Ross Culkin, Male, Dream partner is bitch-sister sex-addict

Ross Culkin thought it was very odd that he’d gotten such a bizarre (and frankly, kind of insulting) email. But then again, scams came in all shapes and forms these days. You had to be careful, cagey, cunning, smart. People who spent a lot of time surfing the internet like him obviously had that cunning. Ross smirked at himself as he prepared to delete this latest email. Then he paused as he reflected.

Fuck, he was lonely. And horny.

Pursing his lips as he reconsidered the ‘offer’ being made in the email, the eighteen year old stared at the screen, finger poised on his mouse. He’d done a full scan of his computer and checked the programs for anything suspicious as well as the downloads. Beyond the usual suspects, his computer was clean. Every time. Scannng this latest email, he was almost dissapointed that it came back as all clear for the link and attachments. Hovering his mouse over the link included, it showed it was going to the place it promised. Maybe he was just being paranoid.

The scrawny, bland young man jumped as his ajar door flew open. “Hey creep!” a shout greeted him as his new guest burst in with a malicious smile, quickly scanning him with her eyes. Her grin diminished and she returned to her usual resting bitch face of indifference when she didn’t find anything new to mock. “Ugh, did I miss you watching porn?”

Ross’ computer was next to his window facing the parking lot of the apartment complex and with his back to the door, anyone who came in could easily see what he was doing online. After the first time his sister Cherry barged into his room and he had to rush to close his pants, he learned to lock his door. Of course, being the bitch of an older sibling she was, she decided a locked door was a perfect excuse to knock loudly on his door at random times and demand his attention. If he didn’t answer fast enough (and even when he did) she proceeded to mock him for jerking off. Even when he wasn’t doing anything and just wanted some peace and quiet. He’d resigned himself to keeping his door open or ajar when she was around and limiting his porn surfing to late at night or when she was gone.

“Why, did you want to watch with me next time?” he snarked back quietly.

Cherry’s expression shifted from indifference to a wide-eyed irritation. She hated being talked back to or contradicted. Especially by anyone with a Y-chromosome. She stalked towards him with a glare and he instinctively flinched. The sibling roommates were almost total opposites. He was dark haired, short, pasty and ‘meh’ in looks and personality. She was taller, fitter, hot as Georgia asphalt and could charm the spots off a leopard when she wanted something from someone. Plus, being the older sibling and their parents’ favorite meant she knew she’d at worst get a slap on the wrist so their parents could call themselves ‘fair’ when there was a conflict between the siblings.

Needless to say, their relationship was more she got and did what she wanted and if he was lucky, he got left alone. He’d only agreed to move out with her into their own apartment because he’d wanted out of their parents’ place and even having her for a roommate was better than having three people he had to live with. Now he just had one person to deal with. In practice, however, it was more like he always payed the bulk of the rent, when she could be bothered to pay anything and served as a separate wallet for her when her modeling and sugar daddy money ran out. She tended to use dates with ‘boyfriends’ to get food and stuff she wanted and then conveniently move on to another guy when she got bored or found a better deal. Needless to say, with her hotness and persona, she was never short of admirers.

Ross had stopped keeping count of times his sister had kicked him out of their apartment because she was expecting company or bringing someone home. It didn’t matter if it was two in the morning and he had to work in the morning or if he’d just ended his shift. She told him she needed the place to herself and he had to make himself scarce. Given his lack of friends or extra funds, he usually wound up sleeping in his SUV.

Now, Cherry loomed over him for a few seconds in silent anger and then leaned in to grab the front of his shirt and hiss directly into his face. He instictively flinched, conditioned from countless previous bullying sessions with her. “Listen you creepy, disgusting jackass, you’re lucky I even let you live here.” Considering he was paying the full rent at least 90% of the time, that was false, but he knew better than to argue right now. “Dad and Mom would have you kicked out in a heartbeat if I said something and I have a contact list of guys and girls who would happily call every dude they know to come and kick your ass. So fucking watch it!” she snarled at him.

He mumbled his acquiesence. “What was that?!” she almost shouted, gripping his shirt front tighter.

“I said, fine, I’m sorry.” Ross gritted out.

“You don’t sound sorry. That didn’t sound like a proper apology.” she replied with sugary malice.

