Gay Underwear Stories

6,363 results
Orientation
Length
Source
Infinite Scroll

My Friend's Boyfriend

by whoneedsguys on Sep 14, 2017
Gay Male

This is my first ever submission so ~ * This was the first time I'd ever met my friend's boyfriend. I live with three other girls (Jess, Ella and Charlotte) and another guy, but he was away for the weekend. We were all sat downstairs, drinking, getting high, it was me, the three girls and Charlotte's boyfriend, James. I was already attracted to him, he h...

Confronted with Homophobia Pt. 04

by koksocker333 on Jul 27, 2020
Gay Male

"Tom your making me crazy, my cock is ready to blow a load and you have not even removed my pants. If I had known sex with a man was this good I may have tried it many years ago." Robert told me. "Robert so I really am your first man?" I asked him. "Tom of course, I was so deep in the closet before all this do you really think I could even get undressed in...

Used For a Week Pt. 03

by mralx99 on Aug 22, 2018
Gay Male

"More Firsts" - Wednesday & Thursday Part 1: https://www.literotica.com/s/used-for-a-week-pt-01 Part 2: https://www.literotica.com/s/used-for-a-week-pt-02 So many questions: Had I really changed so much in just three nights? How had William - my old school friend, now in his fifties - gotten me to suck his cock, wear women's underwear, and be ass-fucked...

The Hood Pt. 02

by Bjsroxxs on Sep 12, 2018
Gay Male

There were two small presses on my stomach, moving side to side but in the same area. It felt good actually. Honestly, I wasn't entirely sure what it was until I heard the noise. The light continuous vrooms made me realize what it was, a cat. I opened my eyes and lifted my head to look down to see its emerald colored eyes staring back at me. Slowly, I lifte...

Daddy's Little Nurse

by ElioV on Jul 31, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** "Come on dad... just a few more steps. Let's get you in bed." My son said to me as he led me to my bed. I had fallen off a ladder just hours earlier and fractured my left arm and spraining the right one. I also twisted my left ankle pretty badly. I will be on bed rest for a few da...

My New Life Pt. 02

by koksocker333 on Oct 8, 2019
Gay Male

It had been a rough week, break downs at work, overtime almost every night, my ex out of the blue calls me she and her new guy have split up and she wants me back. "Not for all the money in the world would I go thru that again." I told her point blank. In a way I felt like maybe I should have tried to get back with her see if I could make it work. "You...

Tales of Dick Ch. 08

by Bjsroxxs on Oct 12, 2017
Gay Male

***Everyone in this story is fiction and is at least 18 years old or older*** ***** Chapter 8: Fast Loads at LA High Jason and I spent the rest of the weekend watching movies. On Monday, he went to school and I went back to work. As I walked to work I thought about our experience at the pool, wondering if I would see Kyle again. Jason: I left Dick's hou...

Planting The Family Seed Ch. 03

by arthurwilliamdent on Sep 14, 2017
Gay Male

Author's Note (C-Sharp) This chapter is back to the incest theme at the beginning but finishes with another encounter between Denny and John. Is John secretly aware of these encounters or do you believe that he can sleep through two orgasms? I will be developing that relation more in future chapters. Chapter 4 will delve into Denny's father's history and w...

Father In Law Confidential

by jordongeff on Sep 14, 2017
Gay Male

The Trip Begins When my wife and I moved back to Denver from Las Vegas, her mom and dad flew down to help us with the move. After a few days of packing, the moving van arrived and we basically got out of the way while the company loaded up the truck. While the movers were busy doing their thing, Edward and I dropped the girls off at the McCarran airport for...

Campout Peeping Ch. 01-02

by jjdtx on Sep 19, 2017
Gay Male

Chapter 1: The First Jerk Off Scott and I had been best of friends since we were kids. We lived across a large lake from each other and spent most all of our time together. We went to the same school, looked the same with brown hair, brown eyes, both tall and skinny, most people thought of us as brothers. Now, at age 18, sex was our main topic of conversati...