Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

A Girl for a Day

by bigrusker on Sep 12, 2017
Group Sex

It had been a long day. I had showed up late to my first class of the day in my final month of being a college Freshman, tripped coming in the door, and landed right at my calculus professors feet. Naturally, not a single person missed the incident, or my professor sarcastically suggesting I would see better from a chair. And that was just the start. After...

Life and Time of Lady Vargos Ch. 08

by rik581 on Mar 26, 2019
Transgender & Crossdressers

"Lies, Truth, and Innuendo" Martin was pressed into attending to his duties that week as Lady Vargos. With little or no manly pride left to swallow or cling to, he performed his daily routines dressed as a woman, both publicly and privately. Each day seemed to bring more heart felt shame and humiliation into his life as he stepped out and displayed his ema...

Female Erotic Police Squad Pt. 03

by mattpantyhose on Sep 14, 2017
Fetish

Most of the officers of Female Erotic Police Squad enlist in the service to catch criminals. But there are also some who do it for sex. Physical love is the modern way to fight crime, but it does not necessarily mean that sex should be considered merely a tool. As long as an officer fulfilled her duties properly there was no reason for her not to take additi...

Constrained in Corsetry

by susanxdresser on Sep 16, 2017
Transsexuals & Crossdressers

Although I am not into serious bondage I love the erotic pleasures of wearing corsetry and other tight feminine garments next to my skin. When wearing suspenders and stockings I love the erotic sensation from the tightness of the top of my stockings gripping my thighs and the suspenders brushing against my thighs as I walk, as I envisage my suspender belt an...

April Fool Office Sissy

by lululuvsblack on Apr 10, 2018
Transsexuals & Crossdressers

"Dear Colleagues This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and tie...

The List

by Futaba on Nov 20, 2018
Transgender & Crossdressers

-Prologue My family was in shambles, we lost all the employees in our mansions and properties and we were forced to live in a normal house without anyone to take care of the garden or miscellaneous stuff. Father left us for another woman as Mother couldn't control him well and let him cheat on her all the time. We were on the brink of going bankrupt becau...

A Taste of Strawberry Ch. 03

by katunda on Sep 16, 2017
Transsexuals & Crossdressers

Part 3: A Taste of Contentment If you haven't read the first two parts of this story, you might be interested as they set up the background for this one. But if you're only interested in the transsexual aspect, start here. Background:A twenty-eight year old woman named Alyssa has been dumped by her boyfriend, Matt. After almost three months of depression...

Mistress Chantel, Tranny Dominatrix Ch. 12-13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twelve: Another Play Day Work Day at Our Studio. I arrive at my studio dressed for another day of fun and exciting dominatrix work. I park my "Plum Crazy Girl." step out in my red leather thigh high boots over my black sheer pantyhose. On my feminine looking body is a red leather form fitted mini dress with loose pleated, A-line skirt barely coverin...

Fun with a Cherry Popper

by Floydman1 on Jul 2, 2018
Transsexuals & Crossdressers

Quitting time couldn't come fast enough. As soon as I had seen the notification of delivery, I couldn't concentrate on anything but what was inside the box, waiting for me at home. Finally! I was legal as I drove home, but barely. I had just managed to duck a conversation that was guaranteed to take at least an extra fifteen minutes. While I didn't brazenly...

Working for Halloween Ch. 02

by shawnavinyltv on Sep 18, 2017
Transsexuals & Crossdressers

As I hung up the phone, I shook my head and wondered what I was thinking. It was just a few days after my "outing" (quite literally!) at the costume store, and here I was agreeing to go again. Sure, I'd enjoyed the hell out of it. Both the dressing, and the, uh... extracurricular activities with Brad afterwards, but I couldn't keep pretending to be a girl....