The Stripper

Lemond is a stripper who needs a break… and a few extra dollars! Avery is glad to help out in return for a swing on Lemon’s huge throbbing slab of mahogany meat!

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Avery had never been to a high-class bachelorette party. It was not at all what he expected. The bride-to-be was Daphne Jardine, a wealthy heiress to a chandelier fortune. Avery didn’t know her that well — she was just a friend of a friend whom he saw often at parties — but she had insisted he come. Avery only agreed because he hoped to see a stripper. Avery was a great admirer of the male form, and strippers often had incredible physiques.
When he arrived, however, at Daphne’s ancient mansion, Avery decided that wasn’t going to happen. This wasn’t that sort of party. People who owned mansions like this didn’t hire strippers. He didn’t realize Daphne was this rich.
A butler showed Avery to the party, which consisted of a half-dozen women drinking champagne. The decorations were present, everywhere, scattered expertly, chic and expensive, covering every part of the mansion, but they had a certain soulless quality — Avery could tell that some servant had put them up, not someone who actually wanted to attend the party. There were streamers and a golden goblet for the bride to drink out of, and the giftbag included a skin cream with actual diamond dust in it.
“Oh my god, Avery! I’m so glad you’re here!” Avery’s friend Mandy hugged him. She whispered in his ear, “Oh my god, Daphne has such a stick up her ass, it’s… like a whole tree.”
“Woo, we’re partying! Let’s bring out the cake!”
“Yeah! Oh my god, Daphne, do you know what your fiancé is doing tonight?”
Daphne sat, skeletal and grimly smiling — she was skinny and well-manicured, with brittle hair and a saccharine smile — and shaking her head. “I don’t know, he wouldn’t tell me what men do on their bachelor parties.”
“You know what they’re doing…” Avery said with a laugh.
Daphne shot him an angry look. “I told him no stripper, if that’s what you’re implying, Avery. We are remaining loyal to each other. He wouldn’t do that to me.” She shuddered.
“Okay, sorry….” Avery murmured. He rolled his eyes. The putative stripper was the only reason Avery came.
But now, it seemed, she was opposed to strippers. As a servant of some sort — some sort of “games maid”? Avery didn’t know — brought them out a game to play, Avery considered leaving. This felt more like a child’s birthday party thrown by the servants than a real bachelorette party.
The music playing, Avery realized, was a nocturne by Chopin. What kind of bachelorette party played classical music?
The game was essentially Duck, Duck, Goose, but with little penis-shaped cookies — it might have been fun with a bunch of silly girls, a male stripper and enough alcohol that they were all drunk before beginning the game. With just Daphne and some other haughty bitches, none of whom would drink enough to get tipsy much less drunk, the game was a somber, annoying diversion.
There was a knock on the front door — the cavernous main hallway had an echo, so the knock was audible even in the party. Everyone turned to look at Daphne, but she just said to wait. “Velma will answer the door. I believe this is all the guests, right? Are we missing someone? No one else was invited.” Daphne furrowed her brow.
Avery sat in grim silence. No one wanted to start the next round of this utterly idiotic game knowing that whoever the new partygoer was would interrupt them momentarily. Avery looked among the women here — who was missing? Most of these women showed up to parties together, that was how Avery knew them. Mandy was an associated hanger-on who used to work with Daphne at her feminist bookstore, and she was how Avery came to know Daphne and the others. Now Mandy’s eyes twinkled in Avery’s direction.
The door opened, and in walked a tall, broad-shouldered black man in a fine suit. He had dimples like LL Cool J and light brown skin, with a broad chest that barely fit in the suit. It was a plain navy blue suit with an impeccable alabaster tie. He walked with swagger and a thick jaw, and the bulge in his pants attracted Avery’s eye.
“Daphne Jardine?” he said. He had a clipboard in hand.
“Yes.”
“You’ve been served,” he said. He handed over a stack of documents to her.
Daphne’s face turned into a bitter scowl. “I’m being served! You asshole! It’s my bachelorette party! How dare you?!” She called out of the room. “Velma! How could you let this man in? He’s not from the party! Velma! I swear to Christ, I’ll have your son deported-!”
