up. I’ll just grab her and impale her on my shaft and ride her like there’s no tomorrow.

Somehow I manage to fight off that urge and instead I move my hand down her back and under her panties, onto her naked ass. She moans into me again as I move around to her blond mound, not much garnished with hair, and the steaming wetness that greats me. I start to stimulate her clit again with my finger, and she moans louder than ever. Then I’m tracing the wetness between her lips all the way down her engorged slit to the fiery pits of her virgin tunnel. Her hand clamps down on mine and then she starts forcing my middle finger deep into her cunt, and she screams out as I explore her for the first time. God, she’s so fucking tight. It feels like her walls are going to break my finger. I slip my finger in and out a few times to loosen her up, and then I go back to her clitoris. Her body trembles, and glistens with sweat. She breathes hard.

I push her back onto the bed and pull off her panties so that she’s fully nude and at my mercy and I admire at her nude body for a couple of beats. The blond patch on her mons pubis glistens with sweat and juices. And then I went for it, driving my tongue deep between her legs and I start lapping up that virgin pussy juice. She sequels and moans and her hand comes through my hair, behind my head, pushing me into her. Her hips come up to meet my lips as they flick and tickle her hole, moving up her slit to her clitoris, and she moans hard as my finger joins in the action, slipping in and out of her until she climaxes for a second time, her hands grabbing and grasping at my bedsheets.

“I can’t take anymore,” she yells. “I need you.”

“I need you first,” I say and she purses her lips at me. “You’re too tight yet. I think you need to lube me up,” I wink, and she gets the message. She springs up and grabs my boxers, pulling them down and allowing my raging boner to be free. I’m a modest seven inches by two inches, and she looks at me in horror as it springs out in front of her.

“It’s massive, that won’t…” she goes to say, and then her shocked expression turns into a burning, lustful desire and she takes me in her hand for the first time and I have to concentrate hard not to blow right there and then. She bites her lip as she starts to stroke my shaft, weighing it up, and then she pulls her blond hair into a tight ponytail and she goes for the plunge, taking my tip in her mouth.

It’s so warm in there, and I lean my head back and groan as she starts to bob up and down on my throbbing member. It’s obvious she’s never had a dick before, because she tries to take it all and gags hard, very nearly throwing up all over the fucking place.

“Take it easy,” I say. “You OK?”

She bites her lip again and nods. “I didn’t expect…” she goes to say, but stops herself and she takes my dick again, spitting on the tip and slobbering on my shaft as she lubes it up. “Fuck me,” I groan as my little sister bobs on my dick. “This is amazing, Maddie.” That gives her confidence and she takes a little more, pumping harder and sucking deeper as the pressure in my balls starts to build. She laps up my pre-cum, swallowing the salty liquid like a professional.

“Stop,”I say as I’m about to blow. “I’m gonna cum.”

She brings her lips to mine, and I can taste the saltiness on her tongue. “Not yet,” she winks, laying back and opening her legs for me. “That’s for later.”

My bellend burns with desire for her cunt now, and I look around for my wallet. “You seen my wallet?” I ask her. “I need a rubber.”

She pulls me towards her and kisses me hard again, my dick touching her virgin cunt for the first time. I can feel the heat coming off of her. “I want to feel you cum in me, Charlie,” she says.

“You crazy? What if you get pregnant?”

“I’ll risk it if you will,” she giggles, pulling me towards her again and that only turns me on more. I’d never fucked a girl without a rubber before, I’d never actually come inside a girl without that barrier between us.

“Are you sure?” I ask her, knowing the answer full well.

She nods, playfully, taking the tip of my dick in her hand and guiding it towards her steaming entrance. “Now fuck me, Charlie, fuck me like you fuck those other girls.”

Maddie was already so wet, and the added lubrication her saliva had put on my dick allowed it to easily spread her lips and force its way an inch into her virgin cunt. She screams out as I penetrate her with my dick for the first time, and I can feel her walls stretching around my intrusion as she acclimatises her tight cunt to my member. She moans and exhales hard, and I lean in and kiss her to take her mind of what was about to come.

I edge myself out and then force myself in a bit more, and she bites down on her lip and moans out as I force another few inches into her love tunnel. And then I hit the barrier of her innocence, and I stopped at the entrance to the promise land.

“Last chance?” I say to her, wickedly. “Blackmail never ends well.”

She grabs me and forces her lips onto mine again. “I want you,” she says. “Do it. Make me yours.”

I inch back again and then I thrust forward, through her virginity as Maddie cries out in perpetual agony, letting out a blood-curdling cry as her cherry pops, and I force all of myself into her until our pubic hair tangles and our pelvises touch, with me buried deep into her cervix. She arches her back up into mine and her nails dig deep into my back as tears fall from her face, staining her skin and I wipe them away and kiss her.

