The Socialite Fuck Club, Part II by Jackson Man

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cw : interracial, slapping, bareback sex

I wanted to use this chapter to focus more on Jack Connor and Santi. It’s slower than the first one but I hope it’s worth it!

Email me with your thoughts at JacksonTheMan@Protonmail.com. I love reading your comments and ideas for future chapters!

Rule #2 of the Socialite Fuck Club

You can’t deny a Top of Color.

Jack Connor sunbathed by the poolside wearing nothing but a Dior swim trunks that his wife bought him. The shorts kept pulling themselves up as he moved until they showed all of his toned thighs, as well as a sizable bulge.

His backyard was large, but messy. A boxwood hedge served as a natural fence between his side and his neighbor’s, but the top was running uneven. His pool was deep with tall stairs, although littered with leaves and other debris. Even his lawn was in need of a trim.

Santiago, a 5’6 Cuban man, exited the small storage shed on the corner. He was wearing a Fruit of the Loom gray tank top that contoured around his torso, highlighting his small pecs and wide shoulders.

The handyman was lean; his short stature and thick eyebrows made him appear as if he was in his early 20s, rather than approaching his 30s like Jack himself. His wavy black hair was hidden beneath a red mesh cap.

“How you doing patron?” Santi asked in a small voice, pulling on his hat slightly. His unbuckled pants drooped, showing polo boxers that were inside out. His dick made a small tent in the jean print.

“Pretty good, bud,” Jack Connor scratched his smooth belly with his left hand and wandered downwards. “How’s your morning so far?”

“Enjoying the show, boss,” Santi said with a slight accent. He licked his lips when he saw Jack push his swim trunks lower, showing his smooth crotch. Santi’s bulging biceps tightened and loosened as he used a shear to tame the hedge. A pool of sweat gathered on his tank top, right under his pecs.

Jack was about to ask Santi to come inside for "some lemonade” when he heard the main door unlock.

Lauren’s voice echoed on his living room as she spoke about her day. Jack heard as bags upon bags were placed on the floor, perhaps $1,500 or $2,000 worth of shopping.

He massaged his bulge while the Cuban man stroke his own cock through his jeans.

“Hello, babe?” Lauren walked into the backyard. Santi returned to gardening out of sight, Jack returned to scratching his stomach. She was oblivious.

“Oh sorry babe, I mustn't have heard you,” Jack started sitting up to greet her. “How was the… gym?”

“Guess who I ran into at the mall-” Jack pulled her in for a French kiss. She let go of herself and jumped into his arms. Jack stared at Cuban handyman the whole time they kissed, and he stared back.

“What was that, you tiger?” Lauren said coquettish before running her hand down his pecs. She rolled her eyes with a hungry smile and turned to leave. Jack slapped her ass on her way out, still having a stare contest with the Cuban man.

“We’ve seen a six percent revenue increase this quarter, sir!”

Andrew Jones roared inside the silent meeting room. His hair was buzz-cut, his beard trimmed and square. The rest of his body was covered with a carpet of curly jet black hair. His smile was large, mischievous, and his white teeth shined bright. “Very, very proud of this achievement, sir, thanks to the management from your son, sir. Let’s all have a round of applause for Jack Connor, people.”

All around him his workers began clapping. Andrew was all smiles, and his sharp eyes looked at Jack’s expectantly, you owe me one.

Andrew gave the slightest node to the redhead and began clapping as well.

Jack smiled humbly. His father, Felix Connor, sat at the head of the table with a satisfied face. He was a very stocky man, who could pass as a bodybuilder trainer were it not for the expensive suits he often wore, being the head of the company. His beard was fuller than Jack’s – redder, too, despite his age.

Eric Goodman kicked Jack playfully under the table. The blond man looked at his friend with soft eyes and his smile was genuine. Jack never felt bigger than now.

“Speech, speech, speech -!” Andrew began chanting from his chair, followed by Eric, then his other coworkers. Sure, Andrew was overselling it now, but Jack didn’t care. He began to stand up to deliver a speech when his father cleared his throat – killing all festivities.

