Crossdressing Bondage Stories

15,183 results
Orientation
Length
Source
Infinite Scroll

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Whore of the Dragon

by Conan The Librarian on Feb 19, 2020
Fantasy

There, amongst the remnants of the dead race, where their greatest queen reigned, two dragons lie dormant. One of pure evil, one of pure good, both yearning for a vessel, both lusting for a mate... She may be adequate for that purpose, our forlorn child... We shall see. "Silence, fools. We are close to the inner sanctum." The two mercenaries exch...

Open in Reader

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

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...

Master Walt's Homecoming

by tommibottom on Sep 15, 2017
Transsexuals & Crossdressers

Walt had been talking for months about taking me with him on one of his river trips. He was the skipper of a river tugboat and would be gone on trips for about a week at a time. When he finished a run, another captain would take his place and he would be home for a week. In the year and a half ,or so, that I had lived with Walt and Ellen, I lived as a femal...

I Want To Be The Guy

by ilovebananas on Mar 23, 2020
Transgender & Crossdressers

Just remember love is for all genders and sexualities. Love is, therefore, limitless. Not all romances full under a vanilla umbrella. We can give love to our crossdressing boys x So there was this small gathering of people. In fact, there were very few people. I had told most of the kids not to bother with my birthday as they had all made an effort to atten...

Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

A Homecoming

by Lifeinlingerie on Dec 3, 2019
Fetish

Gwyn and I had not had sex in about three weeks. This was not the longest dry spell we had encountered, but it was longer than either of us was happy about. There had been a variety of good reasons for this unintentional celibacy, but I knew that it was all coming to an end today. Gwyn had been away at a conference for the past few days, and a combination of...