Pretty Man

by Ryan Field

  Roland returned carrying five $100 bills. “I really can’t thank you enough for tonight,” he said, handing the money to Josh. “I think we really surprised old Kenneth back there.”

  Josh smiled, reached forward, and ran his palm up the back of Roland’s leg. He squeezed his ass a few times. “I feel kind of guilty though,” Josh said seriously. “I should at least give you something extra.” His voice was low.

  Roland stepped back. “I really don’t expect you to do anything extra. We made a deal, and you fulfilled your end of it. I don’t like taking advantage of people. Trust me; I don’t need to pay for sex.”

  “With an ass like that, I don’t doubt you, man. Maybe I just want to get some of that.” Josh squeezed Roland’s ass hard and smiled.

  “You’re not exactly the romantic type, are you?” Roland chuckled.

  Josh stood up from the settee, leaned back, and pulled down his zipper. A long, thick erection sprang forward. He grabbed it with his right hand and said, “Man, does this look romantic enough for you? I slapped and squeezed that ass of yours enough times tonight to know that I’d like to get a piece of it. Seriously, if you hadn’t offered me money I’d still want to get some of that.”

  Roland smiled. “You don’t have to do this.” The way Josh spoke was a bit foreign; the men he’d been with since his break-up with Kenneth had all been white-collar professionals, either his age or a few years older. They used words like “indeed” too often and smelled like expensive aftershave.

  “I know I don’t have to do it,” Josh said, looking through the double doors Roland returned from and seeing a large bed. “I want to do it. Now go into the bedroom, take off your pants, and lie down on your stomach.”

  Roland laughed. “That’s it? Just take off my pants and lie down?” He’d been with many men, but never one so much younger than himself.

  Josh grabbed him by the waist and pointed him to the bedroom. “You can take off all your clothes and spread your legs a little.”

  The bedroom was a continuation of the sitting area with a king-size bed, white rugs and two mirrored bedside tables. Roland removed his white polo shirt first and kicked off his shoes. When he leaned forward to remove his socks, he saw Josh stripping down. The man’s naked chest bulged with thick, hard muscles. His arms were popped and rounded, and his dick looked huge. Roland stood up again, unbuckled his tan slacks and stepped out of them. He wore a black thong that rode all the way up his ass. He worked out and jogged almost every day, which left his body slim and smooth. He had nice, round chest muscles of his own. But with guys his own age or older, Roland knew he’d always be the attractive, sexy one. With Josh, he wasn’t quite sure how it would work.

  Josh stepped out of his ripped jeans and kicked them off his feet. He had that messy-rough jock appeal. When he looked up and saw Roland standing there in a thong, he said, “That’s hot. You can leave the thong on if you want.” He rubbed his palms together and bit his bottom lip.

  Roland laughed and shook his head. “You’re the boss,” he said, and climbed up on the white bed to slowly rest his stomach against the mattress. He arched his back a little and spread his legs.

  Josh crossed toward the foot of the bed and ran his palm slowly up Roland’s left leg. “That’s so fucking hot. Your legs and ass are so smooth and tan.”

  Roland turned his head to the left. Josh’s legs were strong and muscular and covered with a fine, even layer of dark brown fleece. “I live on a boat in Florida,” Roland said, “and I have my entire body waxed.” The guys he was usually with preferred him smooth all over. “There are condoms and lube in the top drawer over there.” He pointed to a stand on the right.

  Josh climbed on the bed and reached across to open the drawer. He pulled out a condom and tube of lubricant. He covered his hard cock with the condom first, and then squeezed lube into Roland’s ass crack. Roland closed his eyes and sighed while Josh slowly rubbed the lube around the lips of his hole. Then Josh spread one ass cheek to the side, pulled the thong string out of the way, and started working his thick middle finger inside. Roland’s eyes rolled back and he stretched his arms as far forward as they would go. He loved being dominated by strong men; and was always attracted to top men who loved to fuck a tight hole.

  Josh climbed on top of Roland, pressing his hairy legs against Roland’s smooth skin. Josh placed his hands on both sides of Roland’s head and rocked slowly, his huge dick sliding up and down Roland’s ass crack. When the tip of Josh’s cock found Roland’s opening, Roland closed his eyes and spread his legs wider.

