Gay Sissy Boy Stories

10,401 results
Orientation
Length
Source
Infinite Scroll

Working It Out - Bitch in Heat

by Baron_Cumhausen on Jan 29, 2019
Gay Male

Author's Note: Many thanks to your fellow readers' inspirational comments and up-votes, below is the second free-standing installment of the Working It Out series. I hope you enjoy reading it even half as much as I did writing it. ***** Normally, my morning commute is incredibly frustrating, what with all the traffic, texting drivers not aware of the gree...

The Nude on the Balcony

by KeithD on Jun 25, 2019
Gay Male

I knelt there on the artist's couch between Rafa's spread thighs, my hands gripping his knees—moving his knees out as I buried my cock in him and moving them together as I withdrew my cockhead almost to his opening, never, though, losing purchase inside him. The young Greek man, not more than nineteen by my reckoning and as handsome as Apollo, slitted his ey...

Roadside Assistance

by Robert_Furlong on Dec 23, 2019
Gay Male

Part of the 'Butt Monkey' series of stories by Robert Furlong === Driving over to Rugby for a meeting with a prospective customer, my car started spluttering on the A4304, and refused to respond when I tried to accelerate. Half a mile on, the engine was threatening to cut out altogether, so I pulled into the next lay-by, which was thankfully not too distan...

Dick - The Teen Gym Stud Ch. 08

by dominanceaddict1 on Dec 24, 2019
Gay Male

The pickup truck pulled to a stop. I was in the front seat of a Ryan's car, on my stomach laying across the wide bench front seat of the pickup truck. My ass was sticking in the air and the high schooler's strong hand was on it, squeezing. My head was in Ryan's lap, licking up and down on his massive, mostly-erect, teenage cock. At the moment, I was playi...

Playing Chicken

by BluePill on Apr 21, 2020
Gay Male

He wasn't sure why he did it, but somehow he just had to get the better of Darren, and if stuffing a fish full of sinkers to win a competition was going to get him there, well he was willing to take the risk. He just couldn't overlook the smug little comments anymore, the subtle little one-upmanship that Darren always seemed to carry on with. Sure he was g...

Office Party

by ThomasPenbrook on Jun 9, 2020
Gay Male

He was in a cocoon. A warm comfortable cocoon of early morning languidness. The type of morning where the sun was bright enough coming through the windows that it filled the room with a luminescent pale yellow but not so high in the sky that you couldn't block it out with a well angled pillow and the murmuring of "five more minutes". He had a companion in th...

The Beach Trip Ch. 03

by Elected on Sep 14, 2020
Gay Male

"Hurry up!" Emma urged me. Sunlight flickered through her tousled blonde hair and gleamed on the tan curves of her body as she backed along the beach. Her bare boobs jiggled as she moved, but her orange bikini bottom was still resolutely tied at her waist with its string in a careless loop. She had a towel under her arm like this was going to be a long excur...

Tied Up in Knotts Ch. 04

by Mrsgnomie on Oct 19, 2020
Gay Male

You're never too old to learn something. For example, I learned that, on Lee's scale of one—to the most important thing in the world—spending time with hot men trumped buying furniture for work. A mistake I will never make again. Me being tricked into attending Penn's birthday didn't go over well. Lee threw a fit the only way he knew how, dramatically with a...

Jacob's Little Sister Ch. 02

by EasyE42 on Sep 14, 2017
Gay Male

I started to panic realizing that I needed to get this cum off me and out of my outfit before my roommate came back from band practice. I crawl on my back to the side of the bed that was closest to my chest drawers. I open up the bottom drawer and got out an old t-shirt and started wiping the cum off my body and clothes. After a couple minutes I had most of...

Married Cocksuckers: The Gloryhole

by quutoo on Aug 29, 2017
Gay Male

I approached the video booth in the back hallway of the adult book store. I had about an hour leeway from the time that I got off work, till the time that Helen, got off at her job. I was eager that today's session would give me some nice cocks to get in my mouth. That's right. I am married, but I have been sucking cocks long before I met Helen. It started w...