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Though Maddy did not actually have a date that evening, she took a hot shower and made herself up like she was.
Looking in the mirror, Maddy’s mid-length, dirty-blonde hair was styled into luscious curls. A modest amount of dark mascara brought out her striking green eyes, and bright red lipstick accentuated her already fulsome lips. Maddy ran her hands down her body, feeling the smooth satin dress that hugged her slight body in all the right places. The red, V-neck dress showed off Maddy’s cleavage and had been her choice for prom night. Now it would be used to fake a date and tease her own brother. A slit in the leg allowed a tantalizing glimpse of Maddy’s bare leg. She wore no underwear, of course, her bare pussy left exposed.
In that moment, Maddy believed she might actually be sexier than Holly Anderson.
A jolt suddenly went through Maddy as she thought about the irritating cheer leader. Scrambling to navigate her phone, Maddy went into settings and turned off “Location Services.” I’m getting sloppy, Maddy thought. She should have done that as soon as she’d stolen the device. Still, Maddy doubted Holly Anderson had the brains to track down her stolen phone, if she even wanted to.
A buzz made Maddy check Holly’s messages.
Elliot: fuck i want to cum all over those tits so bad
Jealousy mixed with Maddy’s aching arousal in a delicious way. She took a deep breath as she stared at the text message. She just had to remember the look in Elliot’s eyes not twenty minutes ago when he’d looked ready to ravish his own sister on the couch. That feeling was still there… “Holly” might end up helping Maddy nurture it too… But first, fake-Holly had to gain Elliot’s trust. This would be the hardest part of the plan for Maddy, to see her brother get so worked up over such a loathsome bitch. A hot, pretty bitch, to be sure, but a bitch nonetheless.
Maddy just needed to pretend to be Holly long enough to use that position of power to turn Elliot’s sexual energy towards his sister. All the while Maddy teased her brother from afar. It can’t be that hard to act like that dumb bitch.
Down the hall, Maddy heard Elliot slam his bedroom door shut behind him. Feeling a little sexually frustrated, are we, bro?
Smiling, Maddy head back to her room and started fishing out a sex toy from her closet. She could already feel the arousal moistening her pussy as she imagined Elliot dealing with his own hardness in the very next room.
She pulled her favorite six-inch veiny dildo from the closet. Stepping quietly, she kneeled by the small hole in the wall she shared with Elliot.
Elliot was sitting in his computer chair with his pants around his ankles, his cock already at full mast as he stroked it with one hand and texted with another.
Holly’s phone buzzed.
Elliot: mmm i want my cock between those juicy tits
Maddy bit her lip, her pussy quivering as she imagined Elliot spraying his load over her own petite chest. Of course, he wouldn’t quite be able to fuck her breasts in the same way he could Holly’s breasts.
Holly: ill squeeze my fat titties around ur throbbing cock and use my mouth to suck on the tip
Using one hand to position the silicone cock beneath her wet cunt, Maddy speared herself on it with a muffled moan. It felt wrong, so wrong for Elliot to be getting off to the thought of a girl that wasn’t Maddy. But seeing him so worked up, knowing that it was at least in part because of her teasing session earlier, it filled Maddy with a desire she needed to satisfy. Maddy fired off another text.
Holly: i want to feel you thrusting between my tits, fuck my boobs until you cum baby
“Oh fuck yeah, Holly,” Maddy pressed her face against the peephole, watching Elliot moan unabashedly as she stroked his cock. “God, I need your perfect rack.”
“Mmmf.” Maddy stifled another moan as she rode her dildo. It slid into her wet pussy easily, her arousal coating the silicone in sticky lubricant. Shlick. Shlick. Shlick. She fucked herself against the dildo fervently, bucking her hips as the tip of the cock hit her most pleasurable places.
Because of her long, red dress, Maddy looked for all the world like a pretty young girl kneeling on the floor, the dildo embedded in her cunt completely concealed.