“Daphne, wait! Wait!” Mandy got up and went to her.
But Daphne was in a rage, screaming at Velma in the hallway. Velma quaked and backed away from her. “Don’t tell me to wait, what is this? Is it that jerkoff from the City Council? I told him I read the code, his patriarchy won’t bring me down,” she said to the black man who had served her with papers. His eyes were opened wide like he was shocked she was upset. Daphne wagged her finger at him. “Are you a real process server? I’d like to formally dispute that I was properly served-“
“Daphne, what are you being sued over?” Mandy asked with a big grin on her face. She pointed to the papers in Daphne’s hand.
Daphne sighed and shook her head. “The city council has a bee in its bonnet about my store. They’re claiming that a bookstore is a Class D commercial establishment, but the definitions provided in the zoning code make it clear that Class C is the more appropriate fit. That’s for retail stores that aren’t everyday shops like gas stations. The examples given in the city code include a CD store — the zoning guide was written in the 90s — which is pretty much the same thing as a bookstore, right? Why would it-?”
“Daphne, look at the papers,” Mandy said, exasperated.
Daphne nodded and glanced at them, but it was obvious she was too worked up to really process what she was reading. She looked at the black man. “You! What are you still doing here? This is a private function, and you’ve done what you were hired to do, you jackal! You court-sponsored… hound!” Her face was ruddy, veins popping against the skin of her neck.
“Hey, lady, relax,” the black man said with a sigh. He straightened his tie.
“Daphne! Read the goddamn papers!” Mandy said.
“Now? I have lawyers for that, Mandy,” Daphne said. She finally looked at the papers and read the words. “I’m being sued for… improper use of party-related materials and utter craving for mahogany manmeat. What does that mean? I don’t use mahogany, that’s endangered, I would never do that! This inaccurate accusation will not stand! I’m being persecuted!” It was apparent she was still worked up because she said manmeat like she didn’t recognize it. She looked up. “I will be contacting the National Organization for Women and-“
The black man looked at her. “That’s right, but don’t worry, I’m here to work on both of those charges with you! I am… the Mahogany Miracle!” He shrugged his suit jacket off, and Mandy squealed, followed by the other girls, at the sight of his incredible shoulders straining against the tight fabric of his button-down shirt.
Mandy pressed play on an app on her phone, and the sound of pulse-pounding hip hop filled the air. Avery hurried to turn off the Chopin, though no one could hear it anymore.
“Wooooooh!”
“Oh my god, that’s so crazy!”
“He’s a stripper!!!!”
Finally it began to feel like a real party. The Mahogany Miracle — who later said his real name was Lemond — took his tie off and wrapped it around the back of Daphne’s neck like a lasso, and he pulled her closer to him as he danced. He puckered up as though to kiss her. He had good instincts though, and when Daphne frowned a little, he let go — obviously she didn’t want to kiss him. She was still fuming about the City Council’s zoning regulations.
So he kissed Mandy instead. She was coming up behind him, pretending for the benefit of the other girls that she was going to grab his ass. Then he turned around, took her in his arms and plowed his tongue into her throat and they swooned together like the hero of some romance novel.
Mandy squealed and grabbed at Lemond’s back. His shoulder muscles barely fit in that shirt, which looked like it could pop right off.
“Woo-hoo!” Avery danced with some of the more demure women, hoping to get the party going. Most of these women were too high-class to have ever seen a stripper before, and Avery thought they’d be more comfortable with it if they started off dancing with him.
“Dance with him!”
“Avery! Avery! Avery!”
Avery hadn’t even realized that some of the women were chanting for him to get the next dance — Lemond the Mahogany Miracle was surrounded by Mandy and a few other relatively bold women, while Avery and the other prudes danced in the other side of the room. Now they all began chanting for Lemond to come to him.
At first it seemed Lemond would refuse, that he would say he didn’t dance for men. But then he shrugged, took one step and ripped his button-down shirt off, buttons flying across the room. One button landed in Daphne’s glass of champagne, and she squealed in both shock and delight.
