Gay Chastity Cage School Stories

8,155 results
Orientation
Length
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Infinite Scroll

Nephew's Readjustment Pt. 06

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments, ideas and feedback are welcomed and sought after! ***** Cynthia spent the first few days of the week getting Nicholas accustomed to anal o...

Chase Becomes Chaste Ch. 02

by growing_interest on Aug 22, 2017
Gay Male

Chapter synopsis: While Chase loses his property and his dignity, our narrator takes possession of his new condo and his new boy. *********** The movers arrived bright and early. I had just awoken from a pleasant sleep, dreaming all night of how I could punish Chase next. I felt refreshed and empowered once more. It was that same sense of certainty that ga...

The Pictures Ch. 05

by Mike Cindy on Aug 17, 2017
Gay Male

I woke the next morning and checked the house before leaving for work. I made sure everything was in its place. I hoped my wife would be home tonight and I didn’t want any problems. Jack called me about 10:30 and said, “you’ve got e mail”, and hung up. I opened the mail and saw 2 pictures of me dressed in female clothes; the poses Jack had put me in last n...

Caught in the Act

by litgal on Aug 18, 2017
Gay Male

Jeremy stood in the middle of the living room, his stomach tightening in fear until he thought he just might have to make a run for the bathroom. "Ry, man, I'm really sorry. You were drunk, I was drunk, let's just let this one go," Jeremy practically begged as he turned away from the damning evidence on the computer screen. Even on the small screen he coul...

Guys' Retreat Pt. 03

by Cyanlot on Jan 20, 2020
Gay Male

Part 3: Serving I don't know when Vince came into the bedroom. Amazingly, I got to sleep quickly and slept soundly until about 7:00, when light came streaming into the room. I looked over and saw that Vince was still asleep in his bed. I didn't want that to change so I very quietly got my clothes together and tiptoed to the bathroom for a shower. A long ho...

Outed and Married

by keptsissy on Sep 26, 2017
Gay Male

He always threatened me with being exposed to my coworkers, to the world as the sissy I am to him. Usually it was part of what I thought was his dirty talk, sex talk. He'd tease me with it. He'd be deep inside of me, slow fucking me, talking dirty into my ear. Or he'd have me restrained and be masturbating me as part of 'my reward', as he called it, and woul...

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...

Chase Becomes Chaste Ch. 03

by growing_interest on Aug 22, 2017
Gay Male

Chapter synopsis: Our narrator expands Chase's hell beyond his home, Chase's new wardrobe beyond the one jockstrap, and Chase's virgin asshole beyond its normal size. ********* "I'm not going out like this!" How long was it going to take Chase to figure out that he didn't have a choice? I wasn't "asking" him to do anything. I was telling him. "Come on, m...

Influencer to Sex Slave Ch. 05

by dreamymark9 on Jul 30, 2019
Gay Male

Author's note: This is erotic fantasy and completely fictional. The main character, Jack, is a fictional, generic social media star / influencer, and is not a real person. As always, would love to get feedback in comments and messages. Today was Jack's first day as a sex slave when his master was at work, and it was pretty eventful. He got a ton of embarras...

A Fantasy of Mine Ch. 02

by ima_milkwood on Nov 12, 2019
Gay Male

I say yes, and widen my stance to bend over in these heels. The weight of the tits pull me down and the counterbalance of the ass levels me out, I have never felt so sexy. So desirable. Basically on my toes, with my ass pushed out snorting up the first line of whore fuel. I tilt my head back and take a huge snort to make sure I got every grain as far back in...