High Heels, Sissy, Wife Stories

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From Husband to Man's Sissy Wife Ch. 02

by Pantypansy on Jul 9, 2019
Transgender & Crossdressers

I had just finished changing into a black satin, frilly French maid's outfit - which Hamish had picked for me - when I heard voices downstairs. I pulled my silk panties up tight and put on a pair of black high heels and tottered down the stairs. Hamish had changed into jeans and a button-down shirt, and was chatting to my wife in the kitchen. Both were l...

Controlling Sissy Janice Pt. 01

by sissy_janice on Jul 6, 2020
Fetish

I was uncertain which category I should post this story under. I love the crossdressing stories most, and this would certainly fit there. But the main action really is about cuckolding, so I've put it in the Fetish section. *** I had thought that my wife was unaware of my crossdressing. Not only was I wrong but, as it turns out, I was the one unaware - -o...

Set Up Ch. 01

by Sissy_Ashlee on Sep 15, 2017
Transsexuals & Crossdressers

This is my first attempt into writing an erotica story. This tale will contain themes of female domination, crossdressing, and eventually MM sex. If any of this is not you thing, please scroll on. Otherwise, please let me know how I did. ***** Since I was a teenager, I had been bicurious. Not really interested in men, but what is between their legs. My obs...

Becoming a Sissy Maid & Slut Vol. 13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Two: Satin, Ruffles and Lace, Sissy Maids contracted out to Work. Monday morning and I arise as typical at 7:30am, enema, shower, shave do my makeup and put on a maids dress for the day. Today it's back into a black satin one. Master told me though to put on black back seem pantyhose for today which I dutifully do and make sure the seems are...

Yes, Mommy Ch. 02

by searic on Sep 13, 2017
Fetish

What follows is a continuation of a story of the humiliation and loving domination of a submissive, cross-dressing man by his Dominant wife. She has for the first time invited another person to witness his subjugation by inviting her work-friend Debbie to visit. Husband and wife love each other deeply, and they love to play, too! * -Part II As my lovely...

Caught in Her Panties Ch. 02

by Knightofround on Sep 16, 2017
Transsexuals & Crossdressers

This is a fictional story as was part one. The content of this story may not appeal to everyone. It includes female domination, crossdressing, strapon, lesbian, gay, and such. Just keep in mind that it is fictional and should not be taken seriously. Otherwise just enjoy the read. ***** It has been almost a month since my wife Mary discovered my secret. She...

Black Mistress 4 Black Male Sissy

by Samuelx on Aug 18, 2017
Fetish

Sitting in my chair completely naked, I stroked my strap-on dildo as I watched my Black male slut parade in front of me. My name is Veronique Marceau and I am a Dominatrix. Standing five feet eleven inches tall, wiry and muscular with a thick booty, I look damn hot and I know it. My skin is dark brown, shined to perfection with lotion for tonight's performan...

A Photo Session, My First

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

When he called and said "We're going to something special today, sissy boy." I got instantly wet in my panties. He arrived at my house and stripped out of his clothing almost before I had a chance to close the door. I feel his large hand cup my penis and balls. He covers them completely and easily. I'm small, less than 3" erect, baby-like. I feel my little...

Sissy_World 03

by JDBones on Sep 16, 2017
Transsexuals & Crossdressers

Billy rode in the front seat of the car, staring out the window, and watching the world go by. His mind swam and his body already hurt, but he knew better than to protest his pain to his Husband. If he did, he would be punished with a Bare ASS Spanking and he didn't want that. He stood at 5'6 and weighed maybe one hundred pounds soaking wet, but he doubted...

Sissy Maid to Be... Ch. 02

by missjennymaid on Sep 10, 2018
Transsexuals & Crossdressers

I would recommend reading Chapter 1 to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jeremy is get...