Gay Sissy Gloryhole Stories

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Zebulon

by MVP6 on Jul 6, 2020
Gay Male

This is my fourth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick unsuspecting men into letting me give them my first blow job. In my second letter "Gloryhole Illust...

Exploring a New Store

by TerriC on Nov 18, 2019
Gay Male

"I don't know how he did it, every day in those white tights." I thought to myself, as I pulled a pair of tights up my legs. The semi opaque white spandex stretched around my hardening cock. How the actor who played Robin, in the '66 Batman tv show, wore those tights without walking around hard all day, I'd never know. A wet spot forming on my tights as I sl...

Gym

by MVP6 on Oct 5, 2020
Gay Male

This is my seventh letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore. (M+M, oral, anal) In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick unsuspecting men into letting me give them my first blow job. In my second letter "Gloryhole Il...

Buddy

by MVP6 on Jul 15, 2020
Gay Male

This is my sixth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. Maybe not my best but it has an important message. In my first letter "Costume in a Costume" I describe how I dressed as woman in a Halloween costume to trick unsuspecting men into letting me give them my fir...

Nephew's Readjustment Pt. 08

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. ***** Once her nephew had left, Cynthia got to work. She skimmed through the pictures and video she had o...

Converted to Gay

by bart_allen on Sep 14, 2017
Gay Male

This story is partly inspired by messages from fans, with slight adjustments. Thank you for reading. ***** I wanted to share with you one of my current projects. A twenty five year old male by the name of Eric. Nothing too special in the looks department, but not too shabby either. He was neither heavy or slim, perhaps a slight softness to him. His eyes we...

The Mudroom Ch. 02

by Kent100 on Sep 14, 2017
Gay Male

Recap of The Mudroom Part I... To catch you up... In my mind, my worst fears had just been confirmed by my cousin John. It was actually his big cock that I had sucked off at what I thought was my anonymous gloryhole setup at my house. We had hooked up off a Craig's List ad that I had posted and I was mortified with what he just said to me at the family par...

Finally

by yesplease8 on Sep 25, 2017
Gay Male

I have been happily married for over 10 years. My wife and I are sexually adventurous and open-minded. We have always openly shared fantasies. My wife always makes an effort to realize all of our fantasies. My wife, Anne, is a beautiful woman who takes very good care of herself. She is a natural blonde with natural 36 D tits and firm, muscular legs. Out in p...

HypnoSissy: Ecclesiastical Sucking

by silkstockingslover on Oct 15, 2017
Gay Male

Summary: Cock sucker discovers a church where he can worship. Note 1: Thanks to hfernandez1983 for the story idea and the intriguing revelation that hypno sissy videos exist in the first place. Note 2: Of course, all participants are at least 18-years-old. Note 3: Thanks to Tex Beethoven, Robert, Thor_pf, and Wayne for editing this story. Note 4: Thi...

Sissy

by MVP6 on Jul 15, 2020
Gay Male

This is my fifth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. (M+/M, oral, anal) In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick an unsuspecting man into letting me give him my first blow job. In my second...