“Good trajectory. Jack, make it eight percent increase by next quarter.” His father’s voice was low and quiet, forcing people to stand still just to hear him.

“Yes sir,” Jack said as he sat back down, almost feeling ashamed. His fifteen seconds were up. Felix called off the meeting and left without speaking to anyone else.

“You know, we have some leisure before the next meeting. We can go to a nearby motel so I can blow you,” Eric said as he checked for a nearby motel during their break. He smelled of a new cologne and Jack couldn’t decide if he liked it or hated it.

“Did you see him? He didn’t even say, congrats son. Nothing,” Jack took a bite out of his sandwich but found himself full. “This fucking suit was two thousands for fuck’s sake. It was supposed to be my big moment.”

“Well, you know your dad – he’s… Quiet -”

“Dad didn’t even- Andrew mentioned it – and you know him, he’s going to want something back in return.” Jack said, then laughed at himself. “Fuck, he gets me so agitated.”

“You sure you don’t want a blowjob, man?” Eric put his hand on Jack’s shoulder and he relaxed. He started massaging Jack’s neck tenderly. “You know, to clear your mind…”

“Maybe…” A car passed by and Jack realized how touchy they looked. “… Sorry I know you’re trying to help-”

“I get it, man. Well, I don’t. Because your dad likes me.”

“Fuck off.”

“Come one, you can’t deny it. He loves me!” Eric teased Jack, who rolled his eyes. He began messing with his hair and Jack laughed. “Besides, you know, if you really want to have him respect you, you have to quit. Show him that you don’t depend on him. That you’re your own boss.”

Jack stared at his college buddy and chuckled. Despite being so beefy from working out, and working as a senior employee in a high-end company, Eric still remained the impressionable twunk he blew back in college.

Eric knew that stare. “No, for real, Jack. I have a plan. Remember the business idea we pitched years go -”

“You know, you got me there for a second,” Jack shook his head. He started getting up as Jack babbled on.

“I looked back at the business plan. It’s legit, bro. The target market as grown, costs have gone down-” Eric produced a packed manila folder from his leather messenger bag.

“Jack, for real. Just runs the numbers. I’m one hundred percent in if you’re in.”

Eric Goodman held Jack by the hand, his skin feeling surprisingly tender. Jack forgot everything about his dad’s disappointment. He realized that he did like Eric’s new cologne.

“… Alright, I’ll take a look for you, jackass.” Eric jumped off his seat and cheered.

The Uber left Jack in front of his house. His Zara jacket hung from his right shoulder, as he had already sweated through his shirt and vest.

A new set of curtains hung from his windows; the main door had a brand new bell. His car was gone – Lauren was probably out shopping.

A new door-mat welcomed his old pair of Oxfords inside. He didn’t have to look at his wallet to know that his wife had probably taken his American Express.

He hung the blazer on the hallway closet neatly. He systematically removed his clothes as he made way into his kitchen. First was his tie, followed by his vest, then his TopMan shirt. He did so until he was left in his Dior boxers.

He took out a six-pack of Heineken from his Samsung Smart Fridge when he heard movement from his backyard.

Santiago was squatting down on the floor as he patted down a new set of flowers on the soil. His shirt was off, his body was soaked on sweat. He lost his cap so his curly hair was out.

His muscles were pumped from working the whole day, making him even look more like a college frat boy.

“Santi!” Jack raised a can to the handyman, pleasantly surprised. “What’s up?”

“Planting this, uh, flowers for your wife, boss,” The Cuban said, his voice low. Jack walked out. The pool was clean, the hedge was trimmed into a new shape. A new row of red and yellow flowers lined on the edge.

“She kept you busy, huh.” Jack eyed the muscles on the Caribbean man. He had a tan from where the shirt used to be. He felt his bulge grow. “The no shirt was her idea, I gather?”

