Gay Summer Holiday

If you think you found the biggest dick around, you always find a larger tool to play with. Chris found himself a lawyer with some thuggish friends. As rough and nasty as the encounter became, Chris got the better end of the deal. And new colored friends to play with, too. That, and the new tools to complete his working holiday on the Island.

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 ⁕ Disclaimer:
This story is strictly fictional and contains male-on-male (gay 🏳‍🌈 ) sexual content, both implied and explicit. 🔞 Reader discretion is advised. The names, ages, circumstances, parties, and locations mentioned in this narrative are entirely fictional. Any resemblance to actual individuals is purely coincidental. This story is a product of the author’s imagination. The author does not endorse any products or entities mentioned herein.
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All copyrights to this story remain strictly that of the author. No other publication, use, or reproduction of this story or parts of this story is allowed without the author’s written consent. It is published on www.gaydemon.com. Under the pseudonym of StrykerJ.
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A gay summer Holiday – Chapter 20

• Twice you go Black... But they got your back.

It was late on Saturday when Chris grabbed his gear and dragged his weary hide off the gangway and onto the mainland dock. He was exhausted, but a smile broke across his face when he spotted a familiar trio: his father, the ferry service CEO, Douwe Todd, and the Islander tourist board manager, all chatting merrily.

A fourth man stood with them — a stranger who radiated an ‘official’ aura. They ushered Chris toward the waiting room café, a place usually bustling with travelers but now occupied only by a few lingering truck drivers and crew members draining their last coffees before heading to a hotel.

At first, Chris’s father had a hard time recognizing the muscular young man in the pointy boots and sleek crew threads. Over the summer, the twunk had bulked up significantly, his pale skin bronzed by the sun and salt. Even the new, short, spiky bleached hairstyle had thrown John-Peter off. It was actually the guy from the tourist board who gave the rockstar a shout-out; Chris knew the face, though they’d never shared more than a nod.

Hêh, Christopher! Over here, soan!
John-Peter did a comical double-take, only truly recognizing his boy when Chris called back, “Good’n, Sir!” Chris hopped off the gangway, cutting through the locked dock gates to the ticket office. “Hi! Quite the reception committee!” he remarked, taking in the four older men awaiting his arrival.

John-Peter draped a heavy arm over his youngest and guided the bewildered boy inside. He gave the hunk a fierce fatherly hug and a scratchy, whiskered kiss. Chris wasn’t usually a fan of bearded men. Still, he drank in the uncommon warmth his old man was finally showing his youngest offshoot. Even the ferry CEO gave his relief crew member a warm ‘bro-hug’ as he snatched Chris’s weekend bag from his hand. And the tourist board manager clapped a familiar hand on his shoulder.

Douwe introduced him as Martin Smidt, before John-Peter stepped in to introduce the fourth man: Big-Mc, his new lawyer, the formidable-looking Barnibald McKinzie. The man loosened his thin leather necktie and undid the top buttons of his starched pink dress shirt with a deliberate, practiced ease.

He took off his office glasses and shook loose his thick, wavy mane of jet-black, sophisticated African twists. Christopher imagined him sporting a tight top-knot in court and letting it hang wild and loose by night. Quite attractive. As McKinzie flicked the tangled bush over his shoulder, Chris had to clap a hand over his mouth as he spotted them: seven very familiar colored pride beads dangling from a thin gold chain on Barny’s right ear.

Barny was a broad-chested, dark-skinned, handsome man with a deep, sexy voice and an intensity in his gaze that made Chris wonder exactly what ‘Big-Mc’ stood for outside of the courtroom.
But you, Christopher, can call me Barny,” he said, his grip firm and lingering just a second too long to be strictly professional. “I’ve heard so much already — we spoke over the phone! I’d love to represent you… and your father. The partners at McKinzie, Stern & Moore are already sharpening their teeth.

Stern and Moore? S&M? Fuck, he’s Sergeant Tomas and Master Cody from Amsterdam rolled into one,” Christopher thought in delight, suppressing a grin.
Snap out of it, Chris!” he chided himself as he caught his eyes wandering. Between the name of the firm and the way Barny’s thumb softly brushed over his knuckles, the ‘twunk’ realized he wasn’t just dealing with a legal eagle; he was dealing with a predator who likely enjoyed a very different kind of ‘heavy hitting’ once the sun went down.

Good to have you on the team, Master Barny,” Chris replied, dropping the title with a pointed look. “Because some Islanders are looking to do some serious damage to my reputation just for turning gay.