He closed his eyes and tried not to cry with pure frustration. He was useless in a fight and knew he couldn’t afford it if their parents called the landlord. Doing his absolute best to steady his tone and sound as submissive as possible, he couldn’t help his voice hinting at tears “I’m sorry Cherry. I won’t speak back to you again.”

Ever the heartless bitch, his sister leapt on his weakness and delighted in rubbing salt in the wound. Speaking with false tenderness, she cooed. “Oh, does da widdel buby want to cry? Go on widdle kinny, go ‘boo-hoo’.”

Ross squeezed his eyes shut and just tried to swallow his ego and prayed for it to be over. “I’m sorry Cherry.”

His sister pushed him roughly back into his chair and growled, “You’re fucking right you’re sorry punk. Fuck you.” Glancing to his computer, she leaned over to yank out the power cord and give the tower on the floor a swift, short kick. He stopped himself from shouting out and making it worse and let her temper tantrum run its course.

With a final ‘humph’ from her, Cherry turned on her heel and sashayed out of her brother’s room, her tight ass swaying. Ross spent several minutes taking deep breaths and thinking calming thoughts. His preferred go to for self control was imagining a glacier, blue and white, floating in clear water and just above freezing. Remembering the sensation of cold and quiet helped lower his blood pressure and put whatever was annoying him behind him.

He eventually felt himself calming down and plugged in his computer again and restarted it after checking Cherry’s anger didn’t fuck up his tech too much. Everything ran fine and he did one final scan while picking up a book and reading that while waiting to see if his bitch of a sister reappeared to flip out again. She stayed in the living room and after an hour of no further outbursts, Ross felt safe enough to return to the email he’d been perusing in the beginning. He had to admit he was still fairly pissed and his anger fueled an incestuous lust for his sister he usually kept under wraps. The fact she was a spoiled, entitled bitch always irked him. And honestly the thought of her being a bitch but still being his personal cum-dump made him hard.

Decision made, he started responding to the e-mail.

Description of Ideal Partner: A girl who looks identical to my older sister, Cherry Culkin. The same long blonde hair, and crystal blue eyes that she has. Also, the same body type, with her massive DDD-Cup rack, fit and with a stacked booty to boot. Not quite the same personality though. Still a bitch, but a devoted, nympho bitch who likes to be my cum-dumpster and cater to my sexual needs. She enjoys dressing really slutty and provoking me into using and abusing her. She gets off on verbal and physical **** from me and is only sexually interested in me. In general, someone who looks similar to my sister and as much as a bitch, but also a willing sex ****. She still radiates contempt and haughtiness, but she craves my pleasure and obeys me. Also make her more sexually aggressive towards me, but still casual about it and with an exhibitionistic streak. Basically shameless towards any incestuous actions with me. Also I’d like if she was very sexually talented and enjoyed pleasing more than she does being pleased. Very sexually responsive and cums very easily when we’re together. Could she also have some tattoos and be naturally hairless below her eyebrows? One more thing, she can’t get pregnant and likes it raw. Also she doesn’t want or need to wear bras and finds thongs and g-strings very comfortable. Likes to show whale-tail. Plus, I don’t want her to be dependent on my wallet and not such a malicious bully anymore. Make her bi-sexual and with a fetish for helping me score with hot chicks without jealousy. Zero sexual boundaries or inhibitions with me. Whatever I want, she wants to do. Finally, she shows zero interest sexually or otherwise in males other than me.

Ross looked over his request and internally cringed. God, he was pathetic. He basically wanted his sister to still be a bitch, but also his sex ****. How the fuck would that even work? Figuring he had nothing to lose but more of his battered pride and risked only more derision and mockery, he sent it off.

************************************************************

The Parallel Dating worker checked the newest response in his assignment queue. Looking it over, he gave a small sigh. Being part of the **** Department had gotten blasé fast. So many people wanted to fuck their relatives. He’d honestly been surprised by how many people wanted their match to be the exact same except fine with fucking. He shrugged. That had only been in the beginning though. Now it was just another day at the office.

Checking the database, he filtered down to immediate life, relatives and then sisters. 300 matches. He sighed again. When the company said infinite possibilities, they meant infinite. He read the request carefully and kept using more and more subfilters. With the professional, hum-drum air of someone who had adjusted to doing his job with casual expertise, he narrowed down the candidates.