“I think she likes me, sir.” The Cuban gave him a wide smile as he flexed his pecs by bringing both of his buff arms inwards.

“Don’t we all,” Jack laughed and drank again.

Five minutes later both men were inside the storage shed sharing the six-pack. The Cuban remained shirtless, Jack put on a robe.

Santi wolfed down Heineken after Heineken while Santi paced himself. They talked about how their wives loved emptying their account, and bullshitted, but always kept their eyes on each other, waiting who’d make the first move.

“Can I see the invoice for today?” Jack asked while opening his legs. A nice breeze came through. He wanted to run his hands through the Cuban’s chest hair.

Santi simply nodded towards the nearest desk.

Jack walked towards the desk barefoot and the floor creaked. On the desk he saw a weathered notepad with crudely written English. He read the different assignments that his wife gave him.

“She kept you busy the whole day,” He heard Santi’s pants hit the floor and smiled. “Would you mind staying a bit longer?”

Jack turned around and saw the Cuban man sitting on the chair naked. His legs were long, hairy, and toned. His soft dick was hidden beneath an untamed jungle of long pubes. Santi sat like he owned the house and Jack.

“I’m sure we can work something out,” Santi’s accent seemed to grow thicker, like his cock. Jack left the notepad on the desk and made his way to him.

Jack fell on his knees after approaching the Cuban. He began kissing Santi’s hairy legs, going a bit higher with every kiss.

“I think she wants to fuck me, jefe, but I won’t give her that pleasure.” The Cuban man pushed his body forward as Jack kissed his thighs. He was impatient.

“Your wife can be real naggy sometimes, youknow,” Santi’s voice echoed on the small shed. Jack grabbed the 8 inch uncut cock with a single hand. He pushed the foreskin down and began licking the head.

“Yes, sir, she is,” Jack said before putting the whole head in his mouth. Santi slapped him and his cheek burnt.

Santi started removing Jack’s robe. “You too, fucker. I’m here trying to make good money and you’re always looking at me. Showing yourself to me when your wife isn’t looking. Getting me horny. Staring at me while you kiss her. Are you trying to make me jealous?”

“Yes sir, I am,” Jack said, taking a break to get his jaw loosened. Santi took hold of Jack’s mouth and put two fingers inside.

“I’m gonna fuck you bareback. What you think, boss?”

“I’ve been waiting for this the whole day, sir.” Santi removed his wet fingers and slapped Jack’s cheek slightly with them. With every slap Jack groaned and closed his eyes in ecstasy.

“Ride me,” was all the Cuban said. He put both his hands behind his head and leaned backward, relaxing. Jack knew what to do.

He sucked on two of fingers before fingering himself with them. He fingered and opened himself as the Cuban man watched, jerking his cock slowly.

Jack turned around and showed Santiago his pink hole. Santiago spat twice, not missing any time. His weathered hands guided Jack onto his cock.

He worked on breathing deeply and steady to allow the thick cock enter him without lube. At first Santi only had his tip in, so Jack had to grind backwards and forward. This felt so good his own dick started getting hard.

He started riding the Cuban more aggressively. The feeling of being opened up and filled drove him crazy. What Jack loved the most was feeling the Cuban’s unkempt long pubes on his smooth ass. While Jack was smooth and submissive, Santi was hairy and in control.

Santi grabbed him by the hair and pulled his head back. He began kissing the redhead quite tenderly and Jack started grinding at his pace. Santiago ran his weathered hand through the redhead’s hair and beard, caressing his cheekbones before holding him by the jaw and kissing him his neck.

Santi started fucking Jack at his own place. He continuing kissing Jack and moved to kissing his back, and giving small bites. Despite his shortness, Santiago could just hold him down and fuck Jack any way he wanted. Despite being a mere gardener, he could own Jack’s ass in his own house.

Suddenly Santiago pushed him towards the floor. Jack obeyed instantly and got in all fours.

