Shemale Gloryhole Stories

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Orientation
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Infinite Scroll

Mandy's Sexcapade: the GloryHole

by Syzoth on Dec 2, 2019
BDSM

"GloryHole" is a quasi-prelude to the "Sharing My Wife Amanda" series, but can be read as a standalone. This story is the first idea I ever had for Literotica, and I hope you enjoy it. -Syzoth * Amanda and I recently celebrated our 9th wedding anniversary, and it's easily been the greatest 9 years of my life. I adore the ground that she walks on and lo...

Home Alone with Beth

by Benny024 on Sep 19, 2017
Transsexuals & Crossdressers

Warning, this title contains the following: explicit sex, graphic language, and some violent situations. In addition, all characters in any sexually explicit conduct are over the age of eighteen (18) years at the time this story was written. * I had recently sprained my ankle badly at our annual, summer picnic softball game and was gimping around on a cru...

Jamie the Gloryhole Slut Ch. 02

by jr0777 on Sep 16, 2017
Transsexuals & Crossdressers

Hi guys, I got a lot of positive feedback on my last story, part 1 of Jamie The Gloryhole Slut. Thank you everyone for the encouragement. With that encouragement in mind, I give you my second story about slutty Jamie. I hope very much that you enjoy it and it turns you on -- it does for me. Love, Jamie * It was a typical weeknight dinner meeting with cli...

The Thrill is Gone

by John Connors on Oct 6, 2020
Celebrities & Fan Fiction

Disclaimer: This story is a work of fantasy, fiction, parody and satire. As such, no offence is meant to anyone who is mentioned within it as they would never act this way in real life. This is just a fictional erotic fantasy story to be read by those over 18 years of age. All characters mentioned within this text are 18 years of age or older and are theref...

First Time Buttslut

by missyminx on Sep 12, 2017
Transsexuals & Crossdressers

I just got home from the adult bookstore, let me tell you what happened to me. Arriving at the abs I went inside and purchased a debit card from the clerk and went into the arcade. Inside the arcade there are eleven booths, two are side by side, I saw that one was occupied so I entered the one beside it took my pants off and sat there in my pink panties stro...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Hypnotized to Try a Gloryhole

by rand0m on Aug 22, 2018
First Time

This is a 100% true story I finally decided to write. I'm not much of a writer or story teller so this was meant to be more of a recollection of the first time I sucked a cock and the story behind it. Although I consider myself straight, I've always been into eating my own cum. Like a lot of guys into this, the idea is a huge turn on but after blowing my lo...

A Change of Management

by alwaysreadyfryou on Sep 13, 2017
Transsexuals & Crossdressers

Sorry everyone for the massive delay between stories! For the record, the order of stories should be as follows: The Magic of the Lamp, The Land of Genies, A Failed Escape, A New Life, and now the fifth installment of the Shemale Genie Chronicles, A Change of Management. Hope you enjoy and leave any feedback you have! ***** Tommy awoke the next day as he h...

Cum-mania at the Gloryhole

by jptune on Sep 13, 2017
Fetish

Well, I guess I just can't resist my girl friends imagination. She comes up with these ideas that wind up driving both of us nuts. She keeps thinking of different ways for the both of us to load our mouths with cum. Last time she got filled with cum in all her holes and I posted the experience in the story named "fill er up". This time it was the gloryhole....

Payback's a Bitch

by sissymaidallyson on Sep 13, 2017
Transsexuals & Crossdressers

Knelt on my knees and taking a glance to my right at the sight of a woman counting cash whilst I sucked off a guy I started to wonder how this had all happened. I had a good job and didn't have a huge problem with getting lovers. I was straight and loved women but here I was – nothing but a sissy prostitute being rented out for the oral pleasure of men I di...