“Let’s see. Ink…thongs…braless…” he glanced to the request again, skimming for keywords, “hairless below….eyebrows…” that wasn’t too unusal. “Aaannnd….NOT a gold-digger….gotcha!” Double and triple checking the requested traits and his choice, he landed on three final options. The final decision came down to the amount of tattoos. He decided to err on the side of caution and chose the sister with the fewest amount of tattoos. Just a few, unobtrusive pieces. Training had recommended when in doubt, hew as close to the original as possible. He hoped that would be ok and matched the client’s definition of ‘some’.

“Send and logged.” the worker blew out a breath and spun around in his office chair for a moment’s amusement before checking his docket again. “Well, back to the grind.”

*****************************************************************

Not an hour later and Ross got a response.

Thank you for choosing Parallell Dimensions Dating Services! Your match had been made and the initial encounter set. Once the meeting has begun, you will have 72 hours to determine long-term compatibility. In the event that the match is unfavorable, please feel free to notify us and we will review our process as well as request feedback to provide you a better option. Please be on time for your match and if the venue or time is not appropriate, respond to this email with 12 hours notice and we will handle rescheduling. Enjoy your encounter!

Parallel Dating Services Inc.

What the hell? Ross glanced out his door and saw Cherry still watching TV mindlessly as she played with her phone. This couldn’t be real. Could it? Checking the address of the ‘encounter’ and timeframe, each would be fine. The place was a decent restaurant in a safe neighborhood. There was plenty of traffic and it was unlikely he’d be jumped in the area. Well, nothing to do but check it out.

*****************************************************************

Ross checked his pockets as he started to head out. Patting himself down, he made sure he could feel the necessities in his pockets. Keys, wallet, phone, balls. Everything was where it should be.

Cherry had gone off over two hours ago and he was suspicious. He figured either this bullshit was legit at best. But how the fuck could that happen? At worst, he was being setup for **** humiliation and unending mocking. Which was frankly more likely. Well, it wasn’t like living with her wasn’t a little slice of hell already. Worst comes to worst, he’d save up enough money for a few months and move out. Then he’d just have to try and resist his parent’s browbeating and keep looking over his shoulder for a few years for imminent beat downs.

Listening to Zero-7 to try and calm his nerves on the way, he saw the restaurant was decently busy for a weeknight and the surrounding businesses were also doing well. He’d gotten there at least twenty minutes early and made sure to park somewhere he could keep an eye on the entrance. He didn’t see anyone he recognized enter and unfortunately, the windows were curtained, so he couldn’t look in. Ten minutes until showtime, he decided to nut up and go in. Hopefully, he’d see if there was a bunch of people waiting to jump him and could make a beeline for his vehicle. Unless some people were hiding in the nearby businesses and were ready to cut off his avenue of escape.

God, he was being paranoid. Being a creepy dweeb will do that to you. Taking one last deep breath, he walked in as casually as possible and looked around. No familiar faces at least.

“Hello!” a host greeted him with a bright, cheery smile. “How many in your party?” he asked as he moved from behind the podium.

“Uhhh, I’m here for the reservation under Ross Culkin?” he stated to the host.

The host looked over a paper at his podium for several seconds then brightened up again and said, “Yes, Culkin! Party of two for the Parallel Dimension Services! Right this way please.” and lead Ross away without picking up any menus.

‘Jesus, they have the staff in on this too? They’re committed to this thing, aren’t they?’

The first surprise was there was already somebody at the booth. The second surprise was it was Cherry. The thing that really twisted his guts though, was the smirk she gave him as she saw him approach and got up to meet him. Ross thought something was insane when she leaned forward and gave him a full frontal hug, pressing her huge chest against his. “Well, you’re on time at least. For fucking once.”

Ross goggled at his sister. Cherry had a habit of dressing skimpy, but her current ensemble was one for the photo album. Her top was a glorified handkerchief, held on by strips of cloth tied behind her and nothing holding it up but the pressure of her cleavage and maybe a faint prayer. Despite looking like a handkerchief folded in half and some material hanging down, modesty didn’t seem to factor in, since she showed off generous cleavage and nearly as much underboob. Her skirt was a strip of denim that was more appropriate as a wide belt. There’s no way she didn’t flash people when she sat down. On her feet were a pair of peep-toe heels that should’ve been worn out clubbing. Not to dinner in an Asian restaurant. Her hair was loose and she let it tumble down where it pleased.