As they found a warm spot inside to talk business, Chris laid it all out — the weeks on the Island, the new house, his boyfriend, and the trouble he’d found for simply being himself. Douwe, after setting down a fresh pot of coffee, slid a contract in front of his star volunteer. He was formalizing their arrangement, and Martin Smidt followed suit. The tourist office was putting Chris on call as a cultural asset; he sang, he danced, and he spoke eight or nine obscure languages. After a quick nod from his lawyer, Chris signed on the spot.

Before they left, Barnibald — Big-Mc — handed Chris two business cards. One was for the firm; the other featured a Tom of Finland-style depiction of Barny in a biker jacket, holding a padlock on a heavy chain. It had his private details.
Chris thanked him, stroking the thirty-something brute’s back. Big-Mc gave him a half-concealed wink and pushed his tongue three times against his glistening cheek — a move that left Chris to let out a low, shuddering whistling sigh. It earned him a clap on the shoulder that nearly buckled his knees.

We got this, kiddo. You just do your thing. I’ve got your back,” the lawyer said. Or was it Master Big-Mc? Chris didn’t know yet, but he was dying to find out. As they watched the lawyer saunter away, Chris couldn’t keep his eyes off the man’s tight buttocks, which filled out those shiny, mottled-gray office slacks perfectly.

Did you tell him I’m gay, Dad?” Chris asked softly, his gaze still lingering on the man.
No? Why? Should I have?” John-Peter asked, genuinely confused.
Nah… but I think he’s part of the ‘team,’” Chris smirked.
Whatever gave you that impression?” his father inquired sharply.
The things he said, the way he carried himself, and… umm… this!” Chris held up the private business card, the Tom of Finland black biker glinting in the streetlight. John-Peter’s eyes lit up.

Just then, Barny’s luxury Lexus purred past them. The lawyer stuck a hand out the window in a sharp wave to his new clients. In response, Chris didn’t just wave back; he reached down, grabbed his bulge, and adjusted his package with deliberate bravado.
John-Peter caught the gesture and let out a dry chuckle. “Ha… well, if it bothers you that much, we can always find you some stuck-up Dutch law school dropout.
HELL NO,” Chris grinned, feeling the adrenaline of the evening finally start to settle. “I think ‘Big-Mc’ is exactly what I need.

The two of them turned away from the docks, walking across town toward his father’s new place. For the first time in years, the silence between them didn’t feel empty; it felt like the quiet before a very successful week ashore.

• Dear Diary: Sunday the 13th – I think. Dad’s new place.
Things are klunking into place. Talked for ages with Dad over a new bottle of whiskey. It was empty by the time we covered the basics. I never had so much fun with my old man. His new place is much smaller, but he set up two guest rooms for Leeroy and me.
I thanked him for the large sum of money, of course. He smirked and told me it was for all the birthdays and holidays he missed. Though I am almost sure he took most away from the High-C trustfunds. We’re going car shopping on Monday — he showed me the auction site. All government surplus equipment. My eyes nearly rolled out of my sockets when I spotted the truck of my dreams — a too ridiculous for words six-by-six beast! And I almost swallowed my tongue when an eight-ton excavator popped up. Trailer and all.
But as I lie here, I cannot keep my mind off Master Barnibald McKinzie. Fuck, he’s hot. And if his private business card is anything to go by, he’s into the same stuff I am.

Hold on — got an App notification. IT’S HIM! Holy bondage crap, Batman. Let me lube up and sneak out. Master is hard and waiting. He added me to his personal OnlyFans account! Well, that makes sleeping a long shot. I think I am going to paint the ceiling tonight!
Sorry, Wyatt. Wish you were here to see this. He’s brutal AND huge!
*Gna gna, giggedy giggedy.*

Early on Sunday morning, Chris’s father had shown him a brand-new shipping container packed with his old life and bits and bobs from his own. The first thing Christopher saw was the broken Marrakesh guitar Chris hadn’t seen in twelve years. He couldn’t believe his father had kept that thing from the rest of the family — even after Caesar put his foot through it.

Despite the bashed soundboard and the detached neck, the guitar was in much better shape than Christopher remembered. He had missed that beauty. A left-handed Martin D-18 Deluxe, made like no other. Though seeing nineteen years of painful memories packed into one steel moving box was a bit much.

The lawyer he met yesterday had sent Chris a rather cryptic text. Barney had asked Chris to drop by to see if he ‘fit’ the law firm’s profile and to sign ‘the contract.’ Christopher had smirked at the contents of that text since the moment he received it. He hadn’t answered like a ‘good little boi.’ He knew exactly what this was about. It takes one, to know one.

