Gay Summer Holiday

The warm family welcome was a nice change from the nasty comments his siblings gave Chris at home. The holiday had started off warm. But the heat Jelmer and Jessie gave him late that day and into the following morning was even hotter. Turned out all three men arrived at the same conclusion. They were gay. The Island is begging to be explored.

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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 2

• The family get together.

There they were — his Island family. A sea of familiar faces happily waved as Christopher descended the ferry’s passenger ramp. It looked like his grandmother had brought out half the aunts and uncles still living on the wooded dunes. Chris called them ‘Aunt’ and ‘Uncle’ out of habit, though the bloodlines were a tangled web stretching back to his great-great-grandparents. Heck, on the Island, everyone was kin if you went back far enough.

Being here felt like a victory. For the first time, Chris was his own man, miles away from the shadow of his brothers and sister. The yellow sandstone lighthouse towered over the quaint, touristy town — a sight for sore eyes that lifted his spirits instantly. Beyond the tower, the dunes rolled out toward the horizon, promising adventure at the ‘Harbor View Campgrounds’ run by Great Uncle Ben and Aunt Frida.

Chris breathed in the salt air. He was home. Home where the seagulls shrieked their salt-streaked songs, where the trees rustled in the stiff breeze, and the North Sea leapt playfully against the quay wall. The working holiday had started out great. The butterflies in his stomach made Chris walk on air, his mind drifting back to the toilet stall on the ferry. He hoped the encounter with the burly man wasn’t the last time he got lucky during this extended summer holiday.

Grunting, Christopher hauled his bulging bags and suitcase down the ramp, winding through the metal fencing toward the ticket hall. He muttered a silent prayer of thanks that he’d sent his heavy tool chest ahead via a freight courier; even without it, he was carrying his entire life in his hands, and the straps were digging into his shoulders.

He walked through the ticket hall, and his aunt Dianna greeted him with a broad smile.
Take off that childish hat, Chris!” she teased. “I cannot believe Mathias made you wear that thing!” Chris laughed, reaching up to adjust the brim. He told her it was the only thing keeping his hair dry in the gale.
He quickly moved on to the business of the return ticket, explaining how he’d been ‘shanghaied’ before he could buy one on the mainland. Dianna handed over a return ticket, her laughter echoing through the hall at his retelling of the morning’s chaos. “You know — you could always come work here,” she suggested. “We’re going to be short-staffed for a few months.

I’d love to, Aunt Dianna, but I already promised to help fix up the bunkers at Harbor View,” Chris replied. He paused, his mind still sharp from the adrenaline of the crossing. “But why doesn’t the company just get some interns from the local nautical school? Or even ask the hotel staff to man the bars on the ferry before the peak season starts?
Dianna’s eyebrows shot up in surprise. “Hey, those are some excellent ideas! Thanks, Chris. It’s silly that head office didn’t think of that themselves!” she replied, clearly impressed by his initiative.

Oh, yeah — and then there’s this,” Chris added, his voice turning a bit more serious as he gestured to the heavy leather biker jacket. He felt a pang of reluctance but knew he had to play it straight. “I was hoping I could borrow this for a while. You know... until the rightful owner contacts the lost-and-found department. I found it tucked under bench 46-port in Saloon 3, amongst the discarded detritus.

Dianna took the jacket, feeling the weight of the thick cowhide. She pulled out a small logbook and scribbled a quick note.
Ah... let me get the details down. Honestly, Chris, I don’t think they’ll want it back. It’s rare for people to call us about lost clothes once they’ve left the Island. It suits you, though. It makes you look like a real man.
She handed it back to him with a wink.
Take good care of it. If nobody claims it by the end of the month, it’s officially yours. You may want to have it drycleaned. It reeks!” she grinned.

Christopher stepped out of the ticket office and into the arms of a massive reception committee. He had swapped his white crew bomber for the heavy biker leather, feeling emboldened by the look and walking tall. His grandmother stood front and center, flanked by Great Uncle Ben and Aunt Frida.

