Gay Chastity Cuckold Stories

356 results
Orientation
Length
Source
Infinite Scroll

Myth Debunked

by lmhsfan on Aug 18, 2017
Gay Male

Ian was on a roll. With the second draft of lyrics well under way and the melody writing itself, he knew he'd finally gotten it. He'd finally written a love song to rival all love songs. Honest, pure, impossible to ignore: exactly what he was going for. Becca had to listen to this. She'd have no choice but to love him and allow herself to be loved in return....

More Than I Bargained For

by lexxjld on Aug 30, 2017
Gay Male

[ also known on various sites as horny_dad and lexxjld ] (Note: Because of the length of time it has taken me to finish this story, I am submitting it whole. If you have kept the first parts, this replaces them. Enjoy!) 1: Fantasy I stared intently at the small video playing on my computer screen, even though it was the fourth time I'd watched it. Only th...

Turning into a Bi Cuckold Ch. 01

by secondsamuel on Jan 20, 2020
Gay Male

Author's Note: I love writing. But due a medical condition, I often rely talk to text program that isn't always accurate to dictate much of my work. If you like a series, please consider volunteering as an editor to help me produce more stories faster. * I think every man feels at least a little insecure about the size of his penis. Okay - maybe not ever...

The New Slave Ch. 08

by martin_x59 on Sep 14, 2017
Gay Male

At five thirty Shane, Joe and myself get in the van and climb into the back. We pick up the blindfolds and I'm about to put mine on when my phone vibrates. It's from Sir again. "Tie their hands behind their backs then put on your blindfold." "I'm to tie your hands," I tell them, "Sir's orders." I find leather restraints in the back of the van and I tether...

Cabin Adventures Pt. 04

by MrSunshineBoy on Sep 14, 2020
Gay Male

About 10 minutes had passed, James struggled weakly against his bonds. Despite that, his nose got accustomed to the horrible smell, it was still too much to bear. James coughed and gagged a few more times while turning his head right and left. The scent of all these things combined with him sweating and panting made him a bit dizzy. All the gunk that covered...

Darren & Dean do Dale Ch. 03

by betamale08 on Aug 7, 2019
Gay Male

After we had our steaks, which were perfect I might add. I did clean up again, donning my apron over my top and mini-skirt, where again I was playing little miss homemaker for the two men Darren and Dean while they sat out having coffee and then joining them once I was finished, I came back out to them with three beers, one for each of us this time. I didn't...

How I Found a Keyholder Ch. 05

by 1077ad on Sep 28, 2020
Gay Male

5.a: Video #5: the nude beach After another week where Sir had only inspected me, I was blazing with horny frustration. On Monday, when I scanned that week's code, I was hoping the next video would involve something, anything, to take the edge off. "GET SATURDAY OFF WORK. SCAN AGAIN FOR INSTRUCTIONS AFTER 9 AM SATURDAY." Well, that's an inconvenience! Doe...

Black Cock Worship: A Man's Fall

by silkstockingslover on May 1, 2018
Gay Male

Summary: Straight guard learns of black inmate's power over all. Note 1: This is dedicated to the real Ken who retold this surprisingly largely true story. Note 2: Thanks to Tex Beethoven, thor_ph, Robert, and Wayne for editing. Prologue: I'm the prison guard and Kareem Mwangi is the prisoner, so you would have thought I had the upper hand, and until...

Slime and Ice

by Araddion on Aug 18, 2017
Gay Male

"You got it?" Sanchez asks after a long drag on his Marlboro. His name's an affectation: he's lily white. He's Mom's sweet boy, cleans his room, does his own laundry, kisses her goodbye, sells joints and pills to highschoolers on Saturday night, then goes to Church on Sunday pretending to be sinless as starched white sheets. Typical American shyster. S...

I Turned Myself Out Ch. 03

by drmweaver705 on Aug 24, 2020
Gay Male

"Warning: this video is designed to turn straight men into gay bottoms. Don't say you haven't been warned..." The female narrator had a breathy, clear, commanding voice. It was a voice to be obeyed. "You've stripped yourself naked and stretched your ass in preparation for the arrival of your first ever top..." In fact, I was naked, lying in the marital b...