Sissy Gloryhole Stories

6,957 results
Orientation
Length
Source
Infinite Scroll

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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Covid 19 - Pete Turned into Charleigh Pt. 05

by His_fag_wife on Sep 14, 2020
Transgender & Crossdressers

It was a long night, Charleigh drifted off, but the warmth in her ass, the stretch and lack of comfort as her hands were padlocked together made restful sleep almost impossible. She kept on drinking but in the early hours became aware of an ever increasing need to piss. She thought she'd be able to hold on, but she was getting more and more desperate. By 5...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...

The Gloryhole

by wizard666 on Sep 13, 2017
BDSM

Brad and Janet had been together for many years and although they had an open relationship, they had never been to a party like this one before. As they drove to the house, Janet was trembling in nervous anticipation. She had never done anything this adventurous before, but despite her fear she could still feel the excitement building! Janet had worn a slink...

Gloryhole Addiction Ch. 02

by Brittni4u on Dec 19, 2018
Fetish

It has been a several years since my dirty yet amazing gloryhole experience. At that time, I was 18 years old and still in high school. It was supposed to be a sneaky one time experimentation which turned into a nine month long, multi-visit, wonderful cock sucking experience that has never left my memory. I have always had an oral fixation when it comes to...

After School Ch. 02

by Faye_Skylark on Sep 25, 2017
Erotic Couplings

Crystal McLaren stood anxiously in the cramped backroom office of the local adult book shop. She could never quite work out why they were called book shops, since they she didn't see many books in the store. Instead it was mostly filled with adult DVDs, toys, outfits and miscellaneous products. Crystal was eighteen years old and a student in her final year...

First Time for Everything

by qazwaz on Sep 12, 2017
First Time

My wanting cock throbbed around my hand as I glanced down at my illuminating phone in my dark car. "Just got here" I replied, before switching internet tabs to the previously-loaded video of a blonde girl in a gloryhole. I had a long drive that day, about 3 hours to my hometown destination. Having broken up with my girlfriend a few weeks back and not having...

Abducted and Turned Out Ch. 05

by dawnib66 on Sep 19, 2017
Transsexuals & Crossdressers

.... I lapped at her pussy as she intermittently moaned and derided me. "Eat that cunt, you sissy whore. I know you prefer cock, don't you? Answer me slut!" she said as she forced my face deeper into her pussy. "Yes, mistress," I said into her cunt. As I did, she moaned loudly and her pussy spasmed as she gushed into my face. "You are a good little bitch,...

Date Night with My Wife Pt. 02

by amadbaker on Aug 31, 2017
Group Sex

As we entered the bookstore we realized how late it had become, without noticing it was already after 2 in the morning. That was OK since our favorite store is out away from towns and city's so it doesn't get more than trucker traffic and since it's the weekend there are not a lot of them out and about. Shawn and I were following my sexy wife Debbie around w...

One Gloryhole Outside Breeding, Kentucky

by targetthyself on Nov 24, 2018
Miscellaneous

Somewhere, in the cosmos, lies the truth of our existence. It's siren song drives us forward, forward into the unknowable reaches of space, and time. Hoping to boldly discover their secrets. What is it about the unknown that drives us so? What is the appeal of knowing? Is it the value of the knowledge we will gain? Is it the thrill of the risk we take? Or is...

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