Elliot: fuck, this is what you’ve done to me Holly
Maddy’s eyes went wide as Elliot snapped a photo of his glistening cock and sent it off. She stared in awe as it appeared on her screen, bulging and slathered in pre-cum. It was an impressive picture, and Maddy’s pussy ached with desire as she imagined it was her brother’s cock, not a silicone dildo she was fucking. But no matter how much she tried to imagine, the dildo couldn’t touch her as deeply as she knew her brother’s cock would.
Holly: oh my god yeah. my pussy is so wet thinking about throating that magnificent cock.
The sickly sweet smell of Maddy’s own arousal was starting to drive her into a frenzy as she bounced up and down on the suction dildo, desperate to drive it deeper and deeper.
Elliot: ur turn
Maddy’s stomach dropped. Her turn to send a picture? Of course, Elliot would expect that after a dick pic, but…
Elliot: i wanna see that sexy rack
Maddy paused fucking herself, her dildo buried deep inside her. A pussy shot she could have plausibly passed off. But he specifically wanted a picture of Holly’s breasts… There was no way Maddy could fool Elliot with her own body.
Maddy contemplated refusing, but she needed Elliot to believe it was really Holly he was texted. She needed him to believe this was real so that when Maddy started to use Holly to manipulate Elliot it would actually work.
Elliot: C’mon, it’s only fair…
That’s when Maddy had an idea. Navigating to Holly’s phone screen, she selected a blue application icon and started scrolling through photos. Jackpot. Holly’s OnlyFans. Maddy’s pussy throbbed as she encountered post after post of Holly filming herself doing utterly depraved acts with various members of the high school football team. I knew she was a slut… I didn’t know she was a whore.
There. Maddy found the perfect picture. A not too revealing but definitively sexy picture of Holly’s boobs. She was leaning towards the camera, a bright bathing suit barely concealing her considerable assets. Her cleavage perfectly angled for a cock to thrust into it. Though her face was hidden, it was unmistakably Holly.
Maddy sent it off.
Holly: cum all over my fat tits bb. cum 4 meeee.
“Holy shit,” Elliot breathed audibly from the other room.
Maddy glued herself to the peephole as she watched Elliot hold the phone in front of his cock while he jerked himself off. In his mind, he was fucking Holly Anderson’s juicy tits. In Maddy’s mind, her brother was fucking her sopping wet cunt.
“Oh, oh, ohhhhhh,” Elliot groaned softly as he began thrusting into his tight fist. His fist sliding on and off his lubricated cock like a jackhammer.
On the other side of the wall, Maddy bounced harder than ever on her dildo.
Although some part of her always ached to be the one to make Elliot get hard, there was something deliciously taboo about catfishing her own brother. Maybe it was Holly’s tits getting him off, but it was still Maddy’s mind. The thought of it made Maddy want to cum.
Maddy didn’t take her eyes off her brother’s cock as it twitched and jerked, nearing its own orgasm. The sight of her brother was too much to bear. She thrust the dildo to the hilt inside of her, reveling the feeling of being filled as wave over wave of taboo pleasure rocked her body.
Panting for breath, Maddy didn’t let herself savor the post-orgasmic bliss for long. A peep through the hole confirmed that Elliot was nearing completion, his hips thrusting harder than ever, his eyes glued to Holly’s tits on the phone screen.
Acting quick, Maddy removed the dildo, smoothed out her red dress, and headed out into the hallway connecting their bedrooms.
KNOCK. KNOCK. KNOCK.
Maddy banged loudly on her brother’s bedroom door.
“Fuck,” Elliot’s muffled curse sounded from the other side of the door. Maddy smiled. At least he wasn’t going to cum to Holly Anderson yet.
A minute later, Elliot answered the door with a disgruntled look. His hair was standing at odd angles, his eyes were still filled with a cloudy film of lust, and there was a bulge where his blue-balled cock had been unceremoniously stuffed back inside his jeans.
“What do you-” Elliot cut himself off mid-sentence as he took in his sister’s appearance. “Oh, fuck.”
Maddy inwardly smiled as her brother’s gaze roamed down her body, taking in the sweet curve of her ass, the deep V of the red dress where her cleavage was most visible. Maddy pursed her lips, hoping she could get her brother to think about those red lips wrapped around his suffering cock.