“Ass to mouth, let’s go.” Santi said. He had both his hands on his hips, waiting impatiently.

He turned around and knelled. The wooden floor felt too rough against his knees. He hoped he wouldn’t get any bruises.

Jack stared at the 8 inch dick that had just been in his ass. The foreskin covered almost all of the thick head. Jack began kissing the man’s crotch, thighs, balls. He breathed in the smell of his pubes, completely wanting to serve Santiago.

“Suck my balls,” Jack moved on to licking the Cuban’s man low-hanging balls as Santi began jerking himself off. “You think your wife will like the way I taste in your mouth?”

He thrust up slowly, grinding his balls on Jack’s face until his beard and even eyebrows became a mess.

Santiago made it inside Jack’s lips fast enough to not let a drop go to waste. He shot 5, maybe 6 times. Jack felt it in his tongue, filling his cheeks. Even after Santi was done shooting he still fucked Jack’s mouth, spreading his nut around.

He let go of the American with a pleased exhale. Jack swallowed everything and stuck his tongue out to show it bare. Santi smiled and slapped his face pleasantly.

Despite being half a foot shorter Santiago seemed bigger when standing up. Jack remained on his knee, jerking himself off.

“Sit on the sofa,” Jack obeyed and sat, his dick glimpsing with precum. The Cuban grabbed Jack’s cock slowly, teasingly. The pink head was completely soaked. He drew a circle with his finger nd Jack moaned.

He jerked the redhead slowly. With his free hand he grabbed the back of Jack’s head and pushed it into his pecs.

Jack loved his smell. His pecs were firm and small, but the hair so thick. He brushed his face against the chest hair back and forth. He licked, then sucked on Santi’s right nipple.

Meanwhile the Cuban increased his pace despite his muscles beaten from working. He edged the redhead until he ended up shooting all over his belly and torso. Santiago picked some and fed it to him with his fingers.

“You’re gonna brush your teeth before kissing your wife?” Santi slapped Jack’s cheek slightly as Jack smiled with contend. Still in ecstasy and lost, Jack had to gulped a few times before answering.

“No, sir.” The taste of Santi’s cum lingered in the back of his throat.

Santiago slapped Jack’s thighs a few times while shaking his head in disbelief, laughing. He started putting on his pants without his boxers and said they were a gift to Jack. Even when soft, his dick and balls made a bulge.

It was 9pm when Jack made it to the restroom.

He stared at himself in the mirror as the tub filled. His beard was messy and tangled, and his hair unkempt. He noticed that his chest hair started growing on his abs and knew it’d be time to shave soon.

The biggest eyesore was the large hickey on his neck, right on the spot Santi began kissing him. Fucker knew what he was doing. How could he hide it? Would he hide it?

From downstairs he heard his wife get home. He wondered how much she spent this time. Between his suit, his wife and paying Santi he probably spent almost $8,000.

The tub was done filling. He sighed deeply and reached for his XS Max. He scrolled through email notifications, Instagram requests, a missed call from Andrew Jones – Eric had also called, then texted him.

He thought his talk earlier. Perhaps extra income couldn’t hurt. And if he didn’t increase profit by 8% by next quarter like his dad ordered he might need a second job.

He typed a two sentences and sent them to Eric.

“Find. I’ll take a look at your project.”

Eric called just as Jack he put his phone in Do Not Disturb. He chuckled to himself as he stepped into the lukewarm water, ignoring the call. He wondered how many times Eric would call before just driving to see him.

Jack Connor submerged himself in the tub and held his breath. Partnering up with Eric made him feel like back in college. He hoped there'd be as much fucking now as there was back then.

To be Continued.

I hate writing MacGuffins but that’s what Eric and Jack’s business is going to be.

Sorry for so much plot. I know, I know- most people don’t care. I just like having a good backdrop for the intimate scenes. Next chapters won’t have this much plot. I just had to move Eric and Jack’s story forward.

Let me know what you think/what you’d like to see at JacksonTheMan@Protonmail.com