Read it now for free as an ebook!
Chapter One: Court Fees Got Me Down
Chapter Three: Fraternity Hazing
Chapter Six: The Bouncer’s Bottom
Chapter Seven: The Hunky Pool Boy
Rob flipped through pages from an online Chinese dictionary, looking for the tattooed symbols that danced along the pool boy’s shoulderblade. It turned out to be more difficult than he thought to identify them by sight. The pool boy had a few tattoos, and Rob thought they were sexy. He had been trying to identify the Chinese symbols for a long time. He suspected they meant nothing at all.
“Yes, Hopley, sell it when it hits twelve no matter what. That’s what I said, isn’t it?” That was Rob’s father, the multibillionaire Eugene Winthrop. His gruff voice filled the air, followed by some tinny suckuppery from whichever employee was on the line. He glanced at Rob and scowled. “Tell them to go fuck themselves.” He hung up his phone. “You’re going to this fundraiser tonight.”
“What kind of fundraiser?”
“It’s a dinner thing. Some kind of cancer. Or maybe teachers? I don’t know. Just bring the checkbook, they’ll have a vegetarian option-“
“I’m not going, and I haven’t been vegetarian for years.”
“You have to go,” he said and they both erupted in shouting, as Rob had known would happen. They almost never interacted without shouting.
“You don’t control me-!”
“I pay for so much-!”
“You fucking asshole!”
“Me?! How am I the asshole? You have to play a role in this business, Robert! You’re not just an inheritance hole!”
The servants scurried away. None of them wanted to be around Mr. Winthrop when he was angry, or he was wont to fire them. Rob didn’t think that was right — he was always nice to his servants. He didn’t even really want to have servants, beyond the security that was necessary for him to be safe — as an heir to a multibillion-dollar company, Rob was always a kidnapping risk. Rob deeply despised his father and used every opportunity at his disposal to humiliate him, so he liked seeing him blush and wince at the sight of his servants pretending not to listen to the argument.
“You ungrateful brat! I built this company so I’d have enough to provide for you.”
Rob scoffed and went to the sliding glass door, beyond which sat the pool. The pool boy was out there. He had brown hair that hung down in a casual, tangled mess around his head. His eyes were bleary and blue, his body lanky, ropy-muscled. He said he played basketball in high school until graduating last year, but he didn’t come across as a jock. Those Chinese characters — or probably-faux-Chinese characters — were visible on his back around the edges of his sleeveless shirt, one of those strappy kinds that barely covered his shoulders at all.
His name was Todd, and Rob had been trying to figure out how get a taste of his dick from the moment he saw him.
“I’m going to stay here and pay that pool boy for his dick,” Rob said. “You can’t make me go to some stupid fundraiser-“
“That’s disgusting, he’s a pool boy, for god’s sake, we don’t even let him in the house! Look at that hair!”
“His hair is glorious. It’s better unwashed and uncombed.”
“I forbid it!”
“Well, stick around and you’ll be able to watch me do it anyway,” Rob said. He stood up and headed for the sliding glass door that led to the backyard. He slid it open. Todd was by the pool, skimming the leaves off the top. His bare shoulders flexed as he dipped and dapped to the beats emanating from the headphones he always wore when working.
“You had better not do anything to embarrass me!” Rob’s father shouted through the door. He banged on the glass.
Rob smiled and waved at him. He went to Todd, who saw him and pulled the headphones down. Todd blushed a little — he was always nervous around upper-class people like Rob and his father. Todd ran his fingers through his confused mess of black hair.
“Hey,” Rob said.
“Hi. I’m just about done,” Todd said.
“Cool, cool…” Rob giggled. “So… Todd… do you have a girlfriend?”
“No.” Then a wry smile appeared on Todd’s face. “Well, there’s this girl, Lisa. She’s… I mean, she’s not a girlfriend. But she’s like…” He blushed. He pantomimed a woman’s hourglass-shape in front of himself. “She’s fucking awesome, man. And she smokes weed.”
“Yeah? There’s nothing better than hot chicks who smoke weed.”
