Gay Pillow Humping Stories

4,539 results
Orientation
Length
Source
Infinite Scroll

I Lost it at Fire Island

by CrimsonClown on Aug 18, 2017
Gay Male

My brother Max and I grew up in one of the most liberal places on Earth: New York City. We're those typical New York guys who loved to go to the ball games and enjoyed hanging out riding the train anywhere in to the city that we wanted. We spent most of our lives chasing after women, which was especially shocking when he came out of the closet a year ago. It...

Bad Luck for Me

by Triplebottom on Aug 18, 2017
Gay Male

I wasn't very happy. My boss made me take a vacation because I hadn't taken one in years. Ever since I divorced my wife, I simply drowned myself with work. I didn't want to date or even look at another woman. I was just so damn heart broken. Heather was perfect to me. I guess she didn't feel that way about me since she had an affair with her old crush from h...

Boxer Briefs Left Behind

by BeltBuckle on Mar 11, 2019
Gay Male

I carefully stretched my arm muscles while flexing my entire body before the mirror and check myself out for a while. I could easily afford to do that - at this time, the gym locker room was deserted. Very few people came here this late at night, and that's what I liked. Privacy. It was almost absolute - I saw nobody else in the gym at this time and there wa...

Slut Scout

by Michele G on Sep 14, 2017
Gay Male

Our neighbors have a really good-looking son," Chad. His room is up in the attic of their house like mine is. Every now and then I see him in his window and he's seen me from his. He knows all about me and is cool about my cross-dressing. I see him with a lot of pretty girls. Sometimes I catch him sneaking them up to his room. The girls can get pretty loud a...

Efrain and Cory Ch. 29

by dayne on Sep 25, 2017
Gay Male

Aaaaaaaaaaand now the penultimate chapter! Epilogue to follow soon...erm...eventually. One would think quitting your job would allow for more writing. Chapter 29 - In Which We Have Breeders for Dinner The curving lines of Preston's back emerged as he propped himself up on his elbows and the sheets slid down to his hips. "So, you only get a few days aft...

Brotherly Discovery

by snerpyloo on Aug 18, 2017
Gay Male

Michael finished his homework and was ready to relax for the night. John, his 27-year-old brother came over, to mooch dinner off their parents again. Michael didn't mind. He enjoyed having his big bro around and he wanted to ask him a few questions anyway. Questions he didn't think he'd be able to ask anyone else in the world. "Hey John, wanna come up and s...

Hoffner and his Elf

by BigWig69 on Aug 18, 2017
Gay Male

I was lying in bed next to Hoffner. He had just finished making sweet love to me and I was lying on his silver haired chest, slowly and softly, licking his soft pink nipples. Our legs were entwined, his large, powerful hand, caressing and squeezing my balls. We had been seeing a lot more of each other, meeting in hotels or at his place when his wife was out...

Graham and Griffin Ch. 05

by emilyandalucia on Aug 18, 2017
Gay Male

Griffin's POV I wake up before my alarm goes off. The events of last night come rushing back. My mind first goes to Graham's warm kisses and touches, his arms around me. He was so kind and understanding when I told him about Ryan and my fear of disappointing my parents. I then made a mess of everything by asking about Jeremy. My worse fear had come to light...

The Bear

by BigWig69 on Aug 18, 2017
Gay Male

I could hardly breath, his thick forearm, pressing hard on the back of my neck, driving my face into the sanitized cotton pillow at the hotel room near the airport. An inconspicuous place full of the unfaithful searching for anonymity, lust and release from the humdrum of their lives. Looking for the gratitude and love that was in short supply in a world too...

Dom Bottom Ch. 02

by naughtygaywriter on Jun 5, 2019
Gay Male

It's Saturday and I don't feel like being bothered. My not so little twenty something keeps texting me. He wants to see me again tonight. I haven't decided if I'm in the mood yet. I can't let these tops have what they want when they want it. I give him coy, I'll think about it responses. When I'm in the gym he sends me a pic of his hard dick. My hole twitche...