It seemed word of his extended stay had drawn out half the town — including the local police. Amid the sea of hugs and warm welcomes, his best friend Jelmer appeared. He had a bit of a weird look on his face when he saw Chris, though. He brushed it off as nothing and gave his bro a chest bump and a hug. God, he had missed him. Jelmer took his gear and drove it to the campground in his blue 1960s Army Jeep. Christopher didn’t see the twenty-year-old man after that. This was weirder still. What was going on?

After a quick stop at his grandmother’s place to borrow Uncle Burt’s bike — on the condition he’d ‘return it with a full tank of fuel’ — Chris joined the family for a celebratory feast. They had heard about the disastrous birthday party, and Aunt Petra had invited Chris and their friends to her B&B for a do-over.

The air was thick with laughter and the rich scent of a meal her husband, George, had prepared. Uncle George was the chef cook at a local hotel a few miles up the island on the North Sea coast. This was the kind of unconditional love Christopher had been missing at home. These were his people, and they accepted him as one of their own — not just another tourist or an outsider.

• Dear Diary: April 30th — 9:35 PM.
WOW, I wish my birthday last Friday was as fun as this one. What a difference a little love and understanding makes. But where is Jelmer? I have not seen him since I arrived. Oh well, time enough to catch up. The salt air made me hungry; Petra and George took care of that, though. Time to get settled in. Ben said he had Jelmer and Jessie clean one of the larger bunkers as my home-away-from-home for the next four months. This should be fun. But I can do with a good night’s rest. It was a tough day. I wonder what the rest of the holiday will bring...

The Island had played a pivotal role in air defense during the Second World War. A lot of bunkers still remained, mostly hidden under the sand dunes by now. The officer’s lodgings overlooked the rooftops of the main village. Still, eighty years of North Sea weather had taken a toll on the concrete and brick structures. They had been converted into holiday lets, but they were in desperate need of some TLC.

That’s where Chris came in; he was up for the challenge. After a long and pleasant evening with his extended family, Great-Uncle Ben took Chris to the campground. He showed Chris the extent of the work that needed to be done and gave him a master key to the bunkers. The concrete lodgings had been dug into the side of a dune, featuring thin partition walls, a brick kitchen extension, rotted doors, and patio windows. The roofs leaked, the floors needed a new layer of concrete, and the walls were in dire need of a lick of paint. Christopher had his work cut out for him.

No, the structures weren’t much. You couldn’t even call this ‘glamping.’ But that was the charm of these old buildings. The bedrooms didn’t even have a wall or doors separating them from the living room — let alone windows out the back. The only privacy came from old-fashioned curtains suspended on a rod halfway up the bunker. Heck, the former bunkers didn’t even have air conditioning, though the thick layer of sand and dune grasses on the roof provided a bit of shade against the summer heat.

The yellow-sandstone lighthouse sliced through the dark, its rhythmic beam brushing the night sky. Chris climbed the steep dune path toward the two largest structures, which sat overlooking the thirty smaller bunkers huddled in a long row behind the town. The stiff breeze from this afternoon had settled, whipping the tall dune grasses into a frenzy.

As he reached the summit, a sudden prickle of heat crawled up his neck. There, bathed in the flickering glow of the lighthouse’s beams, sat Jelmer’s old blue Army Jeep. It was parked right outside the bunker entrance, its engine silent, looking like a ghost from the island’s wartime past. Christopher felt a shiver that had nothing to do with the cold. Jelmer was in there — and he was waiting for Chris.

The two men smiled at each other as the nineteen-year-old walked into the four-roomed commander’s bunker. Jelmer handed Chris a beer from the fridge. There was that look again. What was going on?
Chris gratefully took a sip of the cold brew and sat on the queen-sized bed. The springs creaked as his weight settled onto the edge. Jelmer settled himself in one of the leather lounge chairs opposite.

