The Trouble With Tess Pt. 01

Matt sat quietly and processed what his sister had said. He didn't want to put his foot in it again. Not when she had opened up to him. She was letting him in.

"That sounds like a lot of work," he said finally.

"It is," she replied with a heavy sigh.

"But is it what you want to be doing? You said 'their' goal, Tess. That implies it isn't yours."

"I want to be the best," his sister replied.

"You can be the best at a lot of different things, Tess. It doesn't have to be at something you don't want to be doing," Matt said.

"What do you want to be doing? What would make you happy?" he asked.

"Is anyone really happy anymore?" his sister countered.

That took him aback. He'd thought a lot of things of his sister. But bitter had never really been one of them.

"That's not really an answer, Tess, but I mean, I'd say I am," he replied.

"Mmhmm. If you were happy then why are you back here?" was his sister's response.

Once more Matt was taken aback. This time because he simply didn't have an answer. Tess was making him think just as much as he was trying to get through to her. He'd considered himself happy. He enjoyed his work. Enjoyed his friends and relationships. There had just been something missing. Something that left a hole in his life that he'd been unsure how to fill.

He was still silent, thinking, when Tess got back up and reached out a hand to pull him up as well.

"Cmon, we gotta go before it gets too hot. Plus I gotta get to work."

Matt took the offered hand and levered himself to his feet.

"You gonna be home for dinner tonight?" he asked Tess.

"Probably not, but I'll let you know. I've got a lot to do at work while Mum and Dad are away. Can't be seen to be slacking."

Matt nodded a silent reply as he followed his sister into a jog. It was progress. At least she'd probably reply to him this time if he texted her.

Falling into a steady rhythm as they ran back home, it wasn't long before Tess started to outdistance him. Her long legs and running background leaving Matt trailing behind. Without really noticing, he became lost in his thoughts while he ran. Matt's gaze locked onto the rhythmic jiggle of Tess's ass again. He was still staring and following blindly when they got back home.

"Matt. Matttttt...Earth to Matt."

Matt jerked back to reality with a start when Tess's repetitive calling finally broke through. His sister was calling to him over her shoulder, and he hastily averted his eyes when he realised he'd quite obviously been caught staring.

"Something catch your eye?" Tess asked with a raised eyebrow.

"Nope, just lost in thought is all," Matt denied quickly.

"Uh huh," Tess scoffed at his answer. "Sure you were."

"We were having a serious conversation, Tess. I think being lost in thought is allowed," Matt tried again to make his case.

Tess laughed at him then as she unlocked the front door of the house.

"It's just an ass, Matt. You can admit you were looking, I know I've got a good one," Tess teased him.

Good was an understatement. Phenomenal was a much closer description in his opinion. But that wasn't something he could admit. She was his sister.

"Ewww, you're my sister, Tess, you can't say shit like that," he groaned at her instead as they entered the kitchen together.

Reaching into the cupboards for some glasses, he could've almost sworn he saw a look of what could only be described as disappointment flash across his sister's face in the reflection when he said that. But whatever it was it was gone as soon as it appeared, and when he turned back around, she was looking at him with obvious doubt.

"And you shouldn't be staring at it for several blocks!"

"I wasn't!"

"Yeah, and I'm the Pope."

"Oh piss off, Tess, go to work already!"

"Awww, and I thought we were bonding," she laughed at him again.

"Here you go, you can watch it again one last time," Tess said, and she gave her own firm flesh a slap as she walked away from him to get ready for work.

"Fuck me," Matt muttered, and he was glad Tess was walking away for more then one reason.

He turned and faced the bench to hide the very-quickly-growing erection he now had. That spank. The jiggle. His sister's more playful attitude. They spoke to him. Called to the dirtier parts of his mind.

"Your sister, Matt; she's your sister. Remember that. Fucking hell," he berated himself quietly but that only made him harder.

This was going to be a problem.

Hearing Tess close her door, he hurried for his own room and ducked inside with a sigh of relief. Safe.

He hid. Leaning against the wall inside his room while he listened intently. He needed Tess to leave and he needed her to do it now. His dick was not cooperating at all, in fact every time he thought of Tess it just seemed to get harder.

