Sissy Doctor Stories

36,636 results
Orientation
Length
Source
Infinite Scroll

Boredom and Therapy

by oldhippie1949 on Aug 31, 2017
Group Sex

The following is a true story. Naturally, all the names have been changed but all the events described took place just as I have written. If a bi-sexual threesome is not to your tastes then move on. If you are too young to be reading this, then move on. ***** I was so bored. Even my dog couldn't shake me out of it and. believe me, he tried. I didn't care t...

Jerry becomes Jill Pt. 04a: Doctor

by gasissynora on Apr 27, 2020
Transgender & Crossdressers

Jerry becomes Jill: Part 4a: Summer - School This is the fourth part of my story about how I became Jill. Summer school continues with female hormones being introduced and a trip to the Doctor. Jill is looking forward to the month long break coming up at the end of the summer. Spring quarter ended with a short break, we started into the summer quarter. Not...

Nurse Jenny Lends a Hand

by Emmcee20 on May 15, 2019
Fetish

ABOUT THE FIRST THIRD OF THIS STORY IS BASED ON TRUE EVENTS THAT OCCURRED A COUPLE OF MONTHS AGO. Feeling dizzy and light-headed and clearly reacting to something I'd either eaten or come in contact with, I'd taken a fall and cut my left hand quite badly. It was soon apparent that I was going to the hospital. My son delivered me to emergency and within an...

Prison Woman

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

I get a lot of questions from men that I meet. Not all of them want to have sex with me; some just are curious about what I'm all about. A lot of people who know me know that I am an extremely feminized male who became a Queen when I went to prison due to alcohol related offenses. I always say that I became a woman in prison - and that is true. But I guess...

Purty Prison Guard

by Wholemanz on Sep 11, 2017
Erotic Horror

WARNINGS: Contains transgender themes, Sci-Fi, explicit sex, mild violence, bad words, and strange ideas. It has only the strange things that dribble from my head. If you are not old enough, mature enough, open minded enough, and especially not smart enough to stop reading should you find yourself becoming offended viewing such a story, don't! * * * * * * *...

The Playpen Ch. 02

by Chrissytgif on Sep 15, 2017
Transsexuals & Crossdressers

As Master Dave restarted Jillian's training program he realized his mistake. Chrissy's program had not been running. When the override command had failed, there was nothing to direct her to a docile state. Furthermore, in a panic he had flooded the whole house with the gas including the control room. With the control room flooded he fell prey to the only pro...

Brick

by coldsteel on Sep 12, 2017
Erotic Couplings

Tuesday morning, Operating Room 9. The red-grey tumor stubbornly clung to the sides of the pelvis. For three hours, the two surgeons worked to coax it out. "I've got the view," said Brick. "Two Kelly clamps, scissors and a stick-tie." The instruments danced in her fingers. In seconds, the tumor was out and Brick was throwing one-handed knots deep inside...

Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

Open in Reader

The AA Men

by DrLuverotica on Sep 17, 2017
Loving Wives

"Jo, the car's broken down again...I'm going to try and get a push and get it restarted." I left my wife the voicemail message and went to back to my office. Carl and Don were still trying to sort out a glitch on the new website we'd been designing for a client. "Battery gone again?" Carl asked, barely looking up from the PC. "Yeah...Can you..." "Give...

Tonight, You Will

by trixie_leigh on Mar 3, 2020
Transgender & Crossdressers

Yes, you should be on your knees for this. Definitely. That's what you like isn't? To serve me? To submit? To be my little bitch? You look awful cute in that chemise, although it does keep falling down your left shoulder doesn't it? Too bad you don't have actual tits to hold it up. That's okay, we can pretend. I mean, I know you pretend all the time. But I...