God, it’s good being back here,” sighed Chris. “How’s it hanging, Jel? —” He had to stop as he saw the expression on Jelmer’s face. “What’s the matter, cuz?” asked Chris after a while.
I... I can’t... Damn, you look great in that leather jacket,” Jelmer exclaimed. “And since the last time I saw you, your muscles have nearly doubled in size... I’m a bit jealous. Well, a lot, actually!
Ha, thanks, man... now will you tell me what’s really going on? Come on, you can tell me!” Chris asked insistently.

Jelmer said nothing. Instead, he opened up one more beer and drank it way too quickly. The result was a mess of foam spewing out over the floor. “Aww... don’t blow your load just yet,” joked Chris. “Exactly,” said Jelmer. Christopher didn’t understand what Jelmer meant.
Chris... I got to tell you something,” he started, looking sad and anxious at the floor. “No use crying over spilled beer, bro... Just tell me already. I promise not to laugh, and I’ll keep it to myself if that’s what you want,” said Chris, sensing that Jelmer had a heavy secret he needed to share.
Okay then... here goes... but promise you won’t tell a living soul!” said Jelmer.

At that exact moment, Jessie walked in. He was two years younger than his twenty-year-old half-brother, Jelmer. Jessie lived at the campgrounds with their grandparents, Ben and Frida, but Jelmer had his own place. But Chris had practically grown up with these two.
Hey, cuz... grab yourself a beer!” Christopher said to Jelmer’s younger brother.

Have you told him yet?” Jessie asked, looking at Jelmer. Chris looked between his two favorite friends, his confusion mounting.
Okay, now the suspense is really killing me... is someone going to tell me what the frick is going on here, boys!” Chris shouted. “Or do I need to give you two blowjobs again to torture the truth out of you?!

The boys laughed naughtily, the tension breaking for a brief moment.
Chris, you don’t know the half of it!” Jelmer laughed out loud. “Okay... here goes... I wanted to tell you by myself, but I guess Jessie should hear this too —
After a short pause, Jelmer’s words tumbled out in a rush: “I think I’m gay, and I’m in love with you, Chris!
Jelmer immediately averted his eyes, staring at the floor and bracing for the worst.

Aww, that’s cool,” Chris said after a long, quiet moment. “Good for you. I’d love to help you discover those feelings, bro! And hell, I need to tell you what happened to me on the ferry today. You won’t believe it!” Chris was beaming. Jelmer looked up, stunned by the positive reaction. He had half-expected a fight; he didn’t expect an invitation to explore.

Jessie looked at Jelmer, pride beaming on his face, and gave him a big, freeing hug. “I knew it, bro! And you may join the club,” he said, winking at his older brother. The revelation knocked the wind out of Jelmer.

Christopher laughed, the sound echoing off the bunker walls. “Okay... shall I make that a threesome then? I had a really ‘nice’ experience on the ferry today. I got sucked off by a leather man, and I found this jacket during the cleanup. It makes me feel pretty gay, too,” Chris said proudly.
Okay, that’s not funny! Here I am spilling my guts, and you two are making fun of me,” Jelmer shouted, his face reddening with anger.

Hold your horses, cuz,” Chris said, punching Jelmer playfully in the gut. Chris unbuckled his pants, letting them drop just enough to show the boys his cock-strapped dick. “I got this from a leather man after he anonymously deep-throated me on the ferry today. And as far as Jessie goes... I’ve known he’s been having gay feelings for a couple of years now. Nothing wrong with that! Hell... we’ve all sucked each other off — more than once, even — and we enjoyed it. Didn’t we? So stop being a sissy and accept the facts! I’m really pleased for you, Jel. And I could see myself falling in love with a stud like you, too,” Chris said, his voice dropping into a low, husky growl as he rubbed his hands through Jelmer’s hair.

Christopher stepped closer to Jelmer, pulling his length free and hitting him teasingly across the face with his nearly nine-inch half-hard slab of meat.
Take it, boy... Suck the juice out of it!” Chris exclaimed. He knew it was a bold move, but somehow the earlier experiences and the fucking cool biker jacket made him do it.

