Gay Underwear Stories

6,363 results
Orientation
Length
Source
Infinite Scroll

Kyle

by kgilbraltar on Aug 18, 2017
Gay Male

It was a hot June night in our little town in Kentucky. My best friend Kyle and I were planning on hanging out at my house. My mom, who never really grew up, surprised us by buying a bunch of booze and intended to share it with us. My mom was a still somewhat attractive woman. At 41, she still somewhat maintained her body but her years of partying and exce...

Alone No More

by DWSimon on Sep 25, 2017
Gay Male

I was staring out at the wide expanse of the Cascade Mountains as I piloted over them. I worked for one of the airlines, based in Seattle. I usually flew small, 70-seat commuter aircraft, but was certified to fly all the way up to a 737. I had spent almost every waking moment from the time I was 12 learning how to fly. I loved the freedom and thrill of soari...

Higher Education Ch. 05-06

by MelvinMhk on Aug 17, 2017
Gay Male

Chapter Five : Preparing for Tina's Visit It was now Tuesday morning and I found myself sitting at my desk. I couldn't believe I had done everything I had done with Jake in one night. What was happening to me? Had I been suppressing these things for a while or was it just that I was excited about being away from home and feeling free to experiment with the...

Are You Game? Ch. 02

by 2ndAlias on Sep 14, 2017
Gay Male

Divisional Playoffs ---Saturday On the way to Ben's place that afternoon, I ran into Erik in the hallway and we took a few minutes to catch up before going inside. Erik's cousin is married to a friend of Joe's and the two of them struck up a friendship through that connection. I had first met Erik, along with his wife, Janelle, at the same holiday party...

Paramedic Pt. 03

by Snowblind94 on Sep 25, 2017
Gay Male

I appreciate all the comments you guys have made. It is easy for someone to give advice of my finding an editor or proof-reader, but hard for me to do it. I don't know anyone who would do it and I have been in contact with a couple of people, but never heard back from them. I tried real hard to find all the mistakes in this chapter. I am not a professional w...

I'll Fuck His Hot Dad: Turning

by whitechocolate3 on Sep 14, 2020
Gay Male

All characters are older than 18. ***** Frank. I was 20, and he, 20 years older. At first he only seemed like the usual strict dad, who hated me for influencing his son to the wicked ways. I wasn't that bad, but he saw something in me. Something invasive. I didn't have much choice where hot dads were concerned. The hotter the dad, the most intrusive my e...

A Day to Catch the Son-In-Law

by whitechocolate3 on Oct 6, 2020
Gay Male

(Characters are older than 18 years) (Warning: this is not part of a series, and lots of cheating involved) - Enric never knew for sure about Armanno, he only suspected - and hoped - very strongly that his son-in-law hid a forbidden interest deep inside. Now Armanno had returned, and they were going to spend a whole day together. Fate had given Enric a...

My BIG Sexual Awakening Ch. 03

by Andrsn on Jun 8, 2020
Gay Male

When I wake up I don't feel hungover but Dan is still in bed, presumably asleep. I'm not hard this morning when I wake up, in fact, I don't know if I can make myself hard because I can barely even pee. It is only when I am midway through my shower that I realise I am still drunk. I go back to our room and change in front of Dan who seems to be waking up. For...

Apt. B-5

by Apolo1 on Aug 18, 2017
Gay Male

My friend Marcus and I entered the building and caught the elevator to the basement floor, and when the doors opened we looked at each other warily. The hallway was extremely dim from what we could see, and for a moment I considered letting him go in by himself. "Are you sure this is the right place?" I asked. "Of course. 69 Appleton Street. Apartment B-5,...

Construction Boss

by Thormand1963 on Jun 8, 2020
Gay Male

One evening as I was driving home from work I encountered a traffic jam due to a multiple car pileup. I didn't want to sit idly in traffic so I turned off into a residential area figuring I could find my way home. It might have taken longer than waiting in the traffic, but at least I would be moving. Winding through the residential streets I saw a new house...