Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

The Epidemic

by Nils Huim on Feb 7, 2018
Transsexuals & Crossdressers

Saturday David and Karl were necking on Karl's six-cushion couch. Karl was wearing a pair of his wife Bridgette's lace panties but was otherwise naked. He had a somewhat stout middle-aged build with a barrel chest. His body was unshaved. Up top his dyed-brown hair was thinning. He hadn't shaved that morning, giving his tongue-in passion an outward scratchy...

Prom? Ch. 01

by New_Girl_ on Mar 27, 2019
Transgender & Crossdressers

Hello everyone, this is my first story I've ever written and posted on here! I hope you like it. If you do like it, be sure to vote and comment so I know you want to read the next part! ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ My legs shook as I powered my bike up the hill. I knew I had to get to Natalie's house as soon as I could. A few minutes before I...

Arabian Nights Pt. 06

by MicheleNylons on Sep 26, 2017
Transsexuals & Crossdressers

Michele sat sobbing as she told Sarina about being taken forcibly by Jamhal, the Cabal's vicious pimp. She told Sarina how Jamhal had justified his actions because Michele was no longer unsullied. "Sullied, unsullied - it means nothing to the Cabal. You are their property and it is forbidden for anyone to touch you other than the Cabal or those they have g...

Martin's Halloween Nightmare

by rik581 on Sep 16, 2017
Transsexuals & Crossdressers

Martin's Halloween Nightmare is a short side story using the characters and world of Martin Hastings. An unusual story to say the least. Not for the squeamish. It is not part of the saga itself. ***** "Twisted" Martin sat at the table before the judge with his legal counsel. The courtroom was full of spectators as the drama of the judge's decision loomed...

Jacki's Journey into Sissyhood Pt. 02

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is a continuation of: Jacki's Journey Into Sissyhood. Thank you for reading a continuation of that series. ***** I awoke as sunlight began to creep into my bedroom. I might have thought last night was a dream if it wasn't for the large hairy arm draped across my shoulders and the large cock poking at my backside. I tried to slowly slide out from unde...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

How I Became a Sissy Slave

by Sissy_Sasha on Jul 27, 2020
Transgender & Crossdressers

I had never been so embarrassed in my life. The woman in front of me looked at me with disgust that burgeoned on fear. Seconds prior, I was knocking on her door and ringing her doorbell expecting for a man to answer. This man was Anthony, or at least that's the name he'd given me when I asked. We'd met online a couple weeks ago on a gay dating site. For a...

So You Want to be a Nurse? Ch. 01

by MicheleNylons on Sep 18, 2017
Transsexuals & Crossdressers

Bound to Her Calling Males make up around 10 percent of the nursing workforce in the UK. Nurses are typically regarded as female and males in nursing can find themselves referred to by the public and patients as 'male nurses' or 'murse' to distinguish them from other nurses. After the Second World War, large numbers of male nurses moved into the work force...

Lady In The House Ch. 05

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

From Part IV Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread there when he had pressed his body against me. I watched the terrible storm brood in his eyes as he reached out and smashed me across the face....

Prom? Ch. 05

by New_Girl_ on Sep 25, 2017
Transsexuals & Crossdressers

Hey everyone, Chapter 5 is here! Be sure to read the previous chapters beforehand. If you liked the story, feel free to leave me a comment or a rating. Thank you! ~~~~~~~~~~~ I woke up in Mike's bed, naked, his arm wrapped around me. I turned my head and saw that the alarm clock now read 7:52, giving us a grand total sleeping time of less than 2 hours. Th...