Sissy Princess Stories

21,927 results
Orientation
Length
Source
Infinite Scroll

The Settlement Pt. 02

by cathynylons on Sep 14, 2017
Transsexuals & Crossdressers

I went to my room and sat down at the vanity to remove my make-up, remove my clothes, and hang them up in the closet. Saw a glimpse of myself standing in front of a full length mirror wearing bra, panties, garterbelt, stockings, and heels and began to realize my predicament. When I got to bed I spent the night lying awake, tossing and turning. It was dawn be...

Mistress Marisa's Estate Pt. 35

by keptsissy on Sep 15, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ******************************** You are seated on long black leather couch. Soft music plays to those selected to be in attendance at your very private s...

A Very Hard Working Girl

by keptsissy on Sep 12, 2017
Transsexuals & Crossdressers

I jump around a lot when I tell my story. I don't always tell it in the order that it happened. But I do tell my story accurately. It's all me. I write from experience, love to share the dirty little kinky things I do. There is no moral to the story, no ending. I just like to write about the things I've done and continue to do. And I love to think back and r...

Mistress Kate Pt. 01

by corduroysissy on Feb 7, 2018
Transsexuals & Crossdressers

L. Jordan Bains wasn't sure of what to expect when he stepped into the large wood paneled office, but he knew whatever it was it wouldn't be good. He was in a lot of trouble, the Leprechaun wasn't known for having a forgiving nature. Jordan had never seen him, he only knew him by reputation, when you hung around the poker tables of Waller City you heard all...

Sissy Prince: Origin Ch. 03

by SatinSlip on Feb 13, 2018
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Olivia pulled off his scratchy wool tunic. It had covered him to just below his cute girly ass. It was uncomfortable to wear, made by Orcs. Yet for some reason it turned him on. His tiny sissy bump was now revealed to the world. It was erect, yet not quite two inches long. He...

Accidental Daddy: A TS/CD Novella

by RoryOmore on Dec 24, 2018
Transgender & Crossdressers

Authors Notes: This is an edited and consolidated version of "Accidental Daddy," originally posted in separate parts between November 2017 and March 2018. ----------------- This was my first attempt at a TS/CD story, written to explore the reactions of a straight older male on encountering a sissy for the first time. Tory Buckingham was inspired by my im...

Being My Roommate's Sissy Pt. 02

by SubTessa on Sep 19, 2017
Transsexuals & Crossdressers

Waking up this morning was just a mix of feelings - shame, pleasure, defeat, embarrassment. Tanner's display of 'power' over me was three days ago, and in that time - according to his brags and occasional light-hearted messages he likes to show me - he has convinced Kara to come over to 'hangout' tonight. My mind was so confused, I told myself I would stand...

Mistress Marisa's Estate Pt. 28

by keptsissy on Sep 12, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ******************************** He's naked. And he has a beautiful sculpted male body, tight rear end. You love this man's body. You watch it move slig...

Master and Four Subs

by totk6432 on Apr 17, 2018
Fetish

This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. ======= The rule is simple: I ring the doorbell and let myself into Master Daddy's house. Susan, my 25 year old personal assistant, is with me. She is in charge of me at work. Sh...

Internet Meeting Ch. 04

by Stillherer on Sep 16, 2017
Fetish

I tried to appear casual as I wandered about the busy mall wishing to remain anonymous, discrete. Beneath my attempt at normalcy my body seethed with frazzled nerves as I checked out Charles' appointed meeting place. Charles had selected a toilet in a quiet secluded corner of one of the upper floors. I hesitated at the door, casting a nervous glance over my...