Jelmer, however, wasn’t up for it just yet. He started to tremble, his eyes turning moist. Realizing he’d pushed too hard, Christopher stepped back and tucked his cock halfway back into his pants.
Aww, man... I’m sorry... come here, bro,” Chris said to his admirer. He sat down between Jessie and Jelmer on the bed, pulling Jelmer into a loving hug.
Jel, I’m proud of you, man... I truly am! To me, it doesn’t matter what you are — as long as we can be friends, bro,” Chris said with a heavy, relieved sigh.

The bunker was quiet for a moment, the only sound the distant whistle of the wind over the dunes. Chris sat between them, his large frame anchored on the edge of the queen-sized bed. He could feel the heat radiating from both brothers. Reaching out, he rested a heavy hand on each of their knees, grounding the moment.

Hey, Jelmer, look at me,” Jessie said softly, waiting until Jelmer finally met his eyes. “No more heavy stuff for tonight, okay? We’re all friends, and apparently, we’re all a little bit ‘nasty’ too.” He gave them both a conspiratorial wink.

Why don’t we grab a beer and just relax?” Chris suggested, his voice low and steady. “Jessie, grab us another round from the fridge, and Jel — why don’t you see what you think of this leather? You said I looked like a badass — feel how thick this cowhide is.

It was the perfect icebreaker. Jessie hopped up to grab the beers, his youthful energy lightening the mood, while Jelmer tentatively reached out. His fingers brushed against the sleeve of the jacket, the material cool and rugged under his touch. Chris didn’t wait for an invitation; he draped a heavy arm over Jelmer’s neck and pulled him in for a deep, hungry kiss. The kiss turned quickly into something more. Tongues started to wrestle, and hands began to grope blindly over denim and leather. Buttons flicked open, and the air in the concrete room became heavy with the sound of low moaning.

It’s... it’s really heavy,” Jelmer murmured against Chris’s lips, his voice steadier now but breathless. He moved his hand up to Chris’s shoulder, feeling the solid mass of muscle underneath the hide. “You weren’t kidding about the gym, Chris. You’re like a rock.

Heck, tell me about it,” Jessie chimed in, coming back with three cold bottles. He sat back down on Chris’s other side, bolder than his brother. He reached out and squeezed Chris’s bulging bicep, his thumb tracing the seam of the leather. “Damn, cuz. You really look dangerously good in that jacket. Why don’t we give your dick a proper welcome-home massage?

Chris smiled, feeling the plan come together. ‘Jessie knows exactly what he’s doing,’ he thought.
Now that sounds like a plan,” Chris replied, his voice dropping an octave as he began to shrug off his pants. He saw Jelmer immediately follow suit, his movements eager. “But I warn you boys... once I start relaxing, I might not want to stop. God, I’m so fucking horny. I think it’s the leather.

Christopher looked over at Jessie, his eyes raking down to the younger man’s bulging jeans. With his free hand, he pulled his other ‘cousin’ closer and gave him a brutal, lingering smooch. Sure, these guys had all done this before, but the taboo felt sharper tonight. Technically, as second cousins, Jelmer and Jessie shared less DNA with Chris than the alcohol percentage of the beers they were currently chugging.

And seeing as the two of them were half-brothers, they didn’t seem to have much of an issue with the overlap either. In the cramped, humid air of the bunker, biology was taking a backseat to a much more urgent kind of chemistry.

Before long, Chris had Jessie’s rod twitching between his lips, giving Jelmer a front-row seat to the technique he’d picked up. He could feel Jelmer’s hand, tentative at first but growing bolder, stroking his eight-and-a-half-inch cock to life.

This — exactly this — made the room start to heave. Like the rolling swells of the North Sea from earlier that afternoon, the concrete walls seemed to sway. The bedsprings groaned under the shifting weight as the three mostly naked men repositioned themselves.

Chris was down between Jelmer’s knees, his mouth a blur of heat as he licked and spit on the swollen length of his childhood friend. Behind him, Jessie was working his tongue like a pro, rimming Chris with a hunger that made his head swim. Christopher had never had anyone ‘down there’ before; it felt heavenly — a dark, filthy kind of pleasure that hummed through his nerves.

