First Time Gay Gloryhole Stories Stories

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Adult Shop

by LucyFrance11 on May 7, 2019
Transgender & Crossdressers

As you will have noticed from my previous stories, I am gay. But for the last 20 years I have also been crossdressing and I now spend over half my time dressed. Over the years I have become more adventurous and now regularly dress in public. I live in the South of France not far from Cap D'Agde which during the summer is the sex capital of Europe. There is p...

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...

A New Adventure... Ch. 02

by johnjinglez1 on Jun 6, 2018
Transsexuals & Crossdressers

This is a continuation of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real. *** After my first three encounters with TS and CD's left me feeling unfulfilled I gave it up for a few months and figured it just wasn't for me; I went back to having sex with...

Gloryhole Event

by carriekitty on Apr 22, 2025

Well i decided to try something new for a change, I spoke to Kerry (friend from previous stories) and she told me that there was a greedy girl event going on this Friday night, Carl was out with his friends and I had nothing planned, so I thought I'd go down and see what's going on. So Friday soon came and I got freshened up, put on some smart casual clothin...

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First Time at Gloryhole

by Wizkid813 on May 12, 2020
First Time

My friend David and I went on a wild night the weekend I turned 18 years old. He turned 18 a few weeks prior. We wanted to hit every porn store and ever strip club in the area. We lived in Tampa Florida and all the porn stores were in an industrial park called drew park. We went to two of them and just looked around. On the third one we got a little more dar...

Futa Gloryhole

by Rex711 on May 22, 2020
Transsexual

(No new chapters will be released for a while as I'm unavailable due to injuries. Unknown away time) This is my first story so it won't be amazing but i will try my best and i hope everyone enjoys it, I am writing this because there aren't many good Futa Gloryholes ( at least not none i haven't already read ) I plan on writing quite a bit for this story sinc...

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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...

Connie at an Adult Bookstore Ch. 01

by cmorehead on Sep 13, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * Let me start by introducing myself. My name is Connie and I am a 40-something tr...

FAWC 1: A Gloryhole Adventure

by BuckyDuckman on Sep 12, 2017
Chain Stories

(Moderator's Note: This story is a submission to the first Friendly Anonymous Writing Challenge (FAWC). The true author of this story is kept anonymous, but will be revealed on June 22nd, 2013, in the comments section following this story. Each of the stories in this challenge are centered around the common theme of the main character being an author who the...

Gloryhole Jobs In Many Situations

by lrocks911 on Jan 23, 2016
Science Fiction

*some of these stories will have to do with the POV of the person getting their cock hand/blow/footjobbed, some of the stories will simply have a greater emphasis on just describing the cock getting hand/blow/footjobbed by itself In an alternate reality, men can insert their cocks anywhere, at any time so that they can be massaged or rubbed by a woman's feet...

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