Gay College Chastity Stories

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Cherry's Graduation Party

by CherryWood on Aug 30, 2017
Gay Male

I finish applying my lipstick and take one last look at myself in the mirror. I'm almost stunned at the reflection that stares back at me. After months of training and feminization I look like the perfect slutty fuck toy. I feel my little cock begin to get hard and strain against my chastity device as I look over my changed body. The strict exercise regimen...

A Weekend of Servitude

by HerLittlePiggy on Sep 14, 2017
Gay Male

Thank you Susurrus for the help editing this monster. ***** Richard Michael Quail, Rich to his family and friends, Mr. Quail to his associates and adversaries, sat quietly at the round high top table beside his sexy, buxom wife and sipped on a fine 18 year old single malt scotch. They were both well dressed: she in an expensive blue designer dress which d...

Progression Ch. 03: The Show

by klapperz on Mar 6, 2018
Gay Male

Nathan turned and looked at his clock. It was barely 3am and he was just lying there looking at the ceiling. No matter how hard he tried he couldn't stop thinking about his session with Ryan and Jack. He put his hands under the blanket to feel his cocks prison and attempt to get some relief, but it was useless. When he tried to play with himself his cock jus...

Enslaved by Myself Ch. 03

by Lausunaht on Sep 14, 2020
Gay Male

I was dreading what was about to happen. My master was going to hurt me badly to ensure I would never rebel. I knew this for certain because I would do exactly the same if the roles were reversed. I could only hope that my affection for myself was strong enough to limit the pain. He left me tied up alone for hours, I was thirsty as I didn't drink the whole n...

His Plaything Pt. 03

by Cumpup39 on Jun 5, 2019
Gay Male

I considered my current situation. I was standing naked in a hotel hallway, wearing only a stainless steel chastity cage that contained my throbbing and swollen cock. I had a load of dried cum on my face that had been left there by a man I only knew as Master. He came to my room, handcuffed me and fed me his cock and cum, except for the part of the load I n...

Progression Ch. 07: Decision

by klapperz on Mar 28, 2018
Gay Male

The next few days went pretty slow as Nathan counted the minutes until he could see Jack and Ryan again. It didn't help his frustration than Kevin, who was now sleeping in his bed, had quite a high sex drive. He was always demanding handjobs and blowjobs, which kept Nathan in a constant state of arousal. "I'm off to see the guy I told you about," said Natha...

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...

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...