Gay Dirty Underwear Stories

9,633 results
Orientation
Length
Source
Infinite Scroll

Photo Fuck

by buttcheeks777 on Sep 15, 2017
Gay Male

As an architectural photographer I often find myself in empty, new buildings all by myself. Right before a project opens is typically when I'm hired to photograph the space; when everything is all set up but tenants haven't moved in yet. I've been photographing a lot of assisted living facilities the last few years for a great client. These buildings have be...

First Gay Daddy Pt. 01

by freddyjones86 on Sep 16, 2017
Gay Male

Ever since I could remember I've had this dirty little thought about older 'daddy-types' teaching a younger twink how to suck dick and take a good fucking. This real life story is about the first time I ever sucked a daddy dick... Well, for starters, I am in my late twenties but can pass for about 21-22 if I shave and wear the right type of clothing. I've...

Fantasy Finally Fulfilled

by bmxcali88 on Aug 18, 2017
Gay Male

Hey, I'm straight and have a gorgeous girlfriend. We're both 19 and go to school at an awesome university. We get horny all the time it seems like, but occasionally when I get horny I have this crazy fantasy of having sex with another guy. I told my girlfriend about this and she thinks it's really hot and it's now her fantasy to have a threesome with me and...

My Misspent College Days!!

by t2u1ck on Oct 6, 2020
Gay Male

Another entirely fictional story. I hope you enjoy I was at university when I first started giving blow jobs. It just sort of happened. I'd better tell you the whole story. I was always good at most sports and particularly cricket. I had played for the school team and when I got to uni I was soon involved with my college team. At the time it was mainly mad...

On My Knees for My BF's Straight Flat Mate

by Graysmirks on Jul 31, 2018
Gay Male

It's was Monday and Sting woke up early to go to work. In the apartment it was just me (Natsu) and Pablo, Sting's flat mate and lifelong friend. I laid naked on the bed, lazy and horny. I wondered what was Pablo doing. Yesterday evening he came back from a weekend out rock climbing, we heard him from Sting's room. As usual he dumped his stuff in the entranc...

Privilege

by IAmThePuppetMaster on Sep 14, 2017
Gay Male

It was shaping up to be a stressful day for Paul. The eighteen year old had spent the morning on his family's private golf course and most of the afternoon getting acquainted with his new private masseur only to enter the west kitchen for a snack and be blatantly disrespected by Alphonse, the uncouth new pool cleaner, causing him a level of stress he was not...

Wanted: JO Buddy

by jon227 on Aug 18, 2017
Gay Male

Note: This story explores a bisexual/bi-curious relationship where two friends explore the boundaries of their sexuality. * "Here goes nothing," I thought as I clicked submit. I had finally mustered the courage to post an advertisement. For quite a while I had kept my online habits a dirty, little secret. I'd go on chat sites and swap porn links with othe...

The Meat of Our Relations

by farless on Aug 17, 2017
Gay Male

I have a birthmark on my ass which my boyfriend liked to comment on frequently, and sometimes in public places. Matt, my boyfriend, also liked to wrap his arm around my slim waist and hip check me up in the air. I think he did it just to remind me that I was smaller than him. Other than that, it's what I expected from a college relationship. That is to say,...

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...

A Friend Made Me His Bitch

by Singleman96 on Sep 14, 2017
Gay Male

I was browsing MyBook, admiring my best friends sister Alison like usual. She was going to a community college nearby and was looking fantastic. Her brother, my best friend, was good looking too. A six pack, blonde hair. I wasn't gay but I did admire a good body when I saw it. He lived a close walk away so I usually visited them when I could "Speak of the d...