Gay Roommate Chastity Stories

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The Male Room

by WatchingAndWaiting on Aug 18, 2017
Gay Male

This is the story of my first time with a man. And my last time... So far. I was always curious, even when I was very young. Looking at men in magazines, especially if they were in revealing underwear and had big, well-defined bulges. I had messed around a little as a kid, but nothing more serious than 'you show me yours and I'll show you mine'. But as the y...

One Sub Stud Ch. 01

by tazemebro on Sep 14, 2017
Gay Male

AUTHOR'S NOTE: This story is a continuation of the series about Chris Donaldson and Justin Corvino, who were roommates during their sophomore year of college. While living together, Justin turned Chris into his personal cocksucker and submissive - a fate Chris initially resisted, but eventually came to love. Along the way, Chris had other admirers. He gave u...

Training My Unwanted Roommate

by asdvPenguine on Sep 14, 2020
Gay Male

I applied for a single dorm room even before I was accepted to the college. Not that I was anti-social, quite the opposite, but I was appalled by the idea of sharing a bedroom with a stranger. Still, it seemed I was out of luck. With only days left before the semester started, I had to accept a double. To make matters worse, neither of my parents had the t...

You are a Sissy Pt. 07: Cuckold

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello, princess. Hello again. I see you are back. That pleases me, sissy. It pleases me that you have come back for more of what only I can give you. The truth only I can give you. And we have come so far together, princess. We have come so far exploring the depths of your sissy feminine mind. And your mind is feminine. Make no mistake about it, princess....

The Possession of Jesse

by Domina_Jen on Aug 18, 2017
Gay Male

Note to Readers: This story contains nonconsensual sex between men. If this isn't your thing, please move on. ***** Jesse was in a rush to get home. Eight full hours with his amazingly hot coworker always brought that old, familiar ache back. Ashley was tall, lithe, and graceful, and just being in the same room with her made him squirm. Even now, in the ca...

The New Order Pt. 03

by Iamkrazy4 on Dec 16, 2019
Gay Male

Part 3: My ass, my mouth, my job No, the guidance counselor didn't fuck me. Though, I would have let him. But, that says more about me than it does about him. What he did do was praise my on stage performance and say I the most enthusiastic "volunteer" so far. He complimented my dick taking abilities and described how my life would be from there on out. Th...

Initiating My Roommate

by blondeallover_00 on Aug 18, 2017
Gay Male

I had repressed feelings for my college roommate before I came to terms with my being gay. I came out my last semester after we had both made other rooming arrangements. Knowing him to be very open-minded, we remained on friendly terms, but I did not have the stamina to reveal my feelings for him. Many of my gay friends and ex-lovers marveled at his slim str...

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...

Connor on Campus Ch. 02

by JasonClearwater on Nov 1, 2017
Gay Male

* * * * * Connor shares his new plaything with his roommate, Stanton. * * * * * ***** Connor wakes to find his roommate, Stanton's, mouth clamped hot and wet around his cock. He lets out a groan of contentment and puts a hand on his roommate's head as the other boy sucks him to completion, shooting his load into Stan's mouth. As Stan pulls off him, Conno...

From Gay Husband to Slave Pt. 01

by assguzzler on Apr 3, 2019
Gay Male

My husband Winston and I were married when I was twenty two and he was thirty. I told him of my submissive fantasies and he role-played with me some at the beginning of our marriage but for the most part he showed little interest in D&S or Domination. We had a good marriage but we often fought as we both tried to dominate the other when it came to who would...