Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

Hotel Panty Slave Pt. 02

by hotelpantyslave on Sep 16, 2017
BDSM

If you haven't read the first installment, please do. We start here with me trapped in my hotel room by two maids turned mistresses, crossdressed, gagged, cock-caged and without my clothes. They did leave a note taped to the back of the door telling me to pee; drink the sports drink on the bathroom counter by plugging the straw into the hole in the penis g...

Ashleigh: Lost & Found

by DC8 on Sep 13, 2017
Romance

The roaring in my ears receded to a dull ring as I stepped out of the bar. The giant behind the drum set was still playing some farewell filler, while the rest of the band finished their beers. I turned to see Tim furtively exchanging phone numbers and sloppy kisses with a bovine woman at least twice his age. I grabbed him by the arm and started steering him...

Lynne Takes Revenge

by Morpheuse on Sep 17, 2017
Loving Wives

I'm enslaved by my wife and her lover. What can I do? What do I want to do? Lynne decided she should learn to drive about five months ago. We're both in our late twenties and I was very encouraging. That would mean we could share the driving, always a benefit on long trips and maybe even the chance of a glass of wine for me on a night out. She asked around...

Adventure on CL

by Pantyhoseheels on Apr 14, 2020
Transgender & Crossdressers

This is a mostly true story of the first time I revealed my secret side to another person. My name is Colleen, secretly. I have crossdressed most of my life. It has always been my little secret. But as with most people, I have had the desire to try being with someone else, and to share my secret. I began to occasionally check Craigslist, looking for that...

Life and Time of Lady Vargos Ch. 06

by rik581 on Mar 27, 2019
Transgender & Crossdressers

Chapter 6 "Lady of the House" Martin had been home three days from his visit to the spa, and things were now becoming a bit more of daily routine for him as mistress of the household. As usual he had been awakened early by his husband with a long passionate kiss on the lips. Martin grabbed the sheets with both hands and groaned as he awoke in the affectio...

Life and Time of Lady Vargos Ch. 15

by rik581 on May 15, 2019
Transgender & Crossdressers

Chapter 15 "Victim or Slut" The process started the next morning without Martin needing to lift a finger. Leanne had done as she had promised the day before and she set his now platinum blond hair in 1 1/2" brush curlers, that he would wear for the day. As usual the rows were perfectly straight with the two pink pins holding each curler tightly in place. L...

Life and Time of Lady Vargos Ch. 18

by rik581 on May 21, 2019
Transgender & Crossdressers

Chapter 18 "Changes upon Changes" Martin rolled over on his side hugging his pillow trying desperately to fall asleep. Though the curlers that Leanne had tightly wound in his hair for the night were very uncomfortable and trying to position his head to sleep in them was exhausting, it was the events of the day weighed heavily on his mind and kept him awake...

The Mixer

by dysfunctionaldreams on Sep 16, 2017
Transsexuals & Crossdressers

The night was going to be interesting. I was in the basement with all my fraternity brothers and we were all dressed as girls. The theme of the mixer we had agreed to was a crossdressed mixer with one of the local sororities. They had some of the hottest girls on campus, so to throw an element of sexuality into a theme was not a bad plan. I had gone over to...

My New Daddy Ch. 04

by sissytoy20 on Mar 6, 2018
Transsexuals & Crossdressers

I got out of the shower Saturday morning, my cock hard as a rock in its cage. I loved how it bobbled on my crotch like a piece of jewelry. That was all my cock was now - a decoration. My asspussy was my real sex organ and I hoped it would get a hard workout today. I dried my cage and put my butt plug back into my freshly washed ass. It slipped in easily thi...

Life and Time of Lady Vargos Ch. 19

by rik581 on May 21, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Martin stared out the car window as he was driven to meet Darren once again. He was in the back seat of a different car than the first trip and it was no limo by any means. Martin's thoughts were swirling around things he was beginning to notice. He was being allowed out w...