Gay Underwear Stories

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Infinite Scroll

Yes Sir Ch. 02

by boxerj on Nov 21, 2017
Gay Male

It had been nearly a week since my last meeting with my teacher, Mr Davis. And when I say meeting I mean when I walked into his office, was blackmailed into pulling down my trousers and underwear, bending over a table and letting him masturbate and cum all over my ass. You know, the usual. My experience with Mr Davis had opened my eyes to my sexual desires....

Tales of Dick Ch. 02: Pleasure Points

by Bjsroxxs on Sep 1, 2017
Gay Male

***Everyone in this story is fiction and is at least 18 years old or older*** ***** My name is Richard, I'm 23 years old. I own and work at the local skate shop in my Los Angeles neighborhood. I am opening bisexual and currently single. I've had a few sexual adventures with the most random of people. It was 2 pm in the afternoon when Dylan finally showed...

Liam Ch. 01

by Lucas96 on Sep 14, 2017
Gay Male

Disclaimer: this story involves cuckolding/cheating. ***** Kyle and I were dating for almost a year now. We met early in our sophomore year in college, and when we entered our junior year together, we decided to rent an apartment together and see how things went. So far, it was going great. We had a lot in common - we were the same age (21), we both liked...

The Shoplifter

by asdvPenguine on Oct 5, 2020
Gay Male

It had been almost two months since I moved here to start university. So far I hadn't had much luck finding new friends and yet again I found myself strolling down-town to pass the time. Once I reached the end of the shopping street, I continued into the huge upscale department store towering over the city centre. I took the escalators up to the menswear de...

College Men's Room Ch. 2

by scentto on Aug 31, 2017
Gay Male

After discovery that upstairs restroom in the student union, I found another smaller restroom in the basement which turned out to be another good spot to look for some action. It had four stalls and two urinals. One morning, I decided to take advantage of the peep holes and see where it would lead. This particular men's room was rarely used, and therefore af...

Session With My Therapist

by Proud2bGAY on Sep 14, 2017
Gay Male

My name is Cole ever so recently I ran away from home and moved in with my friend Jacob. I'm 18 and have short dirty blond hair, green eyes, 5'8", with a cock that is close to 7 and a 1/2 inches long and, I have a six pack. My sexual orientation well lets just say I thought I was straight. So, I ran away from home because I just couldn't take living there a...

Adventures with Kevin

by houston_man_28 on Aug 18, 2017
Gay Male

Let me begin by telling you a little bit about myself. I would define my sexual orientation as "bisexual" (sort of). I love sex with women. When it comes to men, I am only really sexually attracted to them for the thought of being submissive to a dominant guy. I have no desire to put my dick in another guys ass, but I LOVE sucking cock and getting fucked in...

A Year with Jonah Pt. 02

by Thenewboy0 on Aug 18, 2017
Gay Male

JANUARY 20th 'You fucked him!? You fucked him and then left him outside! He don't know this city! And my brother? My fucking brother, Sean? How the fuck is that fair!?' This week's episode of 'Buns' was very good. Ali's brother had come to visit for the week, and Greg had acted like Greg always does, and seduced Ali's brother. I wish I could be more like G...

My Journey As A Slut Continues

by calneslut on Sep 14, 2017
Gay Male

Those of you who read my account of my first taste of gay sex will may remember that I had something of a baptism of fire – tied up, dressed in my girlfriend's sister's underwear in a local field, where I was forced to deepthroat a stranger before swallowing first his cum, then mine and finally some of his piss. Well, that remains my best ever sexual experi...

Hard Time in Prison Pt. 01

by harryhotdog on Sep 14, 2017
Gay Male

The guard roughly released his arm and pushed him into the cell. The big metal door slid shut behind him and locked into place with a heavy thud. Brad had never been to prison before and this was the first moment that he wasn't being prodded/grabbed/pushed around by the guards through the various processes new inmates go through. Now he was finally by himsel...