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.

Sam's Secret Campus Jackoff Spot (ch. 13)

By Alt Iceman 4 Nov 2025

Freshman twink Tyler does a weekly private cam show, and his boyfriend Sam normally watches. Meanwhile, Sam's straight roommate Dave is starting to get serious about a girl, and needs Sam's help to pick out clothes, and with a harder problem before the big night. Sam is sexiled and spends the night down the hall and the talk turns interesting.

9.6 (29) 1418 25 Min Comments

Down on the Farm (ch. 4)

By Will Bottom 3 Nov 2025

Timmy quits the Jones Farm to return home to his mother after his father passes away. The new Farm hand was a seven foot tall Black hunk with the muscles of a God and a large member swinging between his legs.

9.0 (35) 3834 3 Min Comments

Straight Muscular Jock Massages Gay Men

By DanXWrites 2 Nov 2025

'Straight Muscular Jock Massages Gay Men' is a gay erotic story about a closeted engineer who books a massage, only to discover the masseur is his long time crush - the straight jock he never stopped fantasizing about.

9.5 (96) 7144 16 Min Comments

The Dig

By Borehamwoodman 1 Nov 2025

Steve and Gerry are archaeologists with a job to do. Dig an exploratory trench at an ancient barrow. Simon, a woodman in the New Forest, happened to pass by and, seeing the two PhD wearing nothing but their briefs, he invited them to the ancient stone circle nearby for a few beers, history stories and something to eat. What could go wrong?

9.4 (23) 1398 29 Min Comments

Straight Boy desperately needs money (ch. 3)

By Will Bottom 31 Oct 2025

Bills. Bills. Bills. To get out of debt Dick Hunt decides to become a contestant on Bankrupt Straight Dudes but a freaky surprise awaits him.

9.1 (33) 2981 6 Min Comments

Canary Islands Model

By GrantsXploits 30 Oct 2025

My husband and I are on vacation. We watch as a male underwear and swimwear model has some trouble during a photoshoot, so I help him out.

9.3 (48) 2723 14 Min Comments

Ben's Weekend Trip to Utah (ch. 29)

By BJCS Mines 29 Oct 2025

Ben’s Thanksgiving trip to meet John’s Wisconsin family is a minefield of polite interrogation and unspoken rules. Navigating his boyfriend’s conservative Catholic home is hard enough, but the real test comes at night, inside John's childhood bedroom, their secret intimacy feels more forbidden and more thrilling than ever before.

9.4 (26) 744 18 Min Comments

Down on the Farm (ch. 3)

By Will Bottom 29 Oct 2025

After a week of trading sons. Luke learned how to take a big cock down his throat and up his ass with no problem. Lance taught Ben how to suck dick, fuck butthole, kiss a man & how to finger your bottom & eat ass. They came together at the Sheriffs home for a barbecue.

9.1 (34) 3428 3 Min Comments

Out With The Old. In With The New. (ch. 2)

By Borehamwoodman 29 Oct 2025

Justin arrives back from an evening with Richard. Liam, his brother, couldn't sleep and saw Justin walking home, naked. One thing led to another, and Richard once again becomes a counsellor, providing practical support for Liam's conflicted desires while Justin sleeps in late the next morning.

9.5 (25) 932 22 Min Comments

Down on the Farm (ch. 2)

By Will Bottom 28 Oct 2025

While Grandpa Jones and the Farm workers are at County Fair, Heath and Lance met the new sexy Sheriff with a big surprise.

8.8 (53) 4415 6 Min Comments

Sam's Secret Campus Jackoff Spot (ch. 12)

By Alt Iceman 28 Oct 2025

It's the week before Thanksgiving, and freshman boyfriends Sam and Tyler are just counting down the days until break. They head back to their "secret" bathroom for some fun, but leave with less than they brought, and then have Tuesday night together, after Tyler's webcam show.

9.4 (28) 1220 22 Min Comments

Straight Boy desperately needs money (ch. 2)

By Will Bottom 26 Oct 2025

Three 'straight' men (Tad, Patrick and Duke) are given money to have sex with another man. Mr. Peni, the owner of Bankrupt straight Boys is a rich dirty old man. who loves making these shows.

8.8 (53) 4104 5 Min Comments

Down on the Farm

By Will Bottom 24 Oct 2025

Six sweaty hot men working on a farm in Nebraska. The family leader was strong Grandpa Jones, a stepson-in-law and his young grandson,19 year old Lance. The gay farm hands were Timmy, Miguel and Marcus.

8.8 (101) 7670 5 Min Comments

Spontaneous Encounters (ch. 2)

By Robbie Watkins 23 Oct 2025

This short story is part of a fictional anthology series based on my fantasies about everyday encounters somehow turning into sex with a dom-sub dynamic, told from the top's perspective. Each story can stand alone. If rough sex, humiliation and verbal degradation are your cup of tea, this series is for you!

9.1 (13) 1723 16 Min Comments

Straight Boy desperately needs money

By Will Bottom 23 Oct 2025

Finding himself broke, young Kyle Striker's rent is due in two days What can a straight boy do to make money in two days? Why Kyle is willing to do anything ... anything to make the money he needs.

7.9 (114) 9529 6 Min Comments

My Boss Moved In After His Divorce (ch. 3)

By DanXWrites 23 Oct 2025

After opening up about his divorce, Greg admitted to Alex how long it had been since he’d had any real intimacy, how months without affection or release had left him restless and horny.

9.3 (103) 6610 11 Min Comments

Out With The Old. In With The New.

By Borehamwoodman 22 Oct 2025

Richard Shaw arrives home to find his trusty boxers missing from his washing line replaced with pristine Y-Fronts and matching white vests. Flabbergasted and confused, the incident takes a turn for the curious when he receives a text message saying, "You will look good wearing these and please meet me at 7pm."