He was in real trouble. None of his previous girlfriends had ever elicited such a response. Why the hell was his sister?

After what felt like an eternity of uncomfortable thoughts and an even more uncomfortable hardon, he finally heard his sister call out to him.

"I'm heading to work! I'll let you know about dinner!"

"Ok!" Matt yelled back.

As soon as he heard the door slam shut, he moved. Quick as a flash, he was on the bed, his pants were gone, and his laptop was on. It took less than a minute for him to be online and searching for a video.

He needed to get off and quickly.

He'd done plenty of night of internet trawling to find the things that excited him the most when he left home. Not having anyone hovering over him or monitoring what he did had led to a lot of self-discovery.

Girl on Girl, anal, bondage, shibari, gangbangs, bukkake, deepthroat, DPs, orgies, and more. Everything he could think of-and some things he hadn't even considered-had been explored.

Then he'd started on the hentai and things got weirder.

Catgirls, furries, tentacles, monsters, futanari. That had expanded his horizons quite quickly and left him questioning his own tastes more than once.

At the end of it though, he had almost perfected what would be guaranteed to get him off whenever he wanted.

A preference for blondes. But that wasn't a must. Bondage and the Dom/sub dynamic. A bratty type was just an extra bonus. Seeing them teased, seeing them used, and then having them submit to the pleasure, that was what he liked. Matt had several of them saved and he went straight for the first on the list.

After several minutes, Matt couldn't figure out what was wrong. He was hard, he was willing, but the athletic brunette moaning on his screen was doing nothing for him. No matter how she groaned or begged for more. No matter how quickly he stroked his cock, he couldn't feel his relief coming any closer.

Another video; the same thing. A pretty raven haired girl on her knees, teasing and worshipping the fat dick in her face and Matt couldn't feel an ounce of change in his own aching member.

Another video.

Another.

Another.

He was halfway through his list and yet was no closer to getting off then when he started. Matt groaned in frustration. Tess. It was fucking Tess messing with his head. He couldn't concentrate on anything else. His sister's face, her body, her ass. They kept tempting him. Distracting him. He wasn't going to be able to get off this way.

He wanted to deny it. He knew he shouldn't give in to the temptation but he was too hard and horny now to care. It was time to take the plunge into a category of porn that had never interested him before.

His fingers, tapping at the keyboard he quickly went looking for something new.

Blonde. Sister. Search.

The first one Matt found that looked even vaguely like his sister he clicked. Dick in hand, he started stroking as soon as the pretty blonde appeared on his screen. He gave in to the fantasy that was plaguing him. Every movement, every touch. Every moan and seductive groan that came from the video was replaced in his mind by Tess. His sister's lips closing around his cock and dragging slowly down his length. Her beautiful tits pressing against his chest. His hands on her ass, pushing her down, grinding himself into her while the warm, slick grip of her pussy milked him dry.

"Fuuuck!" Matt groaned as the thought of that was enough to tip him past the point of no return.

The orgasm was intense. Pure pleasure from top to bottom, an explosive climax that left him gasping and his head spinning.

"Fucking hell," he muttered to himself as he fell back against the pillows.

Tess. His sister.

Guilt poured through him as post-nut clarity came roaring back to him as he lay in a satisfied heap. He'd just nutted to the thought of fucking Tess. He'd just cum to the thought of fucking his sister and filling her to the brim with his cum. What the hell was wrong with him.

***

The answer to that eluded him. Because he didn't stop. That day became their routine.

They'd wake up early and run together. Stopping at the little cafe, they'd sit and chat together, getting to know each other, and reconnecting just how he'd hoped all over again.

The topics they talked about covered everything that came to mind as they both shared a new joy.

Hobbies.

Tess - Fitness. Any sport she could find the time to play.

Him - Gaming. Reading. Just generally still being a nerd.

Love life.

Tess - lots of dates when she had the time, but no one good enough to match her expected standards.

Him - a few girlfriends but none had felt right. There was always some spark or feeling missing.

Work.

Tess - ridiculously busy and always with something new to do, new to prove. The pressure she was under as the golden child and the heir to the company.

Him - happy with where he was at and what he was doing.

Sport.

