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.

The Big House In The Country

By Borehamwoodman 16 Apr 2025

Daniel has applied for a job as a companion to a man called James. James is rich, owns a big house in the country and is looking for a companion to share his life. Daniel is effeminate and subservient in his demeanour. Marion, the housekeeper, approves and supports the growing friendship. What could go wrong?

9.1 (26) 2151 35 Min Comments

Step Brother Catches Me Sniffing His Underwear

By StoriesByTroy 15 Apr 2025

My Step Bro Catches Me

9.2 (105) 7252 3 Min Comments

A Week in Paradise (ch. 4)

By Beefy Colby 10 Apr 2025

During their holiday in a clothing-optional resort, Bruno’s Daddy gets more and more control over him, showing him new things and turning him into a real dirty slut.

9.8 (51) 5107 10 Min Comments

Oh, Henry! (ch. 3)

By Great Dane 7 Apr 2025

Henry, a notorious top who, due to his athletically honed physique and massive cock, had earned the local title of “King of the BBC Gang Bangs”. His aggression was legendary; he had only one gear. But tonight that would change forever.

9.5 (37) 2153 12 Min Comments

Ollie's Weekend (ch. 3)

By Mark Mortland 6 Apr 2025

Ollie and Corey's first night together hits a few bumps and Ollie's first morning with the dads gets a little embarrassing. But nothing compares to Corey's stories. After solving a hard problem, the boys finally start their bike ride through Fort Worth.

9.7 (48) 728 27 Min Comments

Gay Train on the Public Beach

By Aussie "Speedo" Guy 4 Apr 2025

My two fuck buddies finally meet and we have a day at the beach. It started with some road head before we even hit the beach. In the dunes, we couldn't wait to get inside each other and while I fucked Matt, my young Asian fuck buddy, fucked me.

8.9 (26) 2891 11 Min Comments

Oh, Henry! (ch. 2)

By Great Dane 2 Apr 2025

Against all odds, Thomas, the subject of a gang bang, and Henry, one of his assailants, meet for an actual date. But to their mutual surprise, it becomes clear that they each want a very different experience than the last time they met.

9.6 (40) 2382 12 Min Comments

Speedo Universe

By Ravy 2 Apr 2025

The protagonist lands in a weird Universe- where everyone wears speedos

7.7 (16) 2703 7 Min Comments

Rookie in the deep end (ch. 3)

By ShawnRs 1 Apr 2025

I go on a first date with Brent. He helps me be desperate, plug-stuffed exhibitionist, trembling in public under a handsome man's thumb—and loving every second of it.

9.8 (54) 4563 18 Min Comments

Rookie in the deep end (ch. 2)

By ShawnRs 22 Mar 2025

Not quite ready to be an exposed slut in a thong at a swim practice so the universe seems to have its own plan.

9.3 (63) 5621 8 Min Comments

Cody Burden has a Rough Night

By Pup Wedgie 21 Mar 2025

Cody Burden, a humiliation content creator has a group of his fans find him.

8.7 (13) 5999 37 Min Comments

Rookie in the deep end

By ShawnRs 21 Mar 2025

I’d always been a broad all-American stud, someone to be admired—but my small dick always got in the way of my confidence. Fresh in Australia, I met Brent, a cocky Aussie who saw right through me. He didn’t just admire me—he claimed me. Now I'm not just some hot guy; I'm his toy, his plaything, his caged sub. And he wants everyone to know.

9.6 (93) 9356 17 Min Comments

A Week in Paradise (ch. 2)

By Beefy Colby 16 Mar 2025

After meeting the daddy of his dreams, Bruno discovers his exhibitionist side - first hooking up with a stud in the resort, then giving a special performance for his daddy.

9.5 (106) 6867 10 Min Comments

Sanctuary In The Wilderness

By Borehamwoodman 27 Feb 2025

Steven managed to escape from a gang finding himself running for his life in the Yukon. Whether by fate or design, his escape ended with him going over a cliff only to be found by John, a mountain bear of a man who saved him and in the process saved himself. This is Part One of Two and not much sex in this. Part two moves sex up the ladder.

9.6 (35) 1530 37 Min Comments

Love Can Be Blind To the Point You Don't See It until It Hits You (ch. 2)

By Borehamwoodman 25 Feb 2025

Steven, Rachel and Josh become better friends and Josh has a desire to visualise Steven and to ride Samson bareback. Samson is fine about it but Steven suggests he shares the experience with Josh since he cannot see.

9.5 (20) 688 34 Min Comments

Love Can Be Blind To the Point You Don't See It until It Hits You

By Borehamwoodman 24 Feb 2025

This is part one of a new story: Steven and Rachel's life is upturned when Josh and his mother move into the property next door. Josh is blind but that doesn't hold him back when he finds friendship with Steven

9.5 (41) 993 21 Min Comments

Detective Mark Stone's Undercover Assignment (ch. 2)

By Archer25 20 Feb 2025

Detective Stone reports back to the strip club for his first night as an undercover agent and has to entertain a bachelor party of twinks and they make him pay for all the jocks who used them in the past.

9.6 (107) 5255 30 Min Comments

Addicted to Piss (ch. 2)

By Michael Dee 19 Feb 2025

Ash explores his piss kink further.