9.5 (28) 2275 32 Min Comments

My 18 year old nephew pulled me out of the closet (ch. 4)

By Will Bottom 21 Oct 2025

Troublemaker, Top man Ray, who orchestrated the Gang Bang of the new dancer, Peter. Ray was given the choice of being fired or having the new dancer, Peter McHenry, buttfuck him.

8.9 (18) 1245 4 Min Comments

Alpha's Dirty Secret (ch. 6)

By DanXWrites 19 Oct 2025

I should’ve let him leave. I should’ve just let Cole walk away, stroke himself off alone, and pretend this night never happened. But I begged. I begged him to stay. Called him sir. Promised I’d do better. So now I’m here; mouth sore, throat raw, and still desperate for more. He called me a mutt, and I fucking agreed. I wanted his cock so bad

9.1 (45) 5378 6 Min Comments

My 18 year old nephew pulled me out of the closet (ch. 2)

By Will Bottom 19 Oct 2025

The new stripper, Peter McHenry is causing waves and sexy thoughts with his new Boss and the hunky choreographer. He finds a home to stay in where the action is always hot!

8.6 (38) 1531 5 Min Comments

The Cambridge Don And His Appreciation of Classic White Briefs

By Borehamwoodman 17 Oct 2025

In this longer story than normal, Steve accepts an offer he can't refuse allowing Professor Nevis to explore his underwear fetish of inspecting young men in their classic white briefs. Steve is just the person to share with him and he might have another candidate for the professor to inspect at the same time.

9.8 (21) 1460 57 Min Comments

Posing In The Gym in Underwear

By DanXWrites 15 Oct 2025

Posing In The Gym in Underwear

9.1 (79) 5067 6 Min Comments

The Education of Billy Boy (ch. 3)

By Will Bottom 13 Oct 2025

Billy Boy meets his new boss, Sean O'Toole under strange but sexy circumstances. Big Jim, the photographer, gets Billy stoned and "things" happen.

8.8 (23) 1665 5 Min Comments

The Chosen Jock (ch. 6)

By Marathonbrad 13 Oct 2025

Pulse exploded with sound and color as Coach Franco guided me inside, his grip sure, his intent clear. Every head turned. The lights caught each line of my body—tight tank, sheer pants, red jock beneath. My heartbeat matched the bass; my body felt alive. That night, I wasn’t just watched—I was claimed, the athlete on display.

9.2 (29) 2933 31 Min Comments

The Education of Billy Boy (ch. 2)

By Will Bottom 12 Oct 2025

Billy Boy adapting to his new life. From his first Photoshoot with Big Jim to getting used to wearing only a jock at Tennis Club meetings. Not to mention dealing with the crush he has on his sexy boss Sean O'Toole

8.6 (56) 2514 5 Min Comments

My College Life (ch. 5)

By Thatdude 11 Oct 2025

The weekend has arrived and so had the thrid and final roommate! Jaxon wants to get to know the jock more, and also wants the jock to know him better, both inside and out, and the jock did indeed satisfy.

9.3 (52) 3800 11 Min Comments

The Education of Billy Boy

By Will Bottom 11 Oct 2025

After graduating from College our hero, Billy, embraces adulthood, a new job in a new city and seeks out new pleasures when he comes out of the closet

8.6 (57) 3335 5 Min Comments

The Journey of Randy Dix (ch. 3)

By Will Bottom 9 Oct 2025

Gossip fiend and hunk model Rod Harden's Saturday night is hijacked by two masked men with big dicks and a score to settle. And can you believe someone filmed Randy Jr. & Randy Sr. in the dressing room.

8.8 (21) 1507 4 Min Comments

The Journey of Randy Dix (ch. 2)

By Will Bottom 8 Oct 2025

After Randy Dix accepted a role in a gay sex film, a fear struck him. What if he's bad at it? He's never acted or had a dick up his ass or in his mouth, accept that one time with dad. But the exciting part was finally getting fucked!

9.2 (37) 1571 3 Min Comments

My Boss Moved In After His Divorce (ch. 2)

By DanXWrites 2 Oct 2025

I woke up with a hard-on. Sure, part of it was just blood flow, the usual morning wood, but that wasn’t the whole truth. Most of it was Greg.

9.4 (154) 9221 18 Min Comments

Nights in the dorms

By Alt Iceman 29 Sep 2025

I just met my dorm roommate today, but we know from Instagram that we're both gay and both single. I've wanted him since I first saw his speedo pic, and I think he wants me, too.

8.9 (106) 6713 10 Min Comments

His Son’s Future Classmate (ch. 4)

By Jack R 26 Sep 2025

Gabe comes home to find Tom ready to see him

9.6 (37) 2890 11 Min Comments

Sam's Secret Campus Jackoff Spot (ch. 9)

By Alt Iceman 24 Sep 2025

Sam and his roommate have an understanding around jerking off at night, but something new from his roommate's side of the room opens the door to sharing more. Later, Sam's careless mistake leads to an awkward situation for his roommate, and a new experience in the dorm room.

9.2 (42) 2169 21 Min Comments

Alpha's Dirty Secret (ch. 5)

By DanXWrites 22 Sep 2025

Good Boys Beg

9.6 (55) 7901 13 Min Comments

Washing Day

By Borehamwoodman 22 Sep 2025

It's washing day, and Steve and Tom discover they both appreciate classic white cotton briefs. Due to their age, they call them tighty whities, but while hanging them on the washing line, they discover that having a thing for classic briefs is just the start of a friendship.

9.5 (24) 1330 24 Min Comments