Gay Chastity Progression Stories

435 results
Orientation
Length
Source
Infinite Scroll

Bathhouse Chastity Bitch

by Cumpup39 on Feb 11, 2019
Gay Male

I'm a married man in my early 40's, I'm 5' 7" in good shape and have a great wife and two kids. I also have a secret, I'm an absolute cum whore! I love everything about being used by men! I love being manhandled, degraded, covered in cum, piss and spit. My favorite kink is being sexually humiliated in public, in front of strangers. My wife would never beli...

Last Call Ch. 03

by sr71plt on Aug 18, 2017
Gay Male

I woke up in the middle of the night, aware that something had changed. We weren't moving, and there was no feeling of a motor grinding under us. I was locked in one of the smaller cabins belowdecks—not bound and not particularly uncomfortable, but my channel was sore. I would recover fast, but never in my life had I had such a ride as Fazil Fikret and his...

Chase Becomes Chaste Ch. 01

by growing_interest on Aug 22, 2017
Gay Male

Chapter 1 - A Good Deed Is Its Own Reward Disclaimer: This is fantasy. Chapter synopsis: Chase, a narcissistic cheater and sadistic rapist, has a life-changing run-in with a man who has a penchant for mind control, fitting punishments, and long-term chastity. A smartly-dressed, middle-aged woman walked into my office. She seemed familiar, although I did...

No Backup Plan Ch. 01: Sick Day

by klapperz on Aug 22, 2018
Gay Male

Max made a final fake cough as he phoned in sick for the day. It was never his plan to do this so soon after taking the job, but the excitement was too intense for him to wait any longer. Lying in bed, he felt his cock throb. But it wasn't time yet. Footsteps, loud bangs and chatter continued throughout the walls as his housemates rushed to get ready for wo...

A Progression of My Bisexuality...

by OceanviewFtLaud on Nov 6, 2018
Gay Male

After I was in Florida for a few years, I had been seeing a blond girl, and we got very close, and had a bad breakup. While I was seeing her, I had started to call this gay mens dating phone line, and even though I would make little notes about the ones I spoke to, I never met any. She was very attractive, little busty blond, but she said my dick was too big...

Finally Meeting Ch. 02

by BedtimeRoutine on Jun 5, 2018
Gay Male

The stranger was rubbing my ass. I could feel his hand clench tight when he grabbed a handful of my ass. I was completely naked in some random bathroom being fed my daddy's cock while a stranger neither one of us knew physically groped me and pawed at me like I was a piece of meat. "Fuck, where'd you find this kid?" The stranger asked. "Would you believe...

Blink: Five

by KenjiDeSade on Aug 18, 2017
Gay Male

The following story is a fictional account. The characters are entirely unreal and so are their situations. Thus no direct attention was paid to probability or safety for the characters. Such practices should not transfer over to real life situations. Practice safe, sane and consensual sex. For your own damn good. If you have problems or issues with queer po...

Blink: Four

by KenjiDeSade on Aug 18, 2017
Gay Male

The following story is a fictional account. The characters are entirely unreal and so are their situations. Thus no direct attention was paid to probability or safety for the characters. Such practices should not transfer over to real life situations. Practice safe, sane and consensual sex. For your own damn good. If you have problems or issues with queer po...

Keith Ch. 03

by LaLaLou on Sep 14, 2017
Gay Male

Keith whined, his body writhing on the table that he was strapped to. He subconsciously lifted his hips as something thin and sharp dragged tortuously across his prostate. "Say you want it," a voice, husky with lust and anticipation, snarled as Keith thrashed blindly. "I'm not going to beg for release from you," he growled, but it only made the voice laugh....

Plaything for Masseurs?

by SaminCali on Aug 18, 2017
Gay Male

Every incident related in this story is true -- only names have been changed. * The first time it happened, it seemed like a natural progression. I hired an erotic masseur to come to my home. He showed up, we went to one of the spare bedrooms, both of us undressed and I laid down on my stomach. The masseur bitched about the lack of a massage table, but he...