  “There it is,” Josh whispered. His cock was solid rock; once the tip was inside he knew he could plunge to the bottom without any problem. When he was all the way in, and his hairy balls were pressed against the bottom of Roland’s ass, he said, “Ah, yeah, man, I knew you’d be a great fuck; you didn’t even flinch.”

  Roland stuck out his tongue and licked Josh’s large hand. Though he’d had big dick before and he knew how to handle it, there was something different about Josh. Maybe it was the age difference: Roland had often fantasized about being with young guys, but had never actually done it.

  Josh fucked slowly at first. He slipped his cock almost all the way out and then hammered deeply. He fucked with his hips only, the rest of his strong body resting on top of Roland. Josh’s thick dick stretched Roland’s hole and rubbed against his prostate each time Josh went deep. When Josh bucked and rolled his hips faster, Roland bent his legs upward at the knee and curled his toes. Josh fucked Roland’s ass with slams so hard and intense, each time his dick went deep it sounded like applause. Pillows slid from the bed. The mattress squeaked. Roland’s head bobbed up and down with such force he couldn’t see straight. Josh just kept pounding and banging into his hole.

  “I’m gonna come!” Josh cried.

  Roland reached down between his legs, pulled his dick out of the thong and jerked himself off while Josh continued to fuck him. He didn’t have to jerk hard. “Go, man,” Roland growled. “I’m close, too.”

  Josh fucked harder. His hairy legs jerked and rubbed against the sheets. He grunted a few times, shoved his dick into Roland as far as it would go, and shouted: “Here it comes! Ah, yeah, here it comes!”

  Roland blew his load all over the white cover at the exact moment Josh filled the condom buried in Roland’s hole. A drop of sweat fell from Josh’s temple and landed on Roland’s cheek.

  “Man,” Josh whispered. “I could stay in there forever. You’ve got a great ass. When I pull my dick out, I want to look at your hole. It’s different from other holes; easy to get into, but tighter than most.” His voice sounded serious and intense.

  Roland laughed. He’d heard that same comment from another man. One guy he met after his break up with Kenneth said Roland’s ass was the closest thing to pussy he’d ever fucked. “I hope I can walk tomorrow,” Roland said to Josh. “At first I wasn’t sure you’d know what to do with that big dick. You proved me wrong.”

  “Dude, seriously, I know how to fuck.” Josh punched Roland hard on the ass.

  Roland squeezed his sphincter tightly around Josh’s cock. Josh’s eyes opened wide.

  “What the fuck was that?”

  “Just a little trick I learned a long time ago,” Roland said. He released Josh’s dick and forced it out of his hole.

  “Can I fuck you again?” Josh asked. “Man, if all my tricks were like you I’d love going to work.”

  Roland laughed and tried to slide out from under Josh’s body. “Damn,” Roland said, smiling, “I can’t move. You really are a big boy. Get off of me so I can get some clean towels.”

  Josh rolled over on his back and lowered his eyes. The used condom hung from his semi-erect cock. The rubber’s tip was filled.

  Roland got up and walked to the bathroom. He returned a minute later with clean, white towels. “I’ve been thinking,” Roland said. “Are you busy this week?”

  “Why?” Josh pulled the used condom off his dick and tossed it on
to the mirrored nightstand.

  Roland made a mental note to flush the condom down the toilet—Russell wouldn’t like finding it there the next day. “I’d like you to be my escort all week,” he said to Josh. “I have to go to these charity events and you can go with me. You’ll stay here, of course, and we’ll start shopping for a new wardrobe tomorrow. I’ll pay you $5,000. All you have to do is stand there and smile.”

  Josh lowered his eyebrows and thought for a moment. His big legs were spread wide and he rubbed his soft, meaty dick with the towel. “If I agree, can I get some more?”

  Roland cocked his head. “Some more what?”

  “Some more of that.” Josh reached around and patted Roland’s ass softly.

  Chapter Two

  Russell walked into Roland’s bedroom early Saturday morning carrying an enormous, silver breakfast tray. He took slow, short steps so he wouldn’t trip on the edge of the thick, white rug. Russell’s smile accentuated the wrinkles along his cheeks and laugh lines around his eyes.