“Oh god…” Avery murmured to himself. Lemond had an impeccable chest, with big mountainous pectorals and a six-pack more perfect than Avery had ever seen. He looked good in his slacks, a big bulge plainly visible in his crotch. His chest was smooth, unblemished, gleaming with a few beads of sweat that had collected there as he danced.
Avery blushed and pantomimed a fishing rod, as though he had lured Lemond, who grinned and played along — neither could speak because the music was too loud. Lemond shimmied over to him, and leaned back to outstretch his chest.
“Body shots!” Avery shouted, and got on his knees right in front of Lemond. He put his tongue out, touching the firm flesh of Lemond’s waist just above his pants, while Mandy poured a bottle of champagne onto Lemond’s chest, so that it ran between his pecs and poured directly into Avery’s mouth.
“Hell yeah!”
“Body shots! Oh my god!”
That helped loosen things up. Avery was glad for that; it felt more like a party now, even if Daphne herself seemed glum. The girls took turns taking body shots off his chest, until those slacks were soaked with champagne.
Then he ripped the pants off, revealing his trunk-like thighs, toned calves and the sausage-hugging banana hammock he wore over his cock and balls. Avery’s jaw dropped — he had never seen such a huge package before. The banana hammock briefs were much too small for him, just like the suit, and if he hadn’t shaved it, most of his pubic hair would be visible. As it was, his heavy cock and balls weighed down the tiny spandex material so much that the root of his shaft was visible.
Mandy took her body shot with her tongue out, running over the round bulge of his cock through those briefs. The girls all squealed and clapped.
It was shocking, Avery thought, how the presence of a handsome stranger changed these women’s willingness to do stuff — he was quite sure that most of them had said they didn’t suck dick at a party last year — they had said oral sex was “oppressive to women in developing nations”; they certainly didn’t lick some stranger’s cock.
And now here they were, kneeling while a man whom none of them knew dragged his dick over their faces.
He was really very handsome, Avery thought, Mandy had chosen well. He was dimpled and charming when the music stopped, with a lilting, smooth voice. He came across like the streetwise older brother on a Nickelodeon kids’ show.
Finally, he let Daphne take that banana hammock off. She gingerly squealed, giggling, blushing, halting several times as she stuck one finger under the fabric and pulled it down. His thirteen-inch cock popped out, limp but meaty, and it slapped at her wrist.
“Oh my god! It felt like a leg of lamb!” Daphne screamed so loud that the “games maid” came to make sure everything was alright. Daphne held her hand up as though they were going to worship any body part that had touched Lemond’s body.
At last, the bachelorette party continued apace, and Avery felt right. Lemond flopped his dick all over Avery’s face — most of the girls hadn’t quite taken it that far, but Avery made it clear he’d love to. He even stuck his tongue out, chasing Lemond’s shaft as it heavily slapped him all across the face.
“Hmmmm… I’m not s’posed to let you lick it,” Lemond said with a wink. “My agency has a rule against that.”
“I just stuck my tongue out,” Avery said. “I wasn’t trying to lick it, it’s not my fault your dick keeps moving around all over my tongue.” He blushed, running his tongue from the root to the tip before Lemond moved on.
By then, some of the girls had passed out, or were nearly there. Even Daphne was half-asleep. Most of these girls didn’t really drink very often. A few glances of champagne was enough to make them sleepy.
Soon enough, the party was over. It happened quickly once it got closer — every time somebody passed out or called for a rideshare, there was one fewer person actually partying, which made the others more and more tired. Even Daphne “retired to her bedroom” with a guilty look on her face that suggested she was going to fuck herself with a dildo until she could forget about Lemond.
The only people left were Avery, Mandy and Lemond, and with the music off, all they ended up doing was sitting around and talking. Mandy was drunk, but neither Lemond nor Avery had had anything to drink. Lemond rolled them up a blunt with the weed Mandy had brought.
Before he lit it though, Mandy begged off. She said she had a headache and thought the weed would just make her throw up. She told them to go ahead and smoke it though.