“Uh, I mean,” Elliot cleared his throat. “You look good, sis.”
“Oh, thanks!” Maddy blushed. “I just wanted to let you know I won’t be back home ’til late. So, don’t wait up or anything.” Maddy crossed her hands beneath her breasts, pushing them up ever so slightly.
Elliot’s throat bobbed. Maddy swore his cock twitched in his pants too. This was just torture for him.
“Uh, okay. I hope you have a good date,” Elliot said. Maddy smiled at her brother and waved goodbye, swaying her hips as she walked away to allow Elliot to see how the red satin hugged her ass.
It wasn’t until Maddy had made it down the stairs that Maddy heard her brother’s bedroom door close again.
Without hesitation, Maddy shot off another text from Holly’s phone.
Holly: so this is fun and all, but do u have any rlly dirty kinks?? 😉
As Maddy didn’t actually have a date to go on, she walked to the nearby roadside diner, ordered the house special chocolate sundae, and settled into a dimly lit booth in the corner. Made up in heavy mascara and wearing a revealing satin dress, Maddy looked like the world’s classiest hooker while she covertly sexted with her brother.
The server certainly gave her an odd look at her choice of attire and makeup, but didn’t say anything, perhaps because any girl who looked that gorgeous and who was alone at a hole-in-the-wall diner had probably just had her heart broken.
But contrary to what one might assume about her, Maddy was having the time of her life. She wore no panties, her cunt leaking its juices through her dress and all over the seat. She found herself squirming, clenching her thighs together as she yearned for another orgasm like the one she’d just had while watching her brother masturbate. Maddy let a spoonful of ice cream dissolve in her mouth, imagining it was actually the head of Elliot’s cock resting on her wet tongue.
Elliot: wdym by kinks
Maddy rolled her eyes as she tapped away at Holly’s phone screen.
Holly: yknow… taboo stuff. shit like gangbangs or bondage or incest porn.
Maddy clenched her thighs together again in an attempt to covertly stimulate her wet pussy. But it just caused the mound between her legs to ache harder. On this Saturday night, even a fairly rundown diner was full of chattering families. The bad part of this plan was that Maddy had been forced to leave the house. She no longer had the privacy needed to fuck herself with wild abandon.
After what seemed like an achingly long minute, Elliot finally responded.
Elliot: no not really
Maddy could not have rolled her eyes harder. If a hot girl asks you if you have any kinks, you play along, you dumbass. She sighed as she contemplated how to play her next few text messages to hit just the right notes.
Holly: oh come ooooonnn! istg every guy is into SOMETHING these days.
Maddy was proud of herself for waiting another full minute before sending off a double text.
Holly: ok maybe i can guess. it’s gotta be somethin rlly depraved if u wont tell me
Elliot: i like doggystyle
Maddy raised an eyebrow and made a mental note of that for later.
Holly: hot. but that’s a position, not a kink.
Elliot: shrug
Holly: r u into like rlly abusive stuff? hitting and slapping and shit?
Elliot: eh
Holly: hm not a no but not a yes. Ok how about something rlly gross like piss play? does piss get u hard u dirty boy?
Elliot: lol no not at all
Holly: hmmmmm
Maddy let Elliot hang for a little while longer as she enjoyed her ice cream, the cold feeling of it slipping down her throat contrasting with the fiery warmth now spreading rapidly from her cunt.
Holly: let’s see… it’s not like you wanna fuck ur mom or something, is it?
A full two minutes elapsed before Elliot’s response.
Elliot: lol omg what don’t be gross that’s crazy lmao
Maddy grinned. Gotcha, bro.
Holly: OMG i struck a nerve.
Elliot: no u didn’t!
Holly: I sooooo did. u wanna fuck ur own mom??
Elliot: I’m not attracted to my mom, Holly.
Holly: oh ur serious…
Holly: omg… is it ur sister??
Maddy waited a full five minutes for a response. Nothing came.
Holly: OMG IT TOTES IS
Elliot: what???
Holly: ur NOT EVEN DENYING IT
Maddy practically pumped her fist in the air, alone in the diner. A middle-aged man in the booth beside hers gave her a weird look. Elliot was trapped, and Maddy rejoiced.