“I know, right!”
“So… Todd… has my dad paid you yet today?”
Todd shook his head. “He direct-deposits it in my account, but not till the end of the day. Actually he never paid me last time, I just asked him about it and he said-“
“I don’t know anything about that,” Rob said. “But maybe I could help. Do you see that cabana over there?”
Todd nodded. He glanced over at the row of cabanas at the far end of the pool.
“Why don’t you go in there and take off your clothes? I’ll meet you inside in just a minute, and I’ll go to town all over your body,” Rob said, smirking at Todd’s blushing face. “In return for that, I’ll give you five hundred dollars. Plus I’ll make my father pay you for last time and this time, because he was probably going to stiff you again.”
“Oh…” Todd’s eyes opened wide. “Oh… wait… Oh…!”
Rob giggled. “Have you ever done anything like that before?”
“No!” Todd took a deep breath. “Wait… I mean… what?”
“Oh Todd… you’re a dumbie. I said I’ll give you five hundred dollars if you cornhole me.”
“But that’s like… illegal?”
Rob nodded. “Yes. That’s correct. This is technically illegal, Todd, I didn’t think I needed to explain that. But yeah, you should say no if you always follow the law strictly. But you’re a stoner, right? Aren’t you stoned all the time?”
“Not all the time.”
“Okay, so you’re not like a law-nerd, right?”
“But I’ll be like a pervert?”
“You could say that. You could call yourself a hustler too, that’s a better word,” Rob said.
“Oh. Yeah, okay! I’ll be a hustler,” Todd said. “Wait, so… you’ll-“
“Oh god, Todd… Smoke less weed, okay? This is a very simple transaction. You’re lucky you’re handsome, because you are dumb,” Rob said with his hands on his hips. “Just go in the cabana and get ready for me to come jack your dick.”
Rob headed for the house, leaving Todd there to ponder what had just happened. Todd looked like he had more questions, but then he just shrugged and went to the cabana. Rob rolled his eyes — the handsome ones were always dumb.
He opened the door. His father had been waiting, watching by the door, but before Rob opened it, he scurried off. He pretended to be cleaning the kitchen — as though he ever cleaned anything himself — and nodded at Rob like he didn’t care.
“So he said no? He’s not into it?”
“Of course he’s not into it. I don’t want him to be into it.”
His father looked at him and furrowed his brow. Then he scowled at Rob. “What? You’re not… ?”
“Dad! I’ve told you so many times, I like rough trade! You asshole!” Rob shouted. His father, of course, didn’t know what rough trade was — even though Rob had explained it before. He thought his father should have paid enough attention to remember that. A part of him thought his father should provide street hustlers for Rob’s amusement — his father had bought a prostitute for Rob’s brother, after all. What was the point of being rich if you didn’t have someone satisfying your every need?
“You act like a fucking teenager sometimes, Robert! You’re a goddamn grown-up!” he shouted. Rob just smile insouciantly and went back outside.
The pool was deserted. Rob strode, shaking his ass for his father’s irate benefit and went to the row of cabanas.
He hadn’t actually intended to point at any specific cabana when he told Todd where to meet him. There were four here, but Rob had rather assumed Todd would go to the first one, the one closest to the pool. But something in his bleary-eyed stoner mind made him think Rob had pointed to the fourth one, the one furthest from the pool.
So at first Rob opened the door and was disappointed to see no one in it. Had he scared Todd off? He hadn’t seem that uncomfortable with it, Rob thought. He’d chosen the word hustler, suggesting he was comfortable with the idea of it, he just wanted a word he could live with.
But then he saw Todd poking his head out of the fourth cabana. “There you are,” Rob said. “Why’d you come to this one?”
“What?”
“No one ever uses this. We only ever use one cabana at a time,” Rob said. “It’s always the first one, just cuz it’s closer to the pool.” He came in and closed the door. It was always warm and humid in the cabanas. No matter the weather outside, it was always a bit warm and very humid in the cabanas, which had a certain smell too — bamboo, Rob assumed, since the inside was lined with it. This cabana had a few old tiki torches too; the servants must have put them here a long time ago (tiki was so gauche Rob would never have allowed a tiki party here while he lived in the house, so it must have been when he was away).
