Crossdressing Bondage Stories

15,183 results
Orientation
Length
Source
Infinite Scroll

An Ever Changing Story

by Helenthemaid on Sep 16, 2017
Transsexuals & Crossdressers

Caught Out and Permanently Punished I was wearing a ultra short black leather mini skirt, a tight leopard print low cut top, which revealed my cleavage entrapped by my pink lacy bra (with matching panties). The straps of my 6 inch leopard stiletto heels were securely padlocked around my ankles. Recently I had been often going to the local park dressed in...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

Open in Reader

Changes Ch. 02

by sublocked on Sep 25, 2017
Transsexuals & Crossdressers

Notes to Reader: (1) A lot of this is fiction; much is fact. (2) Cross dressing in marriage is a difficult situation; acceptance of it comprises three entities: husband, wife, couple. (3) Nobody CHOOSES to be a cross dresser, so please don't demean yourself (the reader) by macho dismissal and criticism. Lawyers, plumbers, truckers: anyone can be one. Most...

New planets new experiences

by latexdoll on Sep 26, 2017
Science Fiction

The little blue screen lights up as the video begins, the audio being transmitted directly to your audio implant. "We thank you for choosing Stellar Gold, the finest shuttle service, now with service to all 7 connected Galaxies with 2 more scheduled by 2475. Please enjoy this 10 minute video." The year is 2469 humanity has known that they are not t...

Open in Reader

Myra and Jack in Toyland

by ValoryG on Sep 11, 2018
Toys & Masturbation

Myra has had me, Jack, the one and only, wearing a Confin (chastity device) for three weeks now. She had announced brightly that she'd only have sex with me if I wore it. She'd read about using one in a little porn book passed around between her and her friends. I think they thought it hot and entertaining but only Myra got it into her head to actually liv...

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

Open in Reader

Evolving Sex Life Pt. 01

by slavecaro on Jul 14, 2020
BDSM

This story is part true but if chapters progress, it will evolve to include pure fantasy. It is about a husband and wife married for several years. The sex at the beginning is rare and boring for both. It will include many kinks but is starting out as wife humiliating a husband, denying him intercourse, and long nails. It can go a lot of places from here bec...

Trading

by WFEATHER on Sep 16, 2017
Transsexuals & Crossdressers

"I have an idea, honey," my wife began in a tone which suggested that she had a sexual idea which she wanted to try. That was how we had begun breath play, with me strangling her with the belt of her favorite robe while I made love to her. That was how we had begun experimenting on occasion with bondage, discovering how she enjoyed being teased while restrai...

Soma's Journey Ch. 01: First Time CD

by SomaSlave on Dec 3, 2019
Transgender & Crossdressers

I never thought my first encounter involving a CD would be with me as the CD, but strange are the ways of sensual exploration. I had answered an ad looking for a man who wanted to play in stockings and panties. After establishing my submissive nature (and torturing me with wonderful photographs of CDs in bondage), the man at the other end of the ad had persu...

The Basement Ch. 03

by FiveDots on Jan 20, 2020
Transgender & Crossdressers

Welcome back to The Basement. Warning that this story continues to become darker. The sodomy begins here... --------------------- Once he started fucking me, he didn't stop. I complained, I pleaded, and even begged but, so far, after weeks of blowjobs and cock worship, I had ultimately complied with every demand. So, it was pretty obvious, in retrospect,...