Sissy Doctor Stories

36,636 results
Orientation
Length
Source
Infinite Scroll

Abducted and Turned Out Ch. 04

by dawnib66 on Sep 12, 2017
Transsexuals & Crossdressers

I let the landlord in and he immediately pushed me over the arm of my sofa and yanked my skirt up and pulled my panties down. I moaned and purred while he plunged his cock in and out of my pussy, fucking me furiously for about 5 minutes until he filled me with a nice hot creamy load. Then, without a word, he zipped up and left. I stayed there for a couple o...

From John to Jenny

by GaysonPerry on Apr 20, 2020
Transgender & Crossdressers

John put on the little black dress and became a she, her little clitty slipped out from beneath the red lace panties and she fondled the outside of the lacing. With this, she felt sexy: combined with the 'fuck me' pumps and a red bra she was about ready to be a sissy, except there was nobody around except her and her toys. All that ruined the illusion was...

Becoming Mindy Ch. 04

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

I have taken some shortcuts in this story to make it more readable. The process of getting hormones was a little more detailed (i.e. psychological evaluation and ongoing group therapy sessions), but would bore the average reader, lol. Although I combined three separate visits to tell this part of the story, it is fairly accurate (i.e. He fucked me on each vi...

My Medical Vacation

by sissymissyct on Jul 10, 2019
First Time

BRENDA'S MEDICAL VACATION by Brenda Finally on the way to the airport. My first trip to Europe. I wish my wife was coming with me but she was just dropping me at the Laguardia international terminal. I certainly hoped we would get to go to Europe together and do the normal sightseeing and partying that most couples enjoy, but this was a special trip for me....

Neighbors Sissy Son Ch. 04

by newfield1981 on Apr 3, 2018
Transsexuals & Crossdressers

Authors note: All characters are 18 and older. This is a stroke story about a transgender boy as he transitions into a girl and the mischief she gets into along the way. It's not meant to be a "how to". It's strictly fantasy. I hope you enjoy and cum lots! ***** It's been three months since that fateful day Tiffany's mother Carol became aware her son was...

Euphoria Resort

by sissyashley4bbc on May 4, 2020
Transgender & Crossdressers

"Welcome to Euphoria!" a good looking black man said as he greeted my wife, Jess, and I. I couldn't help but notice two scantily clad maids getting our bags for us. "Come right thus way to check-in with your specialist," he directed us. We clutched each others hands and hurried in, we were giddy to get started. Euphoria was no ordinary resort, it was cou...

Wet Dream Pt. 02

by sissymissyct on Jan 21, 2020
Fetish

After breakfast, Gayle said she would drive me to the doctors office. It was across town but shouldn't take too long to get there. "How did you find this doc?" I queried. "Oh, one of the gals at the gym mentioned her. She is the doctor that got me on the HRT treatment I started recently. I think you will really like her." "Her?" "Yes her. I thought you wo...

Dear Diary

by MissYellowPanties on Mar 26, 2019
Transgender & Crossdressers

Dear Diary. I never really like my job, the best I could manage was feigned enthusiasm in front of my supervisors, but it paid well, and so far I had been able to spoof my way through 3 years of regular paychecks with minimal effort. Cube life sucked the life out of you, but computer programing wasn't really difficult and at least it paid far better than m...

Superstars Rise and Superstars Fall Ch. 01

by felicia_rene on Oct 6, 2020
Transgender & Crossdressers

Superstars rise and superstars fall 1 Part 1 of 4 By Felicia Rene This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy the story Synopsis: The underlying theme is transformation and sexual punishment of the main character for his anti-gay womanizing feelings. For his heinous actions initially making h...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...