Lemond talked about his career as a rapper as he lit it and passed it to Avery, who was entranced by that fat cock sticking to his thigh. Lemond, as it turned out, was more realistic than most of the aspiring rappers Avery had met — he wasn’t trying to be a gangsta, he didn’t care about street credibility at all — he was a kid’s entertainer. He had released an album of songs about counting, letters, body parts and colors. It had done well, he said — he didn’t make much money, but he was about to go into the studio for a follow-up, and this time, he had a much better contract.
“But for now, you know, I still gotta strip to make ends meet. This month is tough,” Lemond said. “There ain’t a lotta call for strippers in March. It’s been a dry spell.
“Oh that sucks,” Avery said. “I wish I knew of some more parties coming up you could strip at.”
Lemond shrugged. “I’ll figure something out. Lemme know if you get an idea,” he said. He handed over a business card. Then he sighed. “I guess I should go. Technically they hired me for another twenty minutes, but…”
“I… I have an idea,” Avery said. He licked his lips and looked at Lemond. “If you stick it in me, I’ll give you five hundred dollars.”
Lemond looked at him as though his knee-jerk reaction was to say no. Then he shrugged. “Make it eight hundred.”
“Fine.” Avery considered haggling, but he could afford it, and Lemond had been so charming, he didn’t want to nickel-and-dime him.
Lemond sighed and leaned his head back as though this was a huge imposition and he was exhausted. Avery wondered for the first time if he had been working up to this — was he a hustler? He had been hesitant, yet willing, to dance for Avery all night, and now he was hesitant yet willing? If shaking his ass for Avery had been uncomfortable, why would he agree to plow into him? Lemond grumbled a bit, but it was too realistic, like Lemond knew the best way to get more money was to pretend he needed to be convinced to do it.
Oh well, Avery shrugged. That was part of being into rough trade, he thought, sometimes you got hustled.
“Your cock is so big,” Avery said as he picked it up with one hand. He sunk to his knees between Lemond’s legs, while Lemond lit up his blunt and took a deep drag off it. The fragrant smell of weed filled the air. Lemond’s dick was so big Avery couldn’t wrap his fingers all the way around it. “It’ll be a challenge to swallow.”
Lemond snorted. “You can’t deep-throat it, no one can,” he said like he hated having a big cock. But a smile flickered over his lips too.
“Well, I can’t wait to try,” Avery said. He let the tip fill his mouth. There was still a good ten inches of dickmeat left to slurp on, but Avery just focused on the tip at first.
“Man… I can’t believe I’m lettin’ a man jack me off,” Lemond said as he smoked on the blunt. “I ain’t like that, you know? Don’t fall in love with me. I can’t look, I gotta cover my eyes.” He leaned his head back and put one of his forearms over his eyes. He left enough room for him to keep smoking on the blunt.
Avery had to roll his eyes. This had passed the point of believability — Lemond was too focused on smoking weed to lie effectively. If he was really this nervous about being with a man, he wouldn’t be ignoring Avery to smoke the blunt. Who got off from a man for the first time, made a big deal out of it and then ignored it to smoke some weed?
But Avery wasn’t going to accuse him of being a hustler. He was plenty handsome, after all, that wasn’t a trick.
His dick firmed up in Avery’s mouth, but it was too big to really get hard without some serious deep-throating. Avery took a deep breath and used his own fingers to pry his jaw open the best he could. He let that massive rod slide down him.
“Damn, I never had a man jack me off like that,” Lemond said with a sigh. “You really get deep.” Then his whole body startled and he blurted out, “I mean, I never had a man jack me off at all.” He laughed nervously. “See, uh… Cuz it’s my first time.” His eyes opened wide as a visible shiver of pleasure ran up his spine. “Goddamn… You can get awful deep on there…”
Avery was an expert at swallowing dick. He had been practicing on loosening up his throat for years — he did exercises daily — and was glad to see that was paying off. He pulled off and hocked up a big mouth full of spit. Lemond watched with a cocky grin on his face. Avery moaned through the moisture in his mouth, murmuring, “Hmmm… I wanna taste your whole dick in my throat…”
Lemond licked his tongue. The clue was in his mouth, Avery saw, which was grinning and pursed, excited, glad to get a nice mouth, while his eyes showed the shock he was trying to display — he was a good liar, it was just hard to lie with your mouth. Lemond’s eyes had never been jacked off by a man, but his mouth was a hustler.
