Sissy Doctor Stories

36,636 results
Orientation
Length
Source
Infinite Scroll

A Game within a Game Ch. 02C

by doberinca on Sep 16, 2017
Transsexuals & Crossdressers

Author's Note: This is the second story. I still have sometimes trouble to find the right syntax. I hope you still have fun in reading this second story. A third will be following. The characters involved will appear more 'human', not real good and not real bad, and make sometimes bad decisions. Chapter 2C. Dr. Catherine. The next morning when Rob wake-...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

The Gynecomastia Kid Ch. 01

by Johnboy9 on Sep 14, 2017
Transsexuals & Crossdressers

This story will be told in first person narrative but this first part is written in third person narrative because the first person, or main character, is unaware of the events unfolding in this scene. ***** Inside the kitchen of her boyfriend's house Crystal makes a last ditch effort, calling his stepmom, Dr. Burns, for help: "Crystal, you're saying all...

Julie is Sold to Mistress Amanda

by Pretty_Sissy_Julie on Apr 1, 2020
BDSM

Julie followed behind her beloved Madame as they walked up the steps. Julie had worked at Madame's brothel since she turned 18. She remembered how she went to Madame after she was thrown out of her house. Julie's mum caught her in bed with her father and was furious and made Julie leave. After a brief stint as a street walker Julie was brought to Madame and...

Somali Hijabi MILF Doctor

by Samuelx on Sep 12, 2017
Erotic Couplings

Alright, I might as well confess at this point. I've got a thing for "mature" Somali women I see walking around wearing the Hijab and those traditional long skirts they wear. Every time I see one I get an instant boner. There, I said it. So why don't I feel better? As I sat inside Dr. Fawzia Hassan's office in downtown Ottawa, Ontario, I felt frustrated like...

It?s Either Break Up Or Make Up

by felicia_rene on Sep 12, 2017
Transsexuals & Crossdressers

PART 1 Synopsis: I always was put off by the unsuspecting stupid love sick, pussy whipped guy is transformed against his will because the will wants to run off and have an affair, I never understood why they don't just pack and leave. The underlying theme is transformation and sexual punishment of the main character with anti gay womanizing feeling for hi...

A Dog's Life Ch. 06

by Compliant1 on Sep 19, 2017
BDSM

I took my time walking down the row of port-a-potties slowly and rapping on the door of each one. I gave two an extra rap, just to increase his anxiety. I finally got to the last one with the Out of Order sign and gave the door a good rap. I heard a plaintive voice. "This one's occupied!" "How can it be occupied? The sign say's, Out of Order." "Well, it i...

Subliminal Obsessions

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Finding a place in the city is rough sometimes for a good place honestly and I spent two years in a real shitty studio apartment with not even a laundry room in the building and just no room or increasingly no room. And my luck turned around after I won money. Seriously there's a 50-50 draw at work and just sort of on a whim I put my name in and I won. Not...

The Challenge - Wear a Thong

by taraterry on Oct 11, 2017
Transsexuals & Crossdressers

There is something deliciously naughty about a boy wearing women's thong panties for a day, after all, the first time you wear a thong all day long, especially on a week day, you will be going about your normal routine. Whether it be to class, to work, or whatever you normally do, you will have it on all day, even when you're not fully sexually aroused. Why...

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...