It was half past one when Chris told John-Peter he had to ‘clear his mind for a bit’ and explained not to expect him for dinner. John-Peter handed the boy a spare house key and told him to let himself in, warning the boy not to make it too late. They had an auction to get to the next day.

His polished pointy cowboy boots, wrist wallet, and leather muscle vest carried the bronzed twunk toward the train station. His loose, light-blue jeans and white V-neck shirt contrasted nicely with the black leather. It was warm — too warm for a Dutch mid-June — and thunderstorms at night were the norm rather than the exception.
It was a good thirty minutes by train to the provincial capital. As early as he had left that afternoon, Chris arrived at Big-Mc’s crib at 2:28 PM. It was nothing special, located on the rougher side of town — not somewhere you’d expect to find a high-end law firm.

Christopher had texted Big-Mc’s private number when the train rolled into the capital’s main station. He felt giddy like a schoolboy on a first date and a little apprehensive.
As he strolled into the unkempt street lined with dilapidated three- and four-bedroom houses, he spotted the black Lexus. It was parked next to a pimped-out pickup truck and two muscle bikes. And there was Barnibald McKinzie, standing in the doorframe.

Woof!” Chris grinned to himself as he spotted the Dutch African hunk. Barney wore a black wife-beater, gold bling, and leather pants over white sneakers. It was a completely uncharacteristic look for a lawyer — more like a thug with spending money.
Shit, I should gamble more often! I was right about this dude. Queer and kinky as a nasty motherfucker. Best play it cool.

As the boy stepped up to the unyielding black man, his eyes flickered over the outfit. What Chris had thought were leather jeans were, in fact, leather chaps. A black jockstrap, with a thin, handmade leather front, was already stretched to the breaking point. Chris reached out, grabbed the heavy tool by the head, and shook it playfully.

Hêh,” Chris said, letting his Islander dialect slip out.
Wassup, Thug. Nice handshake, bitch. Are you always this forward, or just nervous?
Barney guided him into what looked like a literal crack den. In the shabby living room, Chris was introduced to Stern and Moore — and to a fourth dude his own age: Victor Moore. As their eyes met, Chris instantly knew this was the one to avoid. Victor was the prototype jailbird thug — bare-chested, covered in tattoos, and wearing Adidas leather tracksuit bottoms. His fake grin revealed a gold grill that matched the heavy chains hugging his neck.

What the fuck are ya looking at? Get out of my crib, cracker!
Hold your horses, BITCH! Big-Mc wanted to see me — I’m just doing as I’m told. And get those biker boots off the table!” Chris growled as if he owned the goddamn place.
As Victor jumped up, Chris heard a familiar metal flick. Something he had heard often enough back at his old technical school. Back then, those young guys were trying to posture as if to defend their spot in the pecking order. The thug was threatening Christopher with a cold, unpolished steel blade.
Get to your fuck’n knees and get it over with! Eat a Big Mac, white slut.

The ebony thug twisted the boy around and forced him to face Barnibald McKinzie. The man was already stroking fourteen inches of black, veiny, glistening schlong. Chris had seen something that impressive once before on the Island. Come to think of it, both Big-Mc and the Island’s only black cop looked remarkably similar.

Chris didn’t flinch; he didn’t buckle. Back in technical high school, any self-respecting man had dealt with this kind of over-the-top behavior. Well, not the exposed, heavy ebony meat sandwich, but the cold steel. Boys will be boys. Christopher just grabbed the hand holding the knife, pressed his thumb deep into the flesh, and twisted. Hard. The blade landed point-down between his lawyer’s sneakers. Christopher snatched up the quivering tool and flicked it closed. Pocketing it.
Barney drove his fist into the twenty-three-year-old thug’s face and smirked as he watched him topple to the ground.

Go on, soan. Take a close-up look. That’s what you came for, ain’t it? Tommy tells me you take these oversized black tools well.
Well, now!” Chris said in surprise. “Is Tomas your older brother? Had him, done that. Done that cop well.

Chris was on his knees before you could say, “Holy fuck, Batman.” He swallowed the fourteen-inch tool deep. Barney wasn’t fully stiff yet, but even semi-soft, it was an impressive sight. As the total size-queen Christopher had turned out to be, he took the man shockingly deep.

