Crossdressing Husband Stories

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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...

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

My New Family Ch. 03

by eagle166 on Sep 15, 2017
Transsexuals & Crossdressers

Lying in bed talking to my wife, Heather. Rubbing her large swollen belly, Heather is pregnant with twins. Things haven't gone as well as we would have liked. Yes we are still very much in love, so there is no problem there. But Heather is 8 months and 1 week into the pregnancy and with twins, she has been very uncomfortable to say the least. Rubbing her b...

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...

Boy to Bride Pt. 01 Ch. 01

by sissyscarlet on Jun 19, 2018
Transsexuals & Crossdressers

Part 1: Adam MacDonald Chapter 1: Ms. Alice the Widow Adam carefully shifted the wooden board back in to its place. If only people knew what I kept up there, Adam thought, and smirked to himself. Before he was down from the stepping stool, he looked up at the ceiling 2'x2' entry leading to the attic—an artifact left for insulation and electrical, but Adam...

Disgraced Fiancee

by rik581 on Sep 16, 2017
Transsexuals & Crossdressers

"OMG, Laura please, don't make me do this," Dave pleaded one last time as it was now time to stand before her entire family and beg their forgiveness for his sexual indiscretions. She straightened the dress he was wearing, then adjusted his earrings. "No Dave, the talk is now over. You will perform this embarrassing act for me, and ask my family to forgive...

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,...

With Her Blessing

by komrad1156 on Sep 12, 2017
Transsexuals & Crossdressers

"Hello again, Kyleigh!" he said as he looked at himself in the mirror after carefully pulling on his very expensive human-hair wig. Ky Finley was now Kyleigh Finlay and she felt this wonderful rush of endorphins flood over her as she looked at the beautiful creature she'd become over the last ninety minutes. Ky had sandy blond hair so Kyleigh could easily b...

My Husband a Pornstar Ch. 04

by gtanya on Mar 21, 2018
Transsexuals & Crossdressers

Chapter 4: Conclusion Here is a small brief of what has happened till now: My fairy husband had been seduced by a strong man at home and then had agreed to be a sissy pornstar. Fairy new master had trained him as a sissy to perform in a gay movie without his knowledge that he was making a sissy trainer porn movie the whole time. I found out and threatened...

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...