Your Brother has to Cum

Unlike most of what I write, this one is fairly short. For now, it is intended as a standalone story. If it's popular, though, I could see adding another chapter in the future. As always, everyone here is over the age of 18. Enjoy!

*****

"Your brother has to come!"

Whenever Hailey asked permission to do something fun, her mother had one solution: your brother has to come. It made Hailey nuts.

Hailey wanted to hangs out with friends at the mall? "Your brother has to come."

Hailey wanted to go to the movies with a super cute boy? "Your brother has to come."

And tonight, when Hailey had finally been invited to one of Madison Hawser's famously fantastic parties? Well, then, Mom had the perfect solution. "Your brother has to come."

It was beyond annoying. Hailey was a sophomore in college, for God's sake. Just because she was stuck living at home, that didn't make her a child. She should be able to go wherever she wanted without having to drag along her awkward, high schooler brother, Tommy. He was like an anchor with long legs and curly hair.

But that's what made it so perfect, you see? Tommy, had only just turned 18, so Hailey couldn't take him out to a bar. Tommy was gangly, shy, only ever comfortable in front of computer screens (or TV screens, or movie screens). He was a total drag at parties. And dates? Who brought their baby brother with them on a date?

Hailey loved her brother, she really did. They'd been close when they were younger and she had no doubt they would be again. At some point in the far future. Far far far. But right now she was in college and she had college friends and wanted to go to college parties.

"But Moooom, there are gonna be bo... I mean, people there. Tommy's just gonna get in the way."

"You don't have to bring him with you," Hailey's Mom replied, "You can both stay home. I'm sure Tommy would love some bonding time with his big sister. What do you think? Do you want to stay home with your little brother?"

"Nuh uh."

And thus it was decided.

*

Hailey dug her brother out from behind the Xbox and told him he was going to a party. After no small amount of arguing, she was able to force Tommy into something that at least approximated an appropriate outfit - dark slacks and a darker dress shirt. Then she combed her younger brother's tangled mop of hair to make it look like he didn't comb it, spritzed him with some cologne, and called it done. The situation was still a mess, but Hailey had to admit her brother cleaned up pretty well.

For herself, Hailey picked out a little red dress that accentuated her curves in all the right ways. It had been a gift to herself for all her hard work. Hailey had spent the entire summer doing two things - busting her butt for tips at the restaurant, then working it into shape at the gym. For maybe the first time since puberty had arrived so rudely at her door, Hailey was proud of how she looked. She tucked her long, reddish-blonde hair behind her ears and skipped happily down the stairs.

Since Hailey had been so cooperative, her mother let her borrow the SUV. The suburban streets were already quiet at this hour. There was nothing to do but listen to the hiss of the road, feel the thumping beat of the stereo, and stare out into the world.

Hailey thought she caught her brother eyeing her chest. She flushed a little, embarrassed, and tried to take it as a compliment. The dress was a little revealing, she had to admit. Besides, most of the girls her brother looked at were probably named .gif or .jpeg. Seeing a real one was probably breaking his brain.

Poor Tommy. You had to be pretty hard up to be ogling a blood relative. Although, Hailey had to concede, her brother did look pretty cute in the outfit she'd chosen for him.

"Watcha thinking about, Tommy?" Hailey asked, taking her hand off the wheel to tousle his curls.

"Tom. I've asked you like a hundred times, please call me Tom. What is this party anyway? Five desperate college kids playing spin the bottle?"

"Nuh uh! It's hosted by this girl I know from work, Madison. Her parties are, like, famous. She's got an awesome, huge house with a pool and her parents are away for the whole weekend. Madison's, like, the coolest girl I've ever met. I mean, she knows everybody. So, probably a whole ton of awesome, cool people will be there."

"So that's why we're going? To hang out with this super popular girl and her empty-headed friends?"

"And, well... maybe cause this cute boy's gonna be there and I really want to hook up with him?"

"Hailey! Ugh, I knew it."

"What's the problem? Tyler's gorgeous. And amazing."

"He's probably an asshole," Tommy said, crossing his arms.

"How dare you speak that way about your future brother-in-law!"

"Whatever. So I guess I'll just like, sit in the corner while you make out with your mimbo." Tommy stared out the window, studiously avoiding his sister's glare.

"There's going to be a ton of hot college girls there, too," Hailey said.

Tommy paused. Processed. "How do you know they're hot?"

