Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Casey's Submissive Journey Pt. 05

by corduroysissy on Feb 7, 2018
Transsexuals & Crossdressers

Homo Hubby Night – Part One Note: In this continuing saga, Casey (Debbie) & Jamie (Angie) are closet crossdressers who are submissive to their wives Karen & Audrey (respectively), however in this section of the story there is no cross-dressing. Their wives are humiliating them by making the boys put on a homosexual sex show for their amusement. *...

Ian's New Job Ch. 02

by SatinSlip on Dec 10, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex, crossdressing, and humiliation. ********** Wendy wore the shortest skirt she owned. A blue, pleated thing that stopped a few inches short of her knees. Underneath she wore red lace panties Ian had bought her for valentines a couple years ago, an...

The Role Players Pt. 04

by hollygurl29 on Jul 30, 2018
Transsexuals & Crossdressers

DISCLAIMER: This is a work of fiction and all characters represented here and in any additional parts of this story are all over the age of 21. This tale involved crossdressing, bdsm & role playing. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy. The main characters in this tale are as...

Almost Damsel Almost in Distress Ch. 02

by shawnavinyltv on Apr 23, 2019
Transgender & Crossdressers

I woke up sweaty and a bit confused. I was also having a bit of trouble breathing. I realized I was still wearing my heavy duty corset. I also realized there was someone snuggled up against me! Suddenly visions of last night's self-bondage session came back to me and I remembered Alex, my neighbor, had spent the night. I had a momentary surge of excitement...

Prom Queen

by komrad1156 on Sep 23, 2019
Transgender & Crossdressers

*Author's Note: I shared my own very unique love story in Serendipity. I got into crossdressing late in life compared to most guys who start somewhere between 5-15. I was married, and had been on active duty for four years and was totally into weightlifting since my sophomore year of high school. When I first tried wearing women's clothes, I was in my early...

Unearthed Desires

by ScumDumpster69 on Mar 2, 2020
Transgender & Crossdressers

Author's note: This story contains dickgirl on female action, as well as cuckolding, cheating and humiliation. HOWEVER, even if you don't like that kind of stuff and prefer male bottoms, you might like this one. At least if you stick around for chapter 2 ;) ***** "She's so amazing! She never takes any shit from customers!" Staring out of the café window,...

Serendipity

by komrad1156 on Sep 13, 2017
Transsexuals & Crossdressers

*Note to readers: I recently wrote about a cruise I went on in the Fall of 2012with my former boyfriend, Tim. I wrote it in response to the many private emails I got asking me why I don't live full-time as a woman. The short answer is: I don't want to because I enjoy being a man. I only want to be Callie a few hours at a time. Tim and I broke up shortly aft...

New Perspectives

by bart_allen on May 30, 2018
Transsexuals & Crossdressers

*** This story contains non-consensual gender conversion, LGBT themes, slurs, and things that can cause dysphoria *** ***** Have you ever noticed how many horrible people have a very unassuming, normal as can be name? It can make it difficult to tell them apart from the good people. Thankfully, a person's actions are tied to their name. That's how most peo...

Changeling Ch. 03

by Michael142 on Sep 19, 2017
Fetish

A very fateful decision. Continued from the end of Chapter 02 - Donna and David after a night at the club: "How was it, to feel another man's hands on you ... and in you?" I lowered my eyes and said softly, almost inaudibly, "It felt wonderful David. It felt wonderful to have another man touching me!" We lie together not moving and not talking for...

Obedient Delicious Submission

by Jamie_in_dresses on Sep 25, 2017
Transsexuals & Crossdressers

We had been married for four years when my wife took on a new job, she was going to be the manager of a new insurance brokerage in our town but had to spend a few weeks of orientation and training at head office 180 miles away before she took on the responsibility. She spent the weeknights with an old university friend and would come home each Friday evening...