  The first thing Russell saw as he reached Roland’s bed was Josh’s naked, muscular body. The young man was uncovered and asleep on his back, with his big legs spread. His morning erection was so severe that the tip of his penis rested on his rippled stomach. Roland was sound asleep too, though covered from the waist down. His head was nestled into Josh’s shoulder.

  Russell’s entire body jerked back. He gasped, and his hands shook. A small glass of orange juice slipped from the tray and crashed onto the floor, causing Josh to bolt upright and raise his fists.

  “What the fuck?” Josh shouted.

  Roland opened his eyes and jumped up. When he saw Russell standing at the foot of the bed, slack-jawed, he laughed. “Good morning Russell,” Roland crowed. “I guess I forgot to mention that Josh would be spending the night.” He turned to Josh. “Put your fists down. It’s only Russell.”

  Josh reached for the white sheets and pulled them up to his waist. The outline of his erection was still visible through the thin fabric. “Dude,” he said to Russell, “you scared me to death.”

  Russell ignored him. He placed the tray at the foot of the bed and turned toward Roland. “I’m very sorry. I’ll clean the mess right away.”

  “Just leave it until later, please,” Roland said. “We’re fine for now.”

  “I can see that,” Russell said. He looked down at Josh and frowned. Josh sank back into the bed and pulled the cover up higher.

  Roland smiled. “Thanks, Russell. Josh will be staying here this week, just so you know.”

  Russell blinked and opened his mouth, then hesitated. “Thank you,” he said. Russell took one last look at the erection between Josh’s legs and turned to leave.

  When he was gone, Roland reached under the cover and grabbed Josh’s balls. “Poor Russell,” Roland said, laying his head on Josh’s shoulder again. “I’ve known him since I was 17 and I don’t think I’ve ever seen an expression like that on his face.”

  “I don’t think he approves,” Josh said. He spread his legs wider so Roland could massage his balls. “Just because he’s from England doesn’t make him better than me.”

  Roland laughed. “He’s not from England. He just has that proper Park Avenue accent like the old movie stars.”

  “Well, he’s pretentious,” Josh said. His voice was soft and low. The more Roland played with his balls, the more passive Josh became.

  “Not really,” Roland said. “He’s just protective.”

  “Ah, well.”

  “Forget about him,” Roland said. “Let’s teabag.”

  “Dude,” Josh said. “I fucked your brains out three times last night. You want more?”

  “Just a quickie before the day begins,” Roland said. He was silently amazed at his own stamina. He knew a lot of guys his age who took Viagra, but he’d evidently found a completely natural remedy for improving his erection: a good looking young guy with a big, juicy dick. “You don’t have to do a thing. Just lay back and smile.” Though he hadn’t expected to even have sex with Josh the night before, Roland couldn’t get enough of his dick now.

  “You want to wear my dick out?” Josh asked. “This is how I make a part-time living.”

  “What else do you do?” Roland asked. He’d been under the impression Josh was a full-time escort—and possibly a male stripper.

  “I work part-time at the bookstore with Hillary,” he said. “She’s the manager. We’re hoping to buy the business eventually.”

  “Of all the businesses you could buy,” Roland said, “why a bookstore?”

  “We like books, is all.” Josh shrugged. “I left home after high school and didn’t get a chance to go to college. I like to read, though.”

  “Where’s home?”

  “A very small town in Iowa,” Josh said.

  Roland liked that Josh was an avid reader, but was preoccupied with the young man’s balls. He pulled the white cover back to expose Josh’s naked body, leaned forward, and sucked both large balls into his mouth. Roland’s lips protruded and the sides of his face bulged while he rolled Josh’s nuts around with his tongue. Josh closed his eyes and moaned. Roland lifted his head. “Jerk yourself off while I suck your balls.”

  Josh reached for his cock and jerked it slowly. Roland shoved both balls into his mouth again and sucked. He reached down and started jerking his own erection. Roland kept the ball sucking slow and easy, even when Josh jerked his dick faster. Josh’s balls smelled damp and musty because he’d been fucking all night; and tasted salty and tangy. When Josh’s ball sack tightened, Roland looked up and saw that Josh was jerking his dick and staring at Roland. Roland nodded his head and jerked his own dick faster. Josh was jerking so fast now his fist was hitting the side of Roland’s face.