Yeah, take that monster… Eat that shit… Swallow that Big Mac whole!… Stuff his throat, make him choke on it, Barney!” Victor Moore shouted. He had scrambled up off the floor and grabbed a fistful of hair, trying to force Chris deeper over the tool. Christopher looked up at Barney and rolled his eyes in anger. He liked worshiping big tools, but he didn’t need the assistance of this asshole. Victor’s own father, Derick Moore, was sitting submissively on his knees, watching the effort up close.

Vic, cut it out, man! Go to your room if you can’t play nice! Can’t you see he’s doing it? He’s not one to piss off or abuse!” Victor’s father growled in a surprisingly high-pitched tone.
Yeah, not every white boy needs help worshiping black dick!” shouted the Caucasian Stern, the other associate and a leather biker master. Chris liked the look of Master S. Well, no — but he was dressed like a stern biker. Dressed in full leather, whips, paddles, the works. His white, hairy daddy-dick poked out of padded biker pants.

Christopher didn’t care what happened around him. He was focused on the slowly stiffening monster. The beast had come to life in his throat, and it became increasingly harder to take him deep. So the nineteen-year-old changed tack. He started to worship the full, veiny length of the shaft, swiping his tongue up and down — worshipping the black schlong from smelly nuts to dripping head. This one was darker than its counterpart on the Island, but it tasted just as sweet.

The horny boy looked up as he took the black head between his lips and let his tongue do the talking. He knew he was on the right path when he felt the heavy frame of Big-Mc sway, and his knees buckle.
Chris pulled off, pushed his lawyer onto the dirty leather couch, and dropped his jeans. He crouched over the throbbing tool and let out a howl.

Fourteen inches! He made fourteen hard inches fit. It wasn’t easy, and it wasn’t quick, but it went all the way inside. Stern and Moore looked on with wide eyes at the ‘bitch’ riding this black Master — hard and deep, in long, deliberate strokes. It was as if Chris were the whore they had always wanted to represent.
How’s that for a fit?” Chris asked sneakily as he leaned forward to kiss Barney.
That’s your contract signed,” Barney sighed. “Fuck, Tomas was right. You do like ’em big.

Yeah. He’s quite the nigg’r-lover,” called Victor Moore, disgruntled, from the other side of the room. It broke the spell. Even his demure old man and Master Stern looked shocked. They knew the gangbanger and all about his past misdeeds. He had plunked himself into a leather armchair and was wanking his six-inch ‘chocolate Twix bar’ with vigor. Barney was three times his size — in muscles, length, girth, and attitude.

Can I?” Chris asked quietly, looking angrily over his shoulder.
Go for it! Adjust his attitude. Ruin his black cunt,” Barnibald McKinzie whispered in Chris’s ear. “Rape that little shit!
Chris was on the young Dutch Ebony thug like horseflies on a dungheap. He snatched the dude’s knife from his back pocket and ran it over the stitches of Victor’s tight black jeans so fast the rest didn’t even know what happened. The seam split, and Chris lunged forward. Eight-and-a-half white inches stretched the puckered ebony cunt wide open.

By the time his dick found the second hole, Victor had pointed a girly handgun at Christopher’s forehead. He wielded a .25-caliber ‘Saturday Night Special’, the tiny weapon swallowed by his thuggish hand as if he’d mugged an old lady for it. Chris grabbed the gun and twisted it with a sickening crunch; he forced the barrel upward, thumbed the takedown latch, and shucked the slide right off the frame. Metal bits clattered to the floor in an instant.

He rammed back inside in a blind fury, plowing the shocked thug’s hole hard and fast. Chris didn’t stop until he fertilized the crap out of the young ebony man.
This was not what the twunk had expected. Chris had more or less hoped for a lesson in domination — or, looking at Master Stern, a bit of bondage. Heck, he would’ve gone along with some actual BDSM group sex. But these leather-clad lawyers had skills no law school ever taught.

Big-Mc handed the reassembled gun to Chris as he pulled him off Victor. The thug lay there gasping, sporting a dirty smirk; he had never been manhandled like this, especially not by a five-foot-seven Islander kid. He’d toyed around with plenty of white boys, but none could top this muscle stud. To say even Victor Moore was impressed was the understatement of the year. He wanted more.

Barnibald took Chris upstairs to the guest room and showed the boy a good time. It was hard work but great fun. Even Master Stern tag-teamed Big-Mc and did his thing, spanking the crap out of the Islander dude before asking sweetly for permission to screw his brains out. The leather sex with the white biker man was amazing, and Chris got to experience the submissive side of the older Moore, too.