Saliva slid down his shaft as Avery slammed his head down. He choked but kept going, hands roaming up to Lemond’s gorgeous pecs. Soon he gagged over and over, producing more spit that helped lube up Lemond’s throbbing manhood, and his nose pressed into the shaved skin of Lemond’s crotch.
“Goddamn, holy fuck, you’re — shit!” Lemond’s voice broke, and he writhed on the chair he still sat on. His muscles all flexed and he grunted loudly. He dropped the blunt on the floor. Thirteen inches of stripper manmeat flooded Avery’s throat, stretching it and making him sputter. His jaw was sore.
Though Avery’s mind cried out for oxygen, he didn’t want to stop just yet. He didn’t mind his lungs desperation or the heaving, retching his body went through. The fact that this was slightly painful just made it hotter, he thought, and all the tension in Avery’s body was in Lemond’s too as he approached his orgasm. The only difference was that Avery’s lithe body twisted, while Lemond’s thickness flexed and firmed up. Lemond gasped and shifted around on his chair. Soon he was literally on the edge of his seat, licking his lips, gripping Lemond’s ears to keep his face angled the right way.
At last, Avery pulled all the way off and gasped loudly, hoarsely, for air. He grinned at the shocked look on Lemond’s face. “Hmmm… Your dick tastes so good.”
“I know, baby.”
“You wanna stick it in me?” Avery said. He turned around, still heaving for air and dizzy from lack of oxygen. He showed off his bare ass, lowering his face to the floor. “C’mon, I wanna feel you inside me.”
“Hell yeah, lemme in there,” Lemond said. He wedged his dick between Avery’s cheeks. “You feel how big that is? Huh? You gonna take that whole thing in there? I bet you can.”
“I can… You won’t be gentle, will you?” Avery asked with a giggle.
Lemond chuckled. “Not if you don’t want, baby,” he said. He aimed his dick for the hole as he smeared lube over the shaft — he had apparently brought his own lube. He bit his lip and slid the tip in. Avery grunted and tightened his body instinctively, before taking a deep breath and relaxing it. He sighed. Lemond slapped one asscheek, then he grunted like he had forgotten he was supposed to be reluctant.
“Shit, you as smooth as any female, I like that in a man-” he winced and cut himself off again. “Not that I ever did it before. I like — That’s why I was, y’know, reluctant, I wasn’t sure I could handle a man’s ass. That’s all.”
“Uh-huh. Cuz… it’s your first time?” Avery said with a tense giggle. He had to suck in his breath to relax his ass more and more, as that entire thick shaft slipped in deeper and deeper. “That’s good lube,” Avery said between gasps.
“Yeah, it’s Shaft-Slipper, you ever heard of it? Good stuff, it’s what I always bring to shows.” He paused. “With women, I mean. Women pay for, you know…” He shuddered and his voice broke. His dick was all the way in now, all thirteen inches throbbing in Avery’s ass. Lemond backed his cock up, slowly at first as he began gyrating his hips.
“Women pay you for anal? You’re an… anal gigolo?” Avery giggled. It was getting easier to concentrate even with that forearm-sized cock stretching his asshole, and he felt thin slivers of pleasure flowing through his veins.
“Uh… Yeah. Yeah, some of ’em, uh… really love anal,” Lemond said.
“I… don’t believe you,” Avery said, his voice hoarse and breathless. He slid his ass back on Lemond’s cock. “You cornhole men for money all the time, right?”
Lemond smirked but shook his head. “I swear, you’re my first.”
Avery rolled his eyes. “No woman pays to get fucked in the ass by a thirteen-inch cock.” He grunted, reaching behind himself to guide Lemond’s dick in and out. “Only a man would ever do that.”
