Gay Sissy Spanking 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...

Spanked and Buttfucked Asian Male

by asianspankee on Aug 30, 2017
Gay Male

I'm an Asian male, with slim and very smooth naturally hairless body, and average height. The story happened when I was in my twenties. I hope you enjoy reading it... Ever since a teenager I've always had a very strong, repressed desire to get fucked by another man. I think one reason is because my body is quite slender, and extremely smooth devoid of any b...

The Backpacking Trip Ch. 01

by lockedinsteel on Nov 21, 2017
Gay Male

"It's what I want for you baby," said Jamie. Her husband, Daniel, was still a little uneasy with the idea. "I know you've wanted to explore that for years and I think that if you get the opportunity you should. In fact, I'm giving you an order. Do it if you get the chance. Promise me!" she told him. "Okay, Okay I get it. I promise, my love," he replied....

PIXIE Sissy Stripper Ch. 02

by EROTICbearscribe on Dec 24, 2019
Gay Male

Sunlight played peekaboo through the blinds and woke Benji from the best sleep he'd ever known. He opened his eyes and breathed deeply. His eyes adjusted to the bright light and he looked around the strange bedroom he found himself in. He noticed a fuzzy pink sweater draped over the back of a chair in the corner of the room. There was also a pair of yello...

Becoming a bitch

by Testytesterton on Nov 28, 2019
Gay

(Skip this if you don't like boring behind the scenes stuff. Wow! Over 3000 likes and story of the week for my first story here! Thanks to everyone who has liked, bookmarked or commented. The feedback lets me know what works and what might need work. I would love for this to be the most popular story in its category, so if you like the story, "like&quot...

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Sissy Slave Toy

by slavegurl_veronica on Sep 16, 2017
Gay Male

Where it all began was at gym class in my freshman year of college. Gym was a course requirement for freshmen and I couldn't wait for it be over. I was skinny and weighed only about 130 pounds. I was not at all athletic and one of the smaller guys in the class. Fortunately though there was another guy named Alex, who like me, was also decidedly not jock mate...

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...

Beauty and the Beast Pt. 01

by Suzzique on Dec 17, 2017
Gay Male

I hesitated a long time before I advertised on Craig's list. I was 18 and had left school two months before. I had a place at university for the following October, almost a year ahead. I was living at home and had a mindless temporary job in a solicitor's office that made no demands on anything but my time. I'm a very shy person and no one knew I was gay exc...

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...

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...