When Victor finally dragged his sorry ass upstairs, he simply handed the boy a leather hoodie. “It’s raining outside. Can I drop you off at the train station, Mr. da Boer?
Chris smiled. “Call me Christopher, Vicky. You can be my bitch — I won’t tell your posse.” Victor tilted his head like a puppy and grinned. “I’d like that.

Cool hoodie, man. Did you make this yourself?” Chris smirked, his hand stroking the buff garment.
I run a leather tailoring shop behind the station. It’s a bit off the beaten path, but we do good business.
In that case… can I commission you for a rush job? I’ve got a friend’s birthday coming up. He wants a distressed tobacco-colored A-2 bomber — something with a heavy patina and a sharp shirt collar. Small kid with short arms, nice big cock, though — we couldn’t find anything in his size. But he prefers the dark brown leather to the black one. That’s more my thing,” Chris explained.

Fuck yeah. I’ve noticed. Thanks for the poke, by the way. And sorry about earlier. I enjoyed the sex with you, da Boer.
Why don’t you show me the shop? I can take a later train. I can pay you upfront with a good blowie.
Fuck, you drive a hard bargain. Deal, bitch.
Victor Moore said it with love this time, not the snarl he’d used earlier. Chris had broken the thug’s hard shell, penetrated it, and planted the seeds of something new.

Christopher hopped onto the back of the heavy bike and hung on for dear life. Well, no — not really — but he liked the feel of the tough brown biker jacket the butch man wore. The ripped seam of Victor’s tight jeans exposed just enough ebony crack to make the short ride enjoyable for both. At the shop, Chris picked out Peter’s birthday present and gave Victor Moore the back of his throat. Moore was rough and ruthless, but the muscle twunk didn’t mind; this time, he got the better end of the stick.

Chris handed the gun to the butch gangbanger. Victor took the .25-caliber back, but told the Islander to keep the knife and the leather hoodie as mementos of their encounter. Before Chris left, Victor gave him a surprisingly soft, long-lasting French kiss, worshipping his muscular frame.
Christopher barely made it to the train in time, but the grin on his face couldn’t have been wider. He liked these men. Rough and ready. And now, they had his back.

The next morning, Chris and John-Peter drove a rented Toyota Pickup from the ferry port to the auction location in the middle of the country. It was packed, and John-Peter warned Christopher not to get his hopes up and stick to his budget.
They walked the rows and rows of equipment, attachments, and vehicles, but Chris was hell-bent on the stuff he found online.

The only trouble was that the truck arrived in vibrant sunset yellow, with mismatched parts. The fluorescent red under-band on the lower sides of the six-by-six F-550 heavy-duty matched the bright red brake shoes, but that was where the coordination ended. The reinforced tilt bed was finished in a matte gunship gray. The former DOT truck was accented with metallic blue chevrons that pointed aft on the sides of the bonnet and the front doors. It really was a utility truck like no other — a powerful mix of government surplus and high-end engineering. Big enough to impress, but not so big that it could not handle the Island’s narrow backroads and wider bike paths.

Beyond the odd paint job, the specs were enough to make Chris’s mouth go dry. It sat high on a specialized hydraulic lift kit, its frame supported by six massive, military-grade run-flat tires that looked capable of crushing a mountain. Front- and rear-heavy-duty winches were tucked into custom steel bumpers, and a row of high-intensity LED searchlights crowned the extended cab. It wasn’t just a truck; it was a mobile fortress designed to survive an apocalypse — or at least a very long winter on a remote island. Well, at least the snowplow mount and side-mounted engine breather suggested as much. Wyatt’s ‘little’ Volkswagen Amarok Aventura was nothing compared to this beast.

Nothing that a little paint job in midnight black can’t fix,” grinned Chris to himself as the monster rolled onto the auction floor. He outbid the competition and could call himself the proud owner of a truck that could go places, and do things.
That, and it could tow the one thing he really needed. A mid-range eight-ton excavator with an extended reach boom. Extended everything, really. Even the padded metal treads could widen its stance for extra stability.

Chris got it cheap. No one but he, seemed to have a purpose for it. The trailer and the odd assortment of buckets and implements were another matter. But the money he had ‘saved’ on the excavator came in handy now. Chris bought three trailers to bring back to the Island; it was a different matter how to get them there. But with the help of some friends, he could solve that puzzle, too.

• Continued in part 21 •


Thank you for reading this story.
Please give it a 👍 Like or a Comment if you are inclined to do so.
And if your hands are not too dirty from all the spilled cum! 😋

©  StrykerJ - May 2026

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