She held onto him for several seconds longer than he expected, still pushing her boobs into him and he was still trying to wrap his head around this. Cherry never hugged him. Him being in her sight elicited a sneer. But now, she held him at arms length and her self-satisfied smirk widened as she took in his reaction. “Why don’t you sit the fuck down, stop looking so surprised, and order?” Her smirk disappeared and her tone dropped. That sounded more like her.

The host had long since left once Cherry stood up and greeted him. A server showed up minutes later and took their drink orders. Ross noticed that she motioned for him to go first and ordered the same as him to drink. Just a Sprite. While he tried to pay attention to the menu, he couldn’t help but notice Cherry’s usual resting bitch face flicker as she looked over at him. “Well? Ready to order, creepy?” she asked.

As a matter of fact, he was. He let her dig at him pass by without comment since he’d been called worse by her and that was fairly tame. “Yeah. You?”

“I wouldn’t have asked if I wasn’t.” she mentioned flippantly and a ‘really?’ expression with a tilt of her head. When the server came and took their orders, Ross noticed that yet again, she looked to him to go first and didn’t rush over him to get her own order in. That was really uncharacteristic of her. And when she passed her menu back to the server with a sarcastic sounding ‘thanks’, Ross noticed something else. She had a tattoo around her wrist. It looked like some simple bracelet bands design. Glancing to her other arm, he noticed there was a matching set on her other wrist. Cherry only had one tattoo of a heart with ‘Love’ inside of it on her hip. She’d gotten it years ago and had complained for months of how much it hurt and how long it had taken to heal. He still stalked her social media, but didn’t follow her because she’d threatened him when she got the idea, and he knew she didn’t get any other ink. Definitely not in the last twenty-four hours. Once the server left to put in their orders, Cherry stared at him with a tight-lipped, ‘now what’ smile and the same head tilt.

Steeling himself for whatever trap he was walking into, he asked her while gesturing “Are those real?”

“Wow.” she deadpanned. Then her tone dripped with sarcasm as she grabbed her own boobs. “Yes. Yes, my tits are real. Wanna feel them perv?”

He felt his anger and lust rise slowly at that quip from her, but he soldiered on and clarified. “I meant the tattoos. Did those get done with henna or something?”

She glanced at her arms, holding her wrists out and giving him a ‘you doofus’ look. “Uh, no. They got done with ink. You know, the kind they put in your skin so it stays?” She thrusted her arms, wrists up at him to inspect. “See?” Ross squinted as he looked at her wrists and she gave a beleagured sigh. “Oh my God. Don’t be such a puss and touch them! Rub them with water or something!”

Ross looked incredulously at her. “You want me to touch you?” Cherry just rolled her eyes and took one of his hands to wrap in around her arm and deliberately place his fingers on the tattoo.

Cautiously, he rubbed her skin, feeling the smooth warmth of her flesh. It didn’t feel like something on her skin. It felt like skin. That would point to the color being under her skin. That would mean her tattoos were real. That would mean she wasn’t his actual sister. Or she was an alternate version of her. But then…. “No fucking way!” he gasped. Looking at his sister, stil holding both of her wrists in his hands, he asked, “Are you here because of some Dimension Dating app thing? Is this real? You’re…you’re not the regular Cherry?”

In answer, she pulled her arms back slowly until he let go and gave a slow clap. “The last horse crosses the finish line. Congrats. You’re not as stupid as my Ross.”

“But, but, you-” he stammered, mind reeling.

“But, but, but.” she parroted back in a mocking tone.

Their food arrived then and they ate. Cherry focused on her own food and only gave him the occasional look. For almost twenty minutes, Ross alternated between goggling at her and trying to pay attenton to his own meal. Finally, he had to speak up. “So, what am I like in your world?”

Cherry rolled her eyes and replied, “Seriously? You’re pretty fucking boring. Which from the looks of you here, isn’t a huge leap. All I get is the occassional grunt from you in communication.”

‘Okay, she’s still a bitch then’ Ross thought to himself before continuing. “So, you’re real? The ink and everything?”

