Gay Men in Underwear Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about underwear fetish or men in underwear.

How I Became my Roommates' Slut (ch. 23)

By Sufficient_Offer 18 Apr 2026

He balled up the dirty, cum-soaked fabric and shoved it against my mouth. “Open wider.” Fuck… he wants me to eat it?

9.1 (58) 5287 9 Min Comments

The Hillbilly Incident

By Borehamwoodman 17 Apr 2026

This is part one of a four-part story that sees Ethan, John and me as good friends enjoying a vacation, mountain biking through the Appalachians, when we decide to take a break to enjoy a beer and sandwiches. We didn't know we were trespassing until Hal came along and found us and made us an offer we couldn't refuse.

9.5 (31) 1886 34 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.

8.2 (11) 787 10 Min Comments

My Russian Billionaire Boss (ch. 2)

By StoriesByTroy 12 Apr 2026

A young hacker's life is turned upside down when a corporate CEO blackmails them into committing corporate espionage.

9.3 (45) 2914 10 Min Comments

Dan's Wrestling Adventures (ch. 3)

By HandyDan 11 Apr 2026

Dan is desperate to get his first win but can he outlast The Twink's endurance?

9.9 (10) 1241 16 Min Comments

Wedgied at the Arcade

By HandyDan 5 Apr 2026

Dan heads to the arcade to try and get the Hi-score but someone else has plans for him...

6.8 (15) 2868 4 Min Comments

The Big Hike (ch. 10)

By Borehamwoodman 1 Apr 2026

Steve and Billy returned to Vancouver Island with four kids in tow. Child services surprisingly gave them a clean bill of health. Jesse and Eli became the "responsible" big brothers. Billy returned to his art while Steve continued his career. Brian and Rob adopted the position of being the only mature men in the family dynamic.

9.9 (16) 448 69 Min Comments

The Big Hike (ch. 9)

By Borehamwoodman 31 Mar 2026

The its wedding and changes are afoot for Brian and Rob, along with Billy and Steve, with an impending change in the whole relationship.

8.7 (13) 288 35 Min Comments

The Big Hike (ch. 8)

By Borehamwoodman 28 Mar 2026

Brian and Rob are planning the wedding. Steve decides to seek sanctuary from the madness. Jesse and Eli want to buy a yacht. Rob and Brian argue over shellfish, and Hari reaches out to the troubled men, offering much-needed distraction while Billy continues to paint.

9.3 (13) 339 40 Min Comments

The Big Hike (ch. 7)

By Borehamwoodman 27 Mar 2026

Jesse and Eli celebrate losing their virginity. Brian has a big announcement, and Steve decides to learn about tantric meditation, much to the delight of Billy, who is also willing to learn more.

9.5 (10) 465 37 Min Comments

The Mechanic

By Will Bottom 27 Mar 2026

Bryce knew nothing about how a car worked, but he did know that when a knocking noise started coming from the engine, it was time to visit a mechanic.

8.3 (67) 4441 3 Min Comments

My Roommate's Older Brother

By Nico Reyes 26 Mar 2026

Milo’s roommate Taylor leaves for the weekend, leaving his older brother Cruz to crash at their apartment. The tall, heavily tattooed construction worker immediately takes over the space, stripping down to nothing and jerking his thick cock openly on the couch like he owns the place.

9.2 (143) 10823 6 Min Comments

The Big Hike (ch. 6)

By Borehamwoodman 26 Mar 2026

Billy and Steve settle into their new life, buying a home with Brian and Rob moving in as well. Steve gets introduced to Brian's machine, and Jesse and Eli apply to become life models for Billy.

9.8 (16) 446 46 Min Comments

The Big Hike (ch. 5)

By Borehamwoodman 24 Mar 2026

Steve and Billy decide to make Vancouver Island their home. Priority is buying a home. Second priority... sex is always a priority for them, but they soon broaden their horizons, realising that the island has more to offer than just Brian and Rob

9.2 (20) 426 38 Min Comments

The Big Hike (ch. 4)

By Borehamwoodman 21 Mar 2026

Billy was put to bed to recover. Brian, Rob and I went downstairs for a drink and a debrief, Steve, picking up the vibe that confessions were coming and perhaps a little overdue.

9.3 (18) 567 26 Min Comments

Galactic Husbands (ch. 5)

By Lance Gigas 20 Mar 2026

Lance wakes up in the underwear of his other husband, the 40-stories tall Wolfian Henry.

7.5 (2) 316 10 Min Comments

How I Became my Roommates' Slut (ch. 14)

By Sufficient_Offer 18 Mar 2026

Adrien and Steph plan to visit a Musuem. Maybe it's a bit difficult for our little historian to focus though, because his mind keeps coming back to cock.

9.1 (67) 5231 9 Min Comments

Taken in the Woods

By Skyreader 17 Mar 2026

The scene: The wilds of Massachusetts on a hot summer day. The characters: Me, my best friend Bram and two redneck types.