  They came at the same time. Roland blew his load all over Josh’s legs; and Josh blew his all over his own stomach. Roland continued to suck for a few more minutes, until Josh’s eyes were closed and he started to moan again.

  When Roland finally released Josh’s balls, he looked up. “Is your dick okay?” He was smiling, and his lips were red and puffy.

  Josh reached down and ran his hand over the top of Roland’s head. “Never better.”

  The phone rang. Roland reached over Josh’s naked body and answered. It was Donna, a woman from the company that had purchased Roland’s business a year earlier. She wanted to set up a meeting with Roland while he was in town. Since Roland had sold the family business, he’d heard rumors that things were dreadful and his old clients missed him. Sales had been on a downhill slide for months. His family business was always personal; built around natural products and concepts that made women look and feel better. The clients didn’t trust the large corporation that took over. Sales were in a free-fall. Roland didn’t want to see the business he’d spent his life building crumble, but wasn’t sure he wanted to get involved with it again, either.

  He listened to Donna speak, and agreed to meet her early in the week to discuss the possibility of his return as a consultant. He hung up and turned back to Josh. “Let’s shower and get dressed now.”

  He had to take Josh shopping for a new wardrobe so he wouldn’t look out of place at the events for the Ashley Foundation. Roland knew that Kenneth—not to mention everyone else he knew—would be watching them both very carefully.

  Russell had the car ready in front of the house an hour later. He stood on the sidewalk next to the passenger door in a black cap, tapping his foot. Josh was flabbergasted when he and Roland left the house to discover a silver-blue Bentley Continental GTC parked at the curb. The top was down and the pale beige interior looked spotless. He shoved his hands into his pockets and stared at the car the same way Roland had stared at his dick the night before. “I didn’t expect you’d have a car like this,” Josh said. “I expected the typical Lincoln Town Car, black, with tinted windows.”

  “I’m glad you like it,” Roland said. “I wish Russell agreed with you.” He smiled at Russell. “He feels ridiculous
behind the wheel.”

  Russell opened the door for them and smiled. “It’s a very fine car, Roland.” But then he sighed and rolled his eyes. Roland pushed the front seat forward and climbed into the back, followed by Josh.

  Russell sat down behind the steering wheel. Josh leaned forward and tapped him on the shoulder. “You look good driving this car, old boy, a regular race car driver.”

  “Thank you, young man,” Russell said, staring straight ahead. “Where would you like to go?” he asked Roland.

  “Take us to Saks, Russell. I think we can get everything we need there.” He despised shopping and avoided it whenever possible. “We can always stop off at Gucci or Versace afterward.”

  Josh sat back and folded his hands, snickering when he saw Russell put on a pair of black driving gloves. Josh looked at Roland and smiled. Russell slipped the Bentley in gear and stepped hard on the gas, and Josh’s head jerked back. He grabbed Roland’s leg with such force his knuckles turned white.

  “Did I mention Russell really was a race car driver many years ago?” Roland asked as they screeched away from the curb.

  The car sped down West 11th Street. Russell gripped the wheel and leaned forward, concentrating on the road ahead. Josh’s face was white. He held the bottom of the seat with his other hand. “This guy’s a maniac!” he hissed to Roland. “He’s gonna kill us all.”

  Roland reached down and patted Josh’s leg. “Don’t worry. He’s the best driver I’ve ever known. Just sit back and relax.”

  Russell steered the car uptown at a record-breaking pace while Roland patted Josh’s leg reassuringly and Josh pressed both feet to the floor as hard as he could. Russell never looked into the rearview mirrors once; he didn’t turn his head left or right. He just focused on the road in front and plowed through the city with complete ease. The car weaved in and out of lanes to avoid buses and delivery trucks. Taxi drivers threw their arms out of windows and flipped Russell the finger. Old women pulling shopping carts jumped back on the curb. A guy walking two dogs saw the Bentley coming and ran so fast across the street the dogs couldn’t keep up with him. A pretzel vender had to jump up on his stand to avoid being run over. All the lights were yellow. Russell ran them without a second thought.