Crossdresser Bondage Stories

14,958 results
Orientation
Length
Source
Infinite Scroll

Life and Time of Lady Vargos Ch. 01

by rik581 on Oct 3, 2018
Transsexuals & Crossdressers

I am in the process of reposting my stories. *** "The Life and Times of Lady Vargos" is the second book of the Martin Hastings adventures into a life of forced feminization. This story follows the feminization and marriage of a reluctant young man as he is forced to accept his fate as a male/bride, in a same sex marriage, arranged by his family. This stor...

I'm in a story??

by blank97 on Jul 25, 2020
Science Fiction

Disclaimer: I got the inspiration to write this story while I was reading a story by anonenffan titled “Kim’s crazy theory” which is apparently (I found out about this after writing this) inspired by Jappio's "Amy Stuck in an ENF Story".{if crush==0}{else} Customize: Use the customize option to change characters name. Changing "Reader's name&q...

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A Crossdresser's Night In The Park

by cdtiffanymd on Oct 5, 2020
Transgender & Crossdressers

A Crossdresser's Night in the Park cd, bdsm, con, mm, anal, oral, toy Last night I was online in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with...

Sissy Walk of Shame

by zona_loser on Mar 12, 2019
Transgender & Crossdressers

First off: This is a story about my alter ego a not so bright crossdresser who likes a bit of exposure. It also contains an element of self-bondage but not in the traditional manner. All characters are over 18 years of age and are purely a figment of my imagination. ***** I am a part time mostly closet crossdresser. I don't consider myself gay or bi and ha...

Bondage Doctor

by spandexman on Sep 2, 2017
Fetish

Another city, another business meeting. I decided to stay an extra day or two, after all I deserved it, plus no one knew me in this small out of the way spot. I checked into a motel on the outskirts of the city, a sleazy one. The room was everything I wanted, tacky green wallpaper, a big queen sized bed, tiny bathroom complete with a full length mirror, a c...

Sissy in The Hart of the Valley

by EvelynT on Sep 16, 2017
Transsexuals & Crossdressers

The story so far; having completed the first date with Harold Plumrose and with over a month until the scheduled second date Sissy Betty Blane spends time at a t-girl club with Cindy. ***** When I got home from the Hollywood Hills I barely had the strength to remove my makeup. I was so exhausted I just wanted to flop on the bed and pass out, but I persever...

The Club of Fools Ch. 05

by sublocked on Sep 19, 2017
Transsexuals & Crossdressers

Author's Notes as before: (1) This is fiction; (2) Do not read this chapter out of context. Read chapters 1-4; (3) Jason is a masochist; (4) Victoria is a sadist and possibly a psychopath, her actions illegal; (5) Do NOT ever attempt "breath play" as it is described herein; (6) Do NOT ever leave anyone in bondage as severe as this for as long as this a...

Sarah Dressed and Visits a Sex Club

by SarahCD on Dec 25, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ------------------------------------------------------- My wife was away visiting her family and so I decided to have an adventure....

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...