When Jessie reached up and gripped the heavy leather belt of the biker jacket, yanking Chris backward to sink his tongue even deeper into that puckered hole, the experience hit a whole new level of intensity. It was a damn tragedy they hadn’t started doing this years ago.

Chris’s cock felt like a bar of iron, slick and throbbing as Jessie edged him with a brutal, fast rhythm. The air in the bunker was thick with the scent of sweat and cowhide.
Don’t just look at it, Chris,” Jessie hissed, his voice raw and commanding. “Stretch him out. I want to see you violate that hole. Breed him, take him, make him yours — it’s what he’s been begging for!

Christopher wasn’t exactly against the suggestions, but the visceral edge in Jessie’s voice sent a jolt of nervous heat through him. He spit into his palm and slicked Jelmer’s tight, puckered hole with a thick finger, pumping it in and out to prime the engine. At the same time, he went back to work on that massive eight-inch shaft. It wasn’t quite as long as Chris’s own, but the girth was insane — a heavy, meaty club that felt like it needed both hands just to manage it. Well, one finger turned into two, then three.

Jes, give Jelmer something to bite on,” Chris joked, “I’m going in!” Christopher straightened up and looked over his shoulder, winking at Jessie. The eighteen-year-old got up to leave the two guys to experiment on their own.
Where the fuck do you think you’re going, Jessie? You’re up next — guys — let’s see where this takes us. I’m willing to try anything if you guys are?” Chris panted hornily.
Have fun, guys. I’ll have to take a rain check, Chris. I have to get up early tomorrow. You guys got this. Damn, you two look made for each other.

Chris snapped his fingers at Jessie and pointed to the two swaying dicks. Jessie dropped between the men and sucked off Chris, taking the nearly nine-inch dick down his throat just like the leather man on the ferry had done. Then he repeated the party trick on his half-brother. Jelmer screamed as Jessie engulfed the tool deeper than any girl ever had.

Goddamn — Do not pass Go — Do not collect two hundred dollars — Go directly down your throat — Fuck — this is — oh God! — How fucking nice,” Jelmer exclaimed as he shot a thick load of cum into Jessie’s esophagus. Jessie looked up at his brother’s massive orgasm.

Chris couldn’t let Jessie go home empty-handed, so he sucked the boy rough and ready — fast and deep. He gave the young man no reason to hold back, and Chris, too, got a mouthful of spunk.

It took the three of them a while to come down from the intense adrenaline rush. They lay side by side on the cramped bed, Chris in the middle, still wearing his leather biker jacket. He lay arm in arm with them, smacking his jizz-splattered lips while Jelmer and Jessie breathed heavy on either side. Jelmer couldn’t believe his eyes; his hero was actually going to deflower him, good and proper. He knew it.

Jessie downed the last of his beer and wished the guys a good night, slinking into the dusk. Chris watched him go, realizing with a pang that the lighthouse keepers could have seen everything. They hadn’t bothered closing the curtains, and their powerful binoculars, he knew, had night-vision.

As he looked over at his best friend, he knew what had to be done next.
Oh God… Chris — fuck me, please… fuck me now!” Jelmer shouted. Chris got up, walked over to the windows, and swept the curtains shut. “We don’t need to give the lighthouse keepers a show now, do we?” he joked. He grabbed his toilet bag and pulled out a butt plug and some lubricant. “Let’s prepare your asshole good…— I don’t want to hurt you — at least not too much,” he said with a mean grin.

Are you ready for this, Jel?” Chris asked.
Ready as I’ll ever be, honey,” Jelmer said lovingly. Extremely slowly, Chris rotated the butt plug against the rim. Jelmer relaxed his sphincter, and the toy was virtually sucked halfway up his bum.

Now… there you go, mate — you got it. Let your ass get used to it for a moment,” Chris said, slowly stroking his own meat with his still-lubed hand. “If you want, I can fuck you with my toy too — but that’s up to you, bro,” Chris winked. After a while, Chris began to pump the plug in and out of Jelmer’s ass, going ever so slowly, deeper and deeper into his gut.