9.3 (66) 6236 10 Min Comments

Love Found In South Carolina (ch. 3)

By Borehamwoodman 19 Feb 2025

Tim and Mark plan their wedding as their relationship evolves. Mark's sister arrives early for the wedding and the three of them become friends and not just family. What could happen to change things?

9.9 (29) 930 29 Min Comments

Love Found In South Carolina (ch. 2)

By Borehamwoodman 18 Feb 2025

Tim and Mark have fallen in love and their relationship continues to evolve. Tim's parents continue to monitor the progress of their plan sitting on the veranda each evening feeling satisfied with the good choice of a companion for their son although they still had doubts about the whole thing. This is part two of my three-part love story.

9.9 (39) 1016 30 Min Comments

Love Found In South Carolina

By Borehamwoodman 17 Feb 2025

Tim was a shy young man. Joe and Linda his parents wanted their son to embrace his sexuality which was quite obviously not the conventional expected in rural South Carolina. Linda came up with a plan. They would hire a summer companion for him. This is part one of my new story. I hope you enjoy it.

9.7 (68) 1894 29 Min Comments

Captured On Canvas In The Isles of Scilly

By Borehamwoodman 15 Feb 2025

John is an artist. Steven is a visitor who admires beauty and is captured by John not just on canvas, but emotionally and physically on the island of Samson in the archipelago known as the Isles of Scilly.

9.6 (13) 909 60 Min Comments

Jeremy Out of Control (ch. 2)

By WedgieLover 13 Feb 2025

This chapter covers the next man to take advantage of Jeremy’s curse. How will he be humiliated this time and what’s to come before graduation day?

6.9 (15) 3128 6 Min Comments

A Round Of Golf Requires Firm Balls

By Borehamwoodman 12 Feb 2025

Steven meets Jack at a golfing hotel and teams up with him for a round. They managed 9 holes before distraction but they managed to finish the game in Jack's room.

9.4 (47) 1631 16 Min Comments

Jeremy Out of Control

By WedgieLover 12 Feb 2025

Jeremy our main character, is sharing his story on the curse laid upon him by his mother prior to leaving his life. It’s hell on earth for him, but pleasure to all others.

7.6 (14) 4520 9 Min Comments

Ben's Weekend Trip to Utah (ch. 25)

By BJCS Mines 31 Jan 2025

During a shopping trip at Costco with Ben and Caleb, John teases Caleb about the new underwear Caleb picks out. Things take a turn when they return home to discover something about JP they all didn't know. The situation escalates but ultimately leads to a moment of intimacy between Ben and JP.

9.6 (24) 1342 19 Min Comments

Gym Seduction

By lickme 31 Jan 2025

Fun in the sauna and shower for a first timer with a guy

8.2 (66) 5121 4 Min Comments

Mr Harrison the Sex Therapist (ch. 2)

By Borehamwoodman 31 Jan 2025

Steven returns to Mr Harrison for another session that might be his last with the guiding hand of Ms Smith who knows a secret. Steven suspects Ms Smith is a man but he is more interested in a cure for his panic attacks than what the supportitng sex therapist is wearing.

9.3 (31) 1023 28 Min Comments

Mr Harrison the Sex Therapist

By Borehamwoodman 28 Jan 2025

Steven suffers from panic attacks and his neighbour, Mr Harrison thinks he knows what triggers them. He extends an invitation to Steven to attend a free-of-charge session knowing that the young man will benefit from his expertise.

9.1 (44) 1603 15 Min Comments

My Sister the Matchmaker

By Borehamwoodman 22 Jan 2025

Rachel is fed up with her brother and plots a relationship with David who has the hots for Steven. First, she has to get him to wear tighty whities which David loves Steven wearing.

9.7 (23) 1805 40 Min Comments

The Rugby Team's Toy

By rt1047 20 Jan 2025

Derek Walker has taken a job as the equipment manager for the college rugby team during their summer training camp to help pay tuition, but after a chance encounter in the locker room with senior Ethan Frey, he finds there might be much more fun to be had at camp than a game of rugby

9.2 (210) 19504 10 Min Comments

A Lazy Afternoon (ch. 3)

By Borehamwoodman 19 Jan 2025

Our heroes, Steven and Richard wake up in the same bed. Selina brings bagels for breakfast and someone suggests a family picnic. What could go wrong?

8.8 (36) 1148 17 Min Comments

A Lazy Afternoon (ch. 2)

By Borehamwoodman 18 Jan 2025

Steven and Richard decide to spend a day by a lake inland this time, enjoying the warmer water and scenery. Steven's mother suspects something is going on and provides a solution most unexpected.

9.5 (49) 2119 35 Min Comments

A Lazy Afternoon

By Borehamwoodman 17 Jan 2025

Richard, Steven's neighbour, invited him to an afternoon hike to the beach. What started as a simple invitation soon became something more which would change their lives forever.

9.2 (86) 4559 18 Min Comments

A West Highland Journey (ch. 3)

By Borehamwoodman 15 Jan 2025

This is part 3 of our heroes West Highland journey. Steven and Hamish wait for the waiter to finish his shift. Hamish explains to Steven that Andrew enjoys a good spanking from time to time and Steven can provide essential support for the night's fun and games.

9.2 (32) 940 11 Min Comments