Crossdressing Bondage Stories

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Secret Lives Pt. 01

by WildDaisy85 on Dec 12, 2017
Transsexuals & Crossdressers

This story is completely fictional. All characters are willing participants in all activities and similarities between other fictional characters is unintentional. I hope you enjoy the story and welcome all feedback. This is my first time writing so expect there to be a few mistakes. Thanks and I hope you enjoy reading this story as much as I did writing...

Secret Lives Pt. 02

by WildDaisy85 on Dec 16, 2017
Transsexuals & Crossdressers

This is a continuation to Secret Lives Pt 1. I highly suggest reading that first as it sets the stage for this. As requested by a reader on Pt 1, I have combined two chapters into this one to provide more length. I appreciate the feedback and please keep it coming. *********** I laid in my bed, dressed in women's lingerie and completely bound, as my siste...

Almost Damsel Almost in Distress

by shawnavinyltv on Jun 19, 2018
Transsexuals & Crossdressers

Finally! I had the day off from work and I planned to spend it indulging two of my favorite activities... crossdressing and self-bondage! I've been dressing since I was 10 years old, and about the only thing that was more exciting than getting all femmed up... was locking myself into some strict bondage and struggling to get free! I lived in a small apartme...

Slave Ch. 09

by slaveheathen on Sep 25, 2017
Fetish

SLAVE Note: This is about a bisexual submissive man and his journey as he explores his sexuality. I put it in the fetish section because that seems to be the best fit. There is piss and scat. There is bondage and crossdressing. There is fisting. There is group, gay and bisexual sex. There is non-consensual and reluctant sex. There are even elements of reali...

Swipe Right Ch. 02

by amb_anonymous on Jul 23, 2018
Transsexuals & Crossdressers

If you haven't read part 1, I'd recommend it since that is the start of the transformation, but this story could pretty much stand on its own. This story contains interracial, dom/sub, t-girls, crossdressing/sissification and bondage. This story is fantasy. I like to stretch the limits of what's possible, so don't expect pure realism. For clarity: In m...

Cocksucker: Crossdressing

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Straight man is forced to cross dress and suck cock. You do not need to read the first parts to enjoy this story about a straight man crossdressing in San Francisco. In case you are curious about how he ended up in this situation here is a brief summary of the first two parts of the "Cocksucker" series: Chris, a married straight man, is stuck at t...

Master's Degree in Crossdressing Ch. 02

by wifetoy on Sep 16, 2017
Transsexuals & Crossdressers

This confession is the second chapter of a follow up series to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making those confessions to the public for the first tim...

Fair Is Fair Ch. 04

by bgdddy_2000 on Sep 18, 2017
Transsexuals & Crossdressers

This is a story about crossdressing and bi sexual experience involving male on male contact. If you don't enjoy this kind of story, why would you read it? ***** His cock hit the back of my throat as he held my head, getting ready to fuck my mouth. I would have gagged, had I not had so much practice sucking cock recently. I relaxed my throat and let his coc...

Swipe Right Ch. 03

by amb_anonymous on Jul 30, 2018
Transsexuals & Crossdressers

This story contains interracial, dom/sub, t-girls, crossdressing/sissification, impregnation and bondage. This story is fantasy. I like to stretch the limits of what's possible, so don't expect pure realism. For clarity: In my story, a t-girl is someone with a completely female appearance, but with male sex organs (so no hermaphrodites in the story). In...

My Story of Degradation Ch. 02

by Philippasubmaid on Sep 5, 2018
Transsexuals & Crossdressers

This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please. As I sat there sipping my coffee, I thought about our brief email exchanges, I still knew nothing about her, and I realised that I was very nervous, how should I address her, was I goin...