Gay Tricked Into Chastity Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

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...

My Sweet Bitch Ch. 04

by JasonClearwater on Jun 18, 2018
Gay Male

Author's note: Unconvinced Jaspar's learned his lesson, Kleine insists he bring Carl to his room, so he can ensure Jaspar handles him correctly going forwards. Contains themes of non-consent/reluctance. * * * * * Sam helped me off the bed, and I stumbled into the bathroom to take a shower on weak legs. It'd been a long night. Still, my first experience...

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 Chaste Boy and the Locksmith

by fantaseeboy on Oct 31, 2018
Gay Male

A little bell tinkled softly as the door closed behind me. A shiver shot up my spine as I stood there in that little shop waiting to be helped. For a brief moment, I thought about running out the door and living with my current predicament. Just as I was about to act on that impulse, an older man stepped from behind a curtain. He looked to be older than my f...

Snowball Effect

by sr71plt on Aug 18, 2017
Gay Male

I couldn't resist Michael Dabney's proposition in the Checkers Lounge at the LA Hilton Checkers hotel during the Entertainment Industry Advertisers' Association convention—well either of his propositions, really. I'd never done it with a black man before, and that had become somewhat of a special fantasy of mine. I was attending the EIAA convention, because...

The Highland Festival Ch. 06: The Walk

by BareBearsFan on Apr 10, 2019
Gay Male

Chapter 6 -- The Highland Festival -- Misbehaving ***Hello Readers Quick note, my stories tend to progress a bit slower, if you're looking for quick paced sex scenes try another story. This story contains nonconsensual sexual acts. Also, some past people nitpick about small consistency details in my stories. I'm not writing a classic novel, I'm not goi...

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...

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...

Progression Ch. 04: A Real Fitting

by klapperz on Mar 6, 2018
Gay Male

Nathan hung out with Jeff and his other flatmates for the day. He had been so focused on Ryan and Jack that it was nice to have a break and be normal for the day. They went to the pub for lunch and then watched some films. Before he knew it, the day was over and everyone was heading for bed. The next morning Nathan woke up for work. He panicked, remembering...

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...