Oh God!” Jelmer exclaimed as he felt the thickest part of the plug stretched him open. “FUCK ME!
Christopher smiled down at Jelmer and slid the toy out, replacing it with the tip of his slick dick against the back door. Using the battering ram to force entry — not as slow or gentle as the toy — Chris slid inside in one long, relentless push.

Oh… Fuck — that’s big! Oh God… How nice… Fuck,” Jelmer cried out. His eyes were wide, looking a little scared and amazed, but he didn’t want to stop.
You’ve got to tell me if it hurts too much, Jel,” Chris said, leaning over to kiss him.

Fuck me, Chris — I want you in me — Take me, I’m yours!” Jelmer responded. Chris pushed in a little deeper, watching Jel closely. Jelmer grabbed Chris by the thighs and pulled him deeper into his gut. “Fucking hell, dude! You’re so big,” Jelmer exclaimed.
Yeah… And you’re going to get all of it… Hard — and deep,” Chris yelled in ecstasy.

With a deep sigh, he pressed forward and shoved all of himself deep into Jelmer’s ass. Jelmer screamed. Chris stopped all movement and dropped onto Jel, letting him get used to the enormous cock.
I love it — you fill me so fucking nice,” Jelmer panted after a while. Chris started to rotate his hips, pumping Jelmer’s fuckable ass open.

After a while, he pulled his cock out. Jelmer looked disappointed.
Not to worry, bro — I’m not done with your asshole. But as they say in the building trade: ‘Safety first’.
With a grin, he grabbed a condom and rolled it over his raging, hard cock. Chris flipped Jelmer onto his stomach and shoved two pillows under him. He rubbed his spit-lubricated hands over the rubbered head and plugged Jelmer’s slick ass again.

Jelmer got fucked hard and deep. The guys were in total ecstasy. The leather jacket flapped as Chris rode his best friend’s ass to oblivion and back. Man, he felt so powerful and in control; it was dangerous. Dangerously good. Much better than all the women he’d bedded. This really was what he had been looking for.

Chris listened as Jelmer moaned and groaned. His own breath hitched as he got close to yet another ejaculation. He noticed his buddy’s grimaces of pain and slowly pulled back.
Let’s try a different position,” he said, forestalling the disappointed edge escaping Jelmer’s lips. Chris turned his buddy over and slid, with an extra dose of lube, right back inside, ready to take this to the climax.

Jelmer pulled Chris onto his chest as he kissed him. Slowly, Christopher increased the speed, banging his hips against Jelmer’s cheeks, feeling the leather as he embraced the onslaught. His eyes rolled into the back of his head as Chris unloaded his nut, blowing up the party balloon to full capacity.
After about ten minutes, Chris got up to pee. He took his diary to make a personal note.

• Dear Diary: May 1st — 00:18 AM.
What a day! I wouldn’t mind a repeat. I had sex with three men. Ha, what would the guys at home say? This wasn’t bad. Not bad at all. Much more enjoyable than with the women I dated before. I guess this is a good start. Let’s see what the rest of the holiday brings.
I fucking love this jacket. I know it’s not mine to keep — well, unless no one claims it. I hope he doesn’t. It suits me. At least I got to try it on for looks. And Jelly-belly’s ass was a nice fit, too. Fuck, I nearly raped his hole. I felt so fucking dangerous.

When he got back from the tiny toilet, he said to Jelmer, “See, Jel — it wasn’t so bad. I’m into this kind of shit, too! Want to sleep over tonight?” Christopher asked, exhausted. It had been a long, hard day. Night had fallen, and the calendar had rolled over into May.

Chris knew that Jelmer lived in a little farmhouse halfway across the island. It wasn’t far by car, but he loved the idea of sleeping with Jelmer to talk more about what had happened and his experiences on the ferry. The guys chatted and drank a few more beers, and late that morning, they curled up in the queen-sized bed together, as if this were the norm for them, in search of some much-needed rest.

• Continued in chapter 3 •


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 - January 2026

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