His sister threw her head back to look at the ceiling and make an exhaseprated noise, “Oh, for fucks sake! I’m real!” Then she stood up and moved to stand right next to him, turning around and pointing with both hands at the small of her back. “Look, tattoo! Real! Touch it!” It was a pentacle star tramp stamp. Just above the back of her thong sticking prominently out the back of her skirt.

She was seriously telling him to touch her? “Ummm, I-”

She looked over her shoulder with a glare and growled at him, “Touch it!” He gingerly poked the star with a fingertip. She hung her head and sighed. “Fucking christ.” Glaring at him again, she said, “Lick your finger and rub the tattoo, dumbass. It’s real.”

“But licking-” he began.

“Fine! Lick the fucking mark yourself. Splash it with coke, I don’t care.” she interrupted him. Ross watched her warily as he sucked on his thumb for a few seconds to coat it in saliva and gently brushed the star. No smudging. Just skin. And she didn’t flinch from his touch. When he’d finished with that, she turned to face him and raised a leg to plant her foot on the edge of his seat, pointing at her ankle. A band of chain and vines wrapped her ankle and a few delicate vines climbed inches up her toned calf and shin. She just stared at him with a raised eyebrow and he knew the drill by now. Wetting his fingers lightly in his drink, he rubbed her ankle and the ink on her calf with definite pressure. Still no smudging. Cherry huffed and returned to his seat when she saw the acceptance in his eyes.

“So, why did you answer the e-mail?’ he asked quietly, as they returned to eating and he got full.

“I answered the e-mail. I got matched with you. Deal with it.” she replied curtly.

Ross didn’t push it and picked quietly at his food while she finished her meal. When their server brought the check, Cherry took it immediately and put a card in it. Ross looked at her with surprise, but she just glared back in challenge. After the server brought back her card and she’d signed off on the check, Cherry stood with him and looked expectant. Ross remembered the sexual requirements he’d put down and felt his rod stiffen in his jeans. “Did you want me to walk you to your car or….”

Cherry stared at him and just asked, “Your place or mine?”

“Huh?” he managed like an idiot.

“And we’re back to the grunting. Great.” she drawled. “The e-mail said we had three days, remember you moron? Unless this is all total bullshit, I want to use up the time. So are we going back to my place, or to yours? Fuck it, we can get a hotel room if you’re so uptight. I’ll pay for it.”

“Really!?” he yelped.

Another eye roll. “Yes, you idiot.”

He eyed up this other Cherry. She definitely had the bitchy attitude, but paying for stuff? Dressing like she should be on a street corner somewhere? For him? That was way too unusual. “We can uh, go with me. I mean, I can drive, right?”

She just nodded blandly and followed him as he walked to the doors. The host wished them a cheery rest of their evening and Ross just smiled and said “you too”.

The walk to his SUV was awkward and he wasn’t sure what was going on anymore. Was this Cherry really willing to be his sex ****? He started his truck and started to drive out as his sister got settled. “So…hotel?” he asked.

“Whatever you want.” she said. He didn’t reply and just drove quietly for a few minutes as she watched him. Finally, giving a heavy sigh, she asked, “Look, do you want a blowjob?”

“What?!” Ross exclaimed, his hands almost making them swerve.

“You heard me.” she said, nonplussed. Then drew it out word by word. “Do. You. Want. Me. To. Suck. Your. Dick?’

“You mean, while I’m driving? Now!?” he was beyond baffled. Was this really happening? Had he gone insane?

“Well, yeah! Why, think you’ll kill us if you’re in my mouth? Pull over and I’ll blow you behind a dumpster in an alley. We can do it in the backseat.” she gestured to the back. “Besides, this,” and she reached easily between his legs to massage the bulge between his legs, “probably wants to come out and party.” she grinned wickedly at him.

“I-I mean if you would, that would be gr-” Ross didn’t get to finish the sentence as this alternate version of his sister immediately had both hands on his fly and was quickly working his pants open. Pushing his pants down enough to relieve the pressure on his nethers, she had him out and in her warm, confidently stroking hand in a minute.

“There we go.” She said in a sing song voice and then chuckled warmly. “Hey there buddy. Wanna be friends?”

