Gay Sissy Anal Stories

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PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

Nephew's Readjustment Pt. 18

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! Last part. ***** Cynthia took her nephew out again the next day under the pretense of it...

Glory Hole Favors Ch. 04

by Kent100 on Sep 4, 2017
Gay Male

The new guy behind me just stood there as I felt his large presence near my exposed and restrained body. He didn't utter a single word to me, probably just bewildered and surveying me in restraints while plotting his course of action. As I heard the adjoining booth's door lock, I immediately felt a hard calloused hand grip my tender aching cock and fondle...

Nephew's Readjustment Pt. 07

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 did indeed end up masturbating herself silly later that evening, rewatchin...

Turning Myself Gay Pt. 02

by bart_allen on May 29, 2018
Gay Male

It had been an exciting experience. I jerked off two more times once I got home that night, focusing more on the thought that I had taken such a large step in turning myself gay. I certainly didn't feel any different, I just did what gay guys do, suck cock. Of a random guy they solicited off Craigslist, chiding myself for the thought. But it was one of many...

Hallowiener Pt. 03

by forummj on Jun 18, 2018
Gay Male

I yanked my cap down tightly and bowed my head. Hunching my shoulders forward I pulled my rucksack tight to my back and made a dart for the front doors. All my fellow students made their lazy way to class as the bell rang. I felt like they all knew what had happened last night, and I didn't just mean the party. I was nervous, almost scared that they knew. "I...

A Questionnaire

by loverofintersex1 on Aug 18, 2017
Gay Male

For Adults only. Present subject: Adult male. 1. Are you wearing panties, yes or no? 2. Are you wearing a thong, yes or no? 3. If either answer is yes, please describe the garment: cotton, bikini, with lace trimming, nylon or rayon? 4. Do you have a semi-erection, yes or no? 5. Approximately what is the length of your penis, erect? 6. What is the ap...

An English Boy Gets Turned Out Ch. 02

by RustyRover on Sep 14, 2017
Gay Male

Sam woke up the next morning with his usual morning hard on. As he put his hand on his erection yesterday's events suddenly leapt to the forefront of his mind. He felt himself blushing as he was submerged with a wave of humiliation. He remembered he was going to be working in a gay porn shop for the foreseeable future, he remembered picking up an enormous di...

A Fill-Up At The Truck Stop

by Cumfusion on Sep 14, 2017
Gay Male

Now here's the scene; Doug was the driver and me a young student fresh from college. I had been chosen to go with him to oversee loading of this big milling machine we were supposed to be collecting. It was the boss who gave the order but Doug had done the choosing. There had been knowing smiles when we left the yard. Perhaps the sight of a big muscular guy...

New Neighbor Ch. 01: Steve Pt. 01

by rimaday on Nov 18, 2019
Gay Male

My name is Steven Vincent wife and I had been married for eight years and lived in a newer middle-class housing development outside of Dallas when this story began. We were one of the original units in the development that now had over 150 houses with plans to double that in the next eight to ten years. We had lived next door to an older couple that retired...