They both agreed Penrith were doing great in the footy and the Eels were shit.

Politics.

Terrible.

The Parents.

Tess filled him in as best she could. Both doing well and still always on the go. They never stopped. Both of them expected the absolute best from her while she was at the firm.

It was a refreshing change for them both to just sit and chat, exchange stories and experiences without the cloud of anger and resentment hanging over them. Then they'd finish their water and be back to running. Matt would inevitably find his eyes sticking to his sisters behind, unable to look away, and just as inevitably he'd be caught. His sister never told him off for it, but she'd always tease him about it.

Then she'd be off to work, and he would disappear into the safety of his bedroom and find newer, kinkier incest videos featuring the prettiest blondes he could find.

Doggy Style. Blowjobs. Toys. Spanking. Anal. Bondage and submission. Every scenario and position he could imagine was filled by Tess while he stroked himself to completion.

It wasn't until the following weekend that things changed. He finally found the answer.

***

When Tess made it home early on Friday night for once, she was in a foul mood.

Work had been nothing but problem after problem and argument after argument while they tried to resolve a new agreement. But it had been expected of her to get it done and get it done with the best possible outcome so she'd buckled down and gone for it. No matter what she tried though, the client just wouldn't listen. She'd felt like screaming before they'd even made it to lunch. Even now, with her parents thousands of miles away, she could feel the crushing weight of their expectations and disappointment piling onto her own.

She'd been hoping that an evening spent hanging out and teasing her brother would cheer her up. The past few days together had been amazing. Reconnecting: chatting about all kinds of things as they both actively tried to repair the relationship between them. The depths of Matt's resentment towards her and their parents had caught her completely off guard. She'd just brushed it off as being unappreciative of what he was being offered or general teenage boy moodiness. They'd all wanted the best for him, and it had just seemed he was fighting them for the sake of fighting.

But now they were older. She herself was more experienced; the ease with which she had cruised through their youth had faded, and she could relate to that unrelenting pressure to match the expectations of those around her now.

The resentment wasn't misplaced; they had ignored his desires and tried to force his path. But he'd taken it too far in her opinion. Running off, basically cutting off contact with them without really trying to explain himself, she'd felt crushed by his abandonment even if she'd never admitted it. That was on her too. She hadn't tried to reconnect with him. Too busy trying to maintain her life, her job. Everything else except Matt had been a priority, and he'd just faded into the background as something to keep an eye on to make sure he was ok.

But now he was back. And she felt happier with him nearby than she had in years.

The moment Tess opened the door and entered the house, though, she knew her hopes had been dashed. The place was empty, that sixth sense that told you that you were alone letting her know that Matt was not around.

"God damn it," she sighed.

Dropping her bags carelessly onto the floor, Tess dejectedly headed for the kitchen. If her brother wasn't here, at least that still held something that would make her feel better about the day.

Heading directly for the fridge, Tess flung it open and reached into the cool exterior for a drink. Premixed Vodka was her vice of choice these days, and she slammed the first one back in minutes. Reaching back into the fridge, Tess grabbed another pair of drinks before heading to the lounge. Time to have a party of one.

***

Matt was at a bar. He was no longer sure which bar; there had been a few so far already and he was quite pleasantly tipsy. Some of his old friends had finally been available to hang out so he'd taken the train into the city to meet them, and he'd been following them from bar to bar for what felt like a few hours now. This one was dark, loud, and filled with people who were once more enjoying the freedom to congregate and party.

He'd been enjoying himself as they all caught up and swapped stories. They'd all fallen back into the familiar groove of banter and good-natured ribbing. It was a pleasant distraction from thinking of Tess and all the confusing as hell emotions that was bringing along with it at the moment. But he'd lost them in the crowds and was now sitting by himself at the bar, swirling the remains of his drink in a glass, and was now doing exactly that.

He'd somewhat guiltily beat one out to thoughts of his sister again before fleeing the house. He already missed her and wanted to see her again. Matt shook his head. He really needed this time apart to clear his head. He shouldn't be fantasizing about his sister of all fucking people.

"Hey, stranger."

Matt's troubled introspection was interrupted by a familiar voice and someone sliding into the spot beside him.

"Kate!" he exclaimed in surprise. "Where did you come from?"

Leaning across, he wrapped his friend in a tight hug which she returned warmly.

"Oh the others texted me earlier saying you were all out and I should meet you here. But you're the first one I've found."

"Yeah I've lost track of them as well," Matt replied, "so I've been enjoying a drink to myself."

"Well I'll join you then," Kate declared.

"Awesome," Matt said, and he meant it.

Kate was good fun. They'd been friends for ages, and they'd even hooked up a few times at parties and such, but nothing more concrete had ever developed. He looked her over as surreptitiously as he could. She was still as good looking as ever too.

Kate had been the emo girl. Dyed hair, the black clothing, nose piercing, fishnets, and My Chemical Romance were the rule before he left.

From what he could see now, that had changed only slightly. Dark clothes still ruled. Sleek black boots that made up for the difference in their height, a dark skirt, and a tight fitting band shirt moulded to her slender figure were all a delicious contrast to her surprisingly pale skin. Instead of completely black, there was now a neon pink fringe to her short hair. Her nose piercing had changed from a simple stud to a pair of rings and there was a chain of them along her ears. He could see a few tattoos now as well, some half showing from beneath her sleeves, and another on her leg where her short dark skirt didn't quite cover it all. There was also one peeking out from beneath her top with a tantalising amount of cleavage. Matt quickly averted his eyes from that before he had even more trouble with being caught staring.

"You look good," he told her truthfully.

"So do you," Kate said with a much more open and appreciative look at Matt.

He'd gone with a pretty simple combo of dark jeans, boots, and a button up shirt. He knew he filled them out better than he had before. His new workout and slightly healthier eating regime had helped with that. But having Kate so openly ogle him had him blushing.

She laughed at him before coming to his rescue and changing the subject.

"So what's got you looking so forlorn? Don't tell me Tess is giving you trouble still?" she asked before she ordered a drink.

Matt had to wince at that. His sister was definitely doing that. Just not in the way Kate meant it. Or at least he hoped not.

"Tess is fine. We've been having a really good time together actually; things are going well," he said.

"Well that's good, I'm happy for you guys. But that doesn't explain the long face," Kate replied.

"Girl trouble?" She guessed. "I thought you were single."

"Still single," Matt confirmed with a smile, and Kate appeared pleased with his answer.

"Well then, what's up?" she tried again.

"I'm just trying to work through some stuff is all. Coming home has brought a lot of things to the surface, and I don't know how I feel about it."

"Fair enough," Kate replied, "but if you wanna talk about it, I'm happy to lend an ear."

"Thanks," Matt replied, not adding that he doubted she'd want to hear about his troubles with sisterly fantasies. He appreciated the offer anyway though.

"So what've you been doing with yourself?" he asked to steer the conversation away from his problems, "still teaching?"

"Yeah, still teaching, the stress is unreal, but the students are great," Kate replied and took a sip of her drink.

"Still IT?" she asked him in return.

"Yeah, still IT; that's not gonna change," Matt replied with a grin, sipped his own drink, and let the conversation distract him.

Perhaps this meeting was exactly what he needed to get Tess out of his head.

They soon settled into the flow, the familiar bond of friendship returning as if they'd never been apart for years. The drinks started flowing as easily as the conversation and the hours just slipped by without a care. Without noticing, they'd both edged closer and closer, till they were sitting shoulder to shoulder and whispering in the other's ear.

It was past midnight when they both wobbled out of the bar, onto the street, and into the warm night air hand in hand. They hadn't managed to find their friends again, but both of them didn't particularly care. They'd enjoyed themselves anyway.

The city was still alive even at this hour, bright lights shining everywhere, people walking past in boisterous, drunken groups. Cars, buses, bikes, and trains all added to the city's midnight chorus. They joined the flow of pedestrians, weaving their way along the path as they continued to enjoy themselves.

"Soooo," Kate dragged out as they finally stopped at a train station.

"Did you wanna come home with me?" she asked, pressing herself up against Matt's chest.

***

Tess was drunk. Quite drunk, she could admit to herself. The vodkas hadn't really stopped since she got home, and the pile of cans that now littered the kitchen bench attested to her dedication to inebriation.