“So why have them?” Todd asked. He sucked in his breath nervously because Rob came closer.
Rob could smell Todd’s intoxicating aroma. It wasn’t a “good” smell in the sense that it was fruity and sweet. It smelled a bit chemical, like chlorine, a bit of bamboo, some cheap almost metallic-scented deodorant and the musky of an early twenties inconsistent-showering slacker. Todd wore a sleeveless shirt, so his biceps flexed as Rob came near and touched his arms. Todd still seemed confused and didn’t react to Rob groping his bicep.
“Huh? Why do you have cabanas if you don’t use them?”
Rob sighed. “What?” He hadn’t really wanted to discuss cabana theory.
“You said you only ever use one of them. So why have four?”
Rob thought for a moment. “I dunno. I guess the builder told my dad that was how many was normal for a pool of this size,” he said.
“It just seems stupid to build more cabanas than you need. Of course the builder is always gonna exaggerate, you shouldn’t just take his word for it-“
“Maybe he suggested ten and my dad talked him down to four,” Rob said. He rolled his eyes. “Why am I defending my father? I agree, it was stupid. We don’t really need any cabanas. They’re just a place for people to change. They could be replaced with one of those Asian folding wall things.”
“Yeah!”
“Are you gonna complain about the cabanas? Or are you gonna make five hundred dollars?”
Todd thought for a moment as though this was a serious debate. Then he shrugged. “I guess I’ll make five hundred dollars. If your dad ever wants to get rid of some of them, tell him he can hire me. I’ll do it for real cheap.”
Rob sunk to his knees. He knew he should just get right to jacking dick. Todd seemed very distractible — he was still talking about cabanas — so Rob thought this would never proceed unless he forced it along. But he also felt a little bad for Todd.
“You know, Todd, you shouldn’t advertise yourself as cheap.”
“What?”
“It makes you seem low-quality. You didn’t demand my father pay you last time you worked, and now you volunteer to work cheap before you even find out how much work the job is? That’s bad salesmanship,” Rob said. He tugged down Todd’s board shorts. “You should try to convince people that this stuff is hard, that they need to hire you and pay you good money to do it. If my dad wants to hire someone cheap, he’ll find an immigrant willing to do it for a half a Twinkie.”
“Really? A half a Twinkie-?!”
“That’s an exaggeration, but yeah, basically. Don’t compete for the bottom, Todd,” Rob said. “And my dad will never pay you once he knows he can get away with stiffing you.”
Todd sighed again, the sound turning into a little growl. He blushed at the realization that his shorts were down, revealing threadbare boxers. He had been so involved in the conversation he had barely noticed Rob pulling his shorts down.
Then Rob got his boxers down too, and Todd’s hefty tan dick popped out. It was thick and juicy, and it twitched even before Rob planted his lips on it. He looked up at Todd, whose face turned bright red as his whole body shook.
“Ah, shit, man… you’re like… serious…” Todd’s eyes opened wide. He leaned back against the wall of the cabana, jutting his hips forward and forcing his still-soft dick deeper into Rob’s mouth.
Since Todd hadn’t even gotten a bit erect yet, Rob had to lick his limp dick. He always thought that was kind of arousing, especially since he loved men so much — they sometimes needed a minute or two to get hard. A lot of them were nervous they’d be unable to get hard without a woman around, but Rob hadn’t yet met one who proved unable to do so.
Todd was no exception. Once he had taken a deep breath and Rob noisily suckled on his dick, Todd let out a little moan. Then his dick twitched again, and again, and it slowly firmed up in Rob’s mouth.
Soon it was as hard as any cock Rob had ever tasted, and Todd jammed it down his throat. He didn’t pound into Rob like aggressive alphas usually did — Todd was more of a gentle slacker than that — but he did ram his dick in, he just did it more obliviously. Rob wondered how often he had been with a female — definitely some, Todd was too handsome to be a virgin, and he had fantastic hair. Surely some ladies had snapped him up.
