Sissy Doctor Stories

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Orientation
Length
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Infinite Scroll

Miss Guided

by MissMarianne on Mar 12, 2019
Transgender & Crossdressers

My name is Susan and my husband Charles, we are both 25 years old and have been married for one year. Recently Charles has been very depressed and He lost his job when the company moved to Malaysia. Lately his performance in bed has been sub-par and , in fact, he can't get it up most of the time. We feared he was becoming impotent but the doctor said the pro...

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...

The Retirement Party

by DrLuverotica on Sep 18, 2017
Transsexuals & Crossdressers

April 3 Jo had been singing it for days and it was driving me mad! "It's all about the bass, about the bass..." On and on she went until finally I screamed: "Enough already!" "Oh hubby. Do you not like my song?" "Well, I like the way you move to the song." Jo looked hot swinging her big sexy curvaceous ass in a short micro skirt and flicking it up occasi...

The Doctor's Appointment

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

My wife Jo had been suffering with a bad back for weeks. She works as a doctor and many of the procedures she has to carry out on patients require her to stand up for hours at a time. A couple of moths ago she fell off a horse on an activity holiday we were on. And she's never fully recovered. Urged on by my insistence to get her back checked out properly...

Eve Quest Pt. 02

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed so much more acceptable than an enema. I tossed my gown on the bed and fill...

Eve Quest

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 1 My name is, or maybe we better make that was, Andy Moore. Until recently my personal identification was in the name of Jamie Jo Moore and everyone I knew called me Sissy. My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,000.00 and an eighteen percent interest in an insurance company...

A Sissy Maid's Tale Ch. 01

by Erotictales4u on Sep 19, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy in the femdom niche, it is focused on male submissive humiliation and has a Sissy theme running through it. Is set in an imaginary future. ***** The cool air licking at my almost bare ass cheeks enhanced the feeling of nakedness, but I wasn't naked. In fact, it would have been...

The Prostate Exam Pt. 07

by His_fag_wife on Sep 18, 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. After he'd given away his naturally submissive tendencies by pushing bac...

I Become Wendy's "Wife"

by Quietoldie on Sep 16, 2017
Transsexuals & Crossdressers

After the amazing weekend I thought things would settle back down to our usual routine. She was out working all day so I had to wait until the next weekend to go shopping with Wendy for my new wardrobe. In the meantime she allowed me to wear any of her clothes that I liked but most were a bit too big for me and Wendy had only a few dresses and skirts to choo...

A Christmas Tail Ch. 03

by Angelscuck on Sep 13, 2017
Transsexuals & Crossdressers

The following story is written by my wife Angel. It is her view of the slave auction night plus my night as her slave and what she made me do. As I rode home in our car that night, a bit dazed, and reflecting on what the hell had just happened, I was surprisingly pleased with myself. I really had showed, mostly to myself, but also of course to my husband...