Lemond grumbled without answering. He wrapped one of his massive biceps around Avery’s head, so Avery’s face was ensconced in his stone-like muscles. His other arm held Avery’s ass firmly in place. “Women love me,” he said, ramming his dick in, the entire shaft in one motion that made Avery howl with pleasure. “They’ll pay anything for my meat…”
Avery’s cock throbbed, precum dripping onto the floor. Avery’s hands flailed, the sensations coursing through his body so intense he couldn’t even jack himself off. He was impaled on Lemond’s rock-hard shaft, and the best part was how Lemond seemed distant now, moaning, groaning, but still just heavy breathing into Avery’s ass — was Lemond really enjoying this that much or was he exaggerating for Avery’s benefit? It was impossible to be sure. Avery squirmed in his arms, gasping, licking, sucking all the sweat off his body.
“Hey… I really need the money, man,” Lemond said. He whispered directly into Avery’s ear. “I’m desperate. You wanna gimme another five hundred bucks? I’ll admit it, you were right, I’ve stuck men before. I’m not proud of it, I just… I need the money, and I need it now.”
“Oh god, stick it in me!” Avery slammed his own ass back and forth the best he could, but he was curled up in Lemond’s arms. Lemond was motionless right now, his cock standing up straight within Avery’s ass. Lemond breathed heavily, his hot air condensing on Lemond’s ear.
“I will. I want to. For five hundred dollars… I’ll do something nasty,” Lemond said. Then he whispered right into Avery’s ear as though it was a secret. “I’ll give you a reacharound and let you kiss me for five hundred dollars. That’ll be thirteen hundred total. No checks.”
“Okay, yes! Yes!”
“You got cash?”
“Not with me! Not all of it! I swear, I can get you the rest! I swear! Do it!”
“Don’t mess with me, man, I’ll mess you up, and not in a way you enjoy,” he said.
“I won’t! I’ll pay!” Avery felt tears in his eyes. He wiggled this way and that on Lemond’s crotch, but he couldn’t move forward or back because Lemond’s powerful arm held him in place.
Lemond thought for a moment, then sucked on Avery’s earlobe and said, “Fine.” He turned Avery’s head to the side, planted his lips on Avery’s and his tongue invaded Avery’s mouth. At the same time, his hand wrapped around Avery’s cock and gave it a stroke.
Avery had never felt anything like this. He had been swallowed up by Lemond’s massive body, and all he could do was take it. He’d never taken dick like this. Lemond’s tongue explored his mouth, while his hand expertly ran up and down his shaft. Avery’s fingers clawed at his stone-like body, which Lemond ignored.
The most intense orgasm of his life smacked into Avery like a train. He would have cried out loud but his mouth was clogged with Lemond’s tongue, so all he did was whimper. His ass loosened, then clenched tightly as Lemond plowed in.
Cum flew over Lemond’s fingers and onto the floor. Lemond had been holding off on his own orgasm, wanting to make Avery cum first — he’d been doing this often enough he had remarkable control over his cock. Once he felt that first spray of sticky cum on his hand, he rocked his hips back and forth a few more times and let his orgasm happen.
Avery shuddered and sobbed — he’d never cried during an orgasm before, but the pain in his ass was so intense he couldn’t help it, even if he didn’t feel the pain — he was aware it was there; he couldn’t help but be aware of the biggest dick of his life throbbing in his ass — it was like a distant pain that was happening to someone else, and Avery could sense it but not experience it.
Instead, he experienced an orgasm. Red-faced and panting, he accepted every drop of Lemond’s load as he begged for more. Avery felt cum trickling throughout him, Lemond’s sticky wad jetting into him deeply, seeping into his flesh until Avery could feel it all over.
His tongue slathered spit over Avery’s face, which was a little sour and salty because he had been slurping on Lemond’s dick earlier — Lemond didn’t like that, but he’d done this often enough it didn’t bother him as long as it was his own precum. He did gag at the taste, but he knew that just turned some men on even more. When he gagged, his broad chest muscles all flexed against Avery’s smooth back.
At last, Avery fell limp, and Lemond knew that meant he was done. He backed up slowly, grimacing at the sight of his shaft stretching out that tight hole. It was full of cum, which seeped out and coated Avery’s ass.
“Shit…” Lemond said with a dry chuckle. He slapped Avery’s cheek. “I’m glad I did that, even if it was… y’know, gross.”
“Right.” Avery was breathless. “And it was your first time.”