But he certainly plowed like he had little experience. He was probably just nervous because this was his first encounter like this. His dick awkwardly slipped in and out of Rob’s throat, making him choke and sputter on it. Todd kept stepping back when that happened, like he was used to women who never wanted to gag and would complain if he was impolite.
That wasn’t Rob.
“C’mon, plow my face, it’s okay…” Rob said when Todd pulled away.
Todd’s eyes opened wide and he stammered. “Oh… you’re into that? Oh… Oh…! I see… Oh!” He pushed his dick in again and laughed. “It really feels like a girl, but uh… you swallow dick better than them,” he whispered. He looked around as though people might have been hidden in this tiny cabana.
“I know,” Rob said the best he could as he sucked on the tip of Rob’s dick. “Men always do it better than females, because we have the equipment ourselves. We know what it feels like.” He slammed his own face deep onto Todd’s cock, making himself choke loudly and his throat clench around Todd’s manhood.
Now Todd began to get into it, his inhibitions gradually diminishing because he was hard. Precum flowed down Rob’s throat. It was salty and warm, and it made Rob’s own cock throb painfully in his pants until he took it out. Todd didn’t seem to notice.
“Shit…” Todd’s voice broke, and he chuckled quietly to himself.
Rob smacked his lips as he pulled off Todd’s cock. He thwacked it against his cheeks a few times, making Todd jump each time there was a satisfyingly meaty thwack-thwack sound.
“You ready to stick it in me?” Rob asked, gurgling on the mouth full of precum he hadn’t swallowed yet.
Todd smiled with a flash of excitement first — he didn’t get anal very often — and then nervousness. He had known this was coming, but he was nervous that he wouldn’t do it well. Of course, one of the nice things about being a “hustler” — aside from getting paid — was that he didn’t care how it made Rob feel. It seemed Rob preferred it that way. Todd didn’t need to sweet-talk him like he would a girl, or find a way to be sure this wasn’t painful. He could just bend Rob over and plow into him.
So that was what Todd did, or would have done if he were a more aggressive sort of muchacho. He grimaced a little at the sight of Rob’s ass — it was pale and smooth and perfect like a statue’s. He kind of wished there was something imperfect about it.
But he’d been with women who had hairier asses, and Rob even smelled like a woman (he wore female perfume on his ass precisely to make rough trade of this sort go more smoothly). So Todd grunted and gritted his teeth as he lined himself up with Rob’s backside.
“Oh god!” Rob bit his lip when he felt Todd’s dick slip into him. The pain, as it usually was at first, was intense and mind-blowing. For just a moment Rob considered backing out — Todd’s dick was very girthy — but as usual, that lasted only a moment. He liked his dicks a little “too” thick. He enjoyed the challenge.
Sure enough, with just an inch or two of dickmeat sliding into him, Rob’s pain slowly transformed into pleasure. Todd’s awkwardity made the same transition, as his staccato breathing shifted from sounding like he was on the verge of running away in terror to sounding like he might blow his wad at any moment.
“Shit…” Todd moaned as he began to plow in earnest. He used all of his strength to pound away at Rob’s tight ass, his cock sliding in and out with each thrust of Todd’s hips.
Todd was surprised that this felt so good — he was embarrassed by it too. A part of him worried that this would make him perverted, or at least people would think he was a perv if they knew he did it and really, truly enjoyed it. That was because Rob knew how to use it. He was somehow both loose and tight at once: loose enough for Todd to plow away with all his might, tight enough for there to be a little struggle, and for Rob’s ass to clench around Todd’s cock.
It was incredible. Todd didn’t know anal could be like this. It was enough to, for a moment, make Todd wonder if he could be a hustler as a career — could he find numerous wealthy men like Rob? Probably not, he figured that was likely more difficult than it seemed.
He wondered if he could keep Rob as a consistent lay — this could be a nice little side-income stream, he thought.
