Sissy Princess Stories

21,927 results
Orientation
Length
Source
Infinite Scroll

Caitlin and Mistress Vicky Ch. 02

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

I hummed softly as I put the finishing touches on the salmon. Teriyaki salmon was my wife's favorite dish and it filled me with pride to know that I was making her happy. My mouth watered slightly as I arranged the tray. (I would only be having a salad myself, as I had to maintain my figure.) Taking out a pocket mirror from my apron, I checked myself to ma...

A Husband Named Cathy Ch. 03

by cathynylons on Mar 6, 2018
Transsexuals & Crossdressers

When Randy and Brad had finished with me, Brad said, "Well, Randy we have to get going now," and he headed for the door with Randy getting up from the sofa. Before starting to follow Brad, Randy looked at me and said in a soft voice, "Stay away from my boyfriend, bitch." As Brad opened the door he turned and said, "Toni, we have new things at the store, f...

Man Disciplines Sissy Ch. 06

by LanaBehave on Sep 14, 2020
Transgender & Crossdressers

This is a fantasy. Scenes in reality should be built on consent, safety, and communication. No character in this story is less than 21 years of age. * Back in my own room, I threw myself on the sofa again, face down, and for a half a minute I just lay there, breathing a little fast, excited, ashamed, squirming a little in spite of myself, thinking of what...

Panty Posers

by EROTICbearscribe on Jun 1, 2020
Transgender & Crossdressers

PRIVATE PANTY SESSIONS Ch. 01 "Wait! What? Say that again." Doug, my roommate of two years, closed his eyes and took a deep breath. Tension hung heavy in the air. I allowed him to take all the time he needed to explain even though my mind was racing the way it does when your entire world has been turned upside down. I could see he was struggling. It look...

Truth or Dare Takes a Turn Pt. 02

by Cutiepie183 on Sep 14, 2020
Transgender & Crossdressers

Morning rises and I must have eventually fallen asleep during the night as I am awoken by a swift and stubborn kick to the stomach. "Rise and shine sissy boy, you've got a lot to do today" sprooked Luke as he looked down at my filthy curled up body. I peel myself off the hard cold concrete of the patio and instantly feel the pain of my cock being squeezed...

Serving Miss Sarah and The Girls

by oneguy4fun on Sep 12, 2017
BDSM

CHAPTER 1: THE ANNOUCNEMENT Joe had never been so excited about attending a seminar before. His cock actually stirred when the seminar request form came back approved. You would have thought he was going to Hedonism or a sex seminar but reality was quite the opposite. He would be going to a boring accounting seminar. The seminar itself is not what excited J...

College Misery Ch. 01

by newauthor19 on Sep 16, 2017
Fetish

Ever since words got out that James has some femboy porn hidden in his laptop it has been a nightmare for the 19 year old poor boy standing 5'8" and weighs merely 122lbs. His classmates have totally lost all respect for him. He was admired before for his friendly attire and kind hearted nature but now he is admired for his feminine body. He lives in a boy's...

My New Family Ch. 02

by eagle166 on Sep 15, 2017
Transsexuals & Crossdressers

The sun coming into my bedroom brings me out of my slumber, I feel pressure on my chest. I was in my bed sleeping, waking to Robin's left arm laying across my chest, his freshly shaven left leg draped over mine, his thighs exposed beneath his sexy white nightie. Looking down I see the top of his head laying on my shoulder. With my arm around him. I feel the...

Brittany's First Time Out

by LindseyAntoinette on Nov 26, 2019
Transgender & Crossdressers

"Ugh, I messed it up again," I groaned as I tried, once again, to apply a bright shade of red to my lips. My manicured hands had been shaking all night as I got myself ready. I finished off my cherry red lips with a layer of gloss and took a step back from the mirror to review my handiwork. My grey smoky eyes and red lips shone against my pale freshly shaven...

Halloween Agreement

by princess_nicole on Sep 16, 2017
Transsexuals & Crossdressers

Halloween was fast approaching. This made me nervous as my new girlfriend had gotten me to agree to a costume I would never have thought I'd wear. A school girl. She said it would be fun, and that nobody judges on Halloween. Not that she had to try convincing very much, I cave in to her every whim pretty much all the time. I guess you could say I have a fair...