Sissy Gloryhole Stories

6,957 results
Orientation
Length
Source
Infinite Scroll

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...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

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....

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...

HypnoSissy: Cum Cravings

by silkstockingslover on Sep 26, 2017
Fetish

Summary: Videos entrench his hunger for cock and cum. Note 1: Thanks to hfernandez1983 for the story idea and the intriguing revelation that hypno sissy videos exist. Note 2: Of course, all participants are at least 18-years-old. Note 3: Thanks to TexBeethoven, Robert, and Wayne for editing this chapter. Apology: This part was originally announced as bei...

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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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...