9.0 (70) 3170 11 Min Comments

The Big Hike (ch. 3)

By Borehamwoodman 17 Mar 2026

Steve and Billy eventually make it to Vancouver and then catch the ferry to Victoria on the last leg of their journey. Brian and Rob meet them at the ferry terminal with a few friend to congratulate them.

9.5 (25) 773 30 Min Comments

Practicing Cum Control With My Straight Best Friend (ch. 2)

By DanXWrites 16 Mar 2026

After weeks of increasingly intimate nude edging sessions, Tyler times Noah as he strokes nonstop. Noah hits exactly one minute and climaxes hard. Tyler praises him, kisses him softly on the lips, grins, then says they move to stage two before leaving, leaving Noah breathless and wondering.

9.0 (39) 3322 7 Min Comments

The Big Hike (ch. 2)

By Borehamwoodman 16 Mar 2026

Steve and Billy made a decision and resumed the big hike together, getting to know each other even more. In need of a break, they rest for a week, spending time together for educational and relaxation purposes, sealing their relationship, each day.

9.8 (26) 1073 35 Min Comments

The Big Hike

By Borehamwoodman 15 Mar 2026

This is Part One of Steve's new story seeing him attempt the Trans Canadian Trail that goes from Nova Scotia to Vancouver Island. Just a short walk as they say but he's doing it as a bet between him and Brian his friend who lives in Victoria, BC.

9.9 (25) 2147 35 Min Comments

Under the Crimson Swoosh (ch. 12)

By BJCS Mines 12 Mar 2026

Wyatt’s quiet sophomore year is nearing its end when Sigma Chi president Tate demands Wyatt and Elliot prove their loyalty on his UREC pickleball team. Their imminent trust funds mean nothing if they can’t win—and refusal isn't an option. On the court, the past serves back. Hard.

9.8 (25) 713 18 Min Comments

Dorm Bro: Winter Loaded (ch. 4)

By DanXWrites 7 Mar 2026

My Roommate Invited His Friend Over… and Offered Me Up

9.3 (73) 6612 7 Min Comments

Recovery (ch. 42)

By Furball 6 Mar 2026

Helmut takes Joey to his second circle jerk in hopes of a repeat performance, but all Joey can think about is Ben.

9.4 (8) 180 7 Min Comments

Outback Undies (ch. 4)

By Borehamwoodman 4 Mar 2026

In the final part, Steve, Brryn, and Neil have to do a photoshoot for the marketing material, then decide that a beer in town is much needed. Walking into the town's bar, they are greeted with silence until they see the poster Neil had put together.

9.9 (24) 1241 27 Min Comments

Outback Undies (ch. 3)

By Borehamwoodman 3 Mar 2026

We had to get Mr and Mrs Henderson on our side to sell the new brand of Outback Undies at their shop. The best way was to hold a fashion show, and all of us decided to be models helped with Bryn's mother preparing budgets and business plans.

9.6 (23) 649 22 Min Comments

Dorm Bro: Winter Loaded (ch. 3)

By DanXWrites 1 Mar 2026

My Roommate Finally Snapped and Bred My Juicy Ass All Night Long

9.6 (119) 10122 9 Min Comments

Outback Undies (ch. 2)

By Borehamwoodman 28 Feb 2026

After all the measurements were noted and sent, all the lads had to do was wait for the samples to arrive. When they did arrive, the lads knew they were on a winner, but they had to persuade Mr and Mrs Henderson to sell their brand of undies instead of the tired and ill-fitting Kangaroo briefs sold in the local store.

9.8 (22) 831 24 Min Comments

Dad's Helping Hand II: Camp Harding (ch. 2)

By M. Harding 27 Feb 2026

Ch. 2: His Special Touch // Richard Harding has a morning swim on his grandson's 18th birthday, sensing change in the air, and gets roped into offering his massage skills when one of their crew gets injured.

9.4 (35) 4169 22 Min Comments

Outback Undies

By Borehamwoodman 25 Feb 2026

Part One of this story sees Bryn have an idea he shares with his mates on his eighteenth birthday. "Lets design and manufacture our own undies instead of the Kangaroo brand we're forced to wear." Steve, Eli, Jamie and Neil initially reject the idea but come on board when the idea becomes more than an idea.

9.6 (35) 1945 39 Min Comments

Recovery (ch. 32)

By Furball 24 Feb 2026

Joey receives good news about Ben's improvement, and when he returns to the boarding house he is surprised to find Kevin and Helmut there and a feast ready to be served. Kevin shares an unexpected secret with Joey while Helmut gets upset with Phil.

9.4 (9) 107 7 Min Comments

How I Became my Roommates' Slut (ch. 4)

By Sufficient_Offer 23 Feb 2026

Steph is about to have his first swimming practice with the cocky Julien, things are about to turn wet and sexy.

9.3 (96) 8462 9 Min Comments

A Thief of Hearts

By Will Bottom 22 Feb 2026

Love envelopes you when you least expect it.

7.9 (12) 436 3 Min Comments

My Underwear Obsession Explodes (ch. 2)

By Will Bottom 20 Feb 2026

In less than 24 Hours Life Erratically Changed.

8.1 (23) 1659 2 Min Comments