As an orgasm exploded deep within him, Todd finally smiled, the last of his reluctance melting away only now that he was done. This, he thought, was a lot less nervewracking than he had seemed. He ran his fingers through his scruffy hair and let out a loud moan that resonated in the cabana.
“Rob!” Rob’s father’s voice filtered through the air. He had been looking in the first cabana — the one everyone actually used — and when he heard Todd’s moan, he realized they were actually in the fourth cabana instead.
Rob orgasmed too. Waves of pleasure emanated from his prostate. The sexiest thing about getting cornholed by young men was that they didn’t even understand the prostate — they just slammed, hard and passionate and intense, and their dick went wherever it ended up, which was somehow always right there on the prostate, Rob’s little pleasure-button, making him gasp and moan and writhe there on the floor of the cabana.
“Robert! Robert Winthrop!” His father was outside now, pounding on the door. It wasn’t locked, but he wouldn’t open it. “Are you trying to humiliate me?!”
“Aaaaaah….” Rob called out and sighed, attempting to say yes though all that came out was a wordless moan. He tried to giggle too, but the orgasm still flowing through his veins made it hard to concentrate.
A surge of fear hit Todd even before his orgasm was even done. He pulled out, heart pounding — was he in trouble with Mr. Winthrop? He hadn’t really considered what would happen if he got caught. At the very least, he thought, he probably lost this client for his pool-cleaning business.
“Don’t worry,” Rob said with a dry chuckle. He stood and stretched his legs. “My dad won’t do anything. He hates me for getting it in the ass, not you for doing it.”
“Oh…” Todd looked down at his limp dick like it had betrayed him. He wiped it off with a towel that was here in the cabana. His cheeks and chest were ruddy and dappled with sweat, both from the sex and from the humid air of the cabana.
“Robert Winthrop! You had better come out of there! I need you getting ready for the fundraiser!”
“I told you, I’m not going unless it’s Spiceman Catering!” Rob said. He crossed his arms over his chest, then realized his father couldn’t see that because the door was still shut. He just shrugged and pulled his pants up. Todd’s panicked expression continued, so Rob added, “and you have to pay Todd! You shouldn’t have stiffed him last time.”
After a long pause, Rob’s father said, “if I pay him now, will you go to the fundraiser? And behave yourself.” He gulped audibly. “Yes, it is Spiceman Catering. But you have to-“
Rob threw the cabana door open. “Why didn’t you say so?” Spiceman Catering was a Sri Lankan catering company whose employees were the entirety of a local semi-professional cricket team, trying to launch a league in the United States. They were all hunky jocks and they had big dicks and marvelous mustaches, and Rob had jacked most of them off at previous black-tie events. They were his favorite catering company.
“I didn’t want you to embarrass me!”
“I won’t! Unless you’re embarrassed by rough trade,” Rob said with a grin. “Oh, almost forgot.” He looked at Todd. “You should have reminded me to pay you. Don’t let rich folk stiff you.” He counted out the five hundred dollars. “And dad, don’t count this as his payment for cleaning the pool. You still owe him.”
“Yeah, fine. Donate five grand to whatever the fundraiser is for, and make sure Adam Patelli sees you do it.”
“Sure, whatever,” Rob said with a shrug. He didn’t care about that part. He had his own goals for the evening.
Ignoring his father, Rob headed into the house to change into a tuxedo. He didn’t like dressing up, but for some studly Sri Lankan caterers, he’d wear whatever it took. He remembered only at the last moment to go back out there and meet Todd before he left, making sure he got paid for all of his pool-cleaning.
It was funny that that was probably what pissed his father off the most. Getting off the poolboy was embarrassing, and getting plowed by the caterer was too — but most of his wealthy buddies messed with the help too. That was expected.
Actually making sure the help was paid? That was beyond the pale.
But Rob did it anyway before heading out for the fundraiser, hoping that tonight would result in another splendid adventure in rough trade.
Read it now for free as an ebook!
Chapter One: Court Fees Got Me Down
Chapter Three: Fraternity Hazing
