Gay Crossdressing Stories

23,246 results
Orientation
Length
Source
Infinite Scroll

Ioan Gruffudd Ch. 01

by madam_noe on Sep 12, 2017
Celebrities & Fan Fiction

I turned twenty eight and no one noticed. When I awoke it was six a.m. Greenwich Mean Time, and no one had called. It was midnight back home and so I didn't expect any calls until late in my evening. But no calls came from my few friends in London that knew it was my birthday. I was lonely, and low on prospects. My two closest friends and I were going out...

Zelda

by jjcolejr on Sep 16, 2017
Romance

My family and I were at a bar in Sturgis when a fight broke out. My family may have started it. The fight was with another family that was amazingly arrogant and all had expected it would come to this since our first trip to Sturgis. They had made it obvious we were not welcome. It was puzzling because our families looked like mirror images of each other, o...

Kelly's Liberation Ch. 03

by aussie_101 on Sep 17, 2017
Exhibitionist & Voyeur

After I sent my nude pictures anonymously to Libby, and then confessing my ruse and speaking with her on the phone, and then posting a strip-teasing series of my own on the public boards at Literotica, and losing control with Libby as I did so and degenerating into some of the best (and most confusing) phone sex ever had in the history of the phone -- after...

The Woman Inside

by ErikKramer on Sep 12, 2017
Transsexuals & Crossdressers

This is my second submission but one of the first stories I've written. This one has a happy ending and I hope you enjoy. Any and all feedback welcome. * Walter sat at his usual seat at the end of the bar. From here, he could scan the entire lounge. Tonight, it was busy with the dance floor crowded. The woman sitting alone drew his attention. She had caug...

A Little Bit Deeper Now Ch. 01

by TheWorldSpins on Sep 19, 2017
Loving Wives

Author's Note: I'm putting this one in Loving Wives, but be warned this story contains significant blackmail/NC/reluctance themes. I'm going for dark, direct, and dirty here, since I'm simultaneously writing a romantic series and enjoy the change of pace. This chapter is fairly short, but sets up a multi-part series. All characters are 18+, all rights reserv...

Stolen Week

by ladyroxanne21 on Sep 16, 2017
First Time

I am 30 years old, and still a virgin. This fact increasingly makes me want to cry. Knowing that I was not a looker, I have spent my life going to school and getting a good career. I'm a nurse, and I work 60 hours a week on average. Makes it kinda hard to get laid, huh? Now that I have attained a certain amount of seniority at the hospital where I work, I a...

Michele And The Predator

by MicheleNylons on Jul 15, 2020
Transgender & Crossdressers

The predator peered through the bedroom window and smiled; he couldn't believe his luck. This woman was just to his taste; he felt himself begin to stiffen as his eyes devoured her; he couldn't wait until he had his hands on her. In his mind he played out the scenario that he envisaged would soon take place. His thickening member began to engorge and throb....

Indian Male Bisexuality

by Samuelx on Nov 18, 2019
Group Sex

"Imran, you should have been honest with me," Pooja Bawa said, looking somewhat reproachfully at her husband of twenty years. Imran Sheikh took a deep breath and looked at Pooja, the lovely woman who'd shared his life and his bed for more than two decades. He'd been in love with her ever since they met at Chandigarh University in the Mohali District of Punja...

Vivian Laaning Ch. 42

by Bodington on May 22, 2019
Novels and Novellas

The next morning Vivian was the first to wake up. She was on her side nuzzled up against Ralph's side, who was sleeping on his back. Half of Angela's front was curled up on top of Ralph's front, and she was snoring slightly; very lady like. When the cobwebs cleared from her eyes, Vivian spotted Ralph's penis ever so innocently dangling from its base. The tho...

Implanted

by The_Technician on Jul 14, 2020
Sci-Fi & Fantasy

This is a story in three parts, all of which are in this post. It starts rather slowly as it follows Donna Reynolds and her decision to be implanted so that she can be successful in the world. It is rather mild sexually, but somewhat upsetting in theme as it sets forth a fictional future world that may be less improbable than some would think. In fact, we ma...