Gay Chastity Boy Stories

10,280 results
Orientation
Length
Source
Infinite Scroll

From Gay Husband to Slave Pt. 01

by assguzzler on Apr 3, 2019
Gay Male

My husband Winston and I were married when I was twenty two and he was thirty. I told him of my submissive fantasies and he role-played with me some at the beginning of our marriage but for the most part he showed little interest in D&S or Domination. We had a good marriage but we often fought as we both tried to dominate the other when it came to who would...

Guys' Retreat Pt. 01

by Cyanlot on Jan 20, 2020
Gay Male

Part 1: Going Away with the Guys "No!" Nicole was adamant. "You're not going, and that's final!" "But I have to," I said, trying not to sound like a whining teenager—or, worse, an impotent wimp. "We've been doing this every year since we were in college." "And what happened last year?! ..." She just let that hang in the air and I didn't really have a go...

Liam's Submission Tested Pt. 02

by PupTracer on Sep 14, 2020
Gay Male

"Shower," Marcus pointed to the corner of the blue tiled bathroom. "And face the wall, I love the look of your reddened ass." I complied, setting the water to cold, both to stop my cock from getting hard under Marcus' gaze and to soothe the burn in my ass. He left and then returned with my bag and instructed me to change into gear. "I'll be waiting for you i...

The Highland Festival - The Hotel

by BareBearsFan on May 15, 2019
Gay Male

Chapter 7 -- The Hotel ***Hello Readers Quick note, my stories tend to progress a bit slower, if you're looking for quick paced sex scenes try another story. Also some past people have nitpicked about small consistency details in my stories. I'm not writing a classic novel, I'm not going to take time to explain every little change in a scene. If you're...

Gay Lovin' Gone Bad

by Ciceri on Aug 18, 2017
Gay Male

I have always been turned on by the lash or whip. Even when I was a teenager I wasn't so repelled by the idea of slavery merely because the whip was often used. Of course, slavery is bad. I knew there was an occasions when two or more consenting adults got together and used a whip. I just did not know when. I grew older and became aware of such occasions thr...

On No He Didn't

by felicia_rene on Sep 21, 2020
Gay Male

Description This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy safely. Rick a tall well-built handsome entertainer catches the eye of his boss as he works at his night club. The man's lust consumes him and he conspires to twist him and make Rick his bottom. Despite the fact that Rick insists that he was a...

Naked Scott Ch. 05

by tattoo_dragon on May 12, 2020
Gay Male

Writer's note: this scenario contains extreme dominance and submission as well as master/slave role play. Just a heads up in case that is not your cup of tea. *** At eleven o'clock on Friday night, there was a knock at my door. My body jumped to attention. My cock started getting hard as I went to let him in. My hand was trembling slightly as I raised it...

Progression Ch. 14: Befriended

by klapperz on Jul 3, 2018
Gay Male

Nathan woke up earlier than usual the next morning after a night of arousing dreams. He was eager to start work and see what the guys had in store for him. After his daily inspection with Kevin, they both made their way to Ryan and Jacks house. Once they arrived, Nathan stripped and made his way to the basement to begin his daily show. When he reached the...

The Making of a Master

by Littlepoppyhole on Oct 6, 2020
Gay Male

David lay on the dishevelled bed exhausted and still sweating after his recent sexual encounter with a man called Raymond. His hole was leaking semen onto the bed sheets. The sheets also gave off the aroma of anal mucus. This did not perturb David as he was deep in thought about the man he had served. He thought there was room for improvement in his sexual i...

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...