Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Undercover Angel Ch. 02

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Tony Leonardo discovered that he had been robbed of two point seven million dollars by Mike Harris at ten o'clock on the 15th July; by then Mike Harris, in the guise of his alter ego, Michele Nylons, was sleeping in a cheap motel a few hundred kilometres away, just over the Victorian border. As soon as he discovered the money was missing from his safe Tony...

Girlfriend Problems

by colleenslittletoy on Sep 13, 2017
BDSM

This story is about a woman humiliating a man. It includes crossdressing and cuckolding. After a heartbreaking divorce I wasted a a few years in mourning, reflecting on all the things that had gone wrong in the relationship. What had started as an equal-sided affair turned into a female dominated one. Basically, her pussy ruled. Finally pulling myself...

Friends, Roommates, and Lovers

by shouldntbeheretoday on Sep 11, 2017
Transsexuals & Crossdressers

Author's note: This story ended up being much longer than I intended. For those of you who like the quick thrill stories, feel free to skim the first two sections before getting to the juicy stuff in section three. For those you who like longer stories, I think you'll find this very enjoyable. New Friends My name is Jamie Morgan. It was mid-January 2012,...

Becoming Cassie Ch. 09

by TGJamie on Sep 25, 2017
Transsexuals & Crossdressers

Only 24 hours had passed since Kate and her friends had left her house for college. When my phone rang, I was eating lunch between classes. "Matt, it's Kate." "Hey Kate, how does it feel being back at school?" "Horrible, I am so jammed up with work. It seems like every professor is rushing to cram as much as they can on us in the last few weeks." "Same h...

A Tale of Slavery

by gunnarsub on Sep 17, 2017
BDSM

Once upon a time there was a straight guy who was known by everybody as a well respected fellow. But he had a secret life. Nobody knew that he dreamt to become a feminized slaveslut, seeking an infinite and irrevocable blackmail relationship with a pitiless Mistress who would be prepared to break him with no way out. He wanted the Mistress to torment him n...

Creating Ginger Ch. 04

by Ms_Allison on Jun 8, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into, cuckoldry, dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consiste...

The Making of a TLB Pt. 04 - Final

by TheMarlboroMan on Oct 22, 2019
Transgender & Crossdressers

I started writing when I got home. The words flowed from me as I took the main female's character through her sexual journey into womanhood. I went into detail dealing with the emotions that were playing within her mind as she was being entered for the first time making sure to mention everything from the pain and discomfort caused by being stretched to the...

Julia, Ben and Lisa Ch. 03

by chloejacobs83 on Mar 2, 2020
Transgender & Crossdressers

Ch 03: WEDNESDAY A few quick notes: 1. this is the third chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned I made it to Julia's house around 9 AM the following morning, timed...

CD Internship Ch. 04 Conf. & Class

by cdtycoon on Mar 24, 2020
Transgender & Crossdressers

All the characters in this story are above 18 by age, so read and enjoy it till I get to the next stage. WEEK-LONG FULLTIME FEMALE On Tuesday; I woke up at 5:00 a.m. and took a nice hot bath to avoid getting myself cold. Then coming out tucking a towel on my chest I look for dad but, he was already out for his walk. So, I went to my room and wore my padded...

Night Of The Horny Femboy

by chlomo on Sep 14, 2020
Erotic Horror

This is an erotic horror story with transgender characters, transformations,mind control, reluctant sex and crossdressing. It also touches on transphobia. It's not meant to represent witches or anything seriously, it's just for fun. I'm Brad, I'm 25 and I work in comic book store, smack bang in the middle of my home town. My life hasn't been the most exciti...