Gay Underwear Stories

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Infinite Scroll

Room Serviced Pt. 04

by bigblue212 on Jul 6, 2020
Gay Male

Carson's mind went blank. He was trapped. Mr. Armisen was toying with the underwear in his fingers, his other hand still holding the cigar. "I, uh-" Carson began. "What were you gonna do with this, huh?" Armisen asked, his thick eyebrow still cocked. Carson couldn't lie any longer. He didn't care. "I just wanted to smell it." Mr. Armisen nodded, the fain...

Tales of Dick Ch. 14

by Bjsroxxs on Jun 25, 2019
Gay Male

***Everyone in this story is fiction and are at least the age of 18*** Chapter 14: Jason: On Friday, Ares told me to meet him at his house for some studying. I wasn't sure if he was legit about studying or that he wanted me to suck his dick again. But I really didn't care if the latter happened. I was glad he was enjoying my dick sucking and was hoping th...

The Wet Dream

by dreamingofblowing on Sep 14, 2017
Gay Male

Part 1 I had never in my life had a wet dream before and so it came as a shock, albeit, a pleasant one when I awoke to find my underwear completely drenched in the sticky substance. My penis still very hard and covered in the moist liquid. "Wow, that must have been one hell of a dream" I thought. I remember the coach back in grade school giving a sex educ...

Best Friend's Brother Ch. 1

by Airagone on Aug 18, 2017
Gay Male

I used to spend a lot of time at my best friends house. Although there were 5 kids in the house with 2 bedrooms, 1 bath and a split dormer, I still found it a comfortable place to hang out. My friend was the second from the oldest, with sisters flanking him on each side, a younger brother and a very little sister. The sleeping arrangements were casual when I...

Hypothetical Hitch-Hiker Ch. 02

by Robert_Furlong on Aug 18, 2017
Gay Male

We both positioned our respective underwear in front of us - the outer and less intimate surface of the gussets facing towards us - and Dane lifted mine up to his nose first. I followed his lead, applying the outside of his shorts to my nose even though I would have strongly preferred to have done so with the inner lining, and we both took a few gentle sniff...

One Night in Dublin

by reverse69 on Jun 19, 2019
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** It was March of this year in Dublin Ireland, I decided to take an impromptu vacation to the island, but lacked the funds necessary for an adequate AirBNB, so I decided to try something I never did before... Stay in a hostel. I booked a male only room that housed up to 8 gu...

A Shift in Perspective

by CoburnAisling on Mar 18, 2020
Gay Male

Connor is talking about his model trains again. It's not that I dislike trains specifically; it's just... not exactly the most riveting of subjects. Especially when you really have to pee. The sun's been blazing all day, and without air conditioning, I've been drinking water to stay cool. Probably more water than was prudent, I think wryly. I can feel my bla...

Panty Lines

by naughtygaywriter on May 15, 2019
Gay Male

With my new job I had to move away from all my family and friends, almost a thousand miles away. It was an opportunity I just couldn't pass up, though it was taking me out of my comfort zone. I'm a bit of an introvert. I'm good if I know you or comfortable with you, but strangers I clammed up. Oddly enough, I'm in public relations. I moved into a nice one b...

Jay's Life Ch. 01

by CockE32 on Aug 18, 2017
Gay Male

AUTHOR'S NOTE: This story is planned as a long series and will contain many different topics. if you are uncomfortable with any type of story, then you may not want to start this story, or you may want to just skip those stories, though some may be mixed in. An example is that in this story there are elements of gay, hetero, and milf. Thanks for your interes...

Portly Cumming

by ChewToySub on Apr 24, 2018
Gay Male

I stood outside my arranged meet's front door, waiting for what seemed like a mini eternity before I heard the slow footsteps approaching from inside. I would later realise, with a clearer head, it was only a few seconds on that doorstep, but the butterflies fluttering in my stomach have the effect of stretching out time far beyond that of reality. "Hey son...