Holly: i guess she’s a pretty little thing. nice ass. bet she’d be a good fuck too.
Elliot: stop being gross!
Holly: don’t worryyy. im an open minded girlie. i actually think it’s kinda hot
Maddy was breathing heavily as she got more and more excited, leaning forward in her seat as she thought of just the right words to trigger Elliot. She had to play this absolutely perfectly.
Holly: u can tell me. do u think maddy is hot?
Elliot: i guess Maddy is kinda hot idk
Arousal flooded through Maddy’s body like a tsunami. She stared at those words, that admission, as her fingers gently trailed to the leg slit, under her dress, slid across her thigh, and started massaging the wet folds of her pussy. She had known it already, but this text was another level of open admission. Elliot wanted her.
With one hand, Maddy texted a response, while her other was busy stroking the folds of her labia teasingly.
Holly: I KNEW IT. omg do u masturbate thinking ab her?
Elliot: maybe once…
Holly: you dirty fuck
Holly: i bet she’s such a tease to live with
Elliot: u don’t even know…
Holly: mmm i hope u fucked her nice and hard after my party. she looked so slutty in that black dress
Elliot: she’d never go for that
Maddy’s middle finger slid into her already spasming cunt-hole. Somehow, her orgasm earlier had only made the ache in her loins increase. Something about Elliot finally coming clean about his attraction to his own sister made Maddy want to fuck herself silly.
Holly: so u haven’t fucked ur sister yet??
Elliot: no. it’s just a fantasy. besides, it’s wrong. and she’s too innocent to think about her brother that way anyway.
Elliot’s “too innocent” sister currently had three fingers shoved in her cunt as she fucked herself in the back of a shitty diner.
Holly: mmm. the thought of this is turning me on lol. it’s so taboo. tell me what u like to fantasize ab?
Elliot: i think about her wearing that sexy schoolgirl outfit while she rides my big, fat cock with that perfect virgin pussy
Maddy gasped as she read Elliot’s text, the vision of her pussy lips gripping around her brother’s cock filling her with deliciously sweet desire. She slowly lifted herself up and down off her fingers, bobbing imperceptibly in the booth. To anyone else in the restaurant, she just looked like a lonesome girl staring at a phone, shifting in her seat awkwardly.
Elliot: her ass is so tight. almost as perfect as ur rack.
Maddy frowned at this, shooting off a response she deemed as in character for Holly.
Holly: nothing is as perfect as these tits, bb
Holly: i bet she wants u 2. i bet she dreams of that thick cock pumping her virgin pussy full of sweet cum.
Elliot: u r seriously cool with this?
Holly: cool with it? elliot im getting off to this. im a fucking slut lol u know this
Based on the contents of Holly’s phone, Maddy decided this probably wasn’t too far off from the truth.
Holly: keep going… im getting close!
Elliot: i dream about fucking my sister from behind
“Mmmm!” Maddy tried to pretend she was really enjoying the last dregs of her ice cream to cover for the sexual moan she’d involuntarily let escape. The fantasy of her brother entering her pussy from behind, forcing his cock inside her… It made her whole body shiver.
Holly: oh yeah?? tell me how u want to fuck her
Elliot: i wanna throw her on the couch, grab her sexy little ass and use it to fuck her deeper than she’s ever been fucked before.
Maddy was absolutely drenched. Later that night, some poor janitor or waiter was going to have to clean up the absolute mess of arousal that currently covered the booth. She bounced up and down on her hand a little harder now, not caring so much if anyone saw her. Maddy was just too eager to fuck herself deeper and deeper as she pictured Elliot manhandling her, flipping up her skirt, and reaming her pretty little cunt. She wanted her brother to have his way with her.
Holly: omg don’t stop im so close
Maddy was so close to the edge now. She just needed a little more.
Elliot: then im gonna use those sexy pigtails of hers to ream her even harder. Im gonna fuck her so hard she’ll be screaming my name.
Elliot: then i wanna flip her over and fuck her in the pussy while i look into those sexy green eyes. i wanna fill her up with my cum so she knows she’s…