Ross barely realized she was talking to his cock before she plunged her mouth down on him and his shaft was in a vortex of sloppy, tongue swirling pleasure. “Holy shit!” he exclaimed, while his sister hummed appreciatively and bobbed her head rapidly in his lap. She was sucking him like he payed her! Luckily he drove an automatic and could spare a free hand to rest on the skin of her back. Feeling his hand unoccupied, Cherry groped for it without looking and once finding his free hand placed it on the back of her moving head. “You want this?” he managed to gasp.

“Mmmm-hhhm.” he felt, more than heard her hum around his shaft, her lips and tongue making this the singularly hottest experience of his life. There was no way he was going to let this experience pass by while he had to focus on the road. Using focus he would congratulate himself for later, Ross managed to pull into the parking lot of a closed fast food restaurant and scooted his seat back around his sister’s act of fellatio.

Using both hands now on her head, he enjoyed the feel of the golden silk of her hair almost as much as her hot, sucking mouth and energetic tongue. Ross could only groan at the spectacular sensations his alternate sister was giving his prick. But trying to continually brush her hair back to see his shaft disappear between the tight seal of her lips was detracting from the experience. "Can you-huff-hold your hair back or-uuungh-something?” Without pausing, Cherry took her hands from where they had been lightly jacking him off and gently caressing his hairy nutsack and used a hairtie that she had produced from who knows where to pull her hair into a neat ponytail. “Holy fuck, your mouth feels so grrreeeaaattt!” he moaned at his sister acting like a pornstar.

“Mmmmmm” she hummed again in response, not wanting to let his dick out of her mouth. Ross took notice that she’d shifted from leaning over in the seat to kneeling up on the seat to lean over his lap more directly. The action had hiked up her technically-a-skirt to flaunt her juicy, firm ass cheeks neatly bisected by a tiny strip of cloth below the hem and the beautiful ‘y’ of her thong back above the skirt. He couldn’t help himself, Ross took his right hand and brought it down on the tanned skin of her ass with a hard ‘crack’. “Mmmmm!” Cherry responded with an approving sound that reverberated pleasure down to his balls.

“Yeah, you like that you slut?” he asked her, punctuating the question with another, harder spank to her other cheek.

“Mmmm hhmmmm!” she moaned again, her head speeding up its bobs and sucking pressure.

“Fuck! Holy fuck you’re a slut!” he said with a grin as he alternated spanks on her ass at random intervals. The SUV filling with the ‘shlack, shlack, shack’ of increasingly forceful impacts of skin to skin. “You like this, being your brother's nasty fuckslut? You want this brother cock in you, huh?!” His left hand gripped her ponytail, but Cherry made no move to stop impaling her pretty face with his shaft.

“Mmmmmmmm!” She moaned so loud he could hear her above the spanking he was giving her.

He switched tactics and placed both hands on her head, one gripping her ponytail, one pushing the back further, guiding her forcefully, but she smoothly followed his directing the pace. “Fuck you, you fucking slut!” Cherry’s ponytail was waving like a perverted, blond flag in his lap and her skull was bouncing so rapidly, she was almost a blur. “Suck that cock whore! Suck my cock! You want it! You need it! Fuck you!!!”

“Mmmmm!!! Mmmmm!! MMMMM!!!!” she wailed with a cock stuffed mouth, loving her treatment.

On edge already, Ross shoved her head down with all the leverage his arms could give and began spasming, his legs kicking aimlessly as he shot what felt like the biggest load in the history of teenage boys down his sister’s gullet.

Cherry for her part groaned so deeply, his entire body felt her growl and he didn’t notice her eyes rolling back as she came just from sucking her alternate reality brother off. She kept sucking and swallowing like a trooper though and the thought she was eating her brother’s load just amplified her climax.

Minutes later as they both came back down to earth, Ross remembered he was holding her face down and could feel her breath tickling his pubes as she breathed in and out. Cautiously taking his hands off her head, Cherry gave one long exhale and slowly lifted her head up and mouth off him with a wet ‘ssscchhluurp’. Ross braced himself for the other shoe to drop in a very unpleasant way, but Cherry just gave him a pleased smirk, cool as a cucumber, and asked, “Again?"

(Hi all, Withness here. Big thank you to TheNextGamer for this great new story and premise. As before, any call outs, please leave me a comment or feel free to send a DM. Not sure if I wrote the sister character correctly. Let me know what you think.)