Gay You Are A Sissy Stories

22,837 results
Orientation
Length
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Infinite Scroll

Nephew's Readjustment Pt. 15

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Nicholas was able to refrain from masturbating that night and the next morning, but only because of the tenderness of his ass. Without access to his genita...

Andre Finds Love Pt. 03

by eviltwin52 on Aug 18, 2017
Gay Male

See chapter 2 where my father-in-law fucks me while my wife is away on our honeymoon with her black lover. For those of you who wanted to know what happened to joanie in the final chapter of "It Could Be Worse", the mystery is solved. ***** Part 3: Tomorrow, I thought to myself happily. Lee Anne will be back tomorrow. And her black lover, Leshaun. I...

His Slave Boy 'Good Wife'

by keptsissy on Sep 19, 2017
Gay Male

I called before I got home. He answered on the first ring. He knows better than to not answer immediately. Before he could say anything I cut him off in mid-sentence. "Naked, at the door in just a pair of sexy heels, nothing else, I want you. I'm hard in my pants thinking of your submissive little ass. Your makeup and hair better be perfect, little boy, fuc...

Little Sex Toy Ch. 03

by keptsissy on Sep 26, 2017
Gay Male

"What have you learned, boy?" He's sitting on my couch. I'm naked and lubricated, can feel the K-Y jelly slippery and wet up between my cheeks. It's just two days since he visited me last. My toenails are glossy pink and I'm wearing the pink heels I got to please him. I'm shaved and moisturized baby soft top to bottom. "That I keep myself ready to play, kee...

My Friend's Dad Ch. 04

by Kent100 on Sep 14, 2017
Gay Male

When I awoke, I was startled to see it was dark outside as I laid alone in his bed. My ass, while a pretty sore, didn't really hurt as much as I thought it might. To tell the truth, remembering what he had done to it, it just felt empty and hungry. The clock on the night stand said it was after 7:00 PM, and the first thing that came to my mind was that my gi...

Job Evaluation - New Attitude

by VeryCuriousIan on Mar 18, 2020
Gay Male

Ian stared at the ceiling as he lay in bed, his girlfriend Debbie asleep at his side. He could not sleep, all yesterday's images flashed through his head. No way around it, he had sucked his bosses cock in his office and been forced to swallow his cum. Even worse, his bitch of a line manager had watched him do it. The waves of shame and embarrassment washed...

It Could Be Worse Ch. 05

by eviltwin52 on Sep 14, 2017
Gay Male

Note to readers: If you don't like IR, gay male, and cuckold stories please move on. You can jack off to some one else's imagination. My stories aren't required reading. And yes, I know. I'm a twisted fuck. Lastly, I never sucked a cock. I was merely posing for dirty pictures. ***** Two years after I sucked my first load of cum from Jim's cock and then w...

Nephew's Readjustment Pt. 13

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. * The next weekend, Cynthia called her nephew over in the afternoon. It was time to start preparing him for the next phase in her ever growing plans. She knew th...

PIXIE Sissy Stripper Ch. 01

by EROTICbearscribe on Dec 24, 2019
Gay Male

The imposing shadow loomed over Benji blocking out the lights from the stage. "I asked you a question," a deep voice said. There were no other sounds in the club. The loud dance music had been turned off a while ago. There was only the clinking of dishes coming from the kitchen. 20 year old college student Benji knew someone was speaking to him, but the...

"You Go First" (Ch. 10)

by donaldelliott11 on Mar 2, 2020
Gay Male

This is the 10th in a series. "Samantha" was the 3rd chapter and "Donnie" was the 4th. I regret that my inconsistent use of titles prevents Lit from properly displaying the series. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help authors improve their writing; star rating...