Crossdressers Stories

12,121 results
Orientation
Length
Source
Infinite Scroll

Busted Wearing Panties Ch. 02

by tonyl65 on Sep 18, 2017
Transsexuals & Crossdressers

I can't believe I am walking down the hall, wearing a black leather corset with matching panties, after my step daughter just fucked me in the ass with a dildo. I entered my bathroom, turned on the hot water in the shower, and slowly stripped out of my sexy clothes. I stepped into the shower and soaped my body down. I poured liquid soap in my hand and rubbe...

Consent Ch. 13

by sublocked on Sep 18, 2017
Transsexuals & Crossdressers

Author's Notes: (1) Well, I'm back. I had surgery and the cancer is believed to be gone. My recovery is nothing short of miraculous, as I have resumed all my usual physical activities, pushing very hard to overcome residual pain from the surgery. Now to get my mind and fantasies working again. (2) I had to re-read my previous chapters in order to remember...

Anal Addiction Ch. 02

by Tallnhard1 on Sep 18, 2017
Transsexuals & Crossdressers

This story contains sex between a transsexual top and a male bottom. If you do not like stories where a man gets fucked by a transsexual please stop reading. ____________ I had been pacing back and forth for about ten minutes before I finally sat down on the couch. Looking at the phone in my hand I considered the call I was about to make. I should have kno...

A Sister's Revenge Ch. 01

by Johnboy9 on Sep 18, 2017
Transsexuals & Crossdressers

This is a revised version of the "Sister's Revenge" story. I am only doing this because in coming back to this site after so many years away, after having originally written the first series, I feel my story-telling has gotten much better, at least in my ability to write it down, and much less cruel, as the way I feel about my life has become more peaceful a...

Coach Daddy Ch. 07

by whatcouldofbeen on Sep 25, 2017
Transsexuals & Crossdressers

It has been several glorious weeks since my gender and in essence , my life, changed. Who was once an awkward bean pole of a young man, was now a confident budding woman. It all started when my boss, Coach Zek, noticed my preoccupation with all the huge men I was now constantly surrounded by. He also noticed that I wore a bra. I'm sure at first he thought I...

A Sister's Revenge Ch. 06

by Johnboy9 on Sep 18, 2017
Transsexuals & Crossdressers

I hope you all enjoy this next installment to the "A Sister's Revenge" story. I appreciate any feedback you care to send, and will respond to all who desire it. I really do appreciate any and all notes and letters received from readers of this site. Yes to those who wondered, I did have an idea of where I wanted to go after Michael's next turn at fainting,...

A College Sissy Ch. 01

by nat_rose on Sep 26, 2017
Transsexuals & Crossdressers

For some reason I decided to go away to college. Like, a plane ride away from home. I guess part of me thought it would be good to separate myself from high school and my friends and family and start to explore who I really am. That's what college is all about, right? So after all was said and done, I decided to accept an admissions offer from a big state s...

Shortening His Sentence

by SugarandSalt on Sep 11, 2017
Transsexuals & Crossdressers

The shemale on male sex you've become accustomed to from me takes a bit of time to build to, but if your mind is a little warped and your cock a lot hard by the end of this story, Sugar's done right by you. ;) * Foster didn't know what to expect as he opened the door. Foster entered the warden's office with more than his fair share of trepidation. She didn...

Love with a Twist Ch. 07

by Lostinmich on Sep 25, 2017
Transsexuals & Crossdressers

Hello Readers. First thank you to everyone that has left me feedback or comments, I appreciate and read everyone you send. Comments are always welcome as it drives me to keep writing. To everyone that has voted, thank you as well. To my Editor: As always you Rock! Cristal Ball is an amazing person with very amazing skills, with out her this would never h...

A Lost Bet Ch. 02

by amarasfantasy on Sep 12, 2017
Transsexuals & Crossdressers

It was a fitful night. While the chair had been designed to provide at least a little comfort, having my arms bound behind me all night got to be uncomfortable. Plus, I was forced to remain in the same position because of being bound to the chair. And it didn't help that every so often, I had a machine pumping in and out of my ass. I slept intermittently, bu...