Shemale Gloryhole Stories

1,788 results
Orientation
Length
Source
Infinite Scroll

It's a Wonderful New Life

by alexyzia on Sep 16, 2017
Transsexuals & Crossdressers

I met Sherry at a bar. Imagine that. I often picked up women at bars. I'm a good looking man, have a nice sporty car, cash flows freely from my pockets - at the bar anyway. So I do OK at snagging a tipsy babe for a nights folly. But all of the sudden karma has caught up with me. When I hit on her she told me to back off or I'd be sorry. When I persisted, pol...

What It Takes Ch. 02

by YKN4949 on Sep 25, 2017
NonHuman

Dear Reader: This is part 2 of a 4 part story. All four parts are written and will be posted sequentially. In Part 1, struggling space crew member Luna walked in on a crew member, Dr. Janice Alton, sharing an intimate moment with a giant space slug. This is not one of my "normal" genres (check out my lesbian, shemale, and incest stories). I am not sure if I...

Family Issues Ch. 01

by allthatisfuta on Dec 10, 2017
Transsexuals & Crossdressers

Warning: This story contains futa on male action. It has a semi non-con or at least a hot dickgirl domination theme, cause that's my kink. There is also a nice love story (In my humble opinion) that is brewing, because that's my kink too. Why here and not in SF or Non-Con? I think my story will feel comfortable here amongst ruwild, sugarandsalt, Xtina, sky...

Bayonetta's Abuse Ch. 08

by ChainedToAKeyboard on Jul 10, 2019
BDSM

A hidden truth is laid bare. Will it illuminate? Or cast everything into darkness? Bayonetta's Abuse VIII - Whispers In The Dark Female voice: James... ... Female voice: Can you hear me James? It's time... ... Female voice: James! It's time to wake up... * * * * * The light slap of a hand on his cheek brought James to consciousness. Immediately he wa...

Josaphine's Conversion

by WallabyJack on Jun 19, 2019
BDSM

This is my first story, I hope you all like it. This is about a Dominant using VR (virtual reality) to take things to a new level. The concept is based around the incredible advances in VR technology and motion sensor suits (think Gollum in Lord of the Rings) and how it might one day be used by those with devious minds. Robert knew Josaphine had an active...

Bringing Her Along Ch. 06

by honourableboy on May 30, 2018
BDSM

- well my dear. We should get dressed and get going. And then to us - You two. Chauffeur uniform. Slave. Just as you are. - And boy, go get the cage in the back of the truck. Tamara and I dashed to our rooms to get into our Chauffeur uniforms. Something we could be seen in the outside world. For me it was shiny black shoes, pressed and tight dress slack...

The House of Lesslie Ch. 02

by gothicboibitch on Sep 19, 2017
Fetish

I. I woke up. Even after having taken over the House of Lesslie weeks ago, each morning was still the same, and came with the same feeling of disorientation, in need of a few moments to adjust to the realities around me, as new as they were. The bedroom around me was still darkened by heavy, burgundy curtains that allowed only a sliver of the early morni...

Pirate on the High Seas

by spitzharder on Sep 26, 2017
Transsexuals & Crossdressers

The westerly winds had been blowing steadily for the last three days as the old barque stood out to round the headland, the casual eye would not notice her stained sails were in fact quite new and only the briefest glimpse of copper showed that she had been careened recently. Salt stained timbers gave the ship a tired and dilapidated air, though the crew jum...

The Wonderful Adventures of Miss K Ch. 2

by BrettLynn on Sep 13, 2017
Transsexuals & Crossdressers

Welcome to the next installment of my wonderful adventures. I hope you enjoy reading this one as much as I enjoy writing it. I reserve all non- electronic and commercial rights to this work. If it is illegal in your jurisdiction to read this work, please do not read this story. * * * * * Miss K brushed a strain of hair out of her face as she backed her SUV...

The Office Receptionist

by cowboy109 on Sep 12, 2017
Erotic Couplings

I’m the first to admit that I don’t have much luck with the ladies. They keep their distance and turn serious around me. I guess I lack that physical hotness or pompous confidence. My job has a lot of serious and uncool people who never ventured to the gym or read a GQ article about men shaving their legs. There are also very few women. The once that are the...