Gay Shemale Chastity Stories

340 results
Orientation
Length
Source
Infinite Scroll

Seduced by a Billionaire

by ret123 on Sep 14, 2017
Gay Male

I could not believe it. The woman behind the front desk told me again, "We are sorry sir, but we have no reservation for you and the hotel is completely booked for the whole week because of the meetings and retreat for a major financial institution." "I know!" I said. "I am supposed to attend those meetings and participate in the retreat! Please, help me ou...

Temporarily Dickless

by AssWhisperer on Sep 14, 2017
Gay Male

[Warning: This is a very sexually dark story. Fisting, watersports, medplay, implied body modification, chastity. My thanks to Kenji De Sade for his encouraging me to write this story after a series of conversations about chastity.] How had I come to be here? I wondered as I floated in orgasmic bliss. It had started with my impulsively writing a guy on...

The New Slave Ch. 07

by martin_x59 on Sep 14, 2017
Gay Male

I would like to thank all your positive comments. I'm really glad you are enjoying this series. I have just written a new short story that I think you may all like, please keep checking back. I intend to post it next week. In the meantime here are some instalments in Daniels journey into being a slave. *** College is slow today, I'm finding it difficult t...

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...

Progression Ch. 09: Punishment

by klapperz on May 1, 2018
Gay Male

Once again Nathan found himself lying awake beside Kevin, who was sound asleep. All that was running through Nathan's mind was having Kevin's cock thrust into his ass. Unable to sleep, Nathan sat up and turned on his laptop to watch some porn. He logged into Ryan and Jacks porn channel and watched the videos. Each one made his cock fill the cage more each t...

Top Becomes a Daddy Bear's Boy Pt. 02

by DaddyBearChaser on Jul 6, 2020
Gay Male

Mike woke up in the morning and gave his new boy a tight squeeze, nuzzling his beard and nose into his boy's smooth neck. "Boy it's morning, time for you to get up and take care of my needs," he said softly in his deep grizzly voice. I woke up being squeezed and spoken to, not knowing what was going on I tried to get up. I felt big arms wrapped around me an...

Chastity Release

by AmethystMare on Nov 24, 2017
Gay Male

This is a short work of erotic fiction containing furry, or anthropomorphic, characters, which are animals that either demonstrate human intelligence or walk on two legs, for the purposes of these tales. It is a thriving and growing fandom in which creators are prevalent in art and writing especially. ***** The Twelve Kinks of Christmas Chastity Xander b...

The Visitor Ch. 03

by Leanne_sissy on Sep 26, 2017
Gay Male

This is the third part of my little story and again I must tell you that as with all my work it is based on actual experience. The feelings I try to give are the feelings I felt, I write it from my perspective as me, Leanne. Some people have written some nasty comments to my previous parts, but hey ho, I have also had some lovely support. I have now changed...

A Chastity Story Pt. 01

by Fromthetap on Oct 15, 2017
Gay Male

I arrived at the street and pulled up just after the entrance to the cul-de-sac he lived on. Getting out of the car, I pulled the zip on my jacket up to the top to hide the collar I was wearing. It was 2:30am but even so a car drove past as I walked down the street, pretending to cough so that I could cover my neck with my arm, not wanting the headlights to...

Confessions of a Chastity Slave

by deviator on Aug 31, 2017
Gay Male

It's hard to believe it all started with some talk on a chat room. I was in college then, and always straight in real life, although not very successful with the ladies. But my dirty little secret was that I liked to go online and indulge my fantasy: being enslaved, feminized, and kept in chastity by a man. At first, I'd wander through chat rooms and find a...