Sissy Glory Hole Stories

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Becoming a Sissy Maid & Slut Vol. 04

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Preview: Here is another chapter of my multi-part "Becoming a Sissy Maid & Slut Story." I so hope you all are enjoying this story. I'm no professional writer so excuse me for any writing errors. But I have a flood of sissy maid, slut, crossdressing ideas, thoughts and fantasies to share. I will add more chapters to this unfolding multi-part story now ONE cha...

Exposed as a Sissy Cuckold

by lapitup65 on Sep 18, 2017
Loving Wives

Last Friday we had a date scheduled. We were going out to dinner to meet Jay and we had a room booked at a nice hotel. Mandy and I checked in early. We relaxed for a while, sipping a glass of wine before Mandy headed off to take a bath and start getting ready. Just as Mandy settled into the tub, Jay sent her a text. I didn't read the text, I just took her ph...

Brad's Adventure

by nancyvasquez on Aug 28, 2018
Transsexuals & Crossdressers

Brad was restless. He woke up with a raging hard on. He cast a glance over at his wife. She was on her side, snoring. He knew better than to wake her up. He got out of bed and went into the living room and began watching shemale porn on his laptop. Brad loved shemale porn. Most of the T-Girls incorporated the physical appearance of females, but with the sham...

Stroke Slut: Goddess' Cuckold

by StrokeSlut on Oct 19, 2020
BDSM

"Well don't just stand there drooling on the doormat, come on in." The black hood had come off Stroke-Slut's head, the sudden burst of sunlight that hit his eyes was nothing compared to the radiant beauty that stood before him. Despite hours of jacking off to her on the internet, not the mention their previous sessions, he never seized to be amazed at the si...

Becoming a Sissy Maid & Slut Vol. 05

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Prefix: A continuation of my sissy maid and slut journey. I hope you all do enjoy my unfolding story here. I am writing further chapters with hopes to give you all a semblance of some of my sissy ideas and thoughts so that these may excite you as the reader. I will try hard to keep each chapter on an exciting flow of what I feel may be life of a full time si...

Chrissy's Trip

by Ide32 on Sep 16, 2017
Transsexuals & Crossdressers

Part 1: Trouble in Paradise It has been seven months since Chrissy and Miriam had their memorable first date, and things are going well. Every night Miriam is in town she falls asleep with her giant futahood buried in Chrissy's cum filled ass, and most every night she is away Chrissy heads to Futanari Palace to sate his hunger for cock and hot futa juice....

A Freshman's Summer Class Ch. 07

by CapnSteelBoy on Jun 1, 2020
Transgender & Crossdressers

A Freshman's Summer Class **All characters are of legal age for adult content.** We Continue from where we left off with our brave hero, as his adventure continues during his summer of higher education learning! This is a continuing series I'll be releasing as my busy editor(s) help me clean up my keystrokes of mess.. Much thanks goes out to them, as th...

The Sweetest Husband in the World

by donaldelliott11 on Sep 15, 2017
Loving Wives

My husband, Sandy, is one of the nicest people on Earth. He doesn't have a single enemy. He cheerfully helps anyone he knows, anytime he is asked. His basement workshop has always been a friendly neighborhood hangout for the other husbands on our street. Sandy is also a failure at everything, including our marriage. He has no particular talents, never learn...

Quenching Thirst Ch. 02

by PutItInMyMouth420 on Jul 10, 2018
Transsexuals & Crossdressers

So there I was covered in Black mans jizz and piss, handcuffed to a handrail in a gay strip club. I was hard as a rock at this point and had realized in the midst of my humiliation that the sexiest part of all of this degrading shit was my lust for Mr. Warden. I wanted to know how it felt to truly give myself to a real man. Even though my ass was virgin, i w...

Seducing Kevin Ch. 01

by Spango on Dec 2, 2019
Transgender & Crossdressers

(This story is a follow up to my story 'Pizza Delivery') *** Dear Internet, It had been a few weeks since my encounter with, as I like to call him, Pizza Daddy and I was looking for a new adventure. I briefly thought about cruising the local parks at night or finding a glory hole somewhere (giving, not receiving, of course) but Pizza Daddy's warning about...