Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

Sammi's Place in College

by Sissy_Sammi_ on Dec 17, 2017
Transsexuals & Crossdressers

Sammi was up at seven AM, as usual, fully dressed and dolled up and tidying up the suite. Something had broken in her brain at this point, she had been re-wired. Her life had taken some drastic turns, and who she was and what drove her had been completely replaced by something new. Sam, in the past, had been at the helm and would occasionally allow Sammi he...

Stockings & Stalkings Pt. 02

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Part II - An Unwelcome Visitor When Giselle got home she showered immediately, washing away her makeup and scrubbing at the tops of her thighs where Steve had deposited some of his seed. She had seen the whitish-silvery deposit dried on her legs above her stocking tops, which were also stained with semen. She had half a mind to throw them out as she had...

Matt Becomes Mattie Ch. 01

by clarepanties on Sep 11, 2017
Transsexuals & Crossdressers

Part 1 It was 2006, a day in April; I can't remember exactly the first day of the rest of my life begun but begin it certainly did. And for my wife, Joanna, it also meant a massive change. I was back in England from a business trip to Canada, to Vancouver to be precise, and I had been back four days since being over there. It was a business trip but Vanco...

Husband Becomes Helen's Submissive

by Pippa on Sep 18, 2017
Transsexuals & Crossdressers

My name is Philip. I am married to a beautiful woman called Helen, and a few days ago... I did something very stupid! My wife, her mother, her beautician, my P.A. from work, and any of their friends, (in fact, anyone that they choose,) are now completely in control of my life. They are my Mistresses, and I am fully subservient to their every desire. In fac...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

The Good Wife

by komrad1156 on Sep 13, 2017
Transsexuals & Crossdressers

Chapter One "Let's go! Dig deep!" Jason told himself as he passed the nine-mile point. Just one more to go—for today. Running was one of his four biggest passions in life. He also loved his job more than most people. At least he thought that was the case based on the way most people talked about "work." For Jason, work was fun. He couldn't wait to get there...

The Marriage of Martin Hastings Ch. 15

by rik581 on Sep 12, 2017
Transsexuals & Crossdressers

M artin was in stunned silence as he walked hand in hand with Dorothy back to the house, their fingers interlocked. As they reached the house, Dorothy turned to face Martin and then, lowering his lashes, took Martin's hands in his hands and raised them to his lips and kissed them. "Good luck Martin," Dorothy said as he pulled Martin close. He kissed Mar...

Sweet Treat Ch. 04

by SaucyMasquerade on Feb 25, 2019
Transgender & Crossdressers

"Ok, in here is the photographic studio, it may seem a little intimidating to start with, but unfortunately technology can be a little, how you say, unkempt." As I followed him though the white glossed six panel door, I was struck by the contrasting halves of the room. At the far end on the left wall was another door, but centre piece to the room was the la...

Barrack Room Betty Ch. 02

by MicheleNylons on Oct 8, 2019
Transgender & Crossdressers

Chapter Two – Wren Division Ho! The four Leading Recruits were hungover and hungry and in the grey dawn and cold bleak light of day they weren't sure that their prank was really worth it. They entered the cabin and found the four 'Wrens' stood at attention and immediately began to break down in laughter. "Of my fucking god you guys look stupid!" Jean Burge...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...