Sissy Princess Stories

21,927 results
Orientation
Length
Source
Infinite Scroll

Snowbunnies

by tori_tgirl on Oct 12, 2017
Transsexuals & Crossdressers

I was finding it hard to concentrate on my picture... the creaking sounds from the box spring grew louder with each passing moment, making it harder and harder to keep my crayons inside the lines. I didn't have long to finish my coloring, maybe another minute or two but it was already the prettiest unicorn I'd colored yet, and surely they'd be happy. I strug...

Being My Roommate's Sissy Pt. 01

by SubTessa on Sep 19, 2017
Transsexuals & Crossdressers

We approach the door to my dorm, walking slowly with our hands in our pockets. Glancing over at her she seems sort of detached from the conversation, maybe thinking of what she's going to say when we reach my door? I feel kind of nervous as we step our way through the dim-lit corridor, it must be at least 11 at night now; all the dorms are so quiet - making...

Mistress Marisa's Estate Pt. 23

by keptsissy on Mar 26, 2019
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... ******************************** "I want to thank you for meeting me for lunch. I know you probably would have turned down my invitation had I made it on m...

His Sissy Bitch Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"You've come a long way, baby." He smiles at me, watches me as I cross my legs. I'm sitting across from him. I can tell the effect I have on him, every time he visits, sees me dressed fem for him, he's hard, rock hard when I meet him at the door. And I know what outfits turn him on the most. I know he fantasizes about me when he's fucking his wife. She doesn...

What a Night

by Anoun_Ymous on Sep 17, 2017
BDSM

It all started out innocent enough...here I was laying in bed next to my wife on this cold winters night, just two nights before Christmas. We had arrived on time to her parent’s house with nothing unusual happening on the way. It had been a pretty dull night and with her parents having gone to bed the two of us and her younger sister had decided to get comf...

Discovering Mistress Sarah's World Pt. 03

by oneguy4fun on Sep 12, 2017
BDSM

Chapter 7: A Brief Digression Mistress Sarah sat naked, in a stiff padded chair in front of a large vanity. She waited patiently for her two sex pets to return. It was time for Joe to learn how to properly dress her for a night out and she wanted him in full sissy attire for the event. May had been charged with the task of getting him back into his dress....

Casey's Submissive Journey Pt. 14

by corduroysissy on Aug 7, 2018
Transsexuals & Crossdressers

"Come over here princess, it's time for you to be my husband's little fuck-bunny." The time had come. He obediently walked over and she instructed him to drape himself over the stacked pillows, then bury his face in the corduroy pants on the other pillow. He did, and between the pillows, the bedspread and Susan's pants his whole body was now rubbing agai...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Casey's Submissive Journey Pt. 13

by corduroysissy on Aug 1, 2018
Transsexuals & Crossdressers

Since Susan had been treating him so nicely, Debbie suddenly felt a little strange when she abruptly walked out. Seeing the confusion on his face, Maxi said. "Don't worry Debbie she has things to do, she'll be back when she's ready to cum again." She slowly smiled. "Oh my, how amusing. Did you think you two were girlfriends now?" She chuckled. "Sorry siss...

Mistress Marisa's Estate Pt. 10

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... ****************************** "Mistress, I am yours, undying devotion..." punctuated by scream, real screams and shaking sobbing as I hit myself again, s...