Shemale Gloryhole Stories

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Jamie the Gloryhole Slut

by jr0777 on Sep 16, 2017
Transsexuals & Crossdressers

I am a cocksucking gloryhole slut. It all started a few years back when I first discovered gloryholes. An adult bookstore in my town had some video booths in the back that it took me quite a long time to get the courage to go into. Eventually I did, and for a long time I was very happy putting my cock through the hole to get serviced by some mouth slut on t...

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...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....

Accidental Gloryhole Slut

by FiftySomething on Aug 6, 2019
Fetish

Mike had fallen off the scope entirely. I'm not sure what happened to turn him off, but he completely ghosted both me and my wife for a few weeks and we just gave up. Maybe he just got bored. Maybe he finally got skeezed out after he accidentally fucked me up the ass that one time. Whatever happened, it was back to more or less monogamy for me and my wife, w...

Futa heaven

by Taker on Mar 18, 2020
Transsexual

You are an average young 20 something college student. You’re pretty slim, but with a little muscle, fairly handsome average guy. You are 6’0” 6.5 inches. The following stories will be various unconnected sex fantasies.What's next? Abby Sarah Lauren Master hailey Gloryhole Blowbang Bri What's next? Abby Sarah Lauren Master hailey Gloryhole Blowbang Bri...

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Pam's Shemale Experience Ch. 08

by majicman21 on Mar 11, 2019
Transgender & Crossdressers

Content warning: one scene with a golden shower... Pam woke with a start. It took her a few seconds to hear her alarm ringing. Next to her, Tanya was still asleep, and further down on the bed, Alex was as well, her head resting on Tanya's thigh. Pam reached over to the bedside table and quickly turned off the alarm. Neither of the other women stirred....

The Mistaken Gloryhole Ch. 01

by DickThePimp on Aug 12, 2019
Celebrities & Fan Fiction

My wife Kim Kardashian and I are coming back home from a short trip to Vegas. We're driving back in my pimped out Escalade, green and gold... pimp colors baby. My cousin Spence (The King Of Queens) is in the back seat. He came along, but lost all of his money in the casino. He's pretty bummed out about it. He's been downing Redbulls the whole way back. Don't...

Pam's Shemale Experience Ch. 11

by majicman21 on Jun 1, 2020
Transgender & Crossdressers

Content warning: one scene with a golden shower. "Ah, what a way to start the day," Tanya sighed, letting her cock slip from Alex's pussy. The shemale had just filled it with a load of cum, dribbles of that gift already leaking out. Pam smiled from next to them, at the possessive yet affectionate way Tanya slapped her cock onto one of Alex's thighs and...

A Cuckold's Tale

by CastleDJK on Sep 14, 2017
BDSM

Based on Chaucer's Canterbury Tales Prologue Three Mistresses are lounging around the pool, chatting and laughing, while their three sissy maids stand by to attend to them. Big breasted in a white string bikini, redhead Mistress Reeve is enjoying a foot massage from one of the sissies at the side of the pool. Lady Night, raven-haired with an alabaster whit...

Sex Funhouse

by DickThePimp on Dec 11, 2018
Celebrities & Fan Fiction

This is a perverted funhouse fuck parody... It ain't real "This is great babe... It looks like so much fun." "Yeah babe... it's wild... It makes me horny." I was in the control room to my newest perverted idea... a Sex Funhouse. I built it in my backyard. It's two floors of perverted sex fun. There are different rooms and fun places to get off sexually......