“Relax,” I tell her. “The pain will go after a while. You just need to get used to it.”

“I know,” she whispers. “Chloe told me. It feels amazing,” she says. “God, I love you.”

“I love you, Maddie,” I hear myself say as I’m balls deep in my sister, and now we’re making out, her body morphed into mine and my seven inch dick buried deep into my sisters cervix as the sloppy sound of our kissing fills the room, her lips battling mine, tongues making love and saliva swapping in our mouths. And then I start to thrust, in and out; the gentle sloppy sound of my dick slipping in and out of her tight, wet pussy is joined by Maddie’s bodily moans as my balls slap against her ass with each long thrust and as she relaxes, her hips undulating and her body accepting my girth and moving in synch with my own, we start the forbidden dance of life as the gentiles of two siblings meet and join and make passionate love in the most taboo of circumstances. As we taste the forbidden fruit, knowing full well that a brother and sister should never be this intimate with each other, our passion intensifies and we moan with each other.

“Oh, Charlie. Charlie, this feels so good. Oh, Charlie. Charlie it hurts. Charlie, oh, Charlie it hurts.”

She screams so loud as I pound her tight, virgin snatch that my ear drums threaten to bust and for once I’m glad we live in a semi-detached with no neighbours just a wall away. I’ve never heard someone make so much noise. She’s crying hard, but when I ask her if she wants me to stop she tells me “no way, no fucking way,” and grabs my ass and forces my thrust into her again, deeper and harder. The guttural screams and moans that are coming out of Maddie’s mouth, and the fact she’s trying to carve the skin off my fucking back, tells me that I was pounding this girl so hard it probably felt like she was being torn apart from the inside, and the fact her cunt has already contracted around my dick twice in orgasm tells me she’s fucking loving it. She’s definitely the youngest I’ve ever been with, but it feels fucking amazing. Maybe it’s because this is so wrong, and yet so right. She pulls me towards her and we start making out, her teeth biting down on my lip again as I feel my own climax building in my balls and I cry out too when it becomes too much, and I feel myself firing stream after stream of my seed deep into my sisters womb and she cums one more time before I collapse next to her, breathless and drained, as the scent of our love-making fills the room.
“That was amazing,” I say, as I try and regain my breath.

“That was so wrong,” she says, as my cum starts to trickle down her inner thighs. “But so fucking hot. That was incredible, Charlie.” She turns to face me, and we kiss a gentle, lingering kiss. She grabs my can from the side and takes a sip, and then a longer drink, and she hands it to me.

“Do you have any joints?” she asks suddenly and I look at her, stunned.


“Relax,” she says. “I’ve tired them before at Kodie’s. Her brother has a stash too.”

I look at her blankly. “Well, do you?”

It’s ridiculous. Ten minutes later I’m led there, naked on my bed with my fucking sister, my cum in her stomach and her virginity blood on the tip of my cock, evidence of her defloration, smoking weed and drinking beer and laughing. We talk for what feels like hours, getting to know each other better than anyone else, talking about everything and anything and I start to realise that, you know what, Maddie is pretty fucking awesome.

“I’m sorry I blackmailed you,” she laughs and I look at her through the light haze of smoke, haphazardly. Then I kiss her, and trace the delicate frame of her body with my finger, coming to rest on the soft skin of her side.

“Don’t,” I say. “I’m so fucking glad you did.”

“You don’t hate me?” She says. “I practically forced my brother to have sex with me. I think I raped you,” she laughs, and I laugh too.

“Nah,” I say. “You know what, you’re the best girl I’ve ever been with.”

She frowns. “Let’s be honest, I’m a fucked up little slut, right? Nothing more.”

“No.” I say. “You’re my fucked up little slut,” and she laughs hard, playfully hitting me in the chest and I kiss her again. Those eyes captivate me. I go to her neck, nibbling and biting. And then I flip her onto her side, my dick hard again, and when she feels my flesh prodding her in the back she opens her legs and I impale her and she screams out in ecstasy. “And now it’s my turn to be in control.”

It only takes five minutes until she’s at orgasm, and I’m filling her hot cunt with my sperm for a second time. And after what’s left of my beer, and half of another joint, she gets up, gathers her clothes and heads for the door. It must hurt because she walks like she’s just shit herself. She turns when she reaches the door. “I’ll keep a hold of the stash for a while,” she says with a wink. “There’s still more stuff we haven’t tired yet,” and then she’s gone and I drift off into a satisfied sleep and for the first time in my life I dream of my sister, and it’s great.


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