“Uh-huh.” Lemond stood. He wiped his dick off and put his pants back on. He didn’t bother to put his pants on too. “I’m all done, man, I’m off. So… I’m leaving.”
“Okay, cool,” Avery said. “Thanks for the dick… Your first time.”
“Right, yeah, first time. I jacked off a man,” Lemond said absent-mindedly. He wasn’t really trying to lie effectively now. “Gross. That was gross. Cuz I never did it before.” He sighed as he got dressed. “You gotta get your phone out.” He snapped when Avery didn’t immediately jump into action. “You got PayUp, right? Go get yo’ phone. You best pay me. Lemond always gets paid.”

The Poolboy

Rob’s got a hunky poolboy named Todd, and he’s got enough cash to get Todd’s pants off. Can he satisfy Todd’s throbbing young alpha needs?!

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Rob Winthrop clicked 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 poolboy 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. Rob had an app that was supposed to identify them, but he couldn’t get a good enough picture. Or maybe the app was crap.
“Yes, 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.” Rob was vegetarian for about three weeks back in high school. He gave it up because his dad was oddly supportive of it. It was a pitiful rebellion, and Rob winced every time his dad reminded him of it.
“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 poolboy 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 hang out with the poolboy,” Rob said. “You can’t make me go to some stupid fundraiser-“
“That’s disgusting, he’s a poolboy, 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 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 — 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. 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. “Tits like sirens on an ambulance, dude. 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 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 you off. I’ll give you money.”
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 that Rob was jerking off the help. Rob knew it bothered him though. He just stopped complaining because he was smart enough to realize complaining made Rob do it more.
“So he said no? The poolboy had enough class to turn you down?”
“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. “You act like a fucking teenager sometimes, Robert. You’re a goddamn grown-up,” he snapped. 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 seemed that uncomfortable with it, Rob thought.
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 musk 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 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, rolling his eyes. He didn’t mean to get involved in the economics of the pool-cleaning business, but he was on a roll now. 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 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 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. The smell of Todd’s musty crotch, liberally seasoned with chlorine, hit Rob’s nostrils.
“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, Rob liked it when men 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. Rob could get any man hard.
Todd was no exception. Once he had taken a deep breath and Rob noisily suckled on his dick, Todd let out a moan. Then his dick twitched again, and again, and it slowly firmed up in Rob’s mouth. It was long and throbbing, and the more it firmed up the more Todd sucked in his breath like he couldn’t decide if it hurt or not. Or maybe he thought he wasn’t supposed to moan, so he kept suppressing them when Rob’s mouth sent shivers of pleasure up his spine.
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 at Rob’s throat like he had little experience. He was probably nervous because this was his first encounter like this, Rob decided. 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. Rob never complained about an aggressive throating.
“C’mon, plow my face, force it down my throat, it’s okay…” Rob said when Todd pulled away. Long tendrils of spit still connected Rob’s lips to Todd’s cock.
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. “You go, like, way deeper. Waaaay deeper.”
“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. Todd’s tautly muscled chest rippled, and his eyes opened wider.
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 as deep as he could manage. It didn’t even matter if he came too quick.
So that was what Todd did, or would have done if he were a more aggressive sort of muchacho. He grimaced 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 encounters of this sort go more smoothly). So Todd grunted and gritted his teeth as he lined his cock up with Rob’s backside. He used both hands to spread Rob’s asscheeks.
“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, it seemed maybe embarrassing to be that into it. Todd wasn’t an ex-con, after all. It felt so amazing because Rob knew how to use his ass. 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 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. Plus they’re probably all into black guys.
He wondered if he could keep Rob as a consistent lay — this could be a nice little side-income stream, he thought. Plus when he was unable to get laid… It would be convenient to both blow a nut and get paid.
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 best 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 exertion 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! I’ll be as discrete as possible,” 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. Rob’s mother was fucking her tennis pro, and everybody in the Western Hemisphere knew it.
Actually making sure the help was paid? That was beyond the pale for the Winthrop family, or at least the older generation of it.
Rob, on the other hand, was already figuring out how much cash he’d need to bring to nab an entire cricket team’s worth of Sri Lankan man-meat.