Sissy Surgery Stories

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The Path to Happiness Pt. 06

by brendachaplin2000 on Nov 18, 2019
Transgender & Crossdressers

A few weeks passed since I moved to London, I had a few weeks before university. I had been kept busy with my waitress job, and the escort and stripping job was boosting my cosmetic surgery fund. The escort work, had led to a couple of shags, but for the most part my sex life had trailed right off. One night I was working busting tables at the restaurant, t...

Being Mindy Ch. 04

by mindyrose on Sep 15, 2017
Transsexuals & Crossdressers

In full disclosure, the following is not my first transgender surgery. I had my Adam's Apple shrunk in a previous surgery. However, that story was not one that led to lots of sex. Since this is a site for erotic stories, I have chosen not to share that surgery story. However, this one is about breast augmentation, which is a clearly sexual plot, and a fun se...

End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...

Becoming a Sissy Slave

by mikhaylacumme on Sep 16, 2017
Transsexuals & Crossdressers

He gave me the choice. He had programmed me for a week and knew which way I would probably choose, but he gave me the choice. I could get out. Or I could continue. It was up to me. On my knees or out the door. It was that easy. Now I had to choose. I guess I should backtrack, first. You might be scratching your head saying 'what choice?' Let me start...

Cockland Island Pt. 02

by Sissyhalo1 on Dec 3, 2019
Transgender & Crossdressers

I knew I was messed up in the head and didn't care. I knew I was getting brainwashed but didn't care the videos, the drugs, the sex. These nice, big, muscular, handsome guys were there eating with us as we shared a table and were being really nice to Jill and I. In my normal life people are just sorta nice, not nice in this way. It was kind of cool and y...

Making of a Porn Queen Ch. 02

by Scribler on Sep 25, 2017
Transsexuals & Crossdressers

I had set my alarm to wake me up early on Friday. Mark would be back from his trip by Ten AM and I wanted everything to be perfect when he got there. Tracy also got up early as she wanted be ready for when her husband arrived. I had to wear my house boy uniform as Tracy didn't want Mark to know what we had been up to for the last week. Even though I still wo...

It Happened in Mexico Ch. 01

by Angelscuck on Sep 14, 2017
BDSM

Joaquin lay in his prison bunk, his cock throbbing in his hand. He was thinking about Angel. Angel, the woman who had told him she could not see him anymore. She had found a man she wanted to marry, a man who could give her what she needed emotionally, love, understanding and security. A man she could depend on to treat her with kindness and always be ther...

Recruiting of a Sissy Maid Ch. 03

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Three: Training Done, Chantel is On Her Way. Waking up back in her cell, Chantel finds that her days being trained, orientated and broken off will here with the Burrows brothers are wrapping up. Mitch enters her cell and has her come back out and back into the house with him and Nate. Mitch says, "Well Chantel, time has come for us to part our ways...

Doctors Orders 1st Appointment

by Misslexia on Sep 13, 2017
Fetish

It was one of those days when things kept went wrong, right from the start. My alarm didn't go off, so I dressed hastily. I missed my train; I left my lunch at home and so on. It wasn't until I was almost too late that I remembered that I had a doctor's appointment that evening. I ended up having to run to catch my train, which was not a good idea as my appo...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...