Sissy Life Stories

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Jasmine - Sissy Slut Transformation Pt. 02

by BillyBaroo4you on Aug 31, 2020
Transgender & Crossdressers

A Sissy Boy Transformation (Continuation of Part I) Part II - A "Real Sissy Girl" Now Jazzy looked down at the table than in the mirror, then slowly began to apply her makeup, heavy amounts of it to get that bimbo presentation that Mistress wanted so bad. Sparkling hot pink lip gloss, she was wet by the thought of it. Pressing it to her lips, the butterfli...

Sissy Chantel, New Reality Ch. 08

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving on to my life at 'The Agency' Some Interesting New Things. It's 5:00pm sharp, we all must be present and ready to enter the eating area. As we all enter a small but purposeful eating area for us sissy girls, we first get a tray and a plate and mug or glass. The sissy maids who prepared our basic dinner have the food out for us. Today i...

The Prostate Exam Pt. 05

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Since giving himself away in his first prostate exam to his Dominant Doctor Megan he had been prepared for use by an old Master, now Sissy was on her way to be used. Sissy was breathless as she read the text from Master V, she looked around the small airport to make sure she didn't know anyone, whilst she was looking at her texts. Thank goodness she didn't....

The Awakening of a Sissy Pt. 03

by sissyjolie4u on Jan 20, 2020
Transgender & Crossdressers

As i was watching the video of Mistress and I for the 3rd or 4th time, my phone rang. "Hello my sweet Joey, how are you doing? I so enjoyed spending our time together, I'm so proud of you and the progress you are making. Are you still in your pink bra and pantie? That is such a sexy look for you, it makes you look so soft and feminine. Tomorrow we will build...

April’s Child

by 4glory6 on Sep 16, 2017
Interracial Love

"Annie, you take them children up third floor. They like to wear Miz. Irene out on the trip. And you, Toby, stop moonin' over Annie and get the ice chest goods into the house and in the ice box. You got ice in the ice box didn't you?" "Yes ma'am," Toby answered as he trotted out the kitchen door and down to the Buick car in the drive below. "And you, Miz....

Humiliated Stable Sissy

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

After a long week at work, I was looking forward to a quiet weekend of relaxing in front of the TV with a beer, but my fairy godmother had other ideas. "Good morning sissy," came her stern voice as soon as I woke up Saturday morning. I whimpered, immediately knowing I was in for a humiliating weekend. She frowned, not pleased with my whimpering. She's an ol...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

Sissy for the Family

by sissyboi4daddy on Aug 21, 2018
Transsexuals & Crossdressers

Hi, my name is Isaac. I'm 21 years old, Asian and a child of divorce. My father decided he wanted nothing to do with me the moment I was born, and my mother held 2 jobs to raise me. When I was 18, she decided she had enough of the hard life and remarried. She remarried Jack. Jack was a white, bordering on obese man, who was 12 years older than my 42-year-o...

Humiliated Stable Sissy Pt. 02

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

I woke up exhausted at the crack of dawn to Fairy Godmother obnoxiously clicking her fingers next to my ear. I minced downstairs, still locked into my ultra prissy outfit (where was the key?) and my totally exposed diaper, already damp from last night. I shuddered as Fairy Godmother ordered me out into the back garden, where I stood and curtsied to the risin...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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