Gloryhole Sissy Stories Asstr Stories

65,212 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Sex Stories on the Internet

by H. Jekyll on Sep 16, 2017
Reviews & Essays

Sex Stories on the Internet: The First Twenty or so Years H. Jekyll February 2, 2008 One might wonder how sex stories grew so quickly on the Internet. Not sex, per se, pictures or videos of amazing acts, but stories, which take enormous time to write and edit, and time to read. And that pay so poorly -- for the most part not at all. Free sex stories have...

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...

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...

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...

A New Adventure... Ch. 02

by johnjinglez1 on Jun 6, 2018
Transsexuals & Crossdressers

This is a continuation of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real. *** After my first three encounters with TS and CD's left me feeling unfulfilled I gave it up for a few months and figured it just wasn't for me; I went back to having sex with...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

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

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...

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...

The Locksmith

by cdbrittany4bbc on Jul 18, 2018
Transsexuals & Crossdressers

I wish to thank thewinedarksea for editing this beast. Summary: Fantasy night goes awry. Let me start off by saying my wife Amy and I have been married eight years now. I must admit our love life has been waning, and sex — when and if we have it — is plain vanilla. Our anniversary weekend was coming up. I told her we needed to do something to reignite our...