Gay Penis Shrinking Chastity Stories

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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...

That Full Feeling

by GE216237 on Aug 18, 2017
Gay Male

Forget what the net says. I've "experimented" on myself for years. As I learned pleasure and pain, I began to combine the two into a naughty bliss. When I found out that I can take a 22" dildo all the way up my ass, my self-pleasure took off!!! It only took 10 years but I finally did it. Sounds crazy? Try it! Once I got past the sticking point, it just sli...

A Movie, A Massage, and...

by STPeanut on Sep 14, 2017
Gay Male

I was at home. Finally alone I popped a tape in the VCR. I had been filled with a sexual tension lately and was gonna do something about it with the house empty for a few hours. On the screen a blond woman was being fucked by a hard bodied stud with a huge cock while a petite Asian girl squatted over her face. The blond lapping up at the shaved pussy above...

Room Serviced Pt. 01

by bigblue212 on Jul 6, 2020
Gay Male

Carson drummed his nails against the marble counter, surveying the drab grey figures as they lingered about the hotel lobby. Clarissa peered up from her desk. "I'm going to bite your fingers off. Stop that." He glared at her. "And I'll report you to HR." "Hey, I got you this job," she snapped. "Don't think I won't get you fired." He hoisted himself onto...

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...

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...

Becoming Daddy's Girl Ch. 01

by Sungmehetu on Mar 6, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** It might have been the death of my mother and my only sister in the car accident. It might have been that I tried to drink away the depression while I was hundreds of miles away from home at college. What I do know is two things. My father would be furious I had failed out, in jus...

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...

The Video Ch. 1

by upnorth on Aug 30, 2017
Gay Male

I was cutting the grass on a hot July afternoon, trying to think up an excuse to quit, when I looked up my driveway. Joe, a good buddy I know from work was just pulling in, in his old beat up car. I knew and bull shitted with a lot of guys from work but Joe was special. Through the years, we had shared a lot of personal stories in private, about ourselves,...

Poor Simon Ch. 09

by Cruel2BKind on Sep 14, 2017
Gay Male

*Sorry again for the cliff-hanger, here is chapter nine of Poor Simon. All characters are 18+ One of my pet peeves is when characters on Lit stories get into terrible situations but everything is still happy and okay and the situation is light. When it gets dark in my stories, it gets very dark. You've been warned.* * I guess I expected it to be bigger....