Mature Gloryhole Stories

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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...

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...

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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A Steeler visits Charleroi, PA

by BuckJones0001 on Sep 2, 2017
First Time

Victor Strelsky at 26 had reached his dream of being drafted by the Pittsburgh Steelers. His dad had begun promoting his football abilities in the eighth grade. He had a gift. He found the ball and the ball found him. Victor sailed through high school into college on his athletic abilities. Turning pro was the natural step in Victor's career. There was just...

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...

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......

The Pump House

by AlinaX on May 11, 2020
Fetish

Inspired by an idea by enigma3 in the Forum. * They say size doesn't matter, but when you are - whether by length or girth - within the smallest five percent of the population, it's difficult not to feel self-conscious about it. It's difficult to talk to women without imagining their horror, their amusement, their mockery, their contempt. Easier to avoid r...