Gay Holiday Sex Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about men and gay sex during holidays.

Shadows of Surrender (ch. 10)

By Exposed 9 Jun 2026

The group rewards themselves with a luxury Greek resort vacation. Alex stays completely naked the entire week, becoming a public attraction. He performs on stage at a bondage nightclub and models for the resort’s official nude promotional campaign.

9.6 (14) 598 11 Min Comments

The Cabin (ch. 3)

By CassiNotSoSure 6 Jun 2026

(Ch. 3 - The Boss's Bedroom) Caleb's night is not finished yet. After his 'self-care' was witnessed by Julian, the older gentleman takes him to clean off before they spend the night in the Master Bedroom together.

8.4 (20) 1129 8 Min Comments

The Cabin (ch. 2)

By CassiNotSoSure 5 Jun 2026

Short chapter. Caleb struggles to comprehend his first interaction with Julian. After a restless night, his excitement returns and he tries something new.

8.4 (21) 1285 2 Min Comments

Amster-Damn Hot (ch. 10)

By The Men We Crave 4 Jun 2026

Two best friend. One wild holiday. A romantic awakening.

8.7 (13) 485 10 Min Comments

The Cabin

By CassiNotSoSure 4 Jun 2026

This is based on a true story. Characters and locations have been changed. Caleb goes on a yearly trip with his Dad, Mark, to a lakeside cabin. This time, they go to to Mark's boss's cabin. After Mark is delayed, Caleb's introduction with Mark is not what he expected.

8.3 (33) 2343 8 Min Comments

Amster-Damn Hot (ch. 9)

By The Men We Crave 3 Jun 2026

Two best friend. One wild holiday. A romantic awakening.

8.7 (10) 552 10 Min Comments

Amster-Damn Hot (ch. 8)

By The Men We Crave 2 Jun 2026

Two best friends. One steamy, life-changing trip. A night of passion. Repurcussions for life. A romantic, youthful story.

8.5 (9) 490 8 Min Comments

My Uncle's Eight Inch Cock

By Prikz 30 May 2026

I loved staying with my uncle in Spain, he was a sexy randy Bi man who liked to fuck me with his eight inch dick. When he introduced another guy Brian we had the fucking time of our lives.

9.3 (70) 3643 10 Min Comments

Dad's Helping Hand

By M. Harding 18 May 2026

Ch. 1: What Happens In Rome... // Matt Harding is rich, fit, and successful. But he also has a secret. When he takes his dad Richard, a retired football coach, on vacation, one night changes them forever -- and ends up affecting their whole family. (updated with new prologue)

9.3 (182) 22902 22 Min Comments

Gay Summer Holiday (ch. 19)

By StrykerJ 13 May 2026

Christopher found on the Island what had eluded him back at home. This working holiday had turned into an extended stay. He found true love and dared to take the plunge. Chris took his man, Wyatt, on an in-depth house tour, hoping they could make it into their home. And he gave his short Asian guest the look he deserved: a butch Leather Jacket.

9.5 (42) 534 14 Min Comments

Gay Summer Holiday (ch. 18)

By StrykerJ 6 May 2026

Sometimes, the truth is weirder than fiction. If you can’t change it, let it go. Find your fun somewhere else. An unexpected midnight visitor, a phone call with home, and some rough outdoor anal, with a lifeguard you love, can be just what’s needed. Christopher thought so when the final puzzle piece finally fell into place.

9.6 (32) 522 15 Min Comments

Garcia Family (ch. 5)

By BigMilky 4 May 2026

Nathan's hot summer vacation continues at full speed and the hot action continues happening but who is fucking who this time?

9.0 (27) 2494 25 Min Comments

Garcia Family (ch. 4)

By BigMilky 2 May 2026

Nathan's hot summer vacation continues with more hot action but with who?

9.3 (26) 2591 24 Min Comments

Dad and Son Cruise to a New Understanding (ch. 3)

By Graham Estes 1 May 2026

As the cruise nears its end, Andrew and Michael’s bond deepens fast. Strip card games lead to total nudity, playful cock comparisons, and candy-firing contests. On their final night, they step onto the balcony for an intense shared release under the stars. What started as a simple trip becomes something far more intimate and unforgettable.

9.6 (39) 1942 17 Min Comments

Dad and Son Cruise to a New Understanding

By Graham Estes 29 Apr 2026

Michael and 20yo son Andrew share a upgraded cruise suite with one king bed. Over three days they bond through ship fun, rock climbing, off-road driving, drinks & cards. Andrew (recently gay) grows fascinated seeing his athletic dad casually naked; Michael stays relaxed. Subtle morning touching hints at tension.

8.9 (33) 2934 17 Min Comments

Dad and Son Soak up the Sun (ch. 2)

By Graham Estes 23 Apr 2026

On their final full days in Key West, Dan and Kyle’s bond deepens through a fishing trip, a surprise tropical storm, and increasingly intimate “soaking” sessions. From shared showers and massages to raw, bare connection while spooning, father and son explore new levels of trust and pleasure before heading home closer than ever.

9.4 (47) 2434 21 Min Comments

The Lad's Holiday (ch. 3)

By Spiritual Camera 23 Apr 2026

The heat between Michael and Paul grow as things move from entertaining the girl to exploring each other

8.6 (22) 1247 9 Min Comments

Gay Summer Holiday (ch. 15)

By StrykerJ 18 Apr 2026

After a long, hard day’s graft, Christopher set the plans to work. He had a path to build and Japanese guests to entertain. Chris found the poles he wanted. Wyatt, his friend, was rapidly falling in love with him. And with the other pole, he constructed a landmark flag. And to anchor himself on the Island, he found himself a home.

