Sissy Contract Stories

32,406 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

Sparrows Caught and Caged

by nikisixx on Oct 6, 2020
Fetish

NOTE: This is a work of original fiction. All names, circumstances, or situations herein are purely fictional. They are not based upon either real people, governments, organizations, places, or real events. Should any parallels to real circumstances be drawn, historical or otherwise, they are purely coincidental. --------------------------------------------...

The Prostate Exam Pt. 08

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. His Dominant female doctor had pushed her finger just into his ring and...

Afro Stress Relief Ch. 07

by llts1970 on Sep 23, 2019
Transgender & Crossdressers

Author's Note: - there was a character in the previous chapter called Jane who was working in Tina's company, I realized this was too confusing because of the main character Dr Jane and so I've changed the name from Jane to Monica. I apologize for the delay in getting this chapter out and hope to have more chapters completed sooner. ***** Staci rang and sa...

Recruiting of a Sissy Maid Ch. 04

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel, Fitting Into Her New Lifestyle. Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room." Chantel grows more and more resigned to this new life as she see's a very...

Cindy's Humble Servant Ch. 09

by humbleservantbeijing on Sep 14, 2017
BDSM

About a week later, Peter was at Brian's apartment that Saturday at 9:00 am. He was on his knees in the living room cleaning the grout between the marble tiles with a toothbrush. He could hear Brian in the other room playing a computer game. He heard a key in the front door, and then Cindy entered the apartment. She took off her jacket and hung it on a hook...

Sissy Chantel, New Reality Ch. 07

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Seven: At 'The Agency' and I'm Off to a New Start In My Sissy Life. "Girls this is your new dorm mate, Sissy Chantel." one of the security staff says. The other staff member adds, "You shall take her into your group, help her set up her things and then take her around on a tour of the facilities and such. Report to the office after doing so, OK?"...

From a Husband to a Dutiful Sissy Ch. 06

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six will compress time a bit more forward in moving the story through time. It will be set two months forward from the original start date of the story in Chapter One, when Helen found out her husband Phil enjoyed crossdressing and fantasized about being sissy maid and a sissy slut. It all picks up with bit of recollecting from Phil who is now Chante...

You Can Always Say No Ch. 06

by AngelCherysse on Sep 25, 2017
Transsexuals & Crossdressers

We pulled up in front of the professional building opposite the sprawling medical center. The intervening multi-story parking structure was well-lit, but sporadically populated with vehicles this long after business hours. "What are we doing here?" Angie questioned as we stepped out of the cab. "Baby, Faye and I have someone we want you to meet," I explain...

No Turning Back

by Wanttobefemme on Jun 9, 2020
Transgender & Crossdressers

The story continues. Reading my previous submissions may help you appreciate what's about to take place next. However, the story also stands on its own. The shower was nearly over, but the real journey had not even begun. He had never experienced anything even close to living out this lifelong fantasy. Being dressed and used as a plaything, a slave, to...