Sissy Exam Stories

13,798 results
Orientation
Length
Source
Infinite Scroll

The Prostate Exam Pt. 05

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Since giving himself away in his first prostate exam to his Dominant Doctor Megan he had been prepared for use by an old Master, now Sissy was on her way to be used. Sissy was breathless as she read the text from Master V, she looked around the small airport to make sure she didn't know anyone, whilst she was looking at her texts. Thank goodness she didn't....

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...

Training Aide Ch. 02

by Angelscuck on Sep 16, 2017
BDSM

Mistress Elaine stoop up, causing me to roll off her lap onto the floor. I just lay there naked, sniffling like some little sissy, waiting for my next ordeal. My Mistress then said, "It's a good idea, at this time, to let your slave have a few minutes to recover. It also gives him time to let the realization set in, that he has been totally broken and is...

The Dominatrix Order Pt. 04 Ch. 03 - Femdom

by Jwwsmith on Apr 23, 2019
Fetish

Sixteen days before the next supply of Medication 42 was due to be manufactured, General Callisto paid another visit to Femininus. Upon the General's arrival, she was nonplussed when she received an invitation to have drinks with Isabella at her castle. She arrived at Isabella's residence that morning, dressed in a modest black knee length dress. Servant Bul...

Danny to Danielle - Beverly Awakened Pt. 03

by Deviana on Apr 13, 2020
Transgender & Crossdressers

Chapter 6 Three days had passed since that night. A few business meetings went by with little issue and most all of home life had returned to some level of normalcy. Beverly slept with me.. or, I guess I should say, I was allowed into her bed. We had our normal morning coffee and small talk about 'stuff'- work, the kids (all grown), chores around the house...

Ugly Duckling to Sissy Princess Ch. 04

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Chapter 3) Several nights had passed after the party at the mansion and kissing Ted. Bernice called me Saturday and Sunday, but, both nights I told her I could not come by to see her. On Saturday, my girlfriend went to a party thrown by the basketball team. I knew she would end up fucking one of them, he would use her like a piece of meat,...

Behavior Modification Institute Ch. 07

by NancyPan on Sep 12, 2017
Fetish

I had been kneeling in front of Ms. Panington for some time as she finished her breakfast of omelet, bacon, toast, and orange juice. My mind was firing in a confused fashion and I was unsure which of many thoughts, feelings, and impulses to pay attention to, and which to ignore. Fight or flight was quite pronounced and I contemplated getting up then and ther...

The Path to Happiness Pt. 04

by brendachaplin2000 on Oct 8, 2019
Transgender & Crossdressers

After couple of days I had settled in to Roger's spare room. I cleaned and cooked for my room and board, not that I was a great cook, but I could warm up food without burning it. I was living full time as Brenda now. My last outing as Brian came when I went to my Store job and quit. I had only worked there a few weeks but the manager wished me well when I t...

The Journey Pt. 03

by MissYellowPanties on Sep 14, 2017
Transsexuals & Crossdressers

Training It was an unusual feeling walking down the corridor, my sissyclit was hard with excitement and I had not yet adjusted to the feeling of the butt plug placed firmly in my boypussy. I still tried to move in a ladylike fashion, but the strange sensation was overwhelming and I stumbled suddenly out of time with Mistress Anna's gait. Mistress Anna...

Cloned!

by Wholemanz on Sep 14, 2017
Sci-Fi & Fantasy

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! I hereby gran...