Sissy Princess Stories

21,927 results
Orientation
Length
Source
Infinite Scroll

Sissy Slut Boy

by SissyBoiToi1 on Jan 2, 2017
Fetish

You wake up in your bed, in your attic bedroom. You sigh, not wanting to get out of bed. But then, you realize 2 things--one, your alarm clock didn't go off, you overslept! You have 5 minutes to get to the bus! And two--your bed is soaked in warm, smelly liquid. Did you wet yourself? (Just a note: The "catch the bus" route leads to diaper-related c...

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A Very Good Little Girl, I Am

by keptsissy on Sep 24, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** NOBODY IN THIS STORY IS LESS THAN 21 YEARS OF AGE. EVERYONE OF THE FICTIONAL CHARACTERS IN THIS STORY IS OF ADULT AGE AND CONSENTING. *** "Come on, little boy. Up on the bed, let's go." He stares at me. Sees the slight tears in my eyes, sees the shame on my face. He sees...

Jock Princess Ch. 05

by Sissyhalo on Sep 15, 2017
Transsexuals & Crossdressers

I wake up and it's still late and it's still dark outside with Logan having moved and moved me and I'm lying face down in the pillows as he's been fingering me and lubing me again. "Mmm...? What...more?" "Yeah, you don't want more Princess?" "I...oh...mmm...okay...not awake but...that's sooo good Logan." He chuckles and my buttcheeks get pulled apart mor...

Dominating Ken Pt. 09-10

by oneguy4fun on Sep 26, 2017
BDSM

PART 9: THE POWER OF THREE Kimmee's (Ken's) heels clicked across the marble floor of the hotel lobby. He was in a hurry to go nowhere. He figured if he walked fast enough no one would notice the secret underneath the feminine facade. Mistress Kareena had done such a fabulous job at hiding his masculinity and highlighting his feminine qualities that someone...

Sheila and Penny

by Sheila_TSSub on Sep 19, 2017
Transsexuals & Crossdressers

Part 1 I had been upstairs that morning doing my chores. I was dressed in a cute little yellow summer dress and leather heels with 4" wedge heels. When I came downstairs I found Mistress Tina (my wife) and Princess Gina (our daughter) in the den. There was a man there that was unknown to me. "Come here." Tina commanded. I went in and knelt beside her cha...

Maid in Heaven

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Many years ago my Mum worked as a bridal consultant for a well-known wedding dress shop. One day to get off College so I could bunk rugby I complained of having a stomachache. The situation was ridiculous. I'm a young man of 19 who had volunteered to continue with my education and study accounts so why the authorities insisted I had to do Rugby as part of th...

Not Sick Maid In Heaven

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Many years ago my Mum worked as a bridal consultant for a well-known wedding dress shop. One day to get off College so I could bunk rugby I complained of having a stomachache. The situation was ridiculous. I'm a young man of 19 who had volunteered to continue with my education and study accounts so why the authorities insisted I had to do Rugby as part of th...

Mistress Marisa's Estate Pt. 05

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... *************************** "Hurry up, just the things you need for the weekend, that sissy shit you do to look like a girl. Let's go." He's staring at m...

The Dragon Ring Ch. 04

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

The first days travel was wholly uneventful. We stopped to rest the equinininys mid morn; some people had brought snacks to eat while others including us took the air. My mistress declared that eating was bad for the digestion when one was thrown around on the track, which had turned to bare earth outside of the town. We stopped at an inn at lunch time t...

Mistress Marisa's Estate Pt. 06

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... *************************** His cock is huge. I barely get my hand to close around it. The head of it glistens from the k-y as my hand moves over the top,...