Gay Sissy Fisting Stories

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Infinite Scroll

For Destruction, Ice.

by JasonClearwater on Oct 12, 2017
Gay Male

***** This story is not an essential part of the Will/Jesse timeline, and involves non-consensual sex between Frost and Jesse. If you don't enjoy this kind of content, I would advise you not to read it. ***** Special thanks to Holliday1960 for picking up the typos, and giving me feedback on this exceptionally long piece of fiction. ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~...

The Journal

by Circusfreak19 on Nov 27, 2017
Gay Male

Hello again you lovely people! Thank for the great feedback on my previous story, here is the sequel! It doesn't do so well as a standalone so I strongly recommend reading The Circus first (if you haven't already). I've put the entire thing up in one go again so feel free to grab a beverage of your choosing and settle in for a slight darker tale this time...

Marking the Decades

by KeithD on Nov 18, 2019
Gay Male

Chapter One: New Year's Eve 1989 There were four of them on the bed in the second-floor master bedroom of the Baccarat Hotel and Residence Condo building on Manhattan's West 53rd Street, conveniently located near the Broadway theater district. The caterers were downstairs in the living area doing last-minute preparations for Ted Sullivan's early-evening buf...

City of Angels

by Love_Brokers on Sep 19, 2017
Gay Male

Evan Malone liked the midnight shift. 12 am to 8 am along a stretch of Pacific Coast Highway right at the border of Malibu. It was never dull, and the arrests and citations were easy and built up his record. Most of the time he was pulling over rich drunk fucks in their BMWs, Porches, and Mercedes. Half the time they had hookers or call girls in the front se...

My Hero

by Bundy5 on Sep 26, 2017
Gay Male

He stares at me with a mixture of pity and disgust in his eyes, and I sneer back at him, my contempt loud and clear. I didn't know it then, but that doorman would one day mean the world to me. ** My name is Peter 'Pinky' Benson. I'm twenty and a half years old, and I'm going to be all alone for the first time in the big city. I'm moving there to attend an...

Descent

by EroticMonster on Aug 18, 2017
Gay Male

The sequel to Contraction. ***** "Your future is with me now." With those six words I became Cody's boyfriend and he became my saviour. Jenny and I were over. Two years of an incredible sexual journey had ended with threats and recrimination. I had been thrown out of the house I had shared with her for almost the entire relationship, and a cloud of humil...

Falling for Matt

by icyblue on Sep 14, 2017
Gay Male

Normally I'd wake up regretfully, instantly turning over and trying to get back to sleep. Not today though. Today I was out of bed and on my feet practically before I had my eyes fully open. I felt giddy with excitement and could hardly wait for the day to get started. After a quick stretch and a glance out the window to make sure the weather suited my mood,...

Becoming Mark and Janet's Girly-Boy

by BuckyDuckman on Mar 30, 2020
Gay Male

Who knew taking your turn at washing the dishes could turn sexy? That's exactly how it started as Janet squirmed up close to me, wrapping her arms around me from behind and pressing her chest against my back. I might not have had hands on my back but I swore I could feel her stiff nipples poking me. "Hey baby?" she cooed, kissing the nape of my neck and se...

Held for Ransom

by rae121452 on Apr 17, 2019
Gay Male

The first thing that Gavin was aware of when he woke up was that he had a hell of a headache. The next thing, when he opened his eyes, was that he had some kind of bag over his head. Then, in rapid succession, that he had to piss, he was sitting on a hard chair and that his hands were tied behind his back and that he was naked. "Hey, it looks like he's comi...

Stefan

by perihelion on Sep 25, 2017
Gay Male

I always preferred the company of boys and never liked to play with girls, even as a child. I have two older brothers and everything in my home was all about three boys. It was a life of sports and typical guy stuff like hunting and fishing, climbing trees, and the things that make a macho father's chest swell with pride. I never really thought much about it...