Gay Underwear Stories

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Hot, Straight Step Brother Moves In Pt. 02

by Gayguilt on Sep 14, 2020
Gay Male

Neil didn't know what to do or what to say. What could he possibly say to get out of it? There was Liam stood at the foot of the bed, wearing nothing but those green boxer briefs he was tormenting Neil with during their movie, and Neil in bed with one hand on his rock solid cock, and another hand holding Liam's used, sweaty white CK briefs. Time seemed to go...

Hot, Straight Step Brother Moves In

by Gayguilt on Jul 27, 2020
Gay Male

At the age of 18, Neil had gotten used to being an only child. He liked it that way. He never had to share his parents attention with anyone and quite often he got his own way. That was until his parents separated, and a year after the divorce, his mum had met someone new. Neil didn't care too much. He came out as gay three years back, and he was enjoying li...

The Hermit

by canaigle on Sep 4, 2017
Gay Male

Chapter One Ted was really excited about his plans to go hiking on his own up north in the wilderness. He was out of work and needed to get out of the city in order to take time to think about what he wanted to do. At 30 years of age he was in one of those in between spaces somewhat lost and not knowing what he wanted out of life. Ted stood about 5 feet 7 i...

Online Briefing

by Robert_Furlong on Aug 18, 2017
Gay Male

Part of the 'Butt Monkey' series of stories by Robert Furlong === I scrolled down the pictures of men's underwear filling the screen, trying to locate the Calvin Klein boxer briefs Jake prefers. If I bought him the wrong ones, he'd wear them once and then that would be it. He'd say they were uncomfortable or they chaffed at his thighs or they rode up into...

The Pool Locker Room

by gaius89 on Oct 24, 2018
Gay Male

(This story is partially true. Name and places changed. The main character is me) *** My name is Alessio and I am 27 years old, I am blond with blue eyes, 180 cm tall and I swam from 6 yo to about 23yo. I was part of a small agonistic team in the province of Bologna made up of about ten boys. At the time I had a girlfriend and I have always been quite popu...

Uncle Will

by canaigle on Feb 13, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** Uncle Will Chapter One I had just turned 19 when it was decided it would be better for me to go stay with my uncle Will. Mother was expecting at this late period in her life, she was in the hospital due to serious complications concerning the baby's delivery, life threatening...

Underwear Friends Ch. 05

by ramon25 on Sep 16, 2017
Gay Male

During the middle of summer, while my little brother was away at camp and my dad was on a business trip, my mother and I had connected during a period of mutual loneliness. My dad had been having an affair, and my best friend and lover, Mark, had moved back to Texas. My mother and I had a drunken night of sex, that led to a few more exploratory sessions, bef...

Colorado Rocky Mountain Bi Ch. 03

by walterio on Apr 17, 2019
Gay Male

AUTHOR'S NOTE: This chapter contains bisexual encounters with a bi-guy and gay guy. It also contains straight sex. BACK TO GORDY On Monday morning, I left Sandy and Gordy sleeping in bed when I went to work. Sandy was flying back to Denver later that day and Gordy would prepare for his interviews that week. I got home from work around 6:00 PM and joined G...

Denial and Acceptance

by onejustforfun on Sep 14, 2017
Gay Male

I was 18, and my friend of several years (Jeff) was had turned 18 just a few days before. We played on the same baseball team, and every year for last few we had at least a couple of classes together. So we were pretty close. We were both in good shape, but Jeff always had that certain something. He was about 5' 10" and had kind of round face that made dimpl...

Alcohol as a Crutch

by timmywells on Aug 17, 2017
Gay Male

Paul had made it to the bed, but not into it. Instead, most of his slender 6' frame was sprawled across it, with his legs hanging over the side as he lay face first on the bedding. His tangled underwear were down to his knees and the only clothing left on him were his white athletic socks. We had been drinking, like we did every Saturday night, and just lik...