Shemale Gloryhole Stories

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A New Life

by JKBigDaddy on Sep 13, 2017
Transsexuals & Crossdressers

Bennie, age 21, lived on his own for the first time in his life. It was his first night in his new apartment. He had lived with his parents, Joanna and Chris Smart until just today. This was the start of a new life in many ways for him. Bennie, or Ben as most people called him, worked as a telecommunications tech for a local phone service. It was his first...

A Strange Romance

by toniukcd on Sep 16, 2017
Transsexuals & Crossdressers

Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to the East Midlands. Ever since my parents decided when I was...

Jess

by DaniW on Jun 11, 2019
Transgender & Crossdressers

I first met JD in the 6th grade at Westminster Middle school. We had several classes together and after being paired up repeatedly for science projects and other activities, we became good friends. Our days at school often extended to doing stuff together after school and on the weekends and eventually even the occasional vacation together. JD and I became i...

Wife's Friend with Benefits Ch. 04

by DarkBreezly on Apr 9, 2019
Loving Wives

Authors Note 1: I apologize for leaving this series for so long. A few of you have poked me over the months, so here it is finally. I have been working on a more visual/illustrated story line and that takes a great deal more time and effort to develop, so I wanted to get back to more story based lit. Please let me know in comment or message if you would like...

Afro Stress Relief Ch. 09

by llts1970 on Feb 3, 2020
Transgender & Crossdressers

After a hectic and traumatic weekend, it was Monday again, I was still in a state of shock after what had happened. I spent most of the day at my desk doing very little, and wondering if any of the loading bay crew had seen the photos of me kissing Drake's ass, but I thought they wouldn't recognize me, as I was fully made-up as a sissy in the picture, but I...

Wannabe Cuckold Gets Found Out

by tombrennen on Jan 20, 2020
Fetish

A little about myself before I start the story. A trim 35 year old man that would probably be diagnosed as a sex and porn addict. As long as I can remember, I've been extremely sexual. Starring at cleavage and tight pants, led to porn mags and the occasional video, led to the internet. Once the internet exploded, so did my sexual fantasies. Shemale porn, and...

The Greatest Liar Ch. 02: Exposure, Disclosure

by alexandrarios on Jul 2, 2019
Transgender & Crossdressers

Author's Note: This is a continuation of the narrative which commenced with "My Awkward Phase", which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. ***** Natives say that life cannot exist in LA without a car and money. My last days in LA proved those truisms. I'm from Brentwood, "...

The Greatest Liar Ch. 01: My Awkward Phase

by alexandrarios on Jul 3, 2019
Transgender & Crossdressers

Chapter 1 My Awkward Phase The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne in the Newspaper Office, our refuge at University High in Los Angeles. A g...

It's Only Temporary Pt. 02

by ChangeYourPassword on Dec 24, 2019
Transgender & Crossdressers

Continued from Part 1 -- Read that first! Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story and the fetishes involved, great. If not, please forget t...

The Bitch Is Cheating On Us

by qhml1 on Sep 19, 2017
Loving Wives

Something a bit different .................................................. "What did you just say?" I looked over at my wife, shocked. She'd just told me she intended to go to the Bahamas for a three day weekend with another man. "Please, Mike. It doesn't mean anything, just a little fun." "Not no, but hell no. This isn't what we agreed on, not at all...