Sissy Test Stories

46,770 results
Orientation
Length
Source
Infinite Scroll

The Awakening of a Sissy Pt. 07

by sissyjolie4u on Mar 9, 2020
Transgender & Crossdressers

I was a giddy as a school girl knowing that I would be sleeping with Tim, Curiosity was building inside me. I was going to sleep with a man for the very first time. What was the special surprise that Tim had planned for me. All night long, as we watched sissy porn, Mistress kept harassing my pussy with various levels of my trainer. I was happily enjoying us...

Simon Sissy Slave Ch. 03

by Timewarp10 on Jul 30, 2019
BDSM

Mr Berne watched with satisfaction as the sissy paraded in the post room. Sissy walked gracefully in high heels. His ballet training made it easy. He knew how to walk like a woman. He had practiced, and he could walk with a book balanced on his head. It gave him poise, and the high heels gave elegance to his calves. The skirt was short enough to look slutty,...

Neighborly Relations Pt. 02

by grizzley123 on Jan 15, 2019
Fetish

NOTE: I always appreciate comments. You can read my slightly longer message on the first part of the story, but the gist is... I like my themes, you might like other ones. But I always enjoy comments, regardless of their content. **************** It helps to read part one where my neighbor starts to take control of me by using his incredibly hot step-daugh...

From Husband to Man's Sissy Wife Ch. 03

by Pantypansy on Jul 15, 2019
Transgender & Crossdressers

'So how was it, sweetie,' Hamish asked me as I opened the door. I was still shivering with desire from licking up my wife's lover's cum off her huge, oiled tits in 'their' bedroom downstairs (actually my marital bed).. I felt a sudden wave of emotion, after being so overcome with desire to watch my wife's lover come all over her. I had helped him by pushing...

The Gynecomastia Kid Ch. 02

by Johnboy9 on Sep 16, 2017
Transsexuals & Crossdressers

It's been two weeks since I got out of the hospital and I was feeling better and better as each day passed. Having no income and no real money of my own, to speak of, I was forced to continue wearing the clothes that Crystal left me since I couldn't afford to go out and buy clothes of my own. I must say though I'm getting to like the soft, airy feeling of t...

Teacher Made Me into Sissy

by johntamilandrea on Sep 13, 2017
Fetish

HI! I am Sissy Andrea. This is one my fantasies about my teachers. This story is about feminization, fantasy. If you don't like these topics Please don't read. ALL THE CHARACTERS IN THIS STORY ARE ABOVE 18 YEARS OF AGE. My special thanks to "mywifesslave" for helping me in editing this story. ***** The story happened when I was 19 years old I loved sho...

Sissy Boy Chuck Becomes Just Sissy

by Krazy35 on Sep 14, 2017
Transsexuals & Crossdressers

A long time ago, I realized that I had a thing for women's clothing. I used to sneak into my sister, Jessica's room and get all dolled up in her clothes. She was a year older than me, but we were practically the same size. I got an incredible hard-on looking at myself in her full length mirror. I quickly undressed, put everything back the way I found it, the...

My Submission to a Real Man

by gbr2004 on Dec 28, 2017
BDSM

This is total fantasy and would never do many of the things I discuss. If not into really kinky play, humiliation, verbal abuse, and forced fem and strong discipline, please pass on this story. For all you other submissive boy and dominant men hope you like my fantasies. ***** MY SUBMISSION TO A REAL MAN It was our first actual meeting. We had emailed bac...

Turned So Totally

by gbr2004 on Oct 8, 2019
BDSM

It was our first actual meeting. We had emailed back and forth about what we were both looking for and found we had similar interests. He wanted to take a straight acting guy, take his masculinity away and turn him into his submissive sissy bitch. That is what I had been thinking and fantasizing about continually but could I actually do it? From our email ex...

Neighbourhood Terror to Sissy Pt. 16

by Fibaro on Jan 6, 2020
Transgender & Crossdressers

Chapter 18 Marcy had hoped the stop at CC's would have been the last one. She had suffered enough embarrassment for a day. Lisa's claim that they still had a few errands to run made her worry that it wasn't all over after all. Her worries were soon confirmed when they stopped in a rather seedy looking neighbourhood. Getting out of the car Marcy knew better...