9.6 (31) 493 16 Min Comments

Costa Rica (ch. 4)

By GrantsXploits 12 Apr 2026

Twunk wearing boxer briefs walking around resort grounds catches my attention and I offer to help him out of a frustrating situation.

8.1 (9) 695 10 Min Comments

Ethan and Alex (ch. 5)

By ScooterB 10 Apr 2026

In this fifth chapter of six, the two guys have a major disagreement before their time at the resort comes to an end.

8.6 (8) 286 21 Min Comments

Ethan and Alex (ch. 2)

By ScooterB 7 Apr 2026

Part 2 of 6. The exploration of their relationship continues.

9.7 (9) 869 16 Min Comments

Ethan and Alex

By ScooterB 6 Apr 2026

Part 1 of a 6-part story about two men who find each other when the resort where they both are staying accidentally double-books an island getaway for each of them.

8.5 (23) 1875 14 Min Comments

The Decorators (ch. 8)

By 243907 31 Mar 2026

We take a holiday, and have several sexual encounters

8.5 (9) 359 7 Min Comments

The Straight Boys Took Me On Vacation (ch. 18)

By Broken Boundaries 25 Mar 2026

I'm Tommy, 18 year old college freshman on a vacation with my 5 rich, str8 friends at a luxury resort we have to ourselves. With no girls around, they've been using me to explore all of their new, kinky fantasies. After a wild few days of serving their every whim, I was caught completely off guard when one of the boys came by for a private visit..

9.5 (37) 4438 12 Min Comments

Ben's Weekend Trip to Utah (ch. 33)

By BJCS Mines 23 Mar 2026

John's detour to Buc-ee's was supposed to be a joke. But when Ben unrolls the Cat's Meow bag in a Rocky Mountain campground, the supple nylon brings back memories he thought he'd buried. This time, with John inside him, Ben finally understands the difference between fumbling in the dark and being held.

9.5 (28) 538 22 Min Comments

Gay Summer Holiday (ch. 8)

By StrykerJ 21 Feb 2026

Being called a liar by his best friend hit him hard. And all Chris did was recall the amazing encounter with the Island’s only black dude. But sometimes you need to endure a little drama to solidify a relationship. This was a weekend from hell, and Chris ended up in the wrong bed but had no regrets about it. Jelmer just needed a bit more time.

9.8 (51) 522 18 Min Comments

Gay Summer Holiday (ch. 7)

By StrykerJ 14 Feb 2026

When you fall off a horse, you need to hop right back on. This holds true for Chris, too. He found a changed Jelmer. He needed his space after their shopping trip to Amsterdam. And opportunities arose when the BBC of Officer Tom wanted more than an autograph. He wanted to fool around with the white boy and knew the perfect spot with a gloryhole.

9.8 (51) 1183 17 Min Comments

Gay Summer Holiday (ch. 6)

By StrykerJ 10 Feb 2026

Chris and the guys take ‘a walk on the wild side.’ Shopping and dancing in Amsterdam. Finding a kinky leather fetish shop to get kitted out and a raunchy nightclub with a leather and denim theme where they learn about subservience and obedience from a master and his sub. The building work on the Island had to take a backseat for a day or two.

9.7 (54) 900 18 Min Comments

The Spa Experience

By Happy to be Bi 10 Feb 2026

Horny story of 3 men in a hotel spa area

9.4 (12) 2919 17 Min Comments

Straight stud on holiday dominates me

By cbrguy 5 Feb 2026

This is a fictional story about an older gay man on holiday inviting a straight guy to be his top.

8.8 (22) 2045 6 Min Comments

Gay Summer Holiday (ch. 5)

By StrykerJ 3 Feb 2026

Christopher earned a break. With the cabins stripped and supplies ordered, he spent a few days at Jelmer’s place, stripping his lover of all modesty. A long beach walk led them to a group of senior Scouts in a public restroom, all willing to earn their ‘ass-fucking badges’ under Chris’s stern, expert command. The Island is getting wilder every day.

9.7 (55) 1278 15 Min Comments

Gay Summer Holiday (ch. 4)

By StrykerJ 2 Feb 2026

Christopher’s fame on the Island grew in leaps and bounds. Not just for singing with his idol, but for the daring rescue of a friend. He prevented a group of predatory bikers from abusing the young lad, humiliating them to the bone and blackmailing them into giving up their leather gear. Running them off the Island he had grown to love so much.

9.7 (63) 1167 17 Min Comments

Gay Summer Holiday (ch. 3)

By StrykerJ 1 Feb 2026

Christopher’s working holiday had started. And that in more ways than one. He discovered something new. He liked sex with men and sex in kinky leather. And the Islander group of guys he used to hang out with delivered.

9.6 (67) 1332 15 Min Comments

Gay Summer Holiday (ch. 2)

By StrykerJ 31 Jan 2026

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.

9.7 (68) 2203 20 Min Comments

Gay Summer Holiday

By StrykerJ 28 Jan 2026

Christopher (19) had finished school with excellent marks. He was set to go to a technical college. He planned a 4-month working vacation on his favorite paradise Island. To discover himself. The ferry ride over started out great. He had his first anonymous encounter with a burly leather-wearing man. The nasty blowjob gave him a taste for more.

9.4 (111) 5170 16 Min Comments