Gay Shemale Chastity Stories

340 results
Orientation
Length
Source
Infinite Scroll

Chase's Dive into Chastity Ch. 01

by Ohshidwhatup on May 15, 2019
Gay Male

I awoke to the harsh wailing of my morning alarm. With groggy annoyance I rolled over and switched it off. I had the urge to just cover my head with my pillow and go back to sleep but something kept nagging at the back of my mind as i lay there eyes closed. Whatever. Just ten more minutes. Have you ever had that feeling of worry even when you are asleep? T...

Trained as a Urinal

by Cumpup39 on Feb 11, 2019
Gay Male

Sir is a beautiful man! He is in his mid 40's, 6' tall and has a beautiful hard body. His short dark hair and blue eyes make me weak. He has a perfect cock, just under 7" but thick and I can't keep my mouth off of it! I was his regular cocksucker for a while, coming over whenever he needed to get off. Sir works hard and doesn't have time to date, so I got a...

When Chastity Goes "Wrong"

by whiteboibbclicker on Aug 18, 2017
Gay Male

Editor's Note: story contains nonconsentual themes. * Let me introduce myself, my name is Alex, I am a 21 year old skinny white boy with a high school degree still living with my parents at home. I work at the local grocery store. The reason for my failure in life is my uncontrollable addiction to porn and masturbation. Every time I finish my work I quickl...

Progression Ch. 12: Duties

by klapperz on Jun 18, 2018
Gay Male

The next morning Nathan slept in, glad he didn't have to get up for work as usual. He lay in bed, wondering what he would do during the day. He thought about the tasks Kevin might make him perform, and if he would get to taste his cum again. At 9.15am Kevin entered the bedroom, saying "Excuse me? Is there any reason you are late?" "Late? Kevin, I got fired...

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...

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...

Progression Ch. 10: Prison

by klapperz on May 1, 2018
Gay Male

Nathan looked around the room for something to do, but it was empty. There was only the bed, which was just a mattress laid out on the floor and a door leading to the toilet. The was a dim light that allowed him to see, but no windows or view from the door as he was in the basement after all. He thought about what he could do to entertain himself, and quick...

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...