Sissy Gloryhole Stories

6,957 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

Open in Reader

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...

Gloryhole First Timer

by SluttyChrissy on Oct 5, 2020
Transgender & Crossdressers

This is a true story of an experience I had a few years back. I hope you enjoy! It all started on a random Thursday on my lunch hour. I was feeling especially girly that day and I decided to make a detour to my favorite little adult bookstore/lingerie store. I walked in and slowly browsed around, looking at the lingerie and dresses, just enjoying the feel...

Finally a Real Sissy

by Parasissy on May 7, 2019
Transgender & Crossdressers

I have to tell you about the experience I had with my wife the other night. But first a little background for context. I have been married to my wife for over 10 years, I told her a little about my "adventurous" side before we got married, and I've slowly revealed more as time has passed. She tries to accommodate my Sissy desires, but truthfully she is not...

Sissy Slave

by mikedoreilly1973 on Nov 24, 2018
Fetish

It was late friday night, and Mike had just gotten home from work, he was tired and filthy from work and decided to take a much needed shower, he went to the bathroom and noticed the door was slightly ajar, he peeked inside and saw his 18 year old daughter Samantha taking a shower. Samantha was his daughter from his previous marriage which had ended badly wh...

Open in Reader

Dickgirl Tyranny

by Lusc on Mar 28, 2018
Transsexual

In this medieval/victorian fantasy world, the physical differences between men and women(also known as dickgirls) are enormous. In comparison to their male counterparts, women are taller, stronger, and better endowed. On top of all this, a dickgirl's cum has a strange drug-like effect on males. This effect's severity is mild when applied to the skin, stronge...

Open in Reader

Glory Hole

by GateKeeper_A on Jun 11, 2014
Group Sex

Last month, you had discovered that your local adult novelty store had a glory hole. Since that day, that glory hole has been all you can think about. Every time you close your eyes, you picture a cock sliding through a hole towards you. Every time you masturbate, your mind is filled with fantasies of strange men's cocks. You shudder with a mixture of trepid...

Open in Reader

The Sissy in the Loft

by Sissy_Sammi_ on Dec 31, 2018
Transgender & Crossdressers

*All characters are 18+ *** James grit his teeth and walked through the door, a bell ringing as he entered the store. It was getting late and the sun was setting outside. He had been waiting in his car for nearly 20 minutes, waiting for people to leave the shop and no longer be near the store. The lady running the shop looks at him with a strange look fro...

Story of a Sissy Cuckold

by HughJanus on Oct 24, 2019
Fetish

Hi there, my names Michael but everyone just calls me Mike, i'm a 46 year old guy, i was an average guy living an average life, married to the love of my life, her name is Samantha. Shes my high school sweetheart, we dated all through high school then when we graduated we got married. She still has a smoking hot body, even all these years later, she works ou...

Open in Reader

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...