Sissy Doctor Stories

36,636 results
Orientation
Length
Source
Infinite Scroll

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

Office Cumslut Ch. 01

by DrLuverotica on Sep 12, 2017
Loving Wives

FRIDAY MORNING "Are you going to work dressed like that Jo?" My wife was dressed in black, sexy high heels, black stockings with a pink 1920s style pencil line up the back of them, pink frilly satin panties (she hates thongs) and matching push up bra. "Yes I am hubby," she purred, as she pulled a navy blue, short pleated skirt over her hips. "Is there s...

Friday Night

by DrLuverotica on Sep 13, 2017
Loving Wives

I arrived home from work at 6pm on Friday completely exhausted. It had been a killer week in work. We had had some new software installed that had played havoc with our macs and it had taken half a dozen of us until 11pm the previous night to finally fix the wretched thing. As soon as I walked through the door I kicked off my shoes, poured myself a glass o...

Unknown Waifish Model Ch. 01

by Couture on Sep 12, 2017
Transsexuals & Crossdressers

We lay curled up to one another in the hotel bed, Sandra and I. I looked forward to the day we'd no longer have to make do with hotel beds and the occasional foray to my apartment. Yes, one day soon, she would leave her bastard of a husband and move in with me. God, she was beautiful. Her blonde hair was mussed up, as she lay on the pillow. Her face had th...

Dr. Hottie's Story

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

Stuck in my office again. Tired, stressed, hungry, a little bored...I hate admin. Working as a doctor has its rewards. But the long hours and endless paper-work are not one of them. Hubby, though he's patient and understanding, is getting increasingly frustrated. It's affecting our intimacy - especially our sex life which is now frequently no more than once...

Dr. Miller Comes to Call

by ElorraButler on Sep 14, 2020
First Time

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Dear Reader, A "THANK YOU" to 29wordsforsnow for kindly reaching out and being my wonderful Proofreader/Beta reader on this one! It is so nice to have a second set of eyes and perspective on things! So again, Thank you!! As always, characters are all 18+, fictional and h...

Winning Big in Las Vegas

by marykay9 on Feb 6, 2018
Transsexuals & Crossdressers

I was in Las Vegas staying at one of the "lesser" hotels, playing the slots to kill time waiting for a "Shemale" show to take place. I thought that the review would attract other transvestites like myself and hoped that I might get up the nerve to wear my feminine clothes and mingle with other genetically challenged ladies. Unfortunately, a normal crowd surr...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

Aunty's Toys Ch. 03

by novelcriss on Feb 10, 2020
Transgender & Crossdressers

*Thank you for the votes and comments on parts one and two. Sorry I am so slow at this!* *** Simmy slowly came round. A fuzzy recollection of being carried to bed, spending the night half asleep, half aroused, snuggled between the two sexy plump women, hands stroking him throughout the night, feeling the slightly damp sheets where she had ... no he had or...

Transforming Brent Pt. 02

by sissymissyct on Jul 10, 2019
Loving Wives

Kept in Loving Wives to annoy the tiny dicked anonymous reviewers that love to trash everything they read (after they wank to it). *** I woke up Sunday morning with a painful erection in my chastity and the pumps still attached to my breasts. I reached down trying to find a way to ease the pain in my penis. Nothing seemed to help. Maybe Wendy will be up so...