"I bet I'm the ugliest girl there," Hailey said.

"I doubt that," Tommy said, running his eyes over Hailey like a sibling shouldn't, "I don't think there's anyone better looking than you. In an - ahem - a brotherly way, of course."

He tried to pass it off as a joke, but Hailey couldn't help but feel, deep in her heart, that her little brother really meant it. It should have freaked her out, but instead it just made her feel all warm inside.

*

After two years of college, Hailey had been to a lot of parties, but she'd never seen anything like this. The house was massive. The music, thunderous. And yet the one thing Hailey couldn't get over was how many people were there. A horde of humanity was drinking on the lawn, dancing in the driveway, laughing and shouting and running around like maniacs. Like ants on a watermelon, they seemed to swallow everything around them.

At the front door, a boy Hailey didn't recognize gave her and Tommy each a red Solo cup and then sent them on their way. As crowded as it had been outside, the inside of the house was worse. Hailey imagined that this was a fine home, but at the moment, it felt more like a NYC subway car. And smelled similarly, as well.

Hailey had to fight her way down the hallways, dragging Tommy along. Finally, they found the kitchen and, most importantly, the alcohol. A girl with long curly hair was mixing drinks at a makeshift table. She smiled and waved, but Hailey barely noticed. She was focused on the keg behind the table and the uber-cute boy standing next to it.

He smiled as soon as he saw her.

"Tyler." Just speaking his name seemed to shift the winds and, well, it was appropriate. Tyler was like a Greek god. Tall with close-cropped brown hair. Athletic, though not over-muscled by any means. He was breathtaking. The fact that he'd even smiled at her was... Well Hailey must have sacrificed the right animal to gain his favor.

"Hi Hales," Tyler said, then took her cup and filled it with beer. Without pausing, he grabbed Tommy's cup and filled that one as well. Hailey turned to give her brother a disapproving look, but he was already drinking. Hailey told herself she didn't care - she was here to be Tyler's girlfriend, not Tommy's Mom.

"Who's the guy?" Tyler asked, eyebrow raised.

"Nobody," Hailey said. If she noticed her brother's face fall, as she spoke, it didn't register. She was far too focused on the college senior standing in front of her. They both went to Rutgers, but Tyler was two years older and way more mature than any of the boys Hailey'd ever dated. They'd only met because both Hailey and Madison worked at the same Chili's on Route 22 and Madison had introduced them.

They'd gone on a couple of group dates - Hailey and Tyler with Madison and whoever the boy of the week was - but it was never something serious. He'd given her a peck on the lips once, though Hailey would have been happy to do much more. Tyler was so super hot and mature and... Perfect, practically.

"You should probably go say 'hi' to Madison," Tyler said, still spritzing beers into people's cups, "She's out back by the pool. I'll join you guys in, like, five."

"Cool, just let me ditch my little brother and then I'll..."

Hailey glanced back, but Tommy was already gone. She spared a fleeting thought, hoping he'd actually talk to people for once and not just stand in the corner staring like some creepy perv. Maybe he'd actually get some tonight, Hailey thought, hopefully. Then, strangely, she felt a little jealous at the idea. She quickly buried the feeling before it could grow any further.

*

The back deck was as busy as everywhere else, though there was way more breathing room than inside. The air smelled like fresh cut grass and chlorine, mixed with alcohol and pot. Night had fallen hours before, but the entire area was lit to practically daylight and it gave everything a very ethereal, unreal quality.

Hailey had no trouble finding her host. Madison was sitting by herself on a lounge chair, wearing a lacy pink tank top and a pair of little yellow shorts that probably covered less than some of Hailey's panties.

With a martini glass in one hand, brown hair tied back, and oversized yellow sunglasses over her head, Madison looked absolutely glamorous. Hailey felt shoddy in comparison

- her red dress showing off all her curves in the worst way.

"You look good," Madison told her. Hailey smiled and said thank you, feeling the compliment genuinely. "Has anyone offered you a martini?"

"Nuh uh," Hailey said.

"Well that simply won't do," Madison said. She immediately gestured to another girl who ran off and brought both Madison and Hailey the cutest little flamingo-pink drinks. Hailey took a sip and it was super sweet. Way better than any stupid old beer. She quickly lost count of how many she finished.

Tyler joined them soon after, and while he didn't make any moves, Hailey could see he only had eyes for her. He was so hot it made her whole body melt. And Madison was so cool, too. Hailey had only known the girl from work where she could be a bit cold at times. Distant. Even rude.

But here at her home, Madison had opened up. She told them funny stories about things she'd done with her sorority. Talked about a recent trip to Paris with her family. Her adventures on their yacht. For Hailey, it was like seeing the previews for this amazing, almost fantastical, new TV show and then, it being hinted, that she might be getting the whole box set for Christmas.

Sitting under the electric lights by the pool, Hailey felt like everyone out back was watching her, jealous of her vaunted position - sharing a lounge chair with the hottest boy there and the elegant hostess, herself.

But then, Hailey felt something else. That little tingle in the back of her brain that said someone was staring at her. She turned and, sure enough, saw her brother looming by the far gate. God fuck it. Why couldn't that boy just... Ugh! Well, he was allowed to go wherever he wanted, she supposed, so long as he didn't bother her.

"Ooooo, who's that?" Madison asked. Hailey felt her heart sink. Sure enough, Madison was looking over at Tommy.

"Didn't you come with him, Hales?" Tyler asked.

"Yeah." She looked down at the ground.

"He's super cute," Madison said, "Is he your date?"

Hailey mumbled her response.

"What's that?"

"Tommy. He's my little brother. My Mom made me bring him."

"And praise the good Lord that she did. He looks good enough to eat," Madison said, and smiled like the predator she was.

Before Hailey could stop her, Madison waved Tommy over. That puppy dog look on his face... Oh Tommy. He sat on the chair next to Madison, facing Hailey. He smiled at her and even squeezed her arm a little.

Jeez bro, body language! Didn't anyone tell you to sit so you're looking at the girl you want to be with?

"So," Madison began, "Tommy..."

"Tom, actually," Tommy said, "I prefer Tom."

"Well, Tom. Hailey here says you're her little brother, but that hardly seems true," Madison said. She ran her eyes from the top of Tom's curly hair down his long, lean body to the tips of his scuffed, black shoes.

Was her brother really so attractive?

Hailey tried to look beyond her past experience and see Tommy, her brother, as Tom, the stranger sitting next to her. Sure, Tommy was a dork with few friends and fewer social skills. But Tom was tall and - she could see it in a way - handsome. He had deep green eyes and the beginnings of a beard on a wide, square jaw. Tommy was a klutz, but Tom's body seemed lean and almost toned. When had he had time to do that? Or was this just the natural transition of teenager-to-adult kicking in, burning away the baby fat?

Then Hailey noticed something. Tom was answering Madison's questions but he was looking mostly at her, his sister. And Hailey recognized that look. It was the same one she'd been giving Tyler all night - that combination of wonder and desire. Hope and hunger.

Was Hailey's brother actually...? Ew. No. Tommy wouldn't. Couldn't. Even though he looked kinda cute. More than kind of cute...

Nuh uh. Hailey tucked that thought back into her brain, before the whole place became cluttered with thoroughly inappropriate, totally unacceptable, not exactly actionable feelings.

Instead, Hailey forced herself to root for this Tom fellow to seal the deal with Madison. After all, if Hailey could have the oh so sexy Tyler, then why couldn't her little brother get a bit of (even Hailey had to admit this to herself) the ever-attractive Madison?

Fortunately, the more they talked - and the harder Madison flirted - the more Tom seemed to appreciate her attention. Soon, he was completely focused on Madison and Hailey was pretty sure she could see a bulge building in his pants. Not that she was paying that much attention or anything.

"Gah, it's hot as balls out here!" Madison said, then slapped Tom's leg, "Come on, stud. Let's take a quick dip."

She stood up and sauntered over to the water's edge. Up to this point, despite the heat, no one had so much as dipped a toe in the large, kidney shaped pool. The almost sapphire water lay undisturbed, smooth as a fresh cut jewel.

Madison didn't even bother to take off her clothes, she just slid into the azure like a mermaid. Her head popped back up, brown hair slick and dark. Hailey could see Madison's nipples poking through her sheer shirt and felt a little embarrassed for her. It would be awful to be so exposed in front of this many strangers.

Then Tyler jumped up, shucked his shorts, tossed off his shirt, and ran for the water. Seeing him in just a pair of white boxer briefs, Hailey's eyes tried to pop out and roll right after him. Greek god? Even the immortals would appreciate that boy's body.

Tyler whooped out a war cry, then leapt, hitting the water with a loud splash and soaking the partygoers foolish enough to be standing nearby.

When the water settled, Madison called out, "Come on, what's keeping you two?"

Tom looked over at Hailey, like he was hoping for some help. Hailey shrugged. The siblings slinked to where the pavement met the pool water. Meanwhile, Tyler and Madison pranced about. Playfighting and giggling. Then they both stopped in mid-wrestle.

"Fuck, Maddy, nice!" Tyler said. Madison was sort of pressing herself against him and neither seemed too unhappy about the experience.

At that moment, both Tom and Hailey came to the same conclusion. Get in the water, or risk losing their individual conquest to the other's.

Tom unbuttoned his shirt and stepped out of his pants. He was wearing boxers, blue ones. Hailey couldn't help but stare. Her brother was no Tyler, but then, he wasn't so bad either. Tom had some real definition in his arms and chest. And what was pointing from his boxers was...

Hailey quickly focused on her own clothing. With one swift move, she lifted the red dress right over her head, leaving her standing there in just her underwear - a somewhat modest set of lacy pink panties and a matching bra.

Hailey turned to look back at her brother and saw... He was frozen. Gaping. Hailey looked down and saw Tyler doing the same from the water. It felt like the whole pool was looking at her and she... didn't mind it as much as she thought she would. In fact, she felt kind of sexy.

"Nice bod!" Madison called from the pool.

"Thanks," Hailey said, then realized Madison was probably talking to her brother. Whoops! Before she could embarrass herself further, Hailey jumped into the pool. She felt another splash next to her as Tom jumped in, too.

Hailey shivered, immediately regretting her decision - the pool was remarkably cold and she was alone, in her underwear, in front of who knew how many people as well as her own brother. Then a pair of warm hands rested affectionately on her shoulders and chased all those worries away.

Without saying a word, Tyler scooped Hailey up off her feet. Then that beautiful hunk of manhood carried her - like a husband with his bride - down to the far end of the pool where he could stand but she really couldn't.

For a moment, Hailey looked over Tyler's shoulder and saw Madison and Tom, way on the other side. She couldn't tell what they were doing, exactly, but it looked like they were just talking. Well that was OK. More than OK, really.

It freed her to focus on Tyler. The water dripping off his bronze skin. His pecs so muscular and perfect.

He put his hands on her bare sides, then without a word he leaned in and pressed his lips to hers. Warm and rough. Hailey felt surrounded by his strength. Let the world just tip forward.

At first they were both taut - wrapped around each other. Locked in arms and hands and legs. Then Tyler slowly traced his way down to Hailey's chest, using his thumbs to rub her aching nipples through her bra. Hailey felt her body go slack.

Liquid. Like her sex.

Even in the water Hailey could feel her pussy dripping as Tyler ever more confidently explored her body. Hailey used her free hands to trace his chest. Tyler was such a man. There was just no other way to put it. He was masculine in an almost animal sense and Hailey felt herself almost domesticated by his wildness.

She let her mouth open for his tongue. He scooped her closer. Pressing her into his chest. She felt his hardness poke at her legs. Insistent. Her own mound ground against it, almost instinctive.

Then Hailey felt Tyler's hand run down her back and start to slide into her panties. Hailey's first thought was a strange sense of shame. Like he would feel her wetness and know how excited she was and be shocked. Scandalized. As if his own arousal wasn't very clearly rubbing up against her.

But then Tyler's hand was sliding lower and Hailey felt her body respond and...

"Hey!" Madison called from across the pool, "Let's go inside."

It was not a suggestion. Before Haley could even breathe, Madison had climbed out of the pool and hurried back to the house. Tyler quickly followed. Hailey and Tom found themselves abandoned by the edge of the pool, staring at each other. Both a bit bewildered.

Then Hailey looked down and froze. Her little brother was still in his boxers but his cock was poking right out of the open fly. And it was not so little at all.

Wow. Hailey wasn't all that experienced - she wasn't a slut or anything - but she'd seen enough dick in her life to know that her brother's cock was fucking...

Penis, she corrected herself. She had thought the word 'cock' but of course little brothers didn't have those. They had penises. Her brother had a very nice penis which was lovely for him but wholly academic as it applied to her. Yes. As long as everything was kept clinical, she'd be fine.