Sissy Exam Stories

13,798 results
Orientation
Length
Source
Infinite Scroll

The Appraiser

by ctlthrmn on Sep 13, 2017
Transsexuals & Crossdressers

The seminar started at the local Marriot today. I, as the lead appraiser for my office was the main organizer for it. We had brought in one of the best appraisers in the East to share his expertise in appraising and developing a larger client base. The real estate market on Eastern Long Island was hot and I wanted to capture more of the $$$ it was spreading...

Old Uncle Jack Visits Ch. 04

by tazsis1 on Sep 19, 2017
Mature

[Please read earlier parts of this series. I hope they add up. Thank you for your encouragement and comments and impatience for more and occasional abuse -- it's all a key part of the fun of writing these stories. Don't hesitate to get in touch. At least one more instalment to come.] * I watched it all from the floor our bed; Uncle Jack taking, ravishing m...

Sissy for Mommy's Nipple Cream Ch. 05

by ppeaks42 on Nov 2, 2020
Transgender & Crossdressers

The evening after Jaime's doomed attempt at seducing Julia found the young sissy crying into her pillow as she tried to reconcile herself to the whirlwind of changes she'd gone through. Less than two months ago "Jaime" had been nothing but a shared figment of imagination, a character he dressed as for his regular breastfeedings with his mother. When he'd tri...

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....

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

TS Princess Ch. 01: Fucked by My Warden

by TSPRINCESS on Sep 16, 2017
Transsexuals & Crossdressers

It had been several weeks since I left home with my cousin brother for my breast-enhancement surgery. All our family knew was that I was going to some cram-school to get coaching for Pre-Medical Exam (AIPMT). My cousin brother had been supportive of me not only since he cared for me; it was due to his own advantage of having a full-formed girl at his disposa...

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...

Ms. Margo

by lyzunchik on Apr 3, 2019
BDSM

This is a partially true story, with some embellishments and enhancements out of my own fantasy. I'll allow you, dear readers, to wonder what is true, and what is contrived, where truth ends and fantasy begins. Enjoy. ;) Mistress Margo was waiting for me in the reception hall of Saint Petersburg Airport. I had been there a couple of times before, but this t...

Balls On The Line In City Trading Ch. 02

by gomorrah on Sep 16, 2017
Transsexuals & Crossdressers

So with much apprehension, I turned the handle on the blue door. Stepping through, I struggled to adjust my eyes to the brilliantly white light streaming out of the other side. I raised my hand to try and filter the glare, and heard the door click shut behind me, and then double-click again. Instinctively, I tried for the handle on my side, but there was no...

A Look Into My Mind: Uncle Sissyboy Ch. 03

by rickiee_2002 on Sep 25, 2017
Fetish

Shortly after I drifted off to sleep, I was awakened by the feeling of something hot and wet hit my body. I looked up and noticed one of the male subbies had just squirted his cum on my body. My negligee had ridden up and the cum was on my side and dripping off my side and onto my stomach. I looked up at him and he just got up and walked out of the room. Lau...