Sissy Life Stories

219,972 results
Orientation
Length
Source
Infinite Scroll

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...

The Awakening of a Sissy Pt. 10

by sissyjolie4u on May 11, 2020
Transgender & Crossdressers

Best I could tell, neither one of us had moved an inch from the position that we fell asleep in. The urge to pee woke me quite early, like 4 AM early. A smile came to my face as I realized I was still holding Tim's cock. While barely awake, I made my way to the bathroom and took a seat to pee. While sitting there peeing, it hit me that I should probably do a...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

Becoming a Sissy Maid & Slut Vol. 07

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Thirteen: Work, Work, Work, Around the House, At the Adult Store and as a Slut at Night. Monday, morning and back to my sissy maid services. Promptly I wake up at 7:30am. As per usual my morning routine of an enema, showering and dressing. Today I did have to reapply depilatory cream to keep my body smooth and hairless. It takes an extra 10 minutes...

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

Young Master Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

There I was, still impaled on a shemale's cock, one belonging to what was supposed to be my sissy slave, wearing her bra, her cum on my cheek along with my post-fuck smeared make-up, and my cum running down the full length mirror. "I fell" wasn't the best explanation for what happened, but it was all I could think of with my step-father's hulking frame loomi...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

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...

Alt. Queen of the Left-hand Turns

by maxdname on Sep 16, 2017
Romance

See that beautiful girl in the poster? When I first met her she was a simple hillbilly girl from Appalachia sleeping with stock car drivers in order to get a pit pass. Look at her now: she's a blond and a model with her own TV show that earns her more in a year than most stock car drivers will earn in a lifetime on the circuit. A national racing magazine i...