Crossdresser Bondage Stories

14,958 results
Orientation
Length
Source
Infinite Scroll

Street Hustler Tamed and Trained Ch. 03

by profperverse on Nov 20, 2018
BDSM

BBB (Big Bad Bob) now had my phone number and indicated after our last session I belonged to him. He had called me regularly to discuss the possibility of my continued training. I had to call him at specified times to report to him. The calls always led to a hard cock on my part as he described how a bitchboy slave like me would be trained and rewarded. He...

Fetish Factory

by shawnavinyltv on Feb 25, 2019
Transgender & Crossdressers

I feel this story needs a quick intro. This was inspired by one of the first pieces of erotic fiction I ever read, The Factory by Tr_Veller. It's a similar story, but it's with a genetic girl and not as much sex, still it was an amazing piece. I tried reaching out for permission to basically borrow the idea and take a trans spin on it, but haven't heard back...

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...

Michele Nylons' True Stories Ch. 05

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

Michele and Buster: A Tranny Tale

by MicheleNylons on Sep 14, 2017
Illustrated

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

The Roommate Pt. 13 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Lori left the bed before Leigh Ann woke up from her nap, and Lori again wished she wasn't wearing chastity. If only she could defeat it like before! But having to laboriously dial through 999 combinations on the tiny lock didn't appeal to her (although a hacksaw would probably do the job in a crude way). And so, still horny after the session with her new r...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

My First Crossdresser Pt. 01

by Princess_Rebecca1991 on Nov 26, 2017
Transsexuals & Crossdressers

Tempting, isn't it? Being in a room or just being aware of there are drawers filled with lovely, feminine underwear. The kind of feminine garments you have dreamed of wearing for sometime, your fantasy you've longed to make a reality. How could a pair be noticed missing? There are so many and they wouldn't suspect you, not the straight going masculine male t...