Gay Boxer Stories

2,083 results
Orientation
Length
Source
Infinite Scroll

David

by bimanms on Aug 18, 2017
Gay Male

I couldn't believe my luck, I created my account on squirt and the very next day I received an e-mail from a guy not far from here. He expressed interest in meeting me but told me he was inexperienced. I wasn't sure what he wanted to do. In the e-mail he told me a little bit about himself. He said he was in his late twenties about 5 foot 9 inches and 200 pou...

The Boifriend Ch. 02

by AdmiralSquish on Jun 19, 2019
Gay Male

[pre-story]This story's not dead! I was a little stuck trying to figure out what to work on, and I got some comments recently asking for more M/M stuff, and then I got inspired and now here we are. Convenient that the first story to go public in pride month is M/M. Content Warnings: M/M, femboy, sissy, potentially offensive dirty talk Disclaimer: All chara...

Uncle Jim

by Thormand1963 on Apr 28, 2020
Gay Male

The year after high school, I was still living in the small town where I grew up. I was working in a factory to earn money to start a college education. My mother was diagnosed with terminal cancer and most of our funds and time were spent making sure her last few months were bearable. I was looking forward to getting out of our small town and starting my li...

Fagboy Finds His Alpha Straight Man Ch. 03

by motoskoota on Dec 2, 2019
Gay Male

As the months passed, I was summoned to Donnie's house two or three times a week. I was extremely pleased that he, apparently, liked the way I serviced him, but I took nothing for granted. He had my phone number and when he called, I'd better be ready to drop everything and come to him. Sometimes, I would be woken from sleep in the wee hours, have to dress i...

Underwear Friends Ch. 05

by ramon25 on Sep 16, 2017
Gay Male

During the middle of summer, while my little brother was away at camp and my dad was on a business trip, my mother and I had connected during a period of mutual loneliness. My dad had been having an affair, and my best friend and lover, Mark, had moved back to Texas. My mother and I had a drunken night of sex, that led to a few more exploratory sessions, bef...

Miles's Revealing Clothing Teases Pt. 02

by sweetcobs84 on Mar 3, 2020
Gay Male

As we exited the staircase and entered the cafeteria, there was a collective gasp from a number of the senior class whose table had them facing our direction. Miles was a few steps in front of me. "What are you doing?" asked Ryan. "I was arrested," replied Miles. Recognizing the confused look on a number of the seniors' faces, I explained, "We were in Mr....

Getting Off with Jose

by AnthonyAtwater on Aug 18, 2017
Gay Male

I had my first and only homosexual experience when I was 18. I drove a buddy of mine home from a house party we were at and when we pulled up to his house, he invited me in for more beer. He always had alcohol in his house because his stepdad drank so of course I said yes. His room was at the back of the house so we had to be quiet so we wouldn't wake up his...

Roommate Ch. 02

by biaznboy on Sep 1, 2017
Gay Male

We kissed deeply, hungrily, tongues playing wetly against each other as our hands roamed freely over each other's bodies. With his thigh trapped between mine, I was pretty sure he could feel how hard I was through my thin -- and by this time -- wet boxer shorts, thoroughly soaked with the beads of my own pre-cum. And I could feel how big he was. He was respe...

My New Business

by Westless99 on Aug 18, 2017
Gay Male

I am 60 years old. I had just retired and was looking forward to enjoying my retirement with my wife. We were virgins when we married and though I had quite a fantasy life, we only had sex with each other. Our sex life, though difficult at times due to her night-shift job, was generally fulfilling. She was a little on the chunky side, as was I, but enjoyed s...

Special Procedure

by KenJames on Oct 15, 2017
Gay Male

Steve pulled into the medical center parking lot at 5:45 p.m. Dr. Harry Wu's practice closed at 5:30 p.m. and the door was locked. Dr. Wu was sitting behind the reception desk. He let Steve in, then relocked the door. "Thanks for seeing me, Doctor," Steve said. "I just couldn't get away sooner." "No